CA1051433A - 1-substituted-4-(1,2-diphenylethyl)piperazine derivatives and their salts and the preparation thereof - Google Patents
1-substituted-4-(1,2-diphenylethyl)piperazine derivatives and their salts and the preparation thereofInfo
- Publication number
- CA1051433A CA1051433A CA218,369A CA218369A CA1051433A CA 1051433 A CA1051433 A CA 1051433A CA 218369 A CA218369 A CA 218369A CA 1051433 A CA1051433 A CA 1051433A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- methoxyphenyl
- salt
- formula
- acceptable salt
- 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
- 150000003839 salts Chemical class 0.000 title claims abstract description 94
- -1 1-substituted-4-(1,2-diphenylethyl)piperazine Chemical class 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title abstract description 28
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 97
- 230000008569 process Effects 0.000 claims abstract description 88
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 24
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims abstract description 22
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 169
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 66
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 58
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 50
- 239000000126 substance Substances 0.000 claims description 29
- 239000012458 free base Substances 0.000 claims description 24
- 230000002829 reductive effect Effects 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- 238000003776 cleavage reaction Methods 0.000 claims description 10
- 230000007017 scission Effects 0.000 claims description 10
- 230000002140 halogenating effect Effects 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000005695 dehalogenation reaction Methods 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- PEUIQMITKZSCOP-UHFFFAOYSA-N 1-(2-methoxyphenyl)-4-[2-(4-methylphenyl)-1-phenylethyl]piperazine Chemical compound COC1=CC=CC=C1N1CCN(C(CC=2C=CC(C)=CC=2)C=2C=CC=CC=2)CC1 PEUIQMITKZSCOP-UHFFFAOYSA-N 0.000 claims description 3
- 235000013350 formula milk Nutrition 0.000 claims 28
- 230000000875 corresponding effect Effects 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- JNPGYEYFROXAKK-UHFFFAOYSA-N 1-cyclohexyl-4-[2-(4-methoxyphenyl)-1-phenylethyl]piperazine Chemical compound C1=CC(OC)=CC=C1CC(C=1C=CC=CC=1)N1CCN(C2CCCCC2)CC1 JNPGYEYFROXAKK-UHFFFAOYSA-N 0.000 claims 4
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
- DVPMXDFUUXTDBB-UHFFFAOYSA-N 1-(2-methoxyphenyl)-4-[2-(4-methoxyphenyl)-1-phenylethyl]piperazine Chemical compound C1=CC(OC)=CC=C1CC(C=1C=CC=CC=1)N1CCN(C=2C(=CC=CC=2)OC)CC1 DVPMXDFUUXTDBB-UHFFFAOYSA-N 0.000 claims 2
- NXCMABMCUAEOJJ-UHFFFAOYSA-N 1-cycloheptyl-4-[2-(4-methoxyphenyl)-1-phenylethyl]piperazine Chemical compound C1=CC(OC)=CC=C1CC(C=1C=CC=CC=1)N1CCN(C2CCCCCC2)CC1 NXCMABMCUAEOJJ-UHFFFAOYSA-N 0.000 claims 2
- KTTKNWVMAWKNFO-UHFFFAOYSA-N 4-[2-(4-cyclohexylpiperazin-1-yl)-2-phenylethyl]phenol Chemical compound C1=CC(O)=CC=C1CC(C=1C=CC=CC=1)N1CCN(C2CCCCC2)CC1 KTTKNWVMAWKNFO-UHFFFAOYSA-N 0.000 claims 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- RQGQMTNIHJECMF-UHFFFAOYSA-N 1-(2-methoxyphenyl)-4-[1-phenyl-2-[4-(trifluoromethyl)phenyl]ethyl]piperazine Chemical compound COC1=CC=CC=C1N1CCN(C(CC=2C=CC(=CC=2)C(F)(F)F)C=2C=CC=CC=2)CC1 RQGQMTNIHJECMF-UHFFFAOYSA-N 0.000 claims 1
- AUJQLPGMLIOIKA-UHFFFAOYSA-N 1-cycloheptyl-4-[2-(4-methylphenyl)-1-phenylethyl]piperazine Chemical compound C1=CC(C)=CC=C1CC(C=1C=CC=CC=1)N1CCN(C2CCCCCC2)CC1 AUJQLPGMLIOIKA-UHFFFAOYSA-N 0.000 claims 1
- 230000000202 analgesic effect Effects 0.000 abstract description 10
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- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 abstract description 3
- 230000003533 narcotic effect Effects 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- 239000000203 mixture Substances 0.000 description 52
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 46
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- 238000005303 weighing Methods 0.000 description 12
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
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- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1047074A JPS5643463B2 (cg-RX-API-DMAC10.html) | 1974-01-23 | 1974-01-23 | |
| JP2892674A JPS5643464B2 (cg-RX-API-DMAC10.html) | 1974-03-12 | 1974-03-12 | |
| JP2968374A JPS5644071B2 (cg-RX-API-DMAC10.html) | 1974-03-14 | 1974-03-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1051433A true CA1051433A (en) | 1979-03-27 |
Family
ID=27278977
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA218,369A Expired CA1051433A (en) | 1974-01-23 | 1975-01-21 | 1-substituted-4-(1,2-diphenylethyl)piperazine derivatives and their salts and the preparation thereof |
Country Status (4)
| Country | Link |
|---|---|
| CA (1) | CA1051433A (cg-RX-API-DMAC10.html) |
| DE (1) | DE2502729A1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2272672B1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1497083A (cg-RX-API-DMAC10.html) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2138016B (en) * | 1983-04-05 | 1986-10-29 | Bostik Ltd | Adhesive bonding |
| JP3571114B2 (ja) * | 1995-07-11 | 2004-09-29 | ポーラ化成工業株式会社 | 麻薬拮抗剤 |
-
1975
- 1975-01-21 CA CA218,369A patent/CA1051433A/en not_active Expired
- 1975-01-22 GB GB277375A patent/GB1497083A/en not_active Expired
- 1975-01-23 FR FR7502167A patent/FR2272672B1/fr not_active Expired
- 1975-01-23 DE DE19752502729 patent/DE2502729A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| GB1497083A (en) | 1978-01-05 |
| FR2272672B1 (cg-RX-API-DMAC10.html) | 1978-07-21 |
| FR2272672A1 (cg-RX-API-DMAC10.html) | 1975-12-26 |
| DE2502729A1 (de) | 1975-07-24 |
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