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US 5,670,504 AGranted
2,6-diaryl pyridazinones with immunosuppressant activity
AssigneeMerck & Co., Inc.
InventorsRichard J. Bochis, Andrew Kotliar, William H. Parsons, Kathleen Rupprecht
Life of this patent
Estimating the term…
Abstract
A class of 2,6-diarylpyridazinones of general structural formula I have been identified that exhibit exhibit immunosuppressant activity with human T-lymphocytes, and are useful as an immunosuppressants. ##STR1## or a pharmaceutically acceptable salt, hydrate or crystal form thereof
Claims6
A compound of formula I ##STR9## or a pharmaceutically acceptable salt, hydrate or crystal form thereof, wherein:
- M is S(O).sub.p,
- p is 0, 1 or 2,
- R.sup.1 and R.sup.2 are selected from:
- (a) aryl;
- (b) substituted aryl in which as many as three substituents, X, Y, and Z, may be present;
- X, Y and Z independently are selected from:
- (a) hydrogen, except that when R.sup.1 is 4-chlorophenyl, then R.sup.2 can not be phenyl,
- (b) C.sub.1-10 alkyl, unsubstituted or substituted with a substituent selected from the group consisting of:
- (i) aryl,
- (ii) C.sub.1-6 alkoxy,
- (iii) --NO.sub.2
- (iv) --NR.sup.3 R.sup.4,
- (v) --CO.sub.2 H,
- (vi) --OH, and
- (vii) oxo;
- except that when R.sup.2 is 2-methyl-phenyl--, 3-methyl-phenyl, or 4-methyl-phenyl, then R.sup.1 can not be 4-chloro-phenyl-;
- (c) C.sub.1-10 alkoxy, unsubstituted or substituted with a substituent selected from the group consisting of:
- (i) aryl,
- (ii) C.sub.1-6 alkoxy,
- (iii) --NO.sub.2
- (iV) --NR.sup.3 R.sup.4,
- (v) --CO.sub.2 H,
- (vi) --OH, and
- (vii) oxo;
- except that when R.sup.2 is 4-methoxyphenyl, then R.sup.1 is not 4-chlorophenyl, phenyl or --SO.sub.2 -phenyl;
- (d) aryl,
- (e) aryloxy,
- (f) halogen, except that when R.sup.2 is 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl or 4-bromophenyl, then R.sup.1 is not 4-chlorophenyl,
- (g) --NO.sub.2, except that when R.sup.2 is 3-nitrophenyl, then R.sup.1 is not 4-chlorophenyl,
- (h) --NR.sup.3 R.sup.4,
- (i) --CN,
- (k) --CF.sub.3,
- (l) --S(O).sub.p R.sup.7, wherein R.sup.7 is hydrogen, C.sub.1-6 alkyl, trifluoromethyl, or phenyl, except that when X, Y or Z is S(O).sub.p R.sup.7, then M cannot be SO or SO.sub.2,
- (m) --CH(OR.sup.8)(OR.sup.9),
- (n) OH, and
- (o) OCF.sub.3, provided that p is 0, R.sup.1 is phenyl, and R.sup.2 is phenyl substituted with methoxy;
- R.sup.3 and R.sup.4 are independently selected from:
- (a) hydrogen,
- (b) C .sub.1-6 alkyl unsubstituted or substituted, wherein the substituted group is selected from:
- (i) --OH,
- (ii) --C.sub.1-6 alkoxy,
- (iii) --CO.sub.2 H,
- (iv) oxo,
- (v) --C.sub.3-7 cycloalkyl, and
- (vi) --C.sub.1-6 alkyl--OH;
- R.sup.8 and R.sup.9 are C.sub.1-3 alkyl or taken together form an ethyl or propyl bridge;
- M.sup.+ is a positively charged inorganic or organic counterion,
- n is 1 or 2;
- q is 1, 2 or 3;
- aryl is defined in all instances above as phenyl or naphthyl;
- and
- aryloxy is defined in all instances above as phenoxy or naphthyloxy;
- provided that when M represents S and more than one of X, Y or Z represents S(O).sub.p R.sup.7, then p represents the same number of oxygen atoms on S(O).sub.p R.sup.7 ;
- and when M is SO or SO.sub.2, then X, Y or Z cannot represent S(O).sub.p R.sup.7.
51 more elements
A compound of formula ##STR10## or a pharmaceutically accceptable salt, hydrate or crystal form thereof, where M is S, SO or SO.sub.2 and R.sup.1 and R.sup.2 are selected from Table 1:
- TABLE1 ______________________________________ R.sup.1 R.sup.2 ______________________________________ phenyl phenyl 2-methylphenyl " 3-methylphenyl " 4-methylphenyl " 3,4-dimethylphenyl " 3,5-dimethylphenyl " phenyl 3-CH.sub.3 Ophenyl 2-methylphenyl " 3-methylphenyl " 4-methylphenyl " 3,4-dimethylphenyl " 3,5-dimethylphenyl " phenyl 3-NO.sub.2 phenyl 2-methylphenyl " 3-methylphenyl " 4-methylphenyl " 3,4-dimethylphenyl " 3,5-dimethylphenyl " phenyl 3-CH.sub.3 Sphenyl 2-methylphenyl " 3-methylphenyl " 4-methylphenyl " 3,4-dimethylphenyl " 3,5-dimethylphenyl " phenyl 3-CH.sub.3 SOphenyl 2-methylphenyl " 3-methylphenyl " 4-methylphenyl " 3,4-dimethylphenyl " 3,5-dimethylphenyl " phenyl 3-CH.sub.3 SO.sub.2 phenyl 2-methylphenyl " 3-methylphenyl " 4-methylphenyl " 3,4-dimethylphenyl " 3,5-dimethylphenyl " 2-methylphenyl 4-CH.sub.3 Ophenyl 3-methylphenyl " 4-methylphenyl " 3,4-dimethylphenyl " 3,5-dimethylphenyl " phenyl 4-NO.sub.2 phenyl 2-methylphenyl " 3-methylphenyl " 4-methylphenyl " 3,4-dimethylphenyl " 3,5-dimethylphenyl " phenyl 4-CH.sub.3 Sphenyl 2-methylphenyl " 3-methylphenyl " 4-methylphenyl " 3,4-dimethylphenyl " 3,5-dimethylphenyl " phenyl 4-CH.sub.3 SOphenyl 2-methylphenyl " 3-methylphenyl " 4-methylphenyl " 3,4-dimethylphenyl " 3,5-dimethylphenyl " phenyl 4-CH.sub.3 SO.sub.2 phenyl 2-methylphenyl " 3-methylphenyl " 4-methylphenyl " 3,4-dimethylphenyl " 3,5-dimethylphenyl " phenyl 3,4-OCH.sub.2 Ophenyl 2-methylphenyl " 3-methylphenyl " 4-methylphenyl " 3,4-dimethylphenyl " 3,5-dimethylphenyl " 2-CH.sub.3 Ophenyl Phenyl 3-CH.sub.3 Ophenyl " 4-CH.sub.3 Ophenyl " 3,4-bis-CH.sub.3 Ophenyl " 3,5-bis-CH.sub.3 Ophenyl " 2-CH.sub.3 Ophenyl 3-CH.sub.3 Ophenyl 3-CH.sub.3 Ophenyl " 4-CH.sub.3 Ophenyl " 3,4-bis-CH.sub.3 Ophenyl " 3,5-bis-CH.sub.3 Ophenyl " 2-CH.sub.3 Ophenyl 3-NO.sub.2 phenyl 3-CH.sub.3 Ophenyl " 4-CH.sub.3 Ophenyl " 3,4-bis-CH.sub.3 Ophenyl " 3,5-bis-CH.sub.3 Ophenyl " 2-CH.sub.3 Ophenyl 3-CH.sub.3 Sphenyl 3-CH.sub.3 Ophenyl " 4-CH.sub.3 Ophenyl " 3,4-bis-CH.sub.3 Ophenyl " 3,5-bis-CH.sub.3 Ophenyl " 2-CH.sub.3 Ophenyl 3-CH.sub.3 SOphenyl 3-CH.sub.3 Ophenyl " 4-CH.sub.3 Ophenyl " 3,4-bis-CH.sub.3 Ophenyl " 3,5-bis-CH.sub.3 Ophenyl " 2-CH.sub.3 Ophenyl 3-CH.sub.3 SO.sub.2 phenyl 3-CH.sub.3 Ophenyl " 4-CH.sub.3 Ophenyl " 3,4-bis-CH.sub.3 Ophenyl " 3,5-bis-CH.sub.3 Ophenyl " 2-CH.sub.3 Ophenyl 4-CH.sub.3 Ophenyl 3-CH.sub.3 Ophenyl " 4-CH.sub.3 Ophenyl " 3,4-bis-CH.sub.3 Ophenyl " 3,5-bis-CH.sub.3 Ophenyl " 2-CH.sub.3 OPhenyl 4-NO.sub.2 phenyl 3-CH.sub.3 Ophenyl " 4-CH.sub.3 Ophenyl " 3,4-bis-CH.sub.3 Ophenyl " 3,5-bis-CH.sub.3 Ophenyl " 2-CH.sub.3 Ophenyl 4-CH.sub.3 Sphenyl 3-CH.sub.3 Ophenyl " 4-CH.sub.3 Ophenyl " 3,4-bis-CH.sub.3 Ophenyl " 3,5-bis-CH.sub.3 Ophenyl " 2-CH.sub.3 Ophenyl 4-CH.sub.3 SOphenyl 3-CH.sub.3 Ophenyl " 4-CH.sub.3 Ophenyl " 3,4-bis-CH.sub.3 Ophenyl " 3,5-bis-CH.sub.3 Ophenyl " 2-CH.sub.3 Ophenyl 4-CH.sub.3 SO.sub.2 Phenyl 3-CH.sub.3 Ophenyl " 4-CH.sub.3 Ophenyl " 3,4-bis-CH.sub.3 Ophenyl " 3,5-bis-CH.sub.3 Ophenyl " 2-CH.sub.3 Ophenyl 3,4-CH.sub.2 OCH.sub.2 phenyl 3-CH.sub.3 Ophenyl " 4-CH.sub.3 Ophenyl " 3,4-bis-CH.sub.3 Ophenyl " 3,5-bis-CH.sub.3 Ophenyl " 2-CH.sub.3 Sphenyl Phenyl 3-CH.sub.3 Sphenyl " 4-CH.sub.3 Sphenyl " 3,4-bis-CH.sub.3 Sphenyl " 3,5-bis-CH.sub.3 Sphenyl " 2-CH.sub.3 Sphenyl 3-CH.sub.3 Ophenyl 3-CH.sub.3 Sphenyl " 4-CH.sub.3 Sphenyl " 3,4-bis-CH.sub.3 Sphenyl " 3,5-bis-CH.sub.3 Sphenyl " 2-CH.sub.3 Sphenyl 3-NO.sub.2 phenyl 3-CH.sub.3 Sphenyl " 4-CH.sub.3 Sphenyl " 3,4-bis-CH.sub.3 Sphenyl " 3,5-bis-CH.sub.3 Sphenyl " 2-CH.sub.3 Sphenyl 3-CH.sub.3 Sphenyl 3-CH.sub.3 Sphenyl " 4-CH.sub.3 Sphenyl " 3,4-bis-CH.sub.3 Sphenyl " 3,5-bis-CH.sub.3 Sphenyl " 2-CH.sub.3 Sphenyl 4-CH.sub.3 Ophenyl 3-CH.sub.3 Sphenyl " 4-CH.sub.3 Sphenyl " 3,4-bis-CH.sub.3 Sphenyl " 3,5-bis-CH.sub.3 Sphenyl " 2-CH.sub.3 Sphenyl 4-NO.sub.2 phenyl 3-CH.sub.3 Sphenyl " 4-CH.sub.3 Sphenyl " 3,4-bis-CH.sub.3 Sphenyl " 3,5-bis-CH.sub.3 Sphenyl " 2-CH.sub.3 Sphenyl 4-CH.sub.3 Sphenyl 3-CH.sub.3 Sphenyl " 4-CH.sub.3 Sphenyl " 3,4-bis-CH.sub.3 Sphenyl " 3,5-bis-CH.sub.3 Sphenyl " 2-CH.sub.3 Sphenyl 3,4-CH.sub.2 OCH.sub.2 Phenyl 3-CH.sub.3 Sphenyl " 4-CH.sub.3 Sphenyl " 3,4-bis-CH.sub.3 Sphenyl " 3,5-bis-CH.sub.3 Sphenyl " 2-CH.sub.3 SOphenyl Phenyl 3-CH.sub.3 SOphenyl " 4-CH.sub.3 SOphenyl " 3,4-bis-CH.sub.3 SOphenyl " 2-CH.sub.3 SOphenyl 3-CH.sub.3 Ophenyl 3-CH.sub.3 SOphenyl " 4-CH.sub.3 SOphenyl " 3,4-bis-CH.sub.3 SOphenyl " 3,5-bis-CH.sub.3 SOphenyl " 2-CH.sub.3 SOphenyl 3-NO.sub.2 phenyl 3-CH.sub.3 SOphenyl " 4-CH.sub.3 SOphenyl " 3,4-bis-CH.sub.3 SOphenyl " 3,5-bis-CH.sub.3 SOphenyl " 2-CH.sub.3 SOphenyl 3-CH.sub.3 SOphenyl 3-CH.sub.3 SOphenyl " 4-CH.sub.3 SOphenyl " 3,4-bis-CH.sub.3 SOphenyl " 3,5-bls-CH.sub.3 SOphenyl " 2-CH.sub.3 SOphenyl 4-CH.sub.3 Ophenyl 3-CH.sub.3 SOphenyl " 4-CH.sub.3 SOphenyl " 3,4-bis-CH.sub.3 SOphenyl " 3,5-bis-CH.sub.3 SOphenyl " 2-CH.sub.3 SOphenyl 4-NO.sub.2 phenyl 3-CH.sub.3 SOphenyl " 4-CH.sub.3 SOphenyl " 3,4-bis-CH.sub.3 SOphenyl " 3,5-bis-CH.sub.3 SOphenyl " 2-CH.sub.3 SOphenyl 4-CH.sub.3 SOphenyl 3-CH.sub.3 SOphenyl " 4-CH.sub.3 SOphenyl " 3,4-bis-CH.sub.3 SOphenyl " 3,5-bis-CH.sub.3 SOphenyl " 2-CH.sub.3 SOphenyl 3,4-CH.sub.2 OCH.sub.2 phenyl 3-CH.sub.3 SOphenyl " 4-CH.sub.3 SOphenyl " 3,4-bis-CH.sub.3 SOphenyl " 3,5-bis-CH.sub.3 SOphenyl " 2-CH.sub.3 SO.sub.2 phenyl Phenyl 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-bis-CH.sub.3 SO.sub.2 phenyl " 3,5-bis-CH.sub.3 SO.sub.2 phenyl " 2-CH.sub.3 SO.sub.2 phenyl 3-CH.sub.3 Ophenyl 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-bis-CH.sub.3 SO.sub.2 phenyl " 3,5-bis-CH.sub.3 SO.sub.2 phenyl " 2-CH.sub.3 SO.sub.2 phenyl 3-NO.sub.2 phenyl 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-bis-CH.sub.3 SO.sub.2 phenyl " 3,5-bis-CH.sub.3 SO.sub.2 phenyl " 2-CH.sub.3 SO.sub.2 phenyl 3-CH.sub.3 SO.sub.2 phenyl 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-bis-CH.sub.3 SO.sub.2 phenyl " 3,5-bis-CH.sub.3 SO.sub.2 phenyl " 2-CH.sub.3 SO.sub.2 phenyl 4-CH.sub.3 Ophenyl 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-bis-CH.sub.3 SO.sub.2 phenyl " 3,5-bis-CH.sub.3 SO.sub.2 phenyl " 2-CH.sub.3 SO.sub.2 phenyl 4-NO.sub.2 phenyl 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-bis-CH.sub.3 SO.sub.2 phenyl " 3,5-bis-CH.sub.3 SO.sub.2 phenyl " 2-CH.sub.3 SO.sub.2 phenyl 4-CH.sub.3 SO.sub.2 phenyl 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-bis-CH.sub.3 SO.sub.2 phenyl " 3,5-bis-CH.sub.3 SO.sub.2 phenyl " 2-CH.sub.3 SO.sub.2 phenyl 3,4-CH.sub.2 OCH.sub.2 phenyl 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-bis-CH.sub.3 SO.sub.2 phenyl " 3,5-bis-CH.sub.3 SO.sub.2 phenyl " 2-Clphenyl phenyl 3-Clphenyl " 3,4-di-Ciphenyl " 3,5-di-Clphenyl " 2-Clphenyl 3-CH.sub.3 Ophenyl 3-Ciphenyl " 4-Clphenyl " 3,4-di-Clphenyl " 3,5-Clphenyl " 2-Clphenyl 3-NO.sub.2 phenyl 3-Clphenyl " 3,4-di-Clphenyl " 3,5-Clphenyl " 2-Clphenyl 3-CH.sub.3 Sphenyl 3-Clphenyl " 4-Clphenyl " 3,4-di-Clphenyl " 3,5-Clphenyl " 2-Clphenyl 3-CH.sub.3 SOphenyl 3-Clphenyl " 4-Clphenyl " 3,4-di-Clphenyl " 3,5-Clphenyl " 2-Clphenyl 3-CH.sub.3 SO.sub.2 phenyl 3-Clphenyl " 4-Clphenyl " 3,4-di-Clphenyl " 3,5-Clphenyl " 2-Clphenyl 4-CH.sub.3 Ophenyl 3-Clphenyl " 3,4-Clphenyl " 3,5-Clphenyl " 2-Clphenyl 4-NO.sub.2 phenyl 3-Clphenyl " 4-Clphenyl " 3,4-Clphenyl " 3,5-Clphenyl " 2-Clphenyl 4-CH.sub.3 Sphenyl 3-Clphenyl " 4-Clphenyl " 3,4-Clphenyl " 3,5-Clphenyl " 2-Clphenyl 4-CH.sub.3 SOphenyl 3-Clphenyl " 4-Clphenyl " 3,4-Clphenyl " 3,5-Clphenyl " 2-Clphenyl 4-CH.sub.3 SO.sub.2 phenyl 3-Clphenyl " 4-Clphenyl " 3,4-Clphenyl " 3,5-Clphenyl " 2-Clphenyl 3,4-CH.sub.2 OCH.sub.2 phenyl 3-Clphenyl " 4-Clphenyl " 2-CF.sub.3 phenyl phenyl 3-CF.sub.3 phenyl " 4-CF.sub.3 phenyl " 3,4-di-CF.sub.3 phenyl " 3,5-diCF.sub.3 phenyl " 2-CF.sub.3 phenyl 3-CH.sub.3 Ophenyl 3-CF.sub.3 phenyl " 4-CF.sub.3 phenyl " 3,4-di-CF.sub.3 phenyl " 3,5-CF.sub.3 phenyl " 2-CF.sub.3 phenyl 3-NO.sub.2 phenyl 3-CF.sub.3 phenyl " 4-CF.sub.3 phenyl " 3,4-di-CF.sub.3 phenyl " 3,5-CF.sub.3 phenyl " 2-CF.sub.3 phenyl 3-CH.sub.3 Sphenyl 3-CF.sub.3 phenyl " 4-CF.sub.3 phenyl " 3,4-di-CF.sub.3 phenyl " 3,5-CF.sub.3 phenyl " 2-CF.sub.3 phenyl 3-CH.sub.3 SOphenyl 3-CF.sub.3 phenyl " 4-CF.sub.3 phenyl " 3,4-di-CF.sub.3 phenyl " 3,5-CF.sub.3 phenyl " 2-CF.sub.3 phenyl 3-CH.sub.3 SO.sub.2 phenyl 3-CF.sub.3 phenyl " 4-CF.sub.3 phenyl " 3,4-di-CF.sub.3 phenyl " 3,5-CF.sub.3 phenyl " 2-CF.sub.3 phenyl 4-CH.sub.3 Ophenyl 3-CF.sub.3 phenyl " 4-CF.sub.3 phenyl " 3,4-CF.sub.3 phenyl " 3,5-CF.sub.3 phenyl " 2-CF.sub.3 phenyl 4-NO.sub.2 phenyl 3-CF.sub.3 phenyl " 4-CF.sub.3 phenyl " 3,4-CF.sub.3 phenyl " 3,5-CF.sub.3 phenyl " 2-CF.sub.3 phenyl 4-CH.sub.3 Sphenyl 3-CF.sub.3 phenyl " 4-CF.sub.3 phenyl " 3,4-CF.sub.3 phenyl " 3,5-CF.sub.3 phenyl " 2-CF.sub.3 phenyl 4-CH.sub.3 SOphenyl 3-CF.sub.3 phenyl " 4-CF.sub.3 phenyl " 3,4-CF.sub.3 phenyl " 3,5-CF.sub.3 phenyl " 2-CF.sub.3 phenyl 4-CH.sub.3 SO.sub.2 phenyl 3-CF.sub.3 phenyl " 4-CF.sub.3 phenyl " 3,4-CF.sub.3 phenyl " 3,5-CF.sub.3 phenyl " 2-CF.sub.3 phenyl 3,4-CH.sub.2 OCH.sub.2 phenyl 3-CF.sub.3 phenyl " 4-CF.sub.3 phenyl " 3,4-CF.sub.3 phenyl " 3,5-CF.sub.3 phenyl " 2-Fphenyl phenyl 3-Fphenyl " 4-Fphenyl " 3,4-di-Fphenyl " 3,5-diFphenyl " 2-Fphenyl 3-CH.sub.3 Ophenyl 3-Fphenyl " 4-Fphenyl " 3,4-di-Fphenyl " 3,5-Fphenyl " 2-Fphenyl 3-NO.sub.2 phenyl 3-Fphenyl " 4-Fphenyl " 3,4-di-Fphenyl " 3,5-Fphenyl " 2-Fphenyl 3-CH.sub.3 Sphenyl 3-Fphenyl " 4-Fphenyl " 3,4-di-Fphenyl " 3,5-Fphenyl " 2-Fphenyl 3-CH.sub.3 SOphenyl 3-Fphenyl " 4-Fphenyl " 3,4-di-Fphenyl " 3,5-Fphenyl " 2-Fphenyl 3-CH.sub.3 SO.sub.2 phenyl 3-Fphenyl " 4-Fphenyl " 3,4-di-Fphenyl " 3,5-Fphenyl " 2-Fphenyl 4-CH.sub.3 OPhenyl 3-Fphenyl " 4-Fphenyl " 3,4-Fphenyl " 3,5-Fphenyl " 2-Fphenyl 4-NO.sub.2 phenyl 3-Fphenyl " 4-Fphenyl " 3,4-Fphenyl " 3,5-Fphenyl " 2-Fphenyl 4-CH.sub.3 SOphenyl 3-Fphenyl " 4-Fphenyl " 3,4-Fphenyl " 3,5-Fphenyl " 2-Fphenyl 4-CH.sub.3 SO.sub.2 phenyl 3-Fphenyl " 4-Fphenyl " 3,4-Fphenyl " 3,5-Fphenyl " 2-Fphenyl 3,4-CH.sub.2 OCH.sub.2 phenyl 3-Fphenyl " 4-Fphenyl " 3,4-Fphenyl " 3,5-Fphenyl " 2-ethylphenyl phenyl 3-ethylphenyl " 4-ethylphenyl " 3,4-diethylphenyl " 3,5-diethylphenyl " 2-ethylphenyl 3-CH.sub.3 Ophenyl 3-ethylphenyl " 4-ethylphenyl " 3,4-diethylphenyl " 3,5-diethylphenyl " 2-ethylphenyl 3-NO.sub.2 phenyl 3-ethylphenyl " 4-ethylphenyl " 3,4-diethylphenyl " 3,5-diethylphenyl " 2-ethylphenyl 3-CH.sub.3 Sphenyl 3-ethylphenyl " 4-ethylphenyl " 3,4-diethylphenyl " 3,5-diethylphenyl " 2-ethylphenyl 3-CH.sub.3 SOphenyl 3-ethylphenyl " 4-ethylphenyl " 3,4-diethylphenyl " 3,5-diethylphenyl " 2-ethylphenyl 3-CH.sub.3 SO.sub.2 phenyl 3-ethylphenyl " 4-ethylphenyl " 3,4-diethylphenyl " 3,5-diethylphenyl " 2-ethylphenyl 4-CH.sub.3 Ophenyl 3-ethylphenyl " 4-ethylphenyl " 3,4-diethylphenyl " 3,5-diethylphenyl " 2-ethylphenyl 4-NO.sub.2 phenyl 3-ethylphenyl " 4-ethylphenyl " 3,4-diethylphenyl " 3,5-diethylphenyl " 2-ethylphenyl 4-CH.sub.3 Sphenyl 3-ethylphenyl " 4-ethylphenyl " 3,4-diethylphenyl " 3,5-diethylphenyl " 2-ethylphenyl 4-CH.sub.3 SOphenyl 3-ethylphenyl " 4-ethylphenyl " 3,4-diethylphenyl " 3,5-diethylphenyl " 2-ethylphenyl 4-CH.sub.3 SO.sub.2 phenyl 3-ethylphenyl " 4-ethylphenyl " 3,4-diethylphenyl " 3,5-diethylphenyl " 2-ethylphenyl 3,4-CHOCH.sub.2 phenyl 3-ethylphenyl " 4-ethylphenyl " 3,4-diethylphenyl " 3,5-diethylphenyl " 2-phenylphenyl phenyl 3-phenylphenyl " 4-phenylphenyl " 2-phenylphenyl 3-CH.sub.3 Ophenyl 3-phenylphenyl " 4-phenylphenyl " 2-phenylphenyl 3-NO.sub.2 phenyl 3-phenylphenyl " 4-phenylphenyl " 2-phenylphenyl 3-CH.sub.3 Sphenyl 3-phenylphenyl " 4-phenylphenyl " 2-phenylphenyl 3-CH.sub.3 SOphenyl 3-phenylphenyl " 4-phenylphenyl " 2-phenylphenyl 3-CH.sub.3 SO.sub.2 phenyl 3-phenylphenyl " 4-phenylphenyl " 2-phenylphenyl 4-CH.sub.3 Ophenyl 3-phenylphenyl " 4-phenylphenyl " 2-phenylphenyl 4-NO.sub.2 phenyl 3-phenylphenyl " 4-phenylphenyl " 2-phenylphenyl 4-CH.sub.3 Sphenyl 3-phenylphenyl " 4-phenylphenyl " 2-phenylphenyl 4-CH.sub.3 SOphenyl 3-phenylphenyl " 4-phenylphenyl " 2-phenylphenyl 4-CH.sub.3 SO.sub.2 phenyl 3-phenylphenyl " 4-phenylphenyl " 2-phenylphenyl 3,4-CH.sub.2 OCH.sub.2 phenyl 3-phenylphenyl " 4-phenylphenyl " 2-phenoxyphenyl phenyl 3-phenoxyphenyl " 4-phenoxyphenyl " 2-phenoxyphenyl 3-CH.sub.3 Ophenyl 3-phenoxyphenyl " 4-phenoxyphenyl " 2-phenoxyphenyl 3-NO.sub.2 phenyl 3-phenoxyphenyl " 4-phenoxyphenyl " 2-phenoxyphenyl 3-CH.sub.3 Sphenyl 3-phenoxyphenyl " 4-phenoxyphenyl " 2-phenoxyphenyl 3-CH.sub.3 SOphenyl 3-phenoxyphenyl " 4-phenoxyphenyl " 2-phenoxyphenyl 3-CH.sub.3 SO.sub.2 phenyl 3-phenoxyphenyl " 4-phenoxyphenyl " 2-phenoxyphenyl 4-CH.sub.3 Ophenyl 3-phenoxyphenyl " 4-phenoxyphenyl " 2-phenoxyphenyl 4-NO.sub.2 phenyl 3-phenoxyphenyl " 4-phenoxyphenyl " 2-phenoxyphenyl 4-CH.sub.3 Sphenyl 3-phenoxyphenyl " 4-phenoxyphenyl " 2-phenoxyphenyl 4-CH.sub.3 SOphenyl 3-phenoxyphenyl " 4-phenoxyphenyl " 2-phenoxyphenyl 4-CH.sub.3 SO.sub.2 phenyl 3-phenoxyphenyl " 4-phenoxyphenyl " 2-phenoxyphenyl 3,4-CH.sub.2 OCH.sub.2 phenyl 3-phenoxyphenyl " 4-phenoxyphenyl " naphth-1-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-CH.sub.2 OCH.sub.2 phenyl naphth-2-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 Phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-CH.sub.2 OCH.sub.2 phenyl 5-methylnaphth-1-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 6-methylnaphth-1-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 7-methylnaphth-1-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 8-methytnaphth-1-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 5-chloronaphth-1-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 6-chloronaphth-1-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 7-chloronaphth-1-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 8-chloronaphth-1-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 5-phenylnaphth-1-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 6-phenylnaphth-1-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 7-phenylnaphth-1-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-OH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 8-phenylnaphth-1-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 5-CH.sub.3 Onaphth-1-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 6-CH.sub.3 Onaphth-1-yl phenyl " 3-CH.sub.3 OPhenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 7-CH.sub.3 Onaphth-1-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 8-CH.sub.3 Onaphth-1-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 5-methylnaphth-2-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 6-methylnaphth-2-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 7-methylnaphth-2-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 8-methylnaphth-2-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 5-chloronaphth-2-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 6-chloronaphth-2-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 7-chloronaphth-2-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 8-chloronaphth-2-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 5-phenylnaphth-2-yl Phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 6-phenylnaphth-2-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 7-phenylnaphth-2-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 8-phenylnaphth-2-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 5-CH.sub.3 Onaphth-2-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 6-CH.sub.3 Onaphth-2-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 pheny " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 7-CH.sub.3 Onaphth-2-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl 8-CH.sub.3 Onaphth-2-yl phenyl " 3-CH.sub.3 Ophenyl " 3-NO.sub.2 phenyl " 3-CH.sub.3 Sphenyl " 3-CH.sub.3 SOphenyl " 3-CH.sub.3 SO.sub.2 phenyl " 4-CH.sub.3 Ophenyl " 4-NO.sub.2 phenyl " 4-CH.sub.3 Sphenyl " 4-CH.sub.3 SOphenyl " 4-CH.sub.3 SO.sub.2 phenyl " 3,4-OCH.sub.2 Ophenyl ______________________________________
A compound of formula I, selected from the group consisting of:
- 6-(4-chlorophenyl)sulfinyl!-2,3-dihydro-2-(4-methoxyphenyl)-5 -methyl-3-oxo-pyridazinecarbonitrile;
- 6-(4-chlorophenyl)sulfonyl!-2,3- dihydro-2- (4-methoxyphenyl) -5-methyl -3-oxo-pyridazinecarbonitrile;
- 6-(4-chlorophenyl)thio!-2,3-dihydro-2-(4-hydroxyphenyl)-5-methyl-oxo-4-pyr idazinecarbonitrile;
- 6-(4-chlorophenyl)thio!-2,3-dihydro-2-(4-ethoxyphenyl)-5-methyl-oxo-4-pyri dazinecarbonitrile;
- 6-(3-chlorophenyl)thio!-2,3-dihydro -2-(4-methoxyphenyl)-5-methyl-oxo-4-pyridazinecarbonitrile;
- 6-(3,4-dichlorophenyl)thio!-2,3-dihydro-2-(4-methoxyphenyl)-5-methyl-3-oxo -pyridazinecarbonitrile;
- 6-(4-methoxyphenyl)thio!-2,3-dihydro-2-(4-methoxyphenyl)-5-methyl-3-pyrida zinecarbonitrile;
- 6-(4-nitrophenyl)thio!2,3-dihydro-2-(4-methoxyphenyl)-5-methyl-3-oxo-4-pyr idazinecarbonitrile;
- 6-(4-fluorophenyl)thio!-2,3-dihydro-2-(4-methoxyphenyl)-5-methyl-3-oxo-4-p yridazinecarbonitrile;
- 6-(4-trifluorophenyl)thio!-2,3-dihydro-2-(4-methoxyphenyl)-5-methyl-3-oxo- 4-pyridazinecarbonitrile;
- 6-(3,5- dicloro-phenyl)thio!-2,3-dihydro-2-(4-methoxyphenyl)-5-methyl-3-oxo-4-pyri dazinecarbonitrile;
- 6-(3-methoxyphenyl)thio!-2,3-dihydro-2-(4-methoxyphenyl)-5-methyl-3-oxo-4- pyridazinecarbonitrile;
- 6-(3,4-dimethoxyphenyl)thio!-2,3-dihydro-2-(4-methoxyphenyl)-5-methyl-3-ox o-4-pyridazinecarbonitrile;
- 6-(4-trifluoromethoxyphenyl)thio!-2,3-dihydro-2-(4-methoxyphenyl)-5-methyl -3-oxo-4-pyridazinecarbonitrile;
- 6-(4-cyanophenyl)thio!-2,3-dihydro-2-(4-methoxyphenyl)-5-methyl-3-oxo-4-py ridazinecarbonitrile;
- 6-(4-methylthiophenyl)thio!-2,3-dihydro-2-(4-methoxyphenyl)-5-methyl-3-oxo -4-pyridazinecarbonitrile;
- 6-(4-methylsulfinylphenyl)thio!-2,3-dihydro-2-(4-methoxyphenyl)-5-methyl-3 -oxo-4-pyridazinecarbonitrile;
- 6-(4-phenylphenyl)thio!-2,3-dihydro-2-(3-methoxyphenyl)-5-methyl-3-oxo-4-p yridazinecarbonitrile;
- 6-(4-chlorophenyl)thio!-2,3-dihydro-2-(4-methoxyphenyl)-5-methyl-3-oxo-4-p yridazinecarbonitrile;
- 6-(4-chlorophenyl)thio!-2,3-dihydro-2-(4-phenoxyphenyl)-5-methyl-3-oxo-4-p yridazinecarbonitrile;
- 6-(4-chlorophenyl)thio!-2,3-dihydro-2-(4-methylsulfonylphenyl)-5-methyl-3- oxo-4-pyridazinecarbonitrile;
- 6-(4-chlorophenyl)thio!-2,3-dihydro-2-(4-methylenedioxyphenyl)-5-methyl-3- oxo-4-pyridazinecarbonitrile;
- 6-(4-chlorophenyl)thio!-2,3-dihydro-2-(4-methylthiophenyl)-5-methyl-3-oxo- 4-pyridazinecarbonitrile;
- 6-(4-chlorophenyl)thio!-2,3-dihydro-2-(4-butoxyphenyl)-5-methyl-3-oxo-4-py ridazinecarbonitrile;
21 more elements
Dependencies are inferred from the claim text.