SK13752003A3 - Substituted pyrazinones, pyridines and pyrimidines as ligands of factor releasing corticotropine - Google Patents

Substituted pyrazinones, pyridines and pyrimidines as ligands of factor releasing corticotropine Download PDF

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Publication number: SK13752003A3
Authority: SK; Slovakia
Prior art keywords: alkyl; cor; group; cycloalkyl; cycloalkylalkyl
Prior art date: 2001-05-14

Application number

SK1375-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Argyrios G Arvanitis

Paul J Gilligan

Richard A Hartz

Original Assignee

Bristol Myers Squibb Pharma Co

Priority date (The priority date 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 date listed.)

2001-05-14

Filing date

2002-05-14

Publication date

2004-11-03

2002-05-14 Application filed by Bristol Myers Squibb Pharma Co filed Critical Bristol Myers Squibb Pharma Co

2004-11-03 Publication of SK13752003A3 publication Critical patent/SK13752003A3/sk

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HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical class OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 title claims abstract description 18
239000003446 ligand Substances 0.000 title abstract description 9
150000003230 pyrimidines Chemical class 0.000 title abstract description 4
150000003222 pyridines Chemical class 0.000 title abstract description 3
IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 271
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 18
208000019901 Anxiety disease Diseases 0.000 claims abstract description 12
230000036506 anxiety Effects 0.000 claims abstract description 12
208000019022 Mood disease Diseases 0.000 claims abstract description 8
208000017194 Affective disease Diseases 0.000 claims abstract description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 472
-1 -OH Chemical group 0.000 claims description 291
229910052736 halogen Inorganic materials 0.000 claims description 218
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 205
150000002367 halogens Chemical class 0.000 claims description 198
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 194
XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 168
229910052799 carbon Inorganic materials 0.000 claims description 165
125000000217 alkyl group Chemical group 0.000 claims description 163
125000004093 cyano group Chemical group *C#N 0.000 claims description 139
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 123
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 120
125000001072 heteroaryl group Chemical group 0.000 claims description 111
125000003118 aryl group Chemical group 0.000 claims description 101
229910052739 hydrogen Inorganic materials 0.000 claims description 99
125000001424 substituent group Chemical group 0.000 claims description 97
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 86
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 78
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 77
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 74
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 70
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 56
125000005843 halogen group Chemical group 0.000 claims description 54
229910052794 bromium Inorganic materials 0.000 claims description 52
229910052801 chlorine Inorganic materials 0.000 claims description 52
229910052731 fluorine Inorganic materials 0.000 claims description 51
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 50
125000003226 pyrazolyl group Chemical group 0.000 claims description 50
150000003839 salts Chemical class 0.000 claims description 49
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 46
238000000034 method Methods 0.000 claims description 46
125000000623 heterocyclic group Chemical group 0.000 claims description 43
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 41
125000000304 alkynyl group Chemical group 0.000 claims description 40
239000000203 mixture Substances 0.000 claims description 37
125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 36
125000003342 alkenyl group Chemical group 0.000 claims description 36
125000003545 alkoxy group Chemical group 0.000 claims description 35
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 34
125000000753 cycloalkyl group Chemical group 0.000 claims description 33
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
229920006395 saturated elastomer Polymers 0.000 claims description 32
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 30
229910052717 sulfur Inorganic materials 0.000 claims description 29
229910052760 oxygen Inorganic materials 0.000 claims description 28
125000000392 cycloalkenyl group Chemical group 0.000 claims description 26
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 24
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 23
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 22
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 20
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 20
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 20
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 20
229910052757 nitrogen Inorganic materials 0.000 claims description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
125000004429 atom Chemical group 0.000 claims description 17
239000003814 drug Substances 0.000 claims description 17
125000005842 heteroatom Chemical group 0.000 claims description 17
125000000842 isoxazolyl group Chemical group 0.000 claims description 17
125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
241000124008 Mammalia Species 0.000 claims description 13
201000010099 disease Diseases 0.000 claims description 13
229940079593 drug Drugs 0.000 claims description 13
125000004076 pyridyl group Chemical group 0.000 claims description 13
125000001544 thienyl group Chemical group 0.000 claims description 13
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 12
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 12
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 12
125000002541 furyl group Chemical group 0.000 claims description 12
125000002883 imidazolyl group Chemical group 0.000 claims description 12
125000001041 indolyl group Chemical group 0.000 claims description 12
125000005956 isoquinolyl group Chemical group 0.000 claims description 12
125000003373 pyrazinyl group Chemical group 0.000 claims description 12
125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
125000000168 pyrrolyl group Chemical group 0.000 claims description 12
125000005493 quinolyl group Chemical group 0.000 claims description 12
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 12
125000000335 thiazolyl group Chemical group 0.000 claims description 12
125000004306 triazinyl group Chemical group 0.000 claims description 12
125000001624 naphthyl group Chemical group 0.000 claims description 11
125000002971 oxazolyl group Chemical group 0.000 claims description 11
125000002098 pyridazinyl group Chemical group 0.000 claims description 11
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 10
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 10
239000003937 drug carrier Substances 0.000 claims description 9
239000008194 pharmaceutical composition Substances 0.000 claims description 9
125000006308 propyl amino group Chemical group 0.000 claims description 9
FNLSWLSNDSICNE-UHFFFAOYSA-N 5-bromo-3-(5,7-dichloro-2,3-dihydroindol-1-yl)-1-pentan-3-ylpyrazin-2-one Chemical compound O=C1N(C(CC)CC)C=C(Br)N=C1N1C2=C(Cl)C=C(Cl)C=C2CC1 FNLSWLSNDSICNE-UHFFFAOYSA-N 0.000 claims description 8
FTPFMZDMILZENX-UHFFFAOYSA-N 6-(5,7-dichloro-2,3-dihydroindol-1-yl)-2-methyl-n-pentan-3-ylpyrimidin-4-amine Chemical compound CC1=NC(NC(CC)CC)=CC(N2C3=C(Cl)C=C(Cl)C=C3CC2)=N1 FTPFMZDMILZENX-UHFFFAOYSA-N 0.000 claims description 7
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 7
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 6
208000006011 Stroke Diseases 0.000 claims description 6
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 claims description 6
125000004373 methylthiopropyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
125000003831 tetrazolyl group Chemical group 0.000 claims description 6
VDLHLBKVHUIRBW-UHFFFAOYSA-N 4-(5,7-dichloro-2,3-dihydroindol-1-yl)-2-methyl-6-(pentan-3-ylamino)pyrimidine-5-carbaldehyde Chemical compound CCC(CC)NC1=NC(C)=NC(N2C3=C(Cl)C=C(Cl)C=C3CC2)=C1C=O VDLHLBKVHUIRBW-UHFFFAOYSA-N 0.000 claims description 5
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 5
AIKAHWOVVABGTM-UHFFFAOYSA-N 3-(5-methoxy-7-methyl-2,3-dihydroindol-1-yl)-5-methyl-1-pentan-3-ylpyrazin-2-one Chemical compound O=C1N(C(CC)CC)C=C(C)N=C1N1C2=C(C)C=C(OC)C=C2CC1 AIKAHWOVVABGTM-UHFFFAOYSA-N 0.000 claims description 4
GEPHCUOJSFBHCV-UHFFFAOYSA-N 5-bromo-6-(5,7-dichloro-2,3-dihydroindol-1-yl)-2-methyl-n-pentan-3-ylpyrimidin-4-amine Chemical compound CCC(CC)NC1=NC(C)=NC(N2C3=C(Cl)C=C(Cl)C=C3CC2)=C1Br GEPHCUOJSFBHCV-UHFFFAOYSA-N 0.000 claims description 4
DPDMMJDMETVLCD-UHFFFAOYSA-N 6-(5,7-dichloro-2,3-dihydroindol-1-yl)-5-iodo-2-methyl-n-pentan-3-ylpyrimidin-4-amine Chemical compound CCC(CC)NC1=NC(C)=NC(N2C3=C(Cl)C=C(Cl)C=C3CC2)=C1I DPDMMJDMETVLCD-UHFFFAOYSA-N 0.000 claims description 4
208000024827 Alzheimer disease Diseases 0.000 claims description 4
208000018522 Gastrointestinal disease Diseases 0.000 claims description 4
208000008589 Obesity Diseases 0.000 claims description 4
NZTXNNXODPSPJM-UHFFFAOYSA-N [4-(5,7-dichloro-2,3-dihydroindol-1-yl)-2-methyl-6-(pentan-3-ylamino)pyrimidin-5-yl]methanol Chemical compound CCC(CC)NC1=NC(C)=NC(N2C3=C(Cl)C=C(Cl)C=C3CC2)=C1CO NZTXNNXODPSPJM-UHFFFAOYSA-N 0.000 claims description 4
230000002526 effect on cardiovascular system Effects 0.000 claims description 4
208000002551 irritable bowel syndrome Diseases 0.000 claims description 4
235000020824 obesity Nutrition 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 3
CVYRDGZHLKKFDP-UHFFFAOYSA-N 1-butan-2-yl-5-chloro-3-(5-methoxy-7-methyl-2,3-dihydroindol-1-yl)pyrazin-2-one Chemical compound O=C1N(C(C)CC)C=C(Cl)N=C1N1C2=C(C)C=C(OC)C=C2CC1 CVYRDGZHLKKFDP-UHFFFAOYSA-N 0.000 claims description 3
QNUNMRZMUFDHRG-UHFFFAOYSA-N 3-(5,7-dichloro-2,3-dihydroindol-1-yl)-5-ethyl-1-pentan-3-ylpyrazin-2-one Chemical compound O=C1N(C(CC)CC)C=C(CC)N=C1N1C2=C(Cl)C=C(Cl)C=C2CC1 QNUNMRZMUFDHRG-UHFFFAOYSA-N 0.000 claims description 3
TUFGBSLLDDWAIE-UHFFFAOYSA-N 3-(5,7-dichloro-2,3-dihydroindol-1-yl)-5-methyl-1-pentan-3-ylpyrazin-2-one Chemical compound O=C1N(C(CC)CC)C=C(C)N=C1N1C2=C(Cl)C=C(Cl)C=C2CC1 TUFGBSLLDDWAIE-UHFFFAOYSA-N 0.000 claims description 3
RFGRABBQDOMKMQ-UHFFFAOYSA-N 3-(5-bromo-7-chloro-2,3-dihydroindol-1-yl)-1-butan-2-yl-5-chloropyrazin-2-one Chemical compound O=C1N(C(C)CC)C=C(Cl)N=C1N1C2=C(Cl)C=C(Br)C=C2CC1 RFGRABBQDOMKMQ-UHFFFAOYSA-N 0.000 claims description 3
JLXXRVMYDKJXIE-UHFFFAOYSA-N 3-(7-bromo-5-methoxy-2,3-dihydroindol-1-yl)-1-butan-2-yl-5-chloropyrazin-2-one Chemical compound O=C1N(C(C)CC)C=C(Cl)N=C1N1C2=C(Br)C=C(OC)C=C2CC1 JLXXRVMYDKJXIE-UHFFFAOYSA-N 0.000 claims description 3
YGBKKTGDZHUVEX-UHFFFAOYSA-N 3-(7-bromo-5-methoxy-2,3-dihydroindol-1-yl)-5-chloro-1-(1-methoxybutan-2-yl)pyrazin-2-one Chemical compound O=C1N(C(COC)CC)C=C(Cl)N=C1N1C2=C(Br)C=C(OC)C=C2CC1 YGBKKTGDZHUVEX-UHFFFAOYSA-N 0.000 claims description 3
TWLCZOJJGJJLED-UHFFFAOYSA-N 3-(7-bromo-5-methoxy-2,3-dihydroindol-1-yl)-5-chloro-1-(1-methoxypentan-3-yl)pyrazin-2-one Chemical compound O=C1N(C(CCOC)CC)C=C(Cl)N=C1N1C2=C(Br)C=C(OC)C=C2CC1 TWLCZOJJGJJLED-UHFFFAOYSA-N 0.000 claims description 3
RYMXNSXRSZVIIS-UHFFFAOYSA-N 3-(7-bromo-5-methoxy-2,3-dihydroindol-1-yl)-5-chloro-1-(2-methylsulfanylethyl)pyrazin-2-one Chemical compound C1=2C(Br)=CC(OC)=CC=2CCN1C1=NC(Cl)=CN(CCSC)C1=O RYMXNSXRSZVIIS-UHFFFAOYSA-N 0.000 claims description 3
WGXUTRGZXOFMON-OAHLLOKOSA-N 3-(7-bromo-5-methoxy-2,3-dihydroindol-1-yl)-5-chloro-1-[(1r)-1-cyclopropylpropyl]pyrazin-2-one Chemical compound C1([C@@H](CC)N2C(C(N3C4=C(Br)C=C(OC)C=C4CC3)=NC(Cl)=C2)=O)CC1 WGXUTRGZXOFMON-OAHLLOKOSA-N 0.000 claims description 3
YGBKKTGDZHUVEX-GFCCVEGCSA-N 3-(7-bromo-5-methoxy-2,3-dihydroindol-1-yl)-5-chloro-1-[(2r)-1-methoxybutan-2-yl]pyrazin-2-one Chemical compound O=C1N([C@@H](COC)CC)C=C(Cl)N=C1N1C2=C(Br)C=C(OC)C=C2CC1 YGBKKTGDZHUVEX-GFCCVEGCSA-N 0.000 claims description 3
CFLZMBHTXCYTLF-UHFFFAOYSA-N 4-(5,7-dichloro-2,3-dihydroindol-1-yl)-2-methyl-6-(pentan-3-ylamino)pyrimidine-5-carbonitrile Chemical compound CCC(CC)NC1=NC(C)=NC(N2C3=C(Cl)C=C(Cl)C=C3CC2)=C1C#N CFLZMBHTXCYTLF-UHFFFAOYSA-N 0.000 claims description 3
DJUVWRCNBVAGRP-UHFFFAOYSA-N 4-(7-chloro-5-methoxy-2,3-dihydroindol-1-yl)-2-methyl-6-(pentan-3-ylamino)pyrimidine-5-carbonitrile Chemical compound CCC(CC)NC1=NC(C)=NC(N2C3=C(Cl)C=C(OC)C=C3CC2)=C1C#N DJUVWRCNBVAGRP-UHFFFAOYSA-N 0.000 claims description 3
WTZKYLAMYQAWII-UHFFFAOYSA-N 4-(7-chloro-5-methoxy-2,3-dihydroindol-1-yl)-6-(1-methoxybutan-2-ylamino)-2-methylpyrimidine-5-carbaldehyde Chemical compound COCC(CC)NC1=NC(C)=NC(N2C3=C(Cl)C=C(OC)C=C3CC2)=C1C=O WTZKYLAMYQAWII-UHFFFAOYSA-N 0.000 claims description 3
VYGIUFWKAIRNIC-UHFFFAOYSA-N 4-(7-chloro-5-methoxy-2,3-dihydroindol-1-yl)-6-(1-methoxybutan-2-ylamino)-2-methylpyrimidine-5-carbonitrile Chemical compound COCC(CC)NC1=NC(C)=NC(N2C3=C(Cl)C=C(OC)C=C3CC2)=C1C#N VYGIUFWKAIRNIC-UHFFFAOYSA-N 0.000 claims description 3
GDSQCRONLQMTBC-GFCCVEGCSA-N 5-bromo-3-(5,7-dichloro-2,3-dihydroindol-1-yl)-1-[(2r)-1-methoxybutan-2-yl]pyrazin-2-one Chemical compound O=C1N([C@@H](COC)CC)C=C(Br)N=C1N1C2=C(Cl)C=C(Cl)C=C2CC1 GDSQCRONLQMTBC-GFCCVEGCSA-N 0.000 claims description 3
XUNYOUQHODZRFU-UHFFFAOYSA-N 5-bromo-3-(7-bromo-5-methoxy-2,3-dihydroindol-1-yl)-1-pentan-3-ylpyrazin-2-one Chemical compound O=C1N(C(CC)CC)C=C(Br)N=C1N1C2=C(Br)C=C(OC)C=C2CC1 XUNYOUQHODZRFU-UHFFFAOYSA-N 0.000 claims description 3
DDBIMYJYTOEDRE-LLVKDONJSA-N 5-bromo-3-(7-chloro-6-fluoro-5-methoxy-2,3-dihydroindol-1-yl)-1-[(2r)-1-methoxybutan-2-yl]pyrazin-2-one Chemical compound O=C1N([C@@H](COC)CC)C=C(Br)N=C1N1C2=C(Cl)C(F)=C(OC)C=C2CC1 DDBIMYJYTOEDRE-LLVKDONJSA-N 0.000 claims description 3
LFROYWRHRZIVLG-UHFFFAOYSA-N 5-chloro-1-(1-cyclobutylpropyl)-3-(7-methoxy-2,3-dihydro-1,4-benzoxazin-4-yl)pyrazin-2-one Chemical compound C1=C(Cl)N=C(N2C3=CC=C(OC)C=C3OCC2)C(=O)N1C(CC)C1CCC1 LFROYWRHRZIVLG-UHFFFAOYSA-N 0.000 claims description 3
QVSWSIWONHCBOQ-UHFFFAOYSA-N 5-chloro-1-(1-methoxybutan-2-yl)-3-(5-methoxy-7-methyl-2,3-dihydroindol-1-yl)pyrazin-2-one Chemical compound O=C1N(C(COC)CC)C=C(Cl)N=C1N1C2=C(C)C=C(OC)C=C2CC1 QVSWSIWONHCBOQ-UHFFFAOYSA-N 0.000 claims description 3
ONKIDHBQXBINRV-CQSZACIVSA-N 5-chloro-1-[(1r)-1-cyclopropylpropyl]-3-(5,7-dibromo-2,3-dihydroindol-1-yl)pyrazin-2-one Chemical compound C1([C@@H](CC)N2C(C(N3C4=C(Br)C=C(Br)C=C4CC3)=NC(Cl)=C2)=O)CC1 ONKIDHBQXBINRV-CQSZACIVSA-N 0.000 claims description 3
DSWUPCSNGVSVEI-MRXNPFEDSA-N 5-chloro-1-[(1r)-1-cyclopropylpropyl]-3-(5-methoxy-7-methyl-2,3-dihydroindol-1-yl)pyrazin-2-one Chemical compound C1([C@@H](CC)N2C(C(N3C4=C(C)C=C(OC)C=C4CC3)=NC(Cl)=C2)=O)CC1 DSWUPCSNGVSVEI-MRXNPFEDSA-N 0.000 claims description 3
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BWNXWIOKVHHFOK-AWEZNQCLSA-N 5-chloro-1-[(1s)-1-cyclopropylpropyl]-3-(5,7-dichloro-2,3-dihydroindol-1-yl)pyrazin-2-one Chemical compound C1([C@H](CC)N2C(C(N3C4=C(Cl)C=C(Cl)C=C4CC3)=NC(Cl)=C2)=O)CC1 BWNXWIOKVHHFOK-AWEZNQCLSA-N 0.000 claims description 3
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PVGBHEUCHKGFQP-UHFFFAOYSA-M sodium;(1z)-n-[5-amino-2-(4-aminophenyl)sulfonylphenyl]sulfonylethanimidate Chemical compound [Na+].CC(=O)[N-]S(=O)(=O)C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 PVGBHEUCHKGFQP-UHFFFAOYSA-M 0.000 description 1
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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SK1375-2003A 2001-05-14 2002-05-14 Substituted pyrazinones, pyridines and pyrimidines as ligands of factor releasing corticotropine SK13752003A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US29070601P	2001-05-14	2001-05-14
PCT/US2002/015493 WO2002092090A1 (en)	2001-05-14	2002-05-14	Substituted pyrazinones, pyridines and pyrimidines as corticotropin releasing factor ligands

Publications (1)

Publication Number	Publication Date
SK13752003A3 true SK13752003A3 (en)	2004-11-03

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SK1375-2003A SK13752003A3 (en)	2001-05-14	2002-05-14	Substituted pyrazinones, pyridines and pyrimidines as ligands of factor releasing corticotropine

Country Status (22)

Country	Link
US (2)	US7205306B2 (cs)
EP (1)	EP1392309B1 (cs)
JP (1)	JP2004533447A (cs)
KR (1)	KR20030094410A (cs)
CN (1)	CN1527710A (cs)
BG (1)	BG108425A (cs)
BR (1)	BR0209575A (cs)
CA (1)	CA2446980A1 (cs)
CZ (1)	CZ20033053A3 (cs)
DE (1)	DE60217669D1 (cs)
EE (1)	EE200300546A (cs)
HU (1)	HUP0304048A2 (cs)
IL (1)	IL158669A0 (cs)
IS (1)	IS7017A (cs)
MX (1)	MXPA03010324A (cs)
NO (1)	NO20035055D0 (cs)
PL (1)	PL366577A1 (cs)
RU (1)	RU2003135424A (cs)
SK (1)	SK13752003A3 (cs)
WO (1)	WO2002092090A1 (cs)
YU (1)	YU90503A (cs)
ZA (1)	ZA200308729B (cs)

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BRPI1010831A2 (pt)	2009-05-12	2016-04-05	Addex Pharmaceuticals Sa	derivados de 1,2,4-triazolo[4,3-a]piridina e seu como moduladores alostéricos positivos de receptores de mglur2
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2002
- 2002-05-14 CN CNA028140907A patent/CN1527710A/zh active Pending
- 2002-05-14 JP JP2002589007A patent/JP2004533447A/ja active Pending
- 2002-05-14 EP EP02729225A patent/EP1392309B1/en not_active Expired - Lifetime
- 2002-05-14 HU HU0304048A patent/HUP0304048A2/hu unknown
- 2002-05-14 CZ CZ20033053A patent/CZ20033053A3/cs unknown
- 2002-05-14 MX MXPA03010324A patent/MXPA03010324A/es unknown
- 2002-05-14 DE DE60217669T patent/DE60217669D1/de not_active Expired - Lifetime
- 2002-05-14 RU RU2003135424/04A patent/RU2003135424A/ru not_active Application Discontinuation
- 2002-05-14 KR KR10-2003-7014755A patent/KR20030094410A/ko not_active Withdrawn
- 2002-05-14 EE EEP200300546A patent/EE200300546A/xx unknown
- 2002-05-14 BR BR0209575-0A patent/BR0209575A/pt not_active IP Right Cessation
- 2002-05-14 US US10/145,440 patent/US7205306B2/en not_active Expired - Lifetime
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- 2002-05-14 CA CA002446980A patent/CA2446980A1/en not_active Abandoned
- 2002-05-14 WO PCT/US2002/015493 patent/WO2002092090A1/en not_active Ceased
- 2002-05-14 PL PL02366577A patent/PL366577A1/xx unknown
- 2002-05-14 YU YU90503A patent/YU90503A/sh unknown
- 2002-05-14 SK SK1375-2003A patent/SK13752003A3/sk unknown
2003
- 2003-11-07 IS IS7017A patent/IS7017A/is unknown
- 2003-11-10 ZA ZA200308729A patent/ZA200308729B/en unknown
- 2003-11-13 NO NO20035055A patent/NO20035055D0/no not_active Application Discontinuation
- 2003-12-08 BG BG108425A patent/BG108425A/xx unknown
2007
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IS7017A (is)	2003-11-07
CZ20033053A3 (en)	2004-05-12
IL158669A0 (en)	2004-05-12
EE200300546A (et)	2004-04-15
EP1392309A4 (en)	2006-01-18
US7205306B2 (en)	2007-04-17
ZA200308729B (en)	2005-02-10
US20070155740A1 (en)	2007-07-05
PL366577A1 (en)	2005-02-07
YU90503A (sh)	2006-03-03
JP2004533447A (ja)	2004-11-04
BG108425A (en)	2004-12-30
NO20035055D0 (no)	2003-11-13
BR0209575A (pt)	2004-04-20
US7319100B2 (en)	2008-01-15
HK1059220A1 (en)	2004-06-25
CA2446980A1 (en)	2002-11-21
EP1392309A1 (en)	2004-03-03
WO2002092090A1 (en)	2002-11-21
RU2003135424A (ru)	2005-05-20
HUP0304048A2 (hu)	2004-04-28
DE60217669D1 (de)	2007-03-08
EP1392309B1 (en)	2007-01-17
MXPA03010324A (es)	2004-02-17
CN1527710A (zh)	2004-09-08
US20030171380A1 (en)	2003-09-11
KR20030094410A (ko)	2003-12-11

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