JP2007536317A5 - - Google Patents
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- Publication number
- JP2007536317A5 JP2007536317A5 JP2007512027A JP2007512027A JP2007536317A5 JP 2007536317 A5 JP2007536317 A5 JP 2007536317A5 JP 2007512027 A JP2007512027 A JP 2007512027A JP 2007512027 A JP2007512027 A JP 2007512027A JP 2007536317 A5 JP2007536317 A5 JP 2007536317A5
- Authority
- JP
- Japan
- Prior art keywords
- cyclohexyl
- dimethylamino
- phenyl
- benzyl
- oxo
- 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
- -1 2- (3-Benzoyl-phenyl) -N- [4-dimethylamino-4- (2-fluoro-benzyl) -cyclohexyl] -propionamide 5-oxo-5-phenyl-valeric acid [4-dimethylamino-4 -(2-fluoro-benzyl) -cyclohexyl] -amide Chemical compound 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 8
- 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 7
- 239000002253 acid Substances 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- VCUSYDGPHVVMDW-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[4-(dimethylamino)-4-phenylcyclohexyl]-4-oxobutanamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)CCC(=O)C1=CC=C(Cl)C=C1 VCUSYDGPHVVMDW-UHFFFAOYSA-N 0.000 claims description 4
- 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
- 206010012335 Dependence Diseases 0.000 claims description 3
- 208000016285 Movement disease Diseases 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- 208000010877 cognitive disease Diseases 0.000 claims description 3
- 239000003193 general anesthetic agent Substances 0.000 claims description 3
- 229940005483 opioid analgesics Drugs 0.000 claims description 3
- 208000011117 substance-related disease Diseases 0.000 claims description 3
- QRUCELXGSAWBOY-UHFFFAOYSA-N 2-(3-acetyl-2,2-dimethylcyclobutyl)-N-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]acetamide Chemical compound C(C)(=O)C1C(C(C1)CC(=O)NC1CCC(CC1)(N(C)C)CC1=CC=C(C=C1)Cl)(C)C QRUCELXGSAWBOY-UHFFFAOYSA-N 0.000 claims description 2
- XKFGLKKOGQNCDA-UHFFFAOYSA-N 2-(3-acetyl-2,2-dimethylcyclobutyl)-n-(4-benzyl-4-piperidin-1-ylcyclohexyl)acetamide Chemical compound CC1(C)C(C(=O)C)CC1CC(=O)NC1CCC(CC=2C=CC=CC=2)(N2CCCCC2)CC1 XKFGLKKOGQNCDA-UHFFFAOYSA-N 0.000 claims description 2
- PBLADULXZGPZEM-UHFFFAOYSA-N 2-(3-acetyl-2,2-dimethylcyclobutyl)-n-[4-(dimethylamino)-4-[(2-fluorophenyl)methyl]cyclohexyl]acetamide Chemical compound C1CC(NC(=O)CC2C(C(C(C)=O)C2)(C)C)CCC1(N(C)C)CC1=CC=CC=C1F PBLADULXZGPZEM-UHFFFAOYSA-N 0.000 claims description 2
- KMGIEOGQXHBWRZ-UHFFFAOYSA-N 2-(3-acetyl-2,2-dimethylcyclobutyl)-n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]acetamide Chemical compound C1CC(NC(=O)CC2C(C(C(C)=O)C2)(C)C)CCC1(N(C)C)CC1=CC=CC(C)=C1 KMGIEOGQXHBWRZ-UHFFFAOYSA-N 0.000 claims description 2
- CGMPDBZLLYKFHT-UHFFFAOYSA-N 2-(3-acetyl-2,2-dimethylcyclobutyl)-n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]acetamide Chemical compound C1CC(NC(=O)CC2C(C(C(C)=O)C2)(C)C)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 CGMPDBZLLYKFHT-UHFFFAOYSA-N 0.000 claims description 2
- BIVISMFVNZSWFM-UHFFFAOYSA-N 2-(3-acetyl-2,2-dimethylcyclobutyl)-n-[4-benzyl-4-(dimethylamino)cyclohexyl]acetamide Chemical compound C1CC(NC(=O)CC2C(C(C(C)=O)C2)(C)C)CCC1(N(C)C)CC1=CC=CC=C1 BIVISMFVNZSWFM-UHFFFAOYSA-N 0.000 claims description 2
- LBUGDZKZSTZSPU-UHFFFAOYSA-N 2-(3-benzoylphenyl)-n-(4-benzyl-4-pyrrolidin-1-ylcyclohexyl)propanamide Chemical compound C=1C=CC(C(=O)C=2C=CC=CC=2)=CC=1C(C)C(=O)NC(CC1)CCC1(N1CCCC1)CC1=CC=CC=C1 LBUGDZKZSTZSPU-UHFFFAOYSA-N 0.000 claims description 2
- AGNBRSNIQDMPLT-UHFFFAOYSA-N 2-(3-benzoylphenyl)-n-(4-phenyl-4-piperidin-1-ylcyclohexyl)propanamide Chemical compound C=1C=CC(C(=O)C=2C=CC=CC=2)=CC=1C(C)C(=O)NC(CC1)CCC1(C=1C=CC=CC=1)N1CCCCC1 AGNBRSNIQDMPLT-UHFFFAOYSA-N 0.000 claims description 2
- OWTRFTYCXTZHNJ-UHFFFAOYSA-N 2-(3-benzoylphenyl)-n-[4-(dimethylamino)-4-(2-phenylethyl)cyclohexyl]propanamide Chemical compound C=1C=CC(C(=O)C=2C=CC=CC=2)=CC=1C(C)C(=O)NC(CC1)CCC1(N(C)C)CCC1=CC=CC=C1 OWTRFTYCXTZHNJ-UHFFFAOYSA-N 0.000 claims description 2
- VYAKFVOLVPXKOM-UHFFFAOYSA-N 2-(3-benzoylphenyl)-n-[4-(dimethylamino)-4-[(2-methylphenyl)methyl]cyclohexyl]propanamide Chemical compound C=1C=CC(C(=O)C=2C=CC=CC=2)=CC=1C(C)C(=O)NC(CC1)CCC1(N(C)C)CC1=CC=CC=C1C VYAKFVOLVPXKOM-UHFFFAOYSA-N 0.000 claims description 2
- NZXXHDHXPVJQQD-UHFFFAOYSA-N 2-(3-benzoylphenyl)-n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]propanamide Chemical compound C=1C=CC(C(=O)C=2C=CC=CC=2)=CC=1C(C)C(=O)NC(CC1)CCC1(N(C)C)CC1=CC=CC(C)=C1 NZXXHDHXPVJQQD-UHFFFAOYSA-N 0.000 claims description 2
- YTOGHMWQACIDSK-UHFFFAOYSA-N 2-(3-benzoylphenyl)-n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]propanamide Chemical compound C=1C=CC(C(=O)C=2C=CC=CC=2)=CC=1C(C)C(=O)NC(CC1)CCC1(N(C)C)CC1=CC=C(C)C=C1 YTOGHMWQACIDSK-UHFFFAOYSA-N 0.000 claims description 2
- VRMJHEJJIQXHJX-UHFFFAOYSA-N 2-(3-benzoylphenyl)-n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]propanamide Chemical compound C=1C=CC(C(=O)C=2C=CC=CC=2)=CC=1C(C)C(=O)NC(CC1)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 VRMJHEJJIQXHJX-UHFFFAOYSA-N 0.000 claims description 2
- QXDKUFHYJVHZBL-UHFFFAOYSA-N 2-(3-benzoylphenyl)-n-[4-benzyl-4-(dimethylamino)cyclohexyl]propanamide Chemical compound C=1C=CC(C(=O)C=2C=CC=CC=2)=CC=1C(C)C(=O)NC(CC1)CCC1(N(C)C)CC1=CC=CC=C1 QXDKUFHYJVHZBL-UHFFFAOYSA-N 0.000 claims description 2
- WCKUHSJENYGSEL-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-(4-morpholin-4-yl-4-phenylcyclohexyl)-4-oxobutanamide Chemical compound C1=CC(Cl)=CC=C1C(=O)CCC(=O)NC1CCC(C=2C=CC=CC=2)(N2CCOCC2)CC1 WCKUHSJENYGSEL-UHFFFAOYSA-N 0.000 claims description 2
- XFMIBQVLHKDRJB-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[4-(dimethylamino)-4-[(3-fluorophenyl)methyl]cyclohexyl]-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)C=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=CC(F)=C1 XFMIBQVLHKDRJB-UHFFFAOYSA-N 0.000 claims description 2
- MBJMGSOAYZIFRE-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)C=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=C(C)C=C1 MBJMGSOAYZIFRE-UHFFFAOYSA-N 0.000 claims description 2
- OFXTXOFRRFIADV-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[4-[(2-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)C=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=CC=C1Cl OFXTXOFRRFIADV-UHFFFAOYSA-N 0.000 claims description 2
- IHAGUOIXHBTIPF-UHFFFAOYSA-N 4-(4-fluorophenyl)-4-oxo-n-(4-phenyl-4-piperidin-1-ylcyclohexyl)butanamide Chemical compound C1=CC(F)=CC=C1C(=O)CCC(=O)NC1CCC(C=2C=CC=CC=2)(N2CCCCC2)CC1 IHAGUOIXHBTIPF-UHFFFAOYSA-N 0.000 claims description 2
- ZLNGKMMTTDNAQE-UHFFFAOYSA-N 4-oxo-4-phenyl-n-(4-phenyl-4-piperidin-1-ylcyclohexyl)butanamide Chemical compound C1CC(C=2C=CC=CC=2)(N2CCCCC2)CCC1NC(=O)CCC(=O)C1=CC=CC=C1 ZLNGKMMTTDNAQE-UHFFFAOYSA-N 0.000 claims description 2
- SHKWSBAVRQZYLE-UHFFFAOYSA-N 5-oxo-5-phenylpentanoic acid Chemical compound OC(=O)CCCC(=O)C1=CC=CC=C1 SHKWSBAVRQZYLE-UHFFFAOYSA-N 0.000 claims description 2
- 208000019901 Anxiety disease Diseases 0.000 claims description 2
- 206010006895 Cachexia Diseases 0.000 claims description 2
- 206010011878 Deafness Diseases 0.000 claims description 2
- 206010012735 Diarrhoea Diseases 0.000 claims description 2
- 206010013654 Drug abuse Diseases 0.000 claims description 2
- 206010020772 Hypertension Diseases 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- KZDFWALHBNDHDR-UHFFFAOYSA-N N-(4-benzyl-4-piperidin-1-ylcyclohexyl)-4-oxo-4-phenylbutanamide N-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-4-(4-fluorophenyl)-4-oxobutanamide Chemical compound CN(C)C1(Cc2ccc(C)cc2)CCC(CC1)NC(=O)CCC(=O)c1ccc(F)cc1.O=C(CCC(=O)c1ccccc1)NC1CCC(Cc2ccccc2)(CC1)N1CCCCC1 KZDFWALHBNDHDR-UHFFFAOYSA-N 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
- 239000000654 additive Substances 0.000 claims description 2
- 239000001961 anticonvulsive agent Substances 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
- 201000010099 disease Diseases 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 239000002934 diuretic Substances 0.000 claims description 2
- 229940030606 diuretics Drugs 0.000 claims description 2
- 206010015037 epilepsy Diseases 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
- 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
- LUMJDZUCCQIHEG-UHFFFAOYSA-N n-(4-benzyl-4-piperidin-1-ylcyclohexyl)-4-(4-fluorophenyl)-4-oxobutanamide Chemical compound C1=CC(F)=CC=C1C(=O)CCC(=O)NC1CCC(CC=2C=CC=CC=2)(N2CCCCC2)CC1 LUMJDZUCCQIHEG-UHFFFAOYSA-N 0.000 claims description 2
- RGQDZJZYMFOUCS-UHFFFAOYSA-N n-(4-morpholin-4-yl-4-phenylcyclohexyl)-6-oxoheptanamide Chemical compound C1CC(NC(=O)CCCCC(=O)C)CCC1(C=1C=CC=CC=1)N1CCOCC1 RGQDZJZYMFOUCS-UHFFFAOYSA-N 0.000 claims description 2
- JFKNRQNJJSINFK-UHFFFAOYSA-N n-[4-(dimethylamino)-4-(2-phenylethyl)cyclohexyl]-2-(1h-indol-3-yl)-2-oxoacetamide Chemical compound C1CC(NC(=O)C(=O)C=2C3=CC=CC=C3NC=2)CCC1(N(C)C)CCC1=CC=CC=C1 JFKNRQNJJSINFK-UHFFFAOYSA-N 0.000 claims description 2
- ZSBRUECKKQYGSW-UHFFFAOYSA-N n-[4-(dimethylamino)-4-(2-phenylethyl)cyclohexyl]-4-oxo-4-phenylbutanamide Chemical compound C1CC(NC(=O)CCC(=O)C=2C=CC=CC=2)CCC1(N(C)C)CCC1=CC=CC=C1 ZSBRUECKKQYGSW-UHFFFAOYSA-N 0.000 claims description 2
- OGWCCMHJLPUJGR-UHFFFAOYSA-N n-[4-(dimethylamino)-4-(2-phenylethyl)cyclohexyl]-5-oxo-5-phenylpentanamide Chemical compound C1CC(NC(=O)CCCC(=O)C=2C=CC=CC=2)CCC1(N(C)C)CCC1=CC=CC=C1 OGWCCMHJLPUJGR-UHFFFAOYSA-N 0.000 claims description 2
- NMBWYIGIOCHPFY-UHFFFAOYSA-N n-[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexyl]-2-(1h-indol-3-yl)-2-oxoacetamide Chemical compound C1CC(NC(=O)C(=O)C=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC(F)=C1 NMBWYIGIOCHPFY-UHFFFAOYSA-N 0.000 claims description 2
- XWKNYXKXHQRHLE-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(2-fluorophenyl)methyl]cyclohexyl]-2-(1h-indol-3-yl)-2-oxoacetamide Chemical compound C1CC(NC(=O)C(=O)C=2C3=CC=CC=C3NC=2)CCC1(N(C)C)CC1=CC=CC=C1F XWKNYXKXHQRHLE-UHFFFAOYSA-N 0.000 claims description 2
- HLBPWJMKNVREMM-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(2-fluorophenyl)methyl]cyclohexyl]-4-(4-fluorophenyl)-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)C=2C=CC(F)=CC=2)CCC1(N(C)C)CC1=CC=CC=C1F HLBPWJMKNVREMM-UHFFFAOYSA-N 0.000 claims description 2
- IZSLLPPEYGOFJF-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(2-methylphenyl)methyl]cyclohexyl]-4-oxo-4-phenylbutanamide Chemical compound C1CC(NC(=O)CCC(=O)C=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC=C1C IZSLLPPEYGOFJF-UHFFFAOYSA-N 0.000 claims description 2
- WSTAMKONIVHJQP-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(3-fluorophenyl)methyl]cyclohexyl]-4-(4-fluorophenyl)-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)C=2C=CC(F)=CC=2)CCC1(N(C)C)CC1=CC=CC(F)=C1 WSTAMKONIVHJQP-UHFFFAOYSA-N 0.000 claims description 2
- MIMCDTANDFLVIN-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-2-(1h-indol-3-yl)-2-oxoacetamide Chemical compound C1CC(NC(=O)C(=O)C=2C3=CC=CC=C3NC=2)CCC1(N(C)C)CC1=CC=CC(C)=C1 MIMCDTANDFLVIN-UHFFFAOYSA-N 0.000 claims description 2
- YAMVUYMTYOBGAK-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]-4-oxo-4-phenylbutanamide Chemical compound C1CC(NC(=O)CCC(=O)C=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC(C)=C1 YAMVUYMTYOBGAK-UHFFFAOYSA-N 0.000 claims description 2
- FZUKZMFYJKZBBM-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(4-fluorophenyl)methyl]cyclohexyl]-2-(1h-indol-3-yl)-2-oxoacetamide Chemical compound C1CC(NC(=O)C(=O)C=2C3=CC=CC=C3NC=2)CCC1(N(C)C)CC1=CC=C(F)C=C1 FZUKZMFYJKZBBM-UHFFFAOYSA-N 0.000 claims description 2
- ZSAQIGFEBHYDEX-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(4-fluorophenyl)methyl]cyclohexyl]-4-oxo-4-phenylbutanamide Chemical compound C1CC(NC(=O)CCC(=O)C=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=C(F)C=C1 ZSAQIGFEBHYDEX-UHFFFAOYSA-N 0.000 claims description 2
- JVAUXRJMHXNGIR-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-7-oxooctanamide Chemical compound C=1C=C(C)C=CC=1CC1(N(C)C)CCC(NC(=O)CCCCCC(C)=O)CC1 JVAUXRJMHXNGIR-UHFFFAOYSA-N 0.000 claims description 2
- KVBXMQNDDNSVRA-UHFFFAOYSA-N n-[4-(dimethylamino)-4-phenylcyclohexyl]-5-oxo-5-phenylpentanamide Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)CCCC(=O)C1=CC=CC=C1 KVBXMQNDDNSVRA-UHFFFAOYSA-N 0.000 claims description 2
- SCHWABGSWZDREQ-UHFFFAOYSA-N n-[4-(dimethylamino)-4-phenylcyclohexyl]-5-oxo-5-phenylpentanamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1NC(=O)CCCC(=O)C1=CC=CC=C1 SCHWABGSWZDREQ-UHFFFAOYSA-N 0.000 claims description 2
- ZPQMDFPMMVCQBY-UHFFFAOYSA-N n-[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]-4-(4-fluorophenyl)-4-oxobutanamide Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC1NC(=O)CCC(=O)C1=CC=C(F)C=C1 ZPQMDFPMMVCQBY-UHFFFAOYSA-N 0.000 claims description 2
- RHLZKILNPXAJQZ-UHFFFAOYSA-N n-[4-[(2-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-2-(1h-indol-3-yl)-2-oxoacetamide Chemical compound C1CC(NC(=O)C(=O)C=2C3=CC=CC=C3NC=2)CCC1(N(C)C)CC1=CC=CC=C1Cl RHLZKILNPXAJQZ-UHFFFAOYSA-N 0.000 claims description 2
- CJDZTTYBWFZFJH-UHFFFAOYSA-N n-[4-[(2-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-4-oxo-4-phenylbutanamide Chemical compound C1CC(NC(=O)CCC(=O)C=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC=C1Cl CJDZTTYBWFZFJH-UHFFFAOYSA-N 0.000 claims description 2
- CXRCODHKRPEEJG-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-4-(4-fluorophenyl)-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)C=2C=CC(F)=CC=2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 CXRCODHKRPEEJG-UHFFFAOYSA-N 0.000 claims description 2
- HAQKLYAYADKHMB-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-5-oxo-5-phenylpentanamide Chemical compound C1CC(NC(=O)CCCC(=O)C=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC(Cl)=C1 HAQKLYAYADKHMB-UHFFFAOYSA-N 0.000 claims description 2
- ZAEYRIJYCIRNJD-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-6-oxoheptanamide Chemical compound C=1C=CC(Cl)=CC=1CC1(N(C)C)CCC(NC(=O)CCCCC(C)=O)CC1 ZAEYRIJYCIRNJD-UHFFFAOYSA-N 0.000 claims description 2
- HDRSMTFDRVOREL-UHFFFAOYSA-N n-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-5-oxo-5-phenylpentanamide Chemical compound C1CC(NC(=O)CCCC(=O)C=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=C(Cl)C=C1 HDRSMTFDRVOREL-UHFFFAOYSA-N 0.000 claims description 2
- NACRCIBOZBLULL-UHFFFAOYSA-N n-[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]-6-oxoheptanamide Chemical compound C=1C=C(Cl)C=CC=1CC1(N(C)C)CCC(NC(=O)CCCCC(C)=O)CC1 NACRCIBOZBLULL-UHFFFAOYSA-N 0.000 claims description 2
- MKGVHMKZVWUFKR-UHFFFAOYSA-N n-[4-benzyl-4-(dimethylamino)cyclohexyl]-4-(4-chlorophenyl)-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)C=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=CC=C1 MKGVHMKZVWUFKR-UHFFFAOYSA-N 0.000 claims description 2
- OHOYASBFQBCRDM-UHFFFAOYSA-N n-[4-benzyl-4-(dimethylamino)cyclohexyl]-4-(4-fluorophenyl)-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)C=2C=CC(F)=CC=2)CCC1(N(C)C)CC1=CC=CC=C1 OHOYASBFQBCRDM-UHFFFAOYSA-N 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
- 239000002858 neurotransmitter agent Substances 0.000 claims description 2
- 230000001777 nootropic effect Effects 0.000 claims description 2
- 235000015816 nutrient absorption Nutrition 0.000 claims description 2
- 239000000014 opioid analgesic Substances 0.000 claims description 2
- 229940052318 opioid anesthetics Drugs 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
- 208000002193 Pain Diseases 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- 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 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 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
- 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
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 1
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 1
- 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 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 208000009132 Catalepsy Diseases 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 208000001953 Hypotension Diseases 0.000 claims 1
- 208000020358 Learning disease Diseases 0.000 claims 1
- 208000026139 Memory disease Diseases 0.000 claims 1
- 229910052776 Thorium Inorganic materials 0.000 claims 1
- 206010047853 Waxy flexibility Diseases 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 208000005298 acute pain Diseases 0.000 claims 1
- 230000003444 anaesthetic effect Effects 0.000 claims 1
- 230000001773 anti-convulsant effect Effects 0.000 claims 1
- 229960003965 antiepileptics Drugs 0.000 claims 1
- 230000004596 appetite loss Effects 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 230000000747 cardiac effect Effects 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical class NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 claims 1
- 230000029142 excretion Effects 0.000 claims 1
- 230000036543 hypotension Effects 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 201000003723 learning disability Diseases 0.000 claims 1
- 208000019017 loss of appetite Diseases 0.000 claims 1
- 235000021266 loss of appetite Nutrition 0.000 claims 1
- RJOZFODSLXLIQJ-UHFFFAOYSA-N n-[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]-4-oxo-4-phenylbutanamide Chemical compound C1CC(NC(=O)CCC(=O)C=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=C(C)C=C1 RJOZFODSLXLIQJ-UHFFFAOYSA-N 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- YUALQSSMNCNBMV-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[4-(dimethylamino)-4-[(2-methylphenyl)methyl]cyclohexyl]-4-oxobutanamide Chemical compound C1CC(NC(=O)CCC(=O)C=2C=CC(Cl)=CC=2)CCC1(N(C)C)CC1=CC=CC=C1C YUALQSSMNCNBMV-UHFFFAOYSA-N 0.000 description 1
- LOVVOOWEUPFPNM-UHFFFAOYSA-N CC1=CC=C(CC(CC2)(CCC2C(CC(C2=CC=CC=C2)=O)C(N)=O)N(C)C)C=C1 Chemical compound CC1=CC=C(CC(CC2)(CCC2C(CC(C2=CC=CC=C2)=O)C(N)=O)N(C)C)C=C1 LOVVOOWEUPFPNM-UHFFFAOYSA-N 0.000 description 1
- 0 CN(*)C(*)(CC1)CCC1N Chemical compound CN(*)C(*)(CC1)CCC1N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 208000028698 Cognitive impairment Diseases 0.000 description 1
- 208000017228 Gastrointestinal motility disease Diseases 0.000 description 1
- 229940035674 anesthetics Drugs 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 230000001598 anti-natriuretic effect Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 229940005530 anxiolytics Drugs 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical class OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 206010013663 drug dependence Diseases 0.000 description 1
- 206010027175 memory impairment Diseases 0.000 description 1
- 102000051367 mu Opioid Receptors Human genes 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 108020001612 μ-opioid receptors Proteins 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004023501A DE102004023501A1 (de) | 2004-05-10 | 2004-05-10 | Oxosubstituierte Cyclohexyl-1,4-diamin-Derivate |
| DE102004023501.5 | 2004-05-10 | ||
| PCT/EP2005/004907 WO2005110970A1 (de) | 2004-05-10 | 2005-05-06 | Oxosubstituierte cyclohexyl-1,4-diamin-derivate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007536317A JP2007536317A (ja) | 2007-12-13 |
| JP2007536317A5 true JP2007536317A5 (https=) | 2011-11-24 |
| JP4896009B2 JP4896009B2 (ja) | 2012-03-14 |
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ID=34968416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2007512027A Expired - Fee Related JP4896009B2 (ja) | 2004-05-10 | 2005-05-06 | オキソ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) | US7476763B2 (https=) |
| EP (1) | EP1751088B1 (https=) |
| JP (1) | JP4896009B2 (https=) |
| CA (1) | CA2566210C (https=) |
| DE (1) | DE102004023501A1 (https=) |
| WO (1) | WO2005110970A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2008110351A2 (en) * | 2007-03-15 | 2008-09-18 | Dompe' Pha.R.Ma S.P.A. | Use of (r) and (s)-2-aryl-propionic acid derivatives as antiseptic agents |
| 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 |
|---|---|---|---|---|
| US5304479A (en) | 1991-12-06 | 1994-04-19 | Diagnostic Reagents, Inc. | Phencyclidine compounds and assays for its determination |
| 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 |
| GB0012240D0 (en) | 2000-05-19 | 2000-07-12 | Merck Sharp & Dohme | Therapeutic agents |
| 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 |
| US6571525B2 (en) | 2001-08-01 | 2003-06-03 | J. David Coleman | Construction block |
| EP1458704A1 (en) * | 2001-12-21 | 2004-09-22 | H. Lundbeck A/S | Aminoindane derivatives as serotonin and norepinephrine uptake inhibitors |
| US6818772B2 (en) * | 2002-02-22 | 2004-11-16 | Abbott Laboratories | Antagonists of melanin concentrating hormone effects on the melanin concentrating hormone receptor |
| 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 |
| DE102004023522A1 (de) * | 2004-05-10 | 2005-12-01 | Grünenthal GmbH | Substituierte Cyclohexyl-1,4-diamin-Derivate |
-
2004
- 2004-05-10 DE DE102004023501A patent/DE102004023501A1/de not_active Withdrawn
-
2005
- 2005-05-06 WO PCT/EP2005/004907 patent/WO2005110970A1/de not_active Ceased
- 2005-05-06 EP EP05738450.5A patent/EP1751088B1/de not_active Expired - Lifetime
- 2005-05-06 CA CA2566210A patent/CA2566210C/en not_active Expired - Fee Related
- 2005-05-06 JP JP2007512027A patent/JP4896009B2/ja not_active Expired - Fee Related
-
2006
- 2006-11-09 US US11/594,952 patent/US7476763B2/en not_active Expired - Fee Related
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