IE38375B1 - Bicycloalkyl derivatives - Google Patents
Bicycloalkyl derivativesInfo
- 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
Links
Classifications
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- 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
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- 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
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- 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]
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)
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)
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 |
-
1972
- 1972-11-04 GB GB5093172A patent/GB1444717A/en not_active Expired
-
1973
- 1973-10-12 IE IE1824/73A patent/IE38375B1/en unknown
- 1973-10-23 IL IL43470A patent/IL43470A/en unknown
- 1973-10-30 SE SE7314756A patent/SE419980B/en unknown
- 1973-10-31 BE BE137315A patent/BE806808A/en not_active IP Right Cessation
- 1973-10-31 FR FR7338821A patent/FR2205324B1/fr not_active Expired
- 1973-11-01 NL NLAANVRAGE7315031,A patent/NL182143C/en not_active IP Right Cessation
- 1973-11-02 DE DE2354931A patent/DE2354931C2/en not_active Expired
- 1973-11-02 CH CH1542273A patent/CH588440A5/xx not_active IP Right Cessation
- 1973-11-02 DK DK593573AA patent/DK142111B/en not_active IP Right Cessation
- 1973-11-02 JP JP48123891A patent/JPS5747664B2/ja not_active Expired
-
1982
- 1982-02-05 JP JP57018087A patent/JPS5936973B2/en not_active Expired
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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