IE38375B1 - Bicycloalkyl derivatives - Google Patents

Bicycloalkyl derivatives

Info

Publication number
IE38375B1
IE38375B1 IE1824/73A IE182473A IE38375B1 IE 38375 B1 IE38375 B1 IE 38375B1 IE 1824/73 A IE1824/73 A IE 1824/73A IE 182473 A IE182473 A IE 182473A IE 38375 B1 IE38375 B1 IE 38375B1
Authority
IE
Ireland
Prior art keywords
oct
trans
alkyl
acid
compounds
Prior art date
Application number
IE1824/73A
Other versions
IE38375L (en
Original Assignee
Lilly Industries Ltd
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 Lilly Industries Ltd filed Critical Lilly Industries Ltd
Publication of IE38375L publication Critical patent/IE38375L/en
Publication of IE38375B1 publication Critical patent/IE38375B1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/44—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by —CHO groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C247/00—Compounds containing azido groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/235—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
    • C07C47/453—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
    • C07C47/457—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/132—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Neurosurgery (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Biomedical Technology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

1444717 2 - Phenyblicyclo[2,2,2]octane derivatives LILLY INDUSTRIES Ltd 22 Oct 1973 [4 Nov 1972] 50931/72 Heading C2C Novel compounds of the Formula (I) and acid addition salts thereof, wherein n is an integer from 1 to 3, R 1 is C 1-4 alkyl, R 2 is H or C 1-4 alkyl and R is a trans 2-phenylbicyclo- [2,2,2]oct-3-yl group of the Formula (II) wherein R 4 and R 5 are the same or different and may be H, halo, NO 2 , -NH 2 , C 2-5 acylamino, mono- or di-C 1-4 alkylamino, C 1-4 alkyl or C 1-4 alkoxy may be obtained by conventional methods for preparing substituted alkyl amines preferably from an intermediate of the Formula (III) R-(CH 2 ) m -R 3 wherein R is as defined above, m is 0, 1 or 2 and R 3 denotes -CHO, -CN, -CONR 6 R 7 , where R 6 and R 7 are independently C 1-4 alkyl, -CH 2 NCO or -COOR 8 , where R 8 is C 1-4 alkyl. Also novel are amines of the formula or an acid addition salt thereof, where R and n are as above, provided that when n is 1, R cannot be a trans-2-(p-chlorophenyl)-bicyclo- [2,2,2]oct-3-yl group. Examples describe the following intermediates: (1) traps-6-phenylbicyclo[2,2,2]oct-2-ene- 5-carboxaldehyde is hydrogenated to (III) where R 3 =CHO, R 4 and R 5 =H, m=0; in similar compounds, R 4 =H, R 5 =p-CH 3 -, p-Cl-, p-NH 2 , p-Br, or R 4 and R 5 =CH 3 ; (2) the product of (1) is reacted with malonic acid to give III where R 3 is -CH=CH-COOH and this is hydrogenated to III where R 3 = -COOH, m = 2; and the latter is converted to its amide; (3) the substituted proprionic acid is reacted with NaN 3 in ethyl chloroformate to form III where m = 1, R 3 = -CH 2 NCO; similar substituted compounds are formed; (4) product of (1) is oxidized to corresponding 3-carboxylic acid and converted to amides; (5) the 3-carboxylic acid is converted to the acid chloride and reacted with CH 2 N 2 and AgO forming R-substituted acetic acid, and its amide and R- acetonitrile; (6) trans-p-methylcinnamic acid, ethyl ester, and cyclohexadiene reacted forming ethyl trans-6-methylphenylbicyclo[2,2,2]oct-2- ene-5-carboxylate which is reduced forming -corresponding-octane carboxylate; corresponding p-H, Cl, CH 3 O, NMe 2 , NH 2 and NO 2 compounds are formed; (7) trans-3,4-dichloroeinnamonitrile and cyclohexadiene and heated to form 5-cyano-6-(3<SP>1</SP>,4<SP>1</SP>-dichlorophenyl)bicyclo- [2,2,2]oct-2-ene which is hydrogenated to corresponding octane compound; other substituted compounds are described; (8) product of (1) is nitrated to p-nitro compound; similar nitration of trans-6-phenylbicyclo[2,2,2]oct-2-ene-5-carboxaldehyde yields the p-nitro compound which is reduced to trans - 2 - p - aminophenylbicyclo- [2,2,2]octane-3-carboxaldehyde. Pharmaceutical compositions having central nervous system and/or anorectic and/or analgesic activity comprise compounds of Formula (I) above or a pharmaceutically acceptable acid addition salt thereof in association with a pharmaceutical carrier, in forms suitable for administration orally or by injection. [GB1444717A]
IE1824/73A 1972-11-04 1973-10-12 Bicycloalkyl derivatives IE38375B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5093172A GB1444717A (en) 1972-11-04 1972-11-04 Bicycloalkyl derivatives

Publications (2)

Publication Number Publication Date
IE38375L IE38375L (en) 1974-05-04
IE38375B1 true IE38375B1 (en) 1978-03-01

Family

ID=10457988

Family Applications (1)

Application Number Title Priority Date Filing Date
IE1824/73A IE38375B1 (en) 1972-11-04 1973-10-12 Bicycloalkyl derivatives

Country Status (11)

Country Link
JP (2) JPS5747664B2 (en)
BE (1) BE806808A (en)
CH (1) CH588440A5 (en)
DE (1) DE2354931C2 (en)
DK (1) DK142111B (en)
FR (1) FR2205324B1 (en)
GB (1) GB1444717A (en)
IE (1) IE38375B1 (en)
IL (1) IL43470A (en)
NL (1) NL182143C (en)
SE (1) SE419980B (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1549174A (en) * 1975-05-08 1979-08-01 Lilly Industries Ltd Amine derivatives
GB1551035A (en) * 1975-07-24 1979-08-22 Lilly Industries Ltd Derivatives of bicyclo (2,2,2)oct-3-ylmethylamine
US4215074A (en) * 1978-07-15 1980-07-29 Lilly Industries Limited Process for preparing cis-bicyclooctylamines
GB2367554A (en) * 2000-10-04 2002-04-10 Lilly Co Eli Pharmacologically active amines

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1468808A1 (en) * 1965-04-21 1969-04-17 Du Pont Process for the preparation of substituted phenylbicyclo- (2,2,2) -octanes

Also Published As

Publication number Publication date
DE2354931A1 (en) 1974-05-09
JPS49132058A (en) 1974-12-18
BE806808A (en) 1974-04-30
IE38375L (en) 1974-05-04
NL182143C (en) 1988-01-18
FR2205324B1 (en) 1976-05-14
DE2354931C2 (en) 1983-12-08
NL7315031A (en) 1974-05-07
FR2205324A1 (en) 1974-05-31
IL43470A0 (en) 1974-01-14
DK142111B (en) 1980-09-01
NL182143B (en) 1987-08-17
DK142111C (en) 1981-02-02
JPS5747664B2 (en) 1982-10-12
IL43470A (en) 1976-08-31
SE419980B (en) 1981-09-07
GB1444717A (en) 1976-08-04
JPS57171941A (en) 1982-10-22
CH588440A5 (en) 1977-05-31
JPS5936973B2 (en) 1984-09-06

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