JP5650637B2 - （ヘテロ−）アリール−シクロヘキサン誘導体 - Google Patents
（ヘテロ−）アリール−シクロヘキサン誘導体 Download PDFInfo
- Publication number
- JP5650637B2 JP5650637B2 JP2011501139A JP2011501139A JP5650637B2 JP 5650637 B2 JP5650637 B2 JP 5650637B2 JP 2011501139 A JP2011501139 A JP 2011501139A JP 2011501139 A JP2011501139 A JP 2011501139A JP 5650637 B2 JP5650637 B2 JP 5650637B2
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- JP
- Japan
- Prior art keywords
- indol
- methyl
- butyl
- dimethyl
- ethyl
- 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.)
- Expired - Fee Related
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- 150000001875 compounds Chemical class 0.000 claims description 157
- -1 3,4- dihydro -1H- isoquinoline 2-yl Chemical group 0.000 claims description 81
- 125000003118 aryl group Chemical group 0.000 claims description 64
- 239000000203 mixture Substances 0.000 claims description 61
- 125000001424 substituent group Chemical group 0.000 claims description 46
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 239000003814 drug Substances 0.000 claims description 25
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 23
- 229920006395 saturated elastomer Polymers 0.000 claims description 22
- 208000002193 Pain Diseases 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 14
- 238000007792 addition Methods 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- IKMCGLBRZOQHPZ-UHFFFAOYSA-N 1-butyl-4,4-bis(5-fluoro-3-methyl-1h-indol-2-yl)-n,n-dimethylcyclohexan-1-amine Chemical compound C1CC(CCCC)(N(C)C)CCC1(C1=C(C2=CC(F)=CC=C2N1)C)C1=C(C)C2=CC(F)=CC=C2N1 IKMCGLBRZOQHPZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- IPOCNSUALLUPCK-UHFFFAOYSA-N n,n-dimethyl-4,4-bis[3-(2-pyridin-4-ylethyl)-1h-indol-2-yl]-1-thiophen-2-ylcyclohexan-1-amine Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1(C1=C(C2=CC=CC=C2N1)CCC=1C=CN=CC=1)C=1NC2=CC=CC=C2C=1CCC1=CC=NC=C1 IPOCNSUALLUPCK-UHFFFAOYSA-N 0.000 claims description 8
- IYESVYAQQBUTRX-UHFFFAOYSA-N n,n-dimethyl-4-(3-methyl-1h-indol-2-yl)-1-phenyl-4-thiophen-2-ylcyclohexan-1-amine Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1(C1=C(C2=CC=CC=C2N1)C)C1=CC=CS1 IYESVYAQQBUTRX-UHFFFAOYSA-N 0.000 claims description 8
- FJWBGXNSRIFCBK-UHFFFAOYSA-N n-methyl-1-phenyl-4,4-bis[3-(2-pyridin-4-ylethyl)-1h-indol-2-yl]cyclohexan-1-amine Chemical compound C1CC(NC)(C=2C=CC=CC=2)CCC1(C1=C(C2=CC=CC=C2N1)CCC=1C=CN=CC=1)C=1NC2=CC=CC=C2C=1CCC1=CC=NC=C1 FJWBGXNSRIFCBK-UHFFFAOYSA-N 0.000 claims description 8
- WSCQZQRYQBQGLM-UHFFFAOYSA-N 1-butyl-n,n-dimethyl-4,4-bis(3-methyl-1h-indol-2-yl)cyclohexan-1-amine Chemical compound C1CC(CCCC)(N(C)C)CCC1(C1=C(C2=CC=CC=C2N1)C)C1=C(C)C2=CC=CC=C2N1 WSCQZQRYQBQGLM-UHFFFAOYSA-N 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- LEUQQELOTXEJAG-UHFFFAOYSA-N 1-(3-fluorophenyl)-n,n-dimethyl-4-(3-methyl-1h-indol-2-yl)-4-thiophen-2-ylcyclohexan-1-amine Chemical compound C1CC(N(C)C)(C=2C=C(F)C=CC=2)CCC1(C1=C(C2=CC=CC=C2N1)C)C1=CC=CS1 LEUQQELOTXEJAG-UHFFFAOYSA-N 0.000 claims description 5
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- DBIAXUQJDZDFDY-UHFFFAOYSA-N n,n-dimethyl-4-(3-methyl-1h-indol-2-yl)-1,4-diphenylcyclohexan-1-amine Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1(C1=C(C2=CC=CC=C2N1)C)C1=CC=CC=C1 DBIAXUQJDZDFDY-UHFFFAOYSA-N 0.000 claims description 5
- MYCMSFYLBALJSR-UHFFFAOYSA-N 1-benzyl-n,n-dimethyl-4,4-bis[3-(2-pyridin-4-ylethyl)-1h-indol-2-yl]cyclohexan-1-amine Chemical compound C1CC(C2=C(C3=CC=CC=C3N2)CCC=2C=CN=CC=2)(C2=C(C3=CC=CC=C3N2)CCC=2C=CN=CC=2)CCC1(N(C)C)CC1=CC=CC=C1 MYCMSFYLBALJSR-UHFFFAOYSA-N 0.000 claims description 4
- LKTYBGSDBHRPMR-UHFFFAOYSA-N 1-butyl-n,n-dimethyl-4,4-bis[3-(2-pyridin-4-ylethyl)-1h-indol-2-yl]cyclohexan-1-amine Chemical compound C1CC(CCCC)(N(C)C)CCC1(C1=C(C2=CC=CC=C2N1)CCC=1C=CN=CC=1)C1=C(CCC=2C=CN=CC=2)C2=CC=CC=C2N1 LKTYBGSDBHRPMR-UHFFFAOYSA-N 0.000 claims description 4
- IZWDLGKGBTTWEK-UHFFFAOYSA-N 2-[2-[2-[4-butyl-4-(dimethylamino)-1-(3-methyl-1h-indol-2-yl)cyclohexyl]-1h-indol-3-yl]ethyl]isoindole-1,3-dione Chemical compound C1CC(CCCC)(N(C)C)CCC1(C1=C(C2=CC=CC=C2N1)CCN1C(C2=CC=CC=C2C1=O)=O)C1=C(C)C2=CC=CC=C2N1 IZWDLGKGBTTWEK-UHFFFAOYSA-N 0.000 claims description 4
- CLQBMEKBDZXMBN-UHFFFAOYSA-N 4-[3-(2-aminoethyl)-1h-indol-2-yl]-1-butyl-n,n-dimethyl-4-(3-methyl-1h-indol-2-yl)cyclohexan-1-amine Chemical compound C1CC(CCCC)(N(C)C)CCC1(C1=C(C2=CC=CC=C2N1)CCN)C1=C(C)C2=CC=CC=C2N1 CLQBMEKBDZXMBN-UHFFFAOYSA-N 0.000 claims description 4
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- BRZCUAIWRASXAR-UHFFFAOYSA-N n,n-dimethyl-4,4-bis(3-methyl-1-benzofuran-2-yl)-1-phenylcyclohexan-1-amine Chemical compound C1CC(C2=C(C3=CC=CC=C3O2)C)(C2=C(C3=CC=CC=C3O2)C)CCC1(N(C)C)C1=CC=CC=C1 BRZCUAIWRASXAR-UHFFFAOYSA-N 0.000 claims description 4
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- YFXBMXXXKCCOIV-UHFFFAOYSA-N 1-butyl-4,4-bis(1,3-dimethylindol-2-yl)-n,n-dimethylcyclohexan-1-amine Chemical compound C1CC(CCCC)(N(C)C)CCC1(C=1N(C2=CC=CC=C2C=1C)C)C1=C(C)C2=CC=CC=C2N1C YFXBMXXXKCCOIV-UHFFFAOYSA-N 0.000 claims description 3
- NOHFAXTYQMYOOD-UHFFFAOYSA-N 1-butyl-4-(1,3-dimethylindol-2-yl)-n,n-dimethyl-4-(3-methyl-1h-indol-2-yl)cyclohexan-1-amine Chemical compound C1CC(CCCC)(N(C)C)CCC1(C=1N(C2=CC=CC=C2C=1C)C)C1=C(C)C2=CC=CC=C2N1 NOHFAXTYQMYOOD-UHFFFAOYSA-N 0.000 claims description 3
- VWZRJNFNKIZQDS-UHFFFAOYSA-N 1-butyl-n,n-dimethyl-4,4-bis[3-methyl-5-(trifluoromethyl)-1h-indol-2-yl]cyclohexan-1-amine Chemical compound C1CC(CCCC)(N(C)C)CCC1(C1=C(C2=CC(=CC=C2N1)C(F)(F)F)C)C1=C(C)C2=CC(C(F)(F)F)=CC=C2N1 VWZRJNFNKIZQDS-UHFFFAOYSA-N 0.000 claims description 3
- CBISQFFYOFELJO-UHFFFAOYSA-N 2-[4-butyl-1-[3-(2-pyridin-4-ylethyl)-1h-indol-2-yl]-4-pyrrolidin-1-ylcyclohexyl]-3-(2-pyridin-4-ylethyl)-1h-indole Chemical compound C1CC(CCCC)(N2CCCC2)CCC1(C1=C(C2=CC=CC=C2N1)CCC=1C=CN=CC=1)C=1NC2=CC=CC=C2C=1CCC1=CC=NC=C1 CBISQFFYOFELJO-UHFFFAOYSA-N 0.000 claims description 3
- ZIQYOEDFEFSRQJ-UHFFFAOYSA-N 4-(3-methoxyphenyl)-n,n-dimethyl-4-(3-methyl-1h-indol-2-yl)-1-phenylcyclohexan-1-amine Chemical compound COC1=CC=CC(C2(CCC(CC2)(N(C)C)C=2C=CC=CC=2)C2=C(C3=CC=CC=C3N2)C)=C1 ZIQYOEDFEFSRQJ-UHFFFAOYSA-N 0.000 claims description 3
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- UIWRWOAJDRHUIH-UHFFFAOYSA-N 1-[2-[2-[4-butyl-4-(dimethylamino)-1-(3-methyl-1h-indol-2-yl)cyclohexyl]-1h-indol-3-yl]ethyl]-3-phenylurea Chemical compound C1CC(CCCC)(N(C)C)CCC1(C1=C(C2=CC=CC=C2N1)CCNC(=O)NC=1C=CC=CC=1)C1=C(C)C2=CC=CC=C2N1 UIWRWOAJDRHUIH-UHFFFAOYSA-N 0.000 claims description 2
- HIIRPBXAWXPDIH-UHFFFAOYSA-N 1-[2-[2-[4-butyl-4-(dimethylamino)-1-(5-fluoro-3-methyl-1h-indol-2-yl)cyclohexyl]-1h-indol-3-yl]ethyl]-3-phenylurea Chemical compound C1CC(CCCC)(N(C)C)CCC1(C1=C(C2=CC=CC=C2N1)CCNC(=O)NC=1C=CC=CC=1)C1=C(C)C2=CC(F)=CC=C2N1 HIIRPBXAWXPDIH-UHFFFAOYSA-N 0.000 claims description 2
- IPDAUJTVWRMFKT-UHFFFAOYSA-N 1-benzyl-n,n-dimethyl-4-(3-methyl-1h-indol-2-yl)-4-thiophen-2-ylcyclohexan-1-amine Chemical compound C1CC(C2=C(C3=CC=CC=C3N2)C)(C=2SC=CC=2)CCC1(N(C)C)CC1=CC=CC=C1 IPDAUJTVWRMFKT-UHFFFAOYSA-N 0.000 claims description 2
- KDQMUHLWMMPREV-UHFFFAOYSA-N 1-butyl-4,4-bis[3-[2-(3,4-dihydro-1h-isoquinolin-2-yl)ethyl]-1h-indol-2-yl]-n,n-dimethylcyclohexan-1-amine Chemical compound C1CC(CCCC)(N(C)C)CCC1(C1=C(C2=CC=CC=C2N1)CCN1CC2=CC=CC=C2CC1)C1=C(CCN2CC3=CC=CC=C3CC2)C2=CC=CC=C2N1 KDQMUHLWMMPREV-UHFFFAOYSA-N 0.000 claims description 2
- HUZILLSKENSLEU-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-n,n-dimethyl-4-(3-methyl-1h-indol-2-yl)-1-phenylcyclohexan-1-amine Chemical compound C1CC(C=2C=C3OCOC3=CC=2)(C2=C(C3=CC=CC=C3N2)C)CCC1(N(C)C)C1=CC=CC=C1 HUZILLSKENSLEU-UHFFFAOYSA-N 0.000 claims description 2
- FIQQPFFLTHVIBR-UHFFFAOYSA-N 4-(4-methoxyphenyl)-n,n-dimethyl-4-(3-methyl-1h-indol-2-yl)-1-phenylcyclohexan-1-amine Chemical compound C1=CC(OC)=CC=C1C1(C2=C(C3=CC=CC=C3N2)C)CCC(C=2C=CC=CC=2)(N(C)C)CC1 FIQQPFFLTHVIBR-UHFFFAOYSA-N 0.000 claims description 2
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing alicyclic rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Anesthesiology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Rheumatology (AREA)
- Reproductive Health (AREA)
- Child & Adolescent Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Nutrition Science (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Gynecology & Obstetrics (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08005797.9 | 2008-03-27 | ||
| EP08005797 | 2008-03-27 | ||
| PCT/EP2009/002172 WO2009118163A1 (de) | 2008-03-27 | 2009-03-25 | (hetero-)aryl-cyclohexan-derivate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011515429A JP2011515429A (ja) | 2011-05-19 |
| JP2011515429A5 JP2011515429A5 (enExample) | 2014-05-22 |
| JP5650637B2 true JP5650637B2 (ja) | 2015-01-07 |
Family
ID=39671382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011501139A Expired - Fee Related JP5650637B2 (ja) | 2008-03-27 | 2009-03-25 | （ヘテロ−）アリール−シクロヘキサン誘導体 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7977370B2 (enExample) |
| EP (1) | EP2280941B1 (enExample) |
| JP (1) | JP5650637B2 (enExample) |
| CN (1) | CN102046597B (enExample) |
| AR (1) | AR071066A1 (enExample) |
| AU (1) | AU2009228637B2 (enExample) |
| CA (1) | CA2718209A1 (enExample) |
| CL (1) | CL2009000733A1 (enExample) |
| ES (1) | ES2544488T3 (enExample) |
| HU (1) | HUE026184T2 (enExample) |
| IL (1) | IL208137A (enExample) |
| MX (1) | MX2010010446A (enExample) |
| PE (1) | PE20091657A1 (enExample) |
| PL (1) | PL2280941T3 (enExample) |
| RU (1) | RU2502733C2 (enExample) |
| WO (1) | WO2009118163A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009118163A1 (de) | 2008-03-27 | 2009-10-01 | Grünenthal GmbH | (hetero-)aryl-cyclohexan-derivate |
| PL2271613T3 (pl) | 2008-03-27 | 2014-09-30 | Gruenenthal Gmbh | Hydroksymetylocykloheksyloaminy |
| AR071067A1 (es) | 2008-03-27 | 2010-05-26 | Gruenenthal Chemie | Ciclohexildiaminas sustituidas |
| PT2260042E (pt) | 2008-03-27 | 2011-12-06 | Gruenenthal Gmbh | Derivados de ciclo-hexano espirocíclicos substituídos |
| CA2719736C (en) | 2008-03-27 | 2016-02-09 | Gruenenthal Gmbh | Spiro(5.5)undecane derivatives |
| EP2502907B1 (de) | 2008-03-27 | 2018-08-29 | Grünenthal GmbH | Substituierte 4-Aminocyclohexan-Derivate |
Family Cites Families (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4065573A (en) | 1976-06-03 | 1977-12-27 | The Upjohn Company | 4-Amino-4-phenylcyclohexanone ketal compositions and process of use |
| US4115589A (en) | 1977-05-17 | 1978-09-19 | The Upjohn Company | Compounds, compositions and method of use |
| US4366172A (en) | 1977-09-29 | 1982-12-28 | The Upjohn Company | 4-Amino-cyclohexanols, their pharmaceutical compositions and methods of use |
| US4239780A (en) * | 1979-10-11 | 1980-12-16 | The Upjohn Company | Phospholipase A2 inhibition |
| DE19830105C1 (de) * | 1998-07-06 | 2000-02-17 | Gruenenthal Gmbh | Acridinderivate |
| US6632836B1 (en) * | 1998-10-30 | 2003-10-14 | Merck & Co., Inc. | Carbocyclic potassium channel inhibitors |
| US6600015B2 (en) * | 2000-04-04 | 2003-07-29 | Hoffmann-La Roche Inc. | Selective linear peptides with melanocortin-4 receptor (MC4-R) agonist activity |
| GB0012240D0 (en) | 2000-05-19 | 2000-07-12 | Merck Sharp & Dohme | Therapeutic agents |
| RU2239642C1 (ru) * | 2000-08-30 | 2004-11-10 | Ф.Хоффманн-Ля Рош Аг | Селективные циклопептиды |
| DE10123163A1 (de) | 2001-05-09 | 2003-01-16 | Gruenenthal Gmbh | Substituierte Cyclohexan-1,4-diaminderivate |
| PE20030320A1 (es) * | 2001-07-17 | 2003-04-03 | Gruenenthal Chemie | Derivados sustituidos de 4-aminociclohexanol |
| DE10135636A1 (de) | 2001-07-17 | 2003-02-06 | Gruenenthal Gmbh | Substituierte 4-Aminocyclohexanole |
| IL159317A0 (en) | 2001-07-18 | 2004-06-01 | Dipiemme Dies And Plastic Mach | A corrugated/undulated sheet having protuberances in the grooves defined by the corrugations, process and apparatus |
| DE10213051B4 (de) | 2002-03-23 | 2013-03-07 | Grünenthal GmbH | Substituierte 4-Aminocyclohexanole |
| DE10252650A1 (de) | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Cyclohexyl-Harnstoff-Derivate |
| DE10252667A1 (de) | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE10252665A1 (de) | 2002-11-11 | 2004-06-03 | Grünenthal GmbH | 4-Aminomethyl-1-aryl-cyclohexylamin-Derivate |
| DE10252666A1 (de) | 2002-11-11 | 2004-08-05 | Grünenthal GmbH | N-Piperidyl-cyclohexan-Derivate |
| ES2279195T3 (es) | 2002-11-12 | 2007-08-16 | Grunenthal Gmbh | Derivados de 4-alquil/4-alquenil/4-alquenilmetil/-1-arilciclohexilamina. |
| WO2004043902A1 (de) | 2002-11-12 | 2004-05-27 | Grünenthal GmbH | 4-hydroxymethyl-1-aryl-cyclohexylamin-derivative |
| DE10360792A1 (de) | 2003-12-23 | 2005-07-28 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE10360793A1 (de) | 2003-12-23 | 2005-07-28 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102004023508A1 (de) | 2004-05-10 | 2005-12-08 | Grünenthal GmbH | Säurederivate substituierter Cyclohexyl-1,4-diamine |
| DE102004023507A1 (de) | 2004-05-10 | 2005-12-01 | Grünenthal GmbH | Substituierte Cyclohexylessigsäure-Derivate |
| DE102004023635A1 (de) | 2004-05-10 | 2006-04-13 | Grünenthal GmbH | Heteroarylsubstituierte Cyclohexyl-1,4-diamin-Derivate |
| DE102004023632A1 (de) | 2004-05-10 | 2005-12-08 | Grünenthal GmbH | Substituierte Cyclohexylcarbonsäure-Derivate |
| DE102004023522A1 (de) | 2004-05-10 | 2005-12-01 | Grünenthal GmbH | Substituierte Cyclohexyl-1,4-diamin-Derivate |
| DE102004023501A1 (de) | 2004-05-10 | 2005-12-01 | Grünenthal GmbH | Oxosubstituierte Cyclohexyl-1,4-diamin-Derivate |
| DE102004023506A1 (de) | 2004-05-10 | 2005-12-01 | Grünenthal GmbH | Kettenverlängerte substituierte Cyclohexyl-1,4-diamin-Derivate |
| DE102004039382A1 (de) | 2004-08-13 | 2006-02-23 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102005016460A1 (de) | 2005-04-11 | 2006-10-19 | Grünenthal GmbH | Spriocyclische Cyclohexanderivate zur Behandlung von Substanzabhängigkeit |
| DE102005061427A1 (de) | 2005-12-22 | 2007-06-28 | Grünenthal GmbH | Substituierte Oxadiazol-Derivate |
| DE102005061429A1 (de) | 2005-12-22 | 2007-06-28 | Grünenthal GmbH | Substituierte Oxazol-Derivate |
| DE102005061430A1 (de) | 2005-12-22 | 2007-07-05 | Grünenthal GmbH | Substituierte Imidazolin-Derivate |
| DE102005061428A1 (de) | 2005-12-22 | 2007-08-16 | Grünenthal GmbH | Substituierte Cyclohexylmethyl-Derivate |
| DE102006019597A1 (de) | 2006-04-27 | 2007-10-31 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| FR2902695B1 (fr) * | 2006-06-26 | 2009-11-20 | Packaging Partner | Etiquette d'information inviolable |
| DE102006033109A1 (de) * | 2006-07-18 | 2008-01-31 | Grünenthal GmbH | Substituierte Heteroaryl-Derivate |
| DE102006033114A1 (de) * | 2006-07-18 | 2008-01-24 | Grünenthal GmbH | Spirocyclische Azaindol-Derivate |
| CN101610761A (zh) * | 2006-12-22 | 2009-12-23 | 诺瓦提斯公司 | 作为ddp-iv抑制剂的1-氨基甲基-l-苯基-环己烷衍生物 |
| EP2179104A4 (en) | 2007-07-13 | 2012-01-18 | Tinnerman Palnut Engineered Products | SEAM CLAMP WITH HEAT LOCK |
| CA2719736C (en) | 2008-03-27 | 2016-02-09 | Gruenenthal Gmbh | Spiro(5.5)undecane derivatives |
| PL2271613T3 (pl) | 2008-03-27 | 2014-09-30 | Gruenenthal Gmbh | Hydroksymetylocykloheksyloaminy |
| EP2502907B1 (de) | 2008-03-27 | 2018-08-29 | Grünenthal GmbH | Substituierte 4-Aminocyclohexan-Derivate |
| AR071067A1 (es) | 2008-03-27 | 2010-05-26 | Gruenenthal Chemie | Ciclohexildiaminas sustituidas |
| WO2009118163A1 (de) | 2008-03-27 | 2009-10-01 | Grünenthal GmbH | (hetero-)aryl-cyclohexan-derivate |
| PT2260042E (pt) | 2008-03-27 | 2011-12-06 | Gruenenthal Gmbh | Derivados de ciclo-hexano espirocíclicos substituídos |
-
2009
- 2009-03-25 WO PCT/EP2009/002172 patent/WO2009118163A1/de not_active Ceased
- 2009-03-25 PL PL09725704T patent/PL2280941T3/pl unknown
- 2009-03-25 AR ARP090101056A patent/AR071066A1/es unknown
- 2009-03-25 CA CA2718209A patent/CA2718209A1/en not_active Abandoned
- 2009-03-25 ES ES09725704.2T patent/ES2544488T3/es active Active
- 2009-03-25 JP JP2011501139A patent/JP5650637B2/ja not_active Expired - Fee Related
- 2009-03-25 MX MX2010010446A patent/MX2010010446A/es active IP Right Grant
- 2009-03-25 US US12/410,692 patent/US7977370B2/en not_active Expired - Fee Related
- 2009-03-25 RU RU2010143451/04A patent/RU2502733C2/ru not_active IP Right Cessation
- 2009-03-25 EP EP20090725704 patent/EP2280941B1/de not_active Not-in-force
- 2009-03-25 CL CL2009000733A patent/CL2009000733A1/es unknown
- 2009-03-25 AU AU2009228637A patent/AU2009228637B2/en not_active Ceased
- 2009-03-25 CN CN2009801201880A patent/CN102046597B/zh not_active Expired - Fee Related
- 2009-03-25 PE PE2009000444A patent/PE20091657A1/es not_active Application Discontinuation
- 2009-03-25 HU HUE09725704A patent/HUE026184T2/en unknown
-
2010
- 2010-09-14 IL IL208137A patent/IL208137A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| RU2502733C2 (ru) | 2013-12-27 |
| CN102046597B (zh) | 2013-09-11 |
| AU2009228637A1 (en) | 2009-10-01 |
| CN102046597A (zh) | 2011-05-04 |
| HK1153744A1 (zh) | 2012-04-05 |
| US7977370B2 (en) | 2011-07-12 |
| ES2544488T3 (es) | 2015-08-31 |
| WO2009118163A1 (de) | 2009-10-01 |
| US20090247573A1 (en) | 2009-10-01 |
| AR071066A1 (es) | 2010-05-26 |
| PE20091657A1 (es) | 2009-11-07 |
| EP2280941A1 (de) | 2011-02-09 |
| CL2009000733A1 (es) | 2009-05-15 |
| IL208137A (en) | 2015-10-29 |
| IL208137A0 (en) | 2010-12-30 |
| EP2280941B1 (de) | 2015-05-06 |
| PL2280941T3 (pl) | 2015-10-30 |
| MX2010010446A (es) | 2010-11-05 |
| CA2718209A1 (en) | 2009-10-01 |
| RU2010143451A (ru) | 2012-05-10 |
| AU2009228637B2 (en) | 2013-12-19 |
| HUE026184T2 (en) | 2016-05-30 |
| JP2011515429A (ja) | 2011-05-19 |
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