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Patent · US4400511A · A · US

2-Substituted octahydropyrrolo(1,2-A)-pyrazine-3-carboxylic acids

(11) Publication number
US4400511A
(21) Application number
US-37585882-A
(22) Filing date
1982-05-07
(30) Priority date
1982-05-07
(43) Publication date
1983-08-23
(45) Date of grant
1983-08-23
(52) CPC
  • C07D Heterocyclic compounds: 487/04
(73) Assignee
AMERICAN HOME PROD
(54) Title
2-Substituted octahydropyrrolo(1,2-A)-pyrazine-3-carboxylic acids
(57) Abstract

The compounds ##STR1## where R is hydrogen, alkyl, phenylalkyl or dialkylamino alkyl; R 1 is hydrogen, alkyl or phenyl; X is --S-- or --NH-- A is hydrogen, acyl, aroyl, alkyl or substituted alkyl in which the substituent is alkoxycarbonyl or phenylalkyl; n is 0, 1 or 2; or a pharmaceutically acceptable salt thereof are antihypertensive agents of the ACE inhibitor type.

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Claims (6)

  1. A compound of the formula ##STR5## in which R is hydrogen, alkyl of 1 to 6 carbon atoms, phenylalkyl of 7 to 12 carbon atoms, or dialkylaminoalkyl where each alkyl group has 1 to 6 carbon atoms; R 1 is hydrogen, alkyl of 1 to 6 carbon atoms or phenyl; X is --S-- or --NH--; A is hydrogen, alkyl of 1 to 6 carbon atoms, alkoxycarbonylalkyl in which each alkyl moiety has 1 to 6 carbon atoms, phenylalkyl of 7 to 12 carbon atoms, phenyl(alkoxycarbonyl)alkyl in which each alkyl group has 1 to 6 carbon atoms, alkanoyl of 2 to 7 carbon atoms, benzoyl or naphthoyl; and n is one of the integers 0, 1 or 2 or a pharmaceutically acceptable salt thereof.
  2. The compound of claim 1 which is 4-(3-benzoylthio-2-methylpropionyl)-1,4-diazabicyclo[4.3.0]nonane-3-carboxylic acid or a pharmaceutically acceptable salt thereof.
  3. The compound of claim 1 which is 4-(3-mercapto-2-methylpropionyl)-1,4-diazabicyclo[4.3.0]nonane-3-carboxylic acid or a pharmaceutically acceptable salt thereof.
  4. The compound of claim 1 which is 4-(3-benzoylthiopropionyl)-1,4-diazabicyclo[4.3.0]nonane-3-carboxylic acid or a pharmaceutically acceptable salt thereof.
  5. The compound of claim 1 which is 4-(3-mercaptopropionyl)-1,4-diazabicyclo[4.3.0]nonane-3-carboxylic acid or a pharmaceutically acceptable salt thereof.
  6. The compound of claim 1 which is 4-[2-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,4-diazabicyclo[4.3.0nonane-3-carboxylic acid or a pharmaceutically acceptable salt thereof.

Citations (4)

  • JPS5088093A
  • US3531485A
  • US4291163A
  • US4294832A
Record as JSON
{
  "publication_number": "US4400511A",
  "country": "US",
  "kind": "A",
  "title": "2-Substituted octahydropyrrolo(1,2-A)-pyrazine-3-carboxylic acids",
  "abstract": "The compounds ##STR1## where R is hydrogen, alkyl, phenylalkyl or dialkylamino alkyl; R 1 is hydrogen, alkyl or phenyl; X is --S-- or --NH-- A is hydrogen, acyl, aroyl, alkyl or substituted alkyl in which the substituent is alkoxycarbonyl or phenylalkyl; n is 0, 1 or 2; or a pharmaceutically acceptable salt thereof are antihypertensive agents of the ACE inhibitor type.",
  "claims": [
    "1. A compound of the formula ##STR5## in which R is hydrogen, alkyl of 1 to 6 carbon atoms, phenylalkyl of 7 to 12 carbon atoms, or dialkylaminoalkyl where each alkyl group has 1 to 6 carbon atoms; R 1 is hydrogen, alkyl of 1 to 6 carbon atoms or phenyl; X is --S-- or --NH--; A is hydrogen, alkyl of 1 to 6 carbon atoms, alkoxycarbonylalkyl in which each alkyl moiety has 1 to 6 carbon atoms, phenylalkyl of 7 to 12 carbon atoms, phenyl(alkoxycarbonyl)alkyl in which each alkyl group has 1 to 6 carbon atoms, alkanoyl of 2 to 7 carbon atoms, benzoyl or naphthoyl; and n is one of the integers 0, 1 or 2 or a pharmaceutically acceptable salt thereof.",
    "2. The compound of claim 1 which is 4-(3-benzoylthio-2-methylpropionyl)-1,4-diazabicyclo[4.3.0]nonane-3-carboxylic acid or a pharmaceutically acceptable salt thereof.",
    "3. The compound of claim 1 which is 4-(3-mercapto-2-methylpropionyl)-1,4-diazabicyclo[4.3.0]nonane-3-carboxylic acid or a pharmaceutically acceptable salt thereof.",
    "4. The compound of claim 1 which is 4-(3-benzoylthiopropionyl)-1,4-diazabicyclo[4.3.0]nonane-3-carboxylic acid or a pharmaceutically acceptable salt thereof.",
    "5. The compound of claim 1 which is 4-(3-mercaptopropionyl)-1,4-diazabicyclo[4.3.0]nonane-3-carboxylic acid or a pharmaceutically acceptable salt thereof.",
    "6. The compound of claim 1 which is 4-[2-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,4-diazabicyclo[4.3.0nonane-3-carboxylic acid or a pharmaceutically acceptable salt thereof."
  ],
  "cpc": [
    "C07D 487/04"
  ],
  "assignees": [
    "AMERICAN HOME PROD"
  ],
  "filing_date": "1982-05-07",
  "publication_date": "1983-08-23",
  "grant_date": "1983-08-23",
  "priority_date": "1982-05-07",
  "application_number": "US-37585882-A",
  "family_id": "23482660",
  "citations": [
    "JPS5088093A",
    "US3531485A",
    "US4291163A",
    "US4294832A"
  ]
}

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