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
-
- 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)
- Psychology (AREA)
- Psychiatry (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 |
| CA2684149A CA2684149C (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 |
| NZ580646A NZ580646A (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 |
| EP08750836A EP2155707B1 (en) | 2007-05-18 | 2008-05-15 | Metabolites of carbamoyl-cyclohexane derivatives |
| MX2009012371A MX2009012371A (es) | 2007-05-18 | 2008-05-15 | Metabolitos de derivados de (tio)-carbamoil-ciclohexano. |
| US12/600,826 US8765765B2 (en) | 2007-05-18 | 2008-05-15 | Metabolites of (thio) carbamoyl-cyclohexane derivatives |
| MYPI20094707 MY150784A (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 |
| 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 |
| 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 |
| 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 |
| 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 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0700353A HUP0700353A2 (en) | 2007-05-18 | 2007-05-18 | Metabolites of (thio)carbamoyl-cyclohexane derivatives |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US8765765B2 (OSRAM) |
| EP (1) | EP2155707B1 (OSRAM) |
| JP (1) | JP5406827B2 (OSRAM) |
| CN (1) | CN101679330A (OSRAM) |
| AP (1) | AP2009005011A0 (OSRAM) |
| AU (1) | AU2008252619A1 (OSRAM) |
| BR (1) | BRPI0811744A2 (OSRAM) |
| CA (1) | CA2684149C (OSRAM) |
| CO (1) | CO6251252A2 (OSRAM) |
| CU (1) | CU23852B1 (OSRAM) |
| EA (1) | EA200971069A1 (OSRAM) |
| EC (1) | ECSP099819A (OSRAM) |
| GE (1) | GEP20125523B (OSRAM) |
| HU (1) | HUP0700353A2 (OSRAM) |
| IL (1) | IL201534A0 (OSRAM) |
| MA (1) | MA31432B1 (OSRAM) |
| MX (1) | MX2009012371A (OSRAM) |
| MY (1) | MY150784A (OSRAM) |
| NI (1) | NI200900202A (OSRAM) |
| NZ (1) | NZ580646A (OSRAM) |
| TN (1) | TN2009000459A1 (OSRAM) |
| TW (1) | TW201002324A (OSRAM) |
| WO (1) | WO2008142461A1 (OSRAM) |
| ZA (1) | ZA200907425B (OSRAM) |
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 |
| WO2009104739A1 (ja) * | 2008-02-21 | 2009-08-27 | 田辺三菱製薬株式会社 | 経口投与用固形製剤 |
| UA104869C2 (uk) | 2008-07-16 | 2014-03-25 | Ріхтер Гедеон Нірт. | Фармацевтичні композиції, що містять ліганди рецептора дофаміну |
| 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 |
| ES2447295T3 (es) * | 2009-11-06 | 2014-03-11 | Sk Biopharmaceuticals Co., Ltd. | Métodos para el tratamiento del trastorno de déficit de atención/hiperactividad |
| WO2011060363A2 (en) * | 2009-11-16 | 2011-05-19 | Auspex Pharmaceuticals, Inc. | Cyclohexyl urea modulators of d2 receptors and/or d3 receptors |
| HUP0900790A2 (en) * | 2009-12-17 | 2011-09-28 | Richter Gedeon Nyrt | A new process for the preparation of piperazine and their hydrochloric salts |
| WO2014031162A1 (en) * | 2012-08-20 | 2014-02-27 | Forest Laboratories Holdings Limited | Crystalline form of carbamoyl-cyclohexane derivatives |
| US11274087B2 (en) | 2016-07-08 | 2022-03-15 | Richter Gedeon Nyrt. | Industrial process for the preparation of cariprazine |
| WO2018153297A1 (zh) * | 2017-02-24 | 2018-08-30 | 深圳市灵兰生物医药科技有限公司 | 新型多巴胺d3受体选择性配体及其制备方法和医药应用 |
| CN108586389B (zh) * | 2018-06-29 | 2020-06-12 | 成都福柯斯医药技术有限公司 | 一种合成卡利拉嗪的方法 |
| HU231500B1 (hu) | 2019-04-10 | 2024-04-28 | Richter Gedeon Nyrt | Karbamoil-ciklohexán származékok autizmus spektrum betegség kezelésére |
| US11547707B2 (en) | 2019-04-10 | 2023-01-10 | Richter Gedeon Nyrt. | Carbamoyl cyclohexane derivatives for treating autism spectrum disorder |
| CN112239433B (zh) * | 2019-07-17 | 2024-05-14 | 北京盈科瑞创新药物研究有限公司 | 一种环己烷衍生物、制备方法及其应用 |
| TW202118758A (zh) * | 2019-11-05 | 2021-05-16 | 大陸商上海翰森生物醫藥科技有限公司 | 苯并噻吩類衍生物調節劑、其製備方法和應用 |
| WO2024072930A1 (en) * | 2022-09-30 | 2024-04-04 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Dopamine d3/d2 receptor partial agonists for the treatment of neuropsychiatric disorders |
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| HU227543B1 (en) | 2001-09-28 | 2011-08-29 | Richter Gedeon Nyrt | N-[4-(2-piperazin- and 2-piperidin-1-yl-ethyl)-cyclohexyl]-sulfon- and sulfamides, process for their preparation, their use and pharmaceutical compositions containing them |
| SE0200301D0 (sv) * | 2002-02-01 | 2002-02-01 | Axon Biochemicals Bv | Thio-carbostyril derivative |
| US6919342B2 (en) | 2003-06-05 | 2005-07-19 | Abbott Gmbh & Co. Kg | Triazole compounds suitable for treating disorders that respond to modulation of the dopamine D3 receptor |
| HU227534B1 (en) | 2003-08-04 | 2011-08-29 | Richter Gedeon Nyrt | (thio)carbamoyl-cyclohexane derivatives, process for producing them and pharmaceutical compositions containing them |
| DE102004047517A1 (de) | 2004-09-28 | 2006-03-30 | Merck Patent Gmbh | Neuartige Kristallform von (3-Cyan-1H-indol-7-yl)-[4-(4-fluorphenethyl)-piperazin-1-yl]-methanon, Hydrochlorid |
| HUP0500170A3 (en) | 2005-02-03 | 2007-11-28 | Richter Gedeon Nyrt | Piperazine derivatives, process for producing them and pharmaceutical compositions containing them |
| GT200600414A (es) | 2005-09-12 | 2007-09-20 | Sal de glucuranato de compuesto de piperazine | |
| HU230748B1 (hu) | 2007-05-11 | 2018-02-28 | Richter Gedeon Nyrt | Új piperazin só és előállítási eljárása |
| HUE033357T2 (en) | 2007-05-11 | 2017-11-28 | Richter Gedeon Nyrt | Crystalline form of carbamoylcyclohexane derivatives |
| HUP0700353A2 (en) | 2007-05-18 | 2008-12-29 | Richter Gedeon Nyrt | Metabolites of (thio)carbamoyl-cyclohexane derivatives |
| HUP0700370A2 (en) | 2007-05-24 | 2009-04-28 | Richter Gedeon Nyrt | Use of (thio)-carbamoyl-cyclohexane derivatives in the manufacture of a medicament for the treatment of acute mania |
| HUP0700369A2 (en) | 2007-05-24 | 2009-04-28 | Richter Gedeon Nyrt | Use of (thio)-carbamoyl-cyclohexane derivatives in the manufacture of a medicament for the treatment in the manufacture of a medicament for the treatment of schizophrenia |
| US20100256145A1 (en) | 2007-08-01 | 2010-10-07 | H. Lundbeck A/S | Use of kcnq potassium channel openers for reducing symptoms of or treating disorders or conditions wherein the dopaminergic system is disrupted |
| US7875610B2 (en) | 2007-12-03 | 2011-01-25 | Richter Gedeon Nyrt. | Pyrimidinyl-piperazines useful as D3/D2 receptor ligands |
| WO2009104739A1 (ja) | 2008-02-21 | 2009-08-27 | 田辺三菱製薬株式会社 | 経口投与用固形製剤 |
| UA104869C2 (uk) | 2008-07-16 | 2014-03-25 | Ріхтер Гедеон Нірт. | Фармацевтичні композиції, що містять ліганди рецептора дофаміну |
| HU230067B1 (hu) | 2008-12-17 | 2015-06-29 | Richter Gedeon Nyrt | Új piperazin só és eljárás előállítására |
| HUP0800766A2 (en) | 2008-12-18 | 2010-11-29 | Richter Gedeon Vegyeszet | Process for the preparation of piperazine derivatives |
| HUP0800765A2 (en) | 2008-12-18 | 2010-11-29 | Richter Gedeon Nyrt | A new process for the preparation of piperazine derivatives and their hydrochloric salts |
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2007
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2008
- 2008-05-15 AP AP2009005011A patent/AP2009005011A0/xx unknown
- 2008-05-15 NZ NZ580646A patent/NZ580646A/en unknown
- 2008-05-15 WO PCT/HU2008/000046 patent/WO2008142461A1/en not_active Ceased
- 2008-05-15 EA EA200971069A patent/EA200971069A1/ru unknown
- 2008-05-15 CN CN200880016466A patent/CN101679330A/zh active Pending
- 2008-05-15 JP JP2010508911A patent/JP5406827B2/ja active Active
- 2008-05-15 CA CA2684149A patent/CA2684149C/en not_active Expired - Fee Related
- 2008-05-15 BR BRPI0811744-6A2A patent/BRPI0811744A2/pt not_active IP Right Cessation
- 2008-05-15 MX MX2009012371A patent/MX2009012371A/es not_active Application Discontinuation
- 2008-05-15 EP EP08750836A patent/EP2155707B1/en active Active
- 2008-05-15 US US12/600,826 patent/US8765765B2/en active Active
- 2008-05-15 AU AU2008252619A patent/AU2008252619A1/en not_active Abandoned
- 2008-05-15 MY MYPI20094707 patent/MY150784A/en unknown
- 2008-05-15 GE GEAP200811607A patent/GEP20125523B/en unknown
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- 2009-10-15 IL IL201534A patent/IL201534A0/en unknown
- 2009-10-22 ZA ZA200907425A patent/ZA200907425B/xx unknown
- 2009-10-30 TN TNP2009000459A patent/TN2009000459A1/fr unknown
- 2009-11-09 NI NI200900202A patent/NI200900202A/es unknown
- 2009-11-17 CU CU2009000196A patent/CU23852B1/es not_active IP Right Cessation
- 2009-12-07 MA MA32403A patent/MA31432B1/fr unknown
- 2009-12-16 CO CO09144002A patent/CO6251252A2/es not_active Application Discontinuation
- 2009-12-18 EC EC2009009819A patent/ECSP099819A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ580646A (en) | 2012-03-30 |
| JP5406827B2 (ja) | 2014-02-05 |
| EA200971069A1 (ru) | 2010-04-30 |
| EP2155707B1 (en) | 2013-03-13 |
| HU0700353D0 (en) | 2007-07-30 |
| TW201002324A (en) | 2010-01-16 |
| GEP20125523B (en) | 2012-05-25 |
| BRPI0811744A2 (pt) | 2014-11-11 |
| CN101679330A (zh) | 2010-03-24 |
| TN2009000459A1 (en) | 2011-03-31 |
| JP2010527983A (ja) | 2010-08-19 |
| ECSP099819A (es) | 2010-03-31 |
| CU23852B1 (es) | 2012-10-15 |
| CA2684149C (en) | 2012-12-04 |
| MY150784A (en) | 2014-02-28 |
| MX2009012371A (es) | 2009-12-03 |
| MA31432B1 (fr) | 2010-06-01 |
| US8765765B2 (en) | 2014-07-01 |
| NI200900202A (es) | 2010-03-11 |
| CU20090196A7 (es) | 2011-07-11 |
| AP2009005011A0 (en) | 2009-10-31 |
| CO6251252A2 (es) | 2011-02-21 |
| WO2008142461A1 (en) | 2008-11-27 |
| EP2155707A1 (en) | 2010-02-24 |
| US20100137335A1 (en) | 2010-06-03 |
| ZA200907425B (en) | 2010-07-28 |
| AU2008252619A1 (en) | 2008-11-27 |
| CA2684149A1 (en) | 2008-11-27 |
| IL201534A0 (en) | 2010-05-31 |
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