GB948583A - Novel octahydrophenanthroic acids and a process for the manufacture thereof - Google Patents

Novel octahydrophenanthroic acids and a process for the manufacture thereof

Info

Publication number
GB948583A
GB948583A GB18412/62A GB1841262A GB948583A GB 948583 A GB948583 A GB 948583A GB 18412/62 A GB18412/62 A GB 18412/62A GB 1841262 A GB1841262 A GB 1841262A GB 948583 A GB948583 A GB 948583A
Authority
GB
United Kingdom
Prior art keywords
methoxy
group
acetyl
hexahydrophenanthrene
carboxylic acid
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
GB18412/62A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB948583A publication Critical patent/GB948583A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C62/30—Unsaturated compounds
    • C07C62/34—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/29—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with halogen-containing compounds which may be formed in situ
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises: (a) octahydrophenanthroic acids of the general formula: <FORM:0948583/C2/1> (wherein R represents a hydrogen atom or a methyl group); (b) the preparation thereof from 2-acetyl-7-methoxy-1, 2, 3, 4, 9, 10-hexahydrophenanthrene by hydrogenation of the 4a-10a double bond and oxidation of the acetyl group (in either order and, if desired, with intermediate protection of the oxo group during the hydrogenation when this is performed first using an alkali metal in liquid ammonia), followed, if desired, by conversion of the 2-carboxy group into a carboxymethyl group (by an Arndt-Eistert reaction followed by de-esterification, or by the classical method via the corresponding hydroxymethyl and cyanomethyl compounds), and/or conversion of the 7-methoxy group into a hydroxy group by means of an ether-cleaving agent, and/or resolution of a resulting racemate into its optical antipodes; (c) pharmaceutical compositions comprising the products in association with a compatible pharmaceutical carrier; and (d) 7-methoxy-1, 2, 3, 4, 9, 10-hexahydrophenanthrene -2- carboxylic acid. Various procedures for carrying out the processes of (b), including the resolution of racemic products, are described and exemplified, and involve the formation of, inter alia, the following compounds not covered by the general formula above: the cyclic ethylene acetal of 2-acetyl-7-methoxy-1, 2, 3, 4, 9, 10-hexahydrophenanthrene (from the parent ketone and ethylene glycol); geometrical isomers of 2-acetyl -7- methoxyl- 2, 3, 4, 4a, 9, 10, 10aoctahydrophenanthrene (from the preceding compound by reduction and hydrolysis or by reduction of the ketone; the semicarbazone of one of the isomers is described) geometrical isomers of 7-methoxy-1, 2, 3, 4, 4a, 9, 10, 10a-octahydrophenanthrene -2- carboxylic acid chloride (from the acids and thionyl chloride); diastereoisomeric 7-methoxy-1, 2, 3, 4, 4a, 9, 10, 10a-octahydrophenanthrene -2- carboxylic acid 1-menthol and 1- and d-mardelic acid esters (from the foregoing acid chlorides and the specified hydroxy compounds); geometrical isomers of 2-diazoacetyl-, 2-hydroxymethyl-, 2-mesyloxymethyl- and 2-cyanomethyl -7- methoxy-1, 2, 3, 4, 4a, 9, 10, 10a-octahydrophenanthrene (as intermediates in the side chain elongation processes outlined above). The pharmaceutical preparations, which have antigonadotropic, hypocholerolaemic and/or oestrogenic activity, may be in the form of tablets, dragees, suppositories, capsules, solutions, emulsions or suspensions. 7-Methoxy-1, 2, 3, 4, 9, 10-hexahydrophenanthrene -2- carboxylic acid may be prepared by oxidyzing the corresponding 2-acetyl compound, or by reacting 1-vinyl -1- hydroxy -6- methoxy-1, 2, 3, 4-tetrahydronaphthalene or 1-vinyl -6-methoxy-3, 4-dihydronaphthalene with a lower alkyl acrylate, treating the product with a mineral acid and hydrolysing the resulting compound with an alkali metal hydroxide.
GB18412/62A 1961-05-15 1962-05-14 Novel octahydrophenanthroic acids and a process for the manufacture thereof Expired GB948583A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US10988361A 1961-05-15 1961-05-15

Publications (1)

Publication Number Publication Date
GB948583A true GB948583A (en) 1964-02-05

Family

ID=22330080

Family Applications (1)

Application Number Title Priority Date Filing Date
GB18412/62A Expired GB948583A (en) 1961-05-15 1962-05-14 Novel octahydrophenanthroic acids and a process for the manufacture thereof

Country Status (4)

Country Link
BE (1) BE617615A (en)
ES (1) ES277296A1 (en)
FR (1) FR2248M (en)
GB (1) GB948583A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013113946A2 (en) 2012-05-04 2013-08-08 Crystal Pharma, S.A.U. Process for the preparation of optically active 3,3-diphenylpropylamines

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013113946A2 (en) 2012-05-04 2013-08-08 Crystal Pharma, S.A.U. Process for the preparation of optically active 3,3-diphenylpropylamines
WO2013113946A3 (en) * 2012-05-04 2013-09-26 Crystal Pharma, S.A.U. Process for the preparation of optically pure fesoterodine derivatives
US9422228B2 (en) 2012-05-04 2016-08-23 Crystal Pharma, S.A.U. Process for the preparation of optically pure fesoterodine derivatives

Also Published As

Publication number Publication date
BE617615A (en) 1962-11-14
FR2248M (en) 1964-01-06
ES277296A1 (en) 1962-10-16

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