GB1311580A - 4-substituted phenyl cyclohexylamines and the preparation thereof - Google Patents
4-substituted phenyl cyclohexylamines and the preparation thereofInfo
- Publication number
- GB1311580A GB1311580A GB3451371A GB3451371A GB1311580A GB 1311580 A GB1311580 A GB 1311580A GB 3451371 A GB3451371 A GB 3451371A GB 3451371 A GB3451371 A GB 3451371A GB 1311580 A GB1311580 A GB 1311580A
- Authority
- GB
- United Kingdom
- Prior art keywords
- substituted phenyl
- alkyl
- followed
- trans
- cis
- 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
Links
- -1 4-substituted phenyl cyclohexylamines Chemical class 0.000 title abstract 12
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000006196 aroyl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- BXBJZYXQHHPVGO-UHFFFAOYSA-N 4-hydroxycyclohexan-1-one Chemical class OC1CCC(=O)CC1 BXBJZYXQHHPVGO-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000012024 dehydrating agents Substances 0.000 abstract 1
- 230000000994 depressogenic effect Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical class Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 abstract 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- 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
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy 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
- C07C45/65—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- C07C45/66—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/683—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6857370A | 1970-08-31 | 1970-08-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1311580A true GB1311580A (en) | 1973-03-28 |
Family
ID=22083413
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3451371A Expired GB1311580A (en) | 1970-08-31 | 1971-07-22 | 4-substituted phenyl cyclohexylamines and the preparation thereof |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE772010A (cg-RX-API-DMAC10.html) |
| CH (1) | CH555318A (cg-RX-API-DMAC10.html) |
| DE (1) | DE2139239A1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2103647B1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1311580A (cg-RX-API-DMAC10.html) |
| NL (1) | NL7111810A (cg-RX-API-DMAC10.html) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4537698A (en) * | 1982-05-28 | 1985-08-27 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Liquid crystalline piperidine derivatives |
| GB2195999A (en) * | 1986-09-10 | 1988-04-20 | Ici Plc | Tertiary amine compounds |
| US4975445A (en) * | 1989-12-06 | 1990-12-04 | Warner-Lambert Company | Substituted cyclohexenes as central nervous system agents |
| WO2003037879A1 (de) * | 2001-10-29 | 2003-05-08 | Grünenthal GmbH | Substituierte 1h-chinoxalin-2-on-verbindungen und substituierte 4-aryl- und 4-heteroarylcyclohexan-verbindungen |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3960961A (en) * | 1970-08-31 | 1976-06-01 | The Upjohn Company | 4'-Fluoro-4-{[4-(phenyl)cyclohexyl]amino}butyrophenones and the salts thereof |
-
1971
- 1971-07-22 GB GB3451371A patent/GB1311580A/en not_active Expired
- 1971-08-05 DE DE19712139239 patent/DE2139239A1/de active Pending
- 1971-08-16 CH CH1201771A patent/CH555318A/xx not_active IP Right Cessation
- 1971-08-27 NL NL7111810A patent/NL7111810A/xx unknown
- 1971-08-30 FR FR7131382A patent/FR2103647B1/fr not_active Expired
- 1971-08-31 BE BE772010A patent/BE772010A/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4537698A (en) * | 1982-05-28 | 1985-08-27 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Liquid crystalline piperidine derivatives |
| GB2195999A (en) * | 1986-09-10 | 1988-04-20 | Ici Plc | Tertiary amine compounds |
| US4975445A (en) * | 1989-12-06 | 1990-12-04 | Warner-Lambert Company | Substituted cyclohexenes as central nervous system agents |
| WO2003037879A1 (de) * | 2001-10-29 | 2003-05-08 | Grünenthal GmbH | Substituierte 1h-chinoxalin-2-on-verbindungen und substituierte 4-aryl- und 4-heteroarylcyclohexan-verbindungen |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2139239A1 (de) | 1972-03-02 |
| NL7111810A (cg-RX-API-DMAC10.html) | 1972-03-02 |
| FR2103647B1 (cg-RX-API-DMAC10.html) | 1975-02-07 |
| BE772010A (fr) | 1972-02-29 |
| FR2103647A1 (cg-RX-API-DMAC10.html) | 1972-04-14 |
| CH555318A (de) | 1974-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |