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US4748239A Expired / Lapsed US ⏱️ 0.0 years remaining

Benzazepine derivatives

Assignee: ER Squibb and Sons LLC
•
Filing: 1987-04-24
•
Granted: 1988-05-31
•
Expires: 2007-04-24
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Abstract

Abstract Vasodilating activity is exhibited by compounds having the formula <IMAGE> and pharmaceutically acceptable salts thereof.

Inventors

  • 👤 David Floyd
  • 👤 John Krapcho

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 17:21
CPC Classifications
C; C07; C07D; C07D223/00; C07D223/14; C07D223/16; A; A61; A61P; A61P9/00; A61P9/08; A61P9/12

Claims Analysis

Total Claims: 31
Claim 1
Independent Claim 306 words
A compound having the formula ##STR17## or a pharmaceutically acceptable salt thereof wherein R 1 is hydrogen, alkyl, alkanoyl, alkenyl, arylcarbonyl, heteroarylcarbonyl or ##STR18## R 2 and R 3 are each independently hydrogen, alkyl, cycloalkyl or arylalkyl or R 2 and R 3 together with the nitrogen atom to which they are attached are pyrrolidinyl, piperidinyl, or morpholinyl; R 4 and R 5 are each independently hydrogen, halogen, alkyl, alkoxy, aryloxy, arylalkoxy, diarylalkoxy, arylalkyl, cyano, hydroxy, alkanoyloxy, ##STR19## fluoro substituted alkoxy, fluoro substituted alkyl, (cycloalkyl)alkoxy, --NO 2 , --NX 3 X 4 , --S(O) m alkyl, --S(O) m aryl, ##STR20## n is 2 or 3; m is 0, 1 or 2; X 1 and X 2 are each independently hydrogen, alkyl, aryl or heteroaryl, or X 1 and X 2 together with the nitrogen atom to which they are attached are pyrrolidinyl, piperidinyl or morpholinyl; X 3 and X 4 are each independently hydrogen, alkyl, alkanoyl, arylcarbonyl, heteroacrylcarbonyl, or ##STR21## X 5 is hydroxy, alkoxy, aryloxy, amino, alkylamino or dialkylamino; and X 6 is alkyl, alkoxy or aryloxy; with the proviso that if R4 is a 7-alkyl group, it must have a tertiary carbon atom bonded to the ring; wherein the term "aryl" refers to phenyl and phenyl substituted with 1, 2 or 3 amino, alkylamino, dialkylamino, nitro, halogen, hydroxyl, trifluoromethyl, alkyl or 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkanoyloxy, carbamoyl, or carboxyl groups; the term "heteroaryl" refers to pyridinyl, pyrrolyl, imidazolyl, furyl, thienyl, or thiazolyl; the terms "alkyl" and "alkoxy" refers to groups having 1 to 10 carbon atoms; the term "alkenyl" refers to groups having 2 to 10 carbon atoms; the term "alkanoyl" refers to groups having 2 to 11 carbon atoms; and the term "cycloalkyl" refers to groups having 3, 4, 5, 6 or 7 carbon atoms.
Claim 2
Dependent Claim 306 words
A compound having the formula ##STR17## or a pharmaceutically acceptable salt thereof wherein R 1 is hydrogen, alkyl, alkanoyl, alkenyl, arylcarbonyl, heteroarylcarbonyl or ##STR18## R 2 and R 3 are each independently hydrogen, alkyl, cycloalkyl or arylalkyl or R 2 and R 3 together with the nitrogen atom to which they are attached are pyrrolidinyl, piperidinyl, or morpholinyl; R 4 and R 5 are each independently hydrogen, halogen, alkyl, alkoxy, aryloxy, arylalkoxy, diarylalkoxy, arylalkyl, cyano, hydroxy, alkanoyloxy, ##STR19## fluoro substituted alkoxy, fluoro substituted alkyl, (cycloalkyl)alkoxy, --NO 2 , --NX 3 X 4 , --S(O) m alkyl, --S(O) m aryl, ##STR20## n is 2 or 3; m is 0, 1 or 2; X 1 and X 2 are each independently hydrogen, alkyl, aryl or heteroaryl, or X 1 and X 2 together with the nitrogen atom to which they are attached are pyrrolidinyl, piperidinyl or morpholinyl; X 3 and X 4 are each independently hydrogen, alkyl, alkanoyl, arylcarbonyl, heteroacrylcarbonyl, or ##STR21## X 5 is hydroxy, alkoxy, aryloxy, amino, alkylamino or dialkylamino; and X 6 is alkyl, alkoxy or aryloxy; with the proviso that if R4 is a 7-alkyl group, it must have a tertiary carbon atom bonded to the ring; wherein the term "aryl" refers to phenyl and phenyl substituted with 1, 2 or 3 amino, alkylamino, dialkylamino, nitro, halogen, hydroxyl, trifluoromethyl, alkyl or 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkanoyloxy, carbamoyl, or carboxyl groups; the term "heteroaryl" refers to pyridinyl, pyrrolyl, imidazolyl, furyl, thienyl, or thiazolyl; the terms "alkyl" and "alkoxy" refers to groups having 1 to 10 carbon atoms; the term "alkenyl" refers to groups having 2 to 10 carbon atoms; the term "alkanoyl" refers to groups having 2 to 11 carbon atoms; and the term "cycloalkyl" refers to groups having 3, 4, 5, 6 or 7 carbon atoms.
Claim 3
Dependent Claim 68 words
A compound in accordance with claim 1 wherein R 4 and R 5 are each independently hydrogen, halogen, alkyl, alkoxy, aryloxy, arylalkoxy, arylalkyl, hydroxy, alkanoyloxy, ##STR22## difluoromethoxy, trifluoromethyl, --NX 3 X 4 , 13 S(O) m aklyl or --S(O) m aryl; X 1 and X 2 are each independently hydrogen, alkyl or heteroaryl; and X 3 and X 4 are each independently alkyl, alkanoyl, arylcarbonyl, heteroarylcarbonyl, or ##STR23##
Claim 4
Dependent Claim 19 words
A compound in accordance with claim 1 wherein R 2 and R 3 are each independently alkyl or cycloalkyl.
Claim 5
Dependent Claim 12 words
A compound in accordance with claim 1 wherein R 1 is hydrogen.
Claim 6
Dependent Claim 12 words
A compound in accordance with claim 1 wherein R 1 is alkyl.
Claim 7
Dependent Claim 17 words
A compound in accordance with claim 1 wherein R 1 is alkanoyl, alkenyl, arylcarbonyl, heteroarylcarbonyl or ##STR24##
Claim 8
Dependent Claim 12 words
A compound in accordance with claim 6 wherein R 1 is alkanoyl.
Claim 9
Dependent Claim 12 words
A compound in accordance with claim 7 wherein R 1 is acetyl.
Claim 10
Dependent Claim 16 words
A compound in accordance with claim 1 wherein R 2 and R 3 are each alkyl.
Claim 11
Dependent Claim 16 words
A compound in accordance with claim 9 wherein R 2 and R 3 are each methyl.
Claim 12
Dependent Claim 16 words
A compound in accordance with claim 1 wherein R 2 and R 3 are each cycloalkyl.
Claim 13
Dependent Claim 28 words
A compound in accordance with claim 1 wherein R 2 and R 3 together with the nitrogen atom to which they are attached are pyrrolidinyl, piperidinyl or morpholinyl.
Claim 14
Dependent Claim 12 words
A compound in accordance with claim 1 wherein R 4 is hydrogen.
Claim 15
Dependent Claim 12 words
A compound in accordance with claim 1 wherein R 4 is halogen.
Claim 16
Dependent Claim 22 words
A compound in accordance with claim 1 wherein R 4 is chlorine and is located in the 7-position of the benzazepine nucleus.
Claim 17
Dependent Claim 22 words
A compound in accordance with claim 1 wherein R 4 is trifluoromethyl and is located in the 6-position of the benzazepine nucleus.
Claim 18
Dependent Claim 22 words
A compound in accordance with claim 1 wherein R 4 is trifluoromethyl and is located in the 7-position of the benzazepine nucleus.
Claim 19
Dependent Claim 12 words
A compound in accordance with claim 1 wherein R 5 is alkoxy.
Claim 20
Dependent Claim 27 words
A compound in accordance with claim 1 wherein R 5 is methoxy and is located in the 4-position of the phenyl ring to which it is attached.
Claim 21
Dependent Claim 11 words
A compound in accordance with claim 1 wherein n is 2.
Claim 22
Dependent Claim 11 words
A compound in accordance with claim 1 wherein n is 3.
Claim 23
Dependent Claim 9 words
The d-cis enantiomer of a compound of claim 1.
Claim 24
Dependent Claim 48 words
A compound in accordance with claim 1 wherein R 1 is alkanoyl, R 2 and R 3 are each alkyl, R 4 is 6- or 7-trifluoromethyl, R 5 is alkoxy and is located in the 4-position of the ring to which it is attached, and n is 2.
Claim 25
Dependent Claim 15 words
The compound in accordance with claim 1, (cis)-3-(acetyloxy)-7-chloro-1-[2-(dimethylamino)ethyl]-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-2H 1-benzazepin-2-one or a pharmaceutically acceptable salt thereof.
Claim 26
Dependent Claim 14 words
The compound in accordance with claim 1, (cis)-3-(acetyloxy)-1-[2-(dimethylamino)ethyl]-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one or a pharmaceutically acceptable salt thereof.
Claim 27
Dependent Claim 14 words
The compound in accordance with claim 1, (trans)-3-(acetyloxy)-1-2-(dimethylamino)ethyl]-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one, or a pharmaceutically acceptable salt thereof.
Claim 28
Dependent Claim 14 words
The compound in accordance with claim 1, (cis)-3-(acetyloxy)-1-[2-(dimethylamino)ethyl]-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-7-(trifluoromethyl)-2H-1-benzazepin-2-one, or a pharmaceutically acceptable salt thereof.
Claim 29
Dependent Claim 15 words
The compound in accordance with claim 1, (cis)-3-(acetyloxy)-7-(methoxy)-1-2-(dimethylamino)ethyl]-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-2H 2-one, or a pharmaceutically acceptable salt thereof.
Claim 30
Dependent Claim 14 words
The compound in accordance with claim 1, (d-cis)-3-(acetyloxy)-1-[2-(dimethylamino)ethyl]-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-6-(trifluoro-methyl)-2H-1-benzazepin-2-one, or a pharmaceutically acceptable salt thereof.
Claim 31
Dependent Claim 14 words
The compound in accordance with claim 1, (d-cis)-3-(acetyloxy)-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-1-[2-(methylamino)ethyl]-6-(trifluoromethyl)-2H-1-benzazepin-2-one, or a pharmaceutically acceptable salt thereof.

References Cited (Backward Citations)

US3312691A Cited
US3330823A Cited
US3748321A Cited
US3562257A Cited
EP0205334A2 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1991-05-31 1991-11-30 1992-05-31 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1995-05-31 1995-11-30 1996-05-31 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1999-05-31 1999-11-30 2000-05-31 $7700.00 Window Closed / Lapsed

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