NO131172B - - Google Patents
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- Publication number
- NO131172B NO131172B NO4046/70A NO404670A NO131172B NO 131172 B NO131172 B NO 131172B NO 4046/70 A NO4046/70 A NO 4046/70A NO 404670 A NO404670 A NO 404670A NO 131172 B NO131172 B NO 131172B
- Authority
- NO
- Norway
- Prior art keywords
- trifluoromethylphenyl
- piperidine
- reacted
- general formula
- compounds
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 12
- IPKSNWXGEIHOMR-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenyl]piperidine Chemical compound FC(F)(F)C1=CC=CC(C2CCNCC2)=C1 IPKSNWXGEIHOMR-UHFFFAOYSA-N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- -1 1-carbamoyl-4-(m-trifluoromethylphenyl)piperidine Chemical compound 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- CMUOJBJRZUHRMU-UHFFFAOYSA-N nitrourea Chemical compound NC(=O)N[N+]([O-])=O CMUOJBJRZUHRMU-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- NOHQUGRVHSJYMR-UHFFFAOYSA-N 1-chloro-2-isocyanatobenzene Chemical compound ClC1=CC=CC=C1N=C=O NOHQUGRVHSJYMR-UHFFFAOYSA-N 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- IFYKRMQORZOMNY-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCNCC=2)=C1 IFYKRMQORZOMNY-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 206010010904 Convulsion Diseases 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- 239000001961 anticonvulsive agent Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000036461 convulsion Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 230000001773 anti-convulsant effect Effects 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- FZOKXDNYTHYNPE-UHFFFAOYSA-N 4-phenylpiperidine-1-carboxamide Chemical class C1CN(C(=O)N)CCC1C1=CC=CC=C1 FZOKXDNYTHYNPE-UHFFFAOYSA-N 0.000 description 3
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229960003965 antiepileptics Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- GJTGVCFKLBBSNT-UHFFFAOYSA-N 1-benzyl-4-[3-(trifluoromethyl)phenyl]piperidin-4-ol Chemical compound C1CC(O)(C=2C=C(C=CC=2)C(F)(F)F)CCN1CC1=CC=CC=C1 GJTGVCFKLBBSNT-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229940125681 anticonvulsant agent Drugs 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000003158 myorelaxant agent Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- HHIRBXHEYVDUAM-UHFFFAOYSA-N 1-chloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1 HHIRBXHEYVDUAM-UHFFFAOYSA-N 0.000 description 1
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical class C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 1
- ILKPZCKFWLTEBQ-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenyl]piperidin-4-ol Chemical compound C=1C=CC(C(F)(F)F)=CC=1C1(O)CCNCC1 ILKPZCKFWLTEBQ-UHFFFAOYSA-N 0.000 description 1
- SBKPKQORDCJPSQ-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenyl]piperidin-4-ol;hydrochloride Chemical compound Cl.C=1C=CC(C(F)(F)F)=CC=1C1(O)CCNCC1 SBKPKQORDCJPSQ-UHFFFAOYSA-N 0.000 description 1
- 241000402754 Erythranthe moschata Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- WSWOKFODOPIESP-UHFFFAOYSA-M [Br-].FC(F)(F)C1=CC=CC([Mg+])=C1 Chemical compound [Br-].FC(F)(F)C1=CC=CC([Mg+])=C1 WSWOKFODOPIESP-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 230000000954 anitussive effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical compound ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229960003810 piperidione Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/02—Preparation by ring-closure or hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86988169A | 1969-10-27 | 1969-10-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO131172B true NO131172B (hu) | 1975-01-06 |
| NO131172C NO131172C (hu) | 1975-04-16 |
Family
ID=25354406
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4046/70A NO131172C (hu) | 1969-10-27 | 1970-10-26 |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS4939266B1 (hu) |
| AT (1) | AT302354B (hu) |
| BE (1) | BE757436A (hu) |
| CA (1) | CA918161A (hu) |
| CH (1) | CH525886A (hu) |
| DE (1) | DE2048589A1 (hu) |
| ES (1) | ES384311A1 (hu) |
| FR (1) | FR2070167B1 (hu) |
| GB (1) | GB1307277A (hu) |
| NL (1) | NL7015396A (hu) |
| NO (1) | NO131172C (hu) |
| PH (1) | PH9289A (hu) |
| SE (2) | SE382454B (hu) |
| ZA (1) | ZA707307B (hu) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4357471A (en) | 1976-12-17 | 1982-11-02 | Rohm And Haas Company | Azaspiro compounds |
| US4374991A (en) | 1976-12-17 | 1983-02-22 | Rohm And Haas Company | 2,6-Dimethylpiperidinyl-N-carbobutoxymethyl urea |
| US4400512A (en) * | 1976-12-17 | 1983-08-23 | Rohm And Haas Company | Azaspiro compounds |
| US4405630A (en) * | 1980-12-29 | 1983-09-20 | Rohm And Haas Company | Arthropod repellent compositions and methods |
| FR2501506A1 (fr) * | 1981-03-11 | 1982-09-17 | Sanofi Sa | Compositions pharmaceutiques a action anorexigene contenant des derives de la tetrahydropyridine |
| JP4521777B2 (ja) * | 2003-07-24 | 2010-08-11 | ユーロ−セルティーク エス．エイ． | 疼痛治療または予防に有用な４−ヘテロアリール−テトラヒドロピペリジル化合物 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1087174A (en) * | 1965-04-05 | 1967-10-11 | Allen & Hanburys Ltd | Piperidine derivatives |
| FR1589754A (hu) * | 1968-10-17 | 1970-04-06 |
-
0
- BE BE757436D patent/BE757436A/xx unknown
-
1970
- 1970-10-02 DE DE19702048589 patent/DE2048589A1/de active Pending
- 1970-10-07 ES ES384311A patent/ES384311A1/es not_active Expired
- 1970-10-15 SE SE7312890A patent/SE382454B/xx unknown
- 1970-10-15 SE SE7013959A patent/SE372942B/xx unknown
- 1970-10-20 CH CH1546970A patent/CH525886A/fr not_active IP Right Cessation
- 1970-10-21 NL NL7015396A patent/NL7015396A/xx unknown
- 1970-10-22 PH PH11886*UA patent/PH9289A/en unknown
- 1970-10-23 GB GB5050970A patent/GB1307277A/en not_active Expired
- 1970-10-26 FR FR7038570A patent/FR2070167B1/fr not_active Expired
- 1970-10-26 CA CA096580A patent/CA918161A/en not_active Expired
- 1970-10-26 NO NO4046/70A patent/NO131172C/no unknown
- 1970-10-27 AT AT966570A patent/AT302354B/de not_active IP Right Cessation
- 1970-10-27 ZA ZA707307A patent/ZA707307B/xx unknown
- 1970-10-27 JP JP45094014A patent/JPS4939266B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| SE382454B (sv) | 1976-02-02 |
| NL7015396A (hu) | 1971-04-29 |
| AT302354B (de) | 1972-10-10 |
| SE372942B (hu) | 1975-01-20 |
| NO131172C (hu) | 1975-04-16 |
| DE2048589A1 (de) | 1971-05-06 |
| ZA707307B (en) | 1971-07-28 |
| BE757436A (fr) | 1971-03-16 |
| PH9289A (en) | 1975-08-13 |
| CH525886A (fr) | 1972-07-31 |
| FR2070167B1 (hu) | 1975-03-14 |
| GB1307277A (en) | 1973-02-14 |
| JPS4939266B1 (hu) | 1974-10-24 |
| FR2070167A1 (hu) | 1971-09-10 |
| ES384311A1 (es) | 1973-09-01 |
| CA918161A (en) | 1973-01-02 |
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