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US4563446A
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Thromboxane synthetase inhibiting 3-(1-alkenyl) pyridines
Assignee: Takeda Pharmaceutical Co Ltd
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Filing: 1984-07-19
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Granted: 1986-01-07
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Expires: 2004-07-19
Abstract
Abstract Novel compounds of the formula: ##STR1## wherein R 2 is an aromatic or heterocyclic group, which may optionally be substituted, R 2 is a methyl group, a hydroxymethyl group, a nitroxymethyl group, a formyl group, a nitrogen-containing five-membered ring-methyl group, an acetal-methyl group, a trialkylsilyloxymethyl group, an alkyl- or aryl-sulfonyloxymethyl group, an alkyl- or aryl-sulfonylaminocarbonyloxymethyl group, an acyloxymethyl group, an alkoxycarbonyloxymethyl group, a halogenomethyl group, an alkoxymethyl group, an aryloxymethyl group, a cyano group, a carbamoyl group which may optionally be substituted, a carbamoyloxymethyl group which may optionally be substituted, a thiocarbamoyloxymethyl group which may optionally be substituted, and an alkoxycarbonyl group, n is an integer of 1 to 20, and ##STR2## provided that n is an integer of 9 to 20 when ##STR3## and, at the same time, R 2 is a carboxyl group or an alkoxycarbonyl group, or a pharmacologically acceptable salt thereof, have a selective inhibitory action on biosynthesis of thromboxane A 2 (TXA 2 ) and an effect of enhancing the production of prostaglandin I 2 (PGI 2 ), and can be used for mammals to prevent and treat arterial thrombosis caused by platelet aggregation or ischemic diseases caused by vasospasms in cardiac, cerebral and peripheral circulatory system (e.g. cardiac infarction, stroke, occlusion of blood vessels in kidney, lung and other organs, pectic ulcer, etc.).
Inventors
- 👤 Shinji Terao
- 👤 Kohei Nishikawa
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 18:32
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/06; C07D213/16; C07D213/24; C07D213/26; C07D213/28; C07D213/30; C07D213/44; C07D213/46; C07D213/48; C07D213/54; C07D213/55; C07D213/56; C07D213/57; C07D213/60; C07D213/78; C07D213/79; C07D213/80; C07D213/89; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08; C07D405/00; C07D405/02; C07D405/06; C07D409/00; C07D409/02; C07D409/06; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
150 words
A compound of the structural formula ##STR143## wherein R 1 is phenyl, methylenedioxyphenyl or thienyl, R 2 is methyl, hydroxymethyl, nitroxymethyl, formyl, imidazolylmethyl, triazolylmethyl, tetrazolylmethyl, acetal-methyl having 2 to 7 carbon atoms, trialkylsilyloxymethyl having 4 to 10 carbon atoms, C 1-3 alkyl-sulfonyloxymethyl, phenyl-sulfonyloxymethyl, tolylsulfonyloxymethyl, methanesulfonylaminocarbonyloxymethyl, p-toluenesulfonylaminocarbonyloxymethyl, formyloxymethyl, C 1-6 alkyl-carbonyloxymethyl, pyridylcarbonyloxymethyl alkoxycarbonyloxymethyl having 3 to 8 carbon atoms, halogenomethyl, alkoxymethyl having 2 to 5 carbon atoms, aryloxymethyl, cyano, carbamoyl, mono- or di-(C 1-6 )alkyl-aminocarbonyl, mono- or di-arylaminocarbonyl, carbamoyloxymethyl, mono- or di-( 1-6 )alkyl-aminocarbonyloxymethyl, mono- or di-aryl-aminocarbonyloxymethyl, thiocarbonyloxymethyl, mono- or di-( 1-6 )alkyl-aminothiocarbonyloxymethyl, mono- or di-arylaminothiocarbonyloxymethyl, alkoxycarbonyl having 2 to 5 carbon atoms, carboxyl, wherein the aryl moieties represent phenyl, tolyl, or xylyl, ##STR144## and n is an integer of 1 to 20, provided that n is 9 to 20 when ##STR145## and, at the same time R 2 is a carboxy or alkoxycarbonyl group, or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
150 words
A compound of the structural formula ##STR143## wherein R 1 is phenyl, methylenedioxyphenyl or thienyl, R 2 is methyl, hydroxymethyl, nitroxymethyl, formyl, imidazolylmethyl, triazolylmethyl, tetrazolylmethyl, acetal-methyl having 2 to 7 carbon atoms, trialkylsilyloxymethyl having 4 to 10 carbon atoms, C 1-3 alkyl-sulfonyloxymethyl, phenyl-sulfonyloxymethyl, tolylsulfonyloxymethyl, methanesulfonylaminocarbonyloxymethyl, p-toluenesulfonylaminocarbonyloxymethyl, formyloxymethyl, C 1-6 alkyl-carbonyloxymethyl, pyridylcarbonyloxymethyl alkoxycarbonyloxymethyl having 3 to 8 carbon atoms, halogenomethyl, alkoxymethyl having 2 to 5 carbon atoms, aryloxymethyl, cyano, carbamoyl, mono- or di-(C 1-6 )alkyl-aminocarbonyl, mono- or di-arylaminocarbonyl, carbamoyloxymethyl, mono- or di-( 1-6 )alkyl-aminocarbonyloxymethyl, mono- or di-aryl-aminocarbonyloxymethyl, thiocarbonyloxymethyl, mono- or di-( 1-6 )alkyl-aminothiocarbonyloxymethyl, mono- or di-arylaminothiocarbonyloxymethyl, alkoxycarbonyl having 2 to 5 carbon atoms, carboxyl, wherein the aryl moieties represent phenyl, tolyl, or xylyl, ##STR144## and n is an integer of 1 to 20, provided that n is 9 to 20 when ##STR145## and, at the same time R 2 is a carboxy or alkoxycarbonyl group, or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
9 words
A compound as claimed in claim 1 wherein ##STR146##
Claim 4
Dependent Claim
39 words
A compound as claimed in claim 1, wherein R 2 is methyl, hydroxymethyl, nitroxymethyl, formyl, imidazolylmethyl, triazolylmethyl, tetrazolylmethyl, 2-tetrahydropyranyloxymethyl, 2-tetrahydrofuryloxymethyl, dimethyl-tert-butylsilyloxymethyl, methanesulfonyloxymethyl, p-toluenesulfonyloxymethyl, p-toluenesulfonylaminocarbonyloxymethyl, acetoxymethyl, formyloxymethyl, 3-pyridylcarbonyloxymethyl, iodomethyl, methoxymethyl, phenoxymethyl, cyano, carbamoyl, phenylaminocarbonyl, carbamoyloxymethyl, methylaminocarbonyloxymethyl, n-butylaminocarbonyloxymethyl, phenylaminocarbonyloxymethyl, phenylaminothiocarbonyloxymethyl, methoxycarbonyl.
Claim 5
Dependent Claim
21 words
A compound as claimed in claim 1, wherein R 2 is hydroxymethyl, a nitroxymethyl group, a carbamoyl group or carbamoyloxymethyl group.
Claim 6
Dependent Claim
16 words
A compound as claimed in claim 1, wherein n is an integer of 3 to 9.
Claim 7
Dependent Claim
12 words
A compound as claimed in claim 1, wherein the compound is (E)-7-phenyl-7-(3-pyridyl)-6-hepten-1-ol.
Claim 8
Dependent Claim
12 words
A compound as claimed in claim 1, wherein the compound is 1-aminocarbonyloxy-(E)-7-phenyl-7-(3-pyridyl)-6-heptene.
Claim 9
Dependent Claim
12 words
A compound as claimed in claim 1, wherein the compound is 1-phenylaminocarbonyloxy-(E)-7-phenyl-7-(3-pyridyl)-6-heptene.
Claim 10
Dependent Claim
12 words
A compound as claimed in claim 1, wherein the compound is 1-nitroxy-(E)-7-phenyl-7-(3-pyridyl)-6-heptene.
Claim 11
Dependent Claim
12 words
A compound as claimed in claim 1, wherein the compound is (E)-7-phenyl-7-(3-pyridyl)-6-heptenamide.
Claim 12
Dependent Claim
174 words
A pharmaceutical composition suitable for inhibiting activity of thromboxane A 2 synthetase in a mammal, which comprises, as an active ingredient, an effective amount of a compound of the formula ##STR147## wherein R 1 is phenyl, methylenedioxyph or thienyl, R 2 is methyl, hydroxymethyl, nitroxymethyl, formyl, imidazolylmethyl, triazolylmethyl, tetrazolylmethyl, acetal-methyl having 2 to 7 carbon atoms, trialkylsilyloxymethyl having 4 to 10 carbon atoms, C 1-3 alkyl-sulfonyloxymethyl, phenyl-sulfonyloxymethyl, tolylsulfonyloxymethyl, methanesulfonylaminocarbonyloxymethyl, p-toluenesulfonylaminocarbonyloxymethyl, formyloxymethyl, C 1-6 alkyl-carbonyloxymethyl, pyridylcarbonyloxymethyl, alkoxycarbonyloxymethyl having 3 to 8 carbon atoms, halogenomethyl, alkoxymethyl having 2 to 5 carbon atoms, aryloxymethyl, cyano, carbamoyl, mono- or di-(C 1-6 )alkyl-aminocarbonyl, mono- or di-arylaminocarbonyl, carbamoyloxymethyl, mono- or di-( 1-6 )alkyl-aminocarbonyloxymethyl, mono- or di-aryl-aminocarbonyloxymethyl, thiocarbonyloxymethyl, mono- or di-(C 1-6 )alkyl-aminothiocarbonyloxymethyl, mono- or di-arylaminothiocarbonyloxymethyl, alkoxycarbonyl having 2 to 5 carbon atoms, carboxyl, wherein the aryl moieties represent phenyl, tolyl, or xylyl, ##STR148## n is an integer of 1 to 20, provided that n is 9 to 20 ##STR149## and, at the same time R 2 is a carboxy or alkoxycarbonyl group, and a pharmacologically acceptable carrier or excipient thereof.
Claim 13
Dependent Claim
174 words
A pharmaceutical composition suitable for inhibiting activity of thromboxane A 2 synthetase in a mammal, which comprises, as an active ingredient, an effective amount of a compound of the formula ##STR147## wherein R 1 is phenyl, methylenedioxyph or thienyl, R 2 is methyl, hydroxymethyl, nitroxymethyl, formyl, imidazolylmethyl, triazolylmethyl, tetrazolylmethyl, acetal-methyl having 2 to 7 carbon atoms, trialkylsilyloxymethyl having 4 to 10 carbon atoms, C 1-3 alkyl-sulfonyloxymethyl, phenyl-sulfonyloxymethyl, tolylsulfonyloxymethyl, methanesulfonylaminocarbonyloxymethyl, p-toluenesulfonylaminocarbonyloxymethyl, formyloxymethyl, C 1-6 alkyl-carbonyloxymethyl, pyridylcarbonyloxymethyl, alkoxycarbonyloxymethyl having 3 to 8 carbon atoms, halogenomethyl, alkoxymethyl having 2 to 5 carbon atoms, aryloxymethyl, cyano, carbamoyl, mono- or di-(C 1-6 )alkyl-aminocarbonyl, mono- or di-arylaminocarbonyl, carbamoyloxymethyl, mono- or di-( 1-6 )alkyl-aminocarbonyloxymethyl, mono- or di-aryl-aminocarbonyloxymethyl, thiocarbonyloxymethyl, mono- or di-(C 1-6 )alkyl-aminothiocarbonyloxymethyl, mono- or di-arylaminothiocarbonyloxymethyl, alkoxycarbonyl having 2 to 5 carbon atoms, carboxyl, wherein the aryl moieties represent phenyl, tolyl, or xylyl, ##STR148## n is an integer of 1 to 20, provided that n is 9 to 20 ##STR149## and, at the same time R 2 is a carboxy or alkoxycarbonyl group, and a pharmacologically acceptable carrier or excipient thereof.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-01-06 | 1989-07-08 | 1990-01-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-01-06 | 1993-07-08 | 1994-01-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-01-06 | 1997-07-08 | 1998-01-07 | $7700.00 | Window Closed / Lapsed |