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SE8201649L - PROCEDURE FOR THE PREPARATION OF PROSTACYCLINE DERIVATIVES - Google Patents

PROCEDURE FOR THE PREPARATION OF PROSTACYCLINE DERIVATIVES

Info

Publication number
SE8201649L
SE8201649L SE8201649A SE8201649A SE8201649L SE 8201649 L SE8201649 L SE 8201649L SE 8201649 A SE8201649 A SE 8201649A SE 8201649 A SE8201649 A SE 8201649A SE 8201649 L SE8201649 L SE 8201649L
Authority
SE
Sweden
Prior art keywords
denotes
ddr
formula
alkyl
carbon atoms
Prior art date
Application number
SE8201649A
Other languages
Swedish (sv)
Inventor
N A Nelson
U F Axen
Original Assignee
Upjohn Co
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 Upjohn Co filed Critical Upjohn Co
Publication of SE8201649L publication Critical patent/SE8201649L/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic 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
    • C07D307/93—Heterocyclic 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
    • C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C405/00—Compounds 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
    • C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
    • C07C405/0041—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic 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
    • C07D307/93—Heterocyclic 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
    • C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
    • C07D307/937—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans with hydrocarbon or substituted hydrocarbon radicals directly attached in position 2, e.g. prostacyclins
    • 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
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C07F3/10—Mercury compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Analogues of 5,6-dihydroprostacyclin of the formula in which the substituents are defined in claim 1, are prepared. These compounds are obtained by halogenating and cyclising a compound of the formula and subsequently reductively dehalogenating the reaction product, with the formation of the desired ether, or by converting the said compound LXII into a corresponding mercury compound and then subjecting the reaction product to the removal of mercury by reduction. The compounds which are obtained may be used for the same pharmacological purposes as the known prostaglandins.

Claims (1)

Pat entkravPat entkrav 1. FOrfarande fdr framsttllning as en fdrening med formeln dLr R2 betecknar (1) R -C-CgH2I 16 fluoro, kloro, trifluorometyl eller -0R7- dPr R7 betecknar alkyl med 1 - 6 kolatomer, och ddr s betecknar 0, 1, 2 eller 3, varvid hOgst tva T bar annan betydelse On alkyl och ddr ndr s betecknar 2 eller 3 T antingen Pr lika eller olika orb dEr betecknar /••■ H , 63094eller 63014 ddr R3 betecknar vdte eller alkyl med 1 - 4 kolatomer, ddr R4 betecknar vdte, tetrahydropyran-2-yl, tetrahydrofuranyl, 1-etoxietyl eller en grupp med formeln ii 10 0-C R,Rio dal, 16 beteeknar alkyl med 1 - 18 kolatomer, cyklcalkyl mod 3 - kolatomer, aralkyl med 7 - 12 kolatomer, fenyl eller fenyl substituerad med 1, 2 eller 3 alkyl med 1 - 4 kolatomer, dAr 69 och R dr like eller olika, cab betecknar state, alkyl med 1 - 4 kolatomer, fenyl eller fenyl substituerad med 1, 2 eller 3 all, 1 - 4 Ro/r eller ddr 69 ooh Rio tillsag- mans beteckn-(CH2)a- elle_CH2)b-0-(CH2)c- ddr a heteck- nar 3, 4 eller 5, b betecknar 1, 2 eller 3, c betecknar 1, 2 Rd oweller 3 och b plus c betecknar 2, 3 eller 4 och clar Ri, beteck-dar 23 tidigare definierats och dirR har samma betydelse nar 'crate eller fenyl; ddrbetecknarsom R4 med det undantaget att det inte innefattar cite, omvandlas till ett tosylat med formeln ai2 OR ' 4 024 ryCH2CH2-0Ts CH, ddr 01, R,,°oh,/ tidigare definierats och dar Ts betecknar p-to usulfonylgruppen; och eventuellt aylagsnande av den blockerande gruppen R fir bildning an en forening med formeln dar 2, R2, a ach.,, tidigare definierats. , eller ddr R4 tidigare definierats; dar Ts betecknar p-toluensulfonyl- gruppen ochbetecknar anslutning i alfa- eller beta- -kOnfiguration,kannetecknatay att en fire- fling med formeln ddr 22,och,,., tidigare definierats och ddr Qi beteck- oar V's■ HH , 230242 , ei.23OR /0-CH ryCH2C1-12-0H —CH2 C-R, 01A process for the preparation of a compound of the formula dLr R2 represents (1) R -C-CgH2I 16 fluoro, chloro, trifluoromethyl or -OR7- dPr R7 represents alkyl having 1 to 6 carbon atoms, and ddr s represents 0, 1, 2 or 3, where at most two T had a different meaning On alkyl and ddr ndr s denotes 2 or 3 T either Pr equal or different orb dEr denotes / •• ■ H, 63094or 63014 ddr R3 denotes vdte or alkyl with 1 - 4 carbon atoms, ddr R4 represents hydrogen, tetrahydropyran-2-yl, tetrahydrofuranyl, 1-ethoxyethyl or a group of the formula II 10-CR, R , phenyl or phenyl substituted with 1, 2 or 3 alkyl having 1 to 4 carbon atoms, dAr 69 and R 3 having the same or different, cab denotes state, alkyl having 1 - 4 carbon atoms, phenyl or phenyl substituted with 1, 2 or 3 all, 1 - 4 Ro / r or ddr 69 ooh Rio denominator denotes- (CH2) a- or_CH2) b-O- (CH2) c- ddr a denotes 3, 4 or 5, b denotes 1, 2 or r 3, c denotes 1, 2 Rd oweller 3 and b plus c denotes 2, 3 or 4 and clar Ri, denotes 23 previously defined and dirR has the same meaning when 'crate or phenyl; the denominator as R4 with the exception that it does not include cite, is converted to a tosylate of the formula ai2 OR '4,024 ryCH2CH2-0Ts CH, ddr 01, R and optionally depositing the blocking group R to form a compound of formula wherein 2, R 2, a. , or ddr R4 previously defined; where Ts denotes the p-toluenesulfonyl group and denotes connection in alpha or beta configuration, it may indicate that a fire-fling of the formula ddr 22, and ,,., previously defined and ddr Qi denotes V's ■ HH, 230242, ei .23OR / 0-CH ryCH2C1-12-0H —CH2 CR, 01
SE8201649A 1976-06-01 1982-03-16 PROCEDURE FOR THE PREPARATION OF PROSTACYCLINE DERIVATIVES SE8201649L (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US69139976A 1976-06-01 1976-06-01
US69140076A 1976-06-01 1976-06-01
US78814677A 1977-04-19 1977-04-19
US78814777A 1977-04-19 1977-04-19

Publications (1)

Publication Number Publication Date
SE8201649L true SE8201649L (en) 1982-03-16

Family

ID=27505431

Family Applications (3)

Application Number Title Priority Date Filing Date
SE7706245A SE436744B (en) 1976-06-01 1977-05-27 PROCEDURE FOR THE PREPARATION OF PROSTACYCLINE DERIVATIVES
SE7811142A SE432101B (en) 1976-06-01 1978-10-26 PROSTACYCLINE DERIVATIVES FOR USE TO REGULATE THE REPRODUCTION CYCLE OF MENSTRUCTING DOGS
SE8201649A SE8201649L (en) 1976-06-01 1982-03-16 PROCEDURE FOR THE PREPARATION OF PROSTACYCLINE DERIVATIVES

Family Applications Before (2)

Application Number Title Priority Date Filing Date
SE7706245A SE436744B (en) 1976-06-01 1977-05-27 PROCEDURE FOR THE PREPARATION OF PROSTACYCLINE DERIVATIVES
SE7811142A SE432101B (en) 1976-06-01 1978-10-26 PROSTACYCLINE DERIVATIVES FOR USE TO REGULATE THE REPRODUCTION CYCLE OF MENSTRUCTING DOGS

Country Status (13)

Country Link
JP (1) JPS5936912B2 (en)
AU (1) AU508891B2 (en)
BE (1) BE855224A (en)
CA (1) CA1196632A (en)
CH (1) CH640847A5 (en)
DE (1) DE2724555A1 (en)
FR (1) FR2353543B1 (en)
GB (1) GB1554048A (en)
IE (1) IE45604B1 (en)
IL (1) IL52099A (en)
MX (1) MX4813E (en)
NL (1) NL7705991A (en)
SE (3) SE436744B (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL51189A (en) * 1976-02-04 1985-08-30 Upjohn Co Prostaglandin analogs
FI71138C (en) * 1976-12-31 1986-11-24 Erba Farmitalia FOERFARANDE FOER FRAMSTAELLNING AV TERAPEUTISKT ACTIVE BISYCLISKA PROSTAGLANDINER
AU524786B2 (en) * 1977-03-07 1982-10-07 The Upjohn Company Prostacyclins
DE2743283A1 (en) * 1977-09-27 1979-04-05 Hoechst Ag NEW PROSTACYCLIN ANALOG
DE2811950A1 (en) * 1978-03-18 1979-12-13 Hoechst Ag NEW PROSTACYCLIN ANALOGS
US4237060A (en) 1979-03-23 1980-12-02 Hoffmann-La Roche Inc. Prostacyclin analogs
WO2001010433A1 (en) * 1999-08-05 2001-02-15 Teijin Limited Neuropathy improvers containing nitrogenous compounds as the active ingredient

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS537665A (en) * 1976-05-11 1978-01-24 Wellcome Found Novel ether* its preparation and its use

Also Published As

Publication number Publication date
DE2724555A1 (en) 1977-12-15
BE855224A (en) 1977-11-30
IE45604B1 (en) 1982-10-06
GB1554048A (en) 1979-10-17
CH640847A5 (en) 1984-01-31
SE436744B (en) 1985-01-21
AU508891B2 (en) 1980-04-03
FR2353543B1 (en) 1986-02-21
SE7811142L (en) 1978-11-28
AU2508677A (en) 1978-11-16
FR2353543A1 (en) 1977-12-30
IL52099A0 (en) 1977-07-31
MX4813E (en) 1982-10-19
IL52099A (en) 1985-03-31
JPS5936912B2 (en) 1984-09-06
CA1196632A (en) 1985-11-12
JPS52156854A (en) 1977-12-27
NL7705991A (en) 1977-12-05
SE7706245L (en) 1977-12-16
SE432101B (en) 1984-03-19
IE45604L (en) 1977-12-01

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