CA2608672A1 - Pyridine [3,4-b] pyrazinones - Google Patents

Pyridine [3,4-b] pyrazinones Download PDF

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Publication number: CA2608672A1
Authority: CA; Canada
Prior art keywords: group; pyrazin; pyrido; formula; alkyl
Prior art date: 2005-05-24
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

CA002608672A

Other languages

English (en)

Inventor

Alan George Benson

Andrew Simon Bell

David Graham Brown

David Louis Brown

Yvette Marlene Fobian

John Nicholas Freskos

Steven Edward Heasley

Robert Owen Hughes

Eric Jon Jacobsen

Brent Virgil Mischke

John Major Molyneaux

Dafydd Rhys Owen

Michael John Palmer

Christopher Phillips

Donald Joseph Rogier, Jr.

John Keith Walker

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pharmacia and Upjohn Co LLC

Original Assignee

Individual

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.)

2005-05-24

Filing date

2006-05-17

Publication date

2006-11-30

2006-05-17 Application filed by Individual filed Critical Individual

2006-11-30 Publication of CA2608672A1 publication Critical patent/CA2608672A1/fr

Status Withdrawn legal-status Critical Current

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HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical class OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 title claims description 32
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title description 6
229940123333 Phosphodiesterase 5 inhibitor Drugs 0.000 title description 2
239000002590 phosphodiesterase V inhibitor Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 190
238000000034 method Methods 0.000 claims abstract description 47
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
-1 hydroxy, carboxy Chemical group 0.000 claims description 303
125000000217 alkyl group Chemical group 0.000 claims description 192
239000001257 hydrogen Substances 0.000 claims description 186
229910052739 hydrogen Inorganic materials 0.000 claims description 186
125000001424 substituent group Chemical group 0.000 claims description 162
150000002431 hydrogen Chemical class 0.000 claims description 122
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 110
229910052736 halogen Inorganic materials 0.000 claims description 96
150000002367 halogens Chemical class 0.000 claims description 77
125000004043 oxo group Chemical group O=* 0.000 claims description 76
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 73
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 72
125000003545 alkoxy group Chemical group 0.000 claims description 56
125000004093 cyano group Chemical group *C#N 0.000 claims description 56
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 49
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 49
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 49
125000004076 pyridyl group Chemical group 0.000 claims description 49
125000000304 alkynyl group Chemical group 0.000 claims description 48
125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 48
125000003342 alkenyl group Chemical group 0.000 claims description 41
125000000623 heterocyclic group Chemical group 0.000 claims description 40
229920006395 saturated elastomer Polymers 0.000 claims description 39
125000001153 fluoro group Chemical group F* 0.000 claims description 37
125000004438 haloalkoxy group Chemical group 0.000 claims description 33
125000005111 carboxyalkoxy group Chemical group 0.000 claims description 27
125000000753 cycloalkyl group Chemical group 0.000 claims description 27
125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 27
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 25
125000004432 carbon atom Chemical group C* 0.000 claims description 21
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
125000003118 aryl group Chemical group 0.000 claims description 19
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
125000003386 piperidinyl group Chemical group 0.000 claims description 17
125000005843 halogen group Chemical group 0.000 claims description 16
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 15
125000000232 haloalkynyl group Chemical group 0.000 claims description 14
125000005016 hydroxyalkynyl group Chemical group 0.000 claims description 14
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 14
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
125000001309 chloro group Chemical group Cl* 0.000 claims description 9
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 8
125000002757 morpholinyl group Chemical group 0.000 claims description 8
125000004193 piperazinyl group Chemical group 0.000 claims description 8
201000001880 Sexual dysfunction Diseases 0.000 claims description 7
231100000872 sexual dysfunction Toxicity 0.000 claims description 7
208000024172 Cardiovascular disease Diseases 0.000 claims description 6
208000019693 Lung disease Diseases 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
208000015114 central nervous system disease Diseases 0.000 claims description 6
208000030159 metabolic disease Diseases 0.000 claims description 6
230000008085 renal dysfunction Effects 0.000 claims description 6
125000002393 azetidinyl group Chemical group 0.000 claims description 4
125000004069 aziridinyl group Chemical group 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
GQFFSMUOVRZLPX-UHFFFAOYSA-N 3-[[2-(4-ethylpiperazin-1-yl)-2-oxoethyl]amino]-7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC(=O)N1CCN(CC)CC1 GQFFSMUOVRZLPX-UHFFFAOYSA-N 0.000 claims description 3
OFRWMWHKNKWEHT-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-3-(2-morpholin-4-ylethylamino)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCCN1CCOCC1 OFRWMWHKNKWEHT-UHFFFAOYSA-N 0.000 claims description 3
OPMZGYYKMUWVJU-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-3-(piperidin-4-ylamino)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NC1CCNCC1 OPMZGYYKMUWVJU-UHFFFAOYSA-N 0.000 claims description 3
208000016097 disease of metabolism Diseases 0.000 claims description 3
JSGMYEYPLJHTMO-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-(2-morpholin-4-ylethylamino)-7-[4-(trifluoromethyl)phenyl]pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCC)C2=CC(C=3C=CC(=CC=3)C(F)(F)F)=NC=C2N=C1NCCN1CCOCC1 JSGMYEYPLJHTMO-UHFFFAOYSA-N 0.000 claims description 2
GQUAWNUFTFBENQ-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-(2-morpholin-4-ylethylamino)-7-phenylpyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCC)C2=CC(C=3C=CC=CC=3)=NC=C2N=C1NCCN1CCOCC1 GQUAWNUFTFBENQ-UHFFFAOYSA-N 0.000 claims description 2
JTJBMAKTNIJLON-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-(2-morpholin-4-ylethylamino)-7-pyridin-3-ylpyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCC)C2=CC(C=3C=NC=CC=3)=NC=C2N=C1NCCN1CCOCC1 JTJBMAKTNIJLON-UHFFFAOYSA-N 0.000 claims description 2
ZHQARHSBEHLEOM-UHFFFAOYSA-N 1-(2-ethoxyethyl)-7-(3-fluorophenyl)-3-(2-morpholin-4-ylethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCC)C2=CC(C=3C=C(F)C=CC=3)=NC=C2N=C1NCCN1CCOCC1 ZHQARHSBEHLEOM-UHFFFAOYSA-N 0.000 claims description 2
DDFJFVGZAFKJDM-UHFFFAOYSA-N 1-(2-ethoxyethyl)-7-(4-methoxyphenyl)-3-(2-morpholin-4-ylethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCC)C2=CC(C=3C=CC(OC)=CC=3)=NC=C2N=C1NCCN1CCOCC1 DDFJFVGZAFKJDM-UHFFFAOYSA-N 0.000 claims description 2
GMIVVTDZLPDQQL-UHFFFAOYSA-N 1-(2-ethoxyethyl)-7-(6-methoxypyridin-3-yl)-3-(2-morpholin-4-ylethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCCN1CCOCC1 GMIVVTDZLPDQQL-UHFFFAOYSA-N 0.000 claims description 2
TVMWWBMUZVMEMC-UHFFFAOYSA-N 1-(2-ethoxyethyl)-7-(6-methoxypyridin-3-yl)-3-(2-pyrrolidin-1-ylethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCCN1CCCC1 TVMWWBMUZVMEMC-UHFFFAOYSA-N 0.000 claims description 2
YKXFQRFNHFVELM-UHFFFAOYSA-N 1-(2-ethoxyethyl)-7-(6-methoxypyridin-3-yl)-3-(pyridin-2-ylmethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1=CC=CC=N1 YKXFQRFNHFVELM-UHFFFAOYSA-N 0.000 claims description 2
QNIXYGGRRVVDAJ-UHFFFAOYSA-N 1-(2-ethoxyethyl)-7-(6-methoxypyridin-3-yl)-3-[(2-morpholin-4-yl-2-oxoethyl)amino]pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC(=O)N1CCOCC1 QNIXYGGRRVVDAJ-UHFFFAOYSA-N 0.000 claims description 2
IJLBKMWJPBSPSR-INIZCTEOSA-N 1-(2-ethoxyethyl)-7-(6-methoxypyridin-3-yl)-3-[[(2s)-oxolan-2-yl]methylamino]pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NC[C@@H]1CCCO1 IJLBKMWJPBSPSR-INIZCTEOSA-N 0.000 claims description 2
FWBUXECRMROMDH-UHFFFAOYSA-N 1-(3-ethoxypropyl)-7-(6-methoxypyridin-3-yl)-3-(pyridin-2-ylmethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCCOCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1=CC=CC=N1 FWBUXECRMROMDH-UHFFFAOYSA-N 0.000 claims description 2
HVFUOSLJNRHNGH-UHFFFAOYSA-N 1-(3-ethoxypropyl)-7-(6-methoxypyridin-3-yl)-3-[(2-morpholin-4-yl-2-oxoethyl)amino]pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCCOCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC(=O)N1CCOCC1 HVFUOSLJNRHNGH-UHFFFAOYSA-N 0.000 claims description 2
SYAVQQIMTHFBBL-UHFFFAOYSA-N 1-(3-ethoxypropyl)-7-(6-methoxypyridin-3-yl)-3-[(5-methylpyrazin-2-yl)methylamino]pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCCOCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1=CN=C(C)C=N1 SYAVQQIMTHFBBL-UHFFFAOYSA-N 0.000 claims description 2
KDCOFLGLJLQPCQ-KRWDZBQOSA-N 1-(3-ethoxypropyl)-7-(6-methoxypyridin-3-yl)-3-[[(2s)-oxolan-2-yl]methylamino]pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCCOCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NC[C@@H]1CCCO1 KDCOFLGLJLQPCQ-KRWDZBQOSA-N 0.000 claims description 2
HSRDKHPLKDHLAC-UHFFFAOYSA-N 3-(2-morpholin-4-ylethylamino)-1-(2-propoxyethyl)-7-pyrimidin-5-ylpyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC=NC=3)=NC=C2N=C1NCCN1CCOCC1 HSRDKHPLKDHLAC-UHFFFAOYSA-N 0.000 claims description 2
RNGOEGWXBHOIFX-UHFFFAOYSA-N 3-[[2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]amino]-7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC(=O)N1CCC(O)CC1 RNGOEGWXBHOIFX-UHFFFAOYSA-N 0.000 claims description 2
VMMUROBWHZHNHR-UHFFFAOYSA-N 7-(1,3-benzodioxol-5-yl)-3-(2-morpholin-4-ylethylamino)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=C4OCOC4=CC=3)=NC=C2N=C1NCCN1CCOCC1 VMMUROBWHZHNHR-UHFFFAOYSA-N 0.000 claims description 2
SAAFIWLGTVESHU-UHFFFAOYSA-N 7-(3,4-difluorophenyl)-1-(2-ethoxyethyl)-3-(2-morpholin-4-ylethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCC)C2=CC(C=3C=C(F)C(F)=CC=3)=NC=C2N=C1NCCN1CCOCC1 SAAFIWLGTVESHU-UHFFFAOYSA-N 0.000 claims description 2
XKTQFRRTNZIPAG-UHFFFAOYSA-N 7-(3,5-dimethyl-1,2-oxazol-4-yl)-3-[(2-morpholin-4-yl-2-oxoethyl)amino]-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C3=C(ON=C3C)C)=NC=C2N=C1NCC(=O)N1CCOCC1 XKTQFRRTNZIPAG-UHFFFAOYSA-N 0.000 claims description 2
YPWMEKWSRIOVAN-UHFFFAOYSA-N 7-(4-fluorophenyl)-3-(2-morpholin-4-ylethylamino)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=CC(F)=CC=3)=NC=C2N=C1NCCN1CCOCC1 YPWMEKWSRIOVAN-UHFFFAOYSA-N 0.000 claims description 2
ZYHQEODROZFYKV-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)-3-(pyridin-2-ylmethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1=CC=CC=N1 ZYHQEODROZFYKV-UHFFFAOYSA-N 0.000 claims description 2
FBCKBEXNEZFACL-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-3-(2-morpholin-4-ylethylamino)-1-(2-propan-2-yloxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound C1=NC(OC)=CC=C1C(N=C1)=CC2=C1N=C(NCCN1CCOCC1)C(=O)N2CCOC(C)C FBCKBEXNEZFACL-UHFFFAOYSA-N 0.000 claims description 2
DHUJXUCRLGDIKU-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-3-(2-piperidin-1-ylethylamino)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCCN1CCCCC1 DHUJXUCRLGDIKU-UHFFFAOYSA-N 0.000 claims description 2
JRFAOIGBZSQPKT-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-3-(piperidin-4-ylmethylamino)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1CCNCC1 JRFAOIGBZSQPKT-UHFFFAOYSA-N 0.000 claims description 2
IAZOKMQVDLHWPI-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-3-[(2-morpholin-4-yl-2-oxoethyl)amino]-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC(=O)N1CCOCC1 IAZOKMQVDLHWPI-UHFFFAOYSA-N 0.000 claims description 2
CBYYNSKRRKXPFV-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-3-[(2-oxo-2-pyrrolidin-1-ylethyl)amino]-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC(=O)N1CCCC1 CBYYNSKRRKXPFV-UHFFFAOYSA-N 0.000 claims description 2
SJZRFHMTFMOIJR-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-3-[(5-methylpyrazin-2-yl)methylamino]-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1=CN=C(C)C=N1 SJZRFHMTFMOIJR-UHFFFAOYSA-N 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
OHNXOFZDPQLHFB-UHFFFAOYSA-N tert-butyl 4-[[[7-(6-methoxypyridin-3-yl)-2-oxo-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-3-yl]amino]methyl]piperidine-1-carboxylate Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1CCN(C(=O)OC(C)(C)C)CC1 OHNXOFZDPQLHFB-UHFFFAOYSA-N 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
SCYZYLBJXYIJQL-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-(2-morpholin-4-ylethylamino)-7-[3-(trifluoromethyl)phenyl]pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCC)C2=CC(C=3C=C(C=CC=3)C(F)(F)F)=NC=C2N=C1NCCN1CCOCC1 SCYZYLBJXYIJQL-UHFFFAOYSA-N 0.000 claims 1
JTAFTMLCVVBSHZ-UHFFFAOYSA-N 3-(3-imidazol-1-ylpropylamino)-7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCCCN1C=CN=C1 JTAFTMLCVVBSHZ-UHFFFAOYSA-N 0.000 claims 1
QDIQYFQPTWVPLK-IRXDYDNUSA-N 3-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound N=1C=C2N=C(N3[C@H]4C[C@H](NC4)C3)C(=O)N(CCOCCC)C2=CC=1C1=CC=C(OC)N=C1 QDIQYFQPTWVPLK-IRXDYDNUSA-N 0.000 claims 1
NHMHPUIEDXZRKZ-UHFFFAOYSA-N 7-(2,3-dihydro-1-benzofuran-5-yl)-1-(2-ethoxyethyl)-3-(2-morpholin-4-ylethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCC)C2=CC(C=3C=C4CCOC4=CC=3)=NC=C2N=C1NCCN1CCOCC1 NHMHPUIEDXZRKZ-UHFFFAOYSA-N 0.000 claims 1
NCCPPGYXWKAREW-UHFFFAOYSA-N 7-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(2-ethoxyethyl)-3-(2-morpholin-4-ylethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCC)C2=CC(C3=C(ON=C3C)C)=NC=C2N=C1NCCN1CCOCC1 NCCPPGYXWKAREW-UHFFFAOYSA-N 0.000 claims 1
FSMJCRREFXYLCK-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-1-(2-propan-2-yloxyethyl)-3-(pyridin-2-ylmethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound C1=NC(OC)=CC=C1C(N=C1)=CC2=C1N=C(NCC=1N=CC=CC=1)C(=O)N2CCOC(C)C FSMJCRREFXYLCK-UHFFFAOYSA-N 0.000 claims 1
JDKOACBPJUCCHU-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)-3-(2-pyridin-2-ylethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCCC1=CC=CC=N1 JDKOACBPJUCCHU-UHFFFAOYSA-N 0.000 claims 1
RYTGHGMOZMZRDP-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-3-(oxan-4-ylmethylamino)-1-(2-propan-2-yloxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound C1=NC(OC)=CC=C1C(N=C1)=CC2=C1N=C(NCC1CCOCC1)C(=O)N2CCOC(C)C RYTGHGMOZMZRDP-UHFFFAOYSA-N 0.000 claims 1
CUVVUOKAFMJIJW-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-3-(oxan-4-ylmethylamino)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1CCOCC1 CUVVUOKAFMJIJW-UHFFFAOYSA-N 0.000 claims 1
WQNRPUZSDCBDJG-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-3-(oxolan-2-ylmethylamino)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1CCCO1 WQNRPUZSDCBDJG-UHFFFAOYSA-N 0.000 claims 1
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239000012279 sodium borohydride Substances 0.000 description 1
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KLKBCNDBOVRQIJ-UHFFFAOYSA-N tert-butyl 4-(aminomethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CN)CC1 KLKBCNDBOVRQIJ-UHFFFAOYSA-N 0.000 description 1
QQWYQAQQADNEIC-PTNGSMBKSA-N tert-butyl [(e)-[cyano(phenyl)methylidene]amino] carbonate Chemical compound CC(C)(C)OC(=O)O\N=C(\C#N)C1=CC=CC=C1 QQWYQAQQADNEIC-PTNGSMBKSA-N 0.000 description 1
UXWVQHXKKOGTSY-UHFFFAOYSA-N tert-butyl phenyl carbonate Chemical compound CC(C)(C)OC(=O)OC1=CC=CC=C1 UXWVQHXKKOGTSY-UHFFFAOYSA-N 0.000 description 1
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125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
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229940124597 therapeutic agent Drugs 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
150000001467 thiazolidinediones Chemical class 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
125000002769 thiazolinyl group Chemical group 0.000 description 1
125000003777 thiepinyl group Chemical group 0.000 description 1
125000005032 thiofuranyl group Chemical group S1C(=CC=C1)* 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
239000012049 topical pharmaceutical composition Substances 0.000 description 1
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CMSGWTNRGKRWGS-NQIIRXRSSA-N torcetrapib Chemical compound COC(=O)N([C@H]1C[C@@H](CC)N(C2=CC=C(C=C21)C(F)(F)F)C(=O)OCC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CMSGWTNRGKRWGS-NQIIRXRSSA-N 0.000 description 1
229950004514 torcetrapib Drugs 0.000 description 1
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DLQYXUGCCKQSRJ-UHFFFAOYSA-N tris(furan-2-yl)phosphane Chemical compound C1=COC(P(C=2OC=CC=2)C=2OC=CC=2)=C1 DLQYXUGCCKQSRJ-UHFFFAOYSA-N 0.000 description 1
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SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 description 1
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150000003751 zinc Chemical class 0.000 description 1
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IAIDUHCBNLFXEF-MNEFBYGVSA-N zofenopril Chemical compound C([C@@H](C)C(=O)N1[C@@H](C[C@@H](C1)SC=1C=CC=CC=1)C(O)=O)SC(=O)C1=CC=CC=C1 IAIDUHCBNLFXEF-MNEFBYGVSA-N 0.000 description 1
FIKYECRHLXONOX-UHFFFAOYSA-N zolasartan Chemical compound CCCCC1=NC(Cl)=C(C(O)=O)N1CC1=CC=C(OC(=C2Br)C=3C(=CC=CC=3)C3=NNN=N3)C2=C1 FIKYECRHLXONOX-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Heart & Thoracic Surgery (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CA002608672A 2005-05-24 2006-05-17 Pyridine [3,4-b] pyrazinones Withdrawn CA2608672A1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US68413905P	2005-05-24	2005-05-24
US60/684,139		2005-05-24
PCT/IB2006/001387 WO2006126082A2 (fr)	2005-05-24	2006-05-17	Pyridine [3,4-b] pyrazinones

Publications (1)

Publication Number	Publication Date
CA2608672A1 true CA2608672A1 (fr)	2006-11-30

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CA002608672A Withdrawn CA2608672A1 (fr)	2005-05-24	2006-05-17	Pyridine [3,4-b] pyrazinones

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CA (1)	CA2608672A1 (fr)
WO (1)	WO2006126082A2 (fr)

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JP2016507551A (ja)	2013-02-13	2016-03-10	ファイザー・インク	ヘテロアリール置換ヘキサヒドロピラノ［３，４−ｄ］［１，３］チアジン−２−アミン化合物
US9233981B1 (en)	2013-02-15	2016-01-12	Pfizer Inc.	Substituted phenyl hexahydropyrano[3,4-d][1,3]thiazin-2-amine compounds
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KR20180078347A (ko)	2014-04-10	2018-07-09	화이자 인코포레이티드	2-아미노-6-메틸-4,4a,5,6-테트라히드로피라노[3,4-d][1,3]티아진-8a(8H)-일-1,3-티아졸-4-일 아미드
US10131669B2 (en)	2014-07-24	2018-11-20	Pfizer Inc.	Pyrazolopyrimidine compounds
HUE044040T2 (hu)	2014-08-06	2019-09-30	Pfizer	Imidazopiridazin vegyületek
EP3253755B1 (fr)	2015-02-03	2020-08-26	Pfizer Inc	Nouveaux pyridopyrazinediones cyclopropabenzofuranyl
TN2017000485A1 (en)	2015-06-17	2019-04-12	Pfizer	Tricyclic compounds and their use as phosphodiesterase inhibitors
EP3353182A1 (fr)	2015-09-24	2018-08-01	Pfizer Inc	Dérivés de tétrahydropyrano[3,4-d][1,3]oxazine et leur utilisation en tant qu'inhibiteurs de bace
JP2018531923A (ja)	2015-09-24	2018-11-01	ファイザー・インク	Ｎ−［２−（２−アミノ−６，６−二置換−４，４ａ，５，６−テトラヒドロピラノ［３，４−ｄ］［１，３］チアジン−８ａ（８Ｈ）−イル）−１，３−チアゾール−４−イル］アミド
JP2018534251A (ja)	2015-09-24	2018-11-22	ファイザー・インク	Ｂａｃｅ阻害剤として有用なｎ−［２−（３−アミノ−２，５−ジメチル−１，１−ジオキシド−５，６−ジヒドロ−２ｈ−１，２，４−チアジアジン−５−イル）−１，３−チアゾール−４−イル］アミド
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WO2019183636A1 (fr)	2018-03-23	2019-09-26	Pfizer Inc.	Dérivés azaspiro de pipérazine
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WO2002076954A1 (fr) *	2001-03-23	2002-10-03	Smithkline Beecham Corporation	Composes utiles en tant qu'inhibiteurs de kinase pour le traitement de maladies hyperproliferantes
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2006
- 2006-05-17 WO PCT/IB2006/001387 patent/WO2006126082A2/fr not_active Ceased
- 2006-05-17 CA CA002608672A patent/CA2608672A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
WO2006126082A3 (fr)	2007-01-25
WO2006126082A2 (fr)	2006-11-30

Publication	Publication Date	Title
AU2007242555B2 (en)	2010-12-16	Pyridine[3,4-b]pyrazinones
CA2608672A1 (fr)	2006-11-30	Pyridine [3,4-b] pyrazinones
WO2006126081A2 (fr)	2006-11-30	Pyridine [2,3-b] pyrazinones
WO2006126083A1 (fr)	2006-11-30	Composes de pyridine [3 , 4-b] pyrazinones utilises comme inhibiteurs de pde-5
US20100093713A1 (en)	2010-04-15	Beta-carbolines useful for treating inflammatory disease
AU2009318855A1 (en)	2010-05-27	Lactams as beta secretase inhibitors
JP7464526B2 (ja)	2024-04-09	４－ヒドロキシピペリジン誘導体およびユビキチン特異的プロテアーゼ１９（ｕｓｐ１９）の阻害剤としてのその使用
TW202122382A (zh)	2021-06-16	乙內醯脲衍生物
US7951801B2 (en)	2011-05-31	Beta-carbolines useful for treating inflammatory disease
WO2007020521A1 (fr)	2007-02-22	Pyridoyrazinones comme inhibiteurs de la pde-5
CA3121376A1 (fr)	2020-06-11	Composes pharmaceutiques et leur utilisation en tant qu'inhibiteurs de la protease 19 specifique de l'ubiquitine (usp19)
HK1133875B (en)	2013-09-13	Pyridine[3,4-b]pyrazinones

Legal Events

Date	Code	Title	Description
2007-11-16	EEER	Examination request
2007-11-20	AZWI	Withdrawn application