US4663334A
Expired / Lapsed
US
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Heteroaromatic acetylenes useful as antihypertensive agents
Assignee: Janssen Pharmaceuticals Inc
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Filing: 1985-12-11
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Granted: 1987-05-05
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Expires: 2005-12-11
Abstract
Abstract Heterocyclic acetylenes of the formula (I): ##STR1## wherein Y is alkyl, alkoxy, alkoxyalkyl, chloro, fluoro, bromo or carboxamidoalkyl and R 1 is hydrogen, alkyl, alkoxy, alkylthio, alkoxycarbonyl, chloro, fluoro or dialkylamino, m is 0-2, R 2 is branched alkyl and Het is an aromatic heterocycle. The acetylenes are useful in treating hypertension and/or angina.
Inventors
- 👤 John R. Carson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 07:35
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/28; C07D213/30; A; A61; A61P; A61P9/00; A61P9/12; C07D209/00; C07D209/02; C07D209/04; C07D209/30; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07D239/00; C07D239/02; C07D239/24; C07D239/26; C07D241/00; C07D241/02; C07D241/10; C07D241/12; C07D307/00; C07D307/02; C07D307/34; C07D307/56; C07D307/68; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/14; C07D333/16
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
129 words
A heteraromatic acetylene of the following formula (I): ##STR5## wherein Y is alkyl of about 1 to 6 carbons, alkoxy of about 1 to 6 carbons, alkoxyalkyl of about 2 to 8 carbons, chloro, fluoro, bromo or carboxamidoalkyl of about 2 to 7 carbons; m is 0, 1 or 2; R 1 is hydrogen, alkyl of about 1 to 6 carbons, alkoxy of about 1 to 6 carbons, alkylthio of about 1 to 6 carbons, alkoxycarbonyl of about 2 to 7 carbons, chloro, fluoro or dialkylamino of about 2 to 8 carbons; R 2 is branched chain alkyl of about 3 to 7 carbons with the carbon alpha to the nitrogen atom being branched; and Het is pyridinyl, pyrrolyl or pyrazolyl; and the pharmaceutically acceptable acid addition salts thereof.
Claim 2
Dependent Claim
129 words
A heteraromatic acetylene of the following formula (I): ##STR5## wherein Y is alkyl of about 1 to 6 carbons, alkoxy of about 1 to 6 carbons, alkoxyalkyl of about 2 to 8 carbons, chloro, fluoro, bromo or carboxamidoalkyl of about 2 to 7 carbons; m is 0, 1 or 2; R 1 is hydrogen, alkyl of about 1 to 6 carbons, alkoxy of about 1 to 6 carbons, alkylthio of about 1 to 6 carbons, alkoxycarbonyl of about 2 to 7 carbons, chloro, fluoro or dialkylamino of about 2 to 8 carbons; R 2 is branched chain alkyl of about 3 to 7 carbons with the carbon alpha to the nitrogen atom being branched; and Het is pyridinyl, pyrrolyl or pyrazolyl; and the pharmaceutically acceptable acid addition salts thereof.
Claim 3
Dependent Claim
9 words
The acetylene of claim 1, wherein Het is 2-pyridinyl.
Claim 4
Dependent Claim
9 words
The acetylene of claim 2, wherein Het is pyrrolyl.
Claim 5
Dependent Claim
11 words
The acetylene of claim 1, wherein Het is 3- or 4-pyridinyl.
Claim 6
Dependent Claim
9 words
The acetylene of claim 1, wherein Het is 3-pyridinyl.
Claim 7
Dependent Claim
9 words
The acetylene of claim 1, wherein Het is 4-pyridinyl.
Claim 8
Dependent Claim
9 words
The acetylene of claim 1, wherein Het is pyrazolyl.
Claim 9
Dependent Claim
13 words
The acetylene of claim 1, wherein R 2 is iso-propyl, sec-butyl or tert-butyl.
Claim 10
Dependent Claim
10 words
The acetylene of claim 1, wherein R 1 is hydrogen.
Claim 11
Dependent Claim
9 words
The acetylene of claim 1, wherein m is 0.
Claim 12
Dependent Claim
14 words
The acetylene of claim 1, wherein m is 0; and R 1 is hydrogen.
Claim 13
Dependent Claim
28 words
The acetylene of claim 1, wherein said acetylene is selected from the group consisting of: 1-[(1,1-dimethylethyl)amino]-3-[2-(4-pyridinylethynyl)phenoxy]-2-propanol; 1-[(1,1-dimethylethyl)amino]-3-[2-(3-pyridinylethynyl)phenoxy]-2-propanol; 1-[(1,1-dimethylethyl)amino]-3-[2-(2-pyridinylethynyl)phenoxy]-2-propanol; 1-[(1-methylethyl)amino]-3-[2-(4-pyridinylethynyl)phenoxy]-2-propanol; and 1-[(1,1-dimethylethyl)amino]-3-[2-(4-pyrazolylethynyl)phenoxy-2-propanol, and their pharmaceutically acceptable acid addition salts.
Claim 14
Dependent Claim
18 words
The acetylene of claim 1, wherein said acetylene is 1-[(1,1-dimethylethyl)amino]-3-[2-(4-pyridinylethynyl)phenoxy]-2-propanol or a pharmaceutically acceptable acid addition salt thereof.
Claim 15
Dependent Claim
18 words
The acetylene of claim 1, wherein said acetylene is 1-[(1,1-dimethylethyl)amino]-3-[2-(3-pyridinylethynyl)phenoxy]-2-propanol or a pharmaceutically acceptable acid addition salt thereof.
Claim 16
Dependent Claim
61 words
The acetylene of claim 1, wherein said acid-addition salt is a salt with an acid selected from the group consisting of hydrochloric, hydrobromic, hydroiodic, perchloric, sulfuric, nitric, a phosphoric, acetic, propionic, glycolic, lactic, pyruvic, malonic, succinic, maleic, fumaric, malic, tartaric, citric, benzoic, cinnamic, mandelic, methanesulfonic, ethanesulfonic, hydroxyethanesulfonic, benzenesulfonic, p-toluene sulfonic, cyclohexanesulfamic, salicylic, p-aminosalicylic, 2-phenoxybenzoic, 2-acetoxybenzoic or a salt made with saccharin.
Claim 17
Dependent Claim
21 words
An antihypertensive pharmaceutical composition comprising an antihypertensive amount of an acetylene of claim 1 and a pharmaceutically acceptable diluent or carrier.
Claim 18
Dependent Claim
20 words
A method of treating hypertension in a mammal which comprises administering to the mammal, the pharmaceutical composition of claim 16.
Claim 19
Dependent Claim
11 words
The method of claim 17, wherein said mammal is a human.
Claim 20
Dependent Claim
140 words
An acetylene of the following formula (IX): ##STR6## wherein Y is alkyl of about 1 to 6 carbons, alkoxy of about 1 to 6 carbons, alkoxyalkyl of about 2 to 8 carbons, chloro, fluoro, bromo or carboxamidoalkyl of about 2 to 7 carbons; m is 0, 1 or 2; R 1 is hydrogen, alkyl of about 1 to 6 carbons, alkoxy of about 1 to 6 carbons, alkylthio of about 1 to 6 carbons, alkoxycarbonyl of about 2 to 7 carbons, chloro, fluoro or dialkylamino of about 2 to 8 carbons; R 2 is branched chain alkyl of about 3 to 7 carbons with the carbon alpha to the nitrogen atom being branched; and Het is pyridinyl pyrrolyl or pyrazolyl; and R 3 is a alkanoyl of 2-6 carbon atoms or trialkylsilyl protecting group, and the acid addition salts thereof.
Claim 21
Dependent Claim
140 words
An acetylene of the following formula (IX): ##STR6## wherein Y is alkyl of about 1 to 6 carbons, alkoxy of about 1 to 6 carbons, alkoxyalkyl of about 2 to 8 carbons, chloro, fluoro, bromo or carboxamidoalkyl of about 2 to 7 carbons; m is 0, 1 or 2; R 1 is hydrogen, alkyl of about 1 to 6 carbons, alkoxy of about 1 to 6 carbons, alkylthio of about 1 to 6 carbons, alkoxycarbonyl of about 2 to 7 carbons, chloro, fluoro or dialkylamino of about 2 to 8 carbons; R 2 is branched chain alkyl of about 3 to 7 carbons with the carbon alpha to the nitrogen atom being branched; and Het is pyridinyl pyrrolyl or pyrazolyl; and R 3 is a alkanoyl of 2-6 carbon atoms or trialkylsilyl protecting group, and the acid addition salts thereof.
Claim 22
Dependent Claim
13 words
The acetylene of claim 19, wherein R 3 is acetyl, propionyl or butyryl.
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1990-05-04 | 1990-11-03 | 1991-05-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-05-04 | 1994-11-03 | 1995-05-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-05-04 | 1998-11-03 | 1999-05-05 | $7700.00 | Window Closed / Lapsed |