US4356178A
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3,4-(Bis-substituted)-1,2,5-oxdiazole 2-oxides, their use and pharmaceutical formulations containing them
Assignee: Sanofi Aventis Deutschland GmbH
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Filing: 1981-12-18
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Granted: 1982-10-26
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Expires: 2001-12-18
Abstract
Abstract Pharmacologically-valuable 3,4-(bis-substituted)-1,2,5-oxdiazole 2-oxides of formula I <IMAGE> (I) [wherein R denotes -NHR1, -NR2R3, -NHR4OR2, -NHR5COR6 or <IMAGE> R1 denotes alkyl having from 1 to 6 C atoms or cycloalkyl having 4 to 7 ring C atoms, R2 and R3 denote alkyl having from 1 to 4 C atoms, R4 denotes an alkylene radical of the formula -CnH2n-(wherein n denotes 2, 3 or 4), R5 denotes an alkylene radical of the formula -CmH2m- (wherein m denotes 1, 2 or 3), R6 denotes -OR2, -NHR1, -NR2R3 or -NH2, X denotes -(CH2)p-, -(CH2)2-O-(CH2)2- or <IMAGE> and p is 4, 5 of 6] and their pharmacologically-acceptable acid-addition compounds are prepared by elimination of hydrogen chloride from a hydroxamoyl chloride of the formula R-CO-C(Cl)=NOH (II) and dimerization. If desired, the resulting reaction product is subsequently converted into an acid-addition compound. The compounds and pharmaceutical preparations thereof are useful for treating and for prophylaxis of cardiovascular diseases.
Inventors
- 👤 Karl Schonafinger
- 👤 Rudi Beyerle
- 👤 Anton Mogilev
- 👤 Helmut Bohn
- 👤 Melitta Just
- 👤 Piero A. Martorana
- 👤 Rolf-Eberhard Nitz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 20:20
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/70; A61K31/7028; A61K31/7034; A61K31/704; A61K31/33; A61K31/395; A61K31/41; A61K31/42; A61K31/435; A61K31/47; A61K31/475; A61K31/495; A61K31/50; A61K31/505; A61K31/54; A61K31/55; A61P; A61P9/00; A61P9/08; A61P9/10; A61P9/12; C; C07; C07D; C07D271/00; C07D271/02; C07D271/08
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
161 words
A 3,4-(bis-substituted)-1,2,5-oxdiazole 2-oxide of the formula ##STR17## wherein R is --NHR 1 , --NR 2 R 3 , --NHR 4 OR 2 , --NHR 5 COR 6 or ##STR18## R 1 is alkyl having from 1 to 6 carbon atoms or cycloalkyl having from 4 to 7 ring carbon atoms; each of R 2 and R 3 is, independently, alkyl having from 1 to 4 carbon atoms; R 4 is alkylene of the formula --C n H 2n --; R 5 is alkylene of the formula --C m H 2m --; R 6 is --OR 2 , --NHR 1 , --NR 2 R 3 or --NH 2 ; X is --(CH 2 ) p --, --(CH 2 ) 2 --O--(CH 2 ) 2 -- or --(CH 2 ) 2 --N(R 2 )--(CH 2 ) 2 --; m is 1, 2 or 3; n is 2, 3 or 4; and p is 4, 5 or 6; or a pharmacologically-acceptable acid-addition salt thereof.
Claim 2
Dependent Claim
161 words
A 3,4-(bis-substituted)-1,2,5-oxdiazole 2-oxide of the formula ##STR17## wherein R is --NHR 1 , --NR 2 R 3 , --NHR 4 OR 2 , --NHR 5 COR 6 or ##STR18## R 1 is alkyl having from 1 to 6 carbon atoms or cycloalkyl having from 4 to 7 ring carbon atoms; each of R 2 and R 3 is, independently, alkyl having from 1 to 4 carbon atoms; R 4 is alkylene of the formula --C n H 2n --; R 5 is alkylene of the formula --C m H 2m --; R 6 is --OR 2 , --NHR 1 , --NR 2 R 3 or --NH 2 ; X is --(CH 2 ) p --, --(CH 2 ) 2 --O--(CH 2 ) 2 -- or --(CH 2 ) 2 --N(R 2 )--(CH 2 ) 2 --; m is 1, 2 or 3; n is 2, 3 or 4; and p is 4, 5 or 6; or a pharmacologically-acceptable acid-addition salt thereof.
Claim 3
Dependent Claim
12 words
A compound according to claim 1 wherein R is --NHR 1 .
Claim 4
Dependent Claim
14 words
A compound according to claim 1 wherein R is --NR 2 R 3 .
Claim 5
Dependent Claim
14 words
A compound according to claim 1 wherein R is --NHR 4 OR 2 .
Claim 6
Dependent Claim
14 words
A compound according to claim 1 wherein R is --NHR 5 COR 6 .
Claim 7
Dependent Claim
10 words
A compound according to claim 1 wherein R is ##STR19##
Claim 8
Dependent Claim
14 words
A compound according to claim 6 wherein X is --(CH 2 ) p --.
Claim 9
Dependent Claim
18 words
A compound according to claim 6 wherein X is --(CH 2 ) 2 --O--(CH 2 ) 2 --.
Claim 10
Dependent Claim
18 words
A compound according to claim 6 wherein X is --(CH 2 )--N(R 2 )--(CH 2 ) 2 --.
Claim 11
Dependent Claim
12 words
A compound according to claim 1 wherein R contains an --NH-- grouping.
Claim 12
Dependent Claim
21 words
A compound according to claim 1 wherein R 4 is --(CH 2 ) 2 -- or --(CH 2 ) 3 --.
Claim 13
Dependent Claim
19 words
A compound according to claim 1 wherein R 5 is --CH 2 -- or --(CH 2 ) 2 --.
Claim 14
Dependent Claim
13 words
A compound according to claim 1 wherein R 2 is methyl or ethyl.
Claim 15
Independent Claim
40 words
A method for treating or for prophylaxis of human cardiovascular-system disease which comprises administering an effective amount of a compound according to one of claims 1 and 10 to 13 to a human afflicted with or prone to such disease.
Claim 16
Dependent Claim
37 words
A pharmaceutical formulation of active ingredient and pharmacologically-compatible excipient, the active ingredient comprising a compound according to one of claims 1 and 10 to 13 in an amount of from 0.1 to 50 milligrams per unit dose.
Claim 17
Dependent Claim
39 words
A pharmaceutical formulation for treating or for prophylaxis of cardiovascular system disease which comprises a combination of pharmacologically-compatible excipient with an effective amount per unit dose of a compound according to one of claims 1 and 10 to 13.
References Cited (Backward Citations)
US4089867A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-10-25 | 1986-04-26 | 1986-10-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-10-25 | 1990-04-26 | 1990-10-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-10-25 | 1994-04-26 | 1994-10-26 | $7700.00 | Window Closed / Lapsed |