JP2007536321A5 - - Google Patents
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- JP2007536321A5 JP2007536321A5 JP2007512031A JP2007512031A JP2007536321A5 JP 2007536321 A5 JP2007536321 A5 JP 2007536321A5 JP 2007512031 A JP2007512031 A JP 2007512031A JP 2007512031 A JP2007512031 A JP 2007512031A JP 2007536321 A5 JP2007536321 A5 JP 2007536321A5
- Authority
- JP
- Japan
- Prior art keywords
- cyclohexyl
- dimethylamino
- phenyl
- benzyl
- carboxylic acid
- 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.)
- Granted
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- 239000003814 drug Substances 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 229940079593 drug Drugs 0.000 claims description 7
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 208000011117 substance-related disease Diseases 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 3
- 230000003444 anaesthetic effect Effects 0.000 claims description 3
- 229940005483 opioid analgesics Drugs 0.000 claims description 3
- 208000019901 Anxiety disease Diseases 0.000 claims description 2
- 206010006895 Cachexia Diseases 0.000 claims description 2
- 208000009132 Catalepsy Diseases 0.000 claims description 2
- 206010011878 Deafness Diseases 0.000 claims description 2
- 206010012335 Dependence Diseases 0.000 claims description 2
- 206010012735 Diarrhoea Diseases 0.000 claims description 2
- 206010013654 Drug abuse Diseases 0.000 claims description 2
- 208000017228 Gastrointestinal motility disease Diseases 0.000 claims description 2
- 208000001953 Hypotension Diseases 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 208000016285 Movement disease Diseases 0.000 claims description 2
- 208000003251 Pruritus Diseases 0.000 claims description 2
- 206010039966 Senile dementia Diseases 0.000 claims description 2
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 2
- 208000009205 Tinnitus Diseases 0.000 claims description 2
- 206010046543 Urinary incontinence Diseases 0.000 claims description 2
- 206010047853 Waxy flexibility Diseases 0.000 claims description 2
- 230000001773 anti-convulsant effect Effects 0.000 claims description 2
- 239000001961 anticonvulsive agent Substances 0.000 claims description 2
- 229960003965 antiepileptics Drugs 0.000 claims description 2
- 230000036506 anxiety Effects 0.000 claims description 2
- 239000002249 anxiolytic agent Substances 0.000 claims description 2
- 230000000949 anxiolytic effect Effects 0.000 claims description 2
- 230000004596 appetite loss Effects 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 239000002934 diuretic Substances 0.000 claims description 2
- 206010013663 drug dependence Diseases 0.000 claims description 2
- 206010015037 epilepsy Diseases 0.000 claims description 2
- 230000029142 excretion Effects 0.000 claims description 2
- 230000010370 hearing loss Effects 0.000 claims description 2
- 231100000888 hearing loss Toxicity 0.000 claims description 2
- 208000016354 hearing loss disease Diseases 0.000 claims description 2
- 230000036543 hypotension Effects 0.000 claims description 2
- 208000019017 loss of appetite Diseases 0.000 claims description 2
- 235000021266 loss of appetite Nutrition 0.000 claims description 2
- 206010027175 memory impairment Diseases 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- 230000037023 motor activity Effects 0.000 claims description 2
- 239000003158 myorelaxant agent Substances 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
- 230000001777 nootropic effect Effects 0.000 claims description 2
- 239000000014 opioid analgesic Substances 0.000 claims description 2
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- 231100000886 tinnitus Toxicity 0.000 claims description 2
- -1 methyl Isoxazolyl Chemical group 0.000 claims 7
- 239000002253 acid Substances 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 5
- 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 4
- 208000002193 Pain Diseases 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 150000001768 cations Chemical class 0.000 claims 2
- 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 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- BBZWRVDYWQISNR-UHFFFAOYSA-N 1-(4-chlorophenyl)-N-[4-(dimethylamino)-4-[(4-fluorophenyl)methyl]cyclohexyl]-5-(trifluoromethyl)pyrazole-4-carboxamide 1-(4-chlorophenyl)-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound ClC1=CC=C(C=C1)N1N=CC(=C1C(F)(F)F)C(=O)O.CN(C1(CCC(CC1)NC(=O)C=1C=NN(C1C(F)(F)F)C1=CC=C(C=C1)Cl)CC1=CC=C(C=C1)F)C BBZWRVDYWQISNR-UHFFFAOYSA-N 0.000 claims 1
- NMMNBCCAWQVWIC-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-[1-(4-morpholin-4-ylphenyl)cyclohexyl]-5-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound FC(F)(F)C1=C(C(=O)NC2(CCCCC2)C=2C=CC(=CC=2)N2CCOCC2)C=NN1C1=CC=C(Cl)C=C1 NMMNBCCAWQVWIC-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- HEPWFNDTOMRGDP-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-[4-(dimethylamino)-4-[(4-methylphenyl)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=C(C)C=C1 HEPWFNDTOMRGDP-UHFFFAOYSA-N 0.000 claims 1
- SFEDTCBOEPHPJI-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)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(Cl)=C1 SFEDTCBOEPHPJI-UHFFFAOYSA-N 0.000 claims 1
- AWQFZBIKLPUZJQ-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)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=C(Cl)C=C1 AWQFZBIKLPUZJQ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- QDBPOHGSAYDWMB-UHFFFAOYSA-N 2-(4-chlorophenyl)sulfanyl-n-[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexyl]pyridine-3-carboxamide Chemical compound C1CC(N(C)C)(C=2C=C(F)C=CC=2)CCC1NC(=O)C1=CC=CN=C1SC1=CC=C(Cl)C=C1 QDBPOHGSAYDWMB-UHFFFAOYSA-N 0.000 claims 1
- PTXPONBVKISFNC-UHFFFAOYSA-N 2-(4-chlorophenyl)sulfanyl-n-[4-(dimethylamino)-4-[(2-fluorophenyl)methyl]cyclohexyl]pyridine-3-carboxamide Chemical compound C1CC(NC(=O)C=2C(=NC=CC=2)SC=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=CC=C1F PTXPONBVKISFNC-UHFFFAOYSA-N 0.000 claims 1
- HATQTZBIRILWPB-UHFFFAOYSA-N 2-(4-chlorophenyl)sulfanyl-n-[4-(dimethylamino)-4-[(2-methylphenyl)methyl]cyclohexyl]pyridine-3-carboxamide Chemical compound C1CC(NC(=O)C=2C(=NC=CC=2)SC=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=CC=C1C HATQTZBIRILWPB-UHFFFAOYSA-N 0.000 claims 1
- SZXYXCBWELKFAH-UHFFFAOYSA-N 2-(4-chlorophenyl)sulfanyl-n-[4-(dimethylamino)-4-[(3-fluorophenyl)methyl]cyclohexyl]pyridine-3-carboxamide Chemical compound C1CC(NC(=O)C=2C(=NC=CC=2)SC=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=CC(F)=C1 SZXYXCBWELKFAH-UHFFFAOYSA-N 0.000 claims 1
- IUHVVIWILWTIJF-UHFFFAOYSA-N 2-(4-chlorophenyl)sulfanyl-n-[4-(dimethylamino)-4-[(4-fluorophenyl)methyl]cyclohexyl]pyridine-3-carboxamide Chemical compound C1CC(NC(=O)C=2C(=NC=CC=2)SC=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=C(F)C=C1 IUHVVIWILWTIJF-UHFFFAOYSA-N 0.000 claims 1
- LIPRZNZVHLDIHB-UHFFFAOYSA-N 2-(4-chlorophenyl)sulfanyl-n-[4-(dimethylamino)-4-pyridin-2-ylcyclohexyl]pyridine-3-carboxamide Chemical compound C1CC(N(C)C)(C=2N=CC=CC=2)CCC1NC(=O)C1=CC=CN=C1SC1=CC=C(Cl)C=C1 LIPRZNZVHLDIHB-UHFFFAOYSA-N 0.000 claims 1
- QHORJRNFOYRWIP-UHFFFAOYSA-N 2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)-n-(4-phenyl-4-piperidin-1-ylcyclohexyl)acetamide Chemical compound CC=1SC(C=2C=CC=CC=2)=NC=1CC(=O)NC(CC1)CCC1(C=1C=CC=CC=1)N1CCCCC1 QHORJRNFOYRWIP-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 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 1
- 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 1
- 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 1
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 claims 1
- 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 1
- 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 1
- XLXYTICMKGWPRB-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-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(Cl)C=CC=C1Cl XLXYTICMKGWPRB-UHFFFAOYSA-N 0.000 claims 1
- ABDPXPAETUSBCP-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-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=2Cl)Cl)CCC1(N(C)C)CC1=CC=CC=C1F ABDPXPAETUSBCP-UHFFFAOYSA-N 0.000 claims 1
- JBQYIYJMVVUFGO-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-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=2Cl)Cl)CCC1(N(C)C)CC1=CC=CC=C1C JBQYIYJMVVUFGO-UHFFFAOYSA-N 0.000 claims 1
- IDSUICRYHCXIIL-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-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=2Cl)Cl)CCC1(N(C)C)CC1=CC=CC(F)=C1 IDSUICRYHCXIIL-UHFFFAOYSA-N 0.000 claims 1
- HYOKEMQURGNJPL-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-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=2Cl)Cl)CCC1(N(C)C)CC1=CC=C(F)C=C1 HYOKEMQURGNJPL-UHFFFAOYSA-N 0.000 claims 1
- XCMTVYSVSFSUBQ-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-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=2Cl)Cl)CCC1(N(C)C)CC1=CC=C(C)C=C1 XCMTVYSVSFSUBQ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- CHZWUJOQFXJFEN-UHFFFAOYSA-N 3-(2-chloro-6-fluorophenyl)-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=2F)Cl)CCC1(N(C)C)CCC1=CC=CC=C1 CHZWUJOQFXJFEN-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- GMYGWEFPLAPTDQ-UHFFFAOYSA-N 3-(2-chlorophenyl)-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=2)Cl)CCC1(N(C)C)CCC1=CC=CC=C1 GMYGWEFPLAPTDQ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- IDFMQWUZMQUAPJ-UHFFFAOYSA-N 3-(2-chlorophenyl)-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=2)Cl)CCC1(N(C)C)CC1=CC=CC=C1F IDFMQWUZMQUAPJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- ZQTTYAVGHIVLQK-UHFFFAOYSA-N 3-(2-chlorophenyl)-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=2)Cl)CCC1(N(C)C)CC1=CC=CC(F)=C1 ZQTTYAVGHIVLQK-UHFFFAOYSA-N 0.000 claims 1
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- SVHOBSWMKIDEFU-UHFFFAOYSA-N n-[4-(dimethylamino)-4-phenylcyclohexyl]-2-phenoxypyridine-3-carboxamide Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)C1=CC=CN=C1OC1=CC=CC=C1 SVHOBSWMKIDEFU-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- SATDJKUPRJFIAY-UHFFFAOYSA-N n-[4-(dimethylamino)-4-pyridin-2-ylcyclohexyl]-2-phenoxypyridine-3-carboxamide Chemical compound C1CC(N(C)C)(C=2N=CC=CC=2)CCC1NC(=O)C1=CC=CN=C1OC1=CC=CC=C1 SATDJKUPRJFIAY-UHFFFAOYSA-N 0.000 claims 1
- WRUDABMNAQOAFY-UHFFFAOYSA-N n-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]-2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)acetamide Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)CC(=C(S1)C)N=C1C1=CC=CC=C1 WRUDABMNAQOAFY-UHFFFAOYSA-N 0.000 claims 1
- ZWJQVLOXOBYARW-UHFFFAOYSA-N n-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]-2-phenoxypyridine-3-carboxamide Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)C1=CC=CN=C1OC1=CC=CC=C1 ZWJQVLOXOBYARW-UHFFFAOYSA-N 0.000 claims 1
- ALDJQEKILVAOEV-UHFFFAOYSA-N n-[4-[(2-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-1-phenyl-5-propylpyrazole-4-carboxamide Chemical compound CCCC1=C(C(=O)NC2CCC(CC=3C(=CC=CC=3)Cl)(CC2)N(C)C)C=NN1C1=CC=CC=C1 ALDJQEKILVAOEV-UHFFFAOYSA-N 0.000 claims 1
- RBEKCMPADWBUHZ-UHFFFAOYSA-N n-[4-[(2-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-3-(2,6-dichlorophenyl)-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)CC1=CC=CC=C1Cl RBEKCMPADWBUHZ-UHFFFAOYSA-N 0.000 claims 1
- IJKMIZWYQXMZAC-UHFFFAOYSA-N n-[4-[(2-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-5-methyl-2-phenyltriazole-4-carboxamide Chemical compound C1CC(NC(=O)C=2C(=NN(N=2)C=2C=CC=CC=2)C)CCC1(N(C)C)CC1=CC=CC=C1Cl IJKMIZWYQXMZAC-UHFFFAOYSA-N 0.000 claims 1
- UUBIYVIAFGBLQJ-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-2-(4-chlorophenyl)sulfanylpyridine-3-carboxamide Chemical compound C1CC(NC(=O)C=2C(=NC=CC=2)SC=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 UUBIYVIAFGBLQJ-UHFFFAOYSA-N 0.000 claims 1
- HACVOPANPBXTJV-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)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=CC(Cl)=C1 HACVOPANPBXTJV-UHFFFAOYSA-N 0.000 claims 1
- XSNVFWAZKVUFCR-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methyl]-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(Cl)=C1 XSNVFWAZKVUFCR-UHFFFAOYSA-N 0.000 claims 1
- DKFZZVRBRYLLPN-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-5-methyl-2-phenyltriazole-4-carboxamide Chemical compound C1CC(NC(=O)C=2C(=NN(N=2)C=2C=CC=CC=2)C)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 DKFZZVRBRYLLPN-UHFFFAOYSA-N 0.000 claims 1
- SRLQUZAEPUMPNM-UHFFFAOYSA-N n-[4-[(4-chlorophenyl)methyl]-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=C(Cl)C=C1 SRLQUZAEPUMPNM-UHFFFAOYSA-N 0.000 claims 1
- DKZQXEXWFJJRJU-UHFFFAOYSA-N n-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)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(Cl)C=C1 DKZQXEXWFJJRJU-UHFFFAOYSA-N 0.000 claims 1
- MBWGHUBWJXPYLG-UHFFFAOYSA-N n-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-3-(2,6-dichlorophenyl)-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)CC1=CC=C(Cl)C=C1 MBWGHUBWJXPYLG-UHFFFAOYSA-N 0.000 claims 1
- MCNYCUHLXAVXJQ-UHFFFAOYSA-N n-[4-[(4-chlorophenyl)methyl]-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=C(Cl)C=C1 MCNYCUHLXAVXJQ-UHFFFAOYSA-N 0.000 claims 1
- CNISPFZYNSWTDI-UHFFFAOYSA-N n-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-5-methyl-2-phenyltriazole-4-carboxamide Chemical compound C1CC(NC(=O)C=2C(=NN(N=2)C=2C=CC=CC=2)C)CCC1(N(C)C)CC1=CC=C(Cl)C=C1 CNISPFZYNSWTDI-UHFFFAOYSA-N 0.000 claims 1
- OWEDYUHNDQVVPD-UHFFFAOYSA-N n-[4-benzyl-4-(dimethylamino)cyclohexyl]-1-(4-chlorophenyl)-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=C1 OWEDYUHNDQVVPD-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- QBOYZKVWCGAMQL-UHFFFAOYSA-N n-[4-benzyl-4-(dimethylamino)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=CC=C1 QBOYZKVWCGAMQL-UHFFFAOYSA-N 0.000 claims 1
- CNXYZJIKRCOWOP-UHFFFAOYSA-N n-[4-benzyl-4-(dimethylamino)cyclohexyl]-3-(2,6-dichlorophenyl)-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)CC1=CC=CC=C1 CNXYZJIKRCOWOP-UHFFFAOYSA-N 0.000 claims 1
- QYGUGNFXPPICPJ-UHFFFAOYSA-N n-[4-benzyl-4-(dimethylamino)cyclohexyl]-3-(2-chloro-6-fluorophenyl)-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=C1 QYGUGNFXPPICPJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- VYPQSCOUKVDMIK-UHFFFAOYSA-N n-[4-benzyl-4-(dimethylamino)cyclohexyl]-5-[[3-(trifluoromethyl)phenyl]methylsulfonyl]-6,7-dihydro-4h-[1,2]oxazolo[4,5-c]pyridine-3-carboxamide Chemical compound C1CC(NC(=O)C=2C=3CN(CCC=3ON=2)S(=O)(=O)CC=2C=C(C=CC=2)C(F)(F)F)CCC1(N(C)C)CC1=CC=CC=C1 VYPQSCOUKVDMIK-UHFFFAOYSA-N 0.000 claims 1
- BNLNYFLNSXHVSV-UHFFFAOYSA-N n-[4-benzyl-4-(dimethylamino)cyclohexyl]-5-methyl-2-phenyltriazole-4-carboxamide Chemical compound C1CC(NC(=O)C=2C(=NN(N=2)C=2C=CC=CC=2)C)CCC1(N(C)C)CC1=CC=CC=C1 BNLNYFLNSXHVSV-UHFFFAOYSA-N 0.000 claims 1
- CMPPYKWIWFBRBZ-UHFFFAOYSA-N n-[4-benzyl-4-(dimethylamino)cyclohexyl]-5-thiophen-2-ylsulfonyl-6,7-dihydro-4h-[1,2]oxazolo[4,5-c]pyridine-3-carboxamide Chemical compound C1CC(NC(=O)C=2C=3CN(CCC=3ON=2)S(=O)(=O)C=2SC=CC=2)CCC1(N(C)C)CC1=CC=CC=C1 CMPPYKWIWFBRBZ-UHFFFAOYSA-N 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 239000002858 neurotransmitter agent Substances 0.000 claims 1
- 235000015816 nutrient absorption Nutrition 0.000 claims 1
- 229940052318 opioid anesthetics Drugs 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229940005530 anxiolytics Drugs 0.000 description 1
- 230000003920 cognitive function Effects 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 230000003957 neurotransmitter release Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
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 (3)
| Publication Number | Publication Date |
|---|---|
| JP2007536321A JP2007536321A (ja) | 2007-12-13 |
| JP2007536321A5 true JP2007536321A5 (https=) | 2012-03-08 |
| JP4982357B2 JP4982357B2 (ja) | 2012-07-25 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2007512031A Expired - Fee Related JP4982357B2 (ja) | 2004-05-10 | 2005-05-06 | ヘテロアリール−置換されたシクロヘキシル−１，４−ジアミン誘導体 |
Country Status (12)
| Country | Link |
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| 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 |
|---|---|---|---|---|
| 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 |
| 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 |
| HUE026011T2 (en) | 2006-03-22 | 2016-05-30 | Hoffmann La Roche | Pyrazoles as 11-beta-HSD-1 |
| DE102006046745A1 (de) * | 2006-09-29 | 2008-04-03 | Grünenthal GmbH | Gemischte ORL1/µ-Agonisten zur Behandlung von Schmerz |
| PT2260042E (pt) | 2008-03-27 | 2011-12-06 | Gruenenthal Gmbh | Derivados de ciclo-hexano espirocíclicos substituídos |
| WO2009118174A1 (de) | 2008-03-27 | 2009-10-01 | Grünenthal GmbH | Substituierte cyclohexyldiamine |
| CA2719735A1 (en) | 2008-03-27 | 2009-10-01 | Gruenenthal Gmbh | Substituted 4-aminocyclohexane derivatives |
| AU2009228637B2 (en) | 2008-03-27 | 2013-12-19 | Grunenthal Gmbh | (Hetero-)aryl cyclohexane derivatives |
| JP5599774B2 (ja) | 2008-03-27 | 2014-10-01 | 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 | ヒドロキシメチルシクロヘキシルアミン類 |
| ATE537143T1 (de) | 2008-03-27 | 2011-12-15 | Gruenenthal Gmbh | Spiro(5.5)undecan derivate |
| 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 |
| CA2894399A1 (en) | 2012-12-06 | 2014-06-12 | Quanticel Pharmaceuticals, 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 |
| JP2002544223A (ja) * | 1999-05-12 | 2002-12-24 | ソルベイ・フアーマシユーチカルズ・ベー・ブイ | 精神病性障害の治療方法 |
| BR0114436A (pt) | 2000-10-06 | 2003-07-01 | Tanabe Seiyaku Co | Composto com anel de cinco elementos contendo nitrogênio alifático |
| 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 |
| CA2467337A1 (en) * | 2001-12-21 | 2003-07-10 | 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 |
| DE10252666A1 (de) * | 2002-11-11 | 2004-08-05 | Grünenthal GmbH | N-Piperidyl-cyclohexan-Derivate |
| DE10252650A1 (de) * | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Cyclohexyl-Harnstoff-Derivate |
| US20060089398A1 (en) * | 2003-03-19 | 2006-04-27 | Gang Liu | Isoxazole carboxamide derivatives as ghrelin receptor modulators |
| 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 |
-
2004
- 2004-05-10 DE DE102004023635A patent/DE102004023635A1/de not_active Withdrawn
-
2005
- 2005-05-06 PL PL05759144T patent/PL1745009T3/pl unknown
- 2005-05-06 PT PT57591448T patent/PT1745009E/pt unknown
- 2005-05-06 WO PCT/EP2005/004911 patent/WO2005110971A1/de not_active Ceased
- 2005-05-06 CA CA2566212A patent/CA2566212C/en not_active Expired - Fee Related
- 2005-05-06 ES ES05759144T patent/ES2395430T3/es not_active Expired - Lifetime
- 2005-05-06 DK DK05759144.8T patent/DK1745009T3/da active
- 2005-05-06 SI SI200531621T patent/SI1745009T1/sl unknown
- 2005-05-06 JP JP2007512031A patent/JP4982357B2/ja not_active Expired - Fee Related
- 2005-05-06 EP EP05759144A patent/EP1745009B1/de not_active Expired - Lifetime
-
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
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