ZA200303224B - Substituted C-cyclohexylmethylamine derivatives. - Google Patents
Substituted C-cyclohexylmethylamine derivatives. Download PDFInfo
- Publication number
- ZA200303224B ZA200303224B ZA200303224A ZA200303224A ZA200303224B ZA 200303224 B ZA200303224 B ZA 200303224B ZA 200303224 A ZA200303224 A ZA 200303224A ZA 200303224 A ZA200303224 A ZA 200303224A ZA 200303224 B ZA200303224 B ZA 200303224B
- Authority
- ZA
- South Africa
- Prior art keywords
- dimethylaminomethyl
- cyclohexanol
- singly
- phenyl
- methoxy
- Prior art date
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- AVKNGPAMCBSNSO-UHFFFAOYSA-N cyclohexylmethanamine Chemical class NCC1CCCCC1 AVKNGPAMCBSNSO-UHFFFAOYSA-N 0.000 title claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 253
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 232
- 229920006395 saturated elastomer Polymers 0.000 claims description 214
- 125000001072 heteroaryl group Chemical group 0.000 claims description 188
- 125000003118 aryl group Chemical group 0.000 claims description 148
- 125000002947 alkylene group Chemical group 0.000 claims description 102
- -1 1-(4-tert-butyl-phenyl)-2-(dimethylamino-phenyl-methyl)-4-phenyl- cyclohexanol 2-(dimethylamino-phenyl-methyl)-4-phenyl-1-m-tolyl-cyclohexanol Chemical compound 0.000 claims description 48
- 125000003107 substituted aryl group Chemical group 0.000 claims description 47
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 34
- 150000003254 radicals Chemical group 0.000 claims description 32
- 229910052731 fluorine Inorganic materials 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 229910052801 chlorine Inorganic materials 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 229910052794 bromium Inorganic materials 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- 229910052740 iodine Inorganic materials 0.000 claims description 16
- 208000002193 Pain Diseases 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 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 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 230000036407 pain Effects 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 208000000094 Chronic Pain Diseases 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 150000004677 hydrates Chemical class 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 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
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 2
- SNCIVROMQYNLPF-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-4-[(4-fluorophenyl)methoxy]-1-(4-methylphenyl)cyclohexan-1-ol Chemical compound CN(C)CC1CC(OCC=2C=CC(F)=CC=2)CCC1(O)C1=CC=C(C)C=C1 SNCIVROMQYNLPF-UHFFFAOYSA-N 0.000 claims 3
- KZIUPGPAPINWBA-UHFFFAOYSA-N [3-[(dimethylamino)methyl]-4-hydroxy-4-(3-methoxyphenyl)cyclohexyl] butanoate Chemical compound CN(C)CC1CC(OC(=O)CCC)CCC1(O)C1=CC=CC(OC)=C1 KZIUPGPAPINWBA-UHFFFAOYSA-N 0.000 claims 3
- KLJIEQDARIJWOL-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[(dimethylamino)methyl]-4-[(4-fluorophenyl)methyl]cyclohexan-1-ol Chemical compound C1CC(C=2C=CC(Cl)=CC=2)(O)C(CN(C)C)CC1CC1=CC=C(F)C=C1 KLJIEQDARIJWOL-UHFFFAOYSA-N 0.000 claims 2
- TUHWOZCOWNNAAM-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]-2-[(dimethylamino)methyl]-4-phenylmethoxycyclohexan-1-ol Chemical compound CN(C)CC1CC(OCC=2C=CC=CC=2)CCC1(O)C1=CC=C(Cl)C(C(F)(F)F)=C1 TUHWOZCOWNNAAM-UHFFFAOYSA-N 0.000 claims 2
- VTJXBZGMVJOVDU-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1,4-bis(3-methoxyphenyl)cyclohexane-1,4-diol Chemical compound COC1=CC=CC(C2(O)CC(CN(C)C)C(O)(CC2)C=2C=C(OC)C=CC=2)=C1 VTJXBZGMVJOVDU-UHFFFAOYSA-N 0.000 claims 2
- GCFPMEXREQEHDG-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-(3-fluorophenyl)-4-phenylmethoxycyclohexan-1-ol Chemical compound CN(C)CC1CC(OCC=2C=CC=CC=2)CCC1(O)C1=CC=CC(F)=C1 GCFPMEXREQEHDG-UHFFFAOYSA-N 0.000 claims 2
- BOZJRIIPNZUDPZ-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)-4-(naphthalen-2-ylmethoxy)cyclohexan-1-ol Chemical compound COC1=CC=CC(C2(O)C(CC(CC2)OCC=2C=C3C=CC=CC3=CC=2)CN(C)C)=C1 BOZJRIIPNZUDPZ-UHFFFAOYSA-N 0.000 claims 2
- QKHHUGSHNAAQSS-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-(4-fluoro-3-methylphenyl)-4-[(4-fluorophenyl)methoxy]cyclohexan-1-ol Chemical compound CN(C)CC1CC(OCC=2C=CC(F)=CC=2)CCC1(O)C1=CC=C(F)C(C)=C1 QKHHUGSHNAAQSS-UHFFFAOYSA-N 0.000 claims 2
- ZBWWRMNTHUOBPE-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-(4-fluoro-3-methylphenyl)-4-phenylmethoxycyclohexan-1-ol Chemical compound CN(C)CC1CC(OCC=2C=CC=CC=2)CCC1(O)C1=CC=C(F)C(C)=C1 ZBWWRMNTHUOBPE-UHFFFAOYSA-N 0.000 claims 2
- YUYWULHUTZAVDX-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-[(2,5-dimethylphenyl)methyl]-4-[(4-fluorophenyl)methoxy]cyclohexan-1-ol Chemical compound CN(C)CC1CC(OCC=2C=CC(F)=CC=2)CCC1(O)CC1=CC(C)=CC=C1C YUYWULHUTZAVDX-UHFFFAOYSA-N 0.000 claims 2
- MZHRQOWXGGFCSC-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-[(3-fluorophenyl)methyl]-4-phenylmethoxycyclohexan-1-ol Chemical compound CN(C)CC1CC(OCC=2C=CC=CC=2)CCC1(O)CC1=CC=CC(F)=C1 MZHRQOWXGGFCSC-UHFFFAOYSA-N 0.000 claims 2
- FJWIFVGEMKGGST-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-4-[(3-methoxyphenyl)methyl]-1-(4-methylphenyl)cyclohexan-1-ol Chemical compound COC1=CC=CC(CC2CC(CN(C)C)C(O)(CC2)C=2C=CC(C)=CC=2)=C1 FJWIFVGEMKGGST-UHFFFAOYSA-N 0.000 claims 2
- BAGZCRUKSTXAOM-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-4-[(4-fluorophenyl)methoxy]-1-(2-methoxyphenyl)cyclohexan-1-ol Chemical compound COC1=CC=CC=C1C1(O)C(CN(C)C)CC(OCC=2C=CC(F)=CC=2)CC1 BAGZCRUKSTXAOM-UHFFFAOYSA-N 0.000 claims 2
- DHPDBLQGKOFXOK-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-4-[(4-fluorophenyl)methoxy]-1-[(3-fluorophenyl)methyl]cyclohexan-1-ol Chemical compound CN(C)CC1CC(OCC=2C=CC(F)=CC=2)CCC1(O)CC1=CC=CC(F)=C1 DHPDBLQGKOFXOK-UHFFFAOYSA-N 0.000 claims 2
- XJOCFTKUCRHFAG-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-4-phenylmethoxy-1-(3-phenylpropyl)cyclohexan-1-ol Chemical compound CN(C)CC1CC(OCC=2C=CC=CC=2)CCC1(O)CCCC1=CC=CC=C1 XJOCFTKUCRHFAG-UHFFFAOYSA-N 0.000 claims 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims 2
- IWPZKOJSYQZABD-UHFFFAOYSA-N 3,5-dimethoxybenzoic acid Chemical compound COC1=CC(OC)=CC(C(O)=O)=C1 IWPZKOJSYQZABD-UHFFFAOYSA-N 0.000 claims 2
- XHQZJYCNDZAGLW-UHFFFAOYSA-N 3-methoxybenzoic acid Chemical compound COC1=CC=CC(C(O)=O)=C1 XHQZJYCNDZAGLW-UHFFFAOYSA-N 0.000 claims 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 claims 2
- NRPFNQUDKRYCNX-UHFFFAOYSA-N 4-methoxyphenylacetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1 NRPFNQUDKRYCNX-UHFFFAOYSA-N 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 2
- ILUJQPXNXACGAN-UHFFFAOYSA-N O-methylsalicylic acid Chemical compound COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 claims 2
- CMZPKNZWOWXRGM-UHFFFAOYSA-N [3-[(dimethylamino)methyl]-4-hydroxy-4-(3-methoxyphenyl)cyclohexyl] 2-(3-methoxyphenyl)acetate Chemical compound COC1=CC=CC(CC(=O)OC2CC(CN(C)C)C(O)(CC2)C=2C=C(OC)C=CC=2)=C1 CMZPKNZWOWXRGM-UHFFFAOYSA-N 0.000 claims 2
- QAKBHXOZMLCRBV-UHFFFAOYSA-N [3-[(dimethylamino)methyl]-4-hydroxy-4-(3-methoxyphenyl)cyclohexyl] 2-chlorobenzoate Chemical compound COC1=CC=CC(C2(O)C(CC(CC2)OC(=O)C=2C(=CC=CC=2)Cl)CN(C)C)=C1 QAKBHXOZMLCRBV-UHFFFAOYSA-N 0.000 claims 2
- GVJPIDUKBYLMDA-UHFFFAOYSA-N [3-[(dimethylamino)methyl]-4-hydroxy-4-(3-methoxyphenyl)cyclohexyl] 2-fluorobenzoate Chemical compound COC1=CC=CC(C2(O)C(CC(CC2)OC(=O)C=2C(=CC=CC=2)F)CN(C)C)=C1 GVJPIDUKBYLMDA-UHFFFAOYSA-N 0.000 claims 2
- HGYFLWRBOCGRMS-UHFFFAOYSA-N [3-[(dimethylamino)methyl]-4-hydroxy-4-(3-methoxyphenyl)cyclohexyl] 2-methoxybenzoate Chemical compound COC1=CC=CC(C2(O)C(CC(CC2)OC(=O)C=2C(=CC=CC=2)OC)CN(C)C)=C1 HGYFLWRBOCGRMS-UHFFFAOYSA-N 0.000 claims 2
- WXAWRALLUMBOCL-UHFFFAOYSA-N [3-[(dimethylamino)methyl]-4-hydroxy-4-(3-methoxyphenyl)cyclohexyl] 2-phenylacetate Chemical compound COC1=CC=CC(C2(O)C(CC(CC2)OC(=O)CC=2C=CC=CC=2)CN(C)C)=C1 WXAWRALLUMBOCL-UHFFFAOYSA-N 0.000 claims 2
- WFDRAFGKDQRCMR-UHFFFAOYSA-N [3-[(dimethylamino)methyl]-4-hydroxy-4-(3-methoxyphenyl)cyclohexyl] 3,4-dichlorobenzoate Chemical compound COC1=CC=CC(C2(O)C(CC(CC2)OC(=O)C=2C=C(Cl)C(Cl)=CC=2)CN(C)C)=C1 WFDRAFGKDQRCMR-UHFFFAOYSA-N 0.000 claims 2
- VRUCSZVMYVHWQF-UHFFFAOYSA-N [3-[(dimethylamino)methyl]-4-hydroxy-4-(3-methoxyphenyl)cyclohexyl] 3,4-dimethoxybenzoate Chemical compound COC1=CC=CC(C2(O)C(CC(CC2)OC(=O)C=2C=C(OC)C(OC)=CC=2)CN(C)C)=C1 VRUCSZVMYVHWQF-UHFFFAOYSA-N 0.000 claims 2
- CZYBMJNWDSRIGP-UHFFFAOYSA-N [3-[(dimethylamino)methyl]-4-hydroxy-4-(3-methoxyphenyl)cyclohexyl] 3,5-difluorobenzoate Chemical compound COC1=CC=CC(C2(O)C(CC(CC2)OC(=O)C=2C=C(F)C=C(F)C=2)CN(C)C)=C1 CZYBMJNWDSRIGP-UHFFFAOYSA-N 0.000 claims 2
- YNSJLQYIUCLFOP-UHFFFAOYSA-N [3-[(dimethylamino)methyl]-4-hydroxy-4-(3-methoxyphenyl)cyclohexyl] 3-chlorobenzoate Chemical compound COC1=CC=CC(C2(O)C(CC(CC2)OC(=O)C=2C=C(Cl)C=CC=2)CN(C)C)=C1 YNSJLQYIUCLFOP-UHFFFAOYSA-N 0.000 claims 2
- UCXSEDWTDHCDCB-UHFFFAOYSA-N [3-[(dimethylamino)methyl]-4-hydroxy-4-(3-methoxyphenyl)cyclohexyl] 3-fluorobenzoate Chemical compound COC1=CC=CC(C2(O)C(CC(CC2)OC(=O)C=2C=C(F)C=CC=2)CN(C)C)=C1 UCXSEDWTDHCDCB-UHFFFAOYSA-N 0.000 claims 2
- JVQKFSKBXDJXBT-UHFFFAOYSA-N [3-[(dimethylamino)methyl]-4-hydroxy-4-(3-methoxyphenyl)cyclohexyl] 3-methoxybenzoate Chemical compound COC1=CC=CC(C(=O)OC2CC(CN(C)C)C(O)(CC2)C=2C=C(OC)C=CC=2)=C1 JVQKFSKBXDJXBT-UHFFFAOYSA-N 0.000 claims 2
- PTPIIVBAHMMOQS-UHFFFAOYSA-N [3-[(dimethylamino)methyl]-4-hydroxy-4-(3-methoxyphenyl)cyclohexyl] 4-chlorobenzoate Chemical compound COC1=CC=CC(C2(O)C(CC(CC2)OC(=O)C=2C=CC(Cl)=CC=2)CN(C)C)=C1 PTPIIVBAHMMOQS-UHFFFAOYSA-N 0.000 claims 2
- FKUDGSICWDWAGL-UHFFFAOYSA-N [3-[(dimethylamino)methyl]-4-hydroxy-4-(3-methoxyphenyl)cyclohexyl] 4-fluorobenzoate Chemical compound COC1=CC=CC(C2(O)C(CC(CC2)OC(=O)C=2C=CC(F)=CC=2)CN(C)C)=C1 FKUDGSICWDWAGL-UHFFFAOYSA-N 0.000 claims 2
- PSCWHTRYSBAKJP-UHFFFAOYSA-N [3-[(dimethylamino)methyl]-4-hydroxy-4-(3-methoxyphenyl)cyclohexyl] 4-methoxybenzoate Chemical compound C1=CC(OC)=CC=C1C(=O)OC1CC(CN(C)C)C(O)(C=2C=C(OC)C=CC=2)CC1 PSCWHTRYSBAKJP-UHFFFAOYSA-N 0.000 claims 2
- RKUGSIALGNUXHS-UHFFFAOYSA-N [3-[(dimethylamino)methyl]-4-hydroxy-4-(3-methoxyphenyl)cyclohexyl] naphthalene-1-carboxylate Chemical compound COC1=CC=CC(C2(O)C(CC(CC2)OC(=O)C=2C3=CC=CC=C3C=CC=2)CN(C)C)=C1 RKUGSIALGNUXHS-UHFFFAOYSA-N 0.000 claims 2
- IVVJNMPLQRCMHM-UHFFFAOYSA-N [3-[(dimethylamino)methyl]-4-hydroxy-4-(3-methoxyphenyl)cyclohexyl] naphthalene-2-carboxylate Chemical compound COC1=CC=CC(C2(O)C(CC(CC2)OC(=O)C=2C=C3C=CC=CC3=CC=2)CN(C)C)=C1 IVVJNMPLQRCMHM-UHFFFAOYSA-N 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims 2
- UNBAKTOKZNJCOD-UHFFFAOYSA-N 1,4-bis[(4-chlorophenyl)methyl]-2-[(dimethylamino)methyl]cyclohexan-1-ol Chemical compound C1CC(CC=2C=CC(Cl)=CC=2)(O)C(CN(C)C)CC1CC1=CC=C(Cl)C=C1 UNBAKTOKZNJCOD-UHFFFAOYSA-N 0.000 claims 1
- PZSLQARCXYMQAW-UHFFFAOYSA-N 1-(2,3-dichlorophenyl)-2-[(dimethylamino)methyl]-4-[(4-fluorophenyl)methyl]cyclohexan-1-ol Chemical compound C1CC(C=2C(=C(Cl)C=CC=2)Cl)(O)C(CN(C)C)CC1CC1=CC=C(F)C=C1 PZSLQARCXYMQAW-UHFFFAOYSA-N 0.000 claims 1
- ALHXUKTVSYBCNR-UHFFFAOYSA-N 1-(2-bromophenyl)-2-[(dimethylamino)methyl]-4-phenylmethoxycyclohexan-1-ol Chemical compound CN(C)CC1CC(OCC=2C=CC=CC=2)CCC1(O)C1=CC=CC=C1Br ALHXUKTVSYBCNR-UHFFFAOYSA-N 0.000 claims 1
- CILLWNAXMJBHSE-UHFFFAOYSA-N 1-(2-chlorophenyl)-2-[(dimethylamino)methyl]-4-[(4-fluorophenyl)methoxy]cyclohexan-1-ol Chemical compound CN(C)CC1CC(OCC=2C=CC(F)=CC=2)CCC1(O)C1=CC=CC=C1Cl CILLWNAXMJBHSE-UHFFFAOYSA-N 0.000 claims 1
- VTZWHNXEQUVPOA-UHFFFAOYSA-N 1-(2-chlorophenyl)-2-[(dimethylamino)methyl]-4-phenylmethoxycyclohexan-1-ol Chemical compound CN(C)CC1CC(OCC=2C=CC=CC=2)CCC1(O)C1=CC=CC=C1Cl VTZWHNXEQUVPOA-UHFFFAOYSA-N 0.000 claims 1
- IKZDGABCYZJWNL-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-2-[(dimethylamino)methyl]-4-(2-phenylethyl)cyclohexan-1-ol Chemical compound C1CC(C=2C=C(Cl)C(Cl)=CC=2)(O)C(CN(C)C)CC1CCC1=CC=CC=C1 IKZDGABCYZJWNL-UHFFFAOYSA-N 0.000 claims 1
- NGOIMHBBWWZSFR-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-2-[(dimethylamino)methyl]-4-[(4-fluorophenyl)methoxy]cyclohexan-1-ol Chemical compound CN(C)CC1CC(OCC=2C=CC(F)=CC=2)CCC1(O)C1=CC=C(Cl)C(Cl)=C1 NGOIMHBBWWZSFR-UHFFFAOYSA-N 0.000 claims 1
- WLVDQWOMOFVRFI-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-2-[(dimethylamino)methyl]-4-phenylmethoxycyclohexan-1-ol Chemical compound CN(C)CC1CC(OCC=2C=CC=CC=2)CCC1(O)C1=CC=C(Cl)C(Cl)=C1 WLVDQWOMOFVRFI-UHFFFAOYSA-N 0.000 claims 1
- QJUUOJNECMMTJF-UHFFFAOYSA-N 1-(3,4-difluorophenyl)-2-[(dimethylamino)methyl]-4-(2-phenylethyl)cyclohexan-1-ol Chemical compound C1CC(C=2C=C(F)C(F)=CC=2)(O)C(CN(C)C)CC1CCC1=CC=CC=C1 QJUUOJNECMMTJF-UHFFFAOYSA-N 0.000 claims 1
- XLFWVUGSTGMRAN-UHFFFAOYSA-N 1-(3,4-difluorophenyl)-2-[(dimethylamino)methyl]-4-[(4-fluorophenyl)methoxy]cyclohexan-1-ol Chemical compound CN(C)CC1CC(OCC=2C=CC(F)=CC=2)CCC1(O)C1=CC=C(F)C(F)=C1 XLFWVUGSTGMRAN-UHFFFAOYSA-N 0.000 claims 1
- ASHGAGNISKGYIS-UHFFFAOYSA-N 1-(3,4-difluorophenyl)-2-[(dimethylamino)methyl]-4-phenylmethoxycyclohexan-1-ol Chemical compound CN(C)CC1CC(OCC=2C=CC=CC=2)CCC1(O)C1=CC=C(F)C(F)=C1 ASHGAGNISKGYIS-UHFFFAOYSA-N 0.000 claims 1
- XHNLYIWKYBPKSY-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-2-[(dimethylamino)methyl]-4-(2-phenylethyl)cyclohexan-1-ol Chemical compound C1CC(C=2C=C(Cl)C=C(Cl)C=2)(O)C(CN(C)C)CC1CCC1=CC=CC=C1 XHNLYIWKYBPKSY-UHFFFAOYSA-N 0.000 claims 1
- JEWOIXJAYNDQDS-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-2-[(dimethylamino)methyl]-4-[(3-methoxyphenyl)methyl]cyclohexan-1-ol Chemical compound COC1=CC=CC(CC2CC(CN(C)C)C(O)(CC2)C=2C=C(Cl)C=C(Cl)C=2)=C1 JEWOIXJAYNDQDS-UHFFFAOYSA-N 0.000 claims 1
- QDROUMDFUQSKBF-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-2-[(dimethylamino)methyl]-4-[(4-fluorophenyl)methoxy]cyclohexan-1-ol Chemical compound CN(C)CC1CC(OCC=2C=CC(F)=CC=2)CCC1(O)C1=CC(Cl)=CC(Cl)=C1 QDROUMDFUQSKBF-UHFFFAOYSA-N 0.000 claims 1
- HZVPZHMJWJAJHV-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-2-[(dimethylamino)methyl]-4-[(4-fluorophenyl)methyl]cyclohexan-1-ol Chemical compound C1CC(C=2C=C(Cl)C=C(Cl)C=2)(O)C(CN(C)C)CC1CC1=CC=C(F)C=C1 HZVPZHMJWJAJHV-UHFFFAOYSA-N 0.000 claims 1
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- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- C—CHEMISTRY; METALLURGY
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- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/41—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
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- C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/79—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
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- 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
- C07C235/04—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
- C07C235/14—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 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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- 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
- C07C235/54—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 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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- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- 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
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
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- 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
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- 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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- 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
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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- Chemical & Material Sciences (AREA)
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- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
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- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
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Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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DE10049481A DE10049481A1 (de) | 2000-09-29 | 2000-09-29 | Substituierte C-Cyclohexylmethylamin-Derivate |
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ZA200303224B true ZA200303224B (en) | 2004-08-13 |
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ZA200303224A ZA200303224B (en) | 2000-09-29 | 2003-04-24 | Substituted C-cyclohexylmethylamine derivatives. |
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EP (2) | EP1368299B1 (xx) |
JP (1) | JP2004524274A (xx) |
KR (1) | KR100893672B1 (xx) |
CN (1) | CN1547570A (xx) |
AR (1) | AR035062A1 (xx) |
AT (2) | ATE334114T1 (xx) |
AU (2) | AU1397802A (xx) |
BR (1) | BR0114379A (xx) |
CA (1) | CA2423935A1 (xx) |
CY (2) | CY1105247T1 (xx) |
CZ (1) | CZ2003906A3 (xx) |
DE (3) | DE10049481A1 (xx) |
DK (2) | DK1368299T3 (xx) |
EC (1) | ECSP034531A (xx) |
ES (2) | ES2317103T3 (xx) |
HK (2) | HK1080071A1 (xx) |
HU (1) | HUP0303184A3 (xx) |
IL (1) | IL155103A0 (xx) |
MX (1) | MXPA03002348A (xx) |
NO (1) | NO20031386L (xx) |
NZ (2) | NZ545879A (xx) |
PE (1) | PE20030618A1 (xx) |
PL (1) | PL366057A1 (xx) |
PT (2) | PT1368299E (xx) |
RU (1) | RU2295515C2 (xx) |
SI (2) | SI1571140T1 (xx) |
SK (1) | SK3412003A3 (xx) |
WO (1) | WO2002030870A2 (xx) |
ZA (1) | ZA200303224B (xx) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10153347A1 (de) * | 2001-10-29 | 2003-05-08 | Gruenenthal Gmbh | Substituierte 1H-Chinolin-2-on-Verbindungen |
DE10153346A1 (de) | 2001-10-29 | 2004-04-22 | Grünenthal GmbH | Substituierte Indole |
DE10161644A1 (de) * | 2001-12-14 | 2003-06-26 | Gruenenthal Gmbh | N,N'-disubstituierte Piperazin-Verbindungen |
DE10261091A1 (de) * | 2002-12-20 | 2004-07-01 | Grünenthal GmbH | Gesättigte und ungesättigte Heteroarylcycloalkylmethyl-Amine |
DE102004039382A1 (de) * | 2004-08-13 | 2006-02-23 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
DE102005061428A1 (de) * | 2005-12-22 | 2007-08-16 | Grünenthal GmbH | Substituierte Cyclohexylmethyl-Derivate |
TWI496762B (zh) | 2006-07-24 | 2015-08-21 | 製備(1r,2r)-3-(3-二甲胺基-1-乙基-2-甲基-丙基)-酚之方法 | |
MX2009012685A (es) * | 2007-05-31 | 2009-12-14 | Sepracor Inc | Cicloalquilaminas sustituidas con fenilo como inhibidores de la reabsorcion de monoamina. |
CN101906056B (zh) * | 2009-06-04 | 2013-10-30 | 中国科学院广州生物医药与健康研究院 | 作为m2抑制剂的环烷胺类化合物及其应用 |
WO2012100423A1 (en) * | 2011-01-27 | 2012-08-02 | Eli Lilly And Company | Analgesic compounds, methods, and formulations |
CN105837454B (zh) * | 2016-04-21 | 2018-06-08 | 河南师范大学 | 一种3,3-二氟环己基甲胺的合成方法 |
CN112759545B (zh) * | 2019-11-06 | 2022-12-13 | 复旦大学 | 3-(二甲氨基甲基)哌啶-4-醇类衍生物及其制备方法和药物用途 |
US20230027752A1 (en) * | 2019-11-06 | 2023-01-26 | Fudan University | Opioid receptor agonist, preparation method therefor and pharmaceutical use thereof |
CN112759544B (zh) * | 2019-11-06 | 2022-08-26 | 复旦大学 | 3-(二甲氨基甲基)哌啶-4-醇衍生物制备方法和药物用途 |
CN112759546B (zh) * | 2019-11-06 | 2022-08-26 | 复旦大学 | 3-(二甲氨基甲基)哌啶-4-醇衍生物及其制备方法和药物用途 |
CN112759538B (zh) * | 2019-11-06 | 2022-01-18 | 复旦大学 | 3-(二甲氨基甲基)环己-4-醇衍生物及其制备方法和药物用途 |
CN112759587B (zh) * | 2019-11-06 | 2022-12-30 | 复旦大学 | 3-(二甲氨基甲基)哌啶-4-醇类衍生物及其制备方法和药物用途 |
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BE615646A (xx) | 1961-03-27 | 1900-01-01 | ||
US3165428A (en) | 1962-12-27 | 1965-01-12 | Westinghouse Electric Corp | Production of thin goss oriented magnetic materials |
US3975436A (en) | 1974-03-27 | 1976-08-17 | American Home Products Corporation | Benzylamine narcotic antagonists |
DE2614244A1 (de) * | 1976-04-02 | 1977-10-20 | Bayer Ag | Cycloaliphatische triamine |
IL103096A (en) | 1992-09-08 | 1996-12-05 | Chemagis Ltd | Process for purification 2 -]) Dimethylamino (methyl-1-) 3-methoxycinyl (cyclohexanol and its salts. |
DE19525137C2 (de) | 1995-07-11 | 2003-02-27 | Gruenenthal Gmbh | 6-Dimethylaminomethyl-1-phenyl-cyclohexanverbin -dungen als Zwischenprodukte zur Herstellung pharmazeutischer Wirkstoffe |
DE19547766A1 (de) | 1995-12-20 | 1997-06-26 | Gruenenthal Gmbh | 1-Phenyl-2-dimethylaminomethyl-cyclohexan-1-ol-verbindungen als pharmazeutische Wirkstoffe |
DE19609847A1 (de) | 1996-03-13 | 1997-09-18 | Gruenenthal Gmbh | Dimethyl-(3-aryl-but-3-enyl)-aminverbindungen als pharmazeutische Wirkstoffe |
PL197293B1 (pl) | 1998-04-01 | 2008-03-31 | Cardiome Pharma Corp | Nowe eterowe pochodne aminocykloheksylowe, kompozycje zawierające te związki oraz zastosowanie tych związków |
ES2212849T3 (es) | 1998-05-22 | 2004-08-01 | Mallinckrodt Inc. | Sintesis y purificacion mejoradas de hidrocloruro de (r*,r*)-2-((dimetilamino)metil)-1-(3-metoxifenil)ciclohexanol. |
DE19915601A1 (de) * | 1999-04-07 | 2000-10-19 | Gruenenthal Gmbh | 3-Amino-3-arylpropan-1-ol-Derivate, deren Herstellung und Verwendung |
DE19957342A1 (de) | 1999-11-29 | 2001-05-31 | Gruenenthal Gmbh | Verfahren zur Behandlung und/oder Prophylaxe von IL-12-bedingten Erkrankungen |
DE10004926A1 (de) * | 2000-02-04 | 2001-08-09 | Gruenenthal Gmbh | Verfahren zur enzymatischen Racematspaltung von Aminomethyl-Aryl-Cyclohexanol-Derivaten |
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2000
- 2000-09-29 DE DE10049481A patent/DE10049481A1/de not_active Withdrawn
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2001
- 2001-09-28 IL IL15510301A patent/IL155103A0/xx unknown
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- 2001-09-28 SI SI200130896T patent/SI1571140T1/sl unknown
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- 2001-09-28 EP EP01982379A patent/EP1368299B1/de not_active Expired - Lifetime
- 2001-09-28 PL PL01366057A patent/PL366057A1/xx not_active Application Discontinuation
- 2001-09-28 ES ES05011581T patent/ES2317103T3/es not_active Expired - Lifetime
- 2001-09-28 WO PCT/EP2001/011246 patent/WO2002030870A2/de active IP Right Grant
- 2001-09-28 DK DK01982379T patent/DK1368299T3/da active
- 2001-09-28 EP EP05011581A patent/EP1571140B1/de not_active Expired - Lifetime
- 2001-09-28 PT PT05011581T patent/PT1571140E/pt unknown
- 2001-09-28 CZ CZ2003906A patent/CZ2003906A3/cs unknown
- 2001-09-28 NZ NZ545879A patent/NZ545879A/en unknown
- 2001-09-28 DE DE50114491T patent/DE50114491D1/de not_active Expired - Lifetime
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- 2001-09-28 AT AT05011581T patent/ATE414056T1/de active
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2003
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2004
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