JP2006504761A5 - - Google Patents
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- JP2006504761A5 JP2006504761A5 JP2004547576A JP2004547576A JP2006504761A5 JP 2006504761 A5 JP2006504761 A5 JP 2006504761A5 JP 2004547576 A JP2004547576 A JP 2004547576A JP 2004547576 A JP2004547576 A JP 2004547576A JP 2006504761 A5 JP2006504761 A5 JP 2006504761A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- alkyl
- phenyl
- acetamide
- 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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- 125000004432 carbon atoms Chemical group C* 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
- BBDAGFIXKZCXAH-CCXZUQQUSA-N ancitabine Chemical compound N=C1C=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3OC2=N1 BBDAGFIXKZCXAH-CCXZUQQUSA-N 0.000 claims description 3
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 claims description 2
- JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 claims description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
- 229940113083 morpholine Drugs 0.000 claims description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 2
- -1 Amide compounds Chemical class 0.000 claims 8
- 239000000460 chlorine Substances 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000011780 sodium chloride Substances 0.000 claims 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 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 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- ZSPYBAOJTLYSGL-UHFFFAOYSA-N N-[3-chloro-4-(2-piperidin-1-ylethoxy)phenyl]-2-[2-chloro-4-(trifluoromethyl)phenoxy]acetamide Chemical compound ClC1=CC(C(F)(F)F)=CC=C1OCC(=O)NC(C=C1Cl)=CC=C1OCCN1CCCCC1 ZSPYBAOJTLYSGL-UHFFFAOYSA-N 0.000 claims 1
- HLAGHIZEUBGUCC-UHFFFAOYSA-N N-[3-chloro-4-(2-pyrrolidin-1-ylethoxy)phenyl]-2-[2-chloro-4-(trifluoromethyl)phenoxy]acetamide Chemical compound ClC1=CC(C(F)(F)F)=CC=C1OCC(=O)NC(C=C1Cl)=CC=C1OCCN1CCCC1 HLAGHIZEUBGUCC-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- OOVHFTCZKJRKMD-UHFFFAOYSA-N N-[3-chloro-4-[2-(4-methylpiperidin-1-yl)ethyl]phenyl]-2-[2-chloro-4-(trifluoromethyl)phenoxy]acetamide Chemical compound C1CC(C)CCN1CCC(C(=C1)Cl)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl OOVHFTCZKJRKMD-UHFFFAOYSA-N 0.000 claims 1
- BMQYXQARXYXQHD-UHFFFAOYSA-N N-[3-chloro-4-[2-(4-methylpiperidin-1-yl)ethylamino]phenyl]-2-[2-chloro-4-(trifluoromethyl)phenoxy]acetamide Chemical compound C1CC(C)CCN1CCNC(C(=C1)Cl)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl BMQYXQARXYXQHD-UHFFFAOYSA-N 0.000 claims 1
- NPVLPCHNSVURFU-UHFFFAOYSA-N N-[3-chloro-4-[2-(diethylamino)ethoxy]phenyl]-2-(2,4-dibromophenoxy)acetamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(Br)C=C1Br NPVLPCHNSVURFU-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- RAFLGWWMXWKLFG-UHFFFAOYSA-N N-[3-chloro-4-[2-(diethylamino)ethoxy]phenyl]-2-(4-iodo-2-methylphenoxy)acetamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(I)C=C1C RAFLGWWMXWKLFG-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- NYEAHGKQVLRAQE-UHFFFAOYSA-N N-[3-chloro-4-[2-(diethylamino)ethoxy]phenyl]-2-[2-chloro-4-(trifluoromethyl)phenoxy]acetamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl NYEAHGKQVLRAQE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- NLTXADYJUDHDAJ-UHFFFAOYSA-N N-[3-chloro-4-[2-(diethylamino)ethyl]phenyl]-2-[2-chloro-4-(trifluoromethyl)phenoxy]acetamide Chemical compound C1=C(Cl)C(CCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl NLTXADYJUDHDAJ-UHFFFAOYSA-N 0.000 claims 1
- CGDJONPRONXADL-UHFFFAOYSA-N N-[3-chloro-4-[2-(diethylamino)ethylamino]phenyl]-2-[2-chloro-4-(trifluoromethyl)phenoxy]acetamide Chemical compound C1=C(Cl)C(NCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl CGDJONPRONXADL-UHFFFAOYSA-N 0.000 claims 1
- CSHAMIZTJNXCCR-UHFFFAOYSA-N N-[3-chloro-4-[2-[2-[(dimethylamino)methyl]pyrrolidin-1-yl]ethoxy]phenyl]-2-[2-chloro-4-(trifluoromethyl)phenoxy]acetamide Chemical compound CN(C)CC1CCCN1CCOC(C(=C1)Cl)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl CSHAMIZTJNXCCR-UHFFFAOYSA-N 0.000 claims 1
- RUKMPGMMXXQHBB-UHFFFAOYSA-N N-[3-chloro-4-[2-[ethyl(methyl)amino]ethoxy]phenyl]-2-[2-chloro-4-(trifluoromethyl)phenoxy]acetamide Chemical compound C1=C(Cl)C(OCCN(C)CC)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl RUKMPGMMXXQHBB-UHFFFAOYSA-N 0.000 claims 1
- BEYUTTNCDHJAEL-UHFFFAOYSA-N N-[3-chloro-4-[2-[ethyl(propyl)amino]ethoxy]phenyl]-2-[2-chloro-4-(trifluoromethyl)phenoxy]acetamide Chemical compound C1=C(Cl)C(OCCN(CC)CCC)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl BEYUTTNCDHJAEL-UHFFFAOYSA-N 0.000 claims 1
- ATTBOTCOIGPWCI-UHFFFAOYSA-N N-[3-chloro-4-[3-(diethylamino)propoxy]phenyl]-2-[2-chloro-4-(trifluoromethyl)phenoxy]acetamide Chemical compound C1=C(Cl)C(OCCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl ATTBOTCOIGPWCI-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 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 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000000879 imine group Chemical group 0.000 claims 1
- 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 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 150000004885 piperazines Chemical class 0.000 claims 1
- 0 B*NC(N(*)***NC)=O Chemical compound B*NC(N(*)***NC)=O 0.000 description 7
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-Piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N Imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 description 1
- YHCUZRJTNSWYCY-UHFFFAOYSA-N 2,3,4,7-tetrahydro-1H-azepine Chemical compound C1CNCC=CC1 YHCUZRJTNSWYCY-UHFFFAOYSA-N 0.000 description 1
- SMOHMDMTVAYPAI-UHFFFAOYSA-N 2,3,6,7-tetrahydro-1H-azepine Chemical compound C1CC=CCCN1 SMOHMDMTVAYPAI-UHFFFAOYSA-N 0.000 description 1
- XWWYZFUBBJHKSP-UHFFFAOYSA-N 2,3-dihydro-1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)NCNC2=C1 XWWYZFUBBJHKSP-UHFFFAOYSA-N 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N Azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N Azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N Thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 150000002466 imines Chemical group 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10250743A DE10250743A1 (de) | 2002-10-31 | 2002-10-31 | Neue Amid-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
| PCT/EP2003/011933 WO2004039764A1 (de) | 2002-10-31 | 2003-10-28 | Neue amid-verbindungen mit mch-antagonistischer wirkung und diese verbindungen enthaltende arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006504761A JP2006504761A (ja) | 2006-02-09 |
| JP2006504761A5 true JP2006504761A5 (US07132539-20061107-C00040.png) | 2009-10-08 |
Family
ID=32115015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004547576A Pending JP2006504761A (ja) | 2002-10-31 | 2003-10-28 | 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 |
Country Status (24)
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7592373B2 (en) | 2003-12-23 | 2009-09-22 | Boehringer Ingelheim International Gmbh | Amide compounds with MCH antagonistic activity and medicaments comprising these compounds |
| FR2866880A1 (fr) * | 2004-02-27 | 2005-09-02 | Oreal | Para-phenylenediamine secondaire n-alkylaminee ortho-et/ou meta-substituee, composition de teinture des fibres keratiniques contenant une telle para-phenylenediamine, procedes mettant en oeuvre cette composition et utilisations |
| US7605176B2 (en) | 2004-03-06 | 2009-10-20 | Boehringer Ingelheim International Gmbh | β-ketoamide compounds with MCH antagonistic activity |
| JP2006076990A (ja) * | 2004-03-12 | 2006-03-23 | Bayer Cropscience Ag | 殺虫性ベンゼンジカルボキサミド類 |
| US7524862B2 (en) | 2004-04-14 | 2009-04-28 | Boehringer Ingelheim International Gmbh | Alkyne compounds with MCH antagonistic activity and medicaments comprising these compounds |
| DE102004017934A1 (de) | 2004-04-14 | 2005-11-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Alkin-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
| EP2069327B1 (en) | 2006-08-25 | 2013-10-16 | Boehringer Ingelheim International GmbH | New pyridone derivatives with mch antagonistic activity and medicaments comprising these compounds |
| WO2008069611A1 (en) * | 2006-12-08 | 2008-06-12 | Korea Research Institute Of Chemical Technology | N-phenylamide derivative, process for the preparation thereof, and composition for preventing or treating ischemic diseases comprising same |
| WO2008071646A1 (en) | 2006-12-11 | 2008-06-19 | Boehringer Ingelheim International Gmbh | New pyridazine derivatives with mch antagonistic activity and medicaments comprising these compounds |
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| GEP20237477B (en) | 2012-05-09 | 2023-03-27 | Biogen Ma Inc Us | Nuclear transport modulators and uses thereof |
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| WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| ES2926377T3 (es) | 2014-08-15 | 2022-10-25 | Karyopharm Therapeutics Inc | Polimorfos de selinexor |
| CN105439914B (zh) * | 2014-09-17 | 2017-07-11 | 复旦大学 | 4‑氨酰基苯氧乙酰胺类化合物及其药物用途 |
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| JP6533997B2 (ja) * | 2014-12-26 | 2019-06-26 | 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 |
| WO2001021577A2 (en) * | 1999-09-20 | 2001-03-29 | Takeda Chemical Industries, Ltd. | Melanin concentrating hormone antagonist |
| CA2384041A1 (en) * | 2000-07-05 | 2002-01-24 | Synaptic Pharmaceuticals Corporation | 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 |
| MXPA04003858A (es) * | 2001-10-25 | 2004-07-08 | Schering Corp | Antagonistas de mch para el tratamiento de obesidad. |
-
2002
- 2002-10-31 DE DE10250743A patent/DE10250743A1/de not_active Withdrawn
-
2003
- 2003-10-28 AU AU2003285306A patent/AU2003285306A1/en not_active Abandoned
- 2003-10-28 WO PCT/EP2003/011933 patent/WO2004039764A1/de active Application Filing
- 2003-10-28 MX MXPA05002865A patent/MXPA05002865A/es not_active Application Discontinuation
- 2003-10-28 CA CA2504207A patent/CA2504207C/en not_active Expired - Lifetime
- 2003-10-28 AT AT03778292T patent/ATE434601T1/de active
- 2003-10-28 EA EA200500596A patent/EA009040B1/ru not_active IP Right Cessation
- 2003-10-28 JP JP2004547576A patent/JP2006504761A/ja active Pending
- 2003-10-28 EP EP03778292A patent/EP1558567B1/de not_active Expired - Lifetime
- 2003-10-28 ES ES03778292T patent/ES2327329T3/es not_active Expired - Lifetime
- 2003-10-28 DE DE50311640T patent/DE50311640D1/de not_active Expired - Lifetime
- 2003-10-28 KR KR1020057007663A patent/KR20050065654A/ko not_active Application Discontinuation
- 2003-10-28 RS YUP-2005/0330A patent/RS20050330A/sr unknown
- 2003-10-28 PL PL03376256A patent/PL376256A1/xx 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 Expired - Fee Related
- 2003-10-29 PE PE2003001094A patent/PE20040785A1/es not_active Application Discontinuation
- 2003-10-29 UY UY28051A patent/UY28051A1/es not_active Application Discontinuation
- 2003-10-30 TW TW092130313A patent/TW200412936A/zh unknown
- 2003-10-31 AR ARP030103995A patent/AR041735A1/es not_active Suspension/Interruption
-
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
- 2005-04-29 HR HR20050383A patent/HRP20050383A2/xx not_active Application Discontinuation
- 2005-05-26 CO CO05051560A patent/CO5570698A2/es not_active Application Discontinuation
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