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GB1529852A - 8-azaprostaglandins and process for the preparation thereof - Google Patents

8-azaprostaglandins and process for the preparation thereof

Info

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
Application number
GB12034/75A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Labaz SA
Original Assignee
Labaz SA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Labaz SA filed Critical Labaz SA
Priority to GB12034/75A priority Critical patent/GB1529852A/en
Priority to DK88276AA priority patent/DK140937B/en
Priority to ZA761448A priority patent/ZA761448B/en
Priority to NZ180251A priority patent/NZ180251A/en
Priority to AU11899/76A priority patent/AU501105B2/en
Priority to IE545/76A priority patent/IE42966B1/en
Priority to AT195676A priority patent/AT348163B/en
Priority to FR7607794A priority patent/FR2304340A1/en
Priority to IT21346/76A priority patent/IT1061011B/en
Priority to SE7603400A priority patent/SE418290B/en
Priority to PT64919A priority patent/PT64919B/en
Priority to NO760994A priority patent/NO144147C/en
Priority to HU76LA885A priority patent/HU173348B/en
Priority to SU762334454A priority patent/SU614746A3/en
Priority to CH350176A priority patent/CH611604A5/en
Priority to FI760744A priority patent/FI61692C/en
Priority to CH844678A priority patent/CH611881A5/en
Priority to YU00738/76A priority patent/YU73876A/en
Priority to AR262630A priority patent/AR213172A1/en
Priority to MX000100U priority patent/MX3301E/en
Priority to NL7602891A priority patent/NL7602891A/en
Priority to BE165326A priority patent/BE839761A/en
Priority to CA248,275A priority patent/CA1076587A/en
Priority to OA55774A priority patent/OA05279A/en
Priority to ES446239A priority patent/ES446239A1/en
Priority to DE19762612114 priority patent/DE2612114A1/en
Priority to JP51031889A priority patent/JPS607602B2/en
Priority to ES458389A priority patent/ES458389A1/en
Priority to AT42678A priority patent/AT354659B/en
Priority to DK80578A priority patent/DK140532B/en
Publication of GB1529852A publication Critical patent/GB1529852A/en
Priority to YU142182A priority patent/YU142182A/en
Expired legal-status Critical Current

Links

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)
  • Oil, Petroleum & Natural Gas (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (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.
GB12034/75A 1975-03-21 1975-03-21 8-azaprostaglandins and process for the preparation thereof Expired GB1529852A (en)

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 (en) 1975-03-21 1976-03-02 Analogous process for the preparation of a 2-pyrrolidinone derivative.
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 (en) 1975-03-21 1976-03-17 METHOD FOR PRODUCING A NEW PROSTAGLAND DERIVATIVE
FR7607794A FR2304340A1 (en) 1975-03-21 1976-03-18 NEW PROSTAGLANDIN DERIVATIVES, THEIR PREPARATION PROCESS AND THE THERAPEUTIC COMPOSITIONS CONTAINING THEM
IT21346/76A IT1061011B (en) 1975-03-21 1976-03-18 PROSTAGLANDIN DERIVATIVES AND PROCEDURE FOR THEIR PREPARATION
SE7603400A SE418290B (en) 1975-03-21 1976-03-18 SET TO MAKE PROSTAGLAND INGREDIENTS
PT64919A PT64919B (en) 1975-03-21 1976-03-18 Process for preparing prostaglandin derivatives with pharmaceutical effect
FI760744A FI61692C (en) 1975-03-21 1976-03-19 PROCEDURE FOR THE PRODUCTION OF PHARMACOLOGICAL ACTIVE PROSTAGINES
CA248,275A CA1076587A (en) 1975-03-21 1976-03-19 Prostaglandin derivatives and process for preparing the same
SU762334454A SU614746A3 (en) 1975-03-21 1976-03-19 Method of obtaining prostaglandine analogue
CH350176A CH611604A5 (en) 1975-03-21 1976-03-19 Process for the preparation of an 8-azaprostaglandin
NO760994A NO144147C (en) 1975-03-21 1976-03-19 ANALOGY PROCEDURE FOR THE PREPARATION OF PHARMACOLOGICALLY ACTIVE PROSTAGLAND INGREDIATES
CH844678A CH611881A5 (en) 1975-03-21 1976-03-19 Process for the preparation of 8-azaprostaglandins
YU00738/76A YU73876A (en) 1975-03-21 1976-03-19 Process for obtaining prostaglandin derivatives
AR262630A AR213172A1 (en) 1975-03-21 1976-03-19 NEW COMPOUNDS DERIVED FROM DL-OMEGA-CARBOALCOXI (C1-C7) -HEXIL-5- (3'-HYDROXY-U-OXO-1'OCTEN- (E) -IL) -2-PYRROLIDINONE, THERAPEUTIC ACTIVITY POORERS AND PARTICULARLY USEFUL AS INTERMEDIARIES IN THE SYNTHESIS OF PROSTAGLANDIN DERIVATIVES, SUCH AS DL-8-AZA-11-DEOXI-PGE, PROCEDURE TO PREPARE SAID PROSTAGIANDINE AND PROCEDURE TO PREPARE THE INTERMEDIARY REFERRALS
MX000100U MX3301E (en) 1975-03-21 1976-03-19 PROCEDURE FOR PREPARING A DERIVATIVE OF PROSTAGLANDINA
NL7602891A NL7602891A (en) 1975-03-21 1976-03-19 PROCESS FOR THE PREPARATION OF NEW PROSTAGLAN DIN DERIVATIVES.
BE165326A BE839761A (en) 1975-03-21 1976-03-19 NEW PROSTAGLANDIN DERIVATIVES, THEIR PREPARATION PROCESS AND THE THERAPEUTIC COMPOSITIONS CONTAINING THEM
HU76LA885A HU173348B (en) 1975-03-21 1976-03-19 SPOSOB POLUCHENIA NOVYKH PROIZVODNYKH 8-AZA-PROSTAGLANDINOV
OA55774A OA05279A (en) 1975-03-21 1976-03-20 Process for the preparation of prostaglandin.
ES446239A ES446239A1 (en) 1975-03-21 1976-03-20 8-azaprostaglandins and process for the preparation thereof
DE19762612114 DE2612114A1 (en) 1975-03-21 1976-03-22 PROSTAGLANDIN DERIVATIVES, THE PROCESS FOR THEIR MANUFACTURING AND THE PHARMACEUTICAL OR VETERINARY MEDICAL COMPOSITIONS THEREOF
JP51031889A JPS607602B2 (en) 1975-03-21 1976-03-22 Pharmaceutical or veterinary composition containing a prostaglandin derivative as an active ingredient
ES458389A ES458389A1 (en) 1975-03-21 1977-05-03 PROCEDURE FOR PREPARING DERIVATIVES OF PROSTAGLANDINA.
AT42678A AT354659B (en) 1975-03-21 1978-01-20 PROCESS FOR THE PRODUCTION OF NEW PROSTAGLANDIN DERIVATIVES
DK80578A DK140532B (en) 1975-03-21 1978-02-22 Analogous process for the preparation of 2-pyrrolidinone derivatives.
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 (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)

* Cited by examiner, † Cited by third party
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
MXPA04008596A (en) 2002-03-05 2004-12-06 Ono Pharmaceutical Co 8-azaprostaglandin derivative compounds and drugs containing the compounds as the active ingredient.

Also Published As

Publication number Publication date
OA05279A (en) 1981-02-28
SE418290B (en) 1981-05-18
DK140937C (en) 1980-05-19
NO144147C (en) 1981-07-15
DK140937B (en) 1979-12-10
JPS607602B2 (en) 1985-02-26
CA1076587A (en) 1980-04-29
SE7603400L (en) 1976-09-22
BE839761A (en) 1976-09-20
PT64919A (en) 1976-04-01
DE2612114A1 (en) 1976-10-07
CH611604A5 (en) 1979-06-15
NO144147B (en) 1981-03-23
PT64919B (en) 1977-08-24
JPS51138671A (en) 1976-11-30
ES458389A1 (en) 1978-02-16
HU173348B (en) 1979-04-28
YU73876A (en) 1982-10-31
IE42966L (en) 1976-09-21
FI61692C (en) 1982-09-10
ATA195676A (en) 1978-06-15
FR2304340B1 (en) 1979-06-29
ES446239A1 (en) 1977-07-01
CH611881A5 (en) 1979-06-29
MX3301E (en) 1980-09-03
FI760744A7 (en) 1976-09-22
AR213172A1 (en) 1978-12-29
AU501105B2 (en) 1979-06-14
FI61692B (en) 1982-05-31
NL7602891A (en) 1976-09-23
IT1061011B (en) 1982-10-20
NZ180251A (en) 1978-07-28
ZA761448B (en) 1977-03-30
AU1189976A (en) 1977-09-15
AT348163B (en) 1979-02-12
NO760994L (en) 1976-09-22
FR2304340A1 (en) 1976-10-15
DK88276A (en) 1976-09-22
IE42966B1 (en) 1980-11-19
SU614746A3 (en) 1978-07-05

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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