IP Library Granted Patent US 9,586,891
Granted Patent B2
US 9,586,891 · App. 14/234,916 · Granted Mar 7, 2017

Estrogen receptor ligands

Inventors: Aiping Cheng (Huddinge, SE); Neeraj Garg (Huddinge, SE); Lars Krüger (Huddinge, SE); Joakim Löfstedt (Huddinge, SE); Eva Koch (Huddinge, SE); Konrad Koehler (Huddinge, SE); Lars Hagberg (Huddinge, SE); Daniel Nöteberg (Huddinge, SE)
Assignee: Karo Pharma AB
C07C251/48A61K31/155A61K31/341A61K31/381A61K31/416A61K31/42A61K31/4418A61K31/47A61K31/472C07C209/68C07D207/327C07D213/58C07D215/12C07D215/14C07D217/14C07D217/16C07D231/12C07D233/64C07D235/16C07D261/08C07D277/30C07D277/34C07D295/155C07D307/54C07D307/68C07D307/87C07D317/60C07D333/20C07D333/24C07D409/10C07D413/10
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Quick Facts
Patent No.
US 9,586,891
App. No.
14/234,916
Granted
Mar 7, 2017
Kind
B2
Abstract

Compounds of formula (I) or a pharmaceutically acceptable ester, amide, carbamate or salt thereof, including a salt of such an ester, amide or carbamate in which R 1 to R 9 have meanings as defined in the Specification, are useful as estrogen receptor ligands.

Claims (394)

1. A compound of formula (I) or a pharmaceutically acceptable ester, amide, carbamate or salt thereof, including a salt of such an ester, amide or carbamate

in which

R 1 is selected from the group consisting of optionally substituted 5-10 membered heterocyclyl, optionally substituted phenyl, optionally substituted naphthyl, optionally substituted C 3-8 cycloalkyl, optionally substituted C 5-6 cycloalkenyl, optionally substituted phenylC 2-4 alkenyl, C 2-8 alkenyl, haloC 2-8 alkenyl, dihaloC 2-8 alkenyl, trihaloC 2-8 alkenyl, and C 3-8 cycloalkylC 2-4 alkenyl, wherein when said heterocyclyl, phenyl or naphthyl group or part of group is substituted, it is substituted with from 1 to 5 substituents, each substituent being independently selected from the group consisting of OR A , N(R B ) 2 , halogen, cyano, nitro, —C(O)C 1-4 alkyl, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, haloC 1-6 alkyl, dihaloC 1-6 alkyl and trihaloC 1-6 alkyl, and when said C 3-8 cycloalkyl or C 5-6 cycloalkenyl group is substituted, it is substituted with 1, 2 or 3 substituents selected from C 1-5 alkyl, C 1-5 alkenyl, C 1-5 alkynyl, C 1-5 alkyl substituted with up to 3 halogen atoms, —CO—C 1-5 alkyl, and halogen;

R 2 is selected from the group consisting of —C(NH 2 )═N—OH, —C(O)N(R C ) 2 , cyano, —CHO, —CH═N—OH, —C(O)NH—OH, —C(CO 2 H)═N—OH, —C(O—C 1-4 alkyl)═NH, —C(NH 2 )═N—NH 2 , —C(O)—C(O)—NH 2 , —C(O)CO 2 H, —CO 2 H, —CH 2 —CO 2 H, —CH(OH)CO 2 H, —CH 2 NH—CONH 2 , C 1-6 alkyl-NH 2 , C 1-6 alkyl-OH, —CH 2 SO 3 H, —NH—C(NH 2 )═NH, —NH—C(O)NH 2 , —N═C(—NH—CH 2 CH 2 —NH—), N(R B ) 2 , N(OH) 2 , NHSO 2 R D , —S—CN, —S—C(NH 2 )═NH, —S—C(NH 2 )═N—OH, SO 2 N(R E ) 2 , SO 3 H, cyanoC 1-6 alkyl, and optionally substituted 5-10 membered heterocyclyl containing from one to three nitrogen atoms, wherein when said heterocyclyl group is substituted, it is substituted with from 1 to 3 substituents, each substituent being independently selected from the group consisting of OR A , N(R B ) 2 , halogen, cyano, nitro, —C(O)C 1-4 alkyl, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, haloC 1-6 alkyl, dihaloC 1-6 alkyl and trihaloC 1-6 alkyl;

R 3 is selected from the group consisting of hydrogen, halogen, cyano, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-8 cycloalkyl, C 3-8 cycloalkylC 1-6 alkyl, haloC 1-6 alkyl, dihaloC 1-6 alkyl, trihaloC 1-6 alkyl, optionally substituted phenyl, optionally substituted phenylC 1-4 alkyl, optionally substituted 5-10 membered heterocyclyl, and optionally substituted 5-10 membered heterocyclylC 1-4 alkyl, wherein when said phenyl or heterocyclyl group or part of group is substituted, it is substituted with from 1 to 5 substituents, each substituent being independently selected from the group consisting of OR A , N(R B ) 2 , halogen cyano, nitro, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, haloC 1-6 alkyl, dihaloC 1-6 alkyl and trihaloC 1-6 alkyl;

R 4 is selected from the group consisting of hydrogen, halogen, cyano, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, and haloC 1-6 alkyl, dihaloC 1-6 alkyl, and trihaloC 1-6 alkyl;

each of R 5 , R 6 , R 8 and R 9 is independently selected from the group consisting of hydrogen, OR A , N(R B ) 2 , halogen, cyano, nitro, —C(O)C 1-4 alkyl, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, haloC 1-6 alkyl, dihaloC 1-6 alkyl and trihaloC 1-6 alkyl;

R 7 is OR A ;

or R 6 and R 7 may, together with the atoms they are attached to, form a 5-, 6- or 7-membered cyclic group optionally containing one to three heteroatoms selected from O, N and S, said 5-, 6- or 7-membered cyclic group being optionally substituted with one of more groups selected from OR A , cyano, nitro, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, halo C 1-6 alkyl, dihalo C 1-6 alkyl and trihalo C 1-6 alkyl; and

each R A , each R B , each R C , each R D and each R E is independently selected from the group consisting of hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-8 cycloalkyl and C 3-8 cycloalkylC 1-6 alkyl;

each optionally substituted by from 1 to 3 halogen atoms.

2. A compound as claimed in claim 1 , in which R 1 is selected from the group consisting of optionally substituted 5-10 membered heterocyclyl, optionally substituted phenyl, optionally substituted naphthyl, optionally substituted C 5-6 cycloalkenyl, optionally substituted phenylC 2-4 alkenyl, C 2-8 alkenyl, haloC 2-8 alkenyl, dihaloC 2-8 alkenyl, trihaloC 2-8 alkenyl, and C 3-8 cycloalkylC 2-4 alkenyl, wherein when said heterocyclyl or phenyl or naphthyl group or part of group is substituted, it is substituted with from 1 to 5 substituents, each substituent being independently selected from the group consisting of OR A , N(R B ) 2 , halogen, cyano, nitro, C 1-6 alkyl, haloC 1-6 alkyl, dihaloC 1-6 alkyl and trihaloC 1-6 alkyl, and wherein when said C 5-6 cycloalkenyl group is substituted, it is substituted with 1 or 2 substitutents selected from halogen atoms and methyl groups.

3. A compound as claimed in claim 2 , in which R 1 is selected from the group consisting of optionally substituted 5-10 membered heterocyclyl, optionally substituted phenyl, optionally substituted naphthyl, optionally substituted C 5-6 cycloalkenyl, optionally substituted phenylC 2-4 alkenyl, C 2-8 alkenyl, C 3-8 cycloalkyl, and C 3-8 cycloalkylC 2-4 alkenyl, wherein when said heterocyclyl or phenyl or naphthyl group or part of group is substituted, it is substituted with from 1 to 5 substituents, each substituent being independently selected from the group consisting of OR A , halogen, C 1-6 alkyl, haloC 1-6 alkyl, dihaloC 1-6 alkyl and trihaloC 1-6 alkyl, and wherein where said optionally substituted C 5-6 cycloalkenyl group is substituted, it is substituted with 1 or two substituents selected from halogen atoms and methyl groups.

4. A compound as claimed in claim 1 , in which R1 represents an optionally substituted isoxazolyl, isothiazolyl, pyrrolyl, pyrazolyl, pyridyl or pyrrolidinyl group.

5. A compound as claimed in claim 1 , in which R 2 is selected from the group consisting of —C(NH 2 )═N—OH, —C(O)N(R C ) 2 , cyano, —CHO, —CH═N—OH, —C(O)NH—OH, —C(CO 2 H)═N—OH, —C(O—C 1-4 alkyl)═NH, —C(NH 2 )═N—NH 2 , —C(O)—C(O)—NH 2 , —CH 2 NH—CONH 2 , C 1-6 alkyl-NH 2 , —NH—C(NH 2 )═NH, —NH—C(O)NH 2 , —N═C(—NH—CH 2 CH 2 —NH—), N(OH)— 2 , —S—CN, —S—C(NH 2 )═NH, —S—C(NH 2 )═N—OH, cyanoC 1-6 alkyl, and an optionally substituted 5-6 membered heterocyclyl containing from one to three nitrogen atoms; wherein when said heterocyclyl group is substituted, it is substituted with from 1 to 3 substituents, each substituent being independently selected from the group consisting of OH, halogen, cyano, nitro, C 1-4 alkyl, haloC 1-4 alkyl, dihaloC 1-4 alkyl and trihaloC 1-4 alkyl.

6. A compound as claimed in claim 5 , in which R 2 represents —C(NH 2 )═N—OH, —C(O)NH 2 , —CH═N—OH, cyano, or pyrazolyl.

7. A compound as claimed in claim 1 , in which R 3 is selected from the group consisting of hydrogen, halogen, cyano, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-8 cycloalkyl, C 3-8 cycloalkylC 1-6 alkyl, haloC 1-6 alkyl, dihaloC 1-6 alkyl, trihaloC 1-6 alkyl, phenyl, and phenylC 1-4 alkyl.

8. A compound as claimed in claim 7 , in which R 3 represents halogen, cyano, C 1-6 alkyl, C 2-6 alkenyl, trihaloC 1-6 alkyl, phenyl, or phenylC 1-2 alkyl.

9. A compound as claimed in claim 1 , in which each of R 5 , R 6 , R 8 and R 9 is independently selected from the group consisting of hydrogen, OR A , N(R B ) 2 , halogen, cyano, nitro, C 1-6 alkyl, haloC 1-6 alkyl, dihaloC 1-6 alkyl and trihaloC 1-6 alkyl.

10. A compound as claimed in claim 9 , in which each of R 5 , R 6 , R 8 and R 9 is independently selected from the group consisting of hydrogen, halogen, methyl and trifluoromethyl.

11. A compound as claimed in ( claim 1 ), in which R 7 represents OR A .

12. A compound as claimed in claim 11 , in which R 7 represents OH.

13. A compound as claimed in claim 1 , in which each of R 5 , R 8 and R 9 is independently selected from the group consisting of hydrogen, OR A , N(R B ) 2 , halogen, cyano, nitro, C 1-6 alkyl, haloC 1-6 alkyl, dihaloC 1-6 alkyl and trihaloC 1-6 alkyl; and R 6 and R 7 , together with the atoms they are attached to, form a 5-, 6- or 7-membered cyclic group optionally containing one to three heteroatoms selected from O, N and S, said 5-, 6- or 7-membered cyclic group being optionally substituted with one of more groups selected from OR A , cyano, nitro, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, halo C 1-6 alkyl, dihalo C 1-6 alkyl and trihalo C 1-6 alkyl.

14. A compound as claimed in claim 13 , in which each of R 5 , R 8 and R 9 is independently selected from the group consisting of hydrogen and halogen.

15. A compound as claimed in claim 13 , in which R 6 and R 7 , together with the atoms they are attached to, form a 5-, 6- or 7-membered cyclic group optionally containing one to three heteroatoms selected from O and N.

16. A compound as claimed in claim 1 , which is any one of the following compounds:

N′,4′-dihydroxy-2-(3-methylthiophen-2-yl)-5-propyl-[1,1′-biphenyl]-3-carboximidamide

2-(3,5-dimethylisoxazol-4-yl)-N′,4′-dihydroxy-5-methyl-[1,1′-biphenyl]-3-carboximidamide

2-(3,5-dimethylisoxazol-4-yl)-N′,4′-dihydroxy-5-propyl-[1,1′-biphenyl]-3-carboximidamide

2-(3,5-dimethylisoxazol-4-yl)-4′-hydroxy-5-propyl-[1,1′-biphenyl]-3-carboxamide

2-(3,5-dimethylisoxazol-4-yl)-4′-hydroxy-5-propyl-[1,1′-biphenyl]-3-carbonitrile

N′,4′-dihydroxy-5-methyl-2-(3-methylthiophen-2-yl)-[1,1′-biphenyl]-3-carboximidamide

3′,5′-difluoro-N′,4′-dihydroxy-2-(3-methylthiophen-2-yl)-5-propyl-[1,1′-biphenyl]-3-carboximidamide

2-bromo-3′,5′-difluoro-N′,4′-dihydroxy-5-propyl-[1,1′-biphenyl]-3-carboximidamide

2-(3,5-dimethylisoxazol-4-yl)-3′,5′-difluoro-N′,4′-dihydroxy-5-propyl-[1,1′-biphenyl]-3-carboximidamide

5-bromo-N′,4′-dihydroxy-2-(3-methylthiophen-2-yl)-[1,1′-biphenyl]-3-carboximidamide

5-bromo-N′,4′-dihydroxy-2-iodo-[1,1′-biphenyl]-3-carboximidamide

5′-bromo-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″-fluoro-N′,4-dihydroxy-2″,5′-dimethyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″-fluoro-4-hydroxy-2″,5′-dimethyl-[1,1′:2′,1″-terphenyl]-3′-carboxamide

5-chloro-2-(3,5-dimethylisoxazol-4-yl)-N′,4′-dihydroxy-[1,1′-biphenyl]-3-carboximidamide

5-chloro-2-(3,5-dimethylisoxazol-4-yl)-4′-hydroxy-[1,1′-biphenyl]-3-carboxamide

2-(3,5-dimethylisoxazol-4-yl)-3′-fluoro-N′,4′-dihydroxy-5-propyl-[1,1′-biphenyl]-3-carboximidamide

2-(2,4-dimethylfuran-3-yl)-4′-hydroxy-5-propyl-[1,1′-biphenyl]-3-carbonitrile

2-(2,4-dimethylfuran-3-yl)-N′,4′-dihydroxy-5-propyl-[1,1′-biphenyl]-3-carboximidamide

2-(2,4-dimethylfuran-3-yl)-4′-hydroxy-5-propyl-[1,1′-biphenyl]-3-carboxamide

N′,4′-dihydroxy-2-iodo-5-propyl-[1,1′-biphenyl]-3-carboximidamide

N′,4′-dihydroxy-2-(4-methylthiophen-3-yl)-5-propyl-[1,1′-biphenyl]-3-carboximidamide

N′,4-dihydroxy-5′-propyl-2″-(trifluoromethoxy)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2-(2,4-dimethylthiophen-3-yl)-N′,4′-dihydroxy-5-propyl-[1,1′-biphenyl]-3-carboximidamide

N′,4-dihydroxy-5′-propyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2-((E)-2-cyclopropylvinyl)-N′,4′-dihydroxy-5-propyl-[1,1′-biphenyl]-3-carboximidamide

N′,4′-dihydroxy-2-(3-methylbut-2-en-2-yl)-5-propyl-[1,1′-biphenyl]-3-carboximidamide

N′,4-dihydroxy-3″-methyl-5′-propyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″-fluoro-N′,4-dihydroxy-2″-methyl-5′-propyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2″-ethyl-N′,4-dihydroxy-5′-propyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4′-dihydroxy-5-propyl-2-(thiophen-2-yl)-[1,1′-biphenyl]-3-carboximidamide

N′,4′-dihydroxy-5-propyl-2-(quinolin-5-yl)-[1,1′-biphenyl]-3-carboximidamide

3″-chloro-N′,4-dihydroxy-5′-propyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4′-dihydroxy-5-propyl-2-(pyridin-3-yl)-[1,1′-biphenyl]-3-carboximidamide

2-(benzofuran-5-yl)-N′,4′-dihydroxy-5-propyl-[1,1′-biphenyl]-3-carboximidamide

4″-chloro-N′,4-dihydroxy-5′-propyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4′-dihydroxy-5-propyl-2-(pyridin-4-yl)-[1,1′-biphenyl]-3-carboximidamide

N′,4′-dihydroxy-2-(1-phenylvinyl)-5-propyl-[1,1′-biphenyl]-3-carboximidamide

2-(5-chlorothiophen-2-yl)-N′,4′-dihydroxy-5-propyl-[1,1′-biphenyl]-3-carboximidamide

5″-fluoro-N′,4-dihydroxy-2″-methoxy-5′-propyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4′-dihydroxy-2-(isoquinolin-6-yl)-5-propyl-[1,1′-biphenyl]-3-carboximidamide

2-(benzofuran-3-yl)-N′,4′-dihydroxy-5-propyl-[1,1′-biphenyl]-3-carboximidamide

5″-fluoro-N′,4-dihydroxy-2″-methoxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″-fluoro-N′,4-dihydroxy-2″-methyl-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4-dihydroxy-2″-methyl-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4-dihydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4′-dihydroxy-2-(4-methylthiophen-3-yl)-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboximidamide

2-(2,4-dimethylthiophen-3-yl)-N′,4′-dihydroxy-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboximidamide

N′,4′-dihydroxy-2-iodo-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboximidamide

2″,5″-difluoro-N′,4-dihydroxy-5′-propyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2-(1,3-dimethyl-1H-pyrrol-2-yl)-N′,4′-dihydroxy-5-propyl-[1,1′-biphenyl]-3-carboximidamide

3″,5″-difluoro-N′,4-dihydroxy-5′-propyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2-(2,4-dimethylfuran-3-yl)-N′,4′-dihydroxy-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboximidamide

3′-chloro-5′-fluoro-N′,4′-dihydroxy-2-(3-methylthiophen-2-yl)-5-propyl-[1,1′-biphenyl]-3-carboximidamide

N′-hydroxy-3-(1H-indazol-5-yl)-2-(3-methylthiophen-2-yl)-5-propylbenzimidamide

3′-fluoro-N′,4′-dihydroxy-2-(3-methylthiophen-2-yl)-5-propyl-[1,1′-biphenyl]-3-carboximidamide

3′-chloro-N′,4′-dihydroxy-2-(3-methylthiophen-2-yl)-5-propyl-[1,1′-biphenyl]-3-carboximidamide

3′,5′-dichloro-N′,4′-dihydroxy-2-(3-methylthiophen-2-yl)-5-propyl-[1,1′-biphenyl]-3-carboximidamide

N′,4′-dihydroxy-3′-methyl-2-(3-methylthiophen-2-yl)-5-propyl-[1,1′-biphenyl]-3-carboximidamide

2′-fluoro-N′,4′-dihydroxy-2-(3-methylthiophen-2-yl)-5-propyl-[1,1′-biphenyl]-3-carboximidamide

2′,3′-difluoro-N′,4′-dihydroxy-2-(3-methylthiophen-2-yl)-5-propyl-[1,1′-biphenyl]-3-carboximidamide

2′,5′-difluoro-N′,4′-dihydroxy-2-(3-methylthiophen-2-yl)-5-propyl-[1,1′-biphenyl]-3-carboximidamide

N′,4′-dihydroxy-2-(2-methylallyl)-5-propyl-[1,1′-biphenyl]-3-carboximidamide

2-allyl-N′,4′-dihydroxy-5-propyl-[1,1′-biphenyl]-3-carboximidamide

N′,4′-dihydroxy-5-propyl-2-vinyl-[1,1′-biphenyl]-3-carboximidamide

5-bromo-N′,4′-dihydroxy-2-(1-methyl-1H-imidazol-5-yl)-[1,1′-biphenyl]-3-carboximidamide

N′,4′-dihydroxy-5-propyl-2-(pyridin-2-yl)-[1,1′-biphenyl]-3-carboximidamide

N′,4′-dihydroxy-2-(2-methoxythiazol-4-yl)-5-propyl-[1,1′-biphenyl]-3-carboximidamide

N′,4′-dihydroxy-5-propyl-2-(thiazol-5-yl)-[1,1′-biphenyl]-3-carboximidamide

N′,4′-dihydroxy-5-propyl-2-(thiazol-2-yl)-[1,1′-biphenyl]-3-carboximidamide

5′-ethyl-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4-dihydroxy-5′-isobutyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4-dihydroxy-5′-((E)-prop-1-en-1-yl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-allyl-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-butyl-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2-(2,5-dimethyl-1H-pyrrol-1-yl)-N′,4′-dihydroxy-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboximidamide

4-hydroxy-5′-propyl-[1,1′:2′,1″-terphenyl]-3′-carbaldehyde oxime

5′-propyl-3′-(1H-pyrazol-4-yl)-[1,1′:2′,1″-terphenyl]-4-ol

5-chloro-2-(3,5-dimethylisoxazol-4-yl)-N′,4′-dihydroxy-3′-nitro-[1,1′-biphenyl]-3-carboximidamide

5′-chloro-5″-fluoro-N′,4-dihydroxy-2″-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-chloro-5″-fluoro-N′,4-dihydroxy-2″-methoxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5-chloro-N′,4′-dihydroxy-2-(4-methylthiophen-3-yl)-[1,1′-biphenyl]-3-carboximidamide

5′-chloro-N′,4-dihydroxy-2″-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2-(2,4-dimethylthiophen-3-yl)-N′,4′-dihydroxy-[1,1′-biphenyl]-3-carboximidamide

5-chloro-2-(2,4-dimethylthiophen-3-yl)-N′,4′-dihydroxy-[1,1′-biphenyl]-3-carboximidamide

2″-chloro-5″-fluoro-N′,4-dihydroxy-5′-propyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

6′-chloro-N′,4-dihydroxy-5′-propyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4-dihydroxy-5′,6′-dipropyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4′-dihydroxy-2-(3-methylthiophen-2-yl)-[1,1′-biphenyl]-3-carboximidamide

5′-bromo-6′-chloro-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

6′-chloro-N′,4-dihydroxy-5′-phenyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

6′-chloro-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4-dihydroxy-6′-methyl-5′-propyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″,6′-difluoro-N′,4-dihydroxy-2″-methyl-5′-propyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″,6′-difluoro-4-hydroxy-2″-methyl-5′-propyl-[1,1′:2′,1″-terphenyl]-3′-carboxamide

4-hydroxy-6′-methyl-5′-propyl-[1,1′:2′,1″-terphenyl]-3′-carbaldehyde oxime

5″,6′-difluoro-N′,4-dihydroxy-2″-methoxy-5′-propyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″,6′-difluoro-4-hydroxy-2″-methoxy-5′-propyl-[1,1′:2′,1″-terphenyl]-3′-carboxamide

6′-fluoro-4-hydroxy-5′-propyl-[1,1′:2′,1″-terphenyl]-3′-carboxamide

6′-fluoro-N′,4-dihydroxy-2″-methyl-5′-propyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

6-fluoro-N′,4′-dihydroxy-2-(4-methylthiophen-3-yl)-5-propyl-[1,1′-biphenyl]-3-carboximidamide

6′-fluoro-4-hydroxy-2″-methyl-5′-propyl-[1,1′:2′,1″-terphenyl]-3′-carboxamide

6-fluoro-4′-hydroxy-2-(4-methylthiophen-3-yl)-5-propyl-[1,1′-biphenyl]-3-carboxamide

2-(2,4-dimethylthiophen-3-yl)-6-fluoro-N′,4′-dihydroxy-5-propyl-[1,1′-biphenyl]-3-carboximidamide

5′-chloro-5″-fluoro-4-hydroxy-2″-methoxy-[1,1′:2′,1″-terphenyl]-3′-carboxamide

6′-fluoro-N′,4-dihydroxy-5′-propyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″-fluoro-N′,4-dihydroxy-2″-methoxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″-fluoro-N′,4-dihydroxy-2″-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4-dihydroxy-5′-(trifluoromethyl)-2″-vinyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2″-ethyl-N′,4-dihydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″-fluoro-N′,4-dihydroxy-2″-methyl-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″-fluoro-N′,4-dihydroxy-2″-methoxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′,6′-dichloro-5″-fluoro-N′,4-dihydroxy-2″-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″,5″-difluoro-N′,4-dihydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″-chloro-N′,4-dihydroxy-2″-methoxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2″-ethynyl-N′,4-dihydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″-chloro-5″-fluoro-N′,4-dihydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″-fluoro-N′,4-dihydroxy-2″,5′-bis(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″,5″-difluoro-N′,4-dihydroxy-2″-methoxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-methyl-3′-(1H-pyrazol-4-yl)-[1,1′:2′,1″-terphenyl]-4-ol

3″,5″-difluoro-5′-propyl-3′-(1H-pyrazol-4-yl)-[1,1′:2′,1″-terphenyl]-4-ol

N′,4-dihydroxy-5′-phenyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-benzyl-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4-dihydroxy-5′-phenethyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2,5″-difluoro-N′,4-dihydroxy-2″-methyl-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2,5″-difluoro-N′,4-dihydroxy-2″-methoxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2-fluoro-N′,4-dihydroxy-2″-methyl-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2-fluoro-N′,4-dihydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″-chloro-2-fluoro-N′,4-dihydroxy-2″-methoxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2,3″-difluoro-N′,4-dihydroxy-2″-methoxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2,3″,5″-trifluoro-N′,4-dihydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2-fluoro-N′,4-dihydroxy-5′-(trifluoromethyl)-2″-vinyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″-chloro-2-fluoro-4-hydroxy-2″-methoxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboxamide

2-fluoro-4-hydroxy-5′-(trifluoromethyl)-2″-vinyl-[1,1′:2′,1″-terphenyl]-3′-carboxamide

3″-chloro-2,5″-difluoro-N′,4-dihydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″-chloro-2,5″-difluoro-4-hydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboxamide

2″-ethynyl-2-fluoro-N′,4-dihydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-chloro-3″,5″-difluoro-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-chloro-3″-fluoro-N′,4-dihydroxy-2″-methoxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′,5″-dichloro-N′,4-dihydroxy-2″-methoxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″-chloro-2-fluoro-N′,4-dihydroxy-2″-methyl-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″-chloro-2-fluoro-4-hydroxy-2″-methyl-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboxamide

N′,4-dihydroxy-5′-methyl-2″-vinyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″,5″-difluoro-N′,4-dihydroxy-2″-methoxy-5′-methyl-[1,1′: 2′,1″-terphenyl]-3′-carboximidamide

3″-fluoro-N′,4-dihydroxy-2″-methoxy-5′-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″-fluoro-N′,4-dihydroxy-2″-methoxy-5′-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″-chloro-5″-fluoro-N′,4-dihydroxy-5′-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″-chloro-N′,4-dihydroxy-2″,5′-dimethyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″-chloro-N′,4-dihydroxy-2″-methyl-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″-chloro-N′,4-dihydroxy-2″-methyl-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″-chloro-N′,4-dihydroxy-2″-methoxy-5′-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2″-chloro-5″-fluoro-N′,4-dihydroxy-5′-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4-dihydroxy-5′-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4-dihydroxy-3″,5′-dimethyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″-chloro-N′,4-dihydroxy-5′-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4-dihydroxy-3″-methoxy-5′-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

4″-fluoro-N′,4-dihydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

4″-chloro-N′,4-dihydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4-dihydroxy-2″-methoxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

4″-fluoro-N′,4-dihydroxy-2″-methoxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4-dihydroxy-2″-isopropyl-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2-(3,5-dimethylisoxazol-4-yl)-N′,4′-dihydroxy-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboximidamide

2-(3,5-dimethylisoxazol-4-yl)-4′-hydroxy-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboxamide

3″-chloro-4-hydroxy-2″-methyl-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboxamide

N′,4-dihydroxy-2″,5″-dimethyl-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4-dihydroxy-2″-methoxy-5″-methyl-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2″-chloro-N′,4-dihydroxy-5″-methyl-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-fluoro-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″-chloro-5′-fluoro-N′,4-dihydroxy-2″-methoxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″,5′-difluoro-N′,4-dihydroxy-2″-methoxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″,5′,5″-trifluoro-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″-chloro-5′,5″-difluoro-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-fluoro-N′,4-dihydroxy-2″-vinyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-chloro-N′,4-dihydroxy-2″,5″-dimethyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4-dihydroxy-2″,5″-dimethyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2″-chloro-4-hydroxy-5″-methyl-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboxamide

3″-chloro-N′,4-dihydroxy-5″-methyl-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2″,5″-dichloro-N′,4-dihydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″-chloro-N′,4-dihydroxy-2″-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″-chloro-N′,4-dihydroxy-2″-methoxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″,5″-difluoro-N′,4-dihydroxy-5′-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″,5″-difluoro-4-hydroxy-5′-methyl-[1,1′:2′,1″-terphenyl]-3′-carboxamide

3″-chloro-4-hydroxy-5″-methyl-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboxamide

2″,5″-dichloro-4-hydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboxamide

3″,5″-dichloro-N′,4-dihydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″,5″-dichloro-N′,4-dihydroxy-5′-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2-(3,5-dimethylisoxazol-4-yl)-2′-fluoro-N′,4′-dihydroxy-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboximidamide

2-(3,5-dimethylisoxazol-4-yl)-2′-fluoro-4′-hydroxy-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboxamide

3″,5″-difluoro-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″,5″-difluoro-4-hydroxy-[1,1′:2′,1″-terphenyl]-3′-carboxamide

3″-fluoro-N′,4-dihydroxy-2″-methoxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″-fluoro-4-hydroxy-2″-methoxy-[1,1′:2′,1″-terphenyl]-3′-carboxamide

2″-ethyl-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

4″-chloro-2″-fluoro-N′,4-dihydroxy-5′-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

4″-chloro-3″-fluoro-N′,4-dihydroxy-5′-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4-dihydroxy-2″-methoxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-chloro-N′,4-dihydroxy-2″-methoxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

4″-fluoro-N′,4-dihydroxy-2″-methoxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-chloro-4″-fluoro-N′,4-dihydroxy-2″-methoxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″-chloro-N′,4-dihydroxy-5′,5″-dimethyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2″,5″-dichloro-N′,4-dihydroxy-5′-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″,5″-difluoro-4-hydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboxamide

N′,4-dihydroxy-4″,5′-dimethyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4-dihydroxy-2″,4″,5′-trimethyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

4″-fluoro-N′,4-dihydroxy-5′-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2″,4″-difluoro-N′,4-dihydroxy-5′-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″-chloro-5′-fluoro-N′,4-dihydroxy-2″-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′,5″-difluoro-N′,4-dihydroxy-2″-methoxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2″-chloro-5′-fluoro-N′,4-dihydroxy-5″-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2″,5″-dichloro-5′-fluoro-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-fluoro-N′,4-dihydroxy-2″-methoxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

4″,5′-difluoro-N′,4-dihydroxy-2″-methoxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-fluoro-N′,4-dihydroxy-2″,5″-dimethyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-fluoro-N′,4-dihydroxy-2″-methoxy-5″-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4-dihydroxy-2″-methoxy-5″-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4-dihydroxy-2″-methoxy-5′,5″-dimethyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

4″-fluoro-N′,4-dihydroxy-2″-methoxy-5′-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2″-chloro-N′,4-dihydroxy-5′,5″-dimethyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4-dihydroxy-5′-methyl-2″-(trifluoromethoxy)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4-dihydroxy-2″-methoxy-5′-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″,5″-difluoro-N′,4-dihydroxy-5′-methoxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″-fluoro-N′,4-dihydroxy-2″,5′-dimethoxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2-(5-fluoro-2-methoxypyridin-3-yl)-N′,4′-dihydroxy-5-methyl-[1,1′-biphenyl]-3-carboximidamide

N′,4′-dihydroxy-5-methyl-2-(2-methylpyridin-3-yl)-[1,1′-biphenyl]-3-carboximidamide

N′,4′-dihydroxy-2-(2-methoxypyridin-3-yl)-5-methyl-[1,1′-biphenyl]-3-carboximidamide

2-(3,5-dimethylisothiazol-4-yl)-N′,4′-dihydroxy-5-methyl-[1,1′-biphenyl]-3-carboximidamide

N′,4-dihydroxy-5′-methoxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2-(3,5-dimethylisothiazol-4-yl)-4′-hydroxy-5-methyl-[1,1′-biphenyl]-3-carboxamide

5-chloro-2-(5-fluoro-2-methoxypyridin-3-yl)-N′,4′-dihydroxy-[1,1′-biphenyl]-3-carboximidamide

2-(5-fluoro-2-methoxypyridin-3-yl)-4′-hydroxy-5-methyl-[1,1′-biphenyl]-3-carboxamide

2-(3,5-dimethylisothiazol-4-yl)-N′,4′-dihydroxy-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboximidamide

5-chloro-2-(3,5-dimethylisothiazol-4-yl)-N′,4′-dihydroxy-[1,1′-biphenyl]-3-carboximidamide

4″-fluoro-N′,4-dihydroxy-2″-methyl-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2″,4″-difluoro-N′,4-dihydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4′-dihydroxy-2-(4-methylpyridin-3-yl)-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboximidamide

2-(2,5-dimethylpyridin-3-yl)-N′,4′-dihydroxy-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboximidamide

2″-chloro-4″-fluoro-N′,4-dihydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

4″,5″-difluoro-N′,4-dihydroxy-2″-methyl-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2″,5″-difluoro-N′,4-dihydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4′-dihydroxy-2-(pyridin-3-yl)-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboximidamide

2-(2,3-dihydrobenzofuran-7-yl)-N′,4′-dihydroxy-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboximidamide

2-(benzofuran-7-yl)-N′,4′-dihydroxy-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboximidamide

N′,4′-dihydroxy-2-(1-methyl-1H-indol-7-yl)-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboximidamide

2″-chloro-5″-fluoro-N′,4-dihydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″-chloro-2″-fluoro-N′,4-dihydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2-(4-fluorobenzofuran-7-yl)-N′,4′-dihydroxy-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboximidamide

3″,4″-difluoro-N′,4-dihydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-chloro-2″,4″-difluoro-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-chloro-2″,5″-difluoro-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2-(benzo[d][1,3]dioxol-4-yl)-N′,4′-dihydroxy-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboximidamide

3″,4″,5″-trifluoro-N′,4-dihydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-chloro-3″,4″-difluoro-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-chloro-3″,4″,5″-trifluoro-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5-chloro-N′,4′-dihydroxy-2-(4-methylpyridin-3-yl)-[1,1′-biphenyl]-3-carboximidamide

5′,5″-dichloro-2″-fluoro-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2″,5′-dichloro-5″-fluoro-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-chloro-2″-fluoro-N′,4-dihydroxy-5″-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-chloro-2″-fluoro-N′,4-dihydroxy-4″-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2-(5-fluoro-2-methoxypyridin-3-yl)-N′,4′-dihydroxy-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboximidamide

5′-chloro-N′,4-dihydroxy-2″,4″-dimethoxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-chloro-4-hydroxy-2″,4″-dimethoxy-[1,1′:2′,1″-terphenyl]-3′-carbonitrile

5-chloro-2-(5-chloro-2-methoxypyridin-3-yl)-N′,4′-dihydroxy-[1,1′-biphenyl]-3-carboximidamide

5-chloro-2-(5-chloro-2-methoxypyridin-3-yl)-4′-hydroxy-[1,1′-biphenyl]-3-carboxamide

5-chloro-2-(2,5-dimethylpyridin-3-yl)-N′,4′-dihydroxy-[1,1′-biphenyl]-3-carboximidamide

5-chloro-2-(2,5-dimethylpyridin-3-yl)-4′-hydroxy-[1,1′-biphenyl]-3-carboxamide

2-(benzo[d][1,3]dioxol-4-yl)-5-chloro-N′,4′-dihydroxy-[1,1′-biphenyl]-3-carboximidamide

5-chloro-N′,4′-dihydroxy-2-(naphthalen-2-yl)-[1,1′-biphenyl]-3-carboximidamide

5-chloro-N′,4′-dihydroxy-2-(isoquinolin-6-yl)-[1,1′-biphenyl]-3-carboximidamide

5-chloro-N′,4′-dihydroxy-2-(quinolin-6-yl)-[1,1′-biphenyl]-3-carboximidamide

5-chloro-N′,4′-dihydroxy-2-(1-methyl-1H-benzo[d]imidazol-5-yl)-[1,1′-biphenyl]-3-carboximidamide

5-chloro-4′-hydroxy-2-(1-methyl-1H-benzo[d]imidazol-5-yl)-[1,1′-biphenyl]-3-carboxamide

2-(5-chloro-2-methoxypyridin-3-yl)-N′,4′-dihydroxy-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboximidamide

2″-fluoro-N′,4-dihydroxy-5″-methyl-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5-chloro-2-(6-chloro-2-methoxypyridin-3-yl)-N′,4′-dihydroxy-[1,1′-biphenyl]-3-carboximidamide

5-chloro-N′,4′-dihydroxy-2-(2-methoxy-5-methylpyridin-3-yl)-[1,1′-biphenyl]-3-carboximidamide

5-chloro-2-(cyclopent-1-en-1-yl)-N′,4′-dihydroxy-[1,1′-biphenyl]-3-carboximidamide

5-chloro-2-(cyclopent-1-en-1-yl)-4′-hydroxy-[1,1′-biphenyl]-3-carboxamide

2-(cyclopent-1-en-1-yl)-N′,4′-dihydroxy-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboximidamide

2-(cyclopent-1-en-1-yl)-4′-hydroxy-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboxamide

5′-bromo-5″-fluoro-N′,4-dihydroxy-2″-methoxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-bromo-5″-fluoro-N′,4-dihydroxy-2″-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-bromo-3″-fluoro-N′,4-dihydroxy-2″-methoxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-bromo-N′,4-dihydroxy-2″,5″-dimethyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-bromo-N′,4-dihydroxy-5″-methoxy-2″-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-bromo-N′,4-dihydroxy-2″-methoxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-bromo-4″-fluoro-N′,4-dihydroxy-2″-methoxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″-fluoro-N′,4-dihydroxy-5′-(trifluoromethyl)-2″-vinyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2,5″-difluoro-N′,4-dihydroxy-5′-(trifluoromethyl)-2″-vinyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″-chloro-N′,4-dihydroxy-5′-(trifluoromethyl)-2″-vinyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2″-ethynyl-5″-fluoro-N′,4-dihydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

4-hydroxy-2″-methoxy-5″-methyl-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboxamide

5′-bromo-5″-chloro-N′,4-dihydroxy-2″-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-bromo-3″,5″-difluoro-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-bromo-3″-chloro-5″-fluoro-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-bromo-2″-chloro-5″-fluoro-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-bromo-4″-chloro-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-bromo-2″,5″-dichloro-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-bromo-2″-chloro-N′,4-dihydroxy-5″-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5-bromo-2-(3,5-dimethylisoxazol-4-yl)-N′,4′-dihydroxy-[1,1′-biphenyl]-3-carboximidamide

3-chloro-5-fluoro-N′,4-dihydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3-chloro-5-fluoro-4-hydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboxamide

3,5′-dichloro-3″,5,5″-trifluoro-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3′-chloro-2-(3,5-dimethylisoxazol-4-yl)-5′-fluoro-N′,4′-dihydroxy-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboximidamide

3-chloro-3″,5,5″-trifluoro-N′,4-dihydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3-chloro-5,5″-difluoro-N′,4-dihydroxy-2″-methoxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3-chloro-5-fluoro-N′,4-dihydroxy-2″-methoxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-chloro-3″,5″-difluoro-N′-hydroxy-4-methoxy-3-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-chloro-3″,5″-difluoro-N′,4-dihydroxy-3-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5-chloro-2-(3,5-dimethylisoxazol-4-yl)-N′,4′-dihydroxy-3′-methyl-[1,1′-biphenyl]-3-carboximidamide

5′-chloro-N′,4-dihydroxy-2″,3-dimethyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-chloro-5″-fluoro-N′,4-dihydroxy-2″-methoxy-3-methyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5′-chloro-5″-fluoro-4-hydroxy-2″-methoxy-3-methyl-[1,1′:2′,1″-terphenyl]-3′-carboxamide

5′-chloro-3″,5″-difluoro-N′,4-dihydroxy-3-isopropyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2′-(3,5-dimethylisoxazol-4-yl)-3′-(1H-1,2,3-triazol-4-yl)-5′-(trifluoromethyl)-[1,1′-biphenyl]-4-ol

N′,4-dihydroxy-5′-(trifluoromethoxy)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″,5″-difluoro-N′,4-dihydroxy-5′-(trifluoromethoxy)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″-chloro-N′,4-dihydroxy-2″-methoxy-5′-(trifluoromethoxy)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

4-hydroxy-5′-(trifluoromethoxy)-[1,1′:2′,1″-terphenyl]-3′-carboxamide

3″,5″-difluoro-4-hydroxy-5′-(trifluoromethoxy)-[1,1′:2′,1″-terphenyl]-3′-carboxamide

N′,4-dihydroxy-5′-isopropyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

3″,5″-difluoro-N′,4-dihydroxy-5′-isopropyl-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

5″-chloro-N′,4-dihydroxy-5′-isopropyl-2″-methoxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

4-amino-5′-isopropyl-[1,1′:2′,1″-terphenyl]-3′-carboxamide

3″,5″-difluoro-4-hydroxy-5′-isopropyl-[1,1′:2′,1″-terphenyl]-3′-carboxamide

2-(3-cyanofuran-2-yl)-N′,4′-dihydroxy-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboximidamide

2-(4-cyano-1-methyl-1H-pyrazol-5-yl)-N′,4′-dihydroxy-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboximidamide

2″-cyano-N′,4-dihydroxy-5′-(trifluoromethyl)-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

2-(3-cyano-1-methyl-1H-pyrrol-2-yl)-N′,4′-dihydroxy-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboximidamide

2′-(3-dimethylisoxazol-4-yl)-3′-(hydroxymethyl)-5′-(trifluoromethyl)-[1,1′-biphenyl]-4-ol

5′-cyano-3″,5″-difluoro-N′,4-dihydroxy-[1,1′:2′,1″-terphenyl]-3′-carboximidamide

N′,4′-dihydroxy-2-(pyrrolidin-1-yl)-5-(trifluoromethyl)-[1,1′-biphenyl]-3-carboximidamide

4-chloro-3′,5′-difluoro-N′-hydroxy-6-(1H-indazol-5-yl)-[1,1′-biphenyl]-2-carboximidamide

6-(1H-benzo[d]imidazol-5-yl)-4-chloro-3′,5′-difluoro-N′-hydroxy-[1,1′-biphenyl]-2-carboximidamide

4-chloro-3′,5′-difluoro-N′-hydroxy-6-(1H-indol-5-yl)-[1,1′-biphenyl]-2-carboximidamide

4-chloro-3′,5′-difluoro-6-(1H-indol-5-yl)-[1,1′-biphenyl]-2-carboxamide

4-chloro-3′,5′-difluoro-6-(1H-indazol-5-yl)-[1,1′-biphenyl]-2-carboxamide

6-(1H-benzo[d]imidazol-5-yl)-4-chloro-3′,5′-difluoro-[1,1′-biphenyl]-2-carboxamide

3′,5′-difluoro-N′-hydroxy-6-(1H-indol-5-yl)-4-methyl-[1,1′-biphenyl]-2-carboximidamide

3′,5′-difluoro-N′-hydroxy-6-(1H-indol-6-yl)-4-methyl-[1,1′-biphenyl]-2-carboximidamide

3′,5′-difluoro-N′-hydroxy-6-(1H-indazol-5-yl)-4-methyl-[1,1′-biphenyl]-2-carboximidamide

3′,5′-difluoro-N′-hydroxy-6-(1H-indazol-5-yl)-4-propyl-[1,1′-biphenyl]-2-carboximidamide

3′,5′-difluoro-N′-hydroxy-6-(1H-indol-5-yl)-4-propyl-[1,1′-biphenyl]-2-carboximidamide

3′,5′-difluoro-N′-hydroxy-6-(1H-indazol-5-yl)-4-(trifluoromethyl)-[1,1′-biphenyl]-2-carboximidamide

3′,5′-difluoro-N′-hydroxy-6-(1H-indol-6-yl)-4-(trifluoromethyl)-[1,1′-biphenyl]-2-carboximidamide

3′,5′-difluoro-N′-hydroxy-6-(1H-indazol-6-yl)-4-(trifluoromethyl)-[1,1′-biphenyl]-2-carboximidamide

3′,5′-difluoro-N′-hydroxy-6-(1H-indol-5-yl)-4-(trifluoromethyl)-[1,1′-biphenyl]-2-carboximidamide

3′,5′-difluoro-6-(1H-indol-5-yl)-4-(trifluoromethyl)-[1,1′-biphenyl]-2-carboxamide

3′,5′-difluoro-N′-hydroxy-6-(1H-indazol-6-yl)-4-propyl-[1,1′-biphenyl]-2-carboximidamide

N′-hydroxy-6-(1H-indazol-5-yl)-2′-methoxy-5′-methyl-4-(trifluoromethyl)-[1,1′-biphenyl]-2-carboximidamide

5′-chloro-N′-hydroxy-6-(1H-indol-5-yl)-2′-methoxy-4-(trifluoromethyl)-[1,1′-biphenyl]-2-carboximidamide

5′-chloro-N′-hydroxy-6-(1H-indazol-5-yl)-2′-methoxy-4-(trifluoromethyl)-[1,1′-biphenyl]-2-carboximidamide

2′,5′-difluoro-N′-hydroxy-6-(1H-indazol-5-yl)-4-(trifluoromethyl)-[1,1′-biphenyl]-2-carboximidamide

3′,5′-difluoro-6-(6-fluoro-1H-indol-5-yl)-N′-hydroxy-4-(trifluoromethyl)-[1,1′-biphenyl]-2-carboximidamide

N′-hydroxy-3-(1H-indazol-5-yl)-2-(naphthalen-1-yl)-5-(trifluoromethyl)benzimidamide

2-(benzo[d][1,3]dioxol-4-yl)-N′-hydroxy-3-(1H-indazol-5-yl)-5-(trifluoromethyl)benzimidamide

4′-fluoro-N′-hydroxy-6-(1H-indazol-5-yl)-2′-methoxy-4-(trifluoromethyl)-[1,1′-biphenyl]-2-carboximidamide

N′-hydroxy-6-(1H-indazol-5-yl)-3′-methyl-4-(trifluoromethyl)-[1,1′-biphenyl]-2-carboximidamide

3′,4′,5′-trifluoro-N′-hydroxy-6-(1H-indazol-5-yl)-4-(trifluoromethyl)-[1,1′-biphenyl]-2-carboximidamide

3′,4′-difluoro-N′-hydroxy-6-(1H-indazol-5-yl)-4-(trifluoromethyl)-[1,1′-biphenyl]-2-carboximidamide

N′-hydroxy-3-(1H-indazol-5-yl)-2-(2-methoxypyridin-3-yl)-5-(trifluoromethyl)benzimidamide

2-(cyclopent-1-en-1-yl)-N′-hydroxy-3-(1H-indazol-5-yl)-5-(trifluoromethyl)benzimidamide

2-(3,5-dimethylisoxazol-4-yl)-N′-hydroxy-3-(1H-indazol-5-yl)-5-(trifluoromethyl)benzimidamide

2′,4′-difluoro-N′-hydroxy-6-(1H-indazol-5-yl)-4-(trifluoromethyl)-[1,1′-biphenyl]-2-carboximidamide

or a pharmaceutically acceptable ester, amide, carbamate or salt thereof, including a salt of such an ester, amide or carbamate.

17. The compound as claimed in claim 1 together with a further therapeutic agent, for simultaneous, sequential or separate administration.

18. A pharmaceutical composition which comprises a compound as claimed in claim 1 , together with a pharmaceutically acceptable carrier.

19. A method for modulating estrogen receptor beta activity in a mammal, comprising administering to the mammal a therapeutically effective amount of a compound as claimed in claim 1 .

Assignments (2)
CHANGE OF NAME Recorded Jan 17, 2017
From: KARO BIO AB
To: KARO PHARMA AB
Reel/Frame 041377/0525 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 7, 2014
From: CHENG, AIPING; GARG, NEERAJ; KRÜGER, LARS; LÖFSTEDT, JOAKIM; KOCH, EVA; KOEHLER, KONRAD; HAGBERG, LARS; NÖTEBERG, DANIEL
To: KARO BIO AB
Reel/Frame 032617/0931 →
Priority Claims (1)
GB 1113538.1 · Aug 4, 2011 · national
Continuity (1)
Related Publication 20140323518A1 · Oct 30, 2014