JP2007536320A5 - - Google Patents
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- Publication number
- JP2007536320A5 JP2007536320A5 JP2007512030A JP2007512030A JP2007536320A5 JP 2007536320 A5 JP2007536320 A5 JP 2007536320A5 JP 2007512030 A JP2007512030 A JP 2007512030A JP 2007512030 A JP2007512030 A JP 2007512030A JP 2007536320 A5 JP2007536320 A5 JP 2007536320A5
- Authority
- JP
- Japan
- Prior art keywords
- benzyl
- cyclohexylcarbamoyl
- methyl
- dimethylamino
- carbamic 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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- 208000002193 Pain Diseases 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 208000000094 Chronic Pain Diseases 0.000 claims description 5
- 229940005483 opioid analgesics Drugs 0.000 claims description 4
- 230000001154 acute effect Effects 0.000 claims description 3
- 208000005298 acute pain Diseases 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 208000004296 neuralgia Diseases 0.000 claims description 3
- 230000002981 neuropathic effect Effects 0.000 claims description 3
- 208000021722 neuropathic pain Diseases 0.000 claims description 3
- 206010012335 Dependence Diseases 0.000 claims description 2
- -1 methyl fluorenyl Chemical group 0.000 claims 17
- 239000002253 acid Substances 0.000 claims 7
- 229920006395 saturated elastomer Polymers 0.000 claims 5
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 229940080818 propionamide Drugs 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 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 3
- 229940079593 drug Drugs 0.000 claims 3
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 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 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000016285 Movement disease Diseases 0.000 claims 2
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 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
- GXAFOJZPUKRYSY-UHFFFAOYSA-N 2-acetamido-n-[4-[(2-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]hexanamide Chemical compound C1CC(NC(=O)C(NC(C)=O)CCCC)CCC1(N(C)C)CC1=CC=CC=C1Cl GXAFOJZPUKRYSY-UHFFFAOYSA-N 0.000 claims 1
- YOERDTSSMPNRQF-UHFFFAOYSA-N 2-acetamido-n-[4-[(2-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]pent-4-enamide Chemical compound C=1C=CC=C(Cl)C=1CC1(N(C)C)CCC(NC(=O)C(CC=C)NC(C)=O)CC1 YOERDTSSMPNRQF-UHFFFAOYSA-N 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
- 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
- 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
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- PGJXRVZLLHNGNQ-UHFFFAOYSA-N 4-chloro-n-[2-[4-[1-[[4-(dimethylamino)-4-[(2-methylphenyl)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=C1C PGJXRVZLLHNGNQ-UHFFFAOYSA-N 0.000 claims 1
- NNGOTRFRZOVEPS-UHFFFAOYSA-N 4-chloro-n-[2-[4-[1-[[4-[(2-chlorophenyl)methyl]-4-(dimethylamino)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=C1Cl NNGOTRFRZOVEPS-UHFFFAOYSA-N 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
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical class OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 206010006895 Cachexia Diseases 0.000 claims 1
- 208000009132 Catalepsy Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 206010011878 Deafness Diseases 0.000 claims 1
- 206010012735 Diarrhoea Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 208000001953 Hypotension Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000003251 Pruritus Diseases 0.000 claims 1
- 206010039966 Senile dementia Diseases 0.000 claims 1
- 201000001880 Sexual dysfunction Diseases 0.000 claims 1
- 208000009205 Tinnitus Diseases 0.000 claims 1
- 206010046543 Urinary incontinence Diseases 0.000 claims 1
- 206010047853 Waxy flexibility Diseases 0.000 claims 1
- WAGCNQBAFBJYDW-UHFFFAOYSA-N [1-[[4-(dimethylamino)-4-[(4-fluorophenyl)methyl]cyclohexyl]amino]-3-methyl-1-oxobutan-2-yl]carbamic acid Chemical compound C1CC(NC(=O)C(NC(O)=O)C(C)C)CCC1(N(C)C)CC1=CC=C(F)C=C1 WAGCNQBAFBJYDW-UHFFFAOYSA-N 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000003444 anaesthetic effect Effects 0.000 claims 1
- 230000001773 anti-convulsant effect Effects 0.000 claims 1
- 239000001961 anticonvulsive agent Substances 0.000 claims 1
- 229960003965 antiepileptics Drugs 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 239000002249 anxiolytic agent Substances 0.000 claims 1
- 230000000949 anxiolytic effect Effects 0.000 claims 1
- 230000004596 appetite loss Effects 0.000 claims 1
- RHLMGMGSEZHGQU-UHFFFAOYSA-N benzyl n-[1-[(4-benzyl-4-piperidin-1-ylcyclohexyl)amino]-1-oxopropan-2-yl]carbamate Chemical compound C1CC(CC=2C=CC=CC=2)(N2CCCCC2)CCC1NC(=O)C(C)NC(=O)OCC1=CC=CC=C1 RHLMGMGSEZHGQU-UHFFFAOYSA-N 0.000 claims 1
- YJQBTKRCIVLNCI-UHFFFAOYSA-N benzyl n-[1-[(4-morpholin-4-yl-4-phenylcyclohexyl)amino]-1-oxopropan-2-yl]carbamate Chemical compound C1CC(C=2C=CC=CC=2)(N2CCOCC2)CCC1NC(=O)C(C)NC(=O)OCC1=CC=CC=C1 YJQBTKRCIVLNCI-UHFFFAOYSA-N 0.000 claims 1
- IQBLTBIXBZDDHI-UHFFFAOYSA-N benzyl n-[1-[[4-(dimethylamino)-4-(2-phenylethyl)cyclohexyl]amino]-1-oxopropan-2-yl]carbamate Chemical compound C1CC(CCC=2C=CC=CC=2)(N(C)C)CCC1NC(=O)C(C)NC(=O)OCC1=CC=CC=C1 IQBLTBIXBZDDHI-UHFFFAOYSA-N 0.000 claims 1
- UQCSYPWNIQUJSP-UHFFFAOYSA-N benzyl n-[1-[[4-(dimethylamino)-4-[(2-methylphenyl)methyl]cyclohexyl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate Chemical compound C1CC(NC(=O)C(CC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC=C1C UQCSYPWNIQUJSP-UHFFFAOYSA-N 0.000 claims 1
- JHBHFEAYSWAFPO-UHFFFAOYSA-N benzyl n-[1-[[4-(dimethylamino)-4-[(2-methylphenyl)methyl]cyclohexyl]amino]-1-oxopropan-2-yl]carbamate Chemical compound C1CC(CC=2C(=CC=CC=2)C)(N(C)C)CCC1NC(=O)C(C)NC(=O)OCC1=CC=CC=C1 JHBHFEAYSWAFPO-UHFFFAOYSA-N 0.000 claims 1
- XAGDQZRWILQDGE-UHFFFAOYSA-N benzyl n-[1-[[4-(dimethylamino)-4-[(3-fluorophenyl)methyl]cyclohexyl]amino]-1-oxopropan-2-yl]carbamate Chemical compound C1CC(CC=2C=C(F)C=CC=2)(N(C)C)CCC1NC(=O)C(C)NC(=O)OCC1=CC=CC=C1 XAGDQZRWILQDGE-UHFFFAOYSA-N 0.000 claims 1
- ZPVNQGNDDLPPOX-UHFFFAOYSA-N benzyl n-[1-[[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]amino]-1-oxopropan-2-yl]carbamate Chemical compound C1CC(CC=2C=C(C)C=CC=2)(N(C)C)CCC1NC(=O)C(C)NC(=O)OCC1=CC=CC=C1 ZPVNQGNDDLPPOX-UHFFFAOYSA-N 0.000 claims 1
- SOKDHRWLTFHRQU-UHFFFAOYSA-N benzyl n-[1-[[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]amino]-1-oxopropan-2-yl]carbamate Chemical compound C1CC(CC=2C=CC(C)=CC=2)(N(C)C)CCC1NC(=O)C(C)NC(=O)OCC1=CC=CC=C1 SOKDHRWLTFHRQU-UHFFFAOYSA-N 0.000 claims 1
- KLZJFOHPOGCJEL-UHFFFAOYSA-N benzyl n-[1-[[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]amino]-1-oxopropan-2-yl]carbamate Chemical compound C1CC(C=2SC=CC=2)(N(C)C)CCC1NC(=O)C(C)NC(=O)OCC1=CC=CC=C1 KLZJFOHPOGCJEL-UHFFFAOYSA-N 0.000 claims 1
- YVOBYGNRKKHKKC-UHFFFAOYSA-N benzyl n-[1-[[4-[(2-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]amino]-1-oxopropan-2-yl]carbamate Chemical compound C1CC(CC=2C(=CC=CC=2)Cl)(N(C)C)CCC1NC(=O)C(C)NC(=O)OCC1=CC=CC=C1 YVOBYGNRKKHKKC-UHFFFAOYSA-N 0.000 claims 1
- SBABKILZPSUBMR-UHFFFAOYSA-N benzyl n-[1-[[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]amino]-1-oxopropan-2-yl]carbamate Chemical compound C1CC(CC=2C=C(Cl)C=CC=2)(N(C)C)CCC1NC(=O)C(C)NC(=O)OCC1=CC=CC=C1 SBABKILZPSUBMR-UHFFFAOYSA-N 0.000 claims 1
- DVTGPHZYEUKBPP-UHFFFAOYSA-N benzyl n-[1-[[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]amino]-1-oxopropan-2-yl]carbamate Chemical compound C1CC(CC=2C=CC(Cl)=CC=2)(N(C)C)CCC1NC(=O)C(C)NC(=O)OCC1=CC=CC=C1 DVTGPHZYEUKBPP-UHFFFAOYSA-N 0.000 claims 1
- RRMMJTOGXCFXRY-UHFFFAOYSA-N benzyl n-[1-[[4-benzyl-4-(dimethylamino)cyclohexyl]amino]-1-oxopropan-2-yl]carbamate Chemical compound C1CC(CC=2C=CC=CC=2)(N(C)C)CCC1NC(=O)C(C)NC(=O)OCC1=CC=CC=C1 RRMMJTOGXCFXRY-UHFFFAOYSA-N 0.000 claims 1
- CEPYKCUBALYUPN-UHFFFAOYSA-N benzyl n-[2-[[1-[(4-benzyl-4-piperidin-1-ylcyclohexyl)amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]carbamate Chemical compound C1CC(CC=2C=CC=CC=2)(N2CCCCC2)CCC1NC(=O)C(CC(C)C)NC(=O)CNC(=O)OCC1=CC=CC=C1 CEPYKCUBALYUPN-UHFFFAOYSA-N 0.000 claims 1
- JIJOYXAOCVMTFG-UHFFFAOYSA-N benzyl n-[2-[[1-[[4-(dimethylamino)-4-(2-phenylethyl)cyclohexyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]carbamate Chemical compound C1CC(CCC=2C=CC=CC=2)(N(C)C)CCC1NC(=O)C(CC(C)C)NC(=O)CNC(=O)OCC1=CC=CC=C1 JIJOYXAOCVMTFG-UHFFFAOYSA-N 0.000 claims 1
- DTWZTQIQHCHSRU-UHFFFAOYSA-N benzyl n-[2-[[1-[[4-(dimethylamino)-4-phenylcyclohexyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]carbamate Chemical compound C1CC(C=2C=CC=CC=2)(N(C)C)CCC1NC(=O)C(CC(C)C)NC(=O)CNC(=O)OCC1=CC=CC=C1 DTWZTQIQHCHSRU-UHFFFAOYSA-N 0.000 claims 1
- HTTVOKODCLHIAD-UHFFFAOYSA-N benzyl n-[2-[[1-[[4-(dimethylamino)-4-thiophen-2-ylcyclohexyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]carbamate Chemical compound C1CC(C=2SC=CC=2)(N(C)C)CCC1NC(=O)C(CC(C)C)NC(=O)CNC(=O)OCC1=CC=CC=C1 HTTVOKODCLHIAD-UHFFFAOYSA-N 0.000 claims 1
- WLSYRHDGKBLVJI-UHFFFAOYSA-N benzyl n-[2-[[1-[[4-benzyl-4-(dimethylamino)cyclohexyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]carbamate Chemical compound C1CC(CC=2C=CC=CC=2)(N(C)C)CCC1NC(=O)C(CC(C)C)NC(=O)CNC(=O)OCC1=CC=CC=C1 WLSYRHDGKBLVJI-UHFFFAOYSA-N 0.000 claims 1
- WDYWFXRPNCGJHZ-UHFFFAOYSA-N benzyl n-[2-[[4-(azepan-1-yl)-4-benzylcyclohexyl]amino]-2-oxo-1-phenylethyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC(C=1C=CC=CC=1)C(=O)NC(CC1)CCC1(N1CCCCCC1)CC1=CC=CC=C1 WDYWFXRPNCGJHZ-UHFFFAOYSA-N 0.000 claims 1
- FZAPGZNDUSBVRX-UHFFFAOYSA-N benzyl n-[2-[[4-(dimethylamino)-4-[(2-methylphenyl)methyl]cyclohexyl]amino]-2-oxo-1-phenylethyl]carbamate Chemical compound C1CC(NC(=O)C(NC(=O)OCC=2C=CC=CC=2)C=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC=C1C FZAPGZNDUSBVRX-UHFFFAOYSA-N 0.000 claims 1
- MSGBKILZCSUFEE-UHFFFAOYSA-N benzyl n-[2-[[4-[(2-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]amino]-2-oxo-1-phenylethyl]carbamate Chemical compound C1CC(NC(=O)C(NC(=O)OCC=2C=CC=CC=2)C=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC=C1Cl MSGBKILZCSUFEE-UHFFFAOYSA-N 0.000 claims 1
- RIIJBFVHRSMAFI-UHFFFAOYSA-N benzyl n-[2-[[4-methyl-1-[(4-morpholin-4-yl-4-phenylcyclohexyl)amino]-1-oxopentan-2-yl]amino]-2-oxoethyl]carbamate Chemical compound C1CC(C=2C=CC=CC=2)(N2CCOCC2)CCC1NC(=O)C(CC(C)C)NC(=O)CNC(=O)OCC1=CC=CC=C1 RIIJBFVHRSMAFI-UHFFFAOYSA-N 0.000 claims 1
- IECVVJLRZQEOEC-UHFFFAOYSA-N benzyl n-[2-[[4-methyl-1-oxo-1-[(4-phenyl-4-piperidin-1-ylcyclohexyl)amino]pentan-2-yl]amino]-2-oxoethyl]carbamate Chemical compound C1CC(C=2C=CC=CC=2)(N2CCCCC2)CCC1NC(=O)C(CC(C)C)NC(=O)CNC(=O)OCC1=CC=CC=C1 IECVVJLRZQEOEC-UHFFFAOYSA-N 0.000 claims 1
- XKWGEHKWAIVPDH-UHFFFAOYSA-N benzyl n-[6-[[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]amino]-6-oxohexyl]carbamate Chemical compound C1CC(NC(=O)CCCCCNC(=O)OCC=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=C(C)C=C1 XKWGEHKWAIVPDH-UHFFFAOYSA-N 0.000 claims 1
- HKTJGPJYOFBXOW-UHFFFAOYSA-N benzyl n-[6-[[4-benzyl-4-(dimethylamino)cyclohexyl]amino]-6-oxohexyl]carbamate Chemical compound C1CC(NC(=O)CCCCCNC(=O)OCC=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC=C1 HKTJGPJYOFBXOW-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical class NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 235000014632 disordered eating Nutrition 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 239000003193 general anesthetic agent Substances 0.000 claims 1
- 230000010370 hearing loss Effects 0.000 claims 1
- 231100000888 hearing loss Toxicity 0.000 claims 1
- 208000016354 hearing loss disease Diseases 0.000 claims 1
- 230000036543 hypotension Effects 0.000 claims 1
- 208000019017 loss of appetite Diseases 0.000 claims 1
- 235000021266 loss of appetite Nutrition 0.000 claims 1
- 206010027175 memory impairment Diseases 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 230000037023 motor activity Effects 0.000 claims 1
- 239000003158 myorelaxant agent Substances 0.000 claims 1
- HRXQHLQODOMOIT-UHFFFAOYSA-N n-(4-benzyl-4-pyrrolidin-1-ylcyclohexyl)-2-(2,2,2-trifluoroacetyl)-3,4-dihydro-1h-isoquinoline-7-sulfonamide Chemical compound C1=C2CN(C(=O)C(F)(F)F)CCC2=CC=C1S(=O)(=O)NC(CC1)CCC1(N1CCCC1)CC1=CC=CC=C1 HRXQHLQODOMOIT-UHFFFAOYSA-N 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 230000003957 neurotransmitter release Effects 0.000 claims 1
- 230000001777 nootropic effect Effects 0.000 claims 1
- 239000000014 opioid analgesic Substances 0.000 claims 1
- 229940052318 opioid anesthetics Drugs 0.000 claims 1
- 231100000572 poisoning Toxicity 0.000 claims 1
- 230000000607 poisoning effect Effects 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 231100000872 sexual dysfunction Toxicity 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- CZJWYXSDDFJKHM-UHFFFAOYSA-N tert-butyl N-[1-[(4-morpholin-4-yl-4-phenylcyclohexyl)amino]-1-oxo-3-phenylpropan-2-yl]carbamate Chemical compound C1CC(C=2C=CC=CC=2)(N2CCOCC2)CCC1NC(=O)C(NC(=O)OC(C)(C)C)CC1=CC=CC=C1 CZJWYXSDDFJKHM-UHFFFAOYSA-N 0.000 claims 1
- QQBARZSUHWAZKQ-UHFFFAOYSA-N tert-butyl N-[1-[[4-(azepan-1-yl)-4-benzylcyclohexyl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate Chemical compound C1CC(CC=2C=CC=CC=2)(N2CCCCCC2)CCC1NC(=O)C(NC(=O)OC(C)(C)C)CC1=CC=CC=C1 QQBARZSUHWAZKQ-UHFFFAOYSA-N 0.000 claims 1
- VXFQXFGJXPVWEX-UHFFFAOYSA-N tert-butyl N-[1-[[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]amino]-3-hydroxy-1-oxopropan-2-yl]carbamate Chemical compound C=1C=C(Cl)C=CC=1CC1(N(C)C)CCC(NC(=O)C(CO)NC(=O)OC(C)(C)C)CC1 VXFQXFGJXPVWEX-UHFFFAOYSA-N 0.000 claims 1
- WFEYHDFUNZEUKX-UHFFFAOYSA-N tert-butyl N-[1-[[4-benzyl-4-(dimethylamino)cyclohexyl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate Chemical compound C1CC(NC(=O)C(CC=2C=CC=CC=2)NC(=O)OC(C)(C)C)CCC1(N(C)C)CC1=CC=CC=C1 WFEYHDFUNZEUKX-UHFFFAOYSA-N 0.000 claims 1
- CTSOWTCMGKTDLV-UHFFFAOYSA-N tert-butyl N-[5-amino-1-[(4-benzyl-4-piperidin-1-ylcyclohexyl)amino]-1,5-dioxopentan-2-yl]carbamate Chemical compound C1CC(NC(=O)C(CCC(N)=O)NC(=O)OC(C)(C)C)CCC1(N1CCCCC1)CC1=CC=CC=C1 CTSOWTCMGKTDLV-UHFFFAOYSA-N 0.000 claims 1
- BAKJESYGSKCXOE-UHFFFAOYSA-N tert-butyl n-[1-[(4-benzyl-4-piperidin-1-ylcyclohexyl)amino]-3-hydroxy-1-oxopropan-2-yl]carbamate Chemical compound C1CC(NC(=O)C(CO)NC(=O)OC(C)(C)C)CCC1(N1CCCCC1)CC1=CC=CC=C1 BAKJESYGSKCXOE-UHFFFAOYSA-N 0.000 claims 1
- IZXBAAUUJZAGLD-UHFFFAOYSA-N tert-butyl n-[1-[[4-(dimethylamino)-4-[(2-fluorophenyl)methyl]cyclohexyl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate Chemical compound C1CC(NC(=O)C(CC=2C=CC=CC=2)NC(=O)OC(C)(C)C)CCC1(N(C)C)CC1=CC=CC=C1F IZXBAAUUJZAGLD-UHFFFAOYSA-N 0.000 claims 1
- QUQHUACLJSKDLF-UHFFFAOYSA-N tert-butyl n-[1-[[4-(dimethylamino)-4-[(2-methylphenyl)methyl]cyclohexyl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate Chemical compound C1CC(NC(=O)C(CC=2C=CC=CC=2)NC(=O)OC(C)(C)C)CCC1(N(C)C)CC1=CC=CC=C1C QUQHUACLJSKDLF-UHFFFAOYSA-N 0.000 claims 1
- ZQUUSEGUAZPYDI-UHFFFAOYSA-N tert-butyl n-[1-[[4-(dimethylamino)-4-[(3-fluorophenyl)methyl]cyclohexyl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate Chemical compound C1CC(NC(=O)C(CC=2C=CC=CC=2)NC(=O)OC(C)(C)C)CCC1(N(C)C)CC1=CC=CC(F)=C1 ZQUUSEGUAZPYDI-UHFFFAOYSA-N 0.000 claims 1
- GRIXIHHABVGKLK-UHFFFAOYSA-N tert-butyl n-[1-[[4-(dimethylamino)-4-[(3-methylphenyl)methyl]cyclohexyl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate Chemical compound C1CC(NC(=O)C(CC=2C=CC=CC=2)NC(=O)OC(C)(C)C)CCC1(N(C)C)CC1=CC=CC(C)=C1 GRIXIHHABVGKLK-UHFFFAOYSA-N 0.000 claims 1
- AZLQNKXNMPBZEZ-UHFFFAOYSA-N tert-butyl n-[1-[[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate Chemical compound C1CC(NC(=O)C(CC=2C=CC=CC=2)NC(=O)OC(C)(C)C)CCC1(N(C)C)CC1=CC=C(C)C=C1 AZLQNKXNMPBZEZ-UHFFFAOYSA-N 0.000 claims 1
- FVUYELGXRLLCHH-UHFFFAOYSA-N tert-butyl n-[1-[[4-(dimethylamino)-4-[(4-methylphenyl)methyl]cyclohexyl]amino]-3-hydroxy-1-oxopropan-2-yl]carbamate Chemical compound C=1C=C(C)C=CC=1CC1(N(C)C)CCC(NC(=O)C(CO)NC(=O)OC(C)(C)C)CC1 FVUYELGXRLLCHH-UHFFFAOYSA-N 0.000 claims 1
- PSLOUZFYOCXUGA-UHFFFAOYSA-N tert-butyl n-[1-[[4-[(3-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]amino]-3-hydroxy-1-oxopropan-2-yl]carbamate Chemical compound C=1C=CC(Cl)=CC=1CC1(N(C)C)CCC(NC(=O)C(CO)NC(=O)OC(C)(C)C)CC1 PSLOUZFYOCXUGA-UHFFFAOYSA-N 0.000 claims 1
- MCHDOZKCHJZAMP-UHFFFAOYSA-N tert-butyl n-[1-[[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate Chemical compound C1CC(NC(=O)C(CC=2C=CC=CC=2)NC(=O)OC(C)(C)C)CCC1(N(C)C)CC1=CC=C(Cl)C=C1 MCHDOZKCHJZAMP-UHFFFAOYSA-N 0.000 claims 1
- SZMQXZLHRZXXIU-UHFFFAOYSA-N tert-butyl n-[1-oxo-3-phenyl-1-[(4-phenyl-4-piperidin-1-ylcyclohexyl)amino]propan-2-yl]carbamate Chemical compound C1CC(C=2C=CC=CC=2)(N2CCCCC2)CCC1NC(=O)C(NC(=O)OC(C)(C)C)CC1=CC=CC=C1 SZMQXZLHRZXXIU-UHFFFAOYSA-N 0.000 claims 1
- USNCGWXGBYMNKO-UHFFFAOYSA-N tert-butyl n-[3-[[4-(dimethylamino)-4-(2-phenylethyl)cyclohexyl]amino]-3-oxopropyl]carbamate Chemical compound C=1C=CC=CC=1CCC1(N(C)C)CCC(NC(=O)CCNC(=O)OC(C)(C)C)CC1 USNCGWXGBYMNKO-UHFFFAOYSA-N 0.000 claims 1
- MLMNPBDHILNTFL-UHFFFAOYSA-N tert-butyl n-[3-[[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexyl]amino]-3-oxopropyl]carbamate Chemical compound C=1C=CC(F)=CC=1C1(N(C)C)CCC(NC(=O)CCNC(=O)OC(C)(C)C)CC1 MLMNPBDHILNTFL-UHFFFAOYSA-N 0.000 claims 1
- LJHNOCPYCYQSTR-UHFFFAOYSA-N tert-butyl n-[3-[[4-(dimethylamino)-4-[(3-fluorophenyl)methyl]cyclohexyl]amino]-3-oxopropyl]carbamate Chemical compound C=1C=CC(F)=CC=1CC1(N(C)C)CCC(NC(=O)CCNC(=O)OC(C)(C)C)CC1 LJHNOCPYCYQSTR-UHFFFAOYSA-N 0.000 claims 1
- CVMHOPKFEKYNEM-UHFFFAOYSA-N tert-butyl n-[3-[[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]amino]-3-oxopropyl]carbamate Chemical compound C=1C=C(Cl)C=CC=1CC1(N(C)C)CCC(NC(=O)CCNC(=O)OC(C)(C)C)CC1 CVMHOPKFEKYNEM-UHFFFAOYSA-N 0.000 claims 1
- FCVWQFWSAFTEJN-UHFFFAOYSA-N tert-butyl n-[3-hydroxy-1-[(4-morpholin-4-yl-4-phenylcyclohexyl)amino]-1-oxopropan-2-yl]carbamate Chemical compound C1CC(NC(=O)C(CO)NC(=O)OC(C)(C)C)CCC1(C=1C=CC=CC=1)N1CCOCC1 FCVWQFWSAFTEJN-UHFFFAOYSA-N 0.000 claims 1
- QHPPFIWOLPJOEL-UHFFFAOYSA-N tert-butyl n-[3-hydroxy-1-oxo-1-[(4-phenyl-4-piperidin-1-ylcyclohexyl)amino]propan-2-yl]carbamate Chemical compound C1CC(NC(=O)C(CO)NC(=O)OC(C)(C)C)CCC1(C=1C=CC=CC=1)N1CCCCC1 QHPPFIWOLPJOEL-UHFFFAOYSA-N 0.000 claims 1
- AWJKJSPKEQNQCF-UHFFFAOYSA-N tert-butyl n-[5-amino-1-[[4-[(4-chlorophenyl)methyl]-4-(dimethylamino)cyclohexyl]amino]-1,5-dioxopentan-2-yl]carbamate Chemical compound C=1C=C(Cl)C=CC=1CC1(N(C)C)CCC(NC(=O)C(CCC(N)=O)NC(=O)OC(C)(C)C)CC1 AWJKJSPKEQNQCF-UHFFFAOYSA-N 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 231100000886 tinnitus Toxicity 0.000 claims 1
- 108090000137 Opioid Receptors Proteins 0.000 description 3
- 102000003840 Opioid Receptors Human genes 0.000 description 3
- 230000001684 chronic effect Effects 0.000 description 3
- LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical class OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 description 3
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 108010020615 nociceptin receptor Proteins 0.000 description 2
- 206010010774 Constipation Diseases 0.000 description 1
- 101001122499 Homo sapiens Nociceptin receptor Proteins 0.000 description 1
- 102100028646 Nociceptin receptor Human genes 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 102000051367 mu Opioid Receptors Human genes 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000020341 sensory perception of pain Effects 0.000 description 1
- 108020001612 μ-opioid receptors Proteins 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004023508.2 | 2004-05-10 | ||
| DE102004023508A DE102004023508A1 (de) | 2004-05-10 | 2004-05-10 | Säurederivate substituierter Cyclohexyl-1,4-diamine |
| PCT/EP2005/004910 WO2005110973A1 (de) | 2004-05-10 | 2005-05-06 | Saürederivate substituierter cyclohexyl-1,4-diamine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007536320A JP2007536320A (ja) | 2007-12-13 |
| JP2007536320A5 true JP2007536320A5 (https=) | 2011-05-26 |
| JP5084498B2 JP5084498B2 (ja) | 2012-11-28 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2007512030A Expired - Fee Related JP5084498B2 (ja) | 2004-05-10 | 2005-05-06 | シクロヘキシル−１，４−ジアミンの酸誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7439394B2 (https=) |
| EP (1) | EP1751090B1 (https=) |
| JP (1) | JP5084498B2 (https=) |
| CA (1) | CA2566215C (https=) |
| DE (1) | DE102004023508A1 (https=) |
| WO (1) | WO2005110973A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200940523A (en) * | 2008-03-17 | 2009-10-01 | Gruenenthal Gmbh | Substituted sulfonamide derivatives |
| 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 |
| HK1199259A1 (en) | 2011-08-15 | 2015-06-26 | Intermune, Inc. | Lysophosphatidic acid receptor antagonists |
| TW202547460A (zh) * | 2024-04-04 | 2025-12-16 | 日商橘生藥品工業股份有限公司 | 取代磺醯胺化合物 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EP1458704A1 (en) * | 2001-12-21 | 2004-09-22 | H. Lundbeck A/S | Aminoindane derivatives as serotonin and norepinephrine uptake inhibitors |
| DE10252650A1 (de) * | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Cyclohexyl-Harnstoff-Derivate |
-
2004
- 2004-05-10 DE DE102004023508A patent/DE102004023508A1/de not_active Withdrawn
-
2005
- 2005-05-06 CA CA2566215A patent/CA2566215C/en not_active Expired - Fee Related
- 2005-05-06 JP JP2007512030A patent/JP5084498B2/ja not_active Expired - Fee Related
- 2005-05-06 WO PCT/EP2005/004910 patent/WO2005110973A1/de not_active Ceased
- 2005-05-06 EP EP05741145.6A patent/EP1751090B1/de not_active Expired - Lifetime
-
2006
- 2006-11-09 US US11/594,944 patent/US7439394B2/en not_active Expired - Fee Related
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