JP2005535650A5 - - Google Patents
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- JP2005535650A5 JP2005535650A5 JP2004518696A JP2004518696A JP2005535650A5 JP 2005535650 A5 JP2005535650 A5 JP 2005535650A5 JP 2004518696 A JP2004518696 A JP 2004518696A JP 2004518696 A JP2004518696 A JP 2004518696A JP 2005535650 A5 JP2005535650 A5 JP 2005535650A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- piperidinyl
- fluoro
- methylacetamide
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 12
- -1 cyano, methyl Chemical group 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical group 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- CUBGFICHXDHDKU-UHFFFAOYSA-N n-[1-(3,5-dibromophenyl)ethyl]-2-[4-(4-fluorophenyl)-1-methylpiperidin-4-yl]-n-methylacetamide Chemical compound C=1C(Br)=CC(Br)=CC=1C(C)N(C)C(=O)CC1(C=2C=CC(F)=CC=2)CCN(C)CC1 CUBGFICHXDHDKU-UHFFFAOYSA-N 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- CBCZFQUWFWZMNV-UHFFFAOYSA-N 2-[4-(3-chlorophenyl)piperidin-4-yl]-n-[1-(3,5-dibromophenyl)ethyl]-n-methylacetamide Chemical compound C=1C(Br)=CC(Br)=CC=1C(C)N(C)C(=O)CC1(C=2C=C(Cl)C=CC=2)CCNCC1 CBCZFQUWFWZMNV-UHFFFAOYSA-N 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 239000011630 iodine Substances 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- VCJNUKLCJUZPER-UHFFFAOYSA-N n-[(3,5-dichlorophenyl)methyl]-2-[3-fluoro-4-(4-fluoro-2-methylphenyl)azepin-4-yl]-n-methylacetamide Chemical compound C1=CC=NC=C(F)C1(C=1C(=CC(F)=CC=1)C)CC(=O)N(C)CC1=CC(Cl)=CC(Cl)=C1 VCJNUKLCJUZPER-UHFFFAOYSA-N 0.000 claims 2
- OXGUVKBVGBHGCD-UHFFFAOYSA-N n-[1-(3,5-dibromophenyl)ethyl]-2-[4-(4-fluoro-3-methylphenyl)-1-methylpiperidin-4-yl]-n-methylacetamide Chemical compound C=1C(Br)=CC(Br)=CC=1C(C)N(C)C(=O)CC1(C=2C=C(C)C(F)=CC=2)CCN(C)CC1 OXGUVKBVGBHGCD-UHFFFAOYSA-N 0.000 claims 2
- LPGKLBRZOSQCQG-UHFFFAOYSA-N n-[1-(3,5-dibromophenyl)ethyl]-2-[4-(4-fluoro-3-methylphenyl)piperidin-4-yl]-n-methylacetamide Chemical compound C=1C(Br)=CC(Br)=CC=1C(C)N(C)C(=O)CC1(C=2C=C(C)C(F)=CC=2)CCNCC1 LPGKLBRZOSQCQG-UHFFFAOYSA-N 0.000 claims 2
- KIVIARGCODRSTP-UHFFFAOYSA-N n-[1-(3,5-dibromophenyl)ethyl]-2-[4-(4-fluorophenyl)piperidin-4-yl]-n-methylacetamide Chemical compound C=1C(Br)=CC(Br)=CC=1C(C)N(C)C(=O)CC1(C=2C=CC(F)=CC=2)CCNCC1 KIVIARGCODRSTP-UHFFFAOYSA-N 0.000 claims 2
- XGIULTTWQOPCSJ-UHFFFAOYSA-N n-[1-(3,5-dibromophenyl)ethyl]-n-methyl-2-(1-methyl-4-phenylpiperidin-4-yl)acetamide Chemical compound C=1C(Br)=CC(Br)=CC=1C(C)N(C)C(=O)CC1(C=2C=CC=CC=2)CCN(C)CC1 XGIULTTWQOPCSJ-UHFFFAOYSA-N 0.000 claims 2
- KQRTULUMOKTQES-UHFFFAOYSA-N n-[1-(3,5-dichlorophenyl)ethyl]-2-[4-(4-fluorophenyl)-1-methylpiperidin-4-yl]-n-methylacetamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1C(C)N(C)C(=O)CC1(C=2C=CC(F)=CC=2)CCN(C)CC1 KQRTULUMOKTQES-UHFFFAOYSA-N 0.000 claims 2
- ZGHMSACBXSLVOL-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-2-[4-(4-fluorophenyl)-1-methylpiperidin-4-yl]-n-methylacetamide Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(C)N(C)C(=O)CC1(C=2C=CC(F)=CC=2)CCN(C)CC1 ZGHMSACBXSLVOL-UHFFFAOYSA-N 0.000 claims 2
- KXHRKAVQKDLHBQ-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-2-[4-(4-fluorophenyl)piperidin-4-yl]-n-methylacetamide Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(C)N(C)C(=O)CC1(C=2C=CC(F)=CC=2)CCNCC1 KXHRKAVQKDLHBQ-UHFFFAOYSA-N 0.000 claims 2
- YBMUHVZBGHSLDW-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-[3-fluoro-4-(4-fluoro-2-methylphenyl)azepin-4-yl]-n-methylacetamide Chemical compound C1=CC=NC=C(F)C1(C=1C(=CC(F)=CC=1)C)CC(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 YBMUHVZBGHSLDW-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- OYWUUEUHGOENKD-UHFFFAOYSA-N 2-[1-(cyclopropylmethyl)-4-(4-fluorophenyl)piperidin-4-yl]-n-[(3,5-dibromophenyl)methyl]-n-methylacetamide Chemical compound C1CN(CC2CC2)CCC1(C=1C=CC(F)=CC=1)CC(=O)N(C)CC1=CC(Br)=CC(Br)=C1 OYWUUEUHGOENKD-UHFFFAOYSA-N 0.000 claims 1
- PUMQASALSAPJEO-UHFFFAOYSA-N 2-[4-(3-chlorophenyl)-1-methylpiperidin-4-yl]-n-[1-(3,5-dibromophenyl)ethyl]-n-methylacetamide Chemical compound C=1C(Br)=CC(Br)=CC=1C(C)N(C)C(=O)CC1(C=2C=C(Cl)C=CC=2)CCN(C)CC1 PUMQASALSAPJEO-UHFFFAOYSA-N 0.000 claims 1
- QSEXPEXXHIAOFV-UHFFFAOYSA-N 2-[4-(3-chlorophenyl)-1-methylpiperidin-4-yl]-n-[1-(3,5-dichlorophenyl)ethyl]-n-methylacetamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1C(C)N(C)C(=O)CC1(C=2C=C(Cl)C=CC=2)CCN(C)CC1 QSEXPEXXHIAOFV-UHFFFAOYSA-N 0.000 claims 1
- OEEFNSQUTAISGV-UHFFFAOYSA-N 2-[4-(3-chlorophenyl)piperidin-4-yl]-n-[(3,5-dibromophenyl)methyl]-n-methylacetamide Chemical compound C1CNCCC1(C=1C=C(Cl)C=CC=1)CC(=O)N(C)CC1=CC(Br)=CC(Br)=C1 OEEFNSQUTAISGV-UHFFFAOYSA-N 0.000 claims 1
- PYDSTENQHKZPJA-UHFFFAOYSA-N 2-[4-(3-chlorophenyl)piperidin-4-yl]-n-[1-(3,5-dichlorophenyl)ethyl]-n-methylacetamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1C(C)N(C)C(=O)CC1(C=2C=C(Cl)C=CC=2)CCNCC1 PYDSTENQHKZPJA-UHFFFAOYSA-N 0.000 claims 1
- PZVMFKKTUMOFEO-UHFFFAOYSA-N 2-[4-(4-cyanophenyl)piperidin-4-yl]-n-[1-(3,5-dibromophenyl)ethyl]-n-methylacetamide Chemical compound C=1C(Br)=CC(Br)=CC=1C(C)N(C)C(=O)CC1(C=2C=CC(=CC=2)C#N)CCNCC1 PZVMFKKTUMOFEO-UHFFFAOYSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical group N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 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 1
- 108010078791 Carrier Proteins Proteins 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 102100024304 Protachykinin-1 Human genes 0.000 claims 1
- 101800003906 Substance P Proteins 0.000 claims 1
- 102000003141 Tachykinin Human genes 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 claims 1
- KBGITZDEJWREGG-UHFFFAOYSA-N n-[(3,5-dibromophenyl)methyl]-2-[1-ethyl-4-(4-fluorophenyl)piperidin-4-yl]-n-methylacetamide Chemical compound C1CN(CC)CCC1(C=1C=CC(F)=CC=1)CC(=O)N(C)CC1=CC(Br)=CC(Br)=C1 KBGITZDEJWREGG-UHFFFAOYSA-N 0.000 claims 1
- FTLVICBKHBUZKS-UHFFFAOYSA-N n-[(3,5-dibromophenyl)methyl]-2-[4-(3,4-difluorophenyl)-1-methylpiperidin-4-yl]-n-methylacetamide Chemical compound C1CN(C)CCC1(C=1C=C(F)C(F)=CC=1)CC(=O)N(C)CC1=CC(Br)=CC(Br)=C1 FTLVICBKHBUZKS-UHFFFAOYSA-N 0.000 claims 1
- LABGAISISHWSFW-UHFFFAOYSA-N n-[(3,5-dibromophenyl)methyl]-2-[4-(3,4-difluorophenyl)piperidin-4-yl]-n-methylacetamide Chemical compound C1CNCCC1(C=1C=C(F)C(F)=CC=1)CC(=O)N(C)CC1=CC(Br)=CC(Br)=C1 LABGAISISHWSFW-UHFFFAOYSA-N 0.000 claims 1
- YOQJLRIIOAJDKZ-UHFFFAOYSA-N n-[(3,5-dibromophenyl)methyl]-2-[4-(3,4-dimethylphenyl)piperidin-4-yl]-n-methylacetamide Chemical compound C1CNCCC1(C=1C=C(C)C(C)=CC=1)CC(=O)N(C)CC1=CC(Br)=CC(Br)=C1 YOQJLRIIOAJDKZ-UHFFFAOYSA-N 0.000 claims 1
- TWCRITRSWQJWKA-UHFFFAOYSA-N n-[(3,5-dibromophenyl)methyl]-2-[4-(3-fluorophenyl)-1-methylpiperidin-4-yl]-n-methylacetamide Chemical compound C1CN(C)CCC1(C=1C=C(F)C=CC=1)CC(=O)N(C)CC1=CC(Br)=CC(Br)=C1 TWCRITRSWQJWKA-UHFFFAOYSA-N 0.000 claims 1
- UMAXDBLPJXAGBO-UHFFFAOYSA-N n-[(3,5-dibromophenyl)methyl]-2-[4-(3-fluorophenyl)piperidin-4-yl]-n-methylacetamide Chemical compound C1CNCCC1(C=1C=C(F)C=CC=1)CC(=O)N(C)CC1=CC(Br)=CC(Br)=C1 UMAXDBLPJXAGBO-UHFFFAOYSA-N 0.000 claims 1
- LAZGFGUCJYBTJM-UHFFFAOYSA-N n-[(3,5-dibromophenyl)methyl]-2-[4-(4-fluoro-2-methylphenyl)-1-methylpiperidin-4-yl]-n-methylacetamide Chemical compound C1CN(C)CCC1(C=1C(=CC(F)=CC=1)C)CC(=O)N(C)CC1=CC(Br)=CC(Br)=C1 LAZGFGUCJYBTJM-UHFFFAOYSA-N 0.000 claims 1
- OHBATSBWDOWIHA-UHFFFAOYSA-N n-[(3,5-dibromophenyl)methyl]-2-[4-(4-fluoro-2-methylphenyl)piperidin-4-yl]-n-methylacetamide Chemical compound C1CNCCC1(C=1C(=CC(F)=CC=1)C)CC(=O)N(C)CC1=CC(Br)=CC(Br)=C1 OHBATSBWDOWIHA-UHFFFAOYSA-N 0.000 claims 1
- KLBWSLPBLMGIMR-UHFFFAOYSA-N n-[(3,5-dibromophenyl)methyl]-2-[4-(4-fluoro-3-methylphenyl)-1-methylpiperidin-4-yl]-n-methylacetamide Chemical compound C1CN(C)CCC1(C=1C=C(C)C(F)=CC=1)CC(=O)N(C)CC1=CC(Br)=CC(Br)=C1 KLBWSLPBLMGIMR-UHFFFAOYSA-N 0.000 claims 1
- APVVVQYIXSHNFF-UHFFFAOYSA-N n-[(3,5-dibromophenyl)methyl]-2-[4-(4-fluoro-3-methylphenyl)piperidin-4-yl]-n-methylacetamide Chemical compound C1CNCCC1(C=1C=C(C)C(F)=CC=1)CC(=O)N(C)CC1=CC(Br)=CC(Br)=C1 APVVVQYIXSHNFF-UHFFFAOYSA-N 0.000 claims 1
- FPJNDGJGAPYRPL-UHFFFAOYSA-N n-[(3,5-dibromophenyl)methyl]-2-[4-(4-fluorophenyl)-1-methylazepan-4-yl]-n-methylacetamide Chemical compound C1CCN(C)CCC1(C=1C=CC(F)=CC=1)CC(=O)N(C)CC1=CC(Br)=CC(Br)=C1 FPJNDGJGAPYRPL-UHFFFAOYSA-N 0.000 claims 1
- SBIHQWGCVPZYOK-UHFFFAOYSA-N n-[(3,5-dibromophenyl)methyl]-2-[4-(4-fluorophenyl)-1-methylpiperidin-4-yl]-n-methylacetamide Chemical compound C1CN(C)CCC1(C=1C=CC(F)=CC=1)CC(=O)N(C)CC1=CC(Br)=CC(Br)=C1 SBIHQWGCVPZYOK-UHFFFAOYSA-N 0.000 claims 1
- JMGILTGHFIRXNO-UHFFFAOYSA-N n-[(3,5-dibromophenyl)methyl]-2-[4-(4-fluorophenyl)azepan-4-yl]-n-methylacetamide Chemical compound C1CCNCCC1(C=1C=CC(F)=CC=1)CC(=O)N(C)CC1=CC(Br)=CC(Br)=C1 JMGILTGHFIRXNO-UHFFFAOYSA-N 0.000 claims 1
- IEGOVDNNVDRMGV-UHFFFAOYSA-N n-[(3,5-dibromophenyl)methyl]-2-[4-(4-fluorophenyl)piperidin-4-yl]-n-methylacetamide Chemical compound C1CNCCC1(C=1C=CC(F)=CC=1)CC(=O)N(C)CC1=CC(Br)=CC(Br)=C1 IEGOVDNNVDRMGV-UHFFFAOYSA-N 0.000 claims 1
- CLKKHXPWZNLYTD-UHFFFAOYSA-N n-[(3,5-dibromophenyl)methyl]-n-methyl-2-(1-methyl-4-phenylpiperidin-4-yl)acetamide Chemical compound C1CN(C)CCC1(C=1C=CC=CC=1)CC(=O)N(C)CC1=CC(Br)=CC(Br)=C1 CLKKHXPWZNLYTD-UHFFFAOYSA-N 0.000 claims 1
- APJWCTJEVJXCJW-UHFFFAOYSA-N n-[(3,5-dibromophenyl)methyl]-n-methyl-2-(4-phenylpiperidin-4-yl)acetamide Chemical compound C1CNCCC1(C=1C=CC=CC=1)CC(=O)N(C)CC1=CC(Br)=CC(Br)=C1 APJWCTJEVJXCJW-UHFFFAOYSA-N 0.000 claims 1
- QCFKFTAAYXDMST-UHFFFAOYSA-N n-[(3,5-dichlorophenyl)methyl]-2-[3-fluoro-4-(4-fluorophenyl)piperidin-4-yl]-n-methylacetamide Chemical compound C1CNCC(F)C1(C=1C=CC(F)=CC=1)CC(=O)N(C)CC1=CC(Cl)=CC(Cl)=C1 QCFKFTAAYXDMST-UHFFFAOYSA-N 0.000 claims 1
- UGPFLVWKAQRSJW-UHFFFAOYSA-N n-[(3,5-dichlorophenyl)methyl]-2-[4-(4-fluoro-2-methylphenyl)-1-(2-methoxyethyl)piperidin-4-yl]-n-methylacetamide Chemical compound C1CN(CCOC)CCC1(C=1C(=CC(F)=CC=1)C)CC(=O)N(C)CC1=CC(Cl)=CC(Cl)=C1 UGPFLVWKAQRSJW-UHFFFAOYSA-N 0.000 claims 1
- PCIYLGYWJDFXTM-UHFFFAOYSA-N n-[(3,5-dichlorophenyl)methyl]-2-[4-(4-fluoro-2-methylphenyl)-1-methylpiperidin-4-yl]-n-methylacetamide Chemical compound C1CN(C)CCC1(C=1C(=CC(F)=CC=1)C)CC(=O)N(C)CC1=CC(Cl)=CC(Cl)=C1 PCIYLGYWJDFXTM-UHFFFAOYSA-N 0.000 claims 1
- YUBBKGKCZNBWFN-UHFFFAOYSA-N n-[(3,5-dichlorophenyl)methyl]-2-[4-(4-fluoro-2-methylphenyl)azepin-4-yl]-n-methylacetamide Chemical compound C1=CC=NC=CC1(C=1C(=CC(F)=CC=1)C)CC(=O)N(C)CC1=CC(Cl)=CC(Cl)=C1 YUBBKGKCZNBWFN-UHFFFAOYSA-N 0.000 claims 1
- UKVZBBOFTAACDW-UHFFFAOYSA-N n-[(3,5-dichlorophenyl)methyl]-2-[4-(4-fluoro-2-methylphenyl)piperidin-4-yl]-n-methylacetamide Chemical compound C1CNCCC1(C=1C(=CC(F)=CC=1)C)CC(=O)N(C)CC1=CC(Cl)=CC(Cl)=C1 UKVZBBOFTAACDW-UHFFFAOYSA-N 0.000 claims 1
- WHAURRGDIYUJKM-UHFFFAOYSA-N n-[(3,5-dichlorophenyl)methyl]-2-[4-(4-fluorophenyl)-1-methylpiperidin-4-yl]-n-methylacetamide Chemical compound C1CN(C)CCC1(C=1C=CC(F)=CC=1)CC(=O)N(C)CC1=CC(Cl)=CC(Cl)=C1 WHAURRGDIYUJKM-UHFFFAOYSA-N 0.000 claims 1
- JKGMQZIBWKUSPD-UHFFFAOYSA-N n-[(3,5-dichlorophenyl)methyl]-2-[4-(4-fluorophenyl)piperidin-4-yl]-n-methylacetamide Chemical compound C1CNCCC1(C=1C=CC(F)=CC=1)CC(=O)N(C)CC1=CC(Cl)=CC(Cl)=C1 JKGMQZIBWKUSPD-UHFFFAOYSA-N 0.000 claims 1
- WBWWXIMMLFNUJG-UHFFFAOYSA-N n-[(3,5-dichlorophenyl)methyl]-4-(4-fluorophenyl)-n-methylpiperidine-4-carboxamide Chemical compound C1CNCCC1(C=1C=CC(F)=CC=1)C(=O)N(C)CC1=CC(Cl)=CC(Cl)=C1 WBWWXIMMLFNUJG-UHFFFAOYSA-N 0.000 claims 1
- XFEFBFOPLLPADO-UHFFFAOYSA-N n-[(3-bromo-5-cyanophenyl)methyl]-2-[4-(4-fluorophenyl)-1-methylpiperidin-4-yl]-n-methylacetamide Chemical compound C1CN(C)CCC1(C=1C=CC(F)=CC=1)CC(=O)N(C)CC1=CC(Br)=CC(C#N)=C1 XFEFBFOPLLPADO-UHFFFAOYSA-N 0.000 claims 1
- ZQMQUKLVAUQUEA-UHFFFAOYSA-N n-[(3-bromo-5-cyanophenyl)methyl]-2-[4-(4-fluorophenyl)piperidin-4-yl]-n-methylacetamide Chemical compound C1CNCCC1(C=1C=CC(F)=CC=1)CC(=O)N(C)CC1=CC(Br)=CC(C#N)=C1 ZQMQUKLVAUQUEA-UHFFFAOYSA-N 0.000 claims 1
- JKMBTCHEQYHODT-UHFFFAOYSA-N n-[1-(3,5-dibromophenyl)ethyl]-2-[4-(3,4-difluorophenyl)-1-methylpiperidin-4-yl]-n-methylacetamide Chemical compound C=1C(Br)=CC(Br)=CC=1C(C)N(C)C(=O)CC1(C=2C=C(F)C(F)=CC=2)CCN(C)CC1 JKMBTCHEQYHODT-UHFFFAOYSA-N 0.000 claims 1
- SXJGDTYHOHCOCK-UHFFFAOYSA-N n-[1-(3,5-dibromophenyl)ethyl]-2-[4-(3,4-difluorophenyl)piperidin-4-yl]-n-methylacetamide Chemical compound C=1C(Br)=CC(Br)=CC=1C(C)N(C)C(=O)CC1(C=2C=C(F)C(F)=CC=2)CCNCC1 SXJGDTYHOHCOCK-UHFFFAOYSA-N 0.000 claims 1
- OLOCSAMKFGITFZ-UHFFFAOYSA-N n-[1-(3,5-dibromophenyl)ethyl]-2-[4-(3-fluorophenyl)-1-methylpiperidin-4-yl]-n-methylacetamide Chemical compound C=1C(Br)=CC(Br)=CC=1C(C)N(C)C(=O)CC1(C=2C=C(F)C=CC=2)CCN(C)CC1 OLOCSAMKFGITFZ-UHFFFAOYSA-N 0.000 claims 1
- GURNMMQXHJFSIY-UHFFFAOYSA-N n-[1-(3,5-dibromophenyl)ethyl]-2-[4-(3-fluorophenyl)piperidin-4-yl]-n-methylacetamide Chemical compound C=1C(Br)=CC(Br)=CC=1C(C)N(C)C(=O)CC1(C=2C=C(F)C=CC=2)CCNCC1 GURNMMQXHJFSIY-UHFFFAOYSA-N 0.000 claims 1
- IBFWKPCDEAEHPF-UHFFFAOYSA-N n-[1-(3,5-dibromophenyl)ethyl]-n-methyl-2-(4-phenylpiperidin-4-yl)acetamide Chemical compound C=1C(Br)=CC(Br)=CC=1C(C)N(C)C(=O)CC1(C=2C=CC=CC=2)CCNCC1 IBFWKPCDEAEHPF-UHFFFAOYSA-N 0.000 claims 1
- FNMPPDILEUAQPF-UHFFFAOYSA-N n-[1-(3,5-dichlorophenyl)ethyl]-2-[4-(4-fluoro-3-methylphenyl)piperidin-4-yl]-n-methylacetamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1C(C)N(C)C(=O)CC1(C=2C=C(C)C(F)=CC=2)CCNCC1 FNMPPDILEUAQPF-UHFFFAOYSA-N 0.000 claims 1
- GDQICJDTYOYKRA-UHFFFAOYSA-N n-[1-(3,5-dichlorophenyl)ethyl]-2-[4-(4-fluorophenyl)piperidin-4-yl]-n-methylacetamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1C(C)N(C)C(=O)CC1(C=2C=CC(F)=CC=2)CCNCC1 GDQICJDTYOYKRA-UHFFFAOYSA-N 0.000 claims 1
- ZZEDIURUGGTDOH-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-2-[4-(4-fluoro-2-methylphenyl)piperidin-4-yl]-n-methylacetamide Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(C)N(C)C(=O)CC1(C=2C(=CC(F)=CC=2)C)CCNCC1 ZZEDIURUGGTDOH-UHFFFAOYSA-N 0.000 claims 1
- VKVNFXAMDMLNKV-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-2-[4-(4-fluorophenyl)-1-methylazepan-4-yl]-n-methylacetamide Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(C)N(C)C(=O)CC1(C=2C=CC(F)=CC=2)CCCN(C)CC1 VKVNFXAMDMLNKV-UHFFFAOYSA-N 0.000 claims 1
- LEILNUMLEXGOOI-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-2-[4-(4-fluorophenyl)azepan-4-yl]-n-methylacetamide Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(C)N(C)C(=O)CC1(C=2C=CC(F)=CC=2)CCCNCC1 LEILNUMLEXGOOI-UHFFFAOYSA-N 0.000 claims 1
- PPKADJAJJQNDAR-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-methyl-2-(1-methyl-4-phenylpiperidin-4-yl)acetamide Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(C)N(C)C(=O)CC1(C=2C=CC=CC=2)CCN(C)CC1 PPKADJAJJQNDAR-UHFFFAOYSA-N 0.000 claims 1
- VZHSEYRKQIMGOP-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-methyl-2-(4-phenylpiperidin-4-yl)acetamide Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(C)N(C)C(=O)CC1(C=2C=CC=CC=2)CCNCC1 VZHSEYRKQIMGOP-UHFFFAOYSA-N 0.000 claims 1
- SUFHNAMRRNNRQH-UHFFFAOYSA-N n-[2-(3,5-dibromophenyl)propan-2-yl]-2-[4-(4-fluorophenyl)-1-methylpiperidin-4-yl]-n-methylacetamide Chemical compound C=1C(Br)=CC(Br)=CC=1C(C)(C)N(C)C(=O)CC1(C=2C=CC(F)=CC=2)CCN(C)CC1 SUFHNAMRRNNRQH-UHFFFAOYSA-N 0.000 claims 1
- ZNYREVKCPQKHSI-UHFFFAOYSA-N n-[2-(3,5-dibromophenyl)propan-2-yl]-2-[4-(4-fluorophenyl)piperidin-4-yl]-n-methylacetamide Chemical compound C=1C(Br)=CC(Br)=CC=1C(C)(C)N(C)C(=O)CC1(C=2C=CC(F)=CC=2)CCNCC1 ZNYREVKCPQKHSI-UHFFFAOYSA-N 0.000 claims 1
- QKFZHLZCWOPTOG-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-[4-(4-fluoro-2-methylphenyl)azepin-4-yl]-n-methylacetamide Chemical compound C1=CC=NC=CC1(C=1C(=CC(F)=CC=1)C)CC(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 QKFZHLZCWOPTOG-UHFFFAOYSA-N 0.000 claims 1
- VLOOJIHMDCCLTG-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-[4-(4-fluorophenyl)-1-methylpiperidin-4-yl]-n-methylacetamide Chemical compound C1CN(C)CCC1(C=1C=CC(F)=CC=1)CC(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 VLOOJIHMDCCLTG-UHFFFAOYSA-N 0.000 claims 1
- RCHLCQLYGBYPGS-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-[4-(4-fluorophenyl)azepin-4-yl]-n-methylacetamide Chemical compound C1=CC=NC=CC1(C=1C=CC(F)=CC=1)CC(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 RCHLCQLYGBYPGS-UHFFFAOYSA-N 0.000 claims 1
- OBOOJNFHRVFNLU-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(4-chlorophenyl)-n-methylpiperidine-4-carboxamide Chemical compound C1CNCCC1(C=1C=CC(Cl)=CC=1)C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 OBOOJNFHRVFNLU-UHFFFAOYSA-N 0.000 claims 1
- AXOWLGIXWDBUBL-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(4-fluorophenyl)-n-methylpiperidine-4-carboxamide Chemical compound C1CNCCC1(C=1C=CC(F)=CC=1)C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 AXOWLGIXWDBUBL-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910052757 nitrogen Chemical group 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 230000000697 serotonin reuptake Effects 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 108060008037 tachykinin Proteins 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0215393A GB0215393D0 (en) | 2002-07-03 | 2002-07-03 | Chemical compounds |
| GB0306454A GB0306454D0 (en) | 2003-03-20 | 2003-03-20 | Chemical compounds |
| PCT/EP2003/007127 WO2004005256A2 (en) | 2002-07-03 | 2003-07-02 | Substituted 4-phenyl-piperidin-amides as tachykinin antagonists and serotonin reptake inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005535650A JP2005535650A (ja) | 2005-11-24 |
| JP2005535650A5 true JP2005535650A5 (enExample) | 2006-08-10 |
Family
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| JP2004518696A Pending JP2005535650A (ja) | 2002-07-03 | 2003-07-02 | タキキニンアンタゴニストおよびセロトニン再取り込み阻害剤としての置換４−フェニル−ピペリジン−アミド |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20060128752A1 (enExample) |
| EP (1) | EP1558577B1 (enExample) |
| JP (1) | JP2005535650A (enExample) |
| AT (1) | ATE453621T1 (enExample) |
| AU (1) | AU2003257433A1 (enExample) |
| DE (1) | DE60330794D1 (enExample) |
| WO (1) | WO2004005256A2 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0310724D0 (en) * | 2003-05-09 | 2003-06-11 | Glaxo Group Ltd | Chemical compounds |
| GB0412865D0 (en) | 2004-06-09 | 2004-07-14 | Glaxo Group Ltd | Chemical compounds |
| US7276631B2 (en) | 2004-07-20 | 2007-10-02 | Bristol-Myers Squibb Company | Cyclopentylamine and cyclohexylamine derivatives as NK-1/SSRI antagonists |
| US7494986B2 (en) | 2004-07-20 | 2009-02-24 | Bristol-Myers Squibb Company | Cycloalkylamine derivatives as NK-1/SSRI antagonists |
| US7138423B2 (en) | 2004-07-20 | 2006-11-21 | Bristol-Myers Squibb Company | Arylpyrrolidine derivatives as NK-1 /SSRI antagonists |
| US7098203B2 (en) | 2004-07-20 | 2006-08-29 | Bristol-Myers Squibb Company | Homopiperidine derivatives as NK-1 antagonists |
| US7179926B2 (en) | 2004-07-26 | 2007-02-20 | Bristol-Myers Squibb Company | Aryloxyalkylamine NK-1/SSRI inhibitors |
| JP2014159375A (ja) * | 2011-06-15 | 2014-09-04 | Takeda Chem Ind Ltd | アゼパン化合物 |
| EP2729147B1 (en) | 2011-07-04 | 2017-09-06 | IRBM - Science Park S.p.A. | Nk-1 receptor antagonists for treating corneal neovascularisation |
| CN106278924B (zh) * | 2016-06-08 | 2018-08-17 | 长沙理工大学 | 一种以取代米氏酸为酰化剂水相中制备n-芳基叔酰胺的方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3087209A (en) * | 1959-07-13 | 1963-04-30 | Foremost Dairies Inc | Container sterilizing apparatus |
| NL130088C (enExample) * | 1960-03-14 | |||
| US3097029A (en) * | 1961-07-07 | 1963-07-09 | Whirlpool Co | Broiler drawer door |
| GB1356118A (en) * | 1970-12-16 | 1974-06-12 | Searle & Co | 1-3-cyano-3,3-diphenylpropyl-4-phenylpiperidine-4-carboxylic acid derivatives |
| JPH08504435A (ja) * | 1992-12-14 | 1996-05-14 | メルク シヤープ エンド ドーム リミテツド | タキキニン受容体拮抗剤としての４−アミノメチル／チオメチル／スルホニルメチル−４−フェニルピペリジン |
| MXPA00011204A (es) * | 1998-05-15 | 2003-04-22 | Aventis Pharma Inc | Derivados de carboxiamida sustituidos con carboxi, como antagonistas de receptor de taquiquinina. |
| US6423519B1 (en) * | 1998-07-15 | 2002-07-23 | Gpc Biotech Inc. | Compositions and methods for inhibiting fungal growth |
| FR2784377B3 (fr) * | 1998-10-09 | 2000-11-17 | Sanofi Sa | Nouveaux composes derives d'ureidopiperidine, antagonistes selectifs des recepteurs nk3 humains, procede pour leur obtention et compositions pharmaceutiques les contenant |
| ATE460163T1 (de) * | 2001-04-12 | 2010-03-15 | Pharmacopeia Llc | Arly und diaryl piperidinderivate verwendbar als mch-hemmer |
| NZ531679A (en) * | 2001-10-15 | 2005-02-25 | Janssen Pharmaceutica Nv | Novel substituted 4-phenyl-4-[1H-imidazol-2-YL]-piperidine derivatives and their use as selective non-peptide delta opioid agonists |
-
2003
- 2003-07-02 AT AT03762615T patent/ATE453621T1/de not_active IP Right Cessation
- 2003-07-02 WO PCT/EP2003/007127 patent/WO2004005256A2/en not_active Ceased
- 2003-07-02 EP EP03762615A patent/EP1558577B1/en not_active Expired - Lifetime
- 2003-07-02 JP JP2004518696A patent/JP2005535650A/ja active Pending
- 2003-07-02 DE DE60330794T patent/DE60330794D1/de not_active Expired - Fee Related
- 2003-07-02 AU AU2003257433A patent/AU2003257433A1/en not_active Abandoned
- 2003-07-02 US US10/520,143 patent/US20060128752A1/en not_active Abandoned
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