GB1505296A - 8-thiomethylergolines - Google Patents

8-thiomethylergolines

Info

Publication number
GB1505296A
GB1505296A GB23869/75A GB2386975A GB1505296A GB 1505296 A GB1505296 A GB 1505296A GB 23869/75 A GB23869/75 A GB 23869/75A GB 2386975 A GB2386975 A GB 2386975A GB 1505296 A GB1505296 A GB 1505296A
Authority
GB
United Kingdom
Prior art keywords
compound
coalk
alk
june
reacting
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
GB23869/75A
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.)
Eli Lilly and Co
Original Assignee
Eli Lilly and 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 Eli Lilly and Co filed Critical Eli Lilly and Co
Publication of GB1505296A publication Critical patent/GB1505296A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
    • C07D457/02—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hydrocarbon or substituted hydrocarbon radicals, attached in position 8
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1505296 8-Thiomethylergoline derivatives ELI LILLY & CO 3 June 1975 [6 June 1974] 23869/75 Heading C2C Novel compounds of the Formula II wherein R is H, CN, COalk, phenyl or alk; R<SP>1</SP> is H, Cl or Br; alk is C 1-3 alkyl and the dotted line is an optical bond and pharmaceuticallyacceptable acid addition salts thereof, may be prepared by reacting a compound of the Formula III wherein R 2 is methanesulphonyl or p-toluene sulphonyl with an alkali metal salt of a compound R<SP>3</SP>5H, wherein R<SP>3</SP> is CN, COalk, phenyl or alk, optionally followed where R<SP>3</SP> is -COalk by hydrolysis to produce a compound II in which R is H. D - 6 - Methyl - 8 - mesyloxymethylergoline and its 9,10-didehydro derivative are prepared by reacting the corresponding 8-hydroxymethyl compound with methane sulphonyl chloride. Pharmaceutical compositions of the compounds II with the usual excipients are prolactin inhibitors when administered parenterally.
GB23869/75A 1974-06-06 1975-06-03 8-thiomethylergolines Expired GB1505296A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US477136A US3901894A (en) 1974-06-06 1974-06-06 8-thiomethylergolines

Publications (1)

Publication Number Publication Date
GB1505296A true GB1505296A (en) 1978-03-30

Family

ID=23894677

Family Applications (1)

Application Number Title Priority Date Filing Date
GB23869/75A Expired GB1505296A (en) 1974-06-06 1975-06-03 8-thiomethylergolines

Country Status (27)

Country Link
US (1) US3901894A (en)
JP (1) JPS582946B2 (en)
AR (1) AR210736A1 (en)
AT (1) AT344333B (en)
AU (1) AU507574B2 (en)
BE (1) BE829887A (en)
BG (1) BG24812A3 (en)
CA (1) CA1071623A (en)
CH (1) CH617196A5 (en)
CS (1) CS199591B2 (en)
DD (1) DD120438A5 (en)
DE (1) DE2524575A1 (en)
DK (1) DK144160C (en)
ES (1) ES438313A1 (en)
FR (1) FR2273542A1 (en)
GB (1) GB1505296A (en)
HU (1) HU173590B (en)
IE (1) IE41474B1 (en)
IL (1) IL47424A (en)
NL (1) NL180911C (en)
PH (1) PH10992A (en)
PL (1) PL95738B1 (en)
RO (1) RO77543A (en)
SE (1) SE420095B (en)
SU (1) SU613724A3 (en)
YU (1) YU145575A (en)
ZA (1) ZA753638B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2125041A (en) * 1982-08-09 1984-02-29 Sandoz Ltd Ergot alkaloids

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4147789A (en) * 1974-03-14 1979-04-03 Sandoz Ltd. 6-Methyl-8-thiomethyl-ergolene derivatives
US3959288A (en) * 1974-12-13 1976-05-25 Eli Lilly And Company 8-Oxymethylergolines and process therefor
JPS5283894A (en) * 1976-01-01 1977-07-13 Lilly Co Eli 88thiomethyl ergoline
GB1549829A (en) * 1976-05-26 1979-08-08 Farmaceutici Italia 10'-methoxy-1',6'-dimethylergoline-8'-beta-methyl-amino(or thio)-pyrazines
IT1192260B (en) * 1977-07-05 1988-03-31 Simes ERGOLINE-2-THIOETHERS AND THEIR SULPHOXIDES DERIVATIVES
US4166182A (en) * 1978-02-08 1979-08-28 Eli Lilly And Company 6-n-propyl-8-methoxymethyl or methylmercaptomethylergolines and related compounds
US4180582A (en) * 1978-02-08 1979-12-25 Eli Lilly And Company 6-n-Propyl-8-methoxy-methyl or methylmercaptomethylergolines and related compounds as prolactin inhibitors and to treat Parkinson's syndrome
US4202979A (en) * 1979-01-11 1980-05-13 Eli Lilly And Company 6-Ethyl(or allyl)-8-methoxymethyl or methylmercaptomethylergolines and related compounds
US4246265A (en) * 1979-10-01 1981-01-20 Eli Lilly And Company 6-n-Propyl-8α-methoxymethyl or methylmercaptomethylergolines and related compounds
US4382940A (en) * 1979-12-06 1983-05-10 Farmitalia Carlo Erba S.P.A. Ercoline derivatives and therapeutic compositions having CNS affecting activity
DE3216870A1 (en) * 1982-05-03 1983-11-03 Schering AG, 1000 Berlin und 4709 Bergkamen PHARMACEUTICAL PREPARATIONS WITH A CYTOSTATIC EFFECT
FR2526797A1 (en) * 1982-05-12 1983-11-18 Roussel Uclaf NOVEL 9-OXALYSERGIC ACID DERIVATIVES, THEIR SALTS, PREPARATION METHOD, MEDICAMENT APPLICATION AND COMPOSITIONS COMPRISING THE SAME
GB8427536D0 (en) * 1984-10-31 1984-12-05 Lilly Industries Ltd Ergoline derivatives
US4675322A (en) * 1984-12-10 1987-06-23 Eli Lilly And Company 1-Substituted-6-n-propyl-8β-methylthio-methylergolines
US4801712A (en) * 1985-06-24 1989-01-31 Eli Lilly And Company 2-Alkyl(or phenyl)thio-6-n-alkylergolines are dopamine D-1 antagonists without D-2 agonist activity
FR2589734B1 (en) * 1985-11-13 1988-09-02 Roussel Uclaf USE OF ERGOLIN DERIVATIVES FOR OBTAINING A GERIATRIC MEDICINE
HU196394B (en) * 1986-06-27 1988-11-28 Richter Gedeon Vegyeszet Process for preparing 2-halogenated ergoline derivatives
WO2002100888A1 (en) * 2001-06-08 2002-12-19 Societe De Conseils De Recherches Et D'applications Scientifiques S.A.S. Somatostatin-dopamine chimeric analogs
EP1485382B1 (en) * 2002-03-15 2008-11-19 Antibioticos S.p.A. Process for the synthesis of pergolide
CN104768565B (en) 2012-11-01 2017-04-26 益普生制药股份有限公司 Somatostatin analogs and dimers thereof
TWI523863B (en) 2012-11-01 2016-03-01 艾普森藥品公司 Somatostatin-dopamine chimeric analogs
US20190374534A1 (en) 2018-06-08 2019-12-12 Boehringer Ingelheim Vetmedica Gmbh Liquid pharmaceutical compositions comprising pergolide

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH507248A (en) * 1967-03-16 1971-05-15 Spofa Vereinigte Pharma Werke Process for the preparation of D-6-methylergolin (I) ylacetic acid
DE1935556A1 (en) * 1969-07-12 1971-01-21 Hoechst Ag Process for the production of lysergol
JPS5012398A (en) * 1973-06-08 1975-02-07

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2125041A (en) * 1982-08-09 1984-02-29 Sandoz Ltd Ergot alkaloids

Also Published As

Publication number Publication date
CS199591B2 (en) 1980-07-31
ATA427975A (en) 1977-11-15
CA1071623A (en) 1980-02-12
YU145575A (en) 1982-02-28
DD120438A5 (en) 1976-06-12
BG24812A3 (en) 1978-05-12
IL47424A (en) 1979-11-30
IE41474B1 (en) 1980-01-16
RO77543A (en) 1982-02-26
CH617196A5 (en) 1980-05-14
IL47424A0 (en) 1975-08-31
DK144160B (en) 1981-12-28
NL180911C (en) 1987-05-18
DK249975A (en) 1975-12-07
HU173590B (en) 1979-06-28
AU507574B2 (en) 1980-02-21
ES438313A1 (en) 1977-05-16
AR210736A1 (en) 1977-09-15
FR2273542B1 (en) 1978-10-06
NL180911B (en) 1986-12-16
IE41474L (en) 1975-12-06
NL7506584A (en) 1975-12-09
JPS582946B2 (en) 1983-01-19
PL95738B1 (en) 1977-11-30
AU8182775A (en) 1976-12-09
SE7506327L (en) 1975-12-08
PH10992A (en) 1977-10-20
DK144160C (en) 1982-06-07
JPS50160300A (en) 1975-12-25
SU613724A3 (en) 1978-06-30
DE2524575A1 (en) 1975-12-18
US3901894A (en) 1975-08-26
ZA753638B (en) 1977-01-26
FR2273542A1 (en) 1976-01-02
BE829887A (en) 1975-12-05
AT344333B (en) 1978-07-10
SE420095B (en) 1981-09-14

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
SP Amendment (slips) printed
704A Declaration that licence is not available as of right for an excepted use (par. 4a/1977)
PCNP Patent ceased through non-payment of renewal fee