CA2319275C - Bicyclic pyridine and pyrimidine derivatives as neuropeptide y receptor antagonists - Google Patents
Bicyclic pyridine and pyrimidine derivatives as neuropeptide y receptor antagonists Download PDFInfo
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- CA2319275C CA2319275C CA002319275A CA2319275A CA2319275C CA 2319275 C CA2319275 C CA 2319275C CA 002319275 A CA002319275 A CA 002319275A CA 2319275 A CA2319275 A CA 2319275A CA 2319275 C CA2319275 C CA 2319275C
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- Prior art keywords
- alkyl
- cycloalkyl
- alkoxy
- radical
- aryl
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims description 3
- 125000002619 bicyclic group Chemical group 0.000 title description 3
- 150000003230 pyrimidines Chemical class 0.000 title description 3
- 239000002660 neuropeptide Y receptor antagonist Substances 0.000 title description 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 132
- 239000000203 mixture Substances 0.000 claims abstract description 28
- 208000008589 Obesity Diseases 0.000 claims abstract description 23
- 235000020824 obesity Nutrition 0.000 claims abstract description 23
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 17
- 230000004634 feeding behavior Effects 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 557
- -1 -OH Chemical group 0.000 claims description 436
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 435
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 434
- 125000001072 heteroaryl group Chemical group 0.000 claims description 358
- 125000003118 aryl group Chemical group 0.000 claims description 342
- 150000003254 radicals Chemical class 0.000 claims description 342
- 125000003545 alkoxy group Chemical group 0.000 claims description 287
- 229910052739 hydrogen Inorganic materials 0.000 claims description 277
- 125000004104 aryloxy group Chemical group 0.000 claims description 268
- 239000001257 hydrogen Substances 0.000 claims description 244
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 241
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 214
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 198
- 125000005843 halogen group Chemical group 0.000 claims description 197
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 190
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 190
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 149
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 114
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 110
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 109
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 108
- 125000000623 heterocyclic group Chemical group 0.000 claims description 108
- 229910020008 S(O) Inorganic materials 0.000 claims description 87
- 150000002431 hydrogen Chemical group 0.000 claims description 83
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims description 69
- 150000003839 salts Chemical class 0.000 claims description 66
- 125000004432 carbon atom Chemical group C* 0.000 claims description 57
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 53
- 150000002148 esters Chemical class 0.000 claims description 51
- 125000001153 fluoro group Chemical group F* 0.000 claims description 50
- 229910052799 carbon Inorganic materials 0.000 claims description 47
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
- 125000004423 acyloxy group Chemical group 0.000 claims description 45
- 239000012453 solvate Substances 0.000 claims description 44
- 229910052717 sulfur Inorganic materials 0.000 claims description 41
- 150000001204 N-oxides Chemical class 0.000 claims description 40
- 229910052760 oxygen Inorganic materials 0.000 claims description 27
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 24
- 125000002950 monocyclic group Chemical group 0.000 claims description 23
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 claims description 19
- 125000003107 substituted aryl group Chemical group 0.000 claims description 19
- 125000001246 bromo group Chemical group Br* 0.000 claims description 14
- 238000011321 prophylaxis Methods 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052727 yttrium Inorganic materials 0.000 claims description 12
- 101100134929 Gallus gallus COR9 gene Proteins 0.000 claims description 11
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- KCTZOTUQSGYWLV-UHFFFAOYSA-N N1C=NC=C2N=CC=C21 Chemical compound N1C=NC=C2N=CC=C21 KCTZOTUQSGYWLV-UHFFFAOYSA-N 0.000 claims description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 3
- HFIVJEORNLARNN-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-methyl-7-piperidin-1-yl-1h-pyrrolo[3,2-b]pyridine Chemical compound C=12NC(C=3C=CC(F)=CC=3)=CC2=NC(C)=CC=1N1CCCCC1 HFIVJEORNLARNN-UHFFFAOYSA-N 0.000 claims 2
- FGISNVXRIOFKCD-UHFFFAOYSA-N 2-(cyclohexen-1-yl)-7-piperidin-1-yl-1h-pyrrolo[3,2-b]pyridine;hydrochloride Chemical compound Cl.C1CCCCN1C1=CC=NC2=C1NC(C=1CCCCC=1)=C2 FGISNVXRIOFKCD-UHFFFAOYSA-N 0.000 claims 2
- VHLAEBPEAQVKAB-UHFFFAOYSA-N 2-cyclohexyl-7-piperidin-1-yl-1h-pyrrolo[3,2-b]pyridine Chemical compound C1CCCCC1C1=CC2=NC=CC(N3CCCCC3)=C2N1 VHLAEBPEAQVKAB-UHFFFAOYSA-N 0.000 claims 2
- DMGOZCOEMMLYBQ-UHFFFAOYSA-N 2-methyl-6-phenyl-4-pyrrolidin-1-yl-5h-pyrrolo[3,2-d]pyrimidine Chemical compound C=12NC(C=3C=CC=CC=3)=CC2=NC(C)=NC=1N1CCCC1 DMGOZCOEMMLYBQ-UHFFFAOYSA-N 0.000 claims 2
- ZNAUJPUZCODAPL-IYBDPMFKSA-N 4-[(2s,6r)-2,6-dimethylpiperidin-1-yl]-6-(4-fluorophenyl)-2-methylpyrrolo[2,3-c]pyridine Chemical compound C[C@H]1CCC[C@@H](C)N1C1=CN(C=2C=CC(F)=CC=2)C=C2C1=CC(C)=N2 ZNAUJPUZCODAPL-IYBDPMFKSA-N 0.000 claims 2
- SZZDYFWEHMPCAS-UHFFFAOYSA-N 7-piperidin-1-yl-2-pyridin-2-yl-1h-pyrrolo[3,2-b]pyridine Chemical compound C1CCCCN1C1=CC=NC2=C1NC(C=1N=CC=CC=1)=C2 SZZDYFWEHMPCAS-UHFFFAOYSA-N 0.000 claims 2
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- KLSNEFPIXYMBHH-UHFFFAOYSA-N 1-(2-methyl-6-phenyl-5h-pyrrolo[3,2-d]pyrimidin-4-yl)pyrrolidin-3-ol Chemical compound C=12NC(C=3C=CC=CC=3)=CC2=NC(C)=NC=1N1CCC(O)C1 KLSNEFPIXYMBHH-UHFFFAOYSA-N 0.000 claims 1
- LSELFBQZZQRNQO-UHFFFAOYSA-N 14-methyl-10-phenyl-2,9,13,15-tetrazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(15),10,12(16),13-tetraene Chemical compound C=1C(C=23)=NC(C)=NC=2N2CCCCC2CN3C=1C1=CC=CC=C1 LSELFBQZZQRNQO-UHFFFAOYSA-N 0.000 claims 1
- NRFWKHLSQWNDNN-UHFFFAOYSA-N 2-(2-methyl-6-phenyl-5h-pyrrolo[3,2-d]pyrimidin-4-yl)-1,3-thiazole Chemical compound C=12NC(C=3C=CC=CC=3)=CC2=NC(C)=NC=1C1=NC=CS1 NRFWKHLSQWNDNN-UHFFFAOYSA-N 0.000 claims 1
- HMWHEASDSOUKNI-UHFFFAOYSA-N 2-(2-methyl-6-phenylpiperidin-4-yl)-1-oxidothieno[3,2-d]pyrimidin-1-ium Chemical compound N1C(C)CC(C=2[N+](=C3C=CSC3=CN=2)[O-])CC1C1=CC=CC=C1 HMWHEASDSOUKNI-UHFFFAOYSA-N 0.000 claims 1
- VQABLVZTEBQHDS-UHFFFAOYSA-N 2-(2-methyl-6-phenylpiperidin-4-yl)furo[3,2-d]pyrimidine Chemical compound N1C(C)CC(C=2N=C3C=COC3=CN=2)CC1C1=CC=CC=C1 VQABLVZTEBQHDS-UHFFFAOYSA-N 0.000 claims 1
- GSZYQNUCJIAZJL-UHFFFAOYSA-N 2-(2-methyl-6-phenylpiperidin-4-yl)thieno[3,2-d]pyrimidine Chemical compound N1C(C)CC(C=2N=C3C=CSC3=CN=2)CC1C1=CC=CC=C1 GSZYQNUCJIAZJL-UHFFFAOYSA-N 0.000 claims 1
- YXONCKUDCNBMHL-UHFFFAOYSA-N 2-(2-tert-butyl-6-methylpiperidin-4-yl)-1-oxidothieno[3,2-d]pyrimidin-1-ium Chemical compound C1C(C(C)(C)C)NC(C)CC1C1=NC=C(SC=C2)C2=[N+]1[O-] YXONCKUDCNBMHL-UHFFFAOYSA-N 0.000 claims 1
- VJTAHVDANNKYPH-UHFFFAOYSA-N 2-(2-tert-butyl-6-methylpiperidin-4-yl)thieno[3,2-d]pyrimidine Chemical compound C1C(C(C)(C)C)NC(C)CC1C1=NC=C(SC=C2)C2=N1 VJTAHVDANNKYPH-UHFFFAOYSA-N 0.000 claims 1
- QXCNPUFYISWMAY-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-methyl-7-piperidin-1-ylfuro[3,2-b]pyridine Chemical compound C=12OC(C=3C=CC(F)=CC=3)=CC2=NC(C)=CC=1N1CCCCC1 QXCNPUFYISWMAY-UHFFFAOYSA-N 0.000 claims 1
- CGTPYVUQAVCXGU-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)-6-methylpiperidin-4-yl]-1-oxidothieno[3,2-d]pyrimidin-1-ium Chemical compound N1C(C)CC(C=2[N+](=C3C=CSC3=CN=2)[O-])CC1C1=CC=C(Cl)C=C1 CGTPYVUQAVCXGU-UHFFFAOYSA-N 0.000 claims 1
- MYLPTZDXJPMVMW-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)-6-methylpiperidin-4-yl]thieno[3,2-d]pyrimidine Chemical compound N1C(C)CC(C=2N=C3C=CSC3=CN=2)CC1C1=CC=C(Cl)C=C1 MYLPTZDXJPMVMW-UHFFFAOYSA-N 0.000 claims 1
- YRYDJESLVLBPRI-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)-6-methylpiperidin-4-yl]thieno[3,2-d]pyrimidine Chemical compound N1C(C)CC(C=2N=C3C=CSC3=CN=2)CC1C1=CC=C(F)C=C1 YRYDJESLVLBPRI-UHFFFAOYSA-N 0.000 claims 1
- FBBILEZNZDSPJM-UHFFFAOYSA-N 2-butyl-5-methyl-7-piperidin-1-ylfuro[3,2-b]pyridine Chemical compound C=12OC(CCCC)=CC2=NC(C)=CC=1N1CCCCC1 FBBILEZNZDSPJM-UHFFFAOYSA-N 0.000 claims 1
- RNQZOKCAVOJNSG-UHFFFAOYSA-N 2-methyl-4-(2-methylpyrrolidin-1-yl)-6-phenyl-5h-pyrrolo[3,2-d]pyrimidine Chemical compound CC1CCCN1C1=NC(C)=NC2=C1NC(C=1C=CC=CC=1)=C2 RNQZOKCAVOJNSG-UHFFFAOYSA-N 0.000 claims 1
- KVZDNBWSPOUUHF-UHFFFAOYSA-N 2-methyl-6-phenyl-4-(4-phenylpiperazin-1-yl)-5h-pyrrolo[3,2-d]pyrimidine Chemical compound C=12NC(C=3C=CC=CC=3)=CC2=NC(C)=NC=1N(CC1)CCN1C1=CC=CC=C1 KVZDNBWSPOUUHF-UHFFFAOYSA-N 0.000 claims 1
- WVUPXOVXHJCBCF-UHFFFAOYSA-N 2-methyl-6-phenyl-4-pyridin-3-yl-5h-pyrrolo[3,2-d]pyrimidine Chemical compound C=12NC(C=3C=CC=CC=3)=CC2=NC(C)=NC=1C1=CC=CN=C1 WVUPXOVXHJCBCF-UHFFFAOYSA-N 0.000 claims 1
- CSABZLYAAMAGRM-UHFFFAOYSA-N 2-methyl-6-phenyl-4-thiophen-2-yl-5h-pyrrolo[3,2-d]pyrimidine Chemical compound C=12NC(C=3C=CC=CC=3)=CC2=NC(C)=NC=1C1=CC=CS1 CSABZLYAAMAGRM-UHFFFAOYSA-N 0.000 claims 1
- FGVYRZPTQVFCBR-UHFFFAOYSA-N 3-(7-piperidin-1-yl-1h-pyrrolo[3,2-b]pyridin-2-yl)phenol Chemical compound OC1=CC=CC(C=2NC3=C(N4CCCCC4)C=CN=C3C=2)=C1 FGVYRZPTQVFCBR-UHFFFAOYSA-N 0.000 claims 1
- BRJUMHZFFDMHHS-UHFFFAOYSA-N 4-(2,5-dihydropyrrol-1-yl)-2-methyl-6-phenylfuro[3,2-d]pyrimidine Chemical compound C=12OC(C=3C=CC=CC=3)=CC2=NC(C)=NC=1N1CC=CC1 BRJUMHZFFDMHHS-UHFFFAOYSA-N 0.000 claims 1
- PDORTDCGJIZCFI-UHFFFAOYSA-N 4-(3,4-dihydro-1h-isoquinolin-2-yl)-2-methyl-6-phenylthieno[3,2-d]pyrimidine Chemical compound C=1C2=NC(C)=NC(N3CC4=CC=CC=C4CC3)=C2SC=1C1=CC=CC=C1 PDORTDCGJIZCFI-UHFFFAOYSA-N 0.000 claims 1
- NWZPSAYBNUDYIN-UHFFFAOYSA-N 4-(3,6-dihydro-2h-pyridin-1-yl)-2-methyl-6-phenylthieno[3,2-d]pyrimidine Chemical compound C=12SC(C=3C=CC=CC=3)=CC2=NC(C)=NC=1N1CCC=CC1 NWZPSAYBNUDYIN-UHFFFAOYSA-N 0.000 claims 1
- TZGGZZBAQIYWER-UHFFFAOYSA-N 4-[6-(3,4-difluorophenyl)-2-methyl-5h-pyrrolo[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=12NC(C=3C=C(F)C(F)=CC=3)=CC2=NC(C)=NC=1N1CCOCC1 TZGGZZBAQIYWER-UHFFFAOYSA-N 0.000 claims 1
- VKIUHUMRZNAVCE-UHFFFAOYSA-N 5-methyl-2-phenyl-7-piperidin-1-ylfuro[3,2-b]pyridine Chemical compound C=12OC(C=3C=CC=CC=3)=CC2=NC(C)=CC=1N1CCCCC1 VKIUHUMRZNAVCE-UHFFFAOYSA-N 0.000 claims 1
- QIOGUVQYQLSKRN-UHFFFAOYSA-N 5-methyl-7-piperidin-1-yl-2-(2-piperidin-4-ylphenyl)furo[3,2-b]pyridine Chemical compound C=12OC(C=3C(=CC=CC=3)C3CCNCC3)=CC2=NC(C)=CC=1N1CCCCC1 QIOGUVQYQLSKRN-UHFFFAOYSA-N 0.000 claims 1
- AVEGRVARZBQTOL-UHFFFAOYSA-N 6-(4-chlorophenyl)-2-ethyl-4-piperidin-1-ylfuro[3,2-d]pyrimidine Chemical compound C=12OC(C=3C=CC(Cl)=CC=3)=CC2=NC(CC)=NC=1N1CCCCC1 AVEGRVARZBQTOL-UHFFFAOYSA-N 0.000 claims 1
- RVILBIGPONZNMB-UHFFFAOYSA-N 6-(4-chlorophenyl)-2-methyl-4-piperidin-1-ylfuro[3,2-d]pyrimidine Chemical compound C=12OC(C=3C=CC(Cl)=CC=3)=CC2=NC(C)=NC=1N1CCCCC1 RVILBIGPONZNMB-UHFFFAOYSA-N 0.000 claims 1
- JIJBNODYTQRFQR-UHFFFAOYSA-N 6-(4-fluorophenyl)-2-methyl-4-(2-methylpiperidin-1-yl)-5h-pyrrolo[3,2-d]pyrimidine Chemical compound CC1CCCCN1C1=NC(C)=NC2=C1NC(C=1C=CC(F)=CC=1)=C2 JIJBNODYTQRFQR-UHFFFAOYSA-N 0.000 claims 1
- ZJSHGKFUEPNFHP-UHFFFAOYSA-N C(C)C1=NC(=C2C(N1)=CC(=N2)C2=CC=CC=C2)N2CC1=CC=CC=C1CC2 Chemical compound C(C)C1=NC(=C2C(N1)=CC(=N2)C2=CC=CC=C2)N2CC1=CC=CC=C1CC2 ZJSHGKFUEPNFHP-UHFFFAOYSA-N 0.000 claims 1
- AREJQYKTNHEJRM-UHFFFAOYSA-N C1(=CC=CC=C1)C1CC(CCN1)C1=C2C(NC(=N1)NCCC)=CC=N2 Chemical compound C1(=CC=CC=C1)C1CC(CCN1)C1=C2C(NC(=N1)NCCC)=CC=N2 AREJQYKTNHEJRM-UHFFFAOYSA-N 0.000 claims 1
- IULADUGXHYYHPM-UHFFFAOYSA-N C12(CC3CC(CC(C1)C3)C2)C2CC(CC(N2)C)C2=NC=C3C(N2)=CC=N3 Chemical compound C12(CC3CC(CC(C1)C3)C2)C2CC(CC(N2)C)C2=NC=C3C(N2)=CC=N3 IULADUGXHYYHPM-UHFFFAOYSA-N 0.000 claims 1
- DYHKIZKGIGJEDE-UHFFFAOYSA-N C1=C2NC(C)=NC(N3C4CCC3CCC4)=C2N=C1C1=CC=CC=C1 Chemical compound C1=C2NC(C)=NC(N3C4CCC3CCC4)=C2N=C1C1=CC=CC=C1 DYHKIZKGIGJEDE-UHFFFAOYSA-N 0.000 claims 1
- KHAVNMJZDWGRHD-UHFFFAOYSA-N C1=NC(C)=CC(C=2NC3=CC(=NC3=CN=2)C=2C=C(F)C(O)=CC=2)=C1 Chemical compound C1=NC(C)=CC(C=2NC3=CC(=NC3=CN=2)C=2C=C(F)C(O)=CC=2)=C1 KHAVNMJZDWGRHD-UHFFFAOYSA-N 0.000 claims 1
- LJYNJEIJQYGDMT-UHFFFAOYSA-N C1CC(CC(N1)c1ccccc1)Nc1ncc2nccc2[nH]1 Chemical compound C1CC(CC(N1)c1ccccc1)Nc1ncc2nccc2[nH]1 LJYNJEIJQYGDMT-UHFFFAOYSA-N 0.000 claims 1
- OXTKALMGVPAARX-UHFFFAOYSA-N C1CC1C1CC(CC(N1)c1ccccc1)c1ncc2nccc2[nH]1 Chemical compound C1CC1C1CC(CC(N1)c1ccccc1)c1ncc2nccc2[nH]1 OXTKALMGVPAARX-UHFFFAOYSA-N 0.000 claims 1
- JJLRHWKCKULJLT-UHFFFAOYSA-N C1CN(CCN1C1CC(CC(N1)c1ccccc1)c1ncc2nccc2[nH]1)c1ccccc1 Chemical compound C1CN(CCN1C1CC(CC(N1)c1ccccc1)c1ncc2nccc2[nH]1)c1ccccc1 JJLRHWKCKULJLT-UHFFFAOYSA-N 0.000 claims 1
- UZXVPKWNXQWRLJ-UHFFFAOYSA-N C1CNC(C)CC1C(N1)=NC=C2C1=CC(C=1C=C(N)C=CC=1)=N2 Chemical compound C1CNC(C)CC1C(N1)=NC=C2C1=CC(C=1C=C(N)C=CC=1)=N2 UZXVPKWNXQWRLJ-UHFFFAOYSA-N 0.000 claims 1
- MAYRGCAQXKIOEJ-UHFFFAOYSA-N C1CNC(C)CC1C(N1)=NC=C2C1=CC(C=1C=CC(N)=CC=1)=N2 Chemical compound C1CNC(C)CC1C(N1)=NC=C2C1=CC(C=1C=CC(N)=CC=1)=N2 MAYRGCAQXKIOEJ-UHFFFAOYSA-N 0.000 claims 1
- LQELISGMDMJGGR-UHFFFAOYSA-N C=12N=C(C=3C=CC=CC=3)C=C2NC(C)=NC=1N1CCC=C1 Chemical compound C=12N=C(C=3C=CC=CC=3)C=C2NC(C)=NC=1N1CCC=C1 LQELISGMDMJGGR-UHFFFAOYSA-N 0.000 claims 1
- PYQPLUULKKMMBG-UHFFFAOYSA-N CC(C)C1CC(CC(N1)c1ccccc1)c1ncc2nccc2[nH]1 Chemical compound CC(C)C1CC(CC(N1)c1ccccc1)c1ncc2nccc2[nH]1 PYQPLUULKKMMBG-UHFFFAOYSA-N 0.000 claims 1
- VELBIJQHOXXDHB-UHFFFAOYSA-N CC(C)CC1CC(CC(N1)c1ccccc1)c1ncc2nccc2[nH]1 Chemical compound CC(C)CC1CC(CC(N1)c1ccccc1)c1ncc2nccc2[nH]1 VELBIJQHOXXDHB-UHFFFAOYSA-N 0.000 claims 1
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| PCT/US1999/002500 WO1999040091A1 (en) | 1998-02-06 | 1999-02-05 | Bicyclic pyridine and pyrimidine derivatives as neuropeptide y receptor antagonists |
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-
1999
- 1999-02-04 US US09/246,775 patent/US6187777B1/en not_active Expired - Fee Related
- 1999-02-05 SI SI9930893T patent/SI1054887T1/sl unknown
- 1999-02-05 PT PT99906756T patent/PT1054887E/pt unknown
- 1999-02-05 AU AU26590/99A patent/AU747920B2/en not_active Ceased
- 1999-02-05 DE DE69930835T patent/DE69930835T2/de not_active Expired - Lifetime
- 1999-02-05 AT AT99906756T patent/ATE323088T1/de not_active IP Right Cessation
- 1999-02-05 JP JP2000530520A patent/JP2003502272A/ja not_active Withdrawn
- 1999-02-05 CA CA002319275A patent/CA2319275C/en not_active Expired - Fee Related
- 1999-02-05 EP EP99906756A patent/EP1054887B1/en not_active Expired - Lifetime
- 1999-02-05 WO PCT/US1999/002500 patent/WO1999040091A1/en not_active Ceased
- 1999-02-05 ES ES99906756T patent/ES2257851T3/es not_active Expired - Lifetime
- 1999-02-05 DK DK99906756T patent/DK1054887T3/da active
-
2000
- 2000-08-16 US US09/640,263 patent/US6583154B1/en not_active Expired - Fee Related
-
2006
- 2006-07-06 CY CY20061100932T patent/CY1105476T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1054887B1 (en) | 2006-04-12 |
| AU2659099A (en) | 1999-08-23 |
| SI1054887T1 (sl) | 2006-08-31 |
| CA2319275A1 (en) | 1999-08-12 |
| PT1054887E (pt) | 2006-06-30 |
| ES2257851T3 (es) | 2006-08-01 |
| JP2003502272A (ja) | 2003-01-21 |
| ATE323088T1 (de) | 2006-04-15 |
| DK1054887T3 (da) | 2006-05-08 |
| DE69930835D1 (de) | 2006-05-24 |
| DE69930835T2 (de) | 2006-10-19 |
| US6583154B1 (en) | 2003-06-24 |
| EP1054887A1 (en) | 2000-11-29 |
| AU747920B2 (en) | 2002-05-30 |
| US6187777B1 (en) | 2001-02-13 |
| CY1105476T1 (el) | 2010-07-28 |
| WO1999040091A1 (en) | 1999-08-12 |
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