IP Library Granted Patent US 7,834,039
Granted Patent B2
US 7,834,039 · App. 12/002,196 · Granted Nov 16, 2010

Oxadiazole compounds

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Quick Facts
Patent No.
US 7,834,039
App. No.
12/002,196
Granted
Nov 16, 2010
Kind
B2
Abstract

Novel oxadiazole compounds, pharmaceutical compositions containing such compounds and the use of those compounds or compositions as agonists or antagonists of the S1P family of G protein-coupled receptors for treating diseases associated with modulation of S1P family receptor activity, in particular by affording a beneficial immunosuppressive effect are disclosed.

Claims (201)

1. A compound of Formula I

pharmaceutically acceptable salts, prodrugs, enantiomers or stereoisomers thereof, wherein

L is a bond;

R 1 is optionally substituted phenyl;

R 2 is Br, Cl, CF 3 , CN, or —O—(C 1 -C 2 )alkyl;

R 3 is optionally substituted—(C 3 -C 8 )alkyl, (C 4 -C 5 )alkenyl, (C 4 -C 5 )alkynyl, —(C 2 -C 3 )alkyl—O—optionally substituted (C 1 -C 3 )alkyl, —(C 1 -C 3 )alkyl-imidazolyl, —(C 1 -C 3 )alkyl-morpholinyl, —(C 1 -C 3 )alkyl-optionally substituted phenyl, —(C 1 -C 3 )alkyl-optionally substituted piperazinyl, —(C 1 -C 3 )alkyl-pyrrolidinyl, —(C 1 -C 3 )alkyl-piperidinyl, or —(C 1 -C 3 )alkyl-thienyl; and

R 6 is H;

wherein R 1 is optionally substituted by one or more substituents independently selected from Br, Cl, F, CF 3 , CN, oxo, optionally substituted (C 1 -C 6 )alkyl, optionally substituted (C 2 -C 6 )alkenyl, optionally substituted amino, optionally substituted (C 3 -C 6 )cycloalkyl, —CH 2 -optionally substituted piperidinyl, —C(O)—optionally substituted (C 1 -C 6 )alkyl, —C(O)—NR—(C 1 -C 6 )alkyl, —C(O)—O-optionally substituted(C 1 -C 6 )alkyl, —O-optionally substituted (C 1 -C 6 )alkyl, —NH—(C 3 -C 6 )cycloalkyl, —NH—C(O)—O—(C 1 -C 3 )alkyl, —S(O) 2 -N(R 9 ) 2 , —S(O) 2 -NH-optionally substituted (C 1 -C 4 )alkyl, —NH-optionally substituted(C 1 -C 6 )alkyl, —NH—C(O)-furanyl, —NH—S(O) 2 -optionally substituted phenyl, optionally substituted pyridinyl,

provided that R 1 is not substituted by optionally substituted cyclohexyl, —C(O)-cyclohexyl or —NH—cyclohexyl;

when L is (C 1 -C 3 )alkyl, R 1 is not optionally substituted isoxazolyl;

when R 3 is optionally substituted (C 1 )alkyl, L-R 1 is not cyclohexyl or —CH 2 -cyclohexyl; and

provided that the compound is not

wherein R is H or (C 1 -C 3 )alkyl; and

wherein each R 9 is independently selected from H or optionally substituted (C 1 -C 6 )alkyl.

2. The compound of claim 1 wherein the compound is a compound of Formula Ia

wherein L is a bond.

3. The compound of claim 2 wherein the compound is

4. A compound having formula (IV):

or a pharmaceutically acceptable salt, prodrug, enantiomer or stereoisomer thereof,

wherein:

X is CR 4 ;

L is a bond;

Y is —O—;

R 1 is optionally substituted phenyl;

R 2 is H, —(C 1 -C 4 )alkyl, —O—(C 1 -C 3 )alkyl, —CF 3 , —CN, halo or —COO—(C 1 -C 4 )alkyl;

R 6 is H;

R 3 is —(CH 2 ) 2 -R 9 ; and when Y is O, R 3 is not alkyldiazeapane, —C(CH 3 ) 2 COOCH 2 CH 3 or —CH 2 CH 2 N(CH 2 CH 3 ) 2 , and when Y is —CH 2 —, R 3 is not —CH 2 COOH;

R 4 is H;

R 5 is H, O—(C 1 -C 3 )alkyl or (C 1 -C 3 )alkyl;

each occurrence of R 7 or R 7 ′ is independently H or optionally substituted (C 1 -C 3 )alkyl;

R 8 is H, optionally substituted CH 3 , or —COR 9 ;

R 9 is hydrogen, optionally substituted (C 1 -C 3 )alkyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl or optionally substituted (C 3 -C 6 )cycloalkyl; and

n is 1, 2, 3 or 4;

wherein each substituent or optional substituent is independently one or more R 10 groups wherein R 10 is optionally substituted alkyl, alkenyl, optionally substituted alkoxy groups, alkoxyalkoxy, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylheterocycloalkoxy, alkyl, alkylamino, alkylcarbonyl, alkylester, alkyl-O—C(O)—, alkyl-heterocyclyl, alkyl-cycloalkyl, alkyl-nitrile, alkylsulfonyl, alkynyl, amido groups, amino, aminoalkyl, aminocarbonyl, carbonitrile, carbonylalkoxy, carboxamido, CF 3 , CN, —C(O)OH, —C(O)H, —C(O)—C(CH 3 ) 3 , —OH, —C(O)O-alkyl, —C(O)O-cycloalkyl, —C(O)O-heterocyclyl, —C(O)-alkyl, —C(O)-cycloalkyl, —C(O)-heterocyclyl, CN, dialkylamino, dialkylaminocarbonylalkoxy, dialkylaminocarbonyl, dialkylaminosulfonyl, —C(O)—OR a , halogen, heterocyclyl, heterocyclylalkyl, heterocyclyloxy, hydroxy, hydroxyalkyl, oxo, phenyl, —SO 2 CH 3 , —SO 2 CF 3 , sulfonyl, tetrazolyl, thienylalkoxy, trifluoromethylcarbonylamino, trifluoromethylsulfonamido, heterocyclylalkoxy, heterocyclyl-S(O) p , cycloalkyl-S(O) p , alkyl-S—, heterocyclyl-S, heterocycloalkyl, heterocycolthio, cycloalkylthio, N-alkylamino and N,N-dialkylamino where R a is alkyl, heterocycloalkyl, or heterocyclyl and p is 1 or 2; provided that

R 1 is not optionally substituted furanyl or —C(O)-optionally substituted furanyl;

R 3 is not optionally substituted quinolinyl;

R 9 is not optionally substituted cyclopropyl, optionally substituted cyclohexyl, optionally substituted furanyl, optionally substituted imidazolyl, optionally substituted indolyl, optionally substituted naphthyl, optionally substituted piperazinyl, optionally substituted pyrazolyl, optionally substituted pyridazinyl or optionally substituted quinolinyl;

R 1 is not substituted by —C(O)-cyclopentyl, optionally substituted cyclopentyl, —C(O)-cyclobutyl, cyclobutyl, —C(O)-cyclohexyl or optionally substituted cyclohexyl;

R 3 is not substituted by C(O)-cyclopropyl;

when R 3 is CH 3 or 4-chlorophenylmethyl, L-R 1 is not cyclopropyl, cyclopentyl, optionally substituted cyclohexyl, —CH 2 -cyclohexyl, —NH-cyclohexyl, —CH 2 CH 2 -cyclohexyl or optionally substituted pyrazolyl;

when Y is O, R 3 is not —(C 0 -C 4 )alkyl-optionally substituted isoxazolyl or optionally substituted pyrazolyl;

when L is (C 1 -C 3 )alkyl, R 1 is not optionally substituted isoxazolyl;

when L is a bond, R 1 is not optionally substituted cyclobutyl, optionally substituted cyclohexyl, optionally substituted naphthyl, —CH 2 -optionally substituted naphthyl, —CH 2 —O-optionally substituted naphthyl, optionally substituted pyrazolyl or tetrahydrobenzofuranyl;

the compound is not

the compound is not

wherein R 3 is optionally substituted piperazinyl or optionally substituted phenyl;

the compound is not

wherein R 1 is optionally substituted pyridine or 3-chlorophenyl and —Y—R 3 is

—NH—C(O)-optionally substituted phenyl;

—O-optionally substituted pyridinyl;

—NH—C(O)—OCH 3 ;

—CH 2 -optionally substituted piperazinyl;

—O-optionally substituted (C 1 -C 9 )alkyl;

—CH 2 -morpholinyl; or

—O—C(O)-optionally substituted pyridinyl;

provided the compound is not

wherein

L is CH 2 , CH(CH 3 ) or CH 2 CH 2 ;

Y is O or CH 2 ;

R 2 is H or OCH 3 ;

R 3 is CH 3 or OCF 3 ; and

R is H or NO 2 ;

provided the compound is not

provided the compound is not

wherein R 1 is phenyl, 4-chlorophenyl, piperidinyl or thienyl.

5. The compound of claim 4 having formula (IVa):

or a physiologically acceptable salt, or stereoisomer thereof, wherein:

L is a bond;

R 1 is optionally substituted phenyl;

R 2 is Cl or CF 3 ; and

R 3 is straight or branched optionally substituted (C 2 -C 8 )alkyl.

6. The compound of claim 5 wherein R 2 is Cl.

7. The compound of claim 4 having formula (IVb):

or a physiologically acceptable salt, prodrug, enantiomer or stereoisomer thereof, wherein:

L is a bond;

R 1 is tolyl, ethanonylphenyl, phenyl carbamic acid tert-butyl ester, benzonitrile, or diethylaminophenyl; and

R 3 is isobutyl, cyclopropylmethyl, 3-methoxypropyl, 1-ethylpropyl, sec-butyl, isopropyl, tertbutyl, or trifluorethyl.

8. The compound of claim 4 having formula (IVc):

or a physiologically acceptable salt, or stereoisomer thereof, wherein:

L is a bond;

R 1 is tolyl, phenyl carbamic acid tert-butyl ester, or benzonitrile; and

R 3 is isobutyl, isopropyl, cyclopropylmethyl, 3-methoxypropyl, 1-ethylpropyl, sec-butyl, or isopropyl.

9. The compound of claim 8 , wherein R 3 is isopropyl.

10. The compound of claim 9 , wherein R 1 is tolyl.

11. A pharmaceutical composition comprising a compound according to claim 1 or a pharmaceutically acceptable salt, prodrug or stereoisomer thereof and a pharmaceutically acceptable diluent or carrier.

12. The compound of claim 1 wherein the compound is

3-[3-chloro-4-(1-ethyl-propoxy)-phenyl]-5-o-tolyl-[1,2,4]oxadiazole;

3-chloro-4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzonitrile;

1-(3-chloro-4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzyl)-3-methylazetidine-3-carboxylic acid;

(1R,3S)-3-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenylamino)cyclopentanecarboxylic acid;

3-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenoxy)propane-1,2-diol;

3-(3-Chloro-4-cyclopropylmethoxy-phenyl)-5-o-tolyl- [1,2,4]oxadiazole;

3-(4-Butoxy-3-chloro-phenyl)-5-o-tolyl-[1,2,4]oxadiazole;

3-[3-Chloro-4-(1-methyl-cyclopropylmethoxy)-phenyl]-5-o-tolyl-[1,2,4]oxadiazole;

3-[3-Chloro-4-(1-methyl-cyclopropylmethoxy)-phenyl]-5-o-tolyl-[1,2,4]oxadiazole;

3-(3-Chloro-4-pentyloxy-phenyl)-5-o-tolyl-[1,2,4]oxadiazole;

3-[3-Chloro-4-(3,3-dimethyl-butoxy)-phenyl]-5-o-tolyl-[1,2,4]oxadiazole;

3-[3-Chloro-4-(3,3-dimethyl-butoxy)-phenyl]-5-o-tolyl-[1,2,4]oxadiazole;

3-[3-Chloro-4-(2-ethyl-butoxy)-phenyl]-5-o-tolyl-[1,2,4]oxadiazole;

3-(3-Chloro-4-octyloxy-phenyl)-5-o-tolyl-[1,2,4]oxadiazole;

3-[3-Chloro-4-(3-methoxy-propoxy)-phenyl]-5-o-tolyl-[1,2,4]oxadiazole;

3-[3-Chloro-4-(3-ethoxy-propoxy)-phenyl]-5-o-tolyl-[1,2,4]oxadiazole;

1- {2-[2-Chloro-4-(5-o-tolyl-[1,2,4]oxadiazol-3-yl)-phenoxy]-ethyl} -piperidine;

4- {2-[2-Chloro-4-(5-o-tolyl-[1,2,4]oxadiazol-3-yl)-phenoxy]ethyl} -morpholine;

3-[3-Chloro-4-(1-ethyl-propoxy)-phenyl]-5-o-tolyl-[1,2,4]oxadiazole;

3-[3-Chloro-4-(3-methyl-butoxy)-phenyl]-5-o-tolyl-[1,2,4]oxadiazole;

3-[3-Chloro-4-(2-isopropoxy-ethoxy)-phenyl]-5-o-tolyl-[1,2,4]oxadiazole;

3-(3-Chloro-4-pent-3-ynyloxy-phenyl)-5-o-tolyl-[1,2,4]oxadiazole;

3-(4-sec-Butoxy-3-chloro-phenyl)-5-o-tolyl-[1,2,4]oxadiazole;

{2-[2-Chloro-4-(5-o-tolyl-[1,2,4]oxadiazol-3-yl)-phenoxy]propyl} dimethylamine;

{2-[2-Chloro-4-(5-o-tolyl-[1,2,4]oxadiazol-3-yl)-phenoxy]ethyl} dimethylamine;

3- {4-[-But-2-enyl)oxy]-3-chloro-phenyl} -5-o-tolyl-[1,2,4]oxadiazole;

3-[3-Chloro-4-(4,4,4-trifluoro-butoxy)-phenyl]-5-o-tolyl-[1,2,4]oxadiazole;

3-(3-Chloro-4-isopropoxy-phenyl)-5-o-tolyl-[1,2,4]oxadiazole;

3,5-Bis-(3-chloro-4-isopropoxy-phenyl)-[1,2,4]oxadiazole;

3-(3-Chloro-4-isopropoxy-phenyl)-5-phenyl-[1,2,4]oxadiazole;

3-(3-Chloro-4-isopropoxy-phenyl)-5-(3-trifluoromethyl-phenyl)-[1,2,4]oxadiazole;

1- {4-[3-(3-Chloro-4-isopropoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-phenyl} ethanone;

{4-[3-(3-Chloro-4-isopropoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-phenyl} diethyl-amine;

{4-[3-(3-Chloro-4-isopropoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-phenyl} carbamic acid tert-butyl ester;

3[3-(3-Chloro-4-isopropoxy-phenyl)[1,2,4]oxadiazol-5-yl]benzonitrile;

3[3-(3-Chloro-4-isopropoxy-phenyl)[1,2,4]oxadiazol-5-yl]benzonitrile;

{3-[3-(3-Chloro-4-isopropoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-phenyl} dimethylamine;

3-(3-Chloro-4-isopropoxy-phenyl)-5-(3-chloro-phenyl)-[1,2,4]oxadiazole;

3-(3-Chloro-4-isopropoxy-5-methoxy-phenyl)-5-phenyl-[1,2,4]oxadiazole;

3-(4-Methoxy-3-trifluoromethyl-phenyl)-5-o-tolyl-[1,2,4]oxadiazole;

3-(3-Chloro-4-isopropoxy-phenyl)-5-(2,4-dichloro-phenyl)-[1,2,4]oxadiazole;

3-Chloro-4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl aniline;

1-(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)cyclopropanecarbonitrile;

4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzenesulfonamide;

(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)methanol;

1-(4-(3-(3-Bromo-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)-3-chlorobenzyl)azetidine-3-carboxylic acid;

1-(3-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzyl)azetidine-3-carboxylic acid;

1-(3-chloro-4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzyl)azetidine-3-carboxylic acid;

1 -(4-(3-(4-Isopropoxy-3 -(trifluoromethyl)phenyl)- 1 ,2,4-oxadiazol-5-yl)benzyl)azetidine-3 -carboxylic acid;

1-(4-(3-(3-Ethoxy-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzyl)azetidine-3-carboxylic acid;

3-(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzylamino)propanoic acid;

1-(4-(3-(4-Isopropoxy-3-methoxyphenyl)-1,2,4-oxadiazol-5-yl)benzyl)azetidine-3-carboxylic acid;

1-(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)-3-methoxybenzyl)azetidine-3-carboxylic acid;

2-(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzylamino)acetic acid;

1-(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzyl)piperidine-4-carboxylic acid;

1-(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzylamino)cyclopropanecarboxylic acid;

1 -(4-Chloro-3 -(3 -(3 -chloro-4-isopropoxyphenyl)- 1,2,4-oxadiazol-5-yl)benzyl)azetidine-3 -carboxylic acid acetate salt;

2-(3-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzylamino)acetic acid;

1 -(4-(3 -(4-Isopropoxy-3 -(trifluoromethyl)phenyl)- 1 ,2,4-oxadiazol-5-yl)benzyl)azetidine-3 -carboxylic acid;

(1S,3R)-3-(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenylamino)cyclopentanecarboxylic acid;

(R)-3-(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenoxy)propane-1,2-diol;

2((4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenoxy)methyl)propane-1,3-diol;

Chloro-4-(3-(3-chloro-4-isopropoxyphenyl)- 1 ,2,4-oxadiazol-5-yl)phenoxy)propane- 1 ,2-diol;

4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzonitrile;

4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzaldehyde;

1-(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzyl)azetidine-3-carboxylic acid;

3-(3-Chloro-4-isopropoxyphenyl)-5-(4-fluorophenyl)-1,2,4-oxadiazole;

3-Chloro-4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzonitrile;

2-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)propan-2-amine;

Methyl 3-(2-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)propan-2-ylamino)propanoate;

3-(2-(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)propan-2-ylamino)propanoic acid;

(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)methanol;

5-(4-(Azidomethyl)phenyl)-3-(3-chloro-4-isopropoxyphenyl)- 1,2,4-oxadiazole;

(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)methanamine;

(R)-3-(3-Chloro-4-isopropoxyphenyl)-5-(4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-1,2,4-oxadiazole;

(S)-3-(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenoxy)propane-1,2-diol;

4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzenesulfonamide;

Tert-butyl 3,3′-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenylsulfonylazanediyl)dipropanoate;

Tert-butyl 3-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenylsulfonamido)propanoate;

3-(4-(3-(3-cChloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenylsulfonamido)propanoic acid;

2,2′(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenylsulfonylazanediyl)diacetic acid;

Tert-butyl 2,2′-(4-(3-(3-chloro-4-isopropoxyphenyl)- 1,2,4-oxadiazol-5-yl)phenylsulfonylazanediyl)diacetate;

Tert-butyl 2-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenylsulfonamido)acetate;

2-(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenylsulfonamido)acetic acid;

3-(3-Chloro-4-isopropoxyphenyl)-5-(4((2,2-dimethyl -1,3-dioxolan-4-yl)methoxy)phenyl)-1,2,4-oxadiazole;

2-(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenoxy)acetic acid;

4-(3-(3-Bromo-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzonitrile;

4-(3-(3-Bromo-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzaldehyde;

3-(3-Bromo-4-isopropoxyphenyl)-5-(4-(dimethoxymethyl)phenyl)-1,2,4-oxadiazole;

5-(5-(4-(Dimethoxymethyl)phenyl)-1,2,4-oxadiazol-3-yl)-2-isopropoxybenzonitrile;

5-(5-(4-Formylphenyl)-1,2,4-oxadiazol-3-yl)-2-isopropoxybenzonitrile;

1-(4-(3-(3-Cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzyl)azetidine-3-carboxylic acid;

1-(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)cyclopropanecarbonitrile;

1-(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)cyclopropanecarbaldehyde;

3-((1-(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)cyclopropyl)methylamino)propanoic acid;

N-(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzyl)-1-(2,2-dimethyl-1,3-dioxolan-4-yl )methanamine;

3-(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzylamino)propane-1,2-diol;

(Z)-Methyl 3-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)acrylate;

Trans-methyl 2-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)cyclopropanecarboxylate;

Trans-2-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)cyclopropanecarboxylic acid;

(Z)-Methyl 3-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)acrylate;

(Z)-3-(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)acrylic acid;

3-Chloro-4-(3-(3-chloro-4-isopropoxyphenyl)- 1,2,4-oxadiazol-5-yl)aniline;

3-(3-Chloro-4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenylamino)cyclobutanecarboxylic acid;

4-(3-(3-Chloro-4-isopropoxyphenyl)- 1,2,4-oxadiazol-5-yl)aniline;

3-(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenylamino)cyclobutanecarboxylic acid;

2-(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)propan-2-amine;

Methyl 3-(2-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)propan-2-ylamino)propanoate; or 3-(2-(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)propan-2-ylamino)propanoic acid.

13. The compound of claim 4 wherein the compound is 3-(3-Chloro-4-cyclopropylmethoxy-phenyl)-5-o-tolyl-[1,2,4]oxadiazole;

3-(3-Chloro-4-cyclopentyloxy-phenyl)-5-o-tolyl-[1,2,4]oxadiazole;

3-(3-Chloro-4-cyclohexyloxy-phenyl)-5-o-tolyl-[1,2,4]oxadiazole;

3-(3-Chloro-4-phenethyloxy-phenyl)-5-o-tolyl-[1,2,4]oxadiazole;

3-(3-Chloro-4-cyclohexylmethoxy-phenyl)-5-o-tolyl-[1,2,4]oxadiazole;

3-[3-Chloro-4-(2-thiophen-2-yl-ethoxy)-phenyl]-5-o-tolyl-[1,2,4]oxadiazole;

3-(3-Chloro-4-cyclobutylmethoxy-phenyl)-5-o-tolyl-[1,2,4]oxadiazole; or 3-[3-Chloro-4-(4-methyl-cyclohexylmethoxy)-phenyl]-5-o-tolyl-[1,2,4]oxadiazole.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 17, 2013
From: ABBOTT LABORATORIES
To: ABBVIE INC.
Reel/Frame 030235/0856 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 3, 2010
From: WOLLER, KEVIN R.; GRONGSAARD, PINTIPA
To: ABBOTT LABORATORIES
Reel/Frame 024480/0196 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 28, 2008
From: ANSELL, GRAHAM K.
To: ABBOTT LABORATORIES
Reel/Frame 020880/0017 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 28, 2008
From: HOBSON, ADRIAN D.; FIX-STENZEL, SHANNON R.; CUSACK, KEVIN P.; BREINLINGER, ERIC C.; STOFFEL, ROBERT H.
To: ABBOTT LABORATORIES
Reel/Frame 020880/0027 →