HUP0700353A2 - Metabolites of (thio)carbamoyl-cyclohexane derivatives - Google Patents
Metabolites of (thio)carbamoyl-cyclohexane derivatives Download PDFInfo
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- HUP0700353A2 HUP0700353A2 HU0700353A HUP0700353A HUP0700353A2 HU P0700353 A2 HUP0700353 A2 HU P0700353A2 HU 0700353 A HU0700353 A HU 0700353A HU P0700353 A HUP0700353 A HU P0700353A HU P0700353 A2 HUP0700353 A2 HU P0700353A2
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- salts
- solvates
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- 239000002207 metabolite Substances 0.000 title claims description 26
- JMMKXVYQBRGGJF-UHFFFAOYSA-N cyclohexanecarbothioamide Chemical class NC(=S)C1CCCCC1 JMMKXVYQBRGGJF-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 143
- 125000004432 carbon atom Chemical group C* 0.000 claims description 69
- 150000003839 salts Chemical class 0.000 claims description 68
- 239000012453 solvate Substances 0.000 claims description 57
- 150000004677 hydrates Chemical class 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 37
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 36
- 229910052717 sulfur Inorganic materials 0.000 claims description 35
- 125000003342 alkenyl group Chemical group 0.000 claims description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 125000004434 sulfur atom Chemical group 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims description 29
- 102000005962 receptors Human genes 0.000 claims description 29
- 108020003175 receptors Proteins 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 125000003435 aroyl group Chemical group 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 108050004812 Dopamine receptor Proteins 0.000 claims description 17
- 102000015554 Dopamine receptor Human genes 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000002950 monocyclic group Chemical group 0.000 claims description 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 125000002619 bicyclic group Chemical group 0.000 claims description 12
- 101150049660 DRD2 gene Proteins 0.000 claims description 11
- -1 cyano, cyclohexyl Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 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 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 238000011161 development Methods 0.000 claims description 4
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 102000004980 Dopamine D2 Receptors Human genes 0.000 claims description 2
- 108090001111 Dopamine D2 Receptors Proteins 0.000 claims description 2
- 102000004073 Dopamine D3 Receptors Human genes 0.000 claims description 2
- 108090000525 Dopamine D3 Receptors Proteins 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 32
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 201000010099 disease Diseases 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
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- GIAOVZPOOUDJDR-UHFFFAOYSA-N 4-[2-[4-(2,3-dichlorophenyl)piperazin-1-yl]ethyl]-1-(dimethylamino)cyclohexane-1-carboxamide Chemical compound C1CC(N(C)C)(C(N)=O)CCC1CCN1CCN(C=2C(=C(Cl)C=CC=2)Cl)CC1 GIAOVZPOOUDJDR-UHFFFAOYSA-N 0.000 description 6
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- 230000008485 antagonism Effects 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
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- RDPGZIWCXXEEFN-UHFFFAOYSA-N 4-[2-[4-(2,3-dichlorophenyl)piperazin-1-yl]ethyl]-1-(dimethylamino)cyclohexane-1-carboxamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C(N)=O)CCC1CCN1CCN(C=2C(=C(Cl)C=CC=2)Cl)CC1 RDPGZIWCXXEEFN-UHFFFAOYSA-N 0.000 description 4
- 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
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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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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
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- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 3
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- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical class C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 2
- XPJZIZBQAIFVSZ-UHFFFAOYSA-N 2-oxocyclohexane-1-carbothioamide Chemical class NC(=S)C1CCCCC1=O XPJZIZBQAIFVSZ-UHFFFAOYSA-N 0.000 description 2
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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
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- 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
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- 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
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- 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
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- 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)
Priority Applications (24)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0700353A HUP0700353A2 (en) | 2007-05-18 | 2007-05-18 | Metabolites of (thio)carbamoyl-cyclohexane derivatives |
| NZ580646A NZ580646A (en) | 2007-05-18 | 2008-05-15 | Metabolites of (thio)carbamoyl-cyclohexane derivatives |
| BRPI0811744-6A2A BRPI0811744A2 (pt) | 2007-05-18 | 2008-05-15 | Metabólitos dos derivados de (tio)carbamoil-ciclohexano |
| GEAP200811607A GEP20125523B (en) | 2007-05-18 | 2008-05-15 | Metabolites of (thio) carbamoyl-cyclohexane derivatives |
| CN200880016466A CN101679330A (zh) | 2007-05-18 | 2008-05-15 | （硫代）氨基甲酰基-环己烷衍生物的代谢产物 |
| EP08750836A EP2155707B1 (en) | 2007-05-18 | 2008-05-15 | Metabolites of carbamoyl-cyclohexane derivatives |
| JP2010508911A JP5406827B2 (ja) | 2007-05-18 | 2008-05-15 | （チオ）カルバモイル−シクロヘキサン誘導体の代謝物 |
| EA200971069A EA200971069A1 (ru) | 2007-05-18 | 2008-05-15 | Метаболиты производных (тио)карбомоилциклогексана |
| MYPI20094707 MY150784A (en) | 2007-05-18 | 2008-05-15 | Metabolites of (thio) carbamoyl-cyclohexane derivatives |
| MX2009012371A MX2009012371A (es) | 2007-05-18 | 2008-05-15 | Metabolitos de derivados de (tio)-carbamoil-ciclohexano. |
| CA2684149A CA2684149C (en) | 2007-05-18 | 2008-05-15 | Metabolites of (thio)carbamoyl-cyclohexane derivatives |
| AP2009005011A AP2009005011A0 (en) | 2007-05-18 | 2008-05-15 | Metabolites of (thio)-carbamoyl-cyclohexane derivatives |
| PCT/HU2008/000046 WO2008142461A1 (en) | 2007-05-18 | 2008-05-15 | Metabolites of (thio)carbamoyl-cyclohexane derivatives |
| AU2008252619A AU2008252619A1 (en) | 2007-05-18 | 2008-05-15 | Metabolites of (thio)carbamoyl-cyclohexane derivatives |
| US12/600,826 US8765765B2 (en) | 2007-05-18 | 2008-05-15 | Metabolites of (thio) carbamoyl-cyclohexane derivatives |
| TW097125708A TW201002324A (en) | 2007-05-18 | 2008-07-08 | Metabolites of (thio) carbamoyl-cyclohexane derivatives |
| IL201534A IL201534A0 (en) | 2007-05-18 | 2009-10-15 | Metabolites of (thio) carbamoyl-cyclhoxane derivatives |
| ZA200907425A ZA200907425B (en) | 2007-05-18 | 2009-10-22 | Metabolites of (thio)carbamoyl-cyclohexane derivatives |
| TNP2009000459A TN2009000459A1 (en) | 2007-05-18 | 2009-10-30 | Metabolites of (thio) carbamoyl-cyclohexane derivatives |
| NI200900202A NI200900202A (es) | 2007-05-18 | 2009-11-09 | Metabolitos de derivados del (tio) - carbamoil - ciclohexano. |
| CU2009000196A CU23852B1 (es) | 2007-05-18 | 2009-11-17 | Metabolitos de derivados del (tio)-carbamoil-ciclohexano |
| MA32403A MA31432B1 (fr) | 2007-05-18 | 2009-12-07 | Metabolites de derives de (thio) carbamoyl-cyclohexane |
| CO09144002A CO6251252A2 (es) | 2007-05-18 | 2009-12-16 | Metabolitos de derivados del (tio)-carbamoil-ciclohexano |
| EC2009009819A ECSP099819A (es) | 2007-05-18 | 2009-12-18 | Metabolitos de derivados del (tio)-carbamoil-ciclohexano |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0700353A HUP0700353A2 (en) | 2007-05-18 | 2007-05-18 | Metabolites of (thio)carbamoyl-cyclohexane derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HU0700353D0 HU0700353D0 (en) | 2007-07-30 |
| HUP0700353A2 true HUP0700353A2 (en) | 2008-12-29 |
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| HU0700353A HUP0700353A2 (en) | 2007-05-18 | 2007-05-18 | Metabolites of (thio)carbamoyl-cyclohexane derivatives |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
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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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- 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 BR BRPI0811744-6A2A patent/BRPI0811744A2/pt not_active IP Right Cessation
- 2008-05-15 EP EP08750836A patent/EP2155707B1/en active Active
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- 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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- 2009-11-17 CU CU2009000196A patent/CU23852B1/es not_active IP Right Cessation
- 2009-12-07 MA MA32403A patent/MA31432B1/fr unknown
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Also Published As
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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 |
| CA2684149C (en) | 2012-12-04 |
| 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 |
| 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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