GB1265514A - - Google Patents

Info

Publication number
GB1265514A
GB1265514A GB1265514DA GB1265514A GB 1265514 A GB1265514 A GB 1265514A GB 1265514D A GB1265514D A GB 1265514DA GB 1265514 A GB1265514 A GB 1265514A
Authority
GB
United Kingdom
Prior art keywords
alkyl
group
coch
hydrogen
aryl
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
Inventor
Z G Hajos
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 GB1265514A publication Critical patent/GB1265514A/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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)

Abstract

1,265,514. #-Substituted ketones. F. HOFFMANN-LA ROCHE & CO. A.G. 2 Oct., 1969 [4 Oct., 1968; 28 July, 1969], No. 45274/70. Divided out of 1,265,512. Heading C2C. Novel ketones of the formula in which B represents a C 1-7 alkoxy-carbonyl, aryloxy-carbonyl, C 1-7 alkylsulphinyl or C 1-7 alkylsulphonyl radical and R 1 is a group of the formulae where R, is a C 1-7 alkyl group, R 15 is an oxo group, a C 1-8 alkylenedioxy or an arylenedioxy group or represent hydrogen and a C 1-7 alkoxy group, R 25 and R 26 are hydrogen, hydroxy or C 1 _ 7 alkyl groups, R<SP>1</SP> is hydrogen or C 1-7 alkyl arid R<SP>11</SP> is hydrogen, C 1-7 alkyl, C 1-7 alkyl-aryl or an aralkyl group, are prepared by reacting an ester R 1 CH 2 CO.OR<SP>1</SP> 3 , where R<SP>1</SP> 3 is C 1-7 alkyl, cyclopentyl, cyclohexyl or aryl, either with a base, e.g. LiOH, to form the salt of the acid by saponification and reacting the salt with an organo-metallic compound such as methyl lithium to obtain a ketone R 1 CH 2 COCH 3 , or reacting the ester with C 1-7 alkylsulphinylmethylene compound to obtain a sulphoxide R 1 CH 2 COCH 2 SO alkyl and reducing the sulphoxide, e.g. with Al amalgam, to obtain the above ketone R 1 CH 2 COCH 3 , and condensing the ketone with a carbonate CO(0R 5 ) 2 to obtain the esters R 1 CH 2 COCH 2 CO 2 R 5 where R 5 is C 1-7 alkyl or aryl. The sulphoxide obtained above can be oxidized, e.g. with permanganate, to obtain the required sulphone. Examples describe the preparation of 6-(2-methyl-1,3- dioxolan-2-yl) - 3 - oxo - hexanoic acid ethyl ester, 1 - methylsulphinyl - 5(2 - methyl - 1,3- dioxolan - 2 - yl) - 2 - pentanone, ethyl 5- (3,5 - dimethylisoxazole - 4 - yl) - 3 - oxopentanoate and ethyl 3-oxo-7,7-o-phenylenedioxy octanoate.
GB1265514D 1968-10-04 1969-10-02 Expired GB1265514A (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
GB1265514A true GB1265514A (en) 1972-03-01

Family

ID=27117546

Family Applications (5)

Application Number Title Priority Date Filing Date
GB1265516D Expired GB1265516A (en) 1968-10-04 1969-10-02
GB1265513D Expired GB1265513A (en) 1968-10-04 1969-10-02
GB1265515D Expired GB1265515A (en) 1968-10-04 1969-10-02
GB1265514D Expired GB1265514A (en) 1968-10-04 1969-10-02
GB1265512D Expired GB1265512A (en) 1968-10-04 1969-10-02

Family Applications Before (3)

Application Number Title Priority Date Filing Date
GB1265516D Expired GB1265516A (en) 1968-10-04 1969-10-02
GB1265513D Expired GB1265513A (en) 1968-10-04 1969-10-02
GB1265515D Expired GB1265515A (en) 1968-10-04 1969-10-02

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB1265512D Expired GB1265512A (en) 1968-10-04 1969-10-02

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) GB1265516A (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
CH582123A5 (en) 1976-11-30
CH572943A5 (en) 1976-02-27
DK140588C (en) 1980-03-17
SE375304B (en) 1975-04-14
NL6914990A (en) 1970-04-07
ES372175A1 (en) 1972-02-16
AT311569B (en) 1973-11-26
JPS5636177B1 (en) 1981-08-22
FR2019929A1 (en) 1970-07-10
NL168225C (en) 1982-03-16
AT300209B (en) 1972-07-25
DE1950012C2 (en) 1982-05-19
DE1950012A1 (en) 1970-04-09
CH576997A5 (en) 1976-06-30
CH565130A5 (en) 1975-08-15
NL168225B (en) 1981-10-16
GB1265516A (en) 1972-03-01
SE385292B (en) 1976-06-21
CA977351A (en) 1975-11-04
DK140588B (en) 1979-10-08
SE403910B (en) 1978-09-11
SE381876B (en) 1975-12-22
GB1265512A (en) 1972-03-01
BE739791A (en) 1970-04-03
ES400149A1 (en) 1975-03-16
GB1265515A (en) 1972-03-01
SE385293B (en) 1976-06-21
GB1265513A (en) 1972-03-01

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee