ES416865A1 - 15-substituted-omega-pentanorprostaglandins - Google Patents

15-substituted-omega-pentanorprostaglandins

Info

Publication number
ES416865A1
ES416865A1 ES416865A ES416865A ES416865A1 ES 416865 A1 ES416865 A1 ES 416865A1 ES 416865 A ES416865 A ES 416865A ES 416865 A ES416865 A ES 416865A ES 416865 A1 ES416865 A1 ES 416865A1
Authority
ES
Spain
Prior art keywords
alpha
compound
represent
indicated above
hydrogen
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
ES416865A
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Spanish (es)
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.)
Pfizer Inc
Original Assignee
Pfizer 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 Pfizer Inc filed Critical Pfizer Inc
Publication of ES416865A1 publication Critical patent/ES416865A1/en
Expired legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/93Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
    • C07D307/935Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C405/00Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D309/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02Heterocyclic 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
    • C07D309/08Heterocyclic 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
    • C07D309/10Oxygen atoms
    • C07D309/12Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D317/00Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/60Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/38Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40Esters thereof
    • C07F9/4003Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4056Esters of arylalkanephosphonic acids
    • C07F9/4059Compounds containing the structure (RY)2P(=X)-(CH2)n-C(=O)-(CH2)m-Ar, (X, Y = O, S, Se; n>=1, m>=0)
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6553Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
    • C07F9/655345Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B63SHIPS OR OTHER WATERBORNE VESSELS; RELATED EQUIPMENT
    • B63BSHIPS OR OTHER WATERBORNE VESSELS; EQUIPMENT FOR SHIPPING 
    • B63B2211/00Applications
    • B63B2211/02Oceanography

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Furan Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Compounds Of Unknown Constitution (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

A process for preparing ω -pentanorprostaglandins substituted at position 15 having the following structure: **(See formula)** in which: Ar is alpha- or beta-furyl; alpha- or beta-thienyl; alpha- or beta-naphthyl; phenyl; 3,4-dimethoxyphenyl, 3,4-methylenedioxyphenyl; 3,4,5-trimethoxyphenyl or monosubstituted phenyl in which the substituent is halo, trifluoromethyl, phenyl, lower alkyl or lower alkoxy; n is an integer from 0 to 5, provided that when Ar is phenyl, substituted phenyl, or naphthyl, n is 0 or 1; R is hydrogen or lower alkyl; W is a single tie or a double cis tie; Z is a single or double trans ligature when n is an integer from 1 to 5, and Z is a single ligature when n is zero; M is keto, (see formula); N and L together form a single bond or N is alpha-hydroxyl when L is hydrogen and in which: L, M, and N are selected to complete the structure of a series A, E, or F prostaglandin, the lower alkanoyl, formyl, or benzoyl esters of any free hydroxyl groups at positions C9-, C11, and C15 and their salts pharmaceutically acceptable, characterized by the fact that: a) when N is alpha-hydroxy and L is hydrogen and Ar, n, M, W and Z represent what is indicated above, said compound is prepared by treating the 11-, and 11- and 15-tetrahydropyranyl ethers of a compound of formula I, with an appropriate acid; b) when N and L, together, form a single bond, M is keto and Ar, n, R, W and Z represent what is indicated above, said compound is prepared by the reaction of a compound of formula I, in the which N is alpha-hydroxy and L is hydrogen, M is keto and Ar, n, R, W and Z represent as indicated above, with an appropriate dehydration agent; c) when N is alpha-hydroxy and L is hydrogen, M is (see formula) and Ar, n, R, W and Z represent what is indicated above, said compound is prepared by the reaction of a compound of formula I, in which N is alpha-hydroxy and L is hydrogen, M is Keto, Ar, n, R, W and Z represent as indicated above with a suitable reducing agent and, if appropriate, the 9alpha- and 9beta- isomers are separated. d) when N is alpha-hydroxy, L is hydrogen, Ar, R, n and M represent what is indicated above, and W and Z are simple bonds, said compound is prepared by the catalytic reduction of a compound of formula I, in which Ar, R, n and M represent what is indicated above, W is a single ligature or a double cis ligature when Z is a double trans ligature, and Z is a single ligature when W is a cis double ligature; e) when N is alpha-hydroxy, L is hydrogen, Ar, R, n and M represent what is indicated above, W is a single ligation and Z is a trans double ligation, said compound is prepared by the selective reduction of a compound of formula I, in which Ar, R, n and M represent what is indicated above and W and Z are double bonds; and, if appropriate, 9alpha-, 11alpha-, and 15alpha-alkanoyl, formyl, or benzoyl esters of any free hydroxyl groups are prepared by the reaction of said compounds with the appropriate acylating agents and, if desired, prepared the pharmaceutically acceptable salts of these compounds. (Machine-translation by Google Translate, not legally binding)
ES416865A 1972-07-13 1973-07-03 15-substituted-omega-pentanorprostaglandins Expired ES416865A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US27122072A 1972-07-13 1972-07-13

Publications (1)

Publication Number Publication Date
ES416865A1 true ES416865A1 (en) 1976-03-01

Family

ID=23034697

Family Applications (4)

Application Number Title Priority Date Filing Date
ES416865A Expired ES416865A1 (en) 1972-07-13 1973-07-03 15-substituted-omega-pentanorprostaglandins
ES437038A Expired ES437038A1 (en) 1972-07-13 1975-04-26 15-substituted-omega-pentanorprostaglandins
ES437039A Expired ES437039A1 (en) 1972-07-13 1975-04-26 15-substituted-omega-pentanorprostaglandins
ES437037A Expired ES437037A1 (en) 1972-07-13 1975-04-26 15-substituted-omega-pentanorprostaglandins

Family Applications After (3)

Application Number Title Priority Date Filing Date
ES437038A Expired ES437038A1 (en) 1972-07-13 1975-04-26 15-substituted-omega-pentanorprostaglandins
ES437039A Expired ES437039A1 (en) 1972-07-13 1975-04-26 15-substituted-omega-pentanorprostaglandins
ES437037A Expired ES437037A1 (en) 1972-07-13 1975-04-26 15-substituted-omega-pentanorprostaglandins

Country Status (25)

Country Link
JP (4) JPS5241257B2 (en)
AR (2) AR209064A1 (en)
AT (1) AT367033B (en)
BE (1) BE802231A (en)
CA (1) CA1041495A (en)
CH (1) CH593254A5 (en)
CS (1) CS201027B2 (en)
DD (2) DD109210A5 (en)
DE (1) DE2334945A1 (en)
ES (4) ES416865A1 (en)
FI (1) FI57583C (en)
FR (1) FR2192834B1 (en)
GB (1) GB1446341A (en)
HU (4) HU171946B (en)
IE (1) IE37909B1 (en)
IL (2) IL42691A (en)
IN (1) IN138789B (en)
LU (1) LU68015A1 (en)
NL (1) NL7309792A (en)
NO (2) NO143741C (en)
PH (1) PH11461A (en)
SE (3) SE7705945L (en)
SU (4) SU644384A3 (en)
YU (1) YU187773A (en)
ZA (1) ZA734769B (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1386146A (en) * 1972-05-03 1975-03-05 Ici Ltd Cyclopentane derivatives
DE2463432C2 (en) * 1974-04-03 1987-06-19 Hoechst Ag, 6230 Frankfurt, De
DE2416193C2 (en) 1974-04-03 1985-08-14 Hoechst Ag, 6230 Frankfurt Prostaglandin analogs, processes for their preparation and their use as cytoprotective agents
ZA747723B (en) * 1974-12-11 1976-11-24 Pfizer 11-desoxy-15-substituted-omega-pentanor prostaglandins
US4149006A (en) * 1977-01-24 1979-04-10 G. D. Searle & Co. Prostaglandin derivatives having alkynyl, hydroxy and aryloxy junctions in the 2β side chain
GB8329559D0 (en) * 1983-11-04 1983-12-07 Erba Farmitalia Furyl derivatives of 16-substituted prostaglandins preparations
SE9002596D0 (en) * 1990-08-08 1990-08-08 Pharmacia Ab A METHOD OF SYNTHESIS OF PROSTAGLANDIN DERIVATIVES
US5972991A (en) * 1992-09-21 1999-10-26 Allergan Cyclopentane heptan(ene) oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents
US6602900B2 (en) 1992-09-21 2003-08-05 Allergan, Inc. Cyclopentane heptan(ENE)oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents
KR100578616B1 (en) * 2004-07-23 2006-05-10 한미약품 주식회사 Method for the preparation of d-erythro-2,2-difluoro-2-deoxy-1-oxoribose
BR112016013594A8 (en) * 2013-12-13 2020-05-19 Allergan Inc crystalline forms of a dihydroxy cyclopentyl alpha compound, omega-disubstituted, pharmaceutical composition, methods for preparing and using them

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1324737A (en) * 1970-11-02 1973-07-25 Upjohn Co Prostaglandins and the preparation thereof
GB1386146A (en) * 1972-05-03 1975-03-05 Ici Ltd Cyclopentane derivatives
IL42373A (en) * 1972-06-02 1977-08-31 Pfizer Oxaprostagliandins and their preparation

Also Published As

Publication number Publication date
IL42691A0 (en) 1973-10-25
FR2192834B1 (en) 1979-04-06
HU172058B (en) 1978-05-28
IL50308A0 (en) 1976-10-31
FI57583B (en) 1980-05-30
HU171156B (en) 1977-11-28
DD109210A5 (en) 1974-10-20
YU187773A (en) 1982-02-25
NO144830C (en) 1981-11-18
FI57583C (en) 1980-09-10
IE37909B1 (en) 1977-11-09
IN138789B (en) 1976-04-03
HU171946B (en) 1978-04-28
NL7309792A (en) 1974-01-15
JPS5241257B2 (en) 1977-10-17
SE7705945L (en) 1977-05-20
JPS4992053A (en) 1974-09-03
NO143741B (en) 1980-12-29
DE2334945A1 (en) 1974-03-07
CH593254A5 (en) 1977-11-30
SE7705946L (en) 1977-05-20
ZA734769B (en) 1974-06-26
LU68015A1 (en) 1974-01-21
SU584791A3 (en) 1977-12-15
CS201027B2 (en) 1980-10-31
DD116459A5 (en) 1975-11-20
HU171158B (en) 1977-11-28
CA1041495A (en) 1978-10-31
AR214383A1 (en) 1979-06-15
FR2192834A1 (en) 1974-02-15
ES437039A1 (en) 1977-01-01
BE802231A (en) 1974-01-14
NO743492L (en) 1974-01-15
ES437038A1 (en) 1977-01-01
AU5778473A (en) 1975-01-09
PH11461A (en) 1978-02-01
SE7705947L (en) 1977-05-20
JPS5293753A (en) 1977-08-06
SU645563A3 (en) 1979-01-30
JPS52122349A (en) 1977-10-14
SU644384A3 (en) 1979-01-25
GB1446341A (en) 1976-08-18
ES437037A1 (en) 1977-01-01
SU645564A3 (en) 1979-01-30
ATA620773A (en) 1981-10-15
AR209064A1 (en) 1977-03-31
NO144830B (en) 1981-08-10
NO143741C (en) 1981-04-08
AT367033B (en) 1982-05-25
IL42691A (en) 1979-07-25
IE37909L (en) 1974-01-13
JPS5297958A (en) 1977-08-17

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