CA2566212C - Heteroaryl-substituted cyclohexyl-1,4-diamine derivatives - Google Patents
Heteroaryl-substituted cyclohexyl-1,4-diamine derivatives Download PDFInfo
- Publication number
- CA2566212C CA2566212C CA2566212A CA2566212A CA2566212C CA 2566212 C CA2566212 C CA 2566212C CA 2566212 A CA2566212 A CA 2566212A CA 2566212 A CA2566212 A CA 2566212A CA 2566212 C CA2566212 C CA 2566212C
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- CA
- Canada
- Prior art keywords
- cyclohexyl
- unsubstituted
- singly
- multiply substituted
- dimethylamino
- Prior art date
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- 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 71
- 125000000217 alkyl group Chemical group 0.000 claims description 62
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- 125000003118 aryl group Chemical group 0.000 claims description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 125000001544 thienyl group Chemical group 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 24
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000004076 pyridyl group Chemical group 0.000 claims description 21
- 125000002541 furyl group Chemical group 0.000 claims description 20
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- 238000000034 method Methods 0.000 claims description 16
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 15
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 15
- 125000001041 indolyl group Chemical group 0.000 claims description 15
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 15
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 150000001768 cations Chemical class 0.000 claims description 14
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 13
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- 125000001624 naphthyl group Chemical group 0.000 claims description 13
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 12
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- 238000002360 preparation method Methods 0.000 claims description 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 11
- OYAHUAHATRUQAN-UHFFFAOYSA-N 5-benzylfuran-2-carboxylic acid Chemical compound O1C(C(=O)O)=CC=C1CC1=CC=CC=C1 OYAHUAHATRUQAN-UHFFFAOYSA-N 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 10
- UVEPOHNXGXVOJE-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl UVEPOHNXGXVOJE-UHFFFAOYSA-N 0.000 claims description 9
- 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 claims description 9
- 230000003444 anaesthetic effect Effects 0.000 claims description 9
- 125000001425 triazolyl group Chemical group 0.000 claims description 9
- ULPDNBMMJNDUDU-UHFFFAOYSA-N 1-(3-fluorophenyl)-1-n,1-n-dimethylcyclohexane-1,4-diamine Chemical compound C=1C=CC(F)=CC=1C1(N(C)C)CCC(N)CC1 ULPDNBMMJNDUDU-UHFFFAOYSA-N 0.000 claims description 8
- 208000000094 Chronic Pain Diseases 0.000 claims description 8
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 8
- 125000002883 imidazolyl group Chemical group 0.000 claims description 8
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 7
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 238000006467 substitution reaction Methods 0.000 claims description 7
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
- WQXUUMUOERZZAE-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=C(C)ON=C1C1=C(Cl)C=CC=C1Cl WQXUUMUOERZZAE-UHFFFAOYSA-N 0.000 claims description 6
- PNHDBTFERQRLFF-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-n-[4-(dimethylamino)-4-phenylcyclohexyl]-5-methyl-1,2-oxazole-4-carboxamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)C1=C(C)ON=C1C1=C(Cl)C=CC=C1Cl PNHDBTFERQRLFF-UHFFFAOYSA-N 0.000 claims description 6
- GQYQHAGPALBYDO-UHFFFAOYSA-N 5-methyl-2-phenyltriazole-4-carboxylic acid Chemical compound N1=C(C(O)=O)C(C)=NN1C1=CC=CC=C1 GQYQHAGPALBYDO-UHFFFAOYSA-N 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- NEQKPPPNGCSPKM-UHFFFAOYSA-N n-[4-(dimethylamino)-4-phenylcyclohexyl]-5-methyl-2-phenyltriazole-4-carboxamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)C(C(=N1)C)=NN1C1=CC=CC=C1 NEQKPPPNGCSPKM-UHFFFAOYSA-N 0.000 claims description 6
- GMTTVNZMLYFSKB-UHFFFAOYSA-N n-[4-(dimethylamino)-4-phenylcyclohexyl]-5-methyl-3-phenyl-1,2-oxazole-4-carboxamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)C1=C(C)ON=C1C1=CC=CC=C1 GMTTVNZMLYFSKB-UHFFFAOYSA-N 0.000 claims description 6
- KVRGHMFZWJMOBY-UHFFFAOYSA-N 1-n,1-n-dimethyl-1-phenylcyclohexane-1,4-diamine Chemical compound C=1C=CC=CC=1C1(N(C)C)CCC(N)CC1 KVRGHMFZWJMOBY-UHFFFAOYSA-N 0.000 claims description 5
- ULRRQOVBQQHAGW-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-n-[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexyl]-5-methyl-1,2-oxazole-4-carboxamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=C(F)C=CC=2)CCC1NC(=O)C1=C(C)ON=C1C1=C(Cl)C=CC=C1Cl ULRRQOVBQQHAGW-UHFFFAOYSA-N 0.000 claims description 5
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- 125000004306 triazinyl group Chemical group 0.000 claims description 5
- YNYQLSWAEDJSQG-UHFFFAOYSA-N 1-benzyl-1-n,1-n-dimethylcyclohexane-1,4-diamine Chemical compound C=1C=CC=CC=1CC1(N(C)C)CCC(N)CC1 YNYQLSWAEDJSQG-UHFFFAOYSA-N 0.000 claims description 4
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- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 4
- 239000012964 benzotriazole Substances 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 238000011260 co-administration Methods 0.000 claims description 4
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical class NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 claims description 4
- 239000003158 myorelaxant agent Substances 0.000 claims description 4
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- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
- KYSPBJFLKSGJKV-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-1-N,1-N-dimethylcyclohexane-1,4-diamine Chemical compound C=1C=CC=C(Cl)C=1CC1(N(C)C)CCC(N)CC1 KYSPBJFLKSGJKV-UHFFFAOYSA-N 0.000 claims description 3
- SLDCHYOUPRGBFC-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]-1-n,1-n-dimethylcyclohexane-1,4-diamine Chemical compound C=1C=C(F)C=CC=1CC1(N(C)C)CCC(N)CC1 SLDCHYOUPRGBFC-UHFFFAOYSA-N 0.000 claims description 3
- NLTSWRZBSRBUIM-UHFFFAOYSA-N 1-n,1-n-dimethyl-1-(2-phenylethyl)cyclohexane-1,4-diamine Chemical compound C=1C=CC=CC=1CCC1(N(C)C)CCC(N)CC1 NLTSWRZBSRBUIM-UHFFFAOYSA-N 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
- LBXYKBUIYDYHPX-UHFFFAOYSA-N 4-benzyl-4-piperidin-1-ylcyclohexan-1-amine Chemical compound C1CC(N)CCC1(N1CCCCC1)CC1=CC=CC=C1 LBXYKBUIYDYHPX-UHFFFAOYSA-N 0.000 claims description 3
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- 239000000654 additive Substances 0.000 claims description 3
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 3
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- CMTQSZXRNODKFL-UHFFFAOYSA-N n-[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexyl]-5-methyl-3-phenyl-1,2-oxazole-4-carboxamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=C(F)C=CC=2)CCC1NC(=O)C1=C(C)ON=C1C1=CC=CC=C1 CMTQSZXRNODKFL-UHFFFAOYSA-N 0.000 claims description 3
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 2
- YWRFNCQADWKNBE-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexyl]-5-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C1CC(N(C)C)(C=2C=C(F)C=CC=2)CCC1NC(=O)C(=C1C(F)(F)F)C=NN1C1=CC=C(Cl)C=C1 YWRFNCQADWKNBE-UHFFFAOYSA-N 0.000 claims description 2
- RHTWGMJQYALVNH-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-1-N,1-N-dimethylcyclohexane-1,4-diamine Chemical compound C=1C=C(Cl)C=CC=1CC1(N(C)C)CCC(N)CC1 RHTWGMJQYALVNH-UHFFFAOYSA-N 0.000 claims description 2
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical class C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 claims description 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 2
- UUVDFAXMHYMJNL-UHFFFAOYSA-N 2-phenoxy-n-(4-phenyl-4-piperidin-1-ylcyclohexyl)pyridine-3-carboxamide Chemical compound C=1C=CN=C(OC=2C=CC=CC=2)C=1C(=O)NC(CC1)CCC1(C=1C=CC=CC=1)N1CCCCC1 UUVDFAXMHYMJNL-UHFFFAOYSA-N 0.000 claims description 2
- KYVCOIIOIVPHAS-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexyl]-5-methyl-1,2-oxazole-4-carboxamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=C(F)C=CC=2)CCC1NC(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl KYVCOIIOIVPHAS-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims description 2
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- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
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- SUQZEIQIYOVESE-UHFFFAOYSA-N n-[4-(azepan-1-yl)-4-benzylcyclohexyl]-3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound CC=1ON=C(C=2C(=CC=CC=2)Cl)C=1C(=O)NC(CC1)CCC1(N1CCCCCC1)CC1=CC=CC=C1 SUQZEIQIYOVESE-UHFFFAOYSA-N 0.000 claims description 2
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- APAXFCQETLIMMG-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-2-phenoxypyridine-3-carboxamide Chemical compound C1CC(NC(=O)C=2C(=NC=CC=2)OC=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=C(C)C=C1 APAXFCQETLIMMG-UHFFFAOYSA-N 0.000 claims description 2
- FXMSDDBBUQKPDX-UHFFFAOYSA-N n-[4-(dimethylamino)-4-phenylcyclohexyl]-5-methyl-2-phenyltriazole-4-carboxamide Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)C(C(=N1)C)=NN1C1=CC=CC=C1 FXMSDDBBUQKPDX-UHFFFAOYSA-N 0.000 claims description 2
- DMVVUGYSBUVLBQ-UHFFFAOYSA-N n-[4-benzyl-4-(dimethylamino)cyclohexyl]-2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)acetamide Chemical compound C1CC(NC(=O)CC2=C(SC(=N2)C=2C=CC=CC=2)C)CCC1(N(C)C)CC1=CC=CC=C1 DMVVUGYSBUVLBQ-UHFFFAOYSA-N 0.000 claims description 2
- WTOILTVNVLXNIG-UHFFFAOYSA-N n-[4-benzyl-4-(dimethylamino)cyclohexyl]-5-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]thiophene-2-carboxamide Chemical compound C1CC(NC(=O)C=2SC(=CC=2)C2=NN(C)C(=C2)C(F)(F)F)CCC1(N(C)C)CC1=CC=CC=C1 WTOILTVNVLXNIG-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- JIJDNEMHEBVVLG-UHFFFAOYSA-N 1-N,1-N-dimethyl-1-[(4-methylphenyl)methyl]cyclohexane-1,4-diamine Chemical compound C=1C=C(C)C=CC=1CC1(N(C)C)CCC(N)CC1 JIJDNEMHEBVVLG-UHFFFAOYSA-N 0.000 claims 4
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004023635A DE102004023635A1 (de) | 2004-05-10 | 2004-05-10 | Heteroarylsubstituierte Cyclohexyl-1,4-diamin-Derivate |
| DE102004023635.6 | 2004-05-10 | ||
| PCT/EP2005/004911 WO2005110971A1 (de) | 2004-05-10 | 2005-05-06 | Heteroarylsubstituierte cyclohexyl-1,4-diamin-derivate |
Publications (2)
| Publication Number | Publication Date |
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| CA2566212A1 CA2566212A1 (en) | 2005-11-24 |
| CA2566212C true CA2566212C (en) | 2013-06-18 |
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| Application Number | Title | Priority Date | Filing Date |
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| CA2566212A Expired - Fee Related CA2566212C (en) | 2004-05-10 | 2005-05-06 | Heteroaryl-substituted cyclohexyl-1,4-diamine derivatives |
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| US (1) | US8093272B2 (https=) |
| EP (1) | EP1745009B1 (https=) |
| JP (1) | JP4982357B2 (https=) |
| CA (1) | CA2566212C (https=) |
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| SI (1) | SI1745009T1 (https=) |
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| DE102004023635A1 (de) | 2004-05-10 | 2006-04-13 | Grünenthal GmbH | Heteroarylsubstituierte Cyclohexyl-1,4-diamin-Derivate |
| DE102004023506A1 (de) * | 2004-05-10 | 2005-12-01 | Grünenthal GmbH | Kettenverlängerte substituierte Cyclohexyl-1,4-diamin-Derivate |
| DE102005016170A1 (de) | 2005-04-07 | 2006-10-12 | Grünenthal GmbH | 4,5,6,7- Tetrahydro-isoxazolo(4,5c)pyridin-Verbindungen und deren Verwendung zur Herstellung von Arzneimitteln |
| EP1999114B1 (en) | 2006-03-22 | 2015-07-22 | F. Hoffmann-La Roche AG | Pyrazoles as 11-beta-hsd-1 |
| DE102006046745A1 (de) * | 2006-09-29 | 2008-04-03 | Grünenthal GmbH | Gemischte ORL1/µ-Agonisten zur Behandlung von Schmerz |
| ES2464102T3 (es) | 2008-03-27 | 2014-05-30 | Grünenthal GmbH | Derivados de 4-aminociclohexano sustituidos |
| EP2280941B1 (de) | 2008-03-27 | 2015-05-06 | Grünenthal GmbH | (hetero-)aryl-cyclohexan-derivate |
| ES2375543T3 (es) | 2008-03-27 | 2012-03-01 | Grünenthal GmbH | Derivados de espiro(5.5)undecano. |
| JP5529843B2 (ja) | 2008-03-27 | 2014-06-25 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 置換シクロヘキシルジアミン |
| AU2009228647B2 (en) | 2008-03-27 | 2013-07-04 | Grunenthal Gmbh | Substituted spirocyclic cyclohexane derivatives |
| CN102046591B (zh) | 2008-03-27 | 2014-12-03 | 格吕伦塔尔有限公司 | 羟甲基环己胺 |
| AR086113A1 (es) | 2011-04-30 | 2013-11-20 | Abbott Lab | Isoxazolinas como agentes terapeuticos |
| DE102011080986B4 (de) * | 2011-08-16 | 2014-02-13 | Mtu Friedrichshafen Gmbh | Steuereinrichtung für ein Einspritzsystem, Einspritzsystem mit einer Brennkraftmaschine und Notstromaggregat |
| EP2928471B1 (en) | 2012-12-06 | 2020-10-14 | Celgene Quanticel Research, Inc. | Histone demethylase inhibitors |
| TW201607923A (zh) | 2014-07-15 | 2016-03-01 | 歌林達有限公司 | 被取代之氮螺環(4.5)癸烷衍生物 |
| CN107987067A (zh) * | 2017-11-07 | 2018-05-04 | 大连理工大学 | 一类新型的5-酰胺基-1,4,5-三取代的1,2,3-三氮唑 |
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| JPS568352A (en) * | 1979-07-03 | 1981-01-28 | Shionogi & Co Ltd | Aminoalkylvenzene derivative |
| CA2373855A1 (en) * | 1999-05-12 | 2000-11-23 | Solvay Pharmaceuticals B.V. | Method of treating psychotic disorders |
| US7138397B2 (en) | 2000-10-06 | 2006-11-21 | Tanabe Seiyaku Co., Ltd. | Nitrogenous 5-membered ring compounds |
| ES2188344B1 (es) * | 2000-11-29 | 2004-09-16 | Laboratorios Vita, S.A. | Compuestos derivados de benzotiofeno, su procedimiento de obtencion y utilizacion de los mismos. |
| DE10123163A1 (de) | 2001-05-09 | 2003-01-16 | Gruenenthal Gmbh | Substituierte Cyclohexan-1,4-diaminderivate |
| GB0112834D0 (en) * | 2001-05-25 | 2001-07-18 | Smithkline Beecham Plc | Medicaments |
| DE10130020A1 (de) * | 2001-06-25 | 2003-12-04 | Gruenenthal Gmbh | Substituierte 1-Oxa-2,8-diaza-spiro[4.5]dec-2-en-derivate |
| EP1458704A1 (en) * | 2001-12-21 | 2004-09-22 | H. Lundbeck A/S | Aminoindane derivatives as serotonin and norepinephrine uptake inhibitors |
| US20040110802A1 (en) | 2002-08-23 | 2004-06-10 | Atli Thorarensen | Antibacterial benzoic acid derivatives |
| DE10252650A1 (de) * | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Cyclohexyl-Harnstoff-Derivate |
| DE10252666A1 (de) * | 2002-11-11 | 2004-08-05 | Grünenthal GmbH | N-Piperidyl-cyclohexan-Derivate |
| US20060089398A1 (en) * | 2003-03-19 | 2006-04-27 | Gang Liu | Isoxazole carboxamide derivatives as ghrelin receptor modulators |
| DE102004023506A1 (de) * | 2004-05-10 | 2005-12-01 | Grünenthal GmbH | Kettenverlängerte substituierte Cyclohexyl-1,4-diamin-Derivate |
| DE102004023635A1 (de) | 2004-05-10 | 2006-04-13 | Grünenthal GmbH | Heteroarylsubstituierte Cyclohexyl-1,4-diamin-Derivate |
-
2004
- 2004-05-10 DE DE102004023635A patent/DE102004023635A1/de not_active Withdrawn
-
2005
- 2005-05-06 SI SI200531621T patent/SI1745009T1/sl unknown
- 2005-05-06 CA CA2566212A patent/CA2566212C/en not_active Expired - Fee Related
- 2005-05-06 JP JP2007512031A patent/JP4982357B2/ja not_active Expired - Fee Related
- 2005-05-06 PT PT57591448T patent/PT1745009E/pt unknown
- 2005-05-06 ES ES05759144T patent/ES2395430T3/es not_active Expired - Lifetime
- 2005-05-06 PL PL05759144T patent/PL1745009T3/pl unknown
- 2005-05-06 DK DK05759144.8T patent/DK1745009T3/da active
- 2005-05-06 EP EP05759144A patent/EP1745009B1/de not_active Expired - Lifetime
- 2005-05-06 WO PCT/EP2005/004911 patent/WO2005110971A1/de not_active Ceased
-
2006
- 2006-11-09 US US11/595,003 patent/US8093272B2/en not_active Expired - Fee Related
-
2012
- 2012-12-28 CY CY20121101271T patent/CY1113533T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP4982357B2 (ja) | 2012-07-25 |
| JP2007536321A (ja) | 2007-12-13 |
| DE102004023635A1 (de) | 2006-04-13 |
| CA2566212A1 (en) | 2005-11-24 |
| EP1745009B1 (de) | 2012-11-14 |
| US20070129369A1 (en) | 2007-06-07 |
| EP1745009A1 (de) | 2007-01-24 |
| WO2005110971A1 (de) | 2005-11-24 |
| CY1113533T1 (el) | 2016-06-22 |
| ES2395430T3 (es) | 2013-02-12 |
| DK1745009T3 (da) | 2013-01-02 |
| US8093272B2 (en) | 2012-01-10 |
| SI1745009T1 (sl) | 2012-12-31 |
| PL1745009T3 (pl) | 2013-02-28 |
| PT1745009E (pt) | 2013-01-04 |
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| Date | Code | Title | Description |
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| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20170510 |