Patent US4017629A successfully refreshed from Google Patents.
US4017629A
Expired / Lapsed
US
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Certain 1,4-dihydro-3-sulfinyl or sulfonyl-pyridines
Assignee: Novartis Corp
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Filing: 1975-05-28
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Granted: 1977-04-12
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Expires: 1995-05-28
Abstract
Abstract The present invention relates to 1,4-dihydropyridines of the formula I ##STR1## and their tautomers, wherein R 1 represents an aryl radical, R 2 and R 3 independently of one another represents hydrogen or a hydrocarbon radical, R 4 represents an alkyl, aryl or aralkyl radical, R 5 denotes an alkoxy radical, which is optionally substituted by an amino group, or denotes an amino group and n is 1 or 2, especially to the 2,6-dimethyl-3-carbomethoxy-5-methylsulphonyl-4-(2-trifluoromethylphenyl)-1,4-dihydro-pyridine and to the 2,6-dimethyl-3-carbomethoxy-5-methylsulphonyl-4-(2-nitrophenyl)-1,4-dihydropyridine. They have an antihypertensive activity.
Inventors
- 👤 Ernst Habicht
- 👤 Hans Kuhnis
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 08:36
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/80; C07D211/84; A; A61; A61P; A61P9/00; A61P9/08; A61P9/12; C07D211/02; C07D211/90
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
98 words
A 1,4-dihydropyridine compound of the formula I ##STR13##and their tautomers, wherein R.sub. 1 is unsubstituted phenyl or phenyl substituted by 1 or 2 identical or different substituents selected from the group consisting of nitro, trifluoromethyl, cyano, azido, lower alkanoyl, sulphamoyl, N-(C.sub. 1-4) alkylsulphamoyl, N,N-di(C.sub. 1-4)-alkylsulphamoyl, R.sub. 2 and R.sub. 3 independently of one another represent hydrogen, phenyl, phenyl-(C.sub. 1-4)-alkyl or (C.sub. 1-7)-alkyl, R.sub. 4 represents (C.sub. 1-7)-alkyl or unsubstituted phenyl or phenyl substituted by (C.sub. 1-4)-alkyl, (C.sub. 1-4)-alkoxy, halogen or trifluoromethyl, R.sub. 5 represents (C.sub. 1-4)-lower alkoxy, amino, mono- or di-(C.sub. 1-4)-alkylamino, and n is 1 or 2.
Claim 2
Dependent Claim
98 words
A 1,4-dihydropyridine compound of the formula I ##STR13##and their tautomers, wherein R.sub. 1 is unsubstituted phenyl or phenyl substituted by 1 or 2 identical or different substituents selected from the group consisting of nitro, trifluoromethyl, cyano, azido, lower alkanoyl, sulphamoyl, N-(C.sub. 1-4) alkylsulphamoyl, N,N-di(C.sub. 1-4)-alkylsulphamoyl, R.sub. 2 and R.sub. 3 independently of one another represent hydrogen, phenyl, phenyl-(C.sub. 1-4)-alkyl or (C.sub. 1-7)-alkyl, R.sub. 4 represents (C.sub. 1-7)-alkyl or unsubstituted phenyl or phenyl substituted by (C.sub. 1-4)-alkyl, (C.sub. 1-4)-alkoxy, halogen or trifluoromethyl, R.sub. 5 represents (C.sub. 1-4)-lower alkoxy, amino, mono- or di-(C.sub. 1-4)-alkylamino, and n is 1 or 2.
Claim 3
Dependent Claim
98 words
The 1,4-dihydropyridines as claimed in claim 1 of the formula I, wherein R.sub. 1 represents a phenyl radical which is substituted by 1 or 2 identical or different substituents from the group nitro, trifluoromethyl, cyano, azido, lower alkanoyl, sulphamoyl, N-(C.sub. 1-4)-alkylsulphamoyl, N,N-di-(C.sub. 1-4)-alkylsulphamoyl, at least one of the substituents being in the orthoposition, R.sub. 2 and R.sub. 3 independently of one another represent hydrogen, phenyl or (C.sub. 1-4)-alkyl, R.sub. 4 represents (C.sub. 1-7)-alkyl, phenyl, (C.sub. 1-4)-alkylphenyl, (C.sub. 1-4)-alkoxyphenyl, halogenophenyl or trifluoromethylphenyl, R.sub. 5 represents amino, mono- or di-(C.sub. 1-4)-alkylamino or (C.sub. 1-4)-alkoxy, and n is 1 or 2.
Claim 4
Dependent Claim
93 words
The 1,4-dihydropyridines as claimed in claim 1 of the formula I, wherein R.sub. 1 represents a phenyl radical which is substituted by 1 or 2 identical or different substituents from the group nitro, trifluoromethyl, cyano, azido, (C.sub. 1-4)-lower alkanoyl, sulphamoyl, N-(C.sub. 1-4)-alkylsulphamoyl and N,N-(C.sub. 1-4)-dialkylsulphamoyl, at least one of the substituents being in the ortho-position, R.sub. 2 and R.sub. 3 independently of one another represent hydrogen or (C.sub. 1-4)-alkyl, R.sub. 4 represents (C.sub. 1-4)-alkyl or phenyl, R.sub. 5 represents amino, mono- or di-(C.sub. 1-4)-alkylamino or (C.sub. 1-4)-alkoxy and n is 1 or 2.
Claim 5
Dependent Claim
94 words
The 1,4-dihydropyridines as claimed in claim 2 of the formula I, wherein R.sub. 1 represents a phenyl radical which is substituted by 1 or 2 identical or different substituents from the group nitro, trifluoromethyl, cyano, azido, (C.sub. 1-4)-lower alkanoyl, sulphamoyl, N-(C.sub. 1-4)-alkylsulphamoyl and N,N-(C.sub. 1-4)-dialkylsulphamoyl, at least one of the substituents being in the ortho-position, R.sub. 2 and R.sub. 3 independently of one another represent hydrogen, (C.sub. 1-4)-alkyl or phenyl, R.sub. 4 represents (C.sub. 1-4)-alkyl or phenyl, R.sub. 5 represents amino- mono- or di-(C.sub. 1-4)-alkylamino, or (C.sub. 1-4)-alkoxy and n is 1 or 2.
Claim 6
Dependent Claim
72 words
The 1,4-dihydropyridines of the claim 1, wherein R.sub. 1 denotes a phenyl radical which is substituted in the ortho position by nitro, trifluoromethyl, cyano, azido, (C.sub. 1-4)-lower alkanoyl, sulphamoyl, N-(C.sub. 1-3)-alkylsulphamoyl or N,N-di-(C.sub. 1-3)-alkylsulphamoyl, R.sub. 2 and R.sub. 3 independently of one another represent hydrogen or (C.sub. 1-4)-alkyl, R.sub. 4 represents (C.sub. 1-4)-alkyl, R.sub. 5 represents amino, (C.sub. 1-4)-lower alkylamino, (C.sub. 1-4)-di-lower alkylamino or (C.sub. 1-4)-alkoxy and n is 1 or 2.
Claim 7
Dependent Claim
80 words
The 1,4-dihydropyridines as claimed in claim 2 of the formula I, wherein R.sub. 1 denotes a phenyl radical which is substituted in the ortho-position by cyano, azido, (C.sub. 1-4)-lower alkanoyl, sulphamoyl, N-(C.sub. 1-3)-alkylsulphamoyl, nitro, trifluoromethyl or N,N-di-(C.sub. 1-3)-alkylsulphamoyl, R.sub. 2 and R.sub. 3 independently of one another represent hydrogen, (C.sub. 1-4)-alkyl or phenyl, R.sub. 4 represents (C.sub. 1-4)-alkyl or phenyl, R.sub. 5 represents amino, (C.sub. 1-4)-lower alkylamino, di-(C 1-4 )-lower alkylamino, (C 1-4 )-alkoxy and n is 1 or 2.
Claim 8
Dependent Claim
61 words
The 1,4-dihydropyridines as claimed in claim 2 of the formula I, wherein R.sub. 1 denotes a phenyl radical which is substituted in the ortho-position by nitro, trifluoromethyl or N,N-di-(C.sub. 1-3)-alkylsulphamoyl, R.sub. 2 and R.sub. 3 independently of one another represent hydrogen, (C.sub. 1-4)-alkyl or phenyl, R.sub. 4 represents (C.sub. 1-4)-alkyl or phenyl, R.sub. 5 represents (C.sub. 1-4)-alkoxy, and n is 2.
Claim 9
Dependent Claim
63 words
The 1,4-dihydropyridines of the claim 1 wherein R.sub. 1 denotes a phenyl radical which is substituted in the orthoposition by nitro, trifluoromethyl, cyano, acetyl or sulphamoyl, R.sub. 2 and R.sub. 3 independently of one another denote hydrogen, methyl or ethyl, R.sub. 4 represents methyl or ethyl, R.sub. 5 represents amino, methylamino or dimethylamino or methoxy or ethoxy and n is 1 or 2.
Claim 10
Dependent Claim
69 words
The 1,4-dihydropyridines as claimed in claim 2 of the formula I, wherein R.sub. 1 denotes a phenyl radical which is substituted in the ortho-position by cyano, acetyl, sulphamoyl, nitro, trifluoromethyl or N,N-di-(C.sub. 1-3)-alkylsulphamoyl, R.sub. 2 and R.sub. 3 independently of one another denote hydrogen, methyl, ethyl or phenyl, R.sub. 4 represents methyl, ethyl or phenyl, R.sub. 5 represents amino, methylamino, dimethylamino, methoxy, ethoxy, and n is 1 or 2.
Claim 11
Dependent Claim
61 words
The 1,4-dihydropyridines as claimed in claim 2 of the formula I, wherein R.sub. 1 denotes a phenyl radical which is substituted in the ortho-position by nitro, trifluoromethyl or N,N-di-(C.sub. 1-3)-alkylsulphamoyl, R.sub. 2 and R.sub. 3 independently of one another denote hydrogen, methyl, ethyl or phenyl, R.sub. 4 represents methyl, ethyl or phenyl, R.sub. 5 represents methoxy, ethoxy, and n is 2.
Claim 12
Dependent Claim
11 words
A compound selected from the group consisting of 2,6-Dimethyl-3-carbomethoxy-5-methylsulphonyl-4-(2-trifluoromethylphenyl)-1,4-dihydropyridine and 2,6-dimethyl-3-carbomethoxy-5-methylsulphonyl-4-(2-nitrophenyl)-1,4-dihydropyridine.
Claim 13
Dependent Claim
11 words
A compound selected from the group consisting of 2,6-Dimethyl-3-carbomethoxy-5-methylsulphonyl-4-(2-trifluoromethylphenyl)-1,4-dihydropyridine and 2,6-dimethyl-3-carbomethoxy-5-methylsulphonyl-4-(2-nitrophenyl)-1,4-dihydropyridine.
Claim 14
Dependent Claim
1 words
2,6-Dimethyl-3-carbomethoxy-5-methylsulphonyl-4-(2-dimethylsulphamoyl-phenyl)-1,4-dihydropyridine.
Claim 15
Dependent Claim
1 words
2,6-Dimethyl-3-carbomethoxy-5-methylsulphonyl-4-(2-dimethylsulphamoyl-phenyl)-1,4-dihydropyridine.
Claim 16
Dependent Claim
11 words
A compound selected from the group consisting of 2,6-Dimethyl-3-(2-dimethylamino)-carboethoxy-4-(2-nitrophenyl-5-methylsulphonyl-1,4-dihydropyridine and 2,6-dimethyl-3-carbo-t.-butoxy-4-(2-nitrophenyl)-5-methylsulphonyl-1,4-dihydropyridine.
Claim 17
Dependent Claim
11 words
A compound selected from the group consisting of 2,6-Dimethyl-3-(2-dimethylamino)-carboethoxy-4-(2-nitrophenyl-5-methylsulphonyl-1,4-dihydropyridine and 2,6-dimethyl-3-carbo-t.-butoxy-4-(2-nitrophenyl)-5-methylsulphonyl-1,4-dihydropyridine.
Claim 18
Dependent Claim
3 words
2-Methyl-3-carbomethoxy-4-(2-nitrophenyl)-5-methyl-sulphonyl-6-phenyl-1,4-dihydropyridine or 2,6-dimethyl-3-carbomethoxy-4-(2-nitrophenyl)-5-phenylsulphonyl-1,4-dihydropyridine.
Claim 19
Dependent Claim
3 words
2-Methyl-3-carbomethoxy-4-(2-nitrophenyl)-5-methyl-sulphonyl-6-phenyl-1,4-dihydropyridine or 2,6-dimethyl-3-carbomethoxy-4-(2-nitrophenyl)-5-phenylsulphonyl-1,4-dihydropyridine.
Claim 20
Dependent Claim
27 words
A pharmaceutical preparation useful for the treatment of hypertension which comprises an antihypertensively effective amount of a compound of claim 1 together with a therapeutically usable excipient.
References Cited (Backward Citations)
US3867393A
Cited
US3883540A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-04-11 | 1980-10-11 | 1981-04-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-04-11 | 1984-10-11 | 1985-04-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-04-11 | 1988-10-11 | 1989-04-12 | $7700.00 | Window Closed / Lapsed |