JP2006504761A - Mch拮抗活性を有する新規アミド化合物及びこれらの化合物を含む薬物 - Google Patents
Mch拮抗活性を有する新規アミド化合物及びこれらの化合物を含む薬物 Download PDFInfo
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- JP2006504761A JP2006504761A JP2004547576A JP2004547576A JP2006504761A JP 2006504761 A JP2006504761 A JP 2006504761A JP 2004547576 A JP2004547576 A JP 2004547576A JP 2004547576 A JP2004547576 A JP 2004547576A JP 2006504761 A JP2006504761 A JP 2006504761A
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- Prior art keywords
- alkyl
- chloro
- phenyl
- group
- phenoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- -1 amide compounds Chemical class 0.000 title claims abstract description 266
- 239000003814 drug Substances 0.000 title claims abstract description 7
- 150000001875 compounds Chemical class 0.000 title claims description 81
- 230000003042 antagnostic effect Effects 0.000 title claims description 5
- 229940079593 drug Drugs 0.000 title abstract description 4
- 208000008589 Obesity Diseases 0.000 claims abstract description 40
- 235000020824 obesity Nutrition 0.000 claims abstract description 40
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 29
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 16
- 206010006550 Bulimia nervosa Diseases 0.000 claims abstract description 9
- 235000005911 diet Nutrition 0.000 claims abstract description 8
- 229910052721 tungsten Inorganic materials 0.000 claims abstract description 8
- 108010047068 Melanin-concentrating hormone receptor Proteins 0.000 claims abstract description 7
- 208000032841 Bulimia Diseases 0.000 claims abstract description 6
- 230000000378 dietary effect Effects 0.000 claims abstract description 6
- 208000030159 metabolic disease Diseases 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims abstract description 4
- 208000000103 Anorexia Nervosa Diseases 0.000 claims abstract description 3
- 102000006953 melanin-concentrating hormone receptor activity proteins Human genes 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 148
- 125000004432 carbon atom Chemical group C* 0.000 claims description 122
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 73
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 53
- 150000003839 salts Chemical class 0.000 claims description 52
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 51
- 239000013543 active substance Substances 0.000 claims description 48
- 125000000623 heterocyclic group Chemical group 0.000 claims description 48
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 47
- 229920006395 saturated elastomer Polymers 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 41
- KZOWNALBTMILAP-JBMRGDGGSA-N ancitabine hydrochloride Chemical compound Cl.N=C1C=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3OC2=N1 KZOWNALBTMILAP-JBMRGDGGSA-N 0.000 claims description 39
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 37
- 125000001424 substituent group Chemical group 0.000 claims description 35
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 29
- 125000004122 cyclic group Chemical group 0.000 claims description 29
- 229910052794 bromium Inorganic materials 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 125000004076 pyridyl group Chemical group 0.000 claims description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
- 229910052731 fluorine Inorganic materials 0.000 claims description 23
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 239000005557 antagonist Substances 0.000 claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 20
- 230000002265 prevention Effects 0.000 claims description 18
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000002837 carbocyclic group Chemical group 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 14
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 14
- 208000035475 disorder Diseases 0.000 claims description 14
- 125000004434 sulfur atom Chemical group 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 12
- 206010003246 arthritis Diseases 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 11
- 241000124008 Mammalia Species 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 206010020772 Hypertension Diseases 0.000 claims description 8
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 8
- 230000037396 body weight Effects 0.000 claims description 8
- 239000000969 carrier Substances 0.000 claims description 8
- 235000021061 dietary behavior Nutrition 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- 235000006694 eating habits Nutrition 0.000 claims description 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 7
- SCVALDNCXDIEKJ-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethyl)phenoxy]-n-[4-[2-(diethylamino)ethoxy]-3-nitrophenyl]acetamide Chemical compound C1=C([N+]([O-])=O)C(OCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl SCVALDNCXDIEKJ-UHFFFAOYSA-N 0.000 claims description 7
- 208000019901 Anxiety disease Diseases 0.000 claims description 7
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 7
- 208000002249 Diabetes Complications Diseases 0.000 claims description 7
- 206010012655 Diabetic complications Diseases 0.000 claims description 7
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 7
- 230000036506 anxiety Effects 0.000 claims description 7
- RXFGWKWURLWMMY-UHFFFAOYSA-N n-[4-[2-[2-(aminomethyl)pyrrolidin-1-yl]ethoxy]-3-chlorophenyl]-2-[2-chloro-4-(trifluoromethyl)phenoxy]acetamide Chemical compound NCC1CCCN1CCOC(C(=C1)Cl)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl RXFGWKWURLWMMY-UHFFFAOYSA-N 0.000 claims description 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
- 208000027534 Emotional disease Diseases 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 208000024891 symptom Diseases 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 6
- 125000000872 2-diethylaminoethoxy group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 5
- 238000001727 in vivo Methods 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- RAANSKCNANFFCN-UHFFFAOYSA-N n-[3-chloro-4-[2-(diethylamino)ethoxy]phenyl]-2-[2-chloro-4-(trifluoromethyl)anilino]acetamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC=C1NC(=O)CNC1=CC=C(C(F)(F)F)C=C1Cl RAANSKCNANFFCN-UHFFFAOYSA-N 0.000 claims description 5
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 4
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 4
- VXQLYSVAPFBDDG-UHFFFAOYSA-N 2-[2-bromo-4-(trifluoromethyl)anilino]-n-[3-chloro-4-[2-(diethylamino)ethoxy]phenyl]acetamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC=C1NC(=O)CNC1=CC=C(C(F)(F)F)C=C1Br VXQLYSVAPFBDDG-UHFFFAOYSA-N 0.000 claims description 4
- BTJMSXLEQVWTGN-UHFFFAOYSA-N 2-[2-bromo-4-(trifluoromethyl)phenoxy]-n-[3-chloro-4-[2-(diethylamino)ethoxy]phenyl]acetamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Br BTJMSXLEQVWTGN-UHFFFAOYSA-N 0.000 claims description 4
- HHBBGDQCDSTUKT-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethyl)phenoxy]-n-[4-[2-(diethylamino)ethoxy]-3-methoxyphenyl]acetamide Chemical compound C1=C(OC)C(OCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl HHBBGDQCDSTUKT-UHFFFAOYSA-N 0.000 claims description 4
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 206010046543 Urinary incontinence Diseases 0.000 claims description 4
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 4
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 4
- BDEDBRLXJDUMGQ-UHFFFAOYSA-N ethyl 1-[2-[2-chloro-4-[[2-[2-chloro-4-(trifluoromethyl)phenoxy]acetyl]amino]phenoxy]ethyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CCOC(C(=C1)Cl)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl BDEDBRLXJDUMGQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 239000008103 glucose Substances 0.000 claims description 4
- IOBQPWNCSJWLPO-UHFFFAOYSA-N methyl 2-[2-[2-chloro-4-[[2-(2,4-dichlorophenoxy)acetyl]amino]phenoxy]ethylamino]acetate Chemical compound C1=C(Cl)C(OCCNCC(=O)OC)=CC=C1NC(=O)COC1=CC=C(Cl)C=C1Cl IOBQPWNCSJWLPO-UHFFFAOYSA-N 0.000 claims description 4
- LRWBIWQGWKPNGB-UHFFFAOYSA-N methyl 3-chloro-4-[2-[3-chloro-4-[2-(diethylamino)ethoxy]anilino]-2-oxoethoxy]benzoate Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(C(=O)OC)C=C1Cl LRWBIWQGWKPNGB-UHFFFAOYSA-N 0.000 claims description 4
- 230000027939 micturition Effects 0.000 claims description 4
- ATYHHUURZAANIN-UHFFFAOYSA-N n-[3-bromo-4-[2-(diethylamino)ethoxy]phenyl]-2-[2-chloro-4-(trifluoromethyl)phenoxy]acetamide Chemical compound C1=C(Br)C(OCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl ATYHHUURZAANIN-UHFFFAOYSA-N 0.000 claims description 4
- UBKSBCAKGNYPNZ-UHFFFAOYSA-N n-[3-chloro-4-[2-(2,5-dihydropyrrol-1-yl)ethoxy]phenyl]-2-[2-chloro-4-(trifluoromethyl)phenoxy]acetamide Chemical compound ClC1=CC(C(F)(F)F)=CC=C1OCC(=O)NC(C=C1Cl)=CC=C1OCCN1CC=CC1 UBKSBCAKGNYPNZ-UHFFFAOYSA-N 0.000 claims description 4
- HMXMRCCTPBHQMI-UHFFFAOYSA-N n-[3-chloro-4-[2-(4-hydroxypiperidin-1-yl)ethoxy]phenyl]-2-[2-chloro-4-(trifluoromethyl)phenoxy]acetamide Chemical compound C1CC(O)CCN1CCOC(C(=C1)Cl)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl HMXMRCCTPBHQMI-UHFFFAOYSA-N 0.000 claims description 4
- LAYSOXLTSYGETP-UHFFFAOYSA-N n-[3-chloro-4-[2-(4-methoxypiperidin-1-yl)ethoxy]phenyl]-2-[2-chloro-4-(trifluoromethyl)phenoxy]acetamide Chemical compound C1CC(OC)CCN1CCOC(C(=C1)Cl)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl LAYSOXLTSYGETP-UHFFFAOYSA-N 0.000 claims description 4
- KMWJKDHUGHCNHE-UHFFFAOYSA-N n-[3-chloro-4-[2-(diethylamino)ethoxy]phenyl]-2-(2-chloro-4-phenylphenoxy)acetamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(C=2C=CC=CC=2)C=C1Cl KMWJKDHUGHCNHE-UHFFFAOYSA-N 0.000 claims description 4
- RIIGCGDJQKRDTH-UHFFFAOYSA-N n-[3-chloro-4-[2-(diethylamino)ethoxy]phenyl]-2-(2-chloro-4-pyridin-3-ylphenoxy)acetamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(C=2C=NC=CC=2)C=C1Cl RIIGCGDJQKRDTH-UHFFFAOYSA-N 0.000 claims description 4
- PQFMDVQWZHNLML-UHFFFAOYSA-N n-[3-chloro-4-[2-(diethylamino)ethoxy]phenyl]-2-(2-chloro-4-thiophen-2-ylphenoxy)acetamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(C=2SC=CC=2)C=C1Cl PQFMDVQWZHNLML-UHFFFAOYSA-N 0.000 claims description 4
- HHRDCQGNZWONJB-UHFFFAOYSA-N n-[3-chloro-4-[2-(diethylamino)ethoxy]phenyl]-2-[2-chloro-4-(dimethylamino)phenoxy]acetamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(N(C)C)C=C1Cl HHRDCQGNZWONJB-UHFFFAOYSA-N 0.000 claims description 4
- WLJMQMWDYHQSJE-UHFFFAOYSA-N n-[3-chloro-4-[2-(diethylamino)ethoxy]phenyl]-2-[2-chloro-4-(furan-2-yl)phenoxy]acetamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(C=2OC=CC=2)C=C1Cl WLJMQMWDYHQSJE-UHFFFAOYSA-N 0.000 claims description 4
- GEIZFQMGLCAAIY-UHFFFAOYSA-N n-[3-chloro-4-[2-(diethylamino)ethoxy]phenyl]-2-[2-chloro-4-(trifluoromethoxy)anilino]acetamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC=C1NC(=O)CNC1=CC=C(OC(F)(F)F)C=C1Cl GEIZFQMGLCAAIY-UHFFFAOYSA-N 0.000 claims description 4
- SLALFTXZLOYTLD-UHFFFAOYSA-N n-[3-chloro-4-[2-(diethylamino)ethoxy]phenyl]-2-[2-fluoro-4-(trifluoromethyl)anilino]acetamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC=C1NC(=O)CNC1=CC=C(C(F)(F)F)C=C1F SLALFTXZLOYTLD-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 3
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 3
- LXXGDFSCDHOXTK-YRNVUSSQSA-N (e)-3-[2-chloro-4-(trifluoromethyl)phenyl]-n-[4-[2-(diethylamino)ethoxy]-3-methoxyphenyl]prop-2-enamide Chemical compound C1=C(OC)C(OCCN(CC)CC)=CC=C1NC(=O)\C=C\C1=CC=C(C(F)(F)F)C=C1Cl LXXGDFSCDHOXTK-YRNVUSSQSA-N 0.000 claims description 3
- BOBOYPLMAFCQBF-YRNVUSSQSA-N (e)-3-[2-chloro-4-(trifluoromethyl)phenyl]-n-[4-[2-(diethylamino)ethoxy]-3-methylphenyl]prop-2-enamide Chemical compound C1=C(C)C(OCCN(CC)CC)=CC=C1NC(=O)\C=C\C1=CC=C(C(F)(F)F)C=C1Cl BOBOYPLMAFCQBF-YRNVUSSQSA-N 0.000 claims description 3
- HSFWTAVXXXJJRW-CAOOACKPSA-N (e)-3-[4-(4-chlorophenyl)phenyl]-n-[4-(piperidin-1-ylmethyl)phenyl]prop-2-enamide Chemical compound C1=CC(Cl)=CC=C1C(C=C1)=CC=C1\C=C\C(=O)NC(C=C1)=CC=C1CN1CCCCC1 HSFWTAVXXXJJRW-CAOOACKPSA-N 0.000 claims description 3
- LTBKLMGTYLNGEO-FRKPEAEDSA-N (e)-3-[4-(4-chlorophenyl)phenyl]-n-[4-[(dimethylamino)methyl]phenyl]prop-2-enamide Chemical compound C1=CC(CN(C)C)=CC=C1NC(=O)\C=C\C1=CC=C(C=2C=CC(Cl)=CC=2)C=C1 LTBKLMGTYLNGEO-FRKPEAEDSA-N 0.000 claims description 3
- VTAXNULCRKKEDX-CCEZHUSRSA-N (e)-3-[5-(4-chlorophenyl)pyridin-2-yl]-n-[4-(piperidin-1-ylmethyl)phenyl]prop-2-enamide Chemical compound C1=CC(Cl)=CC=C1C(C=N1)=CC=C1\C=C\C(=O)NC(C=C1)=CC=C1CN1CCCCC1 VTAXNULCRKKEDX-CCEZHUSRSA-N 0.000 claims description 3
- ACGPJODPKALIRX-QPJJXVBHSA-N (e)-n-[3-chloro-4-[(4-methylpiperidin-1-yl)methyl]phenyl]-3-[2-chloro-4-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C1CC(C)CCN1CC(C(=C1)Cl)=CC=C1NC(=O)\C=C\C1=CC=C(C(F)(F)F)C=C1Cl ACGPJODPKALIRX-QPJJXVBHSA-N 0.000 claims description 3
- RLBWYNLTZOZBEZ-XVNBXDOJSA-N (e)-n-[3-chloro-4-[2-(4-methylpiperidin-1-yl)ethylamino]phenyl]-3-[2-chloro-4-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C1CC(C)CCN1CCNC(C(=C1)Cl)=CC=C1NC(=O)\C=C\C1=CC=C(C(F)(F)F)C=C1Cl RLBWYNLTZOZBEZ-XVNBXDOJSA-N 0.000 claims description 3
- HPDPRXFYVHSBIA-UXBLZVDNSA-N (e)-n-[3-chloro-4-[2-(diethylamino)ethoxy]phenyl]-3-[2-chloro-4-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC=C1NC(=O)\C=C\C1=CC=C(C(F)(F)F)C=C1Cl HPDPRXFYVHSBIA-UXBLZVDNSA-N 0.000 claims description 3
- YSBBQHOKZFDFGX-JXMROGBWSA-N (e)-n-[3-chloro-4-[2-(diethylamino)ethyl]phenyl]-3-[2-chloro-4-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C1=C(Cl)C(CCN(CC)CC)=CC=C1NC(=O)\C=C\C1=CC=C(C(F)(F)F)C=C1Cl YSBBQHOKZFDFGX-JXMROGBWSA-N 0.000 claims description 3
- PJDCIHCGYUJKSF-UHFFFAOYSA-N 2-(4-bromo-2-chlorophenoxy)-n-[3-chloro-4-[2-(diethylamino)ethoxy]phenyl]acetamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(Br)C=C1Cl PJDCIHCGYUJKSF-UHFFFAOYSA-N 0.000 claims description 3
- DKDPMFNYEYCHCF-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethyl)phenoxy]-n-[1-[2-(diethylamino)ethyl]-2,3-dihydroindol-5-yl]acetamide Chemical compound C=1C=C2N(CCN(CC)CC)CCC2=CC=1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl DKDPMFNYEYCHCF-UHFFFAOYSA-N 0.000 claims description 3
- GDYJRANUILXMQY-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethyl)phenoxy]-n-[1-[2-(diethylamino)ethyl]-2,3-dimethylindol-5-yl]acetamide Chemical compound C=1C=C2N(CCN(CC)CC)C(C)=C(C)C2=CC=1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl GDYJRANUILXMQY-UHFFFAOYSA-N 0.000 claims description 3
- YPXJIFIAUVZBOG-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethyl)phenoxy]-n-[1-[2-(diethylamino)ethyl]indol-5-yl]acetamide Chemical compound C=1C=C2N(CCN(CC)CC)C=CC2=CC=1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl YPXJIFIAUVZBOG-UHFFFAOYSA-N 0.000 claims description 3
- MXVJKCIETLWYRP-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethyl)phenoxy]-n-[3-cyano-4-[2-(diethylamino)ethoxy]phenyl]acetamide Chemical compound C1=C(C#N)C(OCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl MXVJKCIETLWYRP-UHFFFAOYSA-N 0.000 claims description 3
- ZTASNXVCHJIZNN-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethyl)phenoxy]-n-[4-[2-(diethylamino)ethoxy]-3-methylphenyl]acetamide Chemical compound C1=C(C)C(OCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl ZTASNXVCHJIZNN-UHFFFAOYSA-N 0.000 claims description 3
- JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 206010002650 Anorexia nervosa and bulimia Diseases 0.000 claims description 3
- 206010006895 Cachexia Diseases 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 206010007882 Cellulitis Diseases 0.000 claims description 3
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims description 3
- 206010012289 Dementia Diseases 0.000 claims description 3
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 3
- 208000008967 Enuresis Diseases 0.000 claims description 3
- 206010019280 Heart failures Diseases 0.000 claims description 3
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Classifications
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
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| PCT/EP2003/011933 WO2004039764A1 (de) | 2002-10-31 | 2003-10-28 | Neue amid-verbindungen mit mch-antagonistischer wirkung und diese verbindungen enthaltende arzneimittel |
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| JP2006504761A true JP2006504761A (ja) | 2006-02-09 |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013530237A (ja) * | 2010-07-07 | 2013-07-25 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Rhoキナーゼインヒビター |
| JP2016124812A (ja) * | 2014-12-26 | 2016-07-11 | 株式会社ヤクルト本社 | Znf143阻害活性を有する化合物およびその利用 |
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| EP1100495A4 (en) * | 1998-07-28 | 2002-09-25 | Smithkline Beecham Corp | PROPENAMIDES AS CCR5 MODULATORS |
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| AU783403B2 (en) * | 2000-07-05 | 2005-10-20 | H. Lundbeck A/S | Selective melanin concentrating hormone-1 (MCH1) receptor antagonists and uses thereof |
| US20030022891A1 (en) * | 2000-12-01 | 2003-01-30 | Anandan Palani | MCH antagonists and their use in the treatment of obesity |
| KR20040047935A (ko) * | 2001-10-25 | 2004-06-05 | 쉐링 코포레이션 | 비만 치료용 mch 길항제 |
-
2002
- 2002-10-31 DE DE10250743A patent/DE10250743A1/de not_active Withdrawn
-
2003
- 2003-10-28 DE DE50311640T patent/DE50311640D1/de not_active Expired - Lifetime
- 2003-10-28 AT AT03778292T patent/ATE434601T1/de active
- 2003-10-28 AU AU2003285306A patent/AU2003285306A1/en not_active Abandoned
- 2003-10-28 EP EP03778292A patent/EP1558567B1/de not_active Expired - Lifetime
- 2003-10-28 WO PCT/EP2003/011933 patent/WO2004039764A1/de not_active Ceased
- 2003-10-28 MX MXPA05002865A patent/MXPA05002865A/es not_active Application Discontinuation
- 2003-10-28 CN CNA2003801022366A patent/CN1708476A/zh active Pending
- 2003-10-28 BR BR0315797-0A patent/BR0315797A/pt not_active IP Right Cessation
- 2003-10-28 JP JP2004547576A patent/JP2006504761A/ja active Pending
- 2003-10-28 HR HR20050383A patent/HRP20050383A2/xx not_active Application Discontinuation
- 2003-10-28 RS YUP-2005/0330A patent/RS20050330A/sr unknown
- 2003-10-28 ES ES03778292T patent/ES2327329T3/es not_active Expired - Lifetime
- 2003-10-28 CA CA2504207A patent/CA2504207C/en not_active Expired - Lifetime
- 2003-10-28 EA EA200500596A patent/EA009040B1/ru not_active IP Right Cessation
- 2003-10-28 KR KR1020057007663A patent/KR20050065654A/ko not_active Withdrawn
- 2003-10-28 PL PL03376256A patent/PL376256A1/xx not_active Application Discontinuation
- 2003-10-29 UY UY28051A patent/UY28051A1/es not_active Application Discontinuation
- 2003-10-29 PE PE2003001094A patent/PE20040785A1/es not_active Application Discontinuation
- 2003-10-30 TW TW092130313A patent/TW200412936A/zh unknown
- 2003-10-31 AR ARP030103995A patent/AR041735A1/es unknown
-
2005
- 2005-02-09 ZA ZA200501164A patent/ZA200501164B/en unknown
- 2005-02-11 NO NO20050745A patent/NO20050745L/no not_active Application Discontinuation
- 2005-04-27 EC EC2005005765A patent/ECSP055765A/es unknown
- 2005-05-26 CO CO05051560A patent/CO5570698A2/es not_active Application Discontinuation
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| JP2013530237A (ja) * | 2010-07-07 | 2013-07-25 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Rhoキナーゼインヒビター |
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| US11787771B2 (en) | 2011-07-29 | 2023-10-17 | Karyopharm Therapeutics Inc. | Hydrazide containing nuclear transport modulators and uses thereof |
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| JP2018083832A (ja) * | 2011-07-29 | 2018-05-31 | カリオファーム セラピューティクス,インコーポレイテッド | 核内輸送調節因子およびその使用 |
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| US10544108B2 (en) | 2011-07-29 | 2020-01-28 | Karyopharm Therapeutics Inc. | Hydrazide containing nuclear transport modulators and uses thereof |
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| JP2016523902A (ja) * | 2013-06-27 | 2016-08-12 | エルジー・ライフ・サイエンシーズ・リミテッドLG Life Sciences Ltd. | Gpr120アゴニストとしてのビアリール誘導体 |
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| US12371420B2 (en) | 2014-08-15 | 2025-07-29 | Karyopharm Therapeutics Inc. | Polymorphs of Selinexor |
| US11261186B2 (en) | 2014-12-24 | 2022-03-01 | Lg Chem. Ltd. | Biaryl derivative as GPR120 agonist |
| JP2018501269A (ja) * | 2014-12-24 | 2018-01-18 | エルジー・ケム・リミテッド | Gpr120アゴニストとしてのビアリール誘導体 |
| JP2016124812A (ja) * | 2014-12-26 | 2016-07-11 | 株式会社ヤクルト本社 | Znf143阻害活性を有する化合物およびその利用 |
| US10709706B2 (en) | 2015-12-31 | 2020-07-14 | Karopharm Therapeutics Inc. | Nuclear transport modulators and uses thereof |
| US10526295B2 (en) | 2015-12-31 | 2020-01-07 | Karyopharm Therapeutics Inc. | Nuclear transport modulators and uses thereof |
| US11602530B2 (en) | 2016-11-28 | 2023-03-14 | Biogen Ma Inc. | CRM1 inhibitors for treating epilepsy |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1558567A1 (de) | 2005-08-03 |
| DE50311640D1 (de) | 2009-08-06 |
| RS20050330A (sr) | 2007-12-31 |
| PE20040785A1 (es) | 2004-12-23 |
| ATE434601T1 (de) | 2009-07-15 |
| NO20050745L (no) | 2005-05-23 |
| KR20050065654A (ko) | 2005-06-29 |
| UY28051A1 (es) | 2004-05-31 |
| ES2327329T3 (es) | 2009-10-28 |
| EP1558567B1 (de) | 2009-06-24 |
| AR041735A1 (es) | 2005-05-26 |
| DE10250743A1 (de) | 2004-05-19 |
| HRP20050383A2 (en) | 2006-08-31 |
| PL376256A1 (en) | 2005-12-27 |
| WO2004039764A1 (de) | 2004-05-13 |
| ECSP055765A (es) | 2005-07-06 |
| CA2504207C (en) | 2012-10-02 |
| CO5570698A2 (es) | 2005-10-31 |
| BR0315797A (pt) | 2005-09-13 |
| MXPA05002865A (es) | 2005-05-27 |
| CA2504207A1 (en) | 2004-05-13 |
| AU2003285306A1 (en) | 2004-05-25 |
| EA009040B1 (ru) | 2007-10-26 |
| TW200412936A (en) | 2004-08-01 |
| CN1708476A (zh) | 2005-12-14 |
| EA200500596A1 (ru) | 2005-12-29 |
| ZA200501164B (en) | 2006-10-25 |
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