IP Library Granted Patent US 7,687,498
Granted Patent B2
US 7,687,498 · App. 12/041,662 · Granted Mar 30, 2010

Pyridine compounds

Assignee: Synta Pharmaceuticals Corporation
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 7,687,498
App. No.
12/041,662
Granted
Mar 30, 2010
Kind
B2
Abstract

This invention features compounds of formula (I): pharmaceutical compositions of the compounds, and methods of using the compounds for the treatment of, inter alia, IL-12-related diseases and disorders.

Claims (129)

1. A method of treating an inflammatory disorder in a subject in need of such treatment, the method comprising administering to the subject an effective amount of a compound of formula (I):

or a pharmaceutically acceptable salt thereof wherein,

R 2 and R 4 are, independently, H, an optionally substituted alkyl, an optionally substituted alkylcarbonyl, —OR k , —SR k , —NR h R j , hydroxylalkyl, —C(O)R c , —OC(O)R c , —SC(O)R c , —NR k C(O)R c , —C(S)R c , —OC(S)R c , —SC(S)R c , —NR k C(S)R c , —C(NR)R c , —OC(NR)R c , —SC(NR)R c , —NR k C(NR)R c , —SO 2 R c , —S(O)R c , —NR k SO 2 R c , —OS(O) 2 R c , —OP(O)R c R c , —P(O)R c R c , halo, haloalkyl, aminoalkyl, mercaptoalkyl, cyano, nitro, nitroso, azide, an optionally substituted alkylcarbonylalkyl, an optionally substituted cyclyl, an optionally substituted cycloalkyl, an optionally substituted heterocyclyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted aralkyl, an optionally substituted heteroaryl, an optionally substituted heteroaralkyl, or isothionitro; or R 2 and R 4 taken together are ═O, ═S, or ═NR;

R 3 is an optionally substituted cyclyl, an optionally substituted cycloalkyl, an optionally substituted heterocyclyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, or an optionally substituted heteroaryl;

R 5 is —H, alkyl, alkylcarbonyl, halo, nitro, nitroso, cyano, azido, isothionitro, —OR p or —SR p ; and R p is —H, alkyl, or alkylcarbonyl;

n, for each occurrence, is independently 0, 1, 2, 3, 4, 5, 6 or 7;

X is NH;

Y is O;

Z is N;

W is O;

G is absent; and

one of Q, U and V is N, and the other two are each CR g and each CR g may be the same or different;

wherein:

R, for each occurrence, is independently H, an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted cyclyl, an optionally substituted heterocycloalkyl, an optionally substituted heterocyclyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, an optionally substituted heteroaralkyl, —C(O)R c , —OR k , —SR k , —NR h R j , hydroxylalkyl, nitro, cyano, haloalkyl, aminoalkyl, or —S(O) 2 R c ;

R a is H and R b is optionally substituted aryl;

R c is H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cyclyl, an optionally substituted cycloalkyl, an optionally substituted heterocyclyl, an optionally substituted heterocycloalkyl, an optionally substituted aralkyl, an optionally substituted heteroaralkyl, an optionally substituted aryl, an optionally substituted heteroaryl, haloalkyl, —OR k , —SR k , —NR h R j , hydroxylalkyl, alkylcarbonylalkyl, mercaptoalkyl, aminoalkyl, sulfonylalkyl, sulfonylaryl, or thioalkoxy;

R g for each occurrence, is independently, H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cyclyl, an optionally substituted cycloalkyl, an optionally substituted heterocyclyl, an optionally substituted heterocycloalkyl, an optionally substituted aralkyl, an optionally substituted heteroaralkyl, an optionally substituted aryl, an optionally substituted heteroaryl, haloalkyl, —OR k , —SR k , —NR h R j , hydroxylalkyl, alkylcarbonylalkyl, mercaptoalkyl, aminoalkyl, sulfonylalkyl, sulfonylaryl, thioalkoxy, —C(O)R c , —OC(O)R c , —SC(O)R c , —NR k C(O)R c , —C(S)R c , —OC(S)R c , —SC(S)R c , —NR k C(S)R c , —C(NR)R c , —OC(NR)R c , —SC(NR)R c , —NR k C(NR)R c , —SO 2 R c , —S(O)R c , —NR k SO 2 R c , —OS(O) 2 R c , —OP(O)R c R c , —P(O)R c R c , halo, aminoalkyl, mercaptoalkyl, cyano, nitro, nitroso, or azide;

R h and R j , for each occurrence, are independently H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cyclyl, an optionally substituted cycloalkyl, an optionally substituted heterocyclyl, an optionally substituted heterocycloalkyl, an optionally substituted aralkyl, an optionally substituted heteroaralkyl, an optionally substituted aryl, an optionally substituted heteroaryl; or R h and R j taken together with the N to which they are attached is an optionally substituted heterocyclyl, an optionally substituted heterocycloalkyl, or an optionally substituted heteroaryl; and

R k , for each occurrence, is independently H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cyclyl, an optionally substituted cycloalkyl, an optionally substituted heterocyclyl, an optionally substituted heterocycloalkyl, an optionally substituted aralkyl, an optionally substituted heteroaralkyl, an optionally substituted aryl, or an optionally substituted heteroaryl;

wherein the inflammatory disorder is arthritis or Crohn's disease.

2. The method of claim 1 , wherein one of Q, U and V is N, and the other two are CR g , wherein each R g is, independently selected from the group consisting of H, F, Cl, CN, a lower alkyl, a lower haloalkyl, a lower alkoxy, a lower haloalkoxy, a lower alkylamino, a lower dialkylamino, a lower aminoalkyl, and —NH 2 .

3. The method of claim 2 , wherein one of Q, U and V is N, and the other two are independently selected from the group consisting of CH, CF, C(CN), CCI, C(CH 3 ), C(OCH 3 ), C(OCF 3 ), and C(CF 3 ).

4. The method of claim 2 , wherein one of Q, U and V is N, and the other two are independently selected from the group consisting of CH and CF.

5. The method of claim 2 , wherein U is N and Q and V each are CH.

6. The method of claim 2 , wherein R 3 is optionally substituted aryl or optionally substituted heteroaryl.

7. The method of claim 6 , wherein R 3 is an optionally substituted phenyl, an optionally substituted naphthyl, an optionally substituted anthracenyl, an optionally substituted fluorenyl, an optionally substituted indenyl, an optionally substituted azulenyl, an optionally substituted pyridyl, an optionally substituted 1-oxo-pyridyl, an optionally substituted furanyl, an optionally substituted benzo[1,3] dioxolyl, an optionally substituted benzo[1,4] dioxinyl, an optionally substituted thienyl, an optionally substituted pyrrolyl, an optionally substituted oxazolyl, an optionally substituted imidazolyl, an optionally substituted thiazolyl, an optionally substituted isoxazolyl, an optionally substituted quinolinyl, an optionally substituted pyrazolyl, an optionally substituted isothiazolyl, an optionally substituted pyridazinyl, an optionally substituted pyrimidinyl, an optionally substituted pyrazinyl, an optionally substituted triazinyl, an optionally substituted triazolyl, an optionally substituted thiadiazolyl, an optionally substituted isoquinolinyl, an optionally substituted indazolyl, an optionally substituted benzoxazolyl, an optionally substituted benzofuryl, an optionally substituted indolizinyl, an optionally substituted imidazopyridyl, an optionally substituted tetrazolyl, an optionally substituted benzimidazolyl, an optionally substituted benzothiazolyl, an optionally substituted benzothiadiazolyl, an optionally substituted benzoxadiazolyl, an optionally substituted indolyl, an optionally substituted tetrahydroindolyl, an optionally substituted azaindolyl, an optionally substituted indazolyl, an optionally substituted imidazopyridyl, an optionally substituted quinazolinyl, an optionally substituted purinyl, an optionally substituted pyrrolo[2,3] pyrimidinyl, an optionally substituted pyrazolo[3,4] pyrimidinyl, or an optionally substituted benzo(b)thienyl.

8. The method of claim 2 , wherein R 3 is an optionally substituted heterocycloalkyl.

9. The method of claim 8 , wherein R 3 is an optionally substituted piperidinyl, an optionally substituted piperazinyl, an optionally substituted 2- oxopiperazinyl, an optionally substituted 2-oxopiperidinyl, an optionally substituted 2-oxopyrrolidinyl, an optionally substituted 4-piperidonyl, an optionally substituted tetrahydropyranyl, an optionally substituted oxazolidinyl, an optionally substituted 2-oxo-oxazolidinyl, an optionally substituted tetrahydrothiopyranyl, an optionally substituted tetrahydrothiopyranyl sulfone, an optionally substituted morpholinyl, an optionally substituted thiomorpholinyl, an optionally substituted thiomorpholinyl sulfoxide, an optionally substituted thiomorpholinyl sulfone, an optionally substituted 1,3-dioxolanyl,, an optionally substituted [1 ,4] dioxanyl, an optionally substituted 2-oxo-imidazolidinyl, tetrahydrofuranyl, or an optionally substituted tetrahydrothienyl.

10. The method of claim 2 , wherein R 3 is

wherein

each of A and A′, independently, is O, S, NH or NR y , wherein R y is lower alkyl;

each of R e and R e′ , independently is H, optionally substituted alkyl, substituted aryl, or substituted heteroaryl; and

m is 1 or 2.

11. The method of claim 1 , wherein R b is

wherein

R q is H, halogen, CN, optionally substituted alkyl, optionally substituted cyclyl, optionally substituted alkyloxy, optionally substituted alkylcarbonyl, optionally substituted alkyloxycarbonyl, optionally substituted aryloxycarbonyl, optionally substituted heteroaryloxycarbonyl, hydroxyalkyl, alkylamino, or alkylaminocarbonyl;

each R r is, independently, H, halogen, NO 2 , CN, optionally substituted alkyl, optionally substituted aryl, optionally substituted heteroaryl, OR k , OC(O)R k , SO 2 R k , S(O)R k , S(O 2 )NR h R j , SR k , NR h R j , NR k COR k , NR k C(O)OR k , NR k C(O)NR h R j , NR k SO 2 R k , COR k , C(O)OR k , or C(O)NR h R j ; and

z is 0, 1, 2, 3, or 4.

12. The method of claim 11 , wherein:

R q is H, methyl, ethyl, propyl, cyclopropyl, methoxy, ethoxy, methoxycarbonyl, or halogen;

each R r is, independently, F, Cl, CN, methyl, methoxy, ethoxy, —NH 2 , —NHCH 3 , —N(CH 3 ) 2 , —NHCH 2 CH 3 , —N(CH 2 CH 3 ) 2 , OC(O)CH 3 , OC(O)C 2 H 5 , C(O)OH, C(O)OC 2 H 5 , C(O)NH 2 , NHC(O)CH 3 or S(O 2 )NH 2 ;

R i is H, methyl, ethyl, or acetyl, and

z is 0, 1, or 2.

13. The method of claim 12 , wherein one of Q, U and V is N, and the other two are each CH.

14. The method of claim 13 , wherein U is N, and Q and V are each CH.

15. The method of claim 13 , wherein Q is N, and U and V are each CH.

16. The method of claim 13 , wherein V is N, and Q and U are each CH.

17. The method of claim 12 , wherein n is 0, 1, 2, 3, or 4.

18. The method of claim 12 , wherein R 3 is optionally substituted heteroaryl or optionally substituted heterocyclyl.

19. The method of claim 12 , wherein R 3 is pyridinyl, 1-oxy-pyridinyl, 1H- pyridin-2-one, morpholin-4-yl, 4-methyl-piperazin-1-yl, or 2-oxo-oxazolidin-3-yl.

20. The method of claim 19 , wherein n is 2.

21. The method of claim 1 , wherein the compound of formula (I) is selected from the group consisting of:

N-{2-[2-(3,4-Dimethoxy-phenyl)-ethoxy]-6-morpholin-4-yl-pyridin-4-yl}-N′-(1H-indol-3-ylmethylene)-hydrazine;

N-{6-[2-(3,4-Dimethoxy-phenyl)-ethoxy]-4-morpholin-4-yl-pyridin-2-yl}-N′-(1H-indol-3-ylmethylene)-hydrazine;

N-{4-[2-(3,4-Dimethoxy-phenyl)-ethoxy]-6-morpholin-4-yl-pyridin-2-yl}-N′-(1H-indol-3-ylmethylene)-hydrazine;

N-{4-[2-(3,4-Dimethoxy-phenyl)-ethoxy]-6-morpholin-4-yl-pyridin-2-yl}-N′-(3-methyl-benzylidene)-hydrazine;

N-{2-[2-(3,4-Dimethoxy-phenyl)-ethoxy]-6-morpholin-4-yl-pyridin-4-yl}-N′-(3-methyl-benzylidene)-hydrazine;

N-{6-[2-(3,4-Dimethoxy-phenyl)-ethoxy]-4-morpholin-4-yl-pyridin-2-yl}-N′-(3-methyl-benzylidene)-hydrazine;

3-(2-{2-[N′-(3-methyl-benzylidene)-hydrazino]-6-morpholin-4-yl-pyridin-4-yloxy}-ethyl)oxazolidin-2-one;

N-[3,5-Difluoro-4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-N′-(3-methyl-benzylidene)-hydrazine;

N-[3,5-Difluoro-2-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-4-yl]-N′-(3-methyl-benzylidene)-hydrazine;

N-(3-methyl-benzylidene)-N′-[4-morpholin-4-yl-6-(2-morpholoine-4-yl-ethoxy)pyridine-2-yl]-hydrazine;

N-(1H-Indol-3-ylmethylene)-N′-[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazine;

N-Methyl-N′(3-methyl-benzylidene)-N-[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazine;

3-(2-{2-[N′-(3-Methyl-benzylidene)-hydrazino]-6-morpholin-4-yl-pyridin-4-yloxy}-ethyl)-oxazolidin-2-one;

N-Furan-3-ylmethylene-N′-[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazine;

4-Methyl-2-{[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazonomethyl}-phenylamine;

N-(3-Methyl-benzylidene)-N′-{4-morpholin-4-yl-6-[2-(4-oxy-morpholin-4-yl)-ethoxy]-pyridin-2-yl}-hydrazine;

Dimethyl-(3-{[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazonomethyl}-phenyl)-amine;

N-(3-Cyclopropyl-benzylidene)-N′-[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazine;

N-(3-Fluoro-benzylidene)-N′-[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazine;

N-(3-Chloro-benzylidene)-N′-[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazine;

N-(3-Bromo-benzylidene)-N′-[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazine;

N-(3-Iodo-benzylidene)-N′-[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazine;

N-(3,4-Dimethyl-benzylidene)-N′-[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazine;

N-(2,5-Dimethyl-benzylidene)-N′-[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazine;

4-Methyl-2-{[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazonomethyl}-phenol;

4-Methyl-2-{[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazonomethyl}-phenylamine;

Methyl-(4-methyl-2-{[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazonomethyl}-phenyl)-amine;

Dimethyl-(4-methyl-2-{[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazonomethyl}-phenyl)-amine;

N-Methyl-N-(4-methyl-2-{[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazonomethyl}-phenyl)-acetamide;

N-Ethyl-N′-(3-methyl-benzylidene)-N-[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazine;

3-{[4-Morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazonomethyl}-benzoic acid methyl ester;

3-{[4-Morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazonomethyl}-benzoic acid ethyl ester;

3-{[4-Morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazonomethyl}-benzoic acid isopropyl ester;

3-{[4-Morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazonomethyl}-benzoic acid;

3-{[4-Morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazonomethyl}-benzamide;

N-Methyl-3-{[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazonomethyl}-benzamide;

N-Cyclopropyl-3-{[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazonomethyl}-benzamide;

3-Methyl-5-{[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazonomethyl}-benzamide;

3-Hydroxymethyl-5-{[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazonomethyl}-benzamide;

N-(3-Methyl-benzylidene)-N′-[5-methyl-4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazine;

N-[5-Fluoro-4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-N′-(3-methyl-benzylidene)-hydrazine;

N-[5-Chloro-4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-N′-(3-methyl-benzylidene)-hydrazine;

N-Benzylidene-N′-[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazine;

N-(3-Methyl-benzylidene)-N′-{6-[2-(4-methyl-piperazin-1-yl)-ethoxy]-4-morpholin-4-yl-pyridin-2-yl}-hydrazine;

N-(3-Methyl-benzylidene)-N′-[4-morpholin-4-yl-6-(2-piperazin-1-yl-ethoxy)-pyridin-2-yl]-hydrazine;

1-[4-(2-{6-[N′-(3-Methyl-benzylidene)-hydrazino]-4-morpholin-4-yl-pyridin-2-yloxy}-ethyl)-piperazin-1-yl]-ethanone;

N-{6-[2-(4-Ethyl-piperazin-1-yl)-ethoxy]-4-morpholin-4-yl-pyridin-2-yl}-N′-(3-methyl-benzylidene)-hydrazine;

N-{6-[2-(4-Ethyl-3-methyl-piperazin-1-yl)-ethoxy]-4-morpholin-4-yl-pyridin-2-yl}-N′-(3-methyl-benzylidene)-hydrazine;

N-{6-[2-(4-Ethyl-2-methyl-piperazin-1-yl)-ethoxy]-4-morpholin-4-yl-pyridin-2-yl}-N′-(3-methyl-benzylidene)-hydrazine;

N-{6-[2-(2,6-Dimethyl-morpholin-4-yl)-ethoxy]-4-morpholin-4-yl-pyridin-2-yl}-N′-(3-methyl-benzylidene)-hydrazine;

N-(3-Methyl-benzylidene)-N′-[4-morpholin-4-yl-6-(2-piperidin-1-yl-ethoxy)-pyridin-2-yl]-hydrazine;

N-(3-Methyl-benzylidene)-N′-[4-morpholin-4-yl-6-(2-pyrrolidin-1-yl-ethoxy)-pyridin-2-yl]-hydrazine;

1-(2-{6-[N′-(3-Methyl-benzylidene)-hydrazino]-4-morpholin-4-yl-pyridin-2-yloxy}-ethyl)-pyrrolidin-2-one;

1-(2-{6-[N′-(3-Methyl-benzylidene)-hydrazino]-4-morpholin-4-yl-pyridin-2-yloxy}-ethyl)-pyrrolidine-2,5-dione;

1-(2-{6-[N′-(3-Methyl-benzylidene)-hydrazino]-4-morpholin-4-yl-pyridin-2-yloxy}-ethyl)-imidazolidine-2-thione;

1-Methyl-3-(2-{6-[N′-(3-methyl-benzylidene)-hydrazino]-4-morpholin-4-yl-pyridin-2-yloxy}-ethyl)-imidazolidine-2-thione;

1-(2-{6-[N′-(3-Methyl-benzylidene)-hydrazino]-4-morpholin-4-yl-pyridin-2-yloxy}-ethyl)-pyrrolidin-2-one;

N-[6-(2-[1 ,3]Dioxolan-2-yl-ethoxy)-4-morpholin-4-yl-pyridin-2-yl]-N′-(3-methyl-benzylidene)-hydrazine;

Dimethylamino-acetic acid 3-{6-[N′-(3-methyl-benzylidene)-hydrazino]-4- morpholin-4-yl-pyridin-2-yl}-propyl ester;

N-(3-Methyl-benzylidene)-N′-[4-morpholin-4-yl-6-(2-pyrazin-2-yl-ethoxy)-pyridin-2-yl]-hydrazine;

N-(3-Methyl-benzylidene)-N′-[4-morpholin-4-yl-6-(2-thiophen-2-yl-ethoxy)-pyridin-2-yl]-hydrazine;

N-(3-Methyl-benzylidene)-N′-[4-morpholin-4-yl-6-(2-thiazol-5-yl-ethoxy)-pyridin-2-yl]-hydrazine;

N-(3-Methyl-benzylidene)-N′-[4-morpholin-4-yl-6-(2-thiazol-2-yl-ethoxy)-pyridin-2-yl]-hydrazine;

N-(3-Methyl-benzylidene)-N′-{6-[2-(2-methyl-thiazol-5-yl)-ethoxy]-4-morpholin-4-yl-pyridin-2-yl}-hydrazine;

N-(3-Methyl-benzylidene)-N′-{6-[2-(2-methyl-oxazol-5-yl)-ethoxy]-4-morpholin-4-yl-pyridin-2-yl}-hydrazine;

N-(3-Methyl-benzylidene)-N′-{6-[2-(2-methyl-3H-imidazol-4-yl)-ethoxy]-4-morpholin-4-yl-pyridin-2-yl}-hydrazine;

N-{6-[2-(2,3-Dimethyl-3H-imidazol-4-yl)-ethoxy]-4-morpholin-4-yl-pyridin-2-yl}-N′-(3-methyl-benzylidene)-hydrazine;

N-[6-(2-Imidazo[1 ,2-a]pyridin-3-yl-ethoxy)-4-morpholin-4-yl-pyridin-2-yl]-N′-(3-methyl-benzylidene)-hydrazine;

N-{6-[2-(1 H-Indol-3-yl)-ethoxy]-4-morpholin-4-yl-pyridin-2-yl}-N′-(3-methyl-benzylidene)-hydrazine;

1-[3-(2-{6-[N′-(3-Methyl-benzylidene)-hydrazino]-4-morpholin-4-yl-pyridin-2-yloxy}-ethyl)-indol-1-yl]-ethanone;

1-[3-(2-{6-[N′-(3-Methyl-benzylidene)-hydrazino]-4-morpholin-4-yl-pyridin-2-yloxy}-ethyl)-pyrrolo[3,2-c]pyridin-1-yl]-ethanone;

4-(3-{6-[N′-(3-Methyl-benzylidene)-hydrazino]-4-morpholin-4-yl-pyridin-2-yloxy}-propyl)-benzoic acid methyl ester;

N-(3-Methyl-benzylidene)-N′-{4-morpholin-4-yl-6-[3-(1-oxy-pyridin-2-yl)-propoxy]-pyridin-2-yl}-hydrazine;

N-[4-Morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-N′-naphthalen-2-ylmethylene-hydrazine;

N-Benzofuran-5-ylmethylene-N′-[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazine;

N-Benzo[b]thiophen-5-ylmethylene-N′-[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-hydrazine; and N-(3-Methyl-benzylidene)-N′-[4-morpholin-4-yl-6-(2-morpholin-4-yl-ethoxy)-1-oxy-pyridin-2-yl]-hydrazine;

or a pharmaceutically acceptable salt thereof.

Assignments (1)
CHANGE OF NAME Recorded May 3, 2021
From: SYNTA PHARMACEUTICALS CORP.
To: MADRIGAL PHARMACEUTICALS, INC.
Reel/Frame 056121/0785 →
Continuity (4)
Division 1098569600 · Nov 10, 2004
Provisional Application 6058512400 · Jul 1, 2004
Provisional Application 6051879100 · Nov 10, 2003
Related Publication 20080167300A1 · Jul 10, 2008