US3770724A - Process for preparing pentacyclic alkaloids - Google Patents

Process for preparing pentacyclic alkaloids Download PDF

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Publication number
US3770724A
US3770724A US00126929A US3770724DA US3770724A US 3770724 A US3770724 A US 3770724A US 00126929 A US00126929 A US 00126929A US 3770724D A US3770724D A US 3770724DA US 3770724 A US3770724 A US 3770724A
Authority
US
United States
Prior art keywords
ethyl
oxo
quinolizine
eburnane
cis
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 - Lifetime
Application number
US00126929A
Other languages
English (en)
Inventor
E Toromanoff
J Warnant
A Farcilli
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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
Priority claimed from FR7011406A external-priority patent/FR2081593A1/fr
Priority claimed from FR7032889A external-priority patent/FR2104959A2/fr
Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA
Application granted granted Critical
Publication of US3770724A publication Critical patent/US3770724A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
    • C07D471/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D461/00—Heterocyclic compounds containing indolo [3,2,1-d,e] pyrido [3,2,1,j] [1,5]-naphthyridine ring systems, e.g. vincamine
US00126929A 1970-03-31 1971-03-22 Process for preparing pentacyclic alkaloids Expired - Lifetime US3770724A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR7011406A FR2081593A1 (en) 1970-03-31 1970-03-31 Vincamine process
FR7032889A FR2104959A2 (en) 1970-09-10 1970-09-10 Vincamine process

Publications (1)

Publication Number Publication Date
US3770724A true US3770724A (en) 1973-11-06

Family

ID=26215644

Family Applications (1)

Application Number Title Priority Date Filing Date
US00126929A Expired - Lifetime US3770724A (en) 1970-03-31 1971-03-22 Process for preparing pentacyclic alkaloids

Country Status (16)

Country Link
US (1) US3770724A (sv)
JP (3) JPS5144960B1 (sv)
AT (1) AT309699B (sv)
BE (1) BE765006A (sv)
CA (1) CA937570A (sv)
CH (1) CH546777A (sv)
DE (3) DE2167044C2 (sv)
DK (1) DK149345C (sv)
GB (3) GB1351261A (sv)
HU (1) HU163769B (sv)
IL (1) IL36474A (sv)
IT (1) IT8048032A0 (sv)
NL (1) NL158497B (sv)
PL (1) PL83152B1 (sv)
SE (2) SE390414B (sv)
SU (1) SU505365A3 (sv)

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3884927A (en) * 1972-04-14 1975-05-20 Roussel Uclaf Process for the preparation of vincamine
US3979395A (en) * 1974-08-09 1976-09-07 Buskine S.A. Process for the preparation of vincamine and other indole alkaloids
US3987049A (en) * 1974-01-31 1976-10-19 Synthelabo Esters of dihydroapovincaminic acid
US4033969A (en) * 1972-06-19 1977-07-05 Agence Nationale De Valorisation De La Recherche (Anvar) Vincamine derivatives
US4283401A (en) * 1978-07-12 1981-08-11 Richter Gedeon Vegyeszeti Gyar Rt Process for the preparation of 11-bromo-vincaminic acid ester derivatives and their use in protecting animals against cerebral hypoxy
US4285950A (en) * 1979-08-13 1981-08-25 Richter Gedeon Vegyeszeti Gyar Rt 10-halo-E-homoeburnane derivatives, a process for the preparation thereof, a process for the use thereof as vasodilators, and vasodilating compositions thereof
US4315011A (en) * 1978-07-12 1982-02-09 Richter Gedeon Vegyeszeti Gyar Rt. 1-Alkyl-9-bromohexahydroindolo quinolizium salts and use thereof to increase blood flow
US4382936A (en) * 1978-11-20 1983-05-10 Sumitomo Chemical Company, Limited Cerebral vasodilator eburnane derivatives
US4399069A (en) * 1980-10-12 1983-08-16 Richter Gedeon Vegyeszeti Gyar Rt. Process for an enantioselective synthesis of optically active 14-oxo-E-homo-eburnane derivatives
US4428877A (en) 1978-07-12 1984-01-31 Richter Gedeon Vegyeszeti Gyar Rt. Cis-10-bromo-E-homoeburnanes
US4464534A (en) * 1981-09-30 1984-08-07 Richter Gedeon Vegyeszeti Gyar Rt. Process for the preparation of vincaminic acid esters
US4464535A (en) * 1981-03-11 1984-08-07 Richter Gedeon Vegyeszeti Gyar Rt. Process for the preparation of eburnamonine derivatives
US4614824A (en) * 1982-06-30 1986-09-30 Richter Gedeon Vegyeszeti Gyar R.T. Novel apovincaminic acid derivatives
WO2004017964A1 (en) 2002-08-19 2004-03-04 Pfizer Products Inc. Combination therapy for hyperproliferative diseases
WO2007062314A2 (en) 2005-11-23 2007-05-31 Bristol-Myers Squibb Company Heterocyclic cetp inhibitors
WO2008070496A2 (en) 2006-12-01 2008-06-12 Bristol-Myers Squibb Company N- ( (3-benzyl) -2, 2- (bis-phenyl) -propan-1-amine derivatives as cetp inhibitors for the treatment of atherosclerosis and cardiovascular diseases
EP2392567A1 (en) 2005-10-21 2011-12-07 Bristol-Myers Squibb Company Benzothiazine derivatives and their use as lxr modulators
WO2014170786A1 (en) 2013-04-17 2014-10-23 Pfizer Inc. N-piperidin-3-ylbenzamide derivatives for treating cardiovascular diseases
WO2016055901A1 (en) 2014-10-08 2016-04-14 Pfizer Inc. Substituted amide compounds
CN111205288A (zh) * 2020-02-19 2020-05-29 四川大学 一种(1S,12bS)内酰胺酯化合物的合成方法
WO2020150473A2 (en) 2019-01-18 2020-07-23 Dogma Therapeutics, Inc. Pcsk9 inhibitors and methods of use thereof

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL153199B (nl) * 1971-10-25 1977-05-16 Omnium Chimique Sa Werkwijze voor de bereiding van esters van vincaminezuur, alsmede werkwijze voor de bereiding van een geneesmiddel dat een dergelijke ester bevat en gevormd geneesmiddel dat aldus is verkregen.
CH578001A5 (sv) * 1972-04-14 1976-07-30 Sandoz Ag
JPS536264U (sv) * 1976-06-30 1978-01-20
HU174502B (hu) * 1976-12-30 1980-01-28 Richter Gedeon Vegyeszet Sposob poluchenija novykh proizvodnykh oktagidro-indolo/2,3-a/-khinolizina
US4316028A (en) * 1978-11-20 1982-02-16 Sumitomo Chemical Company, Limited Process for producing eburnane derivatives
HU179292B (en) * 1978-12-01 1982-09-28 Richter Gedeon Vegyeszet Process for preparing ester derivatives of apovincaminic acid
HU180928B (en) * 1979-08-06 1983-05-30 Richter Gedeon Vegyeszet Process for preparing new brominated 15-hydroxy-e-homo-eburane derivatives
JPS5689589U (sv) * 1979-12-13 1981-07-17
JPS5693693U (sv) * 1979-12-14 1981-07-25
HU185305B (en) * 1981-08-23 1985-01-28 Richter Gedeon Vegyeszet Process for preparing vincine and apovincine
HU186891B (en) * 1981-06-12 1985-10-28 Richter Gedeon Vegyeszet Process for producing esters of apovincaminic acid
JPS59258U (ja) * 1982-06-24 1984-01-05 日本ピラ−工業株式会社 平板形電子管式表示装置
HU187140B (en) * 1982-06-30 1985-11-28 Richter Gedeon Vegyeszet Process for preparing new aburnan-oxima ethers
HU187139B (en) * 1982-06-30 1985-11-28 Richter Gedeon Vegyeszet Process for preparing new eburnan derivatives
JPS59105767U (ja) * 1983-01-06 1984-07-16 日本ピラ−工業株式会社 平板形電子管式表示装置
JPS6032240A (ja) * 1983-07-30 1985-02-19 Sony Corp 螢光表示装置

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3884927A (en) * 1972-04-14 1975-05-20 Roussel Uclaf Process for the preparation of vincamine
US4033969A (en) * 1972-06-19 1977-07-05 Agence Nationale De Valorisation De La Recherche (Anvar) Vincamine derivatives
US3987049A (en) * 1974-01-31 1976-10-19 Synthelabo Esters of dihydroapovincaminic acid
US3979395A (en) * 1974-08-09 1976-09-07 Buskine S.A. Process for the preparation of vincamine and other indole alkaloids
US4283401A (en) * 1978-07-12 1981-08-11 Richter Gedeon Vegyeszeti Gyar Rt Process for the preparation of 11-bromo-vincaminic acid ester derivatives and their use in protecting animals against cerebral hypoxy
US4315011A (en) * 1978-07-12 1982-02-09 Richter Gedeon Vegyeszeti Gyar Rt. 1-Alkyl-9-bromohexahydroindolo quinolizium salts and use thereof to increase blood flow
US4428877A (en) 1978-07-12 1984-01-31 Richter Gedeon Vegyeszeti Gyar Rt. Cis-10-bromo-E-homoeburnanes
US4382936A (en) * 1978-11-20 1983-05-10 Sumitomo Chemical Company, Limited Cerebral vasodilator eburnane derivatives
US4285950A (en) * 1979-08-13 1981-08-25 Richter Gedeon Vegyeszeti Gyar Rt 10-halo-E-homoeburnane derivatives, a process for the preparation thereof, a process for the use thereof as vasodilators, and vasodilating compositions thereof
US4399069A (en) * 1980-10-12 1983-08-16 Richter Gedeon Vegyeszeti Gyar Rt. Process for an enantioselective synthesis of optically active 14-oxo-E-homo-eburnane derivatives
US4464535A (en) * 1981-03-11 1984-08-07 Richter Gedeon Vegyeszeti Gyar Rt. Process for the preparation of eburnamonine derivatives
US4464534A (en) * 1981-09-30 1984-08-07 Richter Gedeon Vegyeszeti Gyar Rt. Process for the preparation of vincaminic acid esters
US4614824A (en) * 1982-06-30 1986-09-30 Richter Gedeon Vegyeszeti Gyar R.T. Novel apovincaminic acid derivatives
WO2004017964A1 (en) 2002-08-19 2004-03-04 Pfizer Products Inc. Combination therapy for hyperproliferative diseases
EP2392567A1 (en) 2005-10-21 2011-12-07 Bristol-Myers Squibb Company Benzothiazine derivatives and their use as lxr modulators
WO2007062314A2 (en) 2005-11-23 2007-05-31 Bristol-Myers Squibb Company Heterocyclic cetp inhibitors
WO2008070496A2 (en) 2006-12-01 2008-06-12 Bristol-Myers Squibb Company N- ( (3-benzyl) -2, 2- (bis-phenyl) -propan-1-amine derivatives as cetp inhibitors for the treatment of atherosclerosis and cardiovascular diseases
WO2014170786A1 (en) 2013-04-17 2014-10-23 Pfizer Inc. N-piperidin-3-ylbenzamide derivatives for treating cardiovascular diseases
WO2016055901A1 (en) 2014-10-08 2016-04-14 Pfizer Inc. Substituted amide compounds
WO2020150473A2 (en) 2019-01-18 2020-07-23 Dogma Therapeutics, Inc. Pcsk9 inhibitors and methods of use thereof
CN111205288A (zh) * 2020-02-19 2020-05-29 四川大学 一种(1S,12bS)内酰胺酯化合物的合成方法
CN111205288B (zh) * 2020-02-19 2021-03-30 四川大学 一种(1S,12bS)内酰胺酯化合物的合成方法

Also Published As

Publication number Publication date
GB1351261A (en) 1974-04-24
JPS5163198A (sv) 1976-06-01
GB1351263A (en) 1974-04-24
NL7104275A (sv) 1971-10-04
BE765006A (fr) 1971-09-30
DE2115718C3 (de) 1979-07-19
AT309699B (de) 1973-07-15
DE2167044C2 (de) 1983-07-14
IT8048032A0 (it) 1980-02-28
IL36474A0 (en) 1971-05-26
SU505365A3 (ru) 1976-02-28
GB1351262A (en) 1974-04-24
DE2167043A1 (de) 1977-10-13
DK149345B (da) 1986-05-12
DE2115718B2 (de) 1978-11-02
NL158497B (nl) 1978-11-15
HU163769B (sv) 1973-10-27
SE390414B (sv) 1976-12-20
JPS5163197A (sv) 1976-06-01
CA937570A (en) 1973-11-27
SE386179B (sv) 1976-08-02
DK149345C (da) 1986-10-13
DE2115718A1 (de) 1971-10-14
IL36474A (en) 1975-08-31
PL83152B1 (en) 1975-12-31
JPS5227160B2 (sv) 1977-07-19
JPS5144960B1 (sv) 1976-12-01
DE2167044A1 (de) 1977-11-10
JPS5337360B2 (sv) 1978-10-07
CH546777A (fr) 1974-03-15

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