FR2433528A2 - 3-Beta, 16-alpha 14,15-di:hydro-20,21-di:nor:eburnamenine-14-ol prepn. - by redn. of a toluene soln. of 3-beta, 16-alpha 20,21-di: nor:eburnamenine-14-one with sodium-aluminium di:ethyl-hydride - Google Patents

3-Beta, 16-alpha 14,15-di:hydro-20,21-di:nor:eburnamenine-14-ol prepn. - by redn. of a toluene soln. of 3-beta, 16-alpha 20,21-di: nor:eburnamenine-14-one with sodium-aluminium di:ethyl-hydride

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Publication number
FR2433528A2
FR2433528A2 FR7823850A FR7823850A FR2433528A2 FR 2433528 A2 FR2433528 A2 FR 2433528A2 FR 7823850 A FR7823850 A FR 7823850A FR 7823850 A FR7823850 A FR 7823850A FR 2433528 A2 FR2433528 A2 FR 2433528A2
Authority
FR
France
Prior art keywords
beta
alpha
eburnamenine
cerebral
prepn
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.)
Granted
Application number
FR7823850A
Other languages
French (fr)
Other versions
FR2433528B2 (en
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
Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA
Priority to FR7823850A priority Critical patent/FR2433528A2/en
Publication of FR2433528A2 publication Critical patent/FR2433528A2/en
Application granted granted Critical
Publication of FR2433528B2 publication Critical patent/FR2433528B2/fr
Granted legal-status Critical Current

Links

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
    • C07D471/22—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 systems contains four or more hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Prepn. of B isomer of (3 beta, 16 alpha) (plus-or-minus) -14, 15-dihydro-20, 21-dinoreburnamenin-14-ol (I) comprises (a) reacting a soln. of (3 beta, 16 alpha)- (plus-or-minus), 21-dinoreburnamenin-14(15H)-one hydrochloride (II) in toluene witha soln. of sodium aluminium diethylhydride in toluene at room temperature; (b) pouring the mixt. into ice/water; (c) sepg. the solid prod.; (d) re-dissolving the prod. in large vol. of CH2Cl2; (e) washing with water and (f) distilling the solvent. Used as cerebral vasodilator and oxygenator which increases cerebral microcirculation and to treat cerebral arteriosclerosis and circulatory troubles, cerebral insufficiency, cerebrovascular problems cranial traumations, cerebral and meningeal haemorrhages etc.
FR7823850A 1978-08-16 1978-08-16 3-Beta, 16-alpha 14,15-di:hydro-20,21-di:nor:eburnamenine-14-ol prepn. - by redn. of a toluene soln. of 3-beta, 16-alpha 20,21-di: nor:eburnamenine-14-one with sodium-aluminium di:ethyl-hydride Granted FR2433528A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7823850A FR2433528A2 (en) 1978-08-16 1978-08-16 3-Beta, 16-alpha 14,15-di:hydro-20,21-di:nor:eburnamenine-14-ol prepn. - by redn. of a toluene soln. of 3-beta, 16-alpha 20,21-di: nor:eburnamenine-14-one with sodium-aluminium di:ethyl-hydride

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7823850A FR2433528A2 (en) 1978-08-16 1978-08-16 3-Beta, 16-alpha 14,15-di:hydro-20,21-di:nor:eburnamenine-14-ol prepn. - by redn. of a toluene soln. of 3-beta, 16-alpha 20,21-di: nor:eburnamenine-14-one with sodium-aluminium di:ethyl-hydride

Publications (2)

Publication Number Publication Date
FR2433528A2 true FR2433528A2 (en) 1980-03-14
FR2433528B2 FR2433528B2 (en) 1981-07-24

Family

ID=9211826

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7823850A Granted FR2433528A2 (en) 1978-08-16 1978-08-16 3-Beta, 16-alpha 14,15-di:hydro-20,21-di:nor:eburnamenine-14-ol prepn. - by redn. of a toluene soln. of 3-beta, 16-alpha 20,21-di: nor:eburnamenine-14-one with sodium-aluminium di:ethyl-hydride

Country Status (1)

Country Link
FR (1) FR2433528A2 (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3322686A1 (en) * 1982-06-30 1984-02-16 Richter Gedeon Vegyészeti Gyár R.T., 1475 Budapest NEW EBURNE DERIVATIVES, METHOD FOR PRODUCING THE SAME AND PHARMACEUTICAL PREPARATIONS CONTAINING THEM
EP0317426A1 (en) * 1987-11-19 1989-05-24 Roussel-Uclaf Optically active products of derivatives of 20,21-dinoreburnamenine, process for their preparation, their use as medicines and pharmaceutical compositions containing them
US7354918B2 (en) 2004-04-14 2008-04-08 Biocortech Derivatives of 14.15-dihydro 20.21-dinoreburnamenin-14-ol and applications thereof
EP2078716A1 (en) 2008-01-04 2009-07-15 Les Laboratoires Servier New derivatives of 1H-indol-1-yl-urea, method for preparing same and pharmaceutical compositions containing them

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1586697A (en) * 1967-08-23 1970-02-27
FR2381048A1 (en) * 1977-02-22 1978-09-15 Roussel Uclaf NEW DERIVATIVES OF 20,21-DINOREBURNAMENINE, A PROCESS FOR THEIR PREPARATION AND THEIR APPLICATION AS MEDICINAL PRODUCTS

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1586697A (en) * 1967-08-23 1970-02-27
FR2381048A1 (en) * 1977-02-22 1978-09-15 Roussel Uclaf NEW DERIVATIVES OF 20,21-DINOREBURNAMENINE, A PROCESS FOR THEIR PREPARATION AND THEIR APPLICATION AS MEDICINAL PRODUCTS

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3322686A1 (en) * 1982-06-30 1984-02-16 Richter Gedeon Vegyészeti Gyár R.T., 1475 Budapest NEW EBURNE DERIVATIVES, METHOD FOR PRODUCING THE SAME AND PHARMACEUTICAL PREPARATIONS CONTAINING THEM
EP0317426A1 (en) * 1987-11-19 1989-05-24 Roussel-Uclaf Optically active products of derivatives of 20,21-dinoreburnamenine, process for their preparation, their use as medicines and pharmaceutical compositions containing them
FR2623503A1 (en) * 1987-11-19 1989-05-26 Roussel Uclaf
US7354918B2 (en) 2004-04-14 2008-04-08 Biocortech Derivatives of 14.15-dihydro 20.21-dinoreburnamenin-14-ol and applications thereof
EP2078716A1 (en) 2008-01-04 2009-07-15 Les Laboratoires Servier New derivatives of 1H-indol-1-yl-urea, method for preparing same and pharmaceutical compositions containing them

Also Published As

Publication number Publication date
FR2433528B2 (en) 1981-07-24

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