IE38375L - Bicyclooctane derivatives - Google Patents
Bicyclooctane derivativesInfo
- Publication number
- IE38375L IE38375L IE731824A IE182473A IE38375L IE 38375 L IE38375 L IE 38375L IE 731824 A IE731824 A IE 731824A IE 182473 A IE182473 A IE 182473A IE 38375 L IE38375 L IE 38375L
- Authority
- IE
- Ireland
- Prior art keywords
- oct
- trans
- alkyl
- acid
- compounds
- Prior art date
Links
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical class C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 150000001408 amides Chemical class 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- -1 2-phenylbicyclo- [2,2,2]oct-3-yl group Chemical group 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 1
- 150000001242 acetic acid derivatives Chemical class 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000001539 anorectic effect Effects 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 238000007796 conventional method Methods 0.000 abstract 1
- 206010061428 decreased appetite Diseases 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- IMKVSWPEZCELRM-UHFFFAOYSA-N ethyl p-methylcinnamate Natural products CCOC(=O)C=CC1=CC=C(C)C=C1 IMKVSWPEZCELRM-UHFFFAOYSA-N 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical class CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229940066769 systemic antihistamines substituted alkylamines Drugs 0.000 abstract 1
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]
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 true IE38375L (en) | 1974-05-04 |
| IE38375B1 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 DK DK593573AA patent/DK142111B/en not_active IP Right Cessation
- 1973-11-02 DE DE2354931A patent/DE2354931C2/en not_active Expired
- 1973-11-02 JP JP48123891A patent/JPS5747664B2/ja not_active Expired
- 1973-11-02 CH CH1542273A patent/CH588440A5/xx not_active IP Right Cessation
-
1982
- 1982-02-05 JP JP57018087A patent/JPS5936973B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7315031A (en) | 1974-05-07 |
| DE2354931A1 (en) | 1974-05-09 |
| FR2205324B1 (en) | 1976-05-14 |
| CH588440A5 (en) | 1977-05-31 |
| DK142111C (en) | 1981-02-02 |
| JPS5747664B2 (en) | 1982-10-12 |
| JPS57171941A (en) | 1982-10-22 |
| JPS49132058A (en) | 1974-12-18 |
| DE2354931C2 (en) | 1983-12-08 |
| SE419980B (en) | 1981-09-07 |
| JPS5936973B2 (en) | 1984-09-06 |
| NL182143B (en) | 1987-08-17 |
| DK142111B (en) | 1980-09-01 |
| IL43470A0 (en) | 1974-01-14 |
| GB1444717A (en) | 1976-08-04 |
| BE806808A (en) | 1974-04-30 |
| IE38375B1 (en) | 1978-03-01 |
| NL182143C (en) | 1988-01-18 |
| IL43470A (en) | 1976-08-31 |
| FR2205324A1 (en) | 1974-05-31 |
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