GB1431871A - 10-aza-11,12-secoprostaglandins and their production - Google Patents

10-aza-11,12-secoprostaglandins and their production

Info

Publication number
GB1431871A
GB1431871A GB266774A GB266774A GB1431871A GB 1431871 A GB1431871 A GB 1431871A GB 266774 A GB266774 A GB 266774A GB 266774 A GB266774 A GB 266774A GB 1431871 A GB1431871 A GB 1431871A
Authority
GB
United Kingdom
Prior art keywords
compounds
formula
alkyl
tetrahydropyranyloxy
butyl
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
GB266774A
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB1431871A publication Critical patent/GB1431871A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings 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
    • C07D309/10—Oxygen atoms
    • C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
    • C07C235/74—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • 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
    • C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
    • 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
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
    • 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
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
    • C07C53/19—Acids containing three or more carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyrane Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1431871 11,12-Secoprostaglandins MERCK & CO Inc 21 Jan 1974 [26 Jan 1973] 02667/74 Heading C2C The invention comprises 11,12-secoprostaglandins of the Formula I: in which R is COOY, wherein Y is H, a pharmaceutically acceptable cation or C 1-10 alkyl, CONHNH 2 or CONR<SP>6</SP>R<SP>7</SP>, wherein R<SP>6</SP> and R<SP>7</SP> each are H, C 1-4 alkyl or C 4-7 dialkylaminoalkyl; A is ethylene, trimethylene, α-methylethylene, #-methylethylene, α,α-dimethylethylene, #,#-dimethylethylene or oxymethylene; R<SP>1</SP> is H or CH 3 ; R<SP>2</SP> is H or C 1-3 alkyl; R<SP>3</SP> is H or CH 3 ; R<SP>4</SP> is H or C 1-5 alkanoyl; and R<SP>5</SP> is C 3-7 alkyl, 4- pentenyl or 5,5,5-trifluoropentyl; except that when R<SP>3</SP> is CH 3 , R<SP>5</SP> is not 4-pentenyl; and their preparation. Compounds of the above formula in which R<SP>3</SP> is H and R is COOH are obtained by reacting compounds of the Formula III: wherein R<SP>9</SP> is C 1-5 alkyl, with compounds of the formula R<SP>1</SP>(R<SP>2</SP>)NH, and subjecting the compound then obtained to basic hydrolysis and acidification. Compounds of the above Formula I in which R<SP>3</SP> is CH 3 , R<SP>6</SP> is C 3-7 alkyl or 5,5,5-trifluoropentyl and R is COOH are prepared by reacting compounds of the Formula IV: in which R<SP>10</SP> is C 3-7 alkyl or 5,5,5-trifluoropentyl with compounds of the formula R<SP>1</SP>(R<SP>2</SP>)NH, hydrating the product with mercuric oxide in aqueous tetrahydrofuran, followed by treatment with sodium borohydride, and subjecting the resulting compounds to basic hydrolysis and acidification. The compound in which R<SP>4</SP> is C 1-5 alkanoyl are made by acylating the corresponding compounds in which R<SP>4</SP> is H. The esters, amides and hydrazides of the above Formula I are prepared by standard methods. The following intermediates are also prepared: 3(S and R) - 3 - (2 - tetrahydropyranyloxy) - 1 - octyne; 4(S and R) - 1,1 - diethoxy- 4 - (2 - tetrahydropyranyloxyl - 2 - octyne; 4(S and R) - 4 - hydroxy - 2 - nonynal; 4(S and R) - 4 - (2 - tetrahydropyranyloxy - 2 - nonynal; 4(S and R) - 4 - (2 - tetrahydropyranyloxy)- nonanal; (4S and R) - 4 - (2 - tetrahydropyranyloxy) - 1 - nonanol; (4S and R) - 1- methylsulphonyloxy - 4 - (2 - tetrahydropyranyloxy)nonane; di-tert. - butyl 2 - [4(S and R) - (2 - tetrahydropyranyloxy)nonyl] - 2 - (6- ethoxycarbonylhexyl)malonate; di-tert.-butyl 2 - [4(S and R) - hydroxynonyl] - 2 - (6 - ethoxycarbonylhexyl)malonate; di-tert.-butyl 2-[4(S and R) - acetoxynonyl] - 2 - (6 - ethoxycarbonylhexyl)malonate; N - t - butyl - 3 - (8- carbamoyl - 12 - hydroxyheptadecanoyloxy)- crotonamide; compounds of the formulµ XIV, XV, XVI and XVII: acid chlorides of the Formulµ III and IV above; and compounds of the formula Pharmaceutical compositions, suitable for oral, parenteral, rectal or topical administration, contain the above compounds together with pharmaceutically acceptable carriers. The compounds are used to improve renal function, for treatment of hypertension, for fertility control and prevention of thrombus formation.
GB266774A 1973-01-26 1974-01-21 10-aza-11,12-secoprostaglandins and their production Expired GB1431871A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US32693473A 1973-01-26 1973-01-26

Publications (1)

Publication Number Publication Date
GB1431871A true GB1431871A (en) 1976-04-14

Family

ID=23274398

Family Applications (1)

Application Number Title Priority Date Filing Date
GB266774A Expired GB1431871A (en) 1973-01-26 1974-01-21 10-aza-11,12-secoprostaglandins and their production

Country Status (7)

Country Link
JP (1) JPS49109318A (en)
CH (1) CH602591A5 (en)
DE (1) DE2402742A1 (en)
FR (1) FR2215224B1 (en)
GB (1) GB1431871A (en)
NL (1) NL7400198A (en)
SE (1) SE408639B (en)

Also Published As

Publication number Publication date
FR2215224A1 (en) 1974-08-23
DE2402742A1 (en) 1974-08-01
NL7400198A (en) 1974-07-30
JPS49109318A (en) 1974-10-17
SE408639B (en) 1979-06-25
CH602591A5 (en) 1978-07-31
FR2215224B1 (en) 1976-09-03

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee