GB897988A - Aza-yohimbane compounds - Google Patents

Aza-yohimbane compounds

Info

Publication number
GB897988A
GB897988A GB283960A GB283960A GB897988A GB 897988 A GB897988 A GB 897988A GB 283960 A GB283960 A GB 283960A GB 283960 A GB283960 A GB 283960A GB 897988 A GB897988 A GB 897988A
Authority
GB
United Kingdom
Prior art keywords
aza
methoxy
methoxycarbonyl
acyloxy
yohimbane
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
GB283960A
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.)
Laboratoires Francais de Chimiotherapie SA
Original Assignee
Laboratoires Francais de Chimiotherapie 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 Laboratoires Francais de Chimiotherapie SA filed Critical Laboratoires Francais de Chimiotherapie SA
Publication of GB897988A publication Critical patent/GB897988A/en
Expired 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
    • C07D471/02—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 two hetero rings
    • C07D471/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

The invention comprises 18b -hydroxy-17a -methoxy - 16b - methoxycarbonyl - 12 - aza - 3b ,20a -yohimbane, its 18b -acyloxy derivatives, particularly the laevorotatory 18b -31,41,51-trimethoxy benzoate, their 3a -epimers, and the corresponding D 3(14)-20a -yohimbenes, together with a process for the preparation of laevorotatory 18b - (31, 41, 51 - trimethoxy - benzoyl - oxy) - 17a - methoxy - 16b - methoxycarbonyl - 12 - aza - 3b , 20a - yohimbane by quaternizing 7-aza gramine, reacting the salt produced with cyanide ions, reducing the resulting 7-aza-indolyl-3-acetonitrile, preferably by hydrogenation over Raney nickel, to 7-aza-tryptamine, condensing this with dextrorotatory (pyridine) 1b -carboxymethyl - 2b - methoxy - carbonyl - 3a - methoxy - 4b - acyloxy - 6b - formyl cyclohexane, reducing the resulting 18b - acyloxy - 17a - methoxy - 16b - methoxycarbonyl - 2, 3 - 3, 4 - diseco - D 4(21)-12-aza-20a -yohimben-3-oic acid, e.g. with a metal hydride, to an 18b -acyloxy-17a -methoxy-16b -methoxycarbonyl - 2, 3 - 3, 4 - diseco - 12 - aza - 20a -yohimban-3-oic acid, cyclising it by dehydration to an 18b -acyloxy-17a -methoxy-16b -methoxycarbonyl - 3 - oxo - 2, 3 - seco - 12 - az - 20a - yohimbane, and further cyclising, preferably with phosphorus oxychloride to an 18b -acyloxy-17a - methoxy - 16b - methoxycarbonyl - D 3(14)-12-aza-20a -yohimbene, reducing this compound, e.g. with zinc and perchloric acid, to an 18b -acyloxy - 17a - methoxy - 16b - methoxycarbonyl - 12 - aza - 3b , 20a - yohimbane, partially saponifying the latter to the 18b -hydroxy compound and then re-esterifying with a 3,4,5-trimethoxybenzoylating agent, e.g. the anhydride or acid chloride. Detailed examples illustrate the invention. Specification 868,479 is referred to.
GB283960A 1959-02-04 1960-01-26 Aza-yohimbane compounds Expired GB897988A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR785766A FR1261179A (en) 1959-02-04 1959-02-04 12-aza deserpidine and its preparation process

Publications (1)

Publication Number Publication Date
GB897988A true GB897988A (en) 1962-06-06

Family

ID=8710828

Family Applications (1)

Application Number Title Priority Date Filing Date
GB283960A Expired GB897988A (en) 1959-02-04 1960-01-26 Aza-yohimbane compounds

Country Status (3)

Country Link
CH (1) CH392541A (en)
FR (1) FR1261179A (en)
GB (1) GB897988A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AR205790A1 (en) * 1972-05-01 1976-06-07 American Home Prod PROCESS FOR THE PREPARATION OF 2,3,5,6,11,11B-HEXAHYDRO-1H-PIRIDO (3 ', 2': 4,5) PIRROLO (3,2-G) INDOLICINA-4-OXIDOS
FR2687402B1 (en) * 1992-02-14 1995-06-30 Lipha NOVEL AZAINDOLES, METHODS OF PREPARATION AND MEDICAMENTS CONTAINING THEM.

Also Published As

Publication number Publication date
CH392541A (en) 1965-05-31
FR1261179A (en) 1961-05-19

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