US5382598A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Therapeutic amides
Assignee: Imperial Chemical Industries Ltd
•
Filing: 1993-09-24
•
Granted: 1995-01-17
•
Expires: 2013-09-24
Abstract
Abstract Amides having formula I: <IMAGE> (I) wherein E, X, R2 and R3 have the meanings given in the specification, and pharmaceutically acceptable salts and pharmaceutically acceptable in vivo hydrolyzable esters thereof, which are useful in the treatment of urinary incontinence. Further provided are processes for preparing the amides and pharmaceutical compositions containing them.
Inventors
- 👤 Russell Keith
- 👤 Cyrus J. Ohnmacht
- 👤 Keith H. Gibson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 20:22
CPC Classifications
C; C07; C07C; C07C317/00; C07C317/26; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/62; C07D213/70; A; A61; A61K; A61K31/00; A61K31/33; A61K31/38; A61P; A61P13/00; A61P13/02; A61P15/00; C07C235/00; C07C235/02; C07C235/04; C07C235/16; C07C317/32; C07C317/34; C07C317/38; C07C317/40; C07C317/44; C07C317/48; C07C317/50; C07D213/24; C07D213/44; C07D213/46; C07D213/50; C07D213/72; C07D213/75; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/32; C07D239/38; C07D241/00; C07D241/02; C07D241/10; C07D241/14; C07D241/18; C07D277/00; C07D277/02; C07D277/20; C07D277/32; C07D277/36; C07D333/00; C07D333/02; C07D333/04; C07D333/26; C07D333/30; C07D333/34; C07C2601/00; C07C2601/06; C07C2601/08
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
268 words
An amide of the following formula I, wherein: E is CZ wherein C is a ring carbon and Z is a substituent defined below, wherein: X and Z are selected from the group consisting of: (A) X is ArY wherein Y is a linking group selected from carbonyl, sulfinyl, and sulfonyl and Ar is selected from the group consisting of: phenyl substituted with 0-2 substituents selected from halo, hydroxy, cyano, (1-4C)alkyl, and (1-4C)alkoxy, provided that the 4-position of said phenyl may be substituted by fluoro only, and that the said phenyl may not be 3,5-disubstituted; provided that Ar is not 3-chlorophenyl, 3-bromophenyl, 3-iodophenyl or 3-(1-4C)alkylphenyl when Y is carbonyl; and Z is selected from hydrogen, cyano, halo, hydroxy, (1-4C)alkyl, and (1-4C)alkoxy; (B) X is cyano and Z is selected from the group consisting of phenylthio, phenylsulfinyl, and phenylsulfonyl the phenyl rings of which are substituted with 0-2 substituents selected from halo, hydroxy, cyano, nitro (1-4C)alkyl, and (1-4)alkoxy; R 2 and R 3 are independently selected from the group consisting of (1-3C)alkyl substituted by from 0 to 2k+1 groups selected from fluoro and chloro wherein k is the number of carbon atoms in the said (1-3C)alkyl, provided that R 2 and R 3 are not both methyl; or together, with the carbon atom to which both R 2 and R 3 are attached, form a 3-5 membered cycloalkyl ring optionally substituted by from 0 to 2m-2 fluoro groups wherein m is the number of carbon atoms in said ring; and pharmaceutically acceptable in vivo hydrolyzable esters of said amide; and pharmaceutically acceptable salts of said amide and said esters.
Claim 2
Dependent Claim
268 words
An amide of the following formula I, wherein: E is CZ wherein C is a ring carbon and Z is a substituent defined below, wherein: X and Z are selected from the group consisting of: (A) X is ArY wherein Y is a linking group selected from carbonyl, sulfinyl, and sulfonyl and Ar is selected from the group consisting of: phenyl substituted with 0-2 substituents selected from halo, hydroxy, cyano, (1-4C)alkyl, and (1-4C)alkoxy, provided that the 4-position of said phenyl may be substituted by fluoro only, and that the said phenyl may not be 3,5-disubstituted; provided that Ar is not 3-chlorophenyl, 3-bromophenyl, 3-iodophenyl or 3-(1-4C)alkylphenyl when Y is carbonyl; and Z is selected from hydrogen, cyano, halo, hydroxy, (1-4C)alkyl, and (1-4C)alkoxy; (B) X is cyano and Z is selected from the group consisting of phenylthio, phenylsulfinyl, and phenylsulfonyl the phenyl rings of which are substituted with 0-2 substituents selected from halo, hydroxy, cyano, nitro (1-4C)alkyl, and (1-4)alkoxy; R 2 and R 3 are independently selected from the group consisting of (1-3C)alkyl substituted by from 0 to 2k+1 groups selected from fluoro and chloro wherein k is the number of carbon atoms in the said (1-3C)alkyl, provided that R 2 and R 3 are not both methyl; or together, with the carbon atom to which both R 2 and R 3 are attached, form a 3-5 membered cycloalkyl ring optionally substituted by from 0 to 2m-2 fluoro groups wherein m is the number of carbon atoms in said ring; and pharmaceutically acceptable in vivo hydrolyzable esters of said amide; and pharmaceutically acceptable salts of said amide and said esters.
Claim 3
Dependent Claim
178 words
An amide as claimed in claim 1 which is of the following formula Id, ##STR3## wherein: X and Z are selected from the group consisting of: (A) X is ArY wherein Y is a linking group selected from carbonyl, sulfinyl, and sulfonyl and Ar is selected from the group consisting of phenyl, 2-, 3- and 4-fluorophenyl, 2- and 3-chlorophenyl, 2- and 3-cyanophenyl, 2- and 3-hydroxyphenyl, 2- and 3-methoxyphenyl, and 2- and 3-methylphenyl[, 2-, 3-, and 4-pyridyl, 2- and 4-pyrimidinyl, 3- and 4-isothiazolyl, 2- and 4-oxazolyl, 2- and 4-thiazolyl, 2- and 3-furyl, and 2- and 3-thienyl]; Z is selected from hydrogen, cyano, halo, hydroxy, (1-2C)alkyl, and (1-2C)alkoxy; (B) X is CN, Z is phenylsulfonyl; R 2 and R 3 are independently selected from the group consisting of (1-3C)alkyl substituted by from 0 to 2k+1 fluoro groups wherein k is the number of carbon atoms in the said (1-3C)alkyl, provided that R 2 and R 3 are not both methyl; and pharmaceutically acceptable in vivo hydrolyzable esters of said amide; and pharmaceutically acceptable salts of said amides and said esters.
Claim 4
Dependent Claim
164 words
An amide as claimed in claim 2, wherein X is ArY and wherein Ar, Y, and Z are selected from the group consisting of: (i) Y is sulfonyl, Z is hydrogen, and Ar is selected from the group consisting of: phenyl substituted with 0-1 substitutents, selected from phenyl, 2-, 3-, and 4-fluorophenyl, 2- and 3-chlorophenyl, 2- and 3-methoxyphenyl, 2- and 3-cyanophenyl, 2- and 3-hydroxyphenyl, and 2- and 3-methylphenyl; (ii) Y is sulfonyl, Ar is phenyl and Z is selected from the group consisting of cyano, fluoro, hydroxy, methoxy and methyl; and (iii) Y is carbonyl, Z is hydrogen, and Ar is phenyl; and R 2 and R 3 are independently selected from the group consisting of (i) R 2 is trifluoromethyl and R 3 is selected from methyl, ethyl, and trifluoromethyl; and (ii) R 2 is difluoromethyl and R 3 is difluoromethyl; and the pharmaceutically acceptable in vivo hydrolyzable esters of said amide, and pharmaceutically acceptable salts of said amide and said hydrolyzable esters.
Claim 5
Dependent Claim
35 words
An amide as claimed in claim 3, which is selected from: N-[4-(Phenylcarbonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide; S-(-)-N-[4-(Phenylcarbonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide; and N-[4-(Phenylcarbonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-trifluoromethylmethylpropanamide; and pharmaceutically acceptable in vivo hydrolyzable esters of said amide; and pharmaceutically acceptable salts of said amide and said esters.
Claim 6
Dependent Claim
283 words
A pharmaceutical composition comprising an amide of the following formula I, or a pharmaceutically acceptable in vivo hydrolyzable ester of said amide, or a pharmaceutically acceptable salt of said amide or of said ester, ##STR4## wherein: E is CZ wherein C is a ring carbon and Z is a substituent defined below, wherein: X and Z are selected from the group consisting of: (A) X is ArY wherein Y is a linking group selected from carbonyl, sulfinyl, and sulfonyl and Ar is selected from the group consisting of: phenyl substituted with 0-2 substituents selected from halo, hydroxy, cyano, (1-4C)alkyl, and (1-4C)alkoxy, provided that the 4-position of said phenyl may be substituted by fluoro only, and that the said phenyl may not be 3,5-disubstituted; provided that Ar is not 3-chlorophenyl, 3-bromophenyl, 3-iodophenyl or 3-(1-4C) alkylphenyl when Y is carbonyl; and Z is selected from hydrogen, cyano, halo, hydroxy, (1-4C)alkyl, and (1-4C)alkoxy; (B) X is cyano and Z is selected from the group consisting of phenylthio, phenylsulfinyl, and phenylsulfonyl the phenyl rings of which are substituted with 0-2 substituents selected from halo, hydroxy, cyano, nitro (1-4C)alkyl, and (1-4)alkoxy; R 2 and R 3 are independently selected from the group consisting of (1-3C)alkyl substituted by from 0 to 2k+1 groups selected from fluoro and chloro wherein k is the number of carbon atoms in the said (1-3C)alkyl, provided that R 2 and R 3 are not both methyl; or together, with the carbon atom to which both R 2 and R 3 are attached, form a 3-5 membered cycloalkyl ring optionally substituted by from 0 to 2m-2 fluoro groups wherein m is the number of carbon atoms in said ring; and pharmaceutically acceptable diluent or carrier.
Claim 7
Dependent Claim
283 words
A pharmaceutical composition comprising an amide of the following formula I, or a pharmaceutically acceptable in vivo hydrolyzable ester of said amide, or a pharmaceutically acceptable salt of said amide or of said ester, ##STR4## wherein: E is CZ wherein C is a ring carbon and Z is a substituent defined below, wherein: X and Z are selected from the group consisting of: (A) X is ArY wherein Y is a linking group selected from carbonyl, sulfinyl, and sulfonyl and Ar is selected from the group consisting of: phenyl substituted with 0-2 substituents selected from halo, hydroxy, cyano, (1-4C)alkyl, and (1-4C)alkoxy, provided that the 4-position of said phenyl may be substituted by fluoro only, and that the said phenyl may not be 3,5-disubstituted; provided that Ar is not 3-chlorophenyl, 3-bromophenyl, 3-iodophenyl or 3-(1-4C) alkylphenyl when Y is carbonyl; and Z is selected from hydrogen, cyano, halo, hydroxy, (1-4C)alkyl, and (1-4C)alkoxy; (B) X is cyano and Z is selected from the group consisting of phenylthio, phenylsulfinyl, and phenylsulfonyl the phenyl rings of which are substituted with 0-2 substituents selected from halo, hydroxy, cyano, nitro (1-4C)alkyl, and (1-4)alkoxy; R 2 and R 3 are independently selected from the group consisting of (1-3C)alkyl substituted by from 0 to 2k+1 groups selected from fluoro and chloro wherein k is the number of carbon atoms in the said (1-3C)alkyl, provided that R 2 and R 3 are not both methyl; or together, with the carbon atom to which both R 2 and R 3 are attached, form a 3-5 membered cycloalkyl ring optionally substituted by from 0 to 2m-2 fluoro groups wherein m is the number of carbon atoms in said ring; and pharmaceutically acceptable diluent or carrier.
Claim 8
Dependent Claim
139 words
A composition as claimed in claim 5, wherein said amide is of the following formula Id, ##STR5## wherein: X and Z are selected from the group consisting of: (A) X is ArY wherein Y is a linking group selected from carbonyl, sulfinyl, and sulfonyl and Ar is selected from the group consisting of phenyl, 2-, 3- and 4-fluorophenyl, 2- and 3-chlorophenyl, 2- and 3-¢cyanophenyl, 2- and 3-hydroxyphenyl, 2- and 3-methoxyphenyl, and 2- and 3-methylphenyl; Z is selected from hydrogen, cyano, halo, hydroxy, (1-2C) alkyl, and (1-2C) alkoxy; (B) X is CN, Z is phenylsulfonyl; R 2 and R 3 are independently selected from the group consisting of (1-3C)alkyl substituted by from 0 to 2k+1 fluoro groups wherein k is the number of carbon atoms in the said (1-3C)alkyl, provided that R 2 and R 3 are not both methyl.
Claim 9
Dependent Claim
152 words
A composition as claimed in claim 6, wherein X is ArY and wherein Ar, Y, and Z are selected from the group consisting of: (i) Y is sulfonyl, Z is hydrogen, and Ar is selected from the group consisting of: phenyl substituted with 0-1 substitutents, selected from phenyl, 2-, 3-, and 4-fluorophenyl, 2- and 3-chlorophenyl, 2- and 3-methoxyphenyl, 2- and 3-cyanophenyl, 2- and 3-hydroxyphenyl, and 2- and 3-methylphenyl; (ii) Y is sulfonyl, Ar is phenyl and Z is selected from the group consisting of cyano, fluoro, hydroxy, methoxy and methyl; and (iii) Y is carbonyl, Z is hydrogen, and Ar is; and R 2 and R 3 are independently selected from the group consisting of (i) R 2 is trifluoromethyl and R 3 is selected from methyl, ethyl, and trifluoromethyl; and (ii) R 2 is difluoromethyl and R 3 is difluoromethyl; and the pharmaceutically acceptable in vivo hydrolyzable esters of said amide.
Claim 10
Dependent Claim
17 words
A composition as claimed in claim 7, wherein said amide is selected from: N-[4-(Phenylcarbonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide; S-(-)-N-[4-(Phenylcarbonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide; and N-[4-(Phenylcarbonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-trifluoromethylmethylpropanamide.
Claim 11
Independent Claim
294 words
A method of treating urinary incontinence, comprising administering to a mammal in need of such treatment an effective amount of an amide of the following formula I, or a pharmaceutically acceptable in vivo hydrolyzable ester of said amide, or a pharmaceutically acceptable salt of said amide or of said ester, ##STR6## wherein: E is CZ wherein C is a ring carbon and Z is a substituent defined below, wherein: X and Z are selected from the group consisting of: (A) X is ArY wherein Y is a linking group selected from carbonyl, sulfinyl, and sulfonyl and Ar is selected from the group consisting of: phenyl substituted with 0-2 substituents selected from halo, hydroxy, cyano, (1-4C)alkyl, and (1-4C)alkoxy, provided that the 4-position of said phenyl may be substituted by fluoro only, and that the said phenyl may not be 3,5-disubstituted; provided that Ar is not 3-chlorophenyl, 3-bromophenyl, 3-iodophenyl or 3-(1-4C) alkylphenyl when Y is carbonyl; and Z is selected from hydrogen, cyano, halo, hydroxy, (1-4C) alkyl, and (1-4C)alkoxy; (B) X is cyano and Z is selected from the group consisting of phenylthio, phenylsulfinyl, and phenylsulfonyl the phenyl rings of which are substituted with 0-2 substituents selected from halo, hydroxy, cyano, nitro (1-4C)alkyl, and (1-4)alkoxy; R 2 and R 3 are independently selected from the group consisting of (1-3C)alkyl substituted by from 0 to 2k+1 groups selected from fluoro and chloro wherein k is the number of carbon atoms in the said (1-3C)alkyl, provided that R 2 and R 3 are not both methyl; or together, with the carbon atom to which both R 2 and R 3 are attached, form a 3-5 membered cycloalkyl ring optionally substituted by from 0 to 2m-2 fluoro groups wherein m is the number of carbon atoms in said ring.
Claim 12
Independent Claim
294 words
A method of treating urinary incontinence, comprising administering to a mammal in need of such treatment an effective amount of an amide of the following formula I, or a pharmaceutically acceptable in vivo hydrolyzable ester of said amide, or a pharmaceutically acceptable salt of said amide or of said ester, ##STR6## wherein: E is CZ wherein C is a ring carbon and Z is a substituent defined below, wherein: X and Z are selected from the group consisting of: (A) X is ArY wherein Y is a linking group selected from carbonyl, sulfinyl, and sulfonyl and Ar is selected from the group consisting of: phenyl substituted with 0-2 substituents selected from halo, hydroxy, cyano, (1-4C)alkyl, and (1-4C)alkoxy, provided that the 4-position of said phenyl may be substituted by fluoro only, and that the said phenyl may not be 3,5-disubstituted; provided that Ar is not 3-chlorophenyl, 3-bromophenyl, 3-iodophenyl or 3-(1-4C) alkylphenyl when Y is carbonyl; and Z is selected from hydrogen, cyano, halo, hydroxy, (1-4C) alkyl, and (1-4C)alkoxy; (B) X is cyano and Z is selected from the group consisting of phenylthio, phenylsulfinyl, and phenylsulfonyl the phenyl rings of which are substituted with 0-2 substituents selected from halo, hydroxy, cyano, nitro (1-4C)alkyl, and (1-4)alkoxy; R 2 and R 3 are independently selected from the group consisting of (1-3C)alkyl substituted by from 0 to 2k+1 groups selected from fluoro and chloro wherein k is the number of carbon atoms in the said (1-3C)alkyl, provided that R 2 and R 3 are not both methyl; or together, with the carbon atom to which both R 2 and R 3 are attached, form a 3-5 membered cycloalkyl ring optionally substituted by from 0 to 2m-2 fluoro groups wherein m is the number of carbon atoms in said ring.
Claim 13
Dependent Claim
137 words
A method as claimed in claim 9 wherein said amide is of the following formula Id, ##STR7## wherein: X and Z are selected from the group consisting of: (A) X is ArY wherein Y is a linking group selected from carbonyl, sulfinyl, and sulfonyl and Ar is selected from the group consisting of phenyl, 2-, 3- and 4-fluorophenyl, 2- and 3-chlorophenyl, 2- and 3-cyanophenyl, 2- and 3-hydroxyphenyl, 2- and 3-methoxyphenyl, and 2- and 3-methylphenyl; Z is selected from hydrogen, cyano, halo, hydroxy, (1-2C)alkyl, and (1-2C)alkoxy; (B) X is CN, Z is phenylsulfonyl; R 2 and R 3 are independently selected from the group consisting of (1-3C)alkyl substituted by from 0 to 2k+1 fluoro groups wherein k is the number of carbon atoms in the said (1-3C)alkyl, provided that R 2 and R 3 are not both methyl.
Claim 14
Dependent Claim
141 words
A method as claimed in claim 10, wherein X is ArY and wherein Ar, Y, and Z are selected from the group consisting of: (i) Y is sulfonyl, Z is hydrogen, and Ar is selected from the group consisting of: phenyl substituted with 0-1 substitutents, selected from phenyl, 2-, 3-, and 4-fluorophenyl, 2- and 3-chlorophenyl, 2- and 3-methoxyphenyl, 2- and 3-cyanophenyl, 2- and 3-hydroxyphenyl, and 2- and 3-methylphenyl; (ii) Y is sulfonyl, Ar is phenyl and Z is selected from the group consisting of cyano, fluoro, hydroxy, methoxy and methyl; and (iii) Y is carbonyl, Z is hydrogen, and Ar is; and R 2 and R 3 are independently selected from the group consisting of (i) R 2 is trifluoromethyl and R 3 is selected from methyl, ethyl, and trifluoromethyl; and (ii) R 2 is difluoromethyl and R 3 is difluoromethyl.
Claim 15
Dependent Claim
16 words
A method as claimed in claim 11, wherein said amide is selected from: N-[4-(Phenylcarbonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide; S-(-)-N-[4-(Phenylcarbonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide; N-[4-(Phenylcarbonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-trifluoromethylmethylpropanamide.
Claim 16
Dependent Claim
250 words
An amide of the following formula I, ##STR8## wherein: E is CZ wherein C is a ring carbon and Z is a substituent defined below, wherein: X and Z are selected from the group consisting of: (A) X is ArY wherein Y is a linking group selected from carbonyl, sulfinyl, and sulfonyl and Ar is selected from the group consisting of: phenyl substituted with 0-2 substituents selected from halo, hydroxy, cyano, (1-4C)alkyl, and (1-4C)alkoxy, provided that the 4-position of said phenyl may be substituted by fluoro only, and that the said phenyl may not be 3,5-disubstituted; provided that Ar is not 3-chlorophenyl, 3-bromophenyl, 3-iodophenyl or 3-(1-4C) alkylphenyl when Y is carbonyl; and Z is selected from hydrogen, cyano, halo, hydroxy, (1-4C)alkyl, and (1-4C)alkoxy; (B) X is cyano and Z is selected from the group consisting of phenylthio, phenylsulfinyl, and phenylsulfonyl the phenyl rings of which are substituted with 0-2 substituents selected from halo, hydroxy, cyano, nitro (1-4C)alkyl, and (1-4)alkoxy; R 2 and R 3 are independently selected from the group consisting of (1-3C)alkyl substituted by from 0 to 2k+1 groups selected from fluoro and chloro wherein k is the number of carbon atoms in the said (1-3C)alkyl, provided that R 2 and R 3 are not both methyl; or together, with the carbon atom to which both R 2 and R 3 are attached, form a 3-5 membered cycloalkyl ring optionally substituted by from 0 to 2m-2 fluoro groups wherein m is the number of carbon atoms in said ring.
Claim 17
Dependent Claim
250 words
An amide of the following formula I, ##STR8## wherein: E is CZ wherein C is a ring carbon and Z is a substituent defined below, wherein: X and Z are selected from the group consisting of: (A) X is ArY wherein Y is a linking group selected from carbonyl, sulfinyl, and sulfonyl and Ar is selected from the group consisting of: phenyl substituted with 0-2 substituents selected from halo, hydroxy, cyano, (1-4C)alkyl, and (1-4C)alkoxy, provided that the 4-position of said phenyl may be substituted by fluoro only, and that the said phenyl may not be 3,5-disubstituted; provided that Ar is not 3-chlorophenyl, 3-bromophenyl, 3-iodophenyl or 3-(1-4C) alkylphenyl when Y is carbonyl; and Z is selected from hydrogen, cyano, halo, hydroxy, (1-4C)alkyl, and (1-4C)alkoxy; (B) X is cyano and Z is selected from the group consisting of phenylthio, phenylsulfinyl, and phenylsulfonyl the phenyl rings of which are substituted with 0-2 substituents selected from halo, hydroxy, cyano, nitro (1-4C)alkyl, and (1-4)alkoxy; R 2 and R 3 are independently selected from the group consisting of (1-3C)alkyl substituted by from 0 to 2k+1 groups selected from fluoro and chloro wherein k is the number of carbon atoms in the said (1-3C)alkyl, provided that R 2 and R 3 are not both methyl; or together, with the carbon atom to which both R 2 and R 3 are attached, form a 3-5 membered cycloalkyl ring optionally substituted by from 0 to 2m-2 fluoro groups wherein m is the number of carbon atoms in said ring.
Claim 18
Dependent Claim
135 words
An amide as claimed in claim 13 which is of the following formula Id, ##STR9## wherein: X and Z are selected from the group consisting of: (A) X is ArY wherein Y is a linking group selected from carbonyl, sulfinyl, and sulfonyl and Ar is selected from the group consisting of phenyl, 2-, 3- and 4-fluorophenyl, 2- and 3-chlorophenyl, 2- and 3-cyanophenyl, 2- and 3-hydroxyphenyl, 2- and 3-methoxyphenyl, and 2- and 3-methylphenyl; Z is selected from hydrogen, cyano, halo, hydroxy, (1-2C)alkyl, and (1-2C)alkoxy; (B) X is CN, Z is phenylsulfonyl; R 2 and R 3 are independently selected from the group consisting of (1-3C)alkyl substituted by from 0 to 2k+1 fluoro groups wherein k is the number of carbon atoms in the said (1-3C)alkyl, provided that R 2 and R 3 are not both methyl.
Claim 19
Dependent Claim
143 words
An amide as claimed in claim 14, wherein X is ArY and wherein Ar, Y, and Z are selected from the group consisting of: (i) Y is sulfonyl, Z is hydrogen, and Ar is selected from the group consisting of: phenyl substituted with 0-1 substitutent, selected from phenyl, 2-, 3-, and 4-fluorophenyl, 2- and 3-chlorophenyl, 2- and 3-methoxyphenyl, 2- and 3-cyanophenyl, 2- and 3-hydroxyphenyl, and 2- and 3-methylphenyl; (ii) Y is sulfonyl, Ar is phenyl, and Z is selected from the group consisting of cyano, fluoro, hydroxy, methoxy and methyl; and (iii) Y is carbonyl, Z is hydrogen, and Ar is phenyl and; and R 2 and R 3 are independently selected from the group consisting of (i) R 2 is trifluoromethyl and R 3 is selected from methyl, ethyl, and trifluoromethyl; and (ii) R 2 is difluoromethyl and R 3 is difluoromethyl.
Claim 20
Dependent Claim
15 words
An amide as claimed in claim 15, which is selected from: N-[4-(Phenylcarbonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide; S-(-)-N-[4-(Phenylcarbonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide; and N-[4-(Phenylcarbonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-trifluoromethylmethylpropanamide.
References Cited (Backward Citations)
US3468878A
Cited
US3365485A
Cited
NL7008629A
Cited
NL7008627A
Cited
US3715375A
Cited
US4282218A
Cited
US4191775A
Cited
US4329776A
Cited
US4386080A
Cited
US4535092A
Cited
US4636505A
Cited
US5032592A
Cited
EP0181568A2
Cited
EP0189142A2
Cited
EP0253503A2
Cited
US4880839A
Cited
EP0274867A2
Cited
US5272982A
Cited
EP0409414A1
Cited
EP0409413A2
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1998-01-16 | 1998-07-18 | 1999-01-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2002-01-16 | 2002-07-18 | 2003-01-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2006-01-16 | 2006-07-18 | 2007-01-17 | $7700.00 | Window Closed / Lapsed |