CA2684149C - Metabolites of (thio)carbamoyl-cyclohexane derivatives - Google Patents
Metabolites of (thio)carbamoyl-cyclohexane derivatives Download PDFInfo
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- CA2684149C CA2684149C CA2684149A CA2684149A CA2684149C CA 2684149 C CA2684149 C CA 2684149C CA 2684149 A CA2684149 A CA 2684149A CA 2684149 A CA2684149 A CA 2684149A CA 2684149 C CA2684149 C CA 2684149C
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- 239000002207 metabolite Substances 0.000 title abstract description 16
- JMMKXVYQBRGGJF-UHFFFAOYSA-N cyclohexanecarbothioamide Chemical class NC(=S)C1CCCCC1 JMMKXVYQBRGGJF-UHFFFAOYSA-N 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 101
- 150000003839 salts Chemical class 0.000 claims abstract description 27
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 239000012453 solvate Substances 0.000 claims description 15
- 208000028017 Psychotic disease Diseases 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 208000035475 disorder Diseases 0.000 claims description 10
- 201000000980 schizophrenia Diseases 0.000 claims description 10
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 206010012289 Dementia Diseases 0.000 claims description 8
- 208000010877 cognitive disease Diseases 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 7
- 206010013654 Drug abuse Diseases 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- 208000011117 substance-related disease Diseases 0.000 claims description 6
- 206010026749 Mania Diseases 0.000 claims description 5
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- 125000001589 carboacyl group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 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 description 4
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
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- 229910052757 nitrogen Inorganic materials 0.000 abstract description 9
- PZWXYRDNQYUIIU-UHFFFAOYSA-N 3-cyclohexyl-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1CCCCC1 PZWXYRDNQYUIIU-UHFFFAOYSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 32
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- 230000000694 effects Effects 0.000 description 9
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
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- 150000004677 hydrates Chemical class 0.000 description 5
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
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- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- 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
- C07D295/12—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 or doubly bound nitrogen atoms
- C07D295/135—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D295/22—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 hetero atoms directly attached to ring nitrogen atoms
- C07D295/24—Oxygen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUP0700353 | 2007-05-18 | ||
| HU0700353A HUP0700353A2 (en) | 2007-05-18 | 2007-05-18 | Metabolites of (thio)carbamoyl-cyclohexane derivatives |
| PCT/HU2008/000046 WO2008142461A1 (en) | 2007-05-18 | 2008-05-15 | Metabolites of (thio)carbamoyl-cyclohexane derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2684149A1 CA2684149A1 (en) | 2008-11-27 |
| CA2684149C true CA2684149C (en) | 2012-12-04 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2684149A Expired - Fee Related CA2684149C (en) | 2007-05-18 | 2008-05-15 | Metabolites of (thio)carbamoyl-cyclohexane derivatives |
Country Status (24)
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP0700353A2 (en) | 2007-05-18 | 2008-12-29 | Richter Gedeon Nyrt | Metabolites of (thio)carbamoyl-cyclohexane derivatives |
| US7875610B2 (en) | 2007-12-03 | 2011-01-25 | Richter Gedeon Nyrt. | Pyrimidinyl-piperazines useful as D3/D2 receptor ligands |
| CA2715760C (en) * | 2008-02-21 | 2017-06-13 | Mitsubishi Tanabe Pharma Corporation | Solid preparation for oral administration of cariprazine hydrochloride |
| KR101612146B1 (ko) | 2008-07-16 | 2016-04-12 | 리히터 게데온 닐트. | 도파민 수용체 리간드를 함유하는 약학적 제형 |
| HU230067B1 (hu) | 2008-12-17 | 2015-06-29 | Richter Gedeon Nyrt | Új piperazin só és eljárás előállítására |
| HUP0800765A2 (en) * | 2008-12-18 | 2010-11-29 | Richter Gedeon Nyrt | A new process for the preparation of piperazine derivatives and their hydrochloric salts |
| HUP0800766A2 (en) | 2008-12-18 | 2010-11-29 | Richter Gedeon Vegyeszet | Process for the preparation of piperazine derivatives |
| JP5836280B2 (ja) * | 2009-11-06 | 2015-12-24 | エスケー バイオファーマスティカルズ カンパニー リミテッド | 注意欠陥／多動性障害（ａｄｈｄ）の治療方法 |
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| HUP0800766A2 (en) | 2008-12-18 | 2010-11-29 | Richter Gedeon Vegyeszet | Process for the preparation of piperazine derivatives |
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2007
- 2007-05-18 HU HU0700353A patent/HUP0700353A2/hu unknown
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2008
- 2008-05-15 US US12/600,826 patent/US8765765B2/en active Active
- 2008-05-15 NZ NZ580646A patent/NZ580646A/en unknown
- 2008-05-15 AU AU2008252619A patent/AU2008252619A1/en not_active Abandoned
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- 2008-05-15 MY MYPI20094707 patent/MY150784A/en unknown
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- 2008-05-15 BR BRPI0811744-6A2A patent/BRPI0811744A2/pt not_active IP Right Cessation
- 2008-05-15 EP EP08750836A patent/EP2155707B1/en active Active
- 2008-05-15 AP AP2009005011A patent/AP2009005011A0/xx unknown
- 2008-05-15 CN CN200880016466A patent/CN101679330A/zh active Pending
- 2008-05-15 JP JP2010508911A patent/JP5406827B2/ja active Active
- 2008-05-15 EA EA200971069A patent/EA200971069A1/ru unknown
- 2008-05-15 CA CA2684149A patent/CA2684149C/en not_active Expired - Fee Related
- 2008-05-15 WO PCT/HU2008/000046 patent/WO2008142461A1/en not_active Ceased
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- 2009-12-16 CO CO09144002A patent/CO6251252A2/es not_active Application Discontinuation
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| JP5406827B2 (ja) | 2014-02-05 |
| ECSP099819A (es) | 2010-03-31 |
| BRPI0811744A2 (pt) | 2014-11-11 |
| EP2155707A1 (en) | 2010-02-24 |
| NZ580646A (en) | 2012-03-30 |
| NI200900202A (es) | 2010-03-11 |
| HU0700353D0 (en) | 2007-07-30 |
| US20100137335A1 (en) | 2010-06-03 |
| TN2009000459A1 (en) | 2011-03-31 |
| CO6251252A2 (es) | 2011-02-21 |
| MA31432B1 (fr) | 2010-06-01 |
| HUP0700353A2 (en) | 2008-12-29 |
| AU2008252619A1 (en) | 2008-11-27 |
| ZA200907425B (en) | 2010-07-28 |
| CU20090196A7 (es) | 2011-07-11 |
| GEP20125523B (en) | 2012-05-25 |
| US8765765B2 (en) | 2014-07-01 |
| CA2684149A1 (en) | 2008-11-27 |
| AP2009005011A0 (en) | 2009-10-31 |
| TW201002324A (en) | 2010-01-16 |
| JP2010527983A (ja) | 2010-08-19 |
| EA200971069A1 (ru) | 2010-04-30 |
| IL201534A0 (en) | 2010-05-31 |
| MY150784A (en) | 2014-02-28 |
| EP2155707B1 (en) | 2013-03-13 |
| MX2009012371A (es) | 2009-12-03 |
| CN101679330A (zh) | 2010-03-24 |
| WO2008142461A1 (en) | 2008-11-27 |
| CU23852B1 (es) | 2012-10-15 |
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