JP2004520299A5 - - Google Patents
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- JP2004520299A5 JP2004520299A5 JP2002549683A JP2002549683A JP2004520299A5 JP 2004520299 A5 JP2004520299 A5 JP 2004520299A5 JP 2002549683 A JP2002549683 A JP 2002549683A JP 2002549683 A JP2002549683 A JP 2002549683A JP 2004520299 A5 JP2004520299 A5 JP 2004520299A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- halo
- alkoxy
- cycloalkyl
- halogen
- 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.)
- Pending
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- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 89
- 229910052736 halogen Inorganic materials 0.000 claims 55
- 150000002367 halogens Chemical class 0.000 claims 54
- 150000001875 compounds Chemical class 0.000 claims 49
- 229910052739 hydrogen Inorganic materials 0.000 claims 48
- 239000001257 hydrogen Substances 0.000 claims 48
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 38
- 125000004093 cyano group Chemical group *C#N 0.000 claims 35
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 30
- 150000002431 hydrogen Chemical class 0.000 claims 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 25
- 125000001424 substituent group Chemical group 0.000 claims 24
- 108010046593 Neuropeptide Y5 receptor Proteins 0.000 claims 23
- 102000028582 Neuropeptide Y5 receptor Human genes 0.000 claims 23
- 125000003545 alkoxy group Chemical group 0.000 claims 23
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 22
- 125000000623 heterocyclic group Chemical group 0.000 claims 21
- 125000002837 carbocyclic group Chemical group 0.000 claims 20
- -1 hydroxy, amino Chemical group 0.000 claims 18
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 17
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 15
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 125000001475 halogen functional group Chemical group 0.000 claims 12
- 238000000034 method Methods 0.000 claims 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 7
- 239000003795 chemical substances by application Substances 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims 5
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 5
- 125000002971 oxazolyl group Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 5
- 125000000335 thiazolyl group Chemical group 0.000 claims 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 4
- 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims 4
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 claims 3
- 125000006655 (C3-C8) heteroaryl group Chemical group 0.000 claims 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 239000003446 ligand Substances 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 238000000159 protein binding assay Methods 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000001425 triazolyl group Chemical group 0.000 claims 3
- IRDOMFKPNLFWGW-UHFFFAOYSA-N 1'-(6-methyl-1h-benzimidazol-2-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(CC1)CCN1C1=NC2=CC(C)=CC=C2N1 IRDOMFKPNLFWGW-UHFFFAOYSA-N 0.000 claims 2
- XVMIZJDINZCQRH-UHFFFAOYSA-N C1=CN=C2NC=NC2=C1.C12=CC=CC=C2C(=O)OC21CCNCC2 Chemical compound C1=CN=C2NC=NC2=C1.C12=CC=CC=C2C(=O)OC21CCNCC2 XVMIZJDINZCQRH-UHFFFAOYSA-N 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000030814 Eating disease Diseases 0.000 claims 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 235000014632 disordered eating Nutrition 0.000 claims 2
- 238000000338 in vitro Methods 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- QCYXSEHOIKPNEU-UHFFFAOYSA-N 1'-(1h-benzimidazol-2-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound C12=CC=CC=C2C(=O)OC11CCN(C=2NC3=CC=CC=C3N=2)CC1 QCYXSEHOIKPNEU-UHFFFAOYSA-N 0.000 claims 1
- FSMWTPVKAMLPSN-UHFFFAOYSA-N 1'-(4,6-dichloro-1h-benzimidazol-2-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(CC1)CCN1C1=NC2=CC(Cl)=CC(Cl)=C2N1 FSMWTPVKAMLPSN-UHFFFAOYSA-N 0.000 claims 1
- PMRYRRQZWAWPNO-UHFFFAOYSA-N 1'-(4-chloro-1h-benzimidazol-2-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(CC1)CCN1C1=NC(C=CC=C2Cl)=C2N1 PMRYRRQZWAWPNO-UHFFFAOYSA-N 0.000 claims 1
- QGOAHRMVFCYWPZ-UHFFFAOYSA-N 1'-(5,6-difluoro-1h-benzimidazol-2-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(CC1)CCN1C1=NC(C=C(C(=C2)F)F)=C2N1 QGOAHRMVFCYWPZ-UHFFFAOYSA-N 0.000 claims 1
- PYRWXXAHWYRCJZ-UHFFFAOYSA-N 1'-(5,6-dimethoxy-1h-benzimidazol-2-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(CC1)CCN1C1=NC(C=C(C(=C2)OC)OC)=C2N1 PYRWXXAHWYRCJZ-UHFFFAOYSA-N 0.000 claims 1
- ZETIZXFYVDSTGO-UHFFFAOYSA-N 1'-(5-phenyl-3h-imidazo[4,5-b]pyrazin-2-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound C12=CC=CC=C2C(=O)OC1(CC1)CCN1C(NC1=NC=2)=NC1=NC=2C1=CC=CC=C1 ZETIZXFYVDSTGO-UHFFFAOYSA-N 0.000 claims 1
- CLDMDFGJPGYXPI-UHFFFAOYSA-N 1'-(6-acetyl-1h-benzimidazol-2-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(CC1)CCN1C1=NC2=CC(C(=O)C)=CC=C2N1 CLDMDFGJPGYXPI-UHFFFAOYSA-N 0.000 claims 1
- MYGKOPZLGWXONJ-UHFFFAOYSA-N 1'-(6-benzoyl-1h-benzimidazol-2-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound C=1C=C2NC(N3CCC4(CC3)C3=CC=CC=C3C(=O)O4)=NC2=CC=1C(=O)C1=CC=CC=C1 MYGKOPZLGWXONJ-UHFFFAOYSA-N 0.000 claims 1
- ZMIPLTFCRFYPCJ-UHFFFAOYSA-N 1'-(6-chloro-1h-benzimidazol-2-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(CC1)CCN1C1=NC2=CC(Cl)=CC=C2N1 ZMIPLTFCRFYPCJ-UHFFFAOYSA-N 0.000 claims 1
- UJHHJWQXFSURDR-UHFFFAOYSA-N 1'-(6-ethoxy-1h-benzimidazol-2-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(CC1)CCN1C1=NC2=CC(OCC)=CC=C2N1 UJHHJWQXFSURDR-UHFFFAOYSA-N 0.000 claims 1
- QNXVMYVJXUTGAH-UHFFFAOYSA-N 1'-(6-fluoro-1h-benzimidazol-2-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(CC1)CCN1C1=NC2=CC(F)=CC=C2N1 QNXVMYVJXUTGAH-UHFFFAOYSA-N 0.000 claims 1
- APXYPHDCNPEEPO-UHFFFAOYSA-N 1'-(6-iodo-4-oxo-1h-quinazolin-2-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(CC1)CCN1C1=NC(=O)C2=CC(I)=CC=C2N1 APXYPHDCNPEEPO-UHFFFAOYSA-N 0.000 claims 1
- BFRHFFHUPOVDTN-UHFFFAOYSA-N 1'-(6-methoxy-1h-benzimidazol-2-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(CC1)CCN1C1=NC2=CC(OC)=CC=C2N1 BFRHFFHUPOVDTN-UHFFFAOYSA-N 0.000 claims 1
- OOFZXDNGMLQFMR-UHFFFAOYSA-N 1'-(6-methylsulfonyl-1h-benzimidazol-2-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(CC1)CCN1C1=NC2=CC(S(=O)(=O)C)=CC=C2N1 OOFZXDNGMLQFMR-UHFFFAOYSA-N 0.000 claims 1
- LPOLBQTZZHSRGO-UHFFFAOYSA-N 1'-(6-propylsulfonyl-1h-benzimidazol-2-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(CC1)CCN1C1=NC2=CC(S(=O)(=O)CCC)=CC=C2N1 LPOLBQTZZHSRGO-UHFFFAOYSA-N 0.000 claims 1
- JNDLYOIUCCIUON-UHFFFAOYSA-N 1'-(6-pyrazin-2-yl-1h-benzimidazol-2-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound C12=CC=CC=C2C(=O)OC1(CC1)CCN1C(NC1=CC=2)=NC1=CC=2C1=CN=CC=N1 JNDLYOIUCCIUON-UHFFFAOYSA-N 0.000 claims 1
- JIVDRBRZFUEQBM-UHFFFAOYSA-N 1'-(6-pyridin-3-yl-1h-benzimidazol-2-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound C12=CC=CC=C2C(=O)OC1(CC1)CCN1C(NC1=CC=2)=NC1=CC=2C1=CC=CN=C1 JIVDRBRZFUEQBM-UHFFFAOYSA-N 0.000 claims 1
- RQMKJTJDJCTLMI-UHFFFAOYSA-N 1'-[6-(1,3-oxazol-2-yl)-1h-benzimidazol-2-yl]spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound C12=CC=CC=C2C(=O)OC1(CC1)CCN1C(NC1=CC=2)=NC1=CC=2C1=NC=CO1 RQMKJTJDJCTLMI-UHFFFAOYSA-N 0.000 claims 1
- PUGBOUNLKDOYBK-UHFFFAOYSA-N 1'-[6-(3,5-dimethyl-1,2-oxazol-4-yl)-1h-benzimidazol-2-yl]spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound CC1=NOC(C)=C1C1=CC=C(NC(=N2)N3CCC4(CC3)C3=CC=CC=C3C(=O)O4)C2=C1 PUGBOUNLKDOYBK-UHFFFAOYSA-N 0.000 claims 1
- VDEGUCQDJLBHGP-UHFFFAOYSA-N 1'-[6-(trifluoromethoxy)-1h-benzimidazol-2-yl]spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(CC1)CCN1C1=NC2=CC(OC(F)(F)F)=CC=C2N1 VDEGUCQDJLBHGP-UHFFFAOYSA-N 0.000 claims 1
- GOSQWFMKXKORBV-UHFFFAOYSA-N 1'-[6-(trifluoromethyl)-1h-benzimidazol-2-yl]spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(CC1)CCN1C1=NC2=CC(C(F)(F)F)=CC=C2N1 GOSQWFMKXKORBV-UHFFFAOYSA-N 0.000 claims 1
- FGCDLQZYHPYSSV-UHFFFAOYSA-N 1'-[6-(trifluoromethylsulfonyl)-1h-benzimidazol-2-yl]spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(CC1)CCN1C1=NC2=CC(S(=O)(=O)C(F)(F)F)=CC=C2N1 FGCDLQZYHPYSSV-UHFFFAOYSA-N 0.000 claims 1
- XWCWKHBTXAFSRD-UHFFFAOYSA-N 2-(3-oxospiro[2-benzofuran-1,4'-piperidine]-1'-yl)-3h-benzimidazole-5-carbonitrile Chemical compound C12=CC=CC=C2C(=O)OC11CCN(C=2NC3=CC=C(C=C3N=2)C#N)CC1 XWCWKHBTXAFSRD-UHFFFAOYSA-N 0.000 claims 1
- UFUKIJYVRWRXGP-UHFFFAOYSA-N 2-(3-oxospiro[2-benzofuran-1,4'-piperidine]-1'-yl)-3h-benzimidazole-5-carboxylic acid Chemical compound O1C(=O)C2=CC=CC=C2C1(CC1)CCN1C1=NC2=CC(C(=O)O)=CC=C2N1 UFUKIJYVRWRXGP-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- FAGMFPJUDWIQNI-UHFFFAOYSA-N 4-[[(3-oxospiro[2-benzofuran-1,4'-piperidine]-1'-carbonyl)amino]methyl]cyclohexane-1-carboxylic acid Chemical compound C1CC(C(=O)O)CCC1CNC(=O)N1CCC2(C3=CC=CC=C3C(=O)O2)CC1 FAGMFPJUDWIQNI-UHFFFAOYSA-N 0.000 claims 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- 230000008484 agonism Effects 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 230000008485 antagonism Effects 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- 150000001924 cycloalkanes Chemical class 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 1
- 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 1
- 238000001514 detection method Methods 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000012530 fluid Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 239000000499 gel Substances 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- LOFHXKUHUMVONQ-UHFFFAOYSA-N n-cyclohexyl-3-oxospiro[2-benzofuran-1,4'-piperidine]-1'-carboxamide Chemical compound C1CC2(C3=CC=CC=C3C(=O)O2)CCN1C(=O)NC1CCCCC1 LOFHXKUHUMVONQ-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 238000002601 radiography Methods 0.000 claims 1
- 229940075993 receptor modulator Drugs 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25499000P | 2000-12-12 | 2000-12-12 | |
| PCT/US2001/047863 WO2002048152A2 (en) | 2000-12-12 | 2001-12-11 | Spiro[isobenzofuran-1,4'-piperidin]-3-ones and 3h-spiroisobenzofuran-1,4'-piperidines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004520299A JP2004520299A (ja) | 2004-07-08 |
| JP2004520299A5 true JP2004520299A5 (https=) | 2005-12-22 |
Family
ID=22966369
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002549683A Pending JP2004520299A (ja) | 2000-12-12 | 2001-12-11 | スピロ[イソベンゾフラン−1,4’−ピペリジン]−3−オン類及び3h−スピロイソベンゾフラン−1,4’−ピペリジン類 |
Country Status (10)
| Country | Link |
|---|---|
| US (4) | US6566367B2 (https=) |
| EP (1) | EP1347982B1 (https=) |
| JP (1) | JP2004520299A (https=) |
| AT (1) | ATE310004T1 (https=) |
| AU (1) | AU2002220276A1 (https=) |
| BR (1) | BR0116113A (https=) |
| DE (1) | DE60115092T2 (https=) |
| ES (1) | ES2249384T3 (https=) |
| MX (1) | MXPA03004245A (https=) |
| WO (1) | WO2002048152A2 (https=) |
Families Citing this family (147)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6374762B1 (en) * | 1997-10-27 | 2002-04-23 | Correct Craft, Inc. | Water sport towing apparatus |
| ATE314371T1 (de) | 1998-11-10 | 2006-01-15 | Merck & Co Inc | Spiro-indole als y5-rezeptor antagonisten |
| JP2003510325A (ja) * | 1999-09-30 | 2003-03-18 | ニューロジェン・コーポレーション | ある種のアルキレンジアミン−置換ピラゾロ[1,5−a]−1,5−ピリミジン及びピラゾロ[1,5−a]−1,3,5−トリアジン |
| IL148903A0 (en) * | 1999-09-30 | 2002-09-12 | Neurogen Corp | Certain alkylene diamine-substituted heterocycles |
| EP1263768A4 (en) * | 2000-01-28 | 2004-05-12 | Neurogen Corp | CHIMEAN NEUROPEPTID Y RECEPTORS |
| BR0116113A (pt) * | 2000-12-12 | 2004-08-03 | Neurogen Corp | Espiro[isobenzofuran-1,4'-piperidin]-3-onas e 3h-espiroisoben-zofuran-1,4'-piperidinas |
| US6900220B2 (en) * | 2001-01-02 | 2005-05-31 | Syntex (U.S.A.) Llc | Quinazolone derivatives as alpha 1A/B adrenergic receptor antagonists |
| WO2002094825A1 (en) * | 2001-05-22 | 2002-11-28 | Banyu Pharmaceutical Co., Ltd. | Novel spiropiperidine derivative |
| ATE427935T1 (de) | 2001-08-07 | 2009-04-15 | Banyu Pharma Co Ltd | Spiro isobenzofurane als neuropeptid y rezeptor antagonisten |
| CA2403307A1 (en) * | 2001-10-23 | 2003-04-23 | Neurogen Corporation | Substituted 2-cyclohexyl-4-phenyl-1h-imidazole derivatives |
| AUPR975601A0 (en) * | 2001-12-24 | 2002-01-31 | Fujisawa Pharmaceutical Co., Ltd. | Quinazolinone derivatives |
| EP1501514B1 (en) * | 2002-05-03 | 2012-12-19 | Exelixis, Inc. | Protein kinase modulators and methods of use |
| US7704995B2 (en) * | 2002-05-03 | 2010-04-27 | Exelixis, Inc. | Protein kinase modulators and methods of use |
| US7405234B2 (en) * | 2002-05-17 | 2008-07-29 | Bristol-Myers Squibb Company | Bicyclic modulators of androgen receptor function |
| US7105526B2 (en) | 2002-06-28 | 2006-09-12 | Banyu Pharmaceuticals Co., Ltd. | Benzimidazole derivatives |
| JP4496722B2 (ja) * | 2002-06-28 | 2010-07-07 | 萬有製薬株式会社 | 新規ベンズイミダゾール誘導体 |
| SE0202462D0 (sv) * | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | Novel use |
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| JP2003510325A (ja) * | 1999-09-30 | 2003-03-18 | ニューロジェン・コーポレーション | ある種のアルキレンジアミン−置換ピラゾロ[1,5−a]−1,5−ピリミジン及びピラゾロ[1,5−a]−1,3,5−トリアジン |
| EP1263768A4 (en) | 2000-01-28 | 2004-05-12 | Neurogen Corp | CHIMEAN NEUROPEPTID Y RECEPTORS |
| WO2001095856A2 (en) | 2000-06-15 | 2001-12-20 | Chaconne Nsi Co., Ltd. | Urea derivative useful as an anti-cancer agent and process for preparing same |
| BR0116113A (pt) * | 2000-12-12 | 2004-08-03 | Neurogen Corp | Espiro[isobenzofuran-1,4'-piperidin]-3-onas e 3h-espiroisoben-zofuran-1,4'-piperidinas |
| CA2403307A1 (en) * | 2001-10-23 | 2003-04-23 | Neurogen Corporation | Substituted 2-cyclohexyl-4-phenyl-1h-imidazole derivatives |
-
2001
- 2001-12-11 BR BR0116113-0A patent/BR0116113A/pt not_active IP Right Cessation
- 2001-12-11 US US10/013,846 patent/US6566367B2/en not_active Expired - Fee Related
- 2001-12-11 JP JP2002549683A patent/JP2004520299A/ja active Pending
- 2001-12-11 DE DE60115092T patent/DE60115092T2/de not_active Expired - Fee Related
- 2001-12-11 AU AU2002220276A patent/AU2002220276A1/en not_active Abandoned
- 2001-12-11 EP EP01270536A patent/EP1347982B1/en not_active Expired - Lifetime
- 2001-12-11 ES ES01270536T patent/ES2249384T3/es not_active Expired - Lifetime
- 2001-12-11 MX MXPA03004245A patent/MXPA03004245A/es active IP Right Grant
- 2001-12-11 WO PCT/US2001/047863 patent/WO2002048152A2/en not_active Ceased
- 2001-12-11 AT AT01270536T patent/ATE310004T1/de not_active IP Right Cessation
- 2001-12-11 US US10/415,457 patent/US20050033048A1/en not_active Abandoned
-
2003
- 2003-04-09 US US10/410,648 patent/US6943199B2/en not_active Expired - Fee Related
-
2005
- 2005-07-18 US US11/183,615 patent/US20060040964A1/en not_active Abandoned
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