DE1470124B2 - 1- geschweifte klammer auf 1- eckige klammer auf 4,4-bis(p-fluorphenyl)- butyl eckige klammer zu -4-piperidyl geschweifte klammer zu -2-benzimidazolinon und verfahren zu seiner herstellung - Google Patents
1- geschweifte klammer auf 1- eckige klammer auf 4,4-bis(p-fluorphenyl)- butyl eckige klammer zu -4-piperidyl geschweifte klammer zu -2-benzimidazolinon und verfahren zu seiner herstellungInfo
- Publication number
- DE1470124B2 DE1470124B2 DE1963N0023307 DEN0023307A DE1470124B2 DE 1470124 B2 DE1470124 B2 DE 1470124B2 DE 1963N0023307 DE1963N0023307 DE 1963N0023307 DE N0023307 A DEN0023307 A DE N0023307A DE 1470124 B2 DE1470124 B2 DE 1470124B2
- Authority
- DE
- Germany
- Prior art keywords
- bracket
- square
- benzimidazolinone
- piperidyl
- preparation
- 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.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- -1 hydrochloric acid ester Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical class C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 description 2
- UXXLTPGCINZEFM-UHFFFAOYSA-N 1-[4-chloro-1-(4-fluorophenyl)butyl]-4-fluorobenzene Chemical compound C1=CC(F)=CC=C1C(CCCCl)C1=CC=C(F)C=C1 UXXLTPGCINZEFM-UHFFFAOYSA-N 0.000 description 2
- BYNBAMHAURJNTR-UHFFFAOYSA-N 3-piperidin-4-yl-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1C1CCNCC1 BYNBAMHAURJNTR-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003176 neuroleptic agent Substances 0.000 description 2
- 230000000701 neuroleptic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- FKCKAEJWXGMCFZ-UHFFFAOYSA-N 3-(1-benzyl-3,6-dihydro-2h-pyridin-4-yl)-1h-benzimidazol-2-one Chemical group O=C1NC2=CC=CC=C2N1C(CC1)=CCN1CC1=CC=CC=C1 FKCKAEJWXGMCFZ-UHFFFAOYSA-N 0.000 description 1
- WMPRRSYNQDCNCE-UHFFFAOYSA-N 3-(1-benzylpiperidin-4-yl)-1h-benzimidazol-2-one Chemical class O=C1NC2=CC=CC=C2N1C(CC1)CCN1CC1=CC=CC=C1 WMPRRSYNQDCNCE-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- 229960001076 chlorpromazine Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- YAKFETHTYBAIJR-UHFFFAOYSA-N cyclopropyl-bis(4-fluorophenyl)methanol Chemical compound C=1C=C(F)C=CC=1C(C=1C=CC(F)=CC=1)(O)C1CC1 YAKFETHTYBAIJR-UHFFFAOYSA-N 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229960003878 haloperidol Drugs 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- YVUQSNJEYSNKRX-UHFFFAOYSA-N pimozide Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1CCC(N2C(NC3=CC=CC=C32)=O)CC1 YVUQSNJEYSNKRX-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20205662A | 1962-06-13 | 1962-06-13 | |
| US286911A US3196157A (en) | 1962-06-13 | 1963-06-11 | Benzimidazolinyl piperidines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1470124A1 DE1470124A1 (de) | 1969-05-08 |
| DE1470124B2 true DE1470124B2 (de) | 1976-12-09 |
Family
ID=26897320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1963N0023307 Granted DE1470124B2 (de) | 1962-06-13 | 1963-06-12 | 1- geschweifte klammer auf 1- eckige klammer auf 4,4-bis(p-fluorphenyl)- butyl eckige klammer zu -4-piperidyl geschweifte klammer zu -2-benzimidazolinon und verfahren zu seiner herstellung |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3196157A (en, 2012) |
| BE (1) | BE633495A (en, 2012) |
| BR (1) | BR6349833D0 (en, 2012) |
| CH (1) | CH450437A (en, 2012) |
| DE (1) | DE1470124B2 (en, 2012) |
| DK (1) | DK119165C (en, 2012) |
| FR (2) | FR3695M (en, 2012) |
| GB (1) | GB1039923A (en, 2012) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4080328A (en) * | 1971-07-13 | 1978-03-21 | Sumitomo Chemical Company, Limited | N-substituted heterocyclic derivatives and preparation thereof |
| JPS5527915B2 (en, 2012) * | 1971-11-25 | 1980-07-24 | ||
| US3910930A (en) * | 1973-01-04 | 1975-10-07 | Janssen Pharmaceutica Nv | 1-{55 1-{8 2-(1,4-Benzodioxan-2-yl)-2-hydroxyethyl{9 -4-piperidyl{56 -2-benzimidazolinones |
| US3929801A (en) * | 1973-11-20 | 1975-12-30 | Janssen Pharmaceutica Nv | 2-Benzimidazolinones |
| JPS5416505B2 (en, 2012) * | 1973-11-30 | 1979-06-22 | ||
| US3989707A (en) * | 1974-06-21 | 1976-11-02 | Janssen Pharmaceutica N.V. | Benzimidazolinone derivatives |
| US3996362A (en) * | 1975-05-28 | 1976-12-07 | E. R. Squibb & Sons, Inc. | 2-[[4-(2,3-Dihydro-2-oxo-1H-benzimidazol-1-yl)-1-(piperidinyl or 1,2,3,6-tetrahydro-1-pyridinyl)]alkyl]-1H-benz[de]isoquinoline-1,3(2H)-diones |
| US4066772A (en) * | 1975-07-21 | 1978-01-03 | Janssen Pharmaceutica N.V. | 1,3-Dihydro-1-[3-(1-piperidinyl)propyl]-2H-benzimidazol-2-ones and related compounds |
| NZ181256A (en) * | 1975-07-21 | 1978-04-28 | Janssen Pharmaceutica Nv | 1-(w-benzazol-11-ylalkyl)-piperidine derivatives and pharmaceutical compositions containing certain of these derivatives |
| US4005211A (en) * | 1975-09-10 | 1977-01-25 | Janssen Pharmaceutica N.V. | Lactation stimulation employing pimozide |
| US4035369A (en) * | 1975-10-08 | 1977-07-12 | Janssen Pharmaceutica N.V. | 1-Benzazolylalkyl-4-substituted-piperidines |
| US4200755A (en) * | 1979-05-04 | 1980-04-29 | Richardson-Merrell Inc. | 2-Hydroxy-5-[1-hydroxy-2-[4-(2-oxo-1-benzimidazolinyl)piperidino]ethyl]benzoic acid derivatives |
| US4264613A (en) * | 1979-08-01 | 1981-04-28 | Science Union Et Cie, Societe Francaise De Recherche Medicale | Piperidylbenzimidazolinone compounds |
| US4352811A (en) * | 1981-11-12 | 1982-10-05 | Hoechst-Roussel Pharmaceuticals Inc. | 3-(1-Substituted-4-piperidyl)-1,2-benzisoxazoles |
| US5059600A (en) * | 1989-03-31 | 1991-10-22 | Yale University | Treating habit disorders |
| US5223497A (en) * | 1989-03-31 | 1993-06-29 | Yale University | Treating habit disorders |
| US5114942A (en) * | 1989-03-31 | 1992-05-19 | Yale University | Treating habit disorders |
| ATE341542T1 (de) | 1996-04-19 | 2006-10-15 | Neurosearch As | 1-(4-piperidyl)-benzimidazole mit neurotropher aktivität |
| DE60022226D1 (de) * | 1999-12-06 | 2005-09-29 | Euro Celtique Sa | Benzimidazolverbindungen die nociceptinrezeptoraffinität haben |
| US6790854B2 (en) | 2000-03-24 | 2004-09-14 | Meiji Seika Kaisha, Ltd. | Diphenylalkylamine derivatives useful as opioid receptor agonists |
| KR20030043970A (ko) * | 2000-10-12 | 2003-06-02 | 에스에스 세야쿠 가부시키 가이샤 | 2,2-디페닐부탄아미드 유도체 및 이를 함유하는 의약 |
| US8354434B2 (en) * | 2006-01-30 | 2013-01-15 | Purdue Pharma L.P. | Cyclourea compounds as calcium channel blockers |
| PL2132175T3 (pl) | 2006-12-28 | 2012-09-28 | Inst Univ Ciencia I Tecnologia | Sposób wytwarzania loperamidu |
| CN113637001A (zh) * | 2021-08-09 | 2021-11-12 | 安康市农业科学研究院 | 一种氟哌利多中间体的合成方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3080366A (en) * | 1961-06-13 | 1963-03-05 | Res Lab Dr C Janssen | 1-(omega, omega-diphenylalkyl)-4-amino-4-piperidinecarboxyamides and derivatives thereof |
-
0
- BE BE633495D patent/BE633495A/xx unknown
-
1963
- 1963-06-11 US US286911A patent/US3196157A/en not_active Expired - Lifetime
- 1963-06-12 BR BR149833/63A patent/BR6349833D0/pt unknown
- 1963-06-12 DE DE1963N0023307 patent/DE1470124B2/de active Granted
- 1963-06-12 GB GB23483/63A patent/GB1039923A/en not_active Expired
- 1963-06-13 DK DK279763AA patent/DK119165C/da active
- 1963-06-13 CH CH739463A patent/CH450437A/de unknown
- 1963-09-12 FR FR947310A patent/FR3695M/fr active Active
- 1963-09-12 FR FR947311A patent/FR3042M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1039923A (en) | 1966-08-24 |
| DE1795844B2 (de) | 1977-03-31 |
| BE633495A (en, 2012) | |
| FR3695M (fr) | 1965-11-22 |
| DK119165B (en, 2012) | 1970-11-23 |
| DE1795844A1 (de) | 1976-10-21 |
| BR6349833D0 (pt) | 1973-07-03 |
| US3196157A (en) | 1965-07-20 |
| CH450437A (de) | 1968-01-31 |
| DK119165C (da) | 1971-04-05 |
| FR3042M (fr) | 1965-01-04 |
| DE1470124A1 (de) | 1969-05-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |