ES2395430T3 - Derivados de ciclohexil-1,4-diamina sustituidos con heteroarilo - Google Patents
Derivados de ciclohexil-1,4-diamina sustituidos con heteroarilo Download PDFInfo
- Publication number
- ES2395430T3 ES2395430T3 ES05759144T ES05759144T ES2395430T3 ES 2395430 T3 ES2395430 T3 ES 2395430T3 ES 05759144 T ES05759144 T ES 05759144T ES 05759144 T ES05759144 T ES 05759144T ES 2395430 T3 ES2395430 T3 ES 2395430T3
- Authority
- ES
- Spain
- Prior art keywords
- amide
- carboxylic acid
- dimethylamino
- cyclohexyl
- methyl
- 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 - Lifetime
Links
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 41
- 125000003118 aryl group Chemical group 0.000 claims abstract description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 24
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 21
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 5
- -1 benzodioxolanyl Chemical group 0.000 claims description 105
- 239000002253 acid Substances 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 28
- 239000003814 drug Substances 0.000 claims description 26
- 125000001544 thienyl group Chemical group 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 21
- 125000002541 furyl group Chemical group 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 19
- 208000002193 Pain Diseases 0.000 claims description 18
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 17
- 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 16
- 239000000203 mixture Substances 0.000 claims description 16
- 125000001041 indolyl group Chemical group 0.000 claims description 15
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 14
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 125000001624 naphthyl group Chemical group 0.000 claims description 14
- 150000001768 cations Chemical class 0.000 claims description 13
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 13
- 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 12
- 150000007513 acids Chemical class 0.000 claims description 12
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 12
- 229940079593 drug Drugs 0.000 claims description 11
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 11
- 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 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 10
- 230000036407 pain Effects 0.000 claims description 10
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 9
- 125000001425 triazolyl group Chemical group 0.000 claims description 9
- 239000004480 active ingredient Substances 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 group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 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 7
- 150000001408 amides Chemical class 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 7
- 238000002483 medication Methods 0.000 claims description 7
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 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
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 6
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004306 triazinyl group Chemical group 0.000 claims description 6
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 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 5
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 5
- PENHKTNQUJMHIR-UHFFFAOYSA-N 5-methyl-3-phenyl-1,2-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=C(C)ON=C1C1=CC=CC=C1 PENHKTNQUJMHIR-UHFFFAOYSA-N 0.000 claims description 5
- 230000003444 anaesthetic effect Effects 0.000 claims description 5
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 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 4
- DFVPTAVNWBPVIH-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexyl]-5-methyl-1,2-oxazole-4-carboxamide Chemical compound C1CC(N(C)C)(C=2C=C(F)C=CC=2)CCC1NC(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl DFVPTAVNWBPVIH-UHFFFAOYSA-N 0.000 claims description 4
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical group C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 206010061428 decreased appetite Diseases 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- VRXHKNQNFCKCII-UHFFFAOYSA-N 1-(4-chlorophenyl)-N-(4-morpholin-4-yl-4-phenylcyclohexyl)-5-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound N1(CCOCC1)C1(CCC(CC1)NC(=O)C=1C=NN(C=1C(F)(F)F)C1=CC=C(C=C1)Cl)C1=CC=CC=C1 VRXHKNQNFCKCII-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- DGTOZYDZWNCSMC-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-[4-(dimethylamino)-4-[(2-fluorophenyl)methyl]cyclohexyl]-5-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C1CC(NC(=O)C2=C(N(N=C2)C=2C=CC(Cl)=CC=2)C(F)(F)F)CCC1(N(C)C)CC1=CC=CC=C1F DGTOZYDZWNCSMC-UHFFFAOYSA-N 0.000 claims description 3
- JXBROYXIOAGAAT-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-5-methyl-n-(4-phenyl-4-piperidin-1-ylcyclohexyl)-1,2-oxazole-4-carboxamide Chemical compound CC=1ON=C(C=2C(=CC=CC=2Cl)Cl)C=1C(=O)NC(CC1)CCC1(C=1C=CC=CC=1)N1CCCCC1 JXBROYXIOAGAAT-UHFFFAOYSA-N 0.000 claims description 3
- VTGLUVDPGMIVEJ-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-n-[4-(dimethylamino)-4-(2-phenylethyl)cyclohexyl]-5-methyl-1,2-oxazole-4-carboxamide Chemical compound C1CC(NC(=O)C=2C(=NOC=2C)C=2C(=CC=CC=2Cl)Cl)CCC1(N(C)C)CCC1=CC=CC=C1 VTGLUVDPGMIVEJ-UHFFFAOYSA-N 0.000 claims description 3
- NEWZTONRUIRHGT-UHFFFAOYSA-N 3-(2-chloro-6-fluorophenyl)-5-methyl-n-(4-phenyl-4-piperidin-1-ylcyclohexyl)-1,2-oxazole-4-carboxamide Chemical compound CC=1ON=C(C=2C(=CC=CC=2F)Cl)C=1C(=O)NC(CC1)CCC1(C=1C=CC=CC=1)N1CCCCC1 NEWZTONRUIRHGT-UHFFFAOYSA-N 0.000 claims description 3
- ASISJGUJZQXZIG-UHFFFAOYSA-N 3-(2-chloro-6-fluorophenyl)-n-[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexyl]-5-methyl-1,2-oxazole-4-carboxamide Chemical compound C1CC(N(C)C)(C=2C=C(F)C=CC=2)CCC1NC(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl ASISJGUJZQXZIG-UHFFFAOYSA-N 0.000 claims description 3
- LVGYGBDSIAIJFA-UHFFFAOYSA-N 3-(2-chloro-6-fluorophenyl)-n-[4-(dimethylamino)-4-[(2-fluorophenyl)methyl]cyclohexyl]-5-methyl-1,2-oxazole-4-carboxamide Chemical compound C1CC(NC(=O)C=2C(=NOC=2C)C=2C(=CC=CC=2F)Cl)CCC1(N(C)C)CC1=CC=CC=C1F LVGYGBDSIAIJFA-UHFFFAOYSA-N 0.000 claims description 3
- KGTOEZNKHOVYEC-UHFFFAOYSA-N 3-(2-chloro-6-fluorophenyl)-n-[4-(dimethylamino)-4-[(2-methylphenyl)methyl]cyclohexyl]-5-methyl-1,2-oxazole-4-carboxamide Chemical compound C1CC(NC(=O)C=2C(=NOC=2C)C=2C(=CC=CC=2F)Cl)CCC1(N(C)C)CC1=CC=CC=C1C KGTOEZNKHOVYEC-UHFFFAOYSA-N 0.000 claims description 3
- FSNJZBZJQGLZDR-UHFFFAOYSA-N 3-(2-chloro-6-fluorophenyl)-n-[4-(dimethylamino)-4-[(3-fluorophenyl)methyl]cyclohexyl]-5-methyl-1,2-oxazole-4-carboxamide Chemical compound C1CC(NC(=O)C=2C(=NOC=2C)C=2C(=CC=CC=2F)Cl)CCC1(N(C)C)CC1=CC=CC(F)=C1 FSNJZBZJQGLZDR-UHFFFAOYSA-N 0.000 claims description 3
- GUAOVXXZQBWNRF-UHFFFAOYSA-N 3-(2-chloro-6-fluorophenyl)-n-[4-(dimethylamino)-4-[(4-fluorophenyl)methyl]cyclohexyl]-5-methyl-1,2-oxazole-4-carboxamide Chemical compound C1CC(NC(=O)C=2C(=NOC=2C)C=2C(=CC=CC=2F)Cl)CCC1(N(C)C)CC1=CC=C(F)C=C1 GUAOVXXZQBWNRF-UHFFFAOYSA-N 0.000 claims description 3
- YLOAPRHFEVGNMY-UHFFFAOYSA-N 3-(2-chloro-6-fluorophenyl)-n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-5-methyl-1,2-oxazole-4-carboxamide Chemical compound C1CC(NC(=O)C=2C(=NOC=2C)C=2C(=CC=CC=2F)Cl)CCC1(N(C)C)CC1=CC=C(C)C=C1 YLOAPRHFEVGNMY-UHFFFAOYSA-N 0.000 claims description 3
- BEKIEHOUFXRKIG-UHFFFAOYSA-N 3-(2-chloro-6-fluorophenyl)-n-[4-(dimethylamino)-4-phenylcyclohexyl]-5-methyl-1,2-oxazole-4-carboxamide Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl BEKIEHOUFXRKIG-UHFFFAOYSA-N 0.000 claims description 3
- PNXKBJIOXNOQGK-UHFFFAOYSA-N 3-(2-chloro-6-fluorophenyl)-n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-5-methyl-1,2-oxazole-4-carboxamide Chemical compound C1CC(NC(=O)C=2C(=NOC=2C)C=2C(=CC=CC=2F)Cl)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 PNXKBJIOXNOQGK-UHFFFAOYSA-N 0.000 claims description 3
- MJTLKCFQWBOOML-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-[4-(dimethylamino)-4-[(2-methylphenyl)methyl]cyclohexyl]-5-methyl-1,2-oxazole-4-carboxamide Chemical compound C1CC(NC(=O)C=2C(=NOC=2C)C=2C(=CC=CC=2)Cl)CCC1(N(C)C)CC1=CC=CC=C1C MJTLKCFQWBOOML-UHFFFAOYSA-N 0.000 claims description 3
- YXYBGYQPRNOIGU-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-5-methyl-1,2-oxazole-4-carboxamide Chemical compound C1CC(NC(=O)C=2C(=NOC=2C)C=2C(=CC=CC=2)Cl)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 YXYBGYQPRNOIGU-UHFFFAOYSA-N 0.000 claims description 3
- QOXVRQUSQSUQLZ-UHFFFAOYSA-N 5-benzyl-n-(4-benzyl-4-piperidin-1-ylcyclohexyl)furan-2-carboxamide Chemical compound C=1C=C(CC=2C=CC=CC=2)OC=1C(=O)NC(CC1)CCC1(N1CCCCC1)CC1=CC=CC=C1 QOXVRQUSQSUQLZ-UHFFFAOYSA-N 0.000 claims description 3
- NSCVJQDCVPGGFV-UHFFFAOYSA-N 5-benzyl-n-(4-phenyl-4-piperidin-1-ylcyclohexyl)furan-2-carboxamide Chemical compound C=1C=C(CC=2C=CC=CC=2)OC=1C(=O)NC(CC1)CCC1(C=1C=CC=CC=1)N1CCCCC1 NSCVJQDCVPGGFV-UHFFFAOYSA-N 0.000 claims description 3
- HBJIBJNXXQBVKX-UHFFFAOYSA-N 5-benzyl-n-[4-(dimethylamino)-4-(2-phenylethyl)cyclohexyl]furan-2-carboxamide Chemical compound C1CC(NC(=O)C=2OC(CC=3C=CC=CC=3)=CC=2)CCC1(N(C)C)CCC1=CC=CC=C1 HBJIBJNXXQBVKX-UHFFFAOYSA-N 0.000 claims description 3
- PXDXFEYLWDSFFQ-UHFFFAOYSA-N 5-benzyl-n-[4-(dimethylamino)-4-[(2-fluorophenyl)methyl]cyclohexyl]furan-2-carboxamide Chemical compound C1CC(NC(=O)C=2OC(CC=3C=CC=CC=3)=CC=2)CCC1(N(C)C)CC1=CC=CC=C1F PXDXFEYLWDSFFQ-UHFFFAOYSA-N 0.000 claims description 3
- KRTLOPSBELRRGP-UHFFFAOYSA-N 5-benzyl-n-[4-(dimethylamino)-4-[(2-methylphenyl)methyl]cyclohexyl]furan-2-carboxamide Chemical compound C1CC(NC(=O)C=2OC(CC=3C=CC=CC=3)=CC=2)CCC1(N(C)C)CC1=CC=CC=C1C KRTLOPSBELRRGP-UHFFFAOYSA-N 0.000 claims description 3
- RSZNIQLGFIZBFH-UHFFFAOYSA-N 5-benzyl-n-[4-(dimethylamino)-4-[(3-fluorophenyl)methyl]cyclohexyl]furan-2-carboxamide Chemical compound C1CC(NC(=O)C=2OC(CC=3C=CC=CC=3)=CC=2)CCC1(N(C)C)CC1=CC=CC(F)=C1 RSZNIQLGFIZBFH-UHFFFAOYSA-N 0.000 claims description 3
- PCUUAONKBKUVFS-UHFFFAOYSA-N 5-benzyl-n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]furan-2-carboxamide Chemical compound C1CC(NC(=O)C=2OC(CC=3C=CC=CC=3)=CC=2)CCC1(N(C)C)CC1=CC=C(C)C=C1 PCUUAONKBKUVFS-UHFFFAOYSA-N 0.000 claims description 3
- BZSANQFQQOOMCN-UHFFFAOYSA-N 5-benzyl-n-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]furan-2-carboxamide Chemical compound C1CC(NC(=O)C=2OC(CC=3C=CC=CC=3)=CC=2)CCC1(N(C)C)CC1=CC=C(Cl)C=C1 BZSANQFQQOOMCN-UHFFFAOYSA-N 0.000 claims description 3
- 208000009132 Catalepsy Diseases 0.000 claims description 3
- 208000020401 Depressive disease Diseases 0.000 claims description 3
- 206010012735 Diarrhoea Diseases 0.000 claims description 3
- 208000026139 Memory disease Diseases 0.000 claims description 3
- 208000026251 Opioid-Related disease Diseases 0.000 claims description 3
- 208000004880 Polyuria Diseases 0.000 claims description 3
- 206010046543 Urinary incontinence Diseases 0.000 claims description 3
- 206010047853 Waxy flexibility Diseases 0.000 claims description 3
- 206010048010 Withdrawal syndrome Diseases 0.000 claims description 3
- 208000005298 acute pain Diseases 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 208000022531 anorexia Diseases 0.000 claims description 3
- 239000002249 anxiolytic agent Substances 0.000 claims description 3
- 230000000949 anxiolytic effect Effects 0.000 claims description 3
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 239000012964 benzotriazole Substances 0.000 claims description 3
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 230000001684 chronic effect Effects 0.000 claims description 3
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical class NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 238000009826 distribution Methods 0.000 claims description 3
- 230000035619 diuresis Effects 0.000 claims description 3
- 206010015037 epilepsy Diseases 0.000 claims description 3
- 230000008991 intestinal motility Effects 0.000 claims description 3
- 230000037023 motor activity Effects 0.000 claims description 3
- YVTXNQMMDILLAC-UHFFFAOYSA-N n-(4-benzyl-4-piperidin-1-ylcyclohexyl)-3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound CC=1ON=C(C=2C(=CC=CC=2Cl)Cl)C=1C(=O)NC(CC1)CCC1(N1CCCCC1)CC1=CC=CC=C1 YVTXNQMMDILLAC-UHFFFAOYSA-N 0.000 claims description 3
- NLHUQWLZSFXQME-UHFFFAOYSA-N n-(4-benzyl-4-piperidin-1-ylcyclohexyl)-5-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]thiophene-2-carboxamide Chemical compound C1=C(C(F)(F)F)N(C)N=C1C1=CC=C(C(=O)NC2CCC(CC=3C=CC=CC=3)(CC2)N2CCCCC2)S1 NLHUQWLZSFXQME-UHFFFAOYSA-N 0.000 claims description 3
- UTEDZWUMRFVUAQ-UHFFFAOYSA-N n-(4-benzyl-4-pyrrolidin-1-ylcyclohexyl)-2-phenoxypyridine-3-carboxamide Chemical compound C=1C=CN=C(OC=2C=CC=CC=2)C=1C(=O)NC(CC1)CCC1(N1CCCC1)CC1=CC=CC=C1 UTEDZWUMRFVUAQ-UHFFFAOYSA-N 0.000 claims description 3
- UZEPNHXFSYYIKR-UHFFFAOYSA-N n-(4-benzyl-4-pyrrolidin-1-ylcyclohexyl)-3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound CC=1ON=C(C=2C(=CC=CC=2F)Cl)C=1C(=O)NC(CC1)CCC1(N1CCCC1)CC1=CC=CC=C1 UZEPNHXFSYYIKR-UHFFFAOYSA-N 0.000 claims description 3
- OUQFJKZYWVKFSV-UHFFFAOYSA-N n-(4-benzyl-4-pyrrolidin-1-ylcyclohexyl)-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(N1CCCC1)CC1=CC=CC=C1 OUQFJKZYWVKFSV-UHFFFAOYSA-N 0.000 claims description 3
- ZQLBKPZNIRKAFN-UHFFFAOYSA-N n-(4-benzyl-4-pyrrolidin-1-ylcyclohexyl)-5-(4-chlorophenyl)-2-methylfuran-3-carboxamide Chemical compound CC=1OC(C=2C=CC(Cl)=CC=2)=CC=1C(=O)NC(CC1)CCC1(N1CCCC1)CC1=CC=CC=C1 ZQLBKPZNIRKAFN-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
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- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D213/82—Amides; Imides in position 3
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
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- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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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 | 2004-05-10 | ||
| PCT/EP2005/004911 WO2005110971A1 (de) | 2004-05-10 | 2005-05-06 | Heteroarylsubstituierte cyclohexyl-1,4-diamin-derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2395430T3 true ES2395430T3 (es) | 2013-02-12 |
Family
ID=34972310
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES05759144T Expired - Lifetime ES2395430T3 (es) | 2004-05-10 | 2005-05-06 | Derivados de ciclohexil-1,4-diamina sustituidos con heteroarilo |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8093272B2 (https=) |
| EP (1) | EP1745009B1 (https=) |
| JP (1) | JP4982357B2 (https=) |
| CA (1) | CA2566212C (https=) |
| CY (1) | CY1113533T1 (https=) |
| DE (1) | DE102004023635A1 (https=) |
| DK (1) | DK1745009T3 (https=) |
| ES (1) | ES2395430T3 (https=) |
| PL (1) | PL1745009T3 (https=) |
| PT (1) | PT1745009E (https=) |
| SI (1) | SI1745009T1 (https=) |
| WO (1) | WO2005110971A1 (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DK1745009T3 (da) | 2013-01-02 |
| US8093272B2 (en) | 2012-01-10 |
| SI1745009T1 (sl) | 2012-12-31 |
| CA2566212C (en) | 2013-06-18 |
| PL1745009T3 (pl) | 2013-02-28 |
| PT1745009E (pt) | 2013-01-04 |
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