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ES400149A1 - A procedure for the preparation of the derivatives of hexahidroindane and decahydro-naftaalene. (Machine-translation by Google Translate, not legally binding) - Google Patents

A procedure for the preparation of the derivatives of hexahidroindane and decahydro-naftaalene. (Machine-translation by Google Translate, not legally binding)

Info

Publication number
ES400149A1
ES400149A1 ES400149A ES400149A ES400149A1 ES 400149 A1 ES400149 A1 ES 400149A1 ES 400149 A ES400149 A ES 400149A ES 400149 A ES400149 A ES 400149A ES 400149 A1 ES400149 A1 ES 400149A1
Authority
ES
Spain
Prior art keywords
methyl
formula
alkyl
steroids
hydrogen
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
ES400149A
Other languages
Spanish (es)
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
Priority claimed from US765023A external-priority patent/US3897460A/en
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of ES400149A1 publication Critical patent/ES400149A1/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C61/12—Saturated polycyclic compounds
    • C07C61/125—Saturated polycyclic compounds having a carboxyl group bound to a condensed ring system
    • C07C61/13—Saturated polycyclic compounds having a carboxyl group bound to a condensed ring system having two rings
    • 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
    • C07C62/18—Saturated compounds containing keto groups
    • C07C62/26—Saturated compounds containing keto groups containing singly bound oxygen-containing groups
    • 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
    • C07C62/38—Unsaturated compounds containing keto groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/26—Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • 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
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/16—Benz[e]indenes; Hydrogenated benz[e]indenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Novel tricyclic ketones of the formula in which m is 1 or 2, B represents carboxy, C 1-7 -alkoxycarbonyl, aryloxycarbonyl, cyano, C 1-7 alkylsulphinyl or C 1-7 alkylsulphonyl, Z represents carbonyl, C 1-6 alkylenedioxymethylene or a group >CHOR 2 (where R 2 is hydrogen, C 1-7 alkyl, C 1-7 alkoxy-C 1-7 alkyl, phenyl- C 1-7 alkyl, tetrahydropyranyl, C 1-6 alkanoyl, benzoyl, nitrobenzoyl, barboxy-C 1-6 alkanoyl, carboxybenzoyl, trifluoromethyl or camphor sulphonyl), R 4 is hydrogen or C 1-7 alkyl and R 1 is hydrogen, C 1-7 - alkyl or a group of the formulae (where R 7 is C 1-7 alkyl, R 15 is an oxo, C 1-6 alkylenedioxy or arylendioxy group or represent hydrogen and a C 1-7 alkoxy group, R 25 and R 26 are hydrogen, hydroxy or C 1-7 alkyl, R1 is hydrogen or C 1-7 alkyl and R11 is hydrogen, C 1-7 alkyl, C 1-7 alkylaryl or aralkyl) and the alkali metal salts of the free acids, are prepared by treating a compound of the formula in an inert organic solvent with a dilute solution of an alkali metal or alkaline earth metal hydroxide to effect cyclization and, if required acidifying a product in which B is the salt of a carboxy group to the free acid or esterifying a product in which B is a carboxy group. Examples describe the preparation of the 6-methyl-, 6 - [2 - (2 - methyl - 1,3 - dioxolan - 2 - yl)ethyl]-, 6 - [(3,5 - dimethyl - isoxazol - 4 - yl)methyl]-, 6 - (3,3 - phenylenedioxybutyl) - derivatives of 3# - t butoxy - 2,3,3a,4,5,7,8,9,9a#,9b[alpha]- decahydro - 3a#- methyl - 7 - oxo - 1H- benz[e]- inden - 8[alpha] - carboxylic acid and the methyl ester thereof. Steroids.-The novel ketones are used in the preparation of steroids. Thus, ketals of the formula where W is an alkylene or arylene radical, can be decarboxylated by heating to ketals of the formula catalytically hydrogenated to and cyclized to the steroids of the formula Examples 2 and 4 describe the preparation of racemic 19-nortestosterone by this route, and it is also stated that a product wherein R 4 is Et, may then be oxidized and ethynylated to yield optically active norgestrel. Also, ketones of the formula can be decarboxylated by,heating to compounds and cyclized using an alkali alkoxide to diene steroids of the formula or the ketones of the formula Ib can be treated with a base to obtain acids of the formula which on heating with cone. mineral acid yield hydroxy diene steroids of the formula which can also be obtained from the steroids VII by refluxing in methanol/HCl. Further, ketones of the Formula I in which R 1 is an isoxazolylmethyl group can be decarboxylated to the compounds Ic and subsequently converted to 19-norsteroids as shown below In Example 3 a compound of Formula X wherein Z is carbpnyl is converted to its bis-(ethylene) ketal which is then hydrogenated to yield a "vinylogous amide" of unspecified structure. The latter is refluxed with aqueous KOH and the resulting 3,37,7 - bis - (ethylenedioxy)- 3a# - methyl - 6 - (3 - oxobutyl) - perhydro - 1H- benz[e]indene is cyclized with aqueous HCl to yield estr-4-ene-3,17-dione. In the preparation of steroids, the 6 - methyl - 6 - [2 - (2 methyl - 1,3- dioxolan - 2 - yl)ethyl]-, and 6 - [(3,5 - dimeihylisoxazol - 4 - yl)methyl] and 6 - (3,3 - diphenylenedioxyliutyl) - derivatives of 3# - t - butoxy- 2,3,3a,4,5,7,8,9,9a#,9b# - dehydro - 3a# - methyl- 1H - benz[e]inden - 7 - one, and the corresponding dodecahydro compounds, 6 - [3,5 - dimethyl - 4- isoxazolyl)methyl] - 3a# - methyl - 3# - hydroxy- 1,2,3,3a,4,5,8,9,9a#,9b[alpha] - decahydro - 7H- benz[e]inden - 7 - one, 6 - [(3,5 - dimethyl - -.4- isoxazolyl)methyl] - 3a# - methyl - 1,2,3,3a,4,5,9, 9a#,9b[alpha] - octahydro - 3H benz[e]inden - 3,7(8H)- dione, and the corresponding 2H,6H saturated dione and its di-ethylene ketal, and 3,3,7,7-bis- (ethylenedioxy) - 3a# - methyl - 6 - (3 - oxobutyl)- perhydro - 1H - benz[e]indene are obtained.
ES400149A 1968-10-04 1972-02-25 A procedure for the preparation of the derivatives of hexahidroindane and decahydro-naftaalene. (Machine-translation by Google Translate, not legally binding) Expired ES400149A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US765023A US3897460A (en) 1968-10-04 1968-10-04 3{62 -Tertiarybutoxy-decahydro-benz{8 E{9 indenes
US84554669A 1969-07-28 1969-07-28

Publications (1)

Publication Number Publication Date
ES400149A1 true ES400149A1 (en) 1975-03-16

Family

ID=27117546

Family Applications (2)

Application Number Title Priority Date Filing Date
ES372175A Expired ES372175A1 (en) 1968-10-04 1969-10-03 A procedure for the preparation of triciclic compounds. (Machine-translation by Google Translate, not legally binding)
ES400149A Expired ES400149A1 (en) 1968-10-04 1972-02-25 A procedure for the preparation of the derivatives of hexahidroindane and decahydro-naftaalene. (Machine-translation by Google Translate, not legally binding)

Family Applications Before (1)

Application Number Title Priority Date Filing Date
ES372175A Expired ES372175A1 (en) 1968-10-04 1969-10-03 A procedure for the preparation of triciclic compounds. (Machine-translation by Google Translate, not legally binding)

Country Status (12)

Country Link
JP (1) JPS5636177B1 (en)
AT (2) AT300209B (en)
BE (1) BE739791A (en)
CA (1) CA977351A (en)
CH (4) CH576997A5 (en)
DE (1) DE1950012C2 (en)
DK (1) DK140588B (en)
ES (2) ES372175A1 (en)
FR (1) FR2019929A1 (en)
GB (5) GB1265514A (en)
NL (1) NL168225C (en)
SE (5) SE375304B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2165320C2 (en) * 1971-12-24 1982-09-16 Schering Ag, 1000 Berlin Und 4619 Bergkamen Process for the preparation of bicycloalkanethio derivatives
DE2449031C2 (en) * 1974-10-11 1983-08-04 Schering Ag, 1000 Berlin Und 4619 Bergkamen Process for the preparation of 13β-alkyl-4-gonen-3,17-dione

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1364556A (en) * 1962-03-06 1964-06-26 Roussel Uclaf New process for the synthesis of steroids and related compounds and products used in this process

Also Published As

Publication number Publication date
GB1265516A (en) 1972-03-01
DK140588C (en) 1980-03-17
NL6914990A (en) 1970-04-07
CA977351A (en) 1975-11-04
DK140588B (en) 1979-10-08
AT300209B (en) 1972-07-25
SE385292B (en) 1976-06-21
FR2019929A1 (en) 1970-07-10
SE381876B (en) 1975-12-22
DE1950012C2 (en) 1982-05-19
ES372175A1 (en) 1972-02-16
CH572943A5 (en) 1976-02-27
SE403910B (en) 1978-09-11
JPS5636177B1 (en) 1981-08-22
SE385293B (en) 1976-06-21
CH582123A5 (en) 1976-11-30
GB1265514A (en) 1972-03-01
AT311569B (en) 1973-11-26
CH565130A5 (en) 1975-08-15
GB1265512A (en) 1972-03-01
CH576997A5 (en) 1976-06-30
NL168225B (en) 1981-10-16
GB1265515A (en) 1972-03-01
NL168225C (en) 1982-03-16
BE739791A (en) 1970-04-03
SE375304B (en) 1975-04-14
GB1265513A (en) 1972-03-01
DE1950012A1 (en) 1970-04-09

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