ZA200303220B - Substituted 1-aminobutan-3-ol-derivatives. - Google Patents
Substituted 1-aminobutan-3-ol-derivatives. Download PDFInfo
- Publication number
- ZA200303220B ZA200303220B ZA200303220A ZA200303220A ZA200303220B ZA 200303220 B ZA200303220 B ZA 200303220B ZA 200303220 A ZA200303220 A ZA 200303220A ZA 200303220 A ZA200303220 A ZA 200303220A ZA 200303220 B ZA200303220 B ZA 200303220B
- Authority
- ZA
- South Africa
- Prior art keywords
- dimethylaminomethyl
- cyclohexanol
- singly
- unsubstituted
- alkyl
- Prior art date
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- 229920006395 saturated elastomer Polymers 0.000 claims description 77
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- -1 cycloalkyl radicals Chemical class 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 24
- 208000002193 Pain Diseases 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 22
- 208000004454 Hyperalgesia Diseases 0.000 claims description 21
- 239000003814 drug Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 20
- 150000003254 radicals Chemical class 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 230000036407 pain Effects 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 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 12
- 238000011282 treatment Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- 206010053552 allodynia Diseases 0.000 claims description 7
- 230000000202 analgesic effect Effects 0.000 claims description 7
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 7
- 208000000094 Chronic Pain Diseases 0.000 claims description 6
- 208000018737 Parkinson disease Diseases 0.000 claims description 6
- 239000000470 constituent Substances 0.000 claims description 6
- 206010015037 epilepsy Diseases 0.000 claims description 6
- 208000004296 neuralgia Diseases 0.000 claims description 6
- 230000002981 neuropathic effect Effects 0.000 claims description 6
- 208000021722 neuropathic pain Diseases 0.000 claims description 6
- FETATBSBISXMSI-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[(dimethylamino)methyl]-6-(3-methoxyphenyl)cyclohexan-1-ol Chemical compound COC1=CC=CC(C2C(C(CN(C)C)CCC2)(O)C=2C=CC(Cl)=CC=2)=C1 FETATBSBISXMSI-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 208000024891 symptom Diseases 0.000 claims description 5
- MWZYOLGLOVBIOW-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-6-(3-methoxyphenyl)-1-(2-methylphenyl)cyclohexan-1-ol Chemical compound COC1=CC=CC(C2C(C(CN(C)C)CCC2)(O)C=2C(=CC=CC=2)C)=C1 MWZYOLGLOVBIOW-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
- NAXUFNXWXFZVSI-UHFFFAOYSA-N 4-aminobutan-2-ol Chemical class CC(O)CCN NAXUFNXWXFZVSI-UHFFFAOYSA-N 0.000 claims description 4
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- 206010065390 Inflammatory pain Diseases 0.000 claims description 4
- 208000019695 Migraine disease Diseases 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 208000004550 Postoperative Pain Diseases 0.000 claims description 4
- 239000001961 anticonvulsive agent Substances 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 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
- 150000004677 hydrates Chemical class 0.000 claims description 4
- 230000002757 inflammatory effect Effects 0.000 claims description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- DZXKXAHWPLTIOY-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]-2-[(dimethylamino)methyl]-6-(3-methoxyphenyl)cyclohexan-1-ol Chemical compound COC1=CC=CC(C2C(C(CN(C)C)CCC2)(O)CC=2C=C(Cl)C=CC=2)=C1 DZXKXAHWPLTIOY-UHFFFAOYSA-N 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 3
- 206010060800 Hot flush Diseases 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 208000035154 Hyperesthesia Diseases 0.000 claims description 3
- 206010026749 Mania Diseases 0.000 claims description 3
- 206010036376 Postherpetic Neuralgia Diseases 0.000 claims description 3
- 208000005793 Restless legs syndrome Diseases 0.000 claims description 3
- 206010041415 Spastic paralysis Diseases 0.000 claims description 3
- 208000005298 acute pain Diseases 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 239000002249 anxiolytic agent Substances 0.000 claims description 3
- 230000000949 anxiolytic effect Effects 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 230000036651 mood Effects 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
- 206010029864 nystagmus Diseases 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 206010044652 trigeminal neuralgia Diseases 0.000 claims description 3
- RCLRIBRQRIBPCU-UHFFFAOYSA-N 1,2-dibenzyl-6-[(dimethylamino)methyl]cyclohexan-1-ol Chemical compound C=1C=CC=CC=1CC1(O)C(CN(C)C)CCCC1CC1=CC=CC=C1 RCLRIBRQRIBPCU-UHFFFAOYSA-N 0.000 claims description 2
- FVNVSWFKODJJEN-UHFFFAOYSA-N 1-[(2,4-dichlorophenyl)methyl]-2-[(dimethylamino)methyl]-6-(3-methoxyphenyl)cyclohexan-1-ol Chemical compound COC1=CC=CC(C2C(C(CN(C)C)CCC2)(O)CC=2C(=CC(Cl)=CC=2)Cl)=C1 FVNVSWFKODJJEN-UHFFFAOYSA-N 0.000 claims description 2
- PBQXYFRZHSLUCP-UHFFFAOYSA-N 1-[(3,5-dichlorophenyl)methyl]-2-[(dimethylamino)methyl]-6-(3-methoxyphenyl)cyclohexan-1-ol Chemical compound COC1=CC=CC(C2C(C(CN(C)C)CCC2)(O)CC=2C=C(Cl)C=C(Cl)C=2)=C1 PBQXYFRZHSLUCP-UHFFFAOYSA-N 0.000 claims description 2
- UKQYLCRNJLSEJR-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-(2,5-dimethylphenyl)-6-(3-methoxyphenyl)cyclohexan-1-ol Chemical compound COC1=CC=CC(C2C(C(CN(C)C)CCC2)(O)C=2C(=CC=C(C)C=2)C)=C1 UKQYLCRNJLSEJR-UHFFFAOYSA-N 0.000 claims description 2
- WAVAEFYTLAYRHS-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-(2-methoxyphenyl)-6-(3-methoxyphenyl)cyclohexan-1-ol Chemical compound COC1=CC=CC(C2C(C(CN(C)C)CCC2)(O)C=2C(=CC=CC=2)OC)=C1 WAVAEFYTLAYRHS-UHFFFAOYSA-N 0.000 claims description 2
- KEWSLWLTGFEXDF-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-(2-methoxyphenyl)-6-methylcyclohexan-1-ol Chemical compound COC1=CC=CC=C1C1(O)C(CN(C)C)CCCC1C KEWSLWLTGFEXDF-UHFFFAOYSA-N 0.000 claims description 2
- BVLDYZLMQQIHJI-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-(3-fluorophenyl)-6-(3-methoxyphenyl)cyclohexan-1-ol Chemical compound COC1=CC=CC(C2C(C(CN(C)C)CCC2)(O)C=2C=C(F)C=CC=2)=C1 BVLDYZLMQQIHJI-UHFFFAOYSA-N 0.000 claims description 2
- XISKKRDTXZXAAA-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-(3-fluorophenyl)-6-methylcyclohexan-1-ol Chemical compound CC1CCCC(CN(C)C)C1(O)C1=CC=CC(F)=C1 XISKKRDTXZXAAA-UHFFFAOYSA-N 0.000 claims description 2
- IKXDYQUXZUEHRJ-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-(4-fluoro-2-methoxyphenyl)-6-(3-methoxyphenyl)cyclohexan-1-ol Chemical compound COC1=CC=CC(C2C(C(CN(C)C)CCC2)(O)C=2C(=CC(F)=CC=2)OC)=C1 IKXDYQUXZUEHRJ-UHFFFAOYSA-N 0.000 claims description 2
- CNNOVLJWPRYPEO-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-(4-fluorophenyl)-6-methylcyclohexan-1-ol Chemical compound CC1CCCC(CN(C)C)C1(O)C1=CC=C(F)C=C1 CNNOVLJWPRYPEO-UHFFFAOYSA-N 0.000 claims description 2
- JIOBFSSGOHZHSV-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-[(2,5-dimethylphenyl)methyl]-6-methylcyclohexan-1-ol Chemical compound CC1CCCC(CN(C)C)C1(O)CC1=CC(C)=CC=C1C JIOBFSSGOHZHSV-UHFFFAOYSA-N 0.000 claims description 2
- HPPLZTVPCFUJGZ-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-[(3-fluorophenyl)methyl]-6-methylcyclohexan-1-ol Chemical compound CC1CCCC(CN(C)C)C1(O)CC1=CC=CC(F)=C1 HPPLZTVPCFUJGZ-UHFFFAOYSA-N 0.000 claims description 2
- YLNWGEBXBZSLFF-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-[(4-fluorophenyl)methyl]-6-methylcyclohexan-1-ol Chemical compound CC1CCCC(CN(C)C)C1(O)CC1=CC=C(F)C=C1 YLNWGEBXBZSLFF-UHFFFAOYSA-N 0.000 claims description 2
- OJDRVYQDLVSXCW-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-6-(3-methoxyphenyl)-1-(3-phenylpropyl)cyclohexan-1-ol Chemical compound COC1=CC=CC(C2C(C(CN(C)C)CCC2)(O)CCCC=2C=CC=CC=2)=C1 OJDRVYQDLVSXCW-UHFFFAOYSA-N 0.000 claims description 2
- RUMLASXMJYIVJS-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-6-(3-methoxyphenyl)-1-thiophen-2-ylcyclohexan-1-ol Chemical compound COC1=CC=CC(C2C(C(CN(C)C)CCC2)(O)C=2SC=CC=2)=C1 RUMLASXMJYIVJS-UHFFFAOYSA-N 0.000 claims description 2
- QPRWLLBXGFJLJU-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-6-methyl-1-(3-phenylpropyl)cyclohexan-1-ol Chemical compound CC1CCCC(CN(C)C)C1(O)CCCC1=CC=CC=C1 QPRWLLBXGFJLJU-UHFFFAOYSA-N 0.000 claims description 2
- BMFLOHIIWHUABH-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-6-methyl-1-[(2-methylphenyl)methyl]cyclohexan-1-ol Chemical compound CC1CCCC(CN(C)C)C1(O)CC1=CC=CC=C1C BMFLOHIIWHUABH-UHFFFAOYSA-N 0.000 claims description 2
- UVNDJUDEFWQMBZ-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-6-methyl-1-[(3-methylphenyl)methyl]cyclohexan-1-ol Chemical compound CC1CCCC(CN(C)C)C1(O)CC1=CC=CC(C)=C1 UVNDJUDEFWQMBZ-UHFFFAOYSA-N 0.000 claims description 2
- GJARVIBNTWPYSG-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-6-methyl-1-thiophen-2-ylcyclohexan-1-ol Chemical compound CC1CCCC(CN(C)C)C1(O)C1=CC=CS1 GJARVIBNTWPYSG-UHFFFAOYSA-N 0.000 claims description 2
- VOMSTHZVOVVCBB-UHFFFAOYSA-N 2-benzyl-6-[(dimethylamino)methyl]-1-(2-methoxyphenyl)cyclohexan-1-ol Chemical compound COC1=CC=CC=C1C1(O)C(CC=2C=CC=CC=2)CCCC1CN(C)C VOMSTHZVOVVCBB-UHFFFAOYSA-N 0.000 claims description 2
- OJFDMHVZHIQNAG-UHFFFAOYSA-N 2-benzyl-6-[(dimethylamino)methyl]-1-(3-phenylpropyl)cyclohexan-1-ol Chemical compound C=1C=CC=CC=1CCCC1(O)C(CN(C)C)CCCC1CC1=CC=CC=C1 OJFDMHVZHIQNAG-UHFFFAOYSA-N 0.000 claims description 2
- IBTOGPIKRZJJAP-UHFFFAOYSA-N 2-benzyl-6-[(dimethylamino)methyl]-1-(5-fluoro-2-methoxyphenyl)cyclohexan-1-ol Chemical compound COC1=CC=C(F)C=C1C1(O)C(CC=2C=CC=CC=2)CCCC1CN(C)C IBTOGPIKRZJJAP-UHFFFAOYSA-N 0.000 claims description 2
- SSORYTHOIZUAKT-UHFFFAOYSA-N 2-benzyl-6-[(dimethylamino)methyl]-1-[(2,5-dimethylphenyl)methyl]cyclohexan-1-ol Chemical compound C=1C(C)=CC=C(C)C=1CC1(O)C(CN(C)C)CCCC1CC1=CC=CC=C1 SSORYTHOIZUAKT-UHFFFAOYSA-N 0.000 claims description 2
- RSWDNBMHTOFBLR-UHFFFAOYSA-N 2-benzyl-6-[(dimethylamino)methyl]-1-[(2-methylphenyl)methyl]cyclohexan-1-ol Chemical compound C=1C=CC=C(C)C=1CC1(O)C(CN(C)C)CCCC1CC1=CC=CC=C1 RSWDNBMHTOFBLR-UHFFFAOYSA-N 0.000 claims description 2
- NICIIPPFLGFTIW-UHFFFAOYSA-N 2-benzyl-6-[(dimethylamino)methyl]-1-ethenylcyclohexan-1-ol Chemical compound C=CC1(O)C(CN(C)C)CCCC1CC1=CC=CC=C1 NICIIPPFLGFTIW-UHFFFAOYSA-N 0.000 claims description 2
- ZUARUQUWOUGXRH-UHFFFAOYSA-N 2-benzyl-6-[(dimethylamino)methyl]-1-phenylcyclohexan-1-ol Chemical compound C=1C=CC=CC=1C1(O)C(CN(C)C)CCCC1CC1=CC=CC=C1 ZUARUQUWOUGXRH-UHFFFAOYSA-N 0.000 claims description 2
- JOYVANAGHGSNKK-UHFFFAOYSA-N 2-benzyl-6-[(dimethylamino)methyl]-1-thiophen-2-ylcyclohexan-1-ol Chemical compound C=1C=CSC=1C1(O)C(CN(C)C)CCCC1CC1=CC=CC=C1 JOYVANAGHGSNKK-UHFFFAOYSA-N 0.000 claims description 2
- GRLJZAPDTLDPER-UHFFFAOYSA-N 3-[2-benzyl-6-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenol Chemical compound C=1C=CC(O)=CC=1C1(O)C(CN(C)C)CCCC1CC1=CC=CC=C1 GRLJZAPDTLDPER-UHFFFAOYSA-N 0.000 claims description 2
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000003840 hydrochlorides Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 208000013586 Complex regional pain syndrome type 1 Diseases 0.000 claims 4
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- IDONQOKHKOIMLN-UHFFFAOYSA-N 1-(2-chloro-3-fluorophenyl)-2-(dimethylamino)-2,6-dimethylcyclohexan-1-ol Chemical compound CC1CCCC(C)(N(C)C)C1(O)C1=CC=CC(F)=C1Cl IDONQOKHKOIMLN-UHFFFAOYSA-N 0.000 claims 1
- YHMRAASDVDTARD-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]-2-[(dimethylamino)methyl]-6-methylcyclohexan-1-ol Chemical compound CC1CCCC(CN(C)C)C1(O)CC1=CC=CC(Cl)=C1 YHMRAASDVDTARD-UHFFFAOYSA-N 0.000 claims 1
- ORBYPOOUEFZAQD-UHFFFAOYSA-N 1-[3-(dimethylamino)-1-phenylpropyl]-2-(3-methoxyphenyl)cyclohexan-1-ol Chemical compound CN(C)CCC(C1=CC=CC=C1)C1(CCCCC1C1=CC(=CC=C1)OC)O ORBYPOOUEFZAQD-UHFFFAOYSA-N 0.000 claims 1
- FRGXCFKDEMSKAT-UHFFFAOYSA-N 1-[3-(dimethylamino)-1-phenylpropyl]-2-methylcyclohexan-1-ol Chemical compound CN(C)CCC(C1=CC=CC=C1)C1(CCCCC1C)O FRGXCFKDEMSKAT-UHFFFAOYSA-N 0.000 claims 1
- JHPGYOCHGFASFP-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1,6-bis(3-methoxyphenyl)cyclohexan-1-ol Chemical compound COC1=CC=CC(C2C(C(CN(C)C)CCC2)(O)C=2C=C(OC)C=CC=2)=C1 JHPGYOCHGFASFP-UHFFFAOYSA-N 0.000 claims 1
- CTZGIAFULKDIHG-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-(4-methoxyphenyl)-6-methylcyclohexan-1-ol Chemical compound C1=CC(OC)=CC=C1C1(O)C(CN(C)C)CCCC1C CTZGIAFULKDIHG-UHFFFAOYSA-N 0.000 claims 1
- HHXYVEHVBADAID-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-6-(3-methoxyphenyl)-1-(4-methylphenyl)cyclohexan-1-ol Chemical compound COC1=CC=CC(C2C(C(CN(C)C)CCC2)(O)C=2C=CC(C)=CC=2)=C1 HHXYVEHVBADAID-UHFFFAOYSA-N 0.000 claims 1
- VDGDZLJWSDDKTN-UHFFFAOYSA-N 2-benzyl-1-(3,5-dichlorophenyl)-6-(dimethylamino)-2-methylcyclohexan-1-ol Chemical compound C=1C(Cl)=CC(Cl)=CC=1C1(O)C(N(C)C)CCCC1(C)CC1=CC=CC=C1 VDGDZLJWSDDKTN-UHFFFAOYSA-N 0.000 claims 1
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- JXRJOHRBNONWPF-UHFFFAOYSA-N 2-benzyl-1-[(3-chlorophenyl)methyl]-6-(dimethylamino)-2-methylcyclohexan-1-ol Chemical compound C=1C=CC(Cl)=CC=1CC1(O)C(N(C)C)CCCC1(C)CC1=CC=CC=C1 JXRJOHRBNONWPF-UHFFFAOYSA-N 0.000 claims 1
- NMZKYSZQCCSATN-UHFFFAOYSA-N 2-benzyl-1-[(4-chlorophenyl)methyl]-6-(dimethylamino)-2-methylcyclohexan-1-ol Chemical compound C=1C=C(Cl)C=CC=1CC1(O)C(N(C)C)CCCC1(C)CC1=CC=CC=C1 NMZKYSZQCCSATN-UHFFFAOYSA-N 0.000 claims 1
- ZHNMPOIUOMBDPU-UHFFFAOYSA-N 2-benzyl-6-[(dimethylamino)methyl]-1-(2-methylphenyl)cyclohexan-1-ol Chemical compound C=1C=CC=C(C)C=1C1(O)C(CN(C)C)CCCC1CC1=CC=CC=C1 ZHNMPOIUOMBDPU-UHFFFAOYSA-N 0.000 claims 1
- YNHVNUBXGBHGIM-UHFFFAOYSA-N 2-benzyl-6-[(dimethylamino)methyl]-1-(4-methoxyphenyl)cyclohexan-1-ol Chemical compound C1=CC(OC)=CC=C1C1(O)C(CC=2C=CC=CC=2)CCCC1CN(C)C YNHVNUBXGBHGIM-UHFFFAOYSA-N 0.000 claims 1
- REQHUZARNFPSBS-UHFFFAOYSA-N 3-[3-[(dimethylamino)methyl]-2-(4-fluorophenyl)-2-hydroxycyclohexyl]phenol Chemical compound C=1C=C(F)C=CC=1C1(O)C(CN(C)C)CCCC1C1=CC=CC(O)=C1 REQHUZARNFPSBS-UHFFFAOYSA-N 0.000 claims 1
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- 150000002902 organometallic compounds Chemical class 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
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Classifications
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- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/74—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/42—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- 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
- C07D333/26—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 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/32—Oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring 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
- C07C2601/14—The ring being saturated
Landscapes
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- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Surgery (AREA)
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- Reproductive Health (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (1)
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DE10049483A DE10049483A1 (de) | 2000-09-29 | 2000-09-29 | Substituierte 1-Aminobutan-3-ol-Derivate |
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ZA200303220A ZA200303220B (en) | 2000-09-29 | 2003-04-24 | Substituted 1-aminobutan-3-ol-derivatives. |
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DE10049483A1 (de) * | 2000-09-29 | 2002-05-02 | Gruenenthal Gmbh | Substituierte 1-Aminobutan-3-ol-Derivate |
AU2002337863B2 (en) | 2001-10-16 | 2007-10-11 | Endo Pharmaceuticals Inc. | Carbinols for the treatment of neuropathic dysfunction |
BR0306811A (pt) * | 2002-01-11 | 2004-10-26 | Sankyo Co | Composto, éster farmacologicamente aceitável do mesmo, composição farmacêutica e métodos para prevenção ou tratamento de doenças autoimunes, da artrite reumatóide e da rejeição causada pelo transplante de vários órgãos em um mamìfero |
US8128957B1 (en) | 2002-02-21 | 2012-03-06 | Valeant International (Barbados) Srl | Modified release compositions of at least one form of tramadol |
US20050182056A9 (en) * | 2002-02-21 | 2005-08-18 | Seth Pawan | Modified release formulations of at least one form of tramadol |
AU2003283410A1 (en) | 2002-11-22 | 2004-06-18 | Grunenthal Gmbh | Combination of selected analgesics and cox-ii inhibitors |
CA2557536C (en) | 2004-02-24 | 2010-07-13 | Sankyo Company Limited | Amino alcohol compound |
RU2470011C2 (ru) * | 2007-05-31 | 2012-12-20 | Сепракор Инк. | Циклоалкиламины, содержащие в качестве заместителя фенил, как ингибиторы обратного захвата моноаминов |
US20100183600A1 (en) * | 2008-12-05 | 2010-07-22 | Arqule, Inc. | RAF Inhibitors and Their Uses |
ES2343050B1 (es) * | 2008-12-16 | 2011-06-14 | Chemo Iberica, S.A. | Procedimiento para la preparacion de desvenlafaxina y sus sales de adicion de acido farmaceuticamente aceptables. |
WO2012100423A1 (en) * | 2011-01-27 | 2012-08-02 | Eli Lilly And Company | Analgesic compounds, methods, and formulations |
WO2017125351A1 (en) * | 2016-01-21 | 2017-07-27 | Laboratorios Lesvi Sl | Process for preparing (( r)-3-[(-1-methylpyrrolidin-2-yl)methyl]-5-(2-phenylsulfonylethyl)-1h-indole |
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US3652589A (en) * | 1967-07-27 | 1972-03-28 | Gruenenthal Chemie | 1-(m-substituted phenyl)-2-aminomethyl cyclohexanols |
ZA732238B (en) * | 1972-04-06 | 1974-01-30 | American Home Prod | Benzylamine analgesics |
US4155935A (en) | 1973-03-26 | 1979-05-22 | American Home Products Corporation | Benzylamine analgesics |
DE19525137C2 (de) * | 1995-07-11 | 2003-02-27 | Gruenenthal Gmbh | 6-Dimethylaminomethyl-1-phenyl-cyclohexanverbin -dungen als Zwischenprodukte zur Herstellung pharmazeutischer Wirkstoffe |
US6017963A (en) * | 1995-11-14 | 2000-01-25 | Euro-Celtique, S.A. | Formulation for intranasal administration |
DE19547766A1 (de) * | 1995-12-20 | 1997-06-26 | Gruenenthal Gmbh | 1-Phenyl-2-dimethylaminomethyl-cyclohexan-1-ol-verbindungen als pharmazeutische Wirkstoffe |
DE19601744C2 (de) | 1996-01-19 | 1998-04-16 | Gruenenthal Gmbh | Verfahren zur Herstellung der Enantiomeren von O-Demethyltramadol |
DE19609847A1 (de) * | 1996-03-13 | 1997-09-18 | Gruenenthal Gmbh | Dimethyl-(3-aryl-but-3-enyl)-aminverbindungen als pharmazeutische Wirkstoffe |
US5919826A (en) * | 1996-10-24 | 1999-07-06 | Algos Pharmaceutical Corporation | Method of alleviating pain |
US6245804B1 (en) * | 1997-05-30 | 2001-06-12 | Schering Aktiengesellschaft | Nonsteroidal gestagens |
JP2001510180A (ja) * | 1997-07-15 | 2001-07-31 | ラシンスキィ・リミテッド | トラマドール、その塩酸塩、及びそれらの製造方法 |
DE69913955T2 (de) * | 1998-05-22 | 2004-12-16 | Mallinckrodt, Inc. | Ein verbessertes synthese- und reinigungsverfahren für (r*,r*)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl) cyclohexanol hydrochlorid |
ES2141688B1 (es) * | 1998-11-06 | 2001-02-01 | Vita Invest Sa | Nuevos esteres derivados de compuestos fenil-ciclohexil sustituidos. |
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DE60016602T2 (de) * | 1999-08-20 | 2005-11-03 | Ortho-Mcneil Pharmaceutical, Inc. | Zusammensetzung enthaltend ein tramadol und ein antikonvulsives arzneimittel |
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DE10048714A1 (de) * | 2000-09-30 | 2002-04-11 | Gruenenthal Gmbh | 5-Amino-1-penlen-3-ol-Derivate |
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WO2003048113A1 (en) * | 2001-11-30 | 2003-06-12 | Sepracor Inc. | Tramadol analogs and uses thereof |
-
2000
- 2000-09-29 DE DE10049483A patent/DE10049483A1/de not_active Withdrawn
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2001
- 2001-09-28 CN CNA018196454A patent/CN1478067A/zh active Pending
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