GB1345546A - Dihydrolysergic and -isolysergic acid derivatives - Google Patents

Dihydrolysergic and -isolysergic acid derivatives

Info

Publication number
GB1345546A
GB1345546A GB1502471A GB1502471A GB1345546A GB 1345546 A GB1345546 A GB 1345546A GB 1502471 A GB1502471 A GB 1502471A GB 1502471 A GB1502471 A GB 1502471A GB 1345546 A GB1345546 A GB 1345546A
Authority
GB
United Kingdom
Prior art keywords
group
formula
acid
pcl
liquid ammonia
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
GB1502471A
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.)
Richter Gedeon Vegyeszeti Gyar Nyrt
Original Assignee
Richter Gedeon Vegyeszeti Gyar RT
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 Richter Gedeon Vegyeszeti Gyar RT filed Critical Richter Gedeon Vegyeszeti Gyar RT
Publication of GB1345546A publication Critical patent/GB1345546A/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
    • C07D457/04—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid 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 in position 8
    • 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
    • C07D457/04—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid 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 in position 8
    • C07D457/06—Lysergic acid amides
    • 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
    • C07D457/04—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid 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 in position 8
    • C07D457/06—Lysergic acid amides
    • C07D457/08—Lysergic acid amides in which the amide nitrogen is a member of a heterocyclic ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1345546 Dihydro-lysergic and isolysergic acid derivatives RICHTER GEDEON VEGYESZETI GYAR RT 14 May 1971 [18 May 1970] 15024/71 Heading C2C Novel compounds of the Formula (I) and their acid addition salts with organic and inorganic acids, where R 1 is H or CH 3 , R 2 is a straight or branched aralkylamino group substituted by at least one -OH group; or a group of one of the Formulµ III to XII and when R 1 is H, R 2 may also denote a straight or branched chain alkylamino group substituted by at least two OH groups, may be obtained by either (a) hydrogenating a compound of general Formula II or a salt thereof in liquid ammonia or in a solution of liquid ammonia in an organic solvent, with an alkali metal, or (b) for products of Formula I in which R 2 has the Formula III, VII or XI, reacting a compound of Formula I, wherein R 2 is OH with PCl 5 and PCl 3 to form an acid chloride of Formula I in which R 2 is Cl, and reacting with an amino compound R<SP>1</SP> 2 H, wherein R<SP>1</SP> 2 is one of the groups III, VII or XI in which the hydroxymethyl group is replaced by a carboxymethyl group, the latter group being subsequently reduced by reaction with a borohydride to the required hydroxymethyl group. Compounds in which R 1 is H may be methylated in the presence of a strong, e.g. using CH 3 I. The products show specific, marked serotoninantagonistic effect without deleterious effect on the central nervous system, heart, kidneys or great arteries. An intermediate, 1-methyl-dihydrolysergic acid, is obtained by hydrogenating lysergic acid with sodium metal in liquid ammonia and methylating the product with CH 3 I. The acid may be reacted with PCl 5 and PCl 3 to form 1-methyldihydrolysergic acid chloride hydrochloride.
GB1502471A 1970-05-18 1971-05-14 Dihydrolysergic and -isolysergic acid derivatives Expired GB1345546A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
HUGO001135 1970-05-18

Publications (1)

Publication Number Publication Date
GB1345546A true GB1345546A (en) 1974-01-30

Family

ID=10996683

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1502471A Expired GB1345546A (en) 1970-05-18 1971-05-14 Dihydrolysergic and -isolysergic acid derivatives

Country Status (12)

Country Link
JP (1) JPS5634598B1 (en)
AT (1) AT347047B (en)
CA (1) CA924306A (en)
CH (2) CH567506A5 (en)
CS (1) CS179371B2 (en)
DE (1) DE2124640C2 (en)
DK (1) DK142874B (en)
GB (1) GB1345546A (en)
NL (1) NL172825C (en)
SE (2) SE396753B (en)
SU (1) SU400091A3 (en)
YU (1) YU35770B (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4005089A (en) * 1974-05-28 1977-01-25 Richter Gedeon Vegyeszeti Gyar Rt. Compounds with ergoline skeleton
US4064249A (en) * 1974-05-28 1977-12-20 Richter Gedeon Vegyeszeti Gyar Rt. Compounds with ergoline skeleton
US5441961A (en) * 1992-08-27 1995-08-15 Eli Lilly And Company Substituted cyclo or bicycloalkylamides of (8β)-6-(substituted) ergolines
US20170174684A1 (en) * 2015-01-20 2017-06-22 Xoc Pharmaceuticals, Inc. Ergoline compounds and uses thereof
US9777016B2 (en) 2015-01-20 2017-10-03 Xoc Pharmaceuticals, Inc. Isoergoline compounds and uses thereof
US10301311B2 (en) 2017-06-01 2019-05-28 Xoc Pharmaceuticals, Inc. Polycyclic compounds and uses thereof

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU172649B (en) * 1975-04-24 1978-11-28 Gyogyszerkutato Intezet Process for producing new, biologically active lysergamides
DE3001752A1 (en) * 1980-01-16 1981-07-30 Schering Ag Berlin Und Bergkamen, 1000 Berlin METHOD FOR PRODUCING 8 (ALPHA) SUBSTITUTED 6-METHYLERGOLINES
NL189462C (en) * 1980-04-03 1993-04-16 Erba Carlo Spa ERGOLINE DERIVATIVES WITH ANTIPROLACTINIC AND / OR ANTIHYPERTENSIVE PROPERTIES AND PHARMACEUTICAL PREPARATION THEREOF.
US4902691A (en) * 1988-12-19 1990-02-20 Eli Lilly And Company Heteroalkylamides of (8-β)-1-alkyl-6-(substituted)ergolines useful for blocking 5HT2 receptors
US4914107A (en) * 1989-01-17 1990-04-03 Eli Lilly And Company Method for selectively blocking 5-HT2 receptors

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT192546B (en) * 1956-02-27 1957-10-25 Anton Von Waldheim Chemisch Ph Process for the preparation of dihydrolysergic acid and its derivatives

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4005089A (en) * 1974-05-28 1977-01-25 Richter Gedeon Vegyeszeti Gyar Rt. Compounds with ergoline skeleton
US4064249A (en) * 1974-05-28 1977-12-20 Richter Gedeon Vegyeszeti Gyar Rt. Compounds with ergoline skeleton
US5441961A (en) * 1992-08-27 1995-08-15 Eli Lilly And Company Substituted cyclo or bicycloalkylamides of (8β)-6-(substituted) ergolines
US5739146A (en) * 1992-08-27 1998-04-14 Eli Lilly And Company Substituted cyclo or bicycloalkylamides of (8β)-6-(substituted) ergolines
US9815830B2 (en) 2015-01-20 2017-11-14 Xoc Pharmaceuticals, Inc. Isoergoline compounds and uses thereof
US9777016B2 (en) 2015-01-20 2017-10-03 Xoc Pharmaceuticals, Inc. Isoergoline compounds and uses thereof
US20170174684A1 (en) * 2015-01-20 2017-06-22 Xoc Pharmaceuticals, Inc. Ergoline compounds and uses thereof
US9938277B2 (en) * 2015-01-20 2018-04-10 Xoc Pharmaceuticals, Inc. Ergoline compounds and uses thereof
US9951070B2 (en) 2015-01-20 2018-04-24 Xoc Pharmaceuticals, Inc. Ergoline compounds and uses thereof
US10246458B2 (en) 2015-01-20 2019-04-02 Xoc Pharmaceuticals, Inc. Ergoline compounds and uses thereof
US10308651B2 (en) 2015-01-20 2019-06-04 Xoc Pharmaceuticals, Inc. Ergoline compounds and uses thereof
US10464936B2 (en) 2015-01-20 2019-11-05 Xoc Pharmaceuticals, Inc. Ergoline compounds and uses thereof
US10703753B2 (en) 2015-01-20 2020-07-07 Xoc Pharmaceuticals, Inc. Ergoline compounds and uses thereof
US10301311B2 (en) 2017-06-01 2019-05-28 Xoc Pharmaceuticals, Inc. Polycyclic compounds and uses thereof
US10815235B2 (en) 2017-06-01 2020-10-27 Xoc Pharmaceuticals Polycyclic compounds and uses thereof

Also Published As

Publication number Publication date
SE396753B (en) 1977-10-03
DK142874B (en) 1981-02-16
NL172825B (en) 1983-06-01
SU400091A3 (en) 1973-10-03
NL7106834A (en) 1971-11-22
SE416302B (en) 1980-12-15
CA924306A (en) 1973-04-10
CH590277A5 (en) 1977-07-29
YU35770B (en) 1981-06-30
DE2124640A1 (en) 1972-11-02
AT347047B (en) 1978-12-11
YU122971A (en) 1980-10-31
ATA428771A (en) 1978-04-15
NL172825C (en) 1983-11-01
CH567506A5 (en) 1975-10-15
CS179371B2 (en) 1977-10-31
DE2124640C2 (en) 1983-02-03
DK142874C (en) 1981-09-28
JPS5634598B1 (en) 1981-08-11

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee