GB1529852A - 8-azaprostaglandins and process for the preparation thereof - Google Patents
8-azaprostaglandins and process for the preparation thereofInfo
- Publication number
- GB1529852A GB1529852A GB12034/75A GB1203475A GB1529852A GB 1529852 A GB1529852 A GB 1529852A GB 12034/75 A GB12034/75 A GB 12034/75A GB 1203475 A GB1203475 A GB 1203475A GB 1529852 A GB1529852 A GB 1529852A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- methyl
- oxo
- azaprostaglandins
- pyrrolidineheptanoate
- 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 4
- SNVVZCPNLVAKLC-UHFFFAOYSA-N 1-chloroheptan-2-one Chemical compound CCCCCC(=O)CCl SNVVZCPNLVAKLC-UHFFFAOYSA-N 0.000 abstract 2
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract 2
- DERLEQYHZCMIPL-UHFFFAOYSA-N 1-(triphenyl-$l^{5}-phosphanylidene)heptan-2-one Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)CCCCC)C1=CC=CC=C1 DERLEQYHZCMIPL-UHFFFAOYSA-N 0.000 abstract 1
- VKUXHMUEOAJNNB-UHFFFAOYSA-M 2-oxoheptyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC(=O)CCCCC)C1=CC=CC=C1 VKUXHMUEOAJNNB-UHFFFAOYSA-M 0.000 abstract 1
- JLPQXFFMVVPIRW-UHFFFAOYSA-N 7-bromoheptanoic acid Chemical compound OC(=O)CCCCCCBr JLPQXFFMVVPIRW-UHFFFAOYSA-N 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- WYTAKZKWHVWTEA-UHFFFAOYSA-N diethyl 2-(5-acetyloxypentyl)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)CCCCCOC(C)=O WYTAKZKWHVWTEA-UHFFFAOYSA-N 0.000 abstract 1
- YGRJFGCEOYRREO-UHFFFAOYSA-N ethyl 3-oxooctanoate Chemical compound CCCCCC(=O)CC(=O)OCC YGRJFGCEOYRREO-UHFFFAOYSA-N 0.000 abstract 1
- QYJOOVQLTTVTJY-UHFFFAOYSA-N ethyl 5-oxopyrrolidine-2-carboxylate Chemical compound CCOC(=O)C1CCC(=O)N1 QYJOOVQLTTVTJY-UHFFFAOYSA-N 0.000 abstract 1
- YDARFNBVDDWMBQ-UHFFFAOYSA-N ethyl 7-[2-(hydroxymethyl)-5-oxopyrrolidin-1-yl]heptanoate Chemical compound CCOC(=O)CCCCCCN1C(CO)CCC1=O YDARFNBVDDWMBQ-UHFFFAOYSA-N 0.000 abstract 1
- AHMWONZNKYSQBH-FYWRMAATSA-N ethyl 7-[2-oxo-5-[(E)-3-oxooct-1-enyl]pyrrolidin-1-yl]heptanoate Chemical compound O=C(/C=C/C1N(C(CC1)=O)CCCCCCC(=O)OCC)CCCCC AHMWONZNKYSQBH-FYWRMAATSA-N 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- COYUAWIJCNCEKE-UHFFFAOYSA-N methyl 7-(2-formyl-5-oxopyrrolidin-1-yl)heptanoate Chemical compound COC(=O)CCCCCCN1C(C=O)CCC1=O COYUAWIJCNCEKE-UHFFFAOYSA-N 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- VCRAOJUOQXBKSE-UHFFFAOYSA-M silver 8-methoxy-8-oxooctanoate Chemical compound C(CCCCCCC(=O)[O-])(=O)OC.[Ag+] VCRAOJUOQXBKSE-UHFFFAOYSA-M 0.000 abstract 1
- 238000010561 standard procedure Methods 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)
Priority Applications (31)
| 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 |
| DK88276AA DK140937B (da) | 1975-03-21 | 1976-03-02 | Analogifremgangsmåde til fremstilling af et 2-pyrrolidinonderivat. |
| ZA761448A ZA761448B (en) | 1975-03-21 | 1976-03-09 | Prostaglandin derivative and process for the preparation thereof |
| NZ180251A NZ180251A (en) | 1975-03-21 | 1976-03-09 | Prostaglandin derivatives and pharmaceutical and veterinary compositions |
| AU11899/76A AU501105B2 (en) | 1975-03-21 | 1976-03-11 | Prostaglandin derivatives |
| IE545/76A IE42966B1 (en) | 1975-03-21 | 1976-03-15 | 8-azaprostaglandins and process for the preparation thereof |
| AT195676A AT348163B (de) | 1975-03-21 | 1976-03-17 | Verfahren zur herstellung eines neuen prostaglandinderivates |
| IT21346/76A IT1061011B (it) | 1975-03-21 | 1976-03-18 | Derivati della prostaglandina e procedimento per la loro preparazione |
| SE7603400A SE418290B (sv) | 1975-03-21 | 1976-03-18 | Sett att framstella prostaglandinderivat |
| FR7607794A FR2304340A1 (fr) | 1975-03-21 | 1976-03-18 | Nouveaux derives de prostaglandine, leur procede de preparation ainsi que les compositions therapeutiques les contenant |
| PT64919A PT64919B (en) | 1975-03-21 | 1976-03-18 | Process for preparing prostaglandin derivatives with pharmaceutical effect |
| NL7602891A NL7602891A (nl) | 1975-03-21 | 1976-03-19 | Werkwijze voor de bereiding van nieuwe prostaglan- dinederivaten. |
| HU76LA885A HU173348B (hu) | 1975-03-21 | 1976-03-19 | Sposob poluchenija novykh proizvodnykh 8-aza-prostaglandinov |
| YU00738/76A YU73876A (en) | 1975-03-21 | 1976-03-19 | Process for obtaining prostaglandin derivatives |
| CH350176A CH611604A5 (en) | 1975-03-21 | 1976-03-19 | Process for the preparation of an 8-azaprostaglandin |
| AR262630A AR213172A1 (es) | 1975-03-21 | 1976-03-19 | Nuevos compuestos derivados de la dl-omega-carboalcoxi(c1-c7)-hexil-5-(3'-hidroxi-u-oxo-1'octen-(e)-il)-2-pirrolidinona,desprovistos de actividad terapeutica y particularmente utiles como intermediarios en la sintesis de derivados de prostaglandina,tales como la dl-8-aza-11-deoxi-pge,procedimiento para elaborar dicha prostagiandina y procedimiento para preparar los referidos intermediarios |
| FI760744A FI61692C (fi) | 1975-03-21 | 1976-03-19 | Foerfarande foer framstaellning av farmakologiskt aktiva prostaglandinderivat |
| BE165326A BE839761A (fr) | 1975-03-21 | 1976-03-19 | Nouveaux derives de prostaglandine, leur procede de preparation ainsi que les compositions therapeutiques les contenant |
| SU762334454A SU614746A3 (ru) | 1975-03-21 | 1976-03-19 | Способ получени аналога простагландина |
| MX000100U MX3301E (es) | 1975-03-21 | 1976-03-19 | Procedimiento para preparar un derivado de prostaglandina |
| CA248,275A CA1076587A (en) | 1975-03-21 | 1976-03-19 | Prostaglandin derivatives and process for preparing the same |
| NO760994A NO144147C (no) | 1975-03-21 | 1976-03-19 | Analogifremgangsmaate for fremstilling av farmakologisk aktive prostaglandinderivater |
| CH844678A CH611881A5 (en) | 1975-03-21 | 1976-03-19 | Process for the preparation of 8-azaprostaglandins |
| ES446239A ES446239A1 (es) | 1975-03-21 | 1976-03-20 | Procedimiento para preparar un derivado de prostaglandina. |
| OA55774A OA05279A (fr) | 1975-03-21 | 1976-03-20 | Procédé de préparation de prostaglandine. |
| JP51031889A JPS607602B2 (ja) | 1975-03-21 | 1976-03-22 | プロスタグランジン誘導体を有効成分として含有する医薬又は獣医薬組成物 |
| DE19762612114 DE2612114A1 (de) | 1975-03-21 | 1976-03-22 | Prostaglandin-derivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische oder veterinaermedizinische zusammensetzungen |
| ES458389A ES458389A1 (es) | 1975-03-21 | 1977-05-03 | Procedimiento para preparar derivados de prostaglandina. |
| AT42678A AT354659B (de) | 1975-03-21 | 1978-01-20 | Verfahren zur herstellung von neuen prostaglandinderivaten |
| DK80578A DK140532B (da) | 1975-03-21 | 1978-02-22 | Analogifremgangsmåde til fremstilling af 2-pyrrolidinonderivater. |
| YU142182A YU142182A (en) | 1975-03-21 | 1982-06-30 | Process for obtaining prostaglandin derivatives |
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 |
|---|---|
| GB1529852A true GB1529852A (en) | 1978-10-25 |
Family
ID=9997230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12034/75A Expired GB1529852A (en) | 1975-03-21 | 1975-03-21 | 8-azaprostaglandins and process for the preparation thereof |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS607602B2 (ja) |
| AR (1) | AR213172A1 (ja) |
| AT (1) | AT348163B (ja) |
| AU (1) | AU501105B2 (ja) |
| BE (1) | BE839761A (ja) |
| CA (1) | CA1076587A (ja) |
| CH (2) | CH611881A5 (ja) |
| DE (1) | DE2612114A1 (ja) |
| DK (1) | DK140937B (ja) |
| ES (2) | ES446239A1 (ja) |
| FI (1) | FI61692C (ja) |
| FR (1) | FR2304340A1 (ja) |
| GB (1) | GB1529852A (ja) |
| HU (1) | HU173348B (ja) |
| IE (1) | IE42966B1 (ja) |
| IT (1) | IT1061011B (ja) |
| MX (1) | MX3301E (ja) |
| NL (1) | NL7602891A (ja) |
| NO (1) | NO144147C (ja) |
| NZ (1) | NZ180251A (ja) |
| OA (1) | OA05279A (ja) |
| PT (1) | PT64919B (ja) |
| SE (1) | SE418290B (ja) |
| SU (1) | SU614746A3 (ja) |
| YU (1) | YU73876A (ja) |
| ZA (1) | ZA761448B (ja) |
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 (fr) | 2002-03-05 | 2003-09-12 | Ono Pharmaceutical Co., Ltd. | Composes derives de 8 azaprostaglandine et medicaments contenant ceux-ci comme principe actif |
-
1975
- 1975-03-21 GB GB12034/75A patent/GB1529852A/en not_active Expired
-
1976
- 1976-03-02 DK DK88276AA patent/DK140937B/da not_active IP Right Cessation
- 1976-03-09 ZA ZA761448A patent/ZA761448B/xx unknown
- 1976-03-09 NZ NZ180251A patent/NZ180251A/xx 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/de not_active IP Right Cessation
- 1976-03-18 IT IT21346/76A patent/IT1061011B/it active
- 1976-03-18 SE SE7603400A patent/SE418290B/xx unknown
- 1976-03-18 FR FR7607794A patent/FR2304340A1/fr active Granted
- 1976-03-18 PT PT64919A patent/PT64919B/pt unknown
- 1976-03-19 CH CH844678A patent/CH611881A5/xx not_active IP Right Cessation
- 1976-03-19 YU YU00738/76A patent/YU73876A/xx unknown
- 1976-03-19 AR AR262630A patent/AR213172A1/es active
- 1976-03-19 CH CH350176A patent/CH611604A5/xx not_active IP Right Cessation
- 1976-03-19 BE BE165326A patent/BE839761A/xx not_active IP Right Cessation
- 1976-03-19 CA CA248,275A patent/CA1076587A/en not_active Expired
- 1976-03-19 HU HU76LA885A patent/HU173348B/hu unknown
- 1976-03-19 FI FI760744A patent/FI61692C/fi not_active IP Right Cessation
- 1976-03-19 SU SU762334454A patent/SU614746A3/ru active
- 1976-03-19 NL NL7602891A patent/NL7602891A/xx not_active Application Discontinuation
- 1976-03-19 NO NO760994A patent/NO144147C/no unknown
- 1976-03-19 MX MX000100U patent/MX3301E/es unknown
- 1976-03-20 ES ES446239A patent/ES446239A1/es not_active Expired
- 1976-03-20 OA OA55774A patent/OA05279A/xx unknown
- 1976-03-22 DE DE19762612114 patent/DE2612114A1/de not_active Withdrawn
- 1976-03-22 JP JP51031889A patent/JPS607602B2/ja not_active Expired
-
1977
- 1977-05-03 ES ES458389A patent/ES458389A1/es not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |