CA1271966C - Aryl and aralkyl sulfonyl l-prolines - Google Patents
Aryl and aralkyl sulfonyl l-prolinesInfo
- Publication number
- CA1271966C CA1271966C CA615516A CA615516A CA1271966C CA 1271966 C CA1271966 C CA 1271966C CA 615516 A CA615516 A CA 615516A CA 615516 A CA615516 A CA 615516A CA 1271966 C CA1271966 C CA 1271966C
- Authority
- CA
- Canada
- Prior art keywords
- prolines
- aryl
- formula
- aralkyl sulfonyl
- useful
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000005140 aralkylsulfonyl group Chemical group 0.000 title abstract 3
- 125000003118 aryl group Chemical group 0.000 title abstract 3
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 abstract 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 abstract 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 abstract 1
- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 abstract 1
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000002220 antihypertensive agent Substances 0.000 abstract 1
- 229940030600 antihypertensive agent Drugs 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000005764 inhibitory process Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 235000013930 proline Nutrition 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
Abstract
ABSTRACT This invention provides new aryl and aralkyl sulfonyl L-prolines of the formula wherein: R is hydrogen or lower alkyl; m is zero or an integer from 1 to 4; R1 , a 1- or 2-naphthyl of the formula , or which are useful as intermediates in the preparation of new acyl mercaptoalkanoyl and mercaptoalkanoyl derivatives of aryl and aralkyl sulfonyl prolines of the formula IMG> which possess angiotensin converting enzyme inhibition activity and thus are useful as anti-hypertensive agents.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000615516A CA1271966A (en) | 1983-04-25 | 1984-04-17 | Aryl and aralkyl sulfonyl l-prolines |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48847783A | 1983-04-25 | 1983-04-25 | |
| CA000452213A CA1266661A (en) | 1983-04-25 | 1984-04-17 | Acylmercaptoalkanoyl and mercaptoalkanoyl derivatives of aryl and aralkyl sulfinyl or sulfonyl l-prolines |
| CA000615516A CA1271966A (en) | 1983-04-25 | 1984-04-17 | Aryl and aralkyl sulfonyl l-prolines |
| US488,477 | 1995-06-08 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000452213A Division CA1266661A (en) | 1983-04-25 | 1984-04-17 | Acylmercaptoalkanoyl and mercaptoalkanoyl derivatives of aryl and aralkyl sulfinyl or sulfonyl l-prolines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA1271966C true CA1271966C (en) | 1990-07-24 |
| CA1271966A CA1271966A (en) | 1990-07-24 |
Family
ID=34117156
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000452213A Expired - Lifetime CA1266661A (en) | 1983-04-25 | 1984-04-17 | Acylmercaptoalkanoyl and mercaptoalkanoyl derivatives of aryl and aralkyl sulfinyl or sulfonyl l-prolines |
| CA000615516A Expired - Lifetime CA1271966A (en) | 1983-04-25 | 1984-04-17 | Aryl and aralkyl sulfonyl l-prolines |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000452213A Expired - Lifetime CA1266661A (en) | 1983-04-25 | 1984-04-17 | Acylmercaptoalkanoyl and mercaptoalkanoyl derivatives of aryl and aralkyl sulfinyl or sulfonyl l-prolines |
Country Status (1)
| Country | Link |
|---|---|
| CA (2) | CA1266661A (en) |
-
1984
- 1984-04-17 CA CA000452213A patent/CA1266661A/en not_active Expired - Lifetime
- 1984-04-17 CA CA000615516A patent/CA1271966A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA1266661C (en) | 1990-03-13 |
| CA1271966A (en) | 1990-07-24 |
| CA1266661A (en) | 1990-03-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed | ||
| MKLA | Lapsed |
Effective date: 20020724 |