CH611604A5 - Process for the preparation of an 8-azaprostaglandin - Google Patents
Process for the preparation of an 8-azaprostaglandinInfo
- Publication number
- CH611604A5 CH611604A5 CH350176A CH350176A CH611604A5 CH 611604 A5 CH611604 A5 CH 611604A5 CH 350176 A CH350176 A CH 350176A CH 350176 A CH350176 A CH 350176A CH 611604 A5 CH611604 A5 CH 611604A5
- Authority
- CH
- Switzerland
- Prior art keywords
- pge1
- isomers
- derivative
- prepared
- image
- Prior art date
Links
- GMVPRGQOIOIIMI-UHFFFAOYSA-N (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CCCCCCC(O)=O GMVPRGQOIOIIMI-UHFFFAOYSA-N 0.000 abstract 3
- 229960000711 alprostadil Drugs 0.000 abstract 3
- GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- -1 alkali metal salt Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 208000006673 asthma Diseases 0.000 abstract 1
- 230000003182 bronchodilatating effect Effects 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/16—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C07C51/38—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by decarboxylation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pulmonology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
An 8-azaprostaglandin of formula: <IMAGE> is prepared by saponifying, in an alcohol medium and using an alkali metal hydroxide, an ester of general formula: <IMAGE> in which R represents a linear or branched alkyl containing 1 to 7 carbon atoms, and then the alkali metal salt thus formed is hydrolysed using a strong acid. The derivative thus prepared in a completely synthetic way can exist in the form of optical isomers, positional isomers or a mixture of these isomers. However, its chemical structure is simpler than that of PGE1 because the asymmetry of the 8 and 11 carbons is suppressed. The derivative of the invention has the properties of PGE1, in particular a more specific bronchodilatory activity than that of PGE1. It can be used especially in the treatment of asthma.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB12034/75A GB1529852A (en) | 1975-03-21 | 1975-03-21 | 8-azaprostaglandins and process for the preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH611604A5 true CH611604A5 (en) | 1979-06-15 |
Family
ID=9997230
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH844678A CH611881A5 (en) | 1975-03-21 | 1976-03-19 | Process for the preparation of 8-azaprostaglandins |
| CH350176A CH611604A5 (en) | 1975-03-21 | 1976-03-19 | Process for the preparation of an 8-azaprostaglandin |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH844678A CH611881A5 (en) | 1975-03-21 | 1976-03-19 | Process for the preparation of 8-azaprostaglandins |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS607602B2 (en) |
| AR (1) | AR213172A1 (en) |
| AT (1) | AT348163B (en) |
| AU (1) | AU501105B2 (en) |
| BE (1) | BE839761A (en) |
| CA (1) | CA1076587A (en) |
| CH (2) | CH611881A5 (en) |
| DE (1) | DE2612114A1 (en) |
| DK (1) | DK140937B (en) |
| ES (2) | ES446239A1 (en) |
| FI (1) | FI61692C (en) |
| FR (1) | FR2304340A1 (en) |
| GB (1) | GB1529852A (en) |
| HU (1) | HU173348B (en) |
| IE (1) | IE42966B1 (en) |
| IT (1) | IT1061011B (en) |
| MX (1) | MX3301E (en) |
| NL (1) | NL7602891A (en) |
| NO (1) | NO144147C (en) |
| NZ (1) | NZ180251A (en) |
| OA (1) | OA05279A (en) |
| PT (1) | PT64919B (en) |
| SE (1) | SE418290B (en) |
| SU (1) | SU614746A3 (en) |
| YU (1) | YU73876A (en) |
| ZA (1) | ZA761448B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4097489A (en) * | 1977-06-17 | 1978-06-27 | The Upjohn Company | 9-Deoxy-9α,6-nitrilo or 6,9α-imino-PGF compounds |
| US5540618A (en) * | 1994-10-28 | 1996-07-30 | National University Of Singapore | Passive attenuator for shelter protection against explosions |
| WO2003074483A1 (en) | 2002-03-05 | 2003-09-12 | Ono Pharmaceutical Co., Ltd. | 8-azaprostaglandin derivative compounds and drugs containing the compounds as the active ingredient |
-
1975
- 1975-03-21 GB GB12034/75A patent/GB1529852A/en not_active Expired
-
1976
- 1976-03-02 DK DK88276AA patent/DK140937B/en not_active IP Right Cessation
- 1976-03-09 ZA ZA761448A patent/ZA761448B/en unknown
- 1976-03-09 NZ NZ180251A patent/NZ180251A/en unknown
- 1976-03-11 AU AU11899/76A patent/AU501105B2/en not_active Expired
- 1976-03-15 IE IE545/76A patent/IE42966B1/en unknown
- 1976-03-17 AT AT195676A patent/AT348163B/en not_active IP Right Cessation
- 1976-03-18 IT IT21346/76A patent/IT1061011B/en active
- 1976-03-18 SE SE7603400A patent/SE418290B/en unknown
- 1976-03-18 FR FR7607794A patent/FR2304340A1/en active Granted
- 1976-03-18 PT PT64919A patent/PT64919B/en unknown
- 1976-03-19 CH CH844678A patent/CH611881A5/en not_active IP Right Cessation
- 1976-03-19 YU YU00738/76A patent/YU73876A/en unknown
- 1976-03-19 AR AR262630A patent/AR213172A1/en active
- 1976-03-19 CH CH350176A patent/CH611604A5/en not_active IP Right Cessation
- 1976-03-19 BE BE165326A patent/BE839761A/en not_active IP Right Cessation
- 1976-03-19 CA CA248,275A patent/CA1076587A/en not_active Expired
- 1976-03-19 HU HU76LA885A patent/HU173348B/en unknown
- 1976-03-19 FI FI760744A patent/FI61692C/en not_active IP Right Cessation
- 1976-03-19 SU SU762334454A patent/SU614746A3/en active
- 1976-03-19 NL NL7602891A patent/NL7602891A/en not_active Application Discontinuation
- 1976-03-19 NO NO760994A patent/NO144147C/en unknown
- 1976-03-19 MX MX000100U patent/MX3301E/en unknown
- 1976-03-20 ES ES446239A patent/ES446239A1/en not_active Expired
- 1976-03-20 OA OA55774A patent/OA05279A/en unknown
- 1976-03-22 DE DE19762612114 patent/DE2612114A1/en not_active Withdrawn
- 1976-03-22 JP JP51031889A patent/JPS607602B2/en not_active Expired
-
1977
- 1977-05-03 ES ES458389A patent/ES458389A1/en not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PFA | Name/firm changed |
Owner name: SANOFI |
|
| PUE | Assignment |
Owner name: OMNIUM FINANCIER AQUITAINE POUR L HYGIENE ET LA SA |
|
| PL | Patent ceased |