JP5037336B2 - 鎖長が延ばされ、置換されたシクロヘキシル−1,4−ジアミンの酸誘導体 - Google Patents
鎖長が延ばされ、置換されたシクロヘキシル−1,4−ジアミンの酸誘導体 Download PDFInfo
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- JP5037336B2 JP5037336B2 JP2007512032A JP2007512032A JP5037336B2 JP 5037336 B2 JP5037336 B2 JP 5037336B2 JP 2007512032 A JP2007512032 A JP 2007512032A JP 2007512032 A JP2007512032 A JP 2007512032A JP 5037336 B2 JP5037336 B2 JP 5037336B2
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- benzyl
- dimethylamino
- cyclohexyl
- methyl
- chloro
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- 239000002253 acid Substances 0.000 title claims description 18
- 239000003814 drug Substances 0.000 claims description 36
- -1 vinylbenzyl Chemical group 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 208000002193 Pain Diseases 0.000 claims description 21
- 229920006395 saturated elastomer Polymers 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 19
- 238000011282 treatment Methods 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000001544 thienyl group Chemical group 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 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 10
- 239000013543 active substance Substances 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 150000001768 cations Chemical class 0.000 claims description 9
- 229940079593 drug Drugs 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 229940005483 opioid analgesics Drugs 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- NULYMMSGHOWARS-UHFFFAOYSA-N 2-(3-chlorophenoxy)-n-[4-(dimethylamino)-4-phenylcyclohexyl]acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)COC1=CC=CC(Cl)=C1 NULYMMSGHOWARS-UHFFFAOYSA-N 0.000 claims description 6
- 208000000094 Chronic Pain Diseases 0.000 claims description 6
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- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- KREWXDRXGISBEV-UHFFFAOYSA-N n-[4-(dimethylamino)-4-phenylcyclohexyl]-4-phenoxybutanamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)CCCOC1=CC=CC=C1 KREWXDRXGISBEV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 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 5
- 208000011117 substance-related disease Diseases 0.000 claims description 5
- 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 4
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 4
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- 229910052799 carbon Inorganic materials 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
- 201000010099 disease Diseases 0.000 claims description 4
- QKOQLQWBLLMNHW-UHFFFAOYSA-N 2-(3-chlorophenoxy)-n-[4-(dimethylamino)-4-phenylcyclohexyl]acetamide Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)COC1=CC=CC(Cl)=C1 QKOQLQWBLLMNHW-UHFFFAOYSA-N 0.000 claims description 3
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 3
- 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 3
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 3
- 206010012335 Dependence Diseases 0.000 claims description 3
- 206010012735 Diarrhoea Diseases 0.000 claims description 3
- 206010013654 Drug abuse Diseases 0.000 claims description 3
- 206010046543 Urinary incontinence Diseases 0.000 claims description 3
- 208000005298 acute pain Diseases 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 230000003444 anaesthetic effect Effects 0.000 claims description 3
- 208000010877 cognitive disease Diseases 0.000 claims description 3
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- 230000001965 increasing effect Effects 0.000 claims description 3
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- 238000002156 mixing Methods 0.000 claims description 3
- 230000037023 motor activity Effects 0.000 claims description 3
- 208000004296 neuralgia Diseases 0.000 claims description 3
- 230000004770 neurodegeneration Effects 0.000 claims description 3
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- 208000021722 neuropathic pain Diseases 0.000 claims description 3
- 230000001777 nootropic effect Effects 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- VQEJOMSIOUKSJL-UHFFFAOYSA-N 2-(2-chlorophenoxy)-n-[4-(dimethylamino)-4-[(2-methylphenyl)methyl]cyclohexyl]-2-methylpropanamide Chemical compound C1CC(NC(=O)C(C)(C)OC=2C(=CC=CC=2)Cl)CCC1(N(C)C)CC1=CC=CC=C1C VQEJOMSIOUKSJL-UHFFFAOYSA-N 0.000 claims description 2
- YQGNJLUUKRLKQR-UHFFFAOYSA-N 2-(2-chlorophenoxy)-n-[4-(dimethylamino)-4-[(4-fluorophenyl)methyl]cyclohexyl]-2-methylpropanamide Chemical compound C1CC(NC(=O)C(C)(C)OC=2C(=CC=CC=2)Cl)CCC1(N(C)C)CC1=CC=C(F)C=C1 YQGNJLUUKRLKQR-UHFFFAOYSA-N 0.000 claims description 2
- CBGSSETUNYMNRL-UHFFFAOYSA-N 2-(2-chlorophenoxy)-n-[4-[(2-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-2-methylpropanamide Chemical compound C1CC(NC(=O)C(C)(C)OC=2C(=CC=CC=2)Cl)CCC1(N(C)C)CC1=CC=CC=C1Cl CBGSSETUNYMNRL-UHFFFAOYSA-N 0.000 claims description 2
- CQLVAECGLDERDV-UHFFFAOYSA-N 2-(3-chlorophenoxy)-n-[4-(dimethylamino)-4-(2-phenylethyl)cyclohexyl]acetamide Chemical compound C1CC(NC(=O)COC=2C=C(Cl)C=CC=2)CCC1(N(C)C)CCC1=CC=CC=C1 CQLVAECGLDERDV-UHFFFAOYSA-N 0.000 claims description 2
- VCXOHALNLRJWSD-UHFFFAOYSA-N 2-(3-chlorophenoxy)-n-[4-(dimethylamino)-4-[(2-fluorophenyl)methyl]cyclohexyl]acetamide Chemical compound C1CC(NC(=O)COC=2C=C(Cl)C=CC=2)CCC1(N(C)C)CC1=CC=CC=C1F VCXOHALNLRJWSD-UHFFFAOYSA-N 0.000 claims description 2
- FOTYLDSFQFFPPE-UHFFFAOYSA-N 2-(3-chlorophenoxy)-n-[4-(dimethylamino)-4-[(3-fluorophenyl)methyl]cyclohexyl]acetamide Chemical compound C1CC(NC(=O)COC=2C=C(Cl)C=CC=2)CCC1(N(C)C)CC1=CC=CC(F)=C1 FOTYLDSFQFFPPE-UHFFFAOYSA-N 0.000 claims description 2
- VFNNBNRYSJGXPZ-UHFFFAOYSA-N 2-(3-chlorophenoxy)-n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]acetamide Chemical compound C1CC(NC(=O)COC=2C=C(Cl)C=CC=2)CCC1(N(C)C)CC1=CC=CC(C)=C1 VFNNBNRYSJGXPZ-UHFFFAOYSA-N 0.000 claims description 2
- FLTRHCVJYHUDML-UHFFFAOYSA-N 2-(3-chlorophenoxy)-n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]acetamide Chemical compound C1CC(NC(=O)COC=2C=C(Cl)C=CC=2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 FLTRHCVJYHUDML-UHFFFAOYSA-N 0.000 claims description 2
- FMCRXIMZNXOPBS-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-[4-(dimethylamino)-4-(2-phenylethyl)cyclohexyl]acetamide Chemical compound C1CC(NC(=O)COC=2C=CC(Cl)=CC=2)CCC1(N(C)C)CCC1=CC=CC=C1 FMCRXIMZNXOPBS-UHFFFAOYSA-N 0.000 claims description 2
- BLPOXRONFFQGIE-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-[4-(dimethylamino)-4-[(2-fluorophenyl)methyl]cyclohexyl]acetamide Chemical compound C1CC(NC(=O)COC=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=CC=C1F BLPOXRONFFQGIE-UHFFFAOYSA-N 0.000 claims description 2
- QLJPROYQGCVPNE-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-[4-(dimethylamino)-4-[(2-methylphenyl)methyl]cyclohexyl]acetamide Chemical compound C1CC(NC(=O)COC=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=CC=C1C QLJPROYQGCVPNE-UHFFFAOYSA-N 0.000 claims description 2
- HNWQQRSFJPCOCK-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-[4-(dimethylamino)-4-[(3-fluorophenyl)methyl]cyclohexyl]acetamide Chemical compound C1CC(NC(=O)COC=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=CC(F)=C1 HNWQQRSFJPCOCK-UHFFFAOYSA-N 0.000 claims description 2
- PWQHANLDAHMRAL-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]acetamide Chemical compound C1CC(NC(=O)COC=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=CC(C)=C1 PWQHANLDAHMRAL-UHFFFAOYSA-N 0.000 claims description 2
- GAVDPWVFGOCCQK-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]acetamide Chemical compound C1CC(NC(=O)COC=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=C(C)C=C1 GAVDPWVFGOCCQK-UHFFFAOYSA-N 0.000 claims description 2
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- HLEZTSOWHKQDDG-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]acetamide Chemical compound C1CC(NC(=O)COC=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=C(Cl)C=C1 HLEZTSOWHKQDDG-UHFFFAOYSA-N 0.000 claims description 2
- SJIKWGBWYQHRKN-UHFFFAOYSA-N 2-anilino-n-(4-benzyl-4-piperidin-1-ylcyclohexyl)benzamide Chemical compound C=1C=CC=C(NC=2C=CC=CC=2)C=1C(=O)NC(CC1)CCC1(N1CCCCC1)CC1=CC=CC=C1 SJIKWGBWYQHRKN-UHFFFAOYSA-N 0.000 claims description 2
- RRHRGCLKLFLZIF-UHFFFAOYSA-N 2-anilino-n-(4-morpholin-4-yl-4-phenylcyclohexyl)benzamide Chemical compound C=1C=CC=C(NC=2C=CC=CC=2)C=1C(=O)NC(CC1)CCC1(C=1C=CC=CC=1)N1CCOCC1 RRHRGCLKLFLZIF-UHFFFAOYSA-N 0.000 claims description 2
- YSJWGVSKJAYQHC-UHFFFAOYSA-N 2-anilino-n-(4-phenyl-4-piperidin-1-ylcyclohexyl)benzamide Chemical compound C=1C=CC=C(NC=2C=CC=CC=2)C=1C(=O)NC(CC1)CCC1(C=1C=CC=CC=1)N1CCCCC1 YSJWGVSKJAYQHC-UHFFFAOYSA-N 0.000 claims description 2
- SNSGNMVQAUVRIM-UHFFFAOYSA-N 2-anilino-n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]benzamide Chemical compound C1CC(NC(=O)C=2C(=CC=CC=2)NC=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC(C)=C1 SNSGNMVQAUVRIM-UHFFFAOYSA-N 0.000 claims description 2
- ZFYIIYXJMNASEP-UHFFFAOYSA-N 2-anilino-n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]benzamide Chemical compound C1CC(NC(=O)C=2C(=CC=CC=2)NC=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 ZFYIIYXJMNASEP-UHFFFAOYSA-N 0.000 claims description 2
- COKKOSQWKFUHKU-UHFFFAOYSA-N 2-benzylsulfanyl-n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]acetamide Chemical compound C1CC(NC(=O)CSCC=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC(C)=C1 COKKOSQWKFUHKU-UHFFFAOYSA-N 0.000 claims description 2
- IEOQFUSXILZBLH-UHFFFAOYSA-N 2-benzylsulfanyl-n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]acetamide Chemical compound C1CC(NC(=O)CSCC=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=C(C)C=C1 IEOQFUSXILZBLH-UHFFFAOYSA-N 0.000 claims description 2
- SJTHZIFYQDBSFI-UHFFFAOYSA-N 2-benzylsulfanyl-n-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]acetamide Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)CSCC1=CC=CC=C1 SJTHZIFYQDBSFI-UHFFFAOYSA-N 0.000 claims description 2
- YIKZZHGEJGLWAX-UHFFFAOYSA-N 2-benzylsulfanyl-n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]acetamide Chemical compound C1CC(NC(=O)CSCC=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 YIKZZHGEJGLWAX-UHFFFAOYSA-N 0.000 claims description 2
- URULLEPNGZEOHH-UHFFFAOYSA-N 2-benzylsulfanyl-n-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]acetamide Chemical compound C1CC(NC(=O)CSCC=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=C(Cl)C=C1 URULLEPNGZEOHH-UHFFFAOYSA-N 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
- ZZDZSCXEQDOMQX-UHFFFAOYSA-N 2-phenoxy-n-(4-phenyl-4-piperidin-1-ylcyclohexyl)butanamide Chemical compound C1CC(C=2C=CC=CC=2)(N2CCCCC2)CCC1NC(=O)C(CC)OC1=CC=CC=C1 ZZDZSCXEQDOMQX-UHFFFAOYSA-N 0.000 claims description 2
- SRJMPYHYMUJMJV-UHFFFAOYSA-N 3-(3-methoxy-4-phenylmethoxyphenyl)-n-(4-phenyl-4-piperidin-1-ylcyclohexyl)prop-2-enamide Chemical compound C=1C=C(OCC=2C=CC=CC=2)C(OC)=CC=1C=CC(=O)NC(CC1)CCC1(C=1C=CC=CC=1)N1CCCCC1 SRJMPYHYMUJMJV-UHFFFAOYSA-N 0.000 claims description 2
- BUUMUMAMQBYDNK-UHFFFAOYSA-N 3-[[4-(dimethylamino)-4-[(2-fluorophenyl)methyl]cyclohexyl]carbamoyl]-7-methoxy-7-oxoheptanoic acid Chemical compound C1CC(NC(=O)C(CC(O)=O)CCCC(=O)OC)CCC1(N(C)C)CC1=CC=CC=C1F BUUMUMAMQBYDNK-UHFFFAOYSA-N 0.000 claims description 2
- ZDQRTQLNMGNCCI-UHFFFAOYSA-N 3-[[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]carbamoyl]-7-methoxy-7-oxoheptanoic acid Chemical compound C1CC(NC(=O)C(CC(O)=O)CCCC(=O)OC)CCC1(N(C)C)CC1=CC=C(C)C=C1 ZDQRTQLNMGNCCI-UHFFFAOYSA-N 0.000 claims description 2
- ZTKRDEJBDAZISE-UHFFFAOYSA-N 3-[[4-[(2-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]carbamoyl]-7-methoxy-7-oxoheptanoic acid Chemical compound C1CC(NC(=O)C(CC(O)=O)CCCC(=O)OC)CCC1(N(C)C)CC1=CC=CC=C1Cl ZTKRDEJBDAZISE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- LKBAKAWPCGNSHY-UHFFFAOYSA-N 4-(4-chloro-2-methylphenoxy)-n-(4-morpholin-4-yl-4-phenylcyclohexyl)butanamide Chemical compound CC1=CC(Cl)=CC=C1OCCCC(=O)NC1CCC(C=2C=CC=CC=2)(N2CCOCC2)CC1 LKBAKAWPCGNSHY-UHFFFAOYSA-N 0.000 claims description 2
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- JDCBJBCHMQCIER-UHFFFAOYSA-N 4-chloro-n-[2-[4-[1-[[4-(dimethylamino)-4-[(2-fluorophenyl)methyl]cyclohexyl]amino]-2-methyl-1-oxopropan-2-yl]oxyphenyl]ethyl]benzamide Chemical compound C1CC(NC(=O)C(C)(C)OC=2C=CC(CCNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CCC1(N(C)C)CC1=CC=CC=C1F JDCBJBCHMQCIER-UHFFFAOYSA-N 0.000 claims description 2
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- JEZITFKUYKKOKZ-UHFFFAOYSA-N [2-[[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]amino]-2-oxo-1-phenylethyl] acetate Chemical compound C1CC(NC(=O)C(OC(C)=O)C=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=C(C)C=C1 JEZITFKUYKKOKZ-UHFFFAOYSA-N 0.000 claims description 2
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- OREZQUBJZVSRJJ-UHFFFAOYSA-N [2-[[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]carbamoyl]phenyl]methyl benzoate Chemical compound C1CC(NC(=O)C=2C(=CC=CC=2)COC(=O)C=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=C(C)C=C1 OREZQUBJZVSRJJ-UHFFFAOYSA-N 0.000 claims description 2
- MHFRYAJCPRSTCX-UHFFFAOYSA-N [2-[[4-(dimethylamino)-4-phenylcyclohexyl]carbamoyl]phenyl]methyl benzoate Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)C1=CC=CC=C1COC(=O)C1=CC=CC=C1 MHFRYAJCPRSTCX-UHFFFAOYSA-N 0.000 claims description 2
- CRVYBWAEVAFIGG-UHFFFAOYSA-N [2-[[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]amino]-2-oxo-1-phenylethyl] acetate Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)C(OC(C)=O)C1=CC=CC=C1 CRVYBWAEVAFIGG-UHFFFAOYSA-N 0.000 claims description 2
- NZRLJBYVQVLMCR-UHFFFAOYSA-N [2-[[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]amino]-2-oxoethyl] acetate Chemical compound C=1C=CSC=1C1(N(C)C)CCC(NC(=O)COC(C)=O)CC1 NZRLJBYVQVLMCR-UHFFFAOYSA-N 0.000 claims description 2
- BKGQURBBLVZXPE-UHFFFAOYSA-N [2-[[4-[(2-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]amino]-2-oxo-1-phenylethyl] acetate Chemical compound C1CC(NC(=O)C(OC(C)=O)C=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC=C1Cl BKGQURBBLVZXPE-UHFFFAOYSA-N 0.000 claims description 2
- WJLIDLSGDYLZGQ-UHFFFAOYSA-N [2-[[4-[(2-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]amino]-2-oxoethyl] acetate Chemical compound C=1C=CC=C(Cl)C=1CC1(N(C)C)CCC(NC(=O)COC(C)=O)CC1 WJLIDLSGDYLZGQ-UHFFFAOYSA-N 0.000 claims description 2
- BMHAWXDIPHJHDZ-UHFFFAOYSA-N [2-[[4-[(2-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]carbamoyl]phenyl]methyl benzoate Chemical compound C1CC(NC(=O)C=2C(=CC=CC=2)COC(=O)C=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC=C1Cl BMHAWXDIPHJHDZ-UHFFFAOYSA-N 0.000 claims description 2
- MQGWHOZTSNBMOS-UHFFFAOYSA-N [2-[[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]amino]-2-oxo-1-phenylethyl] acetate Chemical compound C1CC(NC(=O)C(OC(C)=O)C=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 MQGWHOZTSNBMOS-UHFFFAOYSA-N 0.000 claims description 2
- DLASRAUIRXIXCC-UHFFFAOYSA-N [2-[[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]amino]-2-oxoethyl] acetate Chemical compound C=1C=CC(Cl)=CC=1CC1(N(C)C)CCC(NC(=O)COC(C)=O)CC1 DLASRAUIRXIXCC-UHFFFAOYSA-N 0.000 claims description 2
- HALVIRKCJMPMPS-UHFFFAOYSA-N [2-[[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]carbamoyl]phenyl]methyl benzoate Chemical compound C1CC(NC(=O)C=2C(=CC=CC=2)COC(=O)C=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 HALVIRKCJMPMPS-UHFFFAOYSA-N 0.000 claims description 2
- DCBSTDWBSQFPHX-UHFFFAOYSA-N [2-[[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]amino]-2-oxo-1-phenylethyl] acetate Chemical compound C1CC(NC(=O)C(OC(C)=O)C=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=C(Cl)C=C1 DCBSTDWBSQFPHX-UHFFFAOYSA-N 0.000 claims description 2
- STQBDNSYKSZRCC-UHFFFAOYSA-N [2-[[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]amino]-2-oxoethyl] acetate Chemical compound C=1C=C(Cl)C=CC=1CC1(N(C)C)CCC(NC(=O)COC(C)=O)CC1 STQBDNSYKSZRCC-UHFFFAOYSA-N 0.000 claims description 2
- OURXQAXCXLZDGB-UHFFFAOYSA-N [2-[[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]carbamoyl]phenyl]methyl benzoate Chemical compound C1CC(NC(=O)C=2C(=CC=CC=2)COC(=O)C=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=C(Cl)C=C1 OURXQAXCXLZDGB-UHFFFAOYSA-N 0.000 claims description 2
- DPIXLWLTAFSHJG-UHFFFAOYSA-N [2-[[4-benzyl-4-(dimethylamino)cyclohexyl]amino]-2-oxo-1-phenylethyl] acetate Chemical compound C1CC(NC(=O)C(OC(C)=O)C=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC=C1 DPIXLWLTAFSHJG-UHFFFAOYSA-N 0.000 claims description 2
- DOCHENLMQFEHNF-UHFFFAOYSA-N [2-[[4-benzyl-4-(dimethylamino)cyclohexyl]carbamoyl]phenyl]methyl benzoate Chemical compound C1CC(NC(=O)C=2C(=CC=CC=2)COC(=O)C=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC=C1 DOCHENLMQFEHNF-UHFFFAOYSA-N 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
- 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
- 239000008280 blood Substances 0.000 claims description 2
- 210000004369 blood Anatomy 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 206010013663 drug dependence Diseases 0.000 claims description 2
- 230000029142 excretion Effects 0.000 claims description 2
- 239000003193 general anesthetic agent Substances 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
- YOBIAKZQVXNNEU-UHFFFAOYSA-N methyl 5-[(4-morpholin-4-yl-4-phenylcyclohexyl)amino]-5-oxopentanoate Chemical compound C1CC(NC(=O)CCCC(=O)OC)CCC1(C=1C=CC=CC=1)N1CCOCC1 YOBIAKZQVXNNEU-UHFFFAOYSA-N 0.000 claims description 2
- UAUYRGZOTUEQNM-UHFFFAOYSA-N methyl 5-[[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexyl]amino]-5-oxopentanoate Chemical compound C1CC(NC(=O)CCCC(=O)OC)CCC1(N(C)C)C1=CC=CC(F)=C1 UAUYRGZOTUEQNM-UHFFFAOYSA-N 0.000 claims description 2
- MILSOZPQKDJINX-UHFFFAOYSA-N methyl 5-[[4-(dimethylamino)-4-[(2-fluorophenyl)methyl]cyclohexyl]amino]-5-oxopentanoate Chemical compound C1CC(NC(=O)CCCC(=O)OC)CCC1(N(C)C)CC1=CC=CC=C1F MILSOZPQKDJINX-UHFFFAOYSA-N 0.000 claims description 2
- INPMIHFSMKRCQO-UHFFFAOYSA-N methyl 5-[[4-(dimethylamino)-4-[(3-fluorophenyl)methyl]cyclohexyl]amino]-5-oxopentanoate Chemical compound C1CC(NC(=O)CCCC(=O)OC)CCC1(N(C)C)CC1=CC=CC(F)=C1 INPMIHFSMKRCQO-UHFFFAOYSA-N 0.000 claims description 2
- LWJNNMXNXLAGQP-UHFFFAOYSA-N methyl 5-[[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]amino]-5-oxopentanoate Chemical compound C1CC(NC(=O)CCCC(=O)OC)CCC1(N(C)C)CC1=CC=CC(C)=C1 LWJNNMXNXLAGQP-UHFFFAOYSA-N 0.000 claims description 2
- SJTAHPNDFPKKHG-UHFFFAOYSA-N methyl 5-[[4-(dimethylamino)-4-[(4-fluorophenyl)methyl]cyclohexyl]amino]-5-oxopentanoate Chemical compound C1CC(NC(=O)CCCC(=O)OC)CCC1(N(C)C)CC1=CC=C(F)C=C1 SJTAHPNDFPKKHG-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/18—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides
- C07C235/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/36—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/62—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
- C07C235/74—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of a saturated carbon skeleton
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/38—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to a carbon atom of a ring other than a six-membered aromatic ring
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- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/60—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by carboxyl groups
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- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- Organic Chemistry (AREA)
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004023506A DE102004023506A1 (de) | 2004-05-10 | 2004-05-10 | Kettenverlängerte substituierte Cyclohexyl-1,4-diamin-Derivate |
| DE102004023506.6 | 2004-05-10 | ||
| PCT/EP2005/004912 WO2005110975A1 (de) | 2004-05-10 | 2005-05-06 | Kettenverlängerte substituierte cyclohexyl-1,4-diamin-derivate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007536322A JP2007536322A (ja) | 2007-12-13 |
| JP2007536322A5 JP2007536322A5 (https=) | 2012-03-15 |
| JP5037336B2 true JP5037336B2 (ja) | 2012-09-26 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2007512032A Expired - Fee Related JP5037336B2 (ja) | 2004-05-10 | 2005-05-06 | 鎖長が延ばされ、置換されたシクロヘキシル−1,4−ジアミンの酸誘導体 |
Country Status (6)
| Country | Link |
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| US (1) | US7786328B2 (https=) |
| EP (1) | EP1747191A1 (https=) |
| JP (1) | JP5037336B2 (https=) |
| CA (1) | CA2566219C (https=) |
| DE (1) | DE102004023506A1 (https=) |
| WO (1) | WO2005110975A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004023635A1 (de) * | 2004-05-10 | 2006-04-13 | Grünenthal GmbH | Heteroarylsubstituierte Cyclohexyl-1,4-diamin-Derivate |
| AU2009228647B2 (en) | 2008-03-27 | 2013-07-04 | Grunenthal Gmbh | Substituted spirocyclic cyclohexane derivatives |
| 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 |
| 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. |
| ES2464102T3 (es) | 2008-03-27 | 2014-05-30 | Grünenthal GmbH | Derivados de 4-aminociclohexano sustituidos |
| CN102046591B (zh) | 2008-03-27 | 2014-12-03 | 格吕伦塔尔有限公司 | 羟甲基环己胺 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4656182A (en) * | 1983-12-06 | 1987-04-07 | Warner-Lambert Company | Substituted trans-1,2-diaminocyclohexyl amide compounds |
| CA2373855A1 (en) * | 1999-05-12 | 2000-11-23 | Solvay Pharmaceuticals B.V. | Method of treating psychotic disorders |
| FR2797874B1 (fr) * | 1999-08-27 | 2002-03-29 | Adir | Nouveaux derives de la pyridine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| 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 |
| US7354932B2 (en) | 2001-12-21 | 2008-04-08 | Anormed, Inc. | Chemokine receptor binding heterocyclic compounds with enhanced efficacy |
| EP1458704A1 (en) * | 2001-12-21 | 2004-09-22 | H. Lundbeck A/S | Aminoindane derivatives as serotonin and norepinephrine uptake inhibitors |
| DE10252665A1 (de) * | 2002-11-11 | 2004-06-03 | Grünenthal GmbH | 4-Aminomethyl-1-aryl-cyclohexylamin-Derivate |
| DE10252650A1 (de) | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Cyclohexyl-Harnstoff-Derivate |
| JP2007522129A (ja) | 2004-01-21 | 2007-08-09 | エラン ファーマシューティカルズ,インコーポレイテッド | アスパラギン酸プロテアーゼ阻害薬を用いるアミロイドーシスの処置方法 |
| EP1736467A4 (en) * | 2004-04-06 | 2009-07-01 | Dainippon Sumitomo Pharma Co | NEW SULFONIC ACID AMID DERIVATIVE |
| DE102004023635A1 (de) * | 2004-05-10 | 2006-04-13 | Grünenthal GmbH | Heteroarylsubstituierte Cyclohexyl-1,4-diamin-Derivate |
-
2004
- 2004-05-10 DE DE102004023506A patent/DE102004023506A1/de not_active Withdrawn
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2005
- 2005-05-06 WO PCT/EP2005/004912 patent/WO2005110975A1/de not_active Ceased
- 2005-05-06 CA CA2566219A patent/CA2566219C/en not_active Expired - Fee Related
- 2005-05-06 EP EP05747800A patent/EP1747191A1/de not_active Withdrawn
- 2005-05-06 JP JP2007512032A patent/JP5037336B2/ja not_active Expired - Fee Related
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2006
- 2006-11-09 US US11/594,953 patent/US7786328B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005110975A1 (de) | 2005-11-24 |
| DE102004023506A1 (de) | 2005-12-01 |
| US20070281954A1 (en) | 2007-12-06 |
| EP1747191A1 (de) | 2007-01-31 |
| US7786328B2 (en) | 2010-08-31 |
| JP2007536322A (ja) | 2007-12-13 |
| CA2566219C (en) | 2012-08-07 |
| CA2566219A1 (en) | 2005-11-24 |
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