PT1751093E - Derivados de ácido ciclo-hexilacético substituídos - Google Patents
Derivados de ácido ciclo-hexilacético substituídos Download PDFInfo
- Publication number
- PT1751093E PT1751093E PT05745355T PT05745355T PT1751093E PT 1751093 E PT1751093 E PT 1751093E PT 05745355 T PT05745355 T PT 05745355T PT 05745355 T PT05745355 T PT 05745355T PT 1751093 E PT1751093 E PT 1751093E
- Authority
- PT
- Portugal
- Prior art keywords
- dimethylamino
- mmol
- indol
- fluorophenyl
- acetamide hydrochloride
- Prior art date
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- LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical class OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 57
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 230000008569 process Effects 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 9
- -1 benzodioxolanyl Chemical group 0.000 claims description 281
- 239000000203 mixture Substances 0.000 claims description 68
- 229920006395 saturated elastomer Polymers 0.000 claims description 58
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 239000003814 drug Substances 0.000 claims description 26
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 24
- 208000002193 Pain Diseases 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 22
- 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 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 19
- 125000004076 pyridyl group Chemical group 0.000 claims description 18
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical class [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 17
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 16
- 229940017219 methyl propionate Drugs 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 16
- 125000001544 thienyl group Chemical group 0.000 claims description 16
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 15
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 14
- 125000002541 furyl group Chemical group 0.000 claims description 14
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000001041 indolyl group Chemical group 0.000 claims description 13
- 230000036407 pain Effects 0.000 claims description 13
- 150000007513 acids Chemical class 0.000 claims description 12
- 230000036571 hydration Effects 0.000 claims description 12
- 238000006703 hydration reaction Methods 0.000 claims description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 12
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 11
- 150000001768 cations Chemical class 0.000 claims description 11
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 11
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 11
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 10
- 239000003153 chemical reaction reagent Substances 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 239000013543 active substance Substances 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 229940005483 opioid analgesics Drugs 0.000 claims description 9
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
- LIFZJFNOUKJNIN-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexyl]-n-(3-phenylpropyl)acetamide Chemical compound C1CC(N(C)C)(C=2C=C(F)C=CC=2)CCC1CC(=O)NCCCC1=CC=CC=C1 LIFZJFNOUKJNIN-UHFFFAOYSA-N 0.000 claims description 8
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 8
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
- XUYJLQHKOGNDPB-UHFFFAOYSA-N phosphonoacetic acid Chemical class OC(=O)CP(O)(O)=O XUYJLQHKOGNDPB-UHFFFAOYSA-N 0.000 claims description 7
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 6
- BRNXKDIARBAMHE-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-(4-fluorophenyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1=CC(=O)NC1=CC=C(F)C=C1 BRNXKDIARBAMHE-UHFFFAOYSA-N 0.000 claims description 6
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 6
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 6
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- 208000000094 Chronic Pain Diseases 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 230000003197 catalytic effect Effects 0.000 claims description 6
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 6
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 229910052697 platinum Inorganic materials 0.000 claims description 6
- 229910052703 rhodium Inorganic materials 0.000 claims description 6
- 239000010948 rhodium Substances 0.000 claims description 6
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 5
- JOKLEJREDCNIKD-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexyl]-n-[1-(1h-indol-3-yl)propan-2-yl]acetamide;hydrochloride Chemical compound Cl.C=1NC2=CC=CC=C2C=1CC(C)NC(=O)CC(CC1)CCC1(N(C)C)C1=CC=CC(F)=C1 JOKLEJREDCNIKD-UHFFFAOYSA-N 0.000 claims description 5
- ZUTROUQLHSKEOI-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(4-fluorophenyl)cyclohexylidene]-n-[2-(1h-indol-3-yl)ethyl]acetamide;hydrochloride Chemical compound Cl.C1CC(=CC(=O)NCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=C(F)C=C1 ZUTROUQLHSKEOI-UHFFFAOYSA-N 0.000 claims description 5
- OOQCEGHEPLEHBR-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-(3-phenylpropyl)acetamide Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1CC(=O)NCCCC1=CC=CC=C1 OOQCEGHEPLEHBR-UHFFFAOYSA-N 0.000 claims description 5
- XVNCJNDEVIOODN-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-[5-(1h-indol-3-yl)pentyl]acetamide;hydrochloride Chemical compound Cl.C1CC(=CC(=O)NCCCCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 XVNCJNDEVIOODN-UHFFFAOYSA-N 0.000 claims description 5
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 5
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 5
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 5
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 5
- 230000003444 anaesthetic effect Effects 0.000 claims description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- KNTPZTDIOYUBJC-UHFFFAOYSA-N n-benzyl-2-[4-(dimethylamino)-4-phenylcyclohexylidene]acetamide Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1=CC(=O)NCC1=CC=CC=C1 KNTPZTDIOYUBJC-UHFFFAOYSA-N 0.000 claims description 5
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 5
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 5
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 4
- RXQWCUNKUKVDHD-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexylidene]-n-(3-phenylpropyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=C(F)C=CC=2)CCC1=CC(=O)NCCCC1=CC=CC=C1 RXQWCUNKUKVDHD-UHFFFAOYSA-N 0.000 claims description 4
- CJYQKUZVHJLIGS-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexylidene]-n-[2-(1h-indol-3-yl)ethyl]acetamide;hydrochloride Chemical compound Cl.C1CC(=CC(=O)NCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC(F)=C1 CJYQKUZVHJLIGS-UHFFFAOYSA-N 0.000 claims description 4
- QQPIWEXJHHUYSU-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(4-fluorophenyl)cyclohexylidene]-n-(3-phenylpropyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC(F)=CC=2)CCC1=CC(=O)NCCCC1=CC=CC=C1 QQPIWEXJHHUYSU-UHFFFAOYSA-N 0.000 claims description 4
- PROHEZYFXPIGLK-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-(4-phenylbutyl)acetamide Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1CC(=O)NCCCCC1=CC=CC=C1 PROHEZYFXPIGLK-UHFFFAOYSA-N 0.000 claims description 4
- VFVKWRQVGDJTJB-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-[1-(1h-indol-3-yl)propan-2-yl]acetamide;hydrochloride Chemical compound Cl.C=1NC2=CC=CC=C2C=1CC(C)NC(=O)CC(CC1)CCC1(N(C)C)C1=CC=CC=C1 VFVKWRQVGDJTJB-UHFFFAOYSA-N 0.000 claims description 4
- YLKSRBBBJYTVKJ-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-[3-(1h-indol-3-yl)propyl]acetamide;hydrochloride Chemical compound Cl.C1CC(CC(=O)NCCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 YLKSRBBBJYTVKJ-UHFFFAOYSA-N 0.000 claims description 4
- LULRVVPEJPXSTK-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-[5-(1h-indol-3-yl)pentyl]acetamide;hydrochloride Chemical compound Cl.C1CC(CC(=O)NCCCCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 LULRVVPEJPXSTK-UHFFFAOYSA-N 0.000 claims description 4
- JHZAXZMVHGRBBU-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-[6-(1h-indol-3-yl)hexyl]acetamide;hydrochloride Chemical compound Cl.C1CC(CC(=O)NCCCCCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 JHZAXZMVHGRBBU-UHFFFAOYSA-N 0.000 claims description 4
- BRQVUJAVGATRDQ-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-(1h-indol-3-ylmethyl)acetamide;hydrochloride Chemical compound Cl.C1CC(=CC(=O)NCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 BRQVUJAVGATRDQ-UHFFFAOYSA-N 0.000 claims description 4
- PLHMGPYQBIEXPI-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-(2-phenylethyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1=CC(=O)NCCC1=CC=CC=C1 PLHMGPYQBIEXPI-UHFFFAOYSA-N 0.000 claims description 4
- SVHZXTOUDQHWIH-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-(3-phenylpropyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1=CC(=O)NCCCC1=CC=CC=C1 SVHZXTOUDQHWIH-UHFFFAOYSA-N 0.000 claims description 4
- RTBXXECSCDIAOA-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-(4-phenylbutyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1=CC(=O)NCCCCC1=CC=CC=C1 RTBXXECSCDIAOA-UHFFFAOYSA-N 0.000 claims description 4
- NSDOZTVPWBRTLG-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-[4-(1h-indol-3-yl)butyl]acetamide;hydrochloride Chemical compound Cl.C1CC(=CC(=O)NCCCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 NSDOZTVPWBRTLG-UHFFFAOYSA-N 0.000 claims description 4
- JMILVWBBDLLQBD-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-[6-(1h-indol-3-yl)hexyl]acetamide;hydrochloride Chemical compound Cl.C1CC(=CC(=O)NCCCCCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 JMILVWBBDLLQBD-UHFFFAOYSA-N 0.000 claims description 4
- KMTAMTDLIBHTFP-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-pyridin-2-ylcyclohexyl]-n-(3-phenylpropyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2N=CC=CC=2)CCC1CC(=O)NCCCC1=CC=CC=C1 KMTAMTDLIBHTFP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 4
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 4
- 150000001718 carbodiimides Chemical class 0.000 claims description 4
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 206010061428 decreased appetite Diseases 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- ZGELMQCVXODCBP-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexyl]-n-[2-(1h-indol-3-yl)ethyl]acetamide;hydrochloride Chemical compound Cl.C1CC(CC(=O)NCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC(F)=C1 ZGELMQCVXODCBP-UHFFFAOYSA-N 0.000 claims description 3
- KCIOTZNIJIPFON-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexylidene]-n-[1-(1h-indol-3-yl)propan-2-yl]acetamide;hydrochloride Chemical compound Cl.C=1NC2=CC=CC=C2C=1CC(C)NC(=O)C=C(CC1)CCC1(N(C)C)C1=CC=CC(F)=C1 KCIOTZNIJIPFON-UHFFFAOYSA-N 0.000 claims description 3
- QRLCIWHWUJFNRB-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(4-fluorophenyl)cyclohexyl]-n-(3-phenylpropyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC(F)=CC=2)CCC1CC(=O)NCCCC1=CC=CC=C1 QRLCIWHWUJFNRB-UHFFFAOYSA-N 0.000 claims description 3
- NLOJFZZRPQCNMS-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(4-fluorophenyl)cyclohexylidene]-n-[1-(1h-indol-3-yl)propan-2-yl]acetamide;hydrochloride Chemical compound Cl.C=1NC2=CC=CC=C2C=1CC(C)NC(=O)C=C(CC1)CCC1(N(C)C)C1=CC=C(F)C=C1 NLOJFZZRPQCNMS-UHFFFAOYSA-N 0.000 claims description 3
- IRJYVPBUAJAONT-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-(4-fluorophenyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1CC(=O)NC1=CC=C(F)C=C1 IRJYVPBUAJAONT-UHFFFAOYSA-N 0.000 claims description 3
- KMNXHAOISILVMZ-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-(4-methylphenyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1CC(=O)NC1=CC=C(C)C=C1 KMNXHAOISILVMZ-UHFFFAOYSA-N 0.000 claims description 3
- DLENHNHTFWCBCK-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-phenylacetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1CC(=O)NC1=CC=CC=C1 DLENHNHTFWCBCK-UHFFFAOYSA-N 0.000 claims description 3
- WGDVJTWVUJBWOU-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-[(4-fluorophenyl)methyl]acetamide Chemical compound C1CC(N(C)C)(C=2C=CC=CC=2)CCC1=CC(=O)NCC1=CC=C(F)C=C1 WGDVJTWVUJBWOU-UHFFFAOYSA-N 0.000 claims description 3
- XXKVRGSLYDVPOC-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-[1-(1h-indol-3-yl)propan-2-yl]acetamide;hydrochloride Chemical compound Cl.C=1NC2=CC=CC=C2C=1CC(C)NC(=O)C=C(CC1)CCC1(N(C)C)C1=CC=CC=C1 XXKVRGSLYDVPOC-UHFFFAOYSA-N 0.000 claims description 3
- HCMXPFDHWXHWDG-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-pyridin-2-ylcyclohexyl]-n-[2-(1h-indol-3-yl)ethyl]acetamide;hydrochloride Chemical compound Cl.C1CC(CC(=O)NCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=N1 HCMXPFDHWXHWDG-UHFFFAOYSA-N 0.000 claims description 3
- LWCOSZMDBZTTMB-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-pyridin-2-ylcyclohexylidene]-n-(3-phenylpropyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2N=CC=CC=2)CCC1=CC(=O)NCCCC1=CC=CC=C1 LWCOSZMDBZTTMB-UHFFFAOYSA-N 0.000 claims description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
- 208000009132 Catalepsy Diseases 0.000 claims description 3
- 208000020401 Depressive disease Diseases 0.000 claims description 3
- 206010012735 Diarrhoea Diseases 0.000 claims description 3
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- 208000026139 Memory disease Diseases 0.000 claims description 3
- 208000004880 Polyuria Diseases 0.000 claims description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 206010046543 Urinary incontinence Diseases 0.000 claims description 3
- 206010047853 Waxy flexibility Diseases 0.000 claims description 3
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- 238000010626 work up procedure Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P1/12—Antidiarrhoeals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Dermatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Nutrition Science (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004023507A DE102004023507A1 (de) | 2004-05-10 | 2004-05-10 | Substituierte Cyclohexylessigsäure-Derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PT1751093E true PT1751093E (pt) | 2010-11-29 |
Family
ID=34968613
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT05745355T PT1751093E (pt) | 2004-05-10 | 2005-05-06 | Derivados de ácido ciclo-hexilacético substituídos |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8017630B2 (https=) |
| EP (1) | EP1751093B1 (https=) |
| JP (1) | JP4852536B2 (https=) |
| AT (1) | ATE483679T1 (https=) |
| CA (1) | CA2563017C (https=) |
| CY (1) | CY1111327T1 (https=) |
| DE (2) | DE102004023507A1 (https=) |
| DK (1) | DK1751093T3 (https=) |
| ES (1) | ES2353390T3 (https=) |
| PL (1) | PL1751093T3 (https=) |
| PT (1) | PT1751093E (https=) |
| SI (1) | SI1751093T1 (https=) |
| WO (1) | WO2005110976A1 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090215725A1 (en) * | 2008-02-26 | 2009-08-27 | Grunenthal Gmbh | Substituted 4-aminocyclohexane derivatives |
| ES2375543T3 (es) | 2008-03-27 | 2012-03-01 | Grünenthal GmbH | Derivados de espiro(5.5)undecano. |
| CN102046591B (zh) | 2008-03-27 | 2014-12-03 | 格吕伦塔尔有限公司 | 羟甲基环己胺 |
| AU2009228647B2 (en) | 2008-03-27 | 2013-07-04 | Grunenthal Gmbh | Substituted spirocyclic cyclohexane derivatives |
| ES2464102T3 (es) | 2008-03-27 | 2014-05-30 | Grünenthal GmbH | Derivados de 4-aminociclohexano sustituidos |
| 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 |
| US20090298834A1 (en) * | 2008-06-02 | 2009-12-03 | Hassan Pajouhesh | 4-(aminomethyl)cyclohexanamine derivatives as calcium channel blockers |
| RS55943B1 (sr) | 2013-06-24 | 2017-09-29 | Merck Patent Gmbh | Ftalazin derivati |
| CN106535884A (zh) | 2014-06-06 | 2017-03-22 | 弗雷克萨斯生物科学公司 | 免疫调节剂 |
| MX2017005462A (es) * | 2014-11-05 | 2017-07-28 | Flexus Biosciences Inc | Agentes inmunorreguladores. |
| UY36391A (es) * | 2014-11-05 | 2016-06-01 | Flexus Biosciences Inc | Compuestos moduladores de la enzima indolamina 2,3-dioxigenasa (ido1), sus métodos de síntesis y composiciones farmacèuticas que las contienen |
| UY36390A (es) | 2014-11-05 | 2016-06-01 | Flexus Biosciences Inc | Compuestos moduladores de la enzima indolamina 2,3-dioxigenasa (ido), sus métodos de síntesis y composiciones farmacéuticas que los contienen |
| CN114340670B (zh) | 2019-07-11 | 2026-02-17 | 普拉克西斯精密药物股份有限公司 | T-型钙通道调节剂的制剂及其使用方法 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4115589A (en) * | 1977-05-17 | 1978-09-19 | The Upjohn Company | Compounds, compositions and method of use |
| US4366172A (en) * | 1977-09-29 | 1982-12-28 | The Upjohn Company | 4-Amino-cyclohexanols, their pharmaceutical compositions and methods of use |
| US4212878A (en) * | 1978-01-26 | 1980-07-15 | The Upjohn Company | Phenylacetamide derivative analgesics |
| US4346101A (en) * | 1980-12-08 | 1982-08-24 | The Upjohn Company | Benzamide derivative analgesics |
| DE3924304A1 (de) * | 1989-07-22 | 1991-01-31 | Bayer Ag | Neue fluorierte cyclohexanderivate, verfahren und zwischenprodukte zu deren herstellung und die verwendung der neuen fluorierten cyclohexanderivate als fungizide und zwischenprodukte |
| US5304479A (en) * | 1991-12-06 | 1994-04-19 | Diagnostic Reagents, Inc. | Phencyclidine compounds and assays for its determination |
| US5239110A (en) * | 1992-12-30 | 1993-08-24 | Sterling Winthrop, Inc. | Phenylcyclohexanol derivatives as agents for treating CNS disorders |
| CA2373855A1 (en) * | 1999-05-12 | 2000-11-23 | Solvay Pharmaceuticals B.V. | Method of treating psychotic disorders |
| DE19939044A1 (de) | 1999-08-18 | 2001-03-15 | Gruenenthal Gmbh | Verwendung von Morphinanderivaten als Arzneimittel |
| DE19963175A1 (de) | 1999-12-27 | 2001-07-12 | Gruenenthal Gmbh | Verwendung von substituierten 4-Amino-1-phenylbutan-2-ol-Verbindungen als Arzneimittel |
| GB0012240D0 (en) * | 2000-05-19 | 2000-07-12 | Merck Sharp & Dohme | Therapeutic agents |
| US7138397B2 (en) * | 2000-10-06 | 2006-11-21 | Tanabe Seiyaku Co., Ltd. | Nitrogenous 5-membered ring compounds |
| 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 |
| US6818772B2 (en) * | 2002-02-22 | 2004-11-16 | Abbott Laboratories | Antagonists of melanin concentrating hormone effects on the melanin concentrating hormone receptor |
| AU2003221178B2 (en) * | 2002-03-28 | 2006-06-15 | Tanabe Seiyaku Co., Ltd. | Benzofuran derivative |
| JP4329382B2 (ja) * | 2002-04-04 | 2009-09-09 | 田辺三菱製薬株式会社 | 医薬組成物 |
| WO2004022535A1 (ja) * | 2002-08-28 | 2004-03-18 | Yamanouchi Pharmaceutical Co., Ltd. | アクリルアミド誘導体 |
| DE10252666A1 (de) * | 2002-11-11 | 2004-08-05 | Grünenthal GmbH | N-Piperidyl-cyclohexan-Derivate |
| DE10252650A1 (de) * | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Cyclohexyl-Harnstoff-Derivate |
| WO2006040646A1 (en) * | 2004-10-14 | 2006-04-20 | Pfizer, Inc. | Benzimidazole or indole amides as inhibitors of pin1 |
-
2004
- 2004-05-10 DE DE102004023507A patent/DE102004023507A1/de not_active Withdrawn
-
2005
- 2005-05-06 DK DK05745355.7T patent/DK1751093T3/da active
- 2005-05-06 ES ES05745355T patent/ES2353390T3/es not_active Expired - Lifetime
- 2005-05-06 PL PL05745355T patent/PL1751093T3/pl unknown
- 2005-05-06 SI SI200531192T patent/SI1751093T1/sl unknown
- 2005-05-06 CA CA2563017A patent/CA2563017C/en not_active Expired - Fee Related
- 2005-05-06 DE DE502005010342T patent/DE502005010342D1/de not_active Expired - Lifetime
- 2005-05-06 JP JP2007512029A patent/JP4852536B2/ja not_active Expired - Fee Related
- 2005-05-06 PT PT05745355T patent/PT1751093E/pt unknown
- 2005-05-06 EP EP05745355A patent/EP1751093B1/de not_active Expired - Lifetime
- 2005-05-06 AT AT05745355T patent/ATE483679T1/de active
- 2005-05-06 WO PCT/EP2005/004909 patent/WO2005110976A1/de not_active Ceased
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2006
- 2006-11-09 US US11/594,945 patent/US8017630B2/en not_active Expired - Fee Related
-
2010
- 2010-11-24 CY CY20101101057T patent/CY1111327T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2007536319A (ja) | 2007-12-13 |
| US20070129347A1 (en) | 2007-06-07 |
| ES2353390T3 (es) | 2011-03-01 |
| EP1751093B1 (de) | 2010-10-06 |
| EP1751093A1 (de) | 2007-02-14 |
| US8017630B2 (en) | 2011-09-13 |
| WO2005110976A1 (de) | 2005-11-24 |
| DE502005010342D1 (en) | 2010-11-18 |
| CA2563017A1 (en) | 2005-11-24 |
| JP4852536B2 (ja) | 2012-01-11 |
| CY1111327T1 (el) | 2015-08-05 |
| DK1751093T3 (da) | 2010-12-20 |
| SI1751093T1 (sl) | 2011-01-31 |
| ATE483679T1 (de) | 2010-10-15 |
| CA2563017C (en) | 2012-10-02 |
| PL1751093T3 (pl) | 2011-04-29 |
| DE102004023507A1 (de) | 2005-12-01 |
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