IE42966L - 8-azaprostaglandins and process for the preparation thereof. - Google Patents
8-azaprostaglandins and process for the preparation thereof.Info
- Publication number
- IE42966L IE42966L IE760545A IE54576A IE42966L IE 42966 L IE42966 L IE 42966L IE 760545 A IE760545 A IE 760545A IE 54576 A IE54576 A IE 54576A IE 42966 L IE42966 L IE 42966L
- Authority
- IE
- Ireland
- Prior art keywords
- ethyl
- methyl
- oxo
- azaprostaglandins
- pyrrolidineheptanoate
- Prior art date
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)
Abstract
1529852 8-Azaprostaglandins LABAZ 11 March 1976 [21 March 1975] 12034/75 Headings C2C and C2P The invention comprises 8-azaprostaglandins of the Formula I wherein R is H, methyl or ethyl and their preparation by standard methods. The following intermediates are also prepared: silver methyl suberate, 1-chloro-2-heptanone, ethyl DL-pyroglutamate DL-6-hydroxymethyl - 2 - pyrrolidinone, and its 2 - tetrahydropyranyl ether; methyl and ethyl 2-hydroxymethyl - 5 - oxo - 1 - pyrrolidineheptanoate and its 2 - tetrahydropyranyl ether; ethyl and methyl 2 - formyl - 5 - oxo - 1 - pyrrolidineheptanoate; methyl and ethyl 2 - (3 - oxo - -trans- 1 - octenyl) - 5 - oxo - 1 - pyrrolidineheptanoate; diethyl (5 - acetoxypentyl)malonate; 7 - bromoheptanoic acid and its methyl and ethyl esters; and ethyl 3-oxooctanoate. (2 - Oxoheptylidene)triphenylphosphorane is prepared by reacting potassium carbonate with (2 - oxoheptyl)triphenylphosphonium chloride obtained by reacting triphenyl phosphine with 1-chloro-2-heptanone. Pharmaceutical compositions contain the 8- azaprostaglandins of Formula I above in association with non-toxic carriers or excipients therefor. The compounds possess similar pharmacological properties to those of PGE.
[GB1529852A]
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 (2)
| Publication Number | Publication Date |
|---|---|
| IE42966L true IE42966L (en) | 1976-09-21 |
| IE42966B1 IE42966B1 (en) | 1980-11-19 |
Family
ID=9997230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE545/76A IE42966B1 (en) | 1975-03-21 | 1976-03-15 | 8-azaprostaglandins and process for the preparation thereof |
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) | CH611604A5 (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 |
| AU2003211574A1 (en) | 2002-03-05 | 2003-09-16 | 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 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
- 1976-03-18 IT IT21346/76A patent/IT1061011B/en active
- 1976-03-19 NO NO760994A patent/NO144147C/en unknown
- 1976-03-19 CH CH350176A patent/CH611604A5/en not_active IP Right Cessation
- 1976-03-19 MX MX000100U patent/MX3301E/en unknown
- 1976-03-19 BE BE165326A patent/BE839761A/en not_active IP Right Cessation
- 1976-03-19 CH CH844678A patent/CH611881A5/en not_active IP Right Cessation
- 1976-03-19 SU SU762334454A patent/SU614746A3/en active
- 1976-03-19 HU HU76LA885A patent/HU173348B/en unknown
- 1976-03-19 YU YU00738/76A patent/YU73876A/en unknown
- 1976-03-19 CA CA248,275A patent/CA1076587A/en not_active Expired
- 1976-03-19 AR AR262630A patent/AR213172A1/en active
- 1976-03-19 FI FI760744A patent/FI61692C/en not_active IP Right Cessation
- 1976-03-19 NL NL7602891A patent/NL7602891A/en not_active Application Discontinuation
- 1976-03-20 OA OA55774A patent/OA05279A/en unknown
- 1976-03-20 ES ES446239A patent/ES446239A1/en not_active Expired
- 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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