IL187484A - 2 - (heteroaryl-theo [2,3- b] pyridine-7-yl) phenoxy carboxamide and dicarboxamide, their pharmaceutical preparations, and their use in the preparation of drugs for the treatment of cell proliferative diseases - Google Patents

Info

Publication number

IL187484A

IL187484A IL187484A IL18748407A IL187484A IL 187484 A IL187484 A IL 187484A IL 187484 A IL187484 A IL 187484A IL 18748407 A IL18748407 A IL 18748407A IL 187484 A IL187484 A IL 187484A

Authority

IL

Israel

Prior art keywords

group

alkyl

thieno

pyridin

optionally substituted

Prior art date

2005-05-20

Links

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• -1 phenoxy carboxamide Chemical class 0.000 title claims description 176
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 25
• 201000010099 disease Diseases 0.000 title claims description 24
• 239000003814 drug Substances 0.000 title claims description 21
• 239000008194 pharmaceutical composition Substances 0.000 title claims 2
• 230000004663 cell proliferation Effects 0.000 title description 3
• 125000000217 alkyl group Chemical group 0.000 claims description 426
• 125000000623 heterocyclic group Chemical group 0.000 claims description 344
• 125000003118 aryl group Chemical group 0.000 claims description 252
• 150000001875 compounds Chemical class 0.000 claims description 244
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 162
• 125000001424 substituent group Chemical group 0.000 claims description 140
• 125000001072 heteroaryl group Chemical group 0.000 claims description 137
• 125000005843 halogen group Chemical group 0.000 claims description 126
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 122
• 125000003545 alkoxy group Chemical group 0.000 claims description 121
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 117
• 125000004432 carbon atom Chemical group C* 0.000 claims description 113
• 229910052736 halogen Inorganic materials 0.000 claims description 106
• 150000002367 halogens Chemical class 0.000 claims description 105
• 229910052739 hydrogen Inorganic materials 0.000 claims description 102
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 95
• 239000000203 mixture Substances 0.000 claims description 93
• WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 claims description 87
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 78
• 229910052757 nitrogen Inorganic materials 0.000 claims description 75
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 67
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 66
• 238000000034 method Methods 0.000 claims description 66
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 63
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 63
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 60
• 229920006395 saturated elastomer Polymers 0.000 claims description 60
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 53
• 125000004429 atom Chemical group 0.000 claims description 53
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
• 125000002837 carbocyclic group Chemical group 0.000 claims description 44
• 230000011664 signaling Effects 0.000 claims description 44
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 42
• 125000003342 alkenyl group Chemical group 0.000 claims description 39
• 125000002947 alkylene group Chemical group 0.000 claims description 38
• 229910052760 oxygen Inorganic materials 0.000 claims description 37
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 34
• 125000004414 alkyl thio group Chemical group 0.000 claims description 33
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 33
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 31
• 229910052717 sulfur Inorganic materials 0.000 claims description 29
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 28
• 125000000304 alkynyl group Chemical group 0.000 claims description 27
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
• 125000004953 trihalomethyl group Chemical group 0.000 claims description 27
• 108091008605 VEGF receptors Proteins 0.000 claims description 25
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 25
• 230000002401 inhibitory effect Effects 0.000 claims description 25
• 108091008603 HGF receptors Proteins 0.000 claims description 24
• 229910052799 carbon Inorganic materials 0.000 claims description 24
• 125000003386 piperidinyl group Chemical group 0.000 claims description 24
• 101000599004 Homo sapiens Olfactory receptor 3A1 Proteins 0.000 claims description 23
• 102100037784 Olfactory receptor 3A1 Human genes 0.000 claims description 23
• 102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 claims description 23
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 22
• 229910052731 fluorine Inorganic materials 0.000 claims description 22
• 125000006413 ring segment Chemical group 0.000 claims description 22
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 21
• 125000004193 piperazinyl group Chemical group 0.000 claims description 21
• 125000002393 azetidinyl group Chemical group 0.000 claims description 20
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 20
• 102000005962 receptors Human genes 0.000 claims description 20
• 108020003175 receptors Proteins 0.000 claims description 20
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 19
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 19
• GKTQKQTXHNUFSP-UHFFFAOYSA-N thieno[3,4-c]pyrrole-4,6-dione Chemical compound S1C=C2C(=O)NC(=O)C2=C1 GKTQKQTXHNUFSP-UHFFFAOYSA-N 0.000 claims description 19
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 18
• 125000001188 haloalkyl group Chemical group 0.000 claims description 18
• 125000005842 heteroatom Chemical group 0.000 claims description 18
• 125000004069 aziridinyl group Chemical group 0.000 claims description 17
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 16
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 16
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 14
• USQCUKQZXOWUDF-YWZLYKJASA-N 6-chloro-n-[(3s)-1-[(2s)-1-(4-methyl-5-oxo-1,4-diazepan-1-yl)-1-oxopropan-2-yl]-2-oxopyrrolidin-3-yl]naphthalene-2-sulfonamide Chemical compound O=C([C@@H](N1C([C@@H](NS(=O)(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CC1)=O)C)N1CCN(C)C(=O)CC1 USQCUKQZXOWUDF-YWZLYKJASA-N 0.000 claims description 14
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 14
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 14
• 125000002757 morpholinyl group Chemical group 0.000 claims description 14
• 125000004434 sulfur atom Chemical group 0.000 claims description 14
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 14
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 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 12
• 239000001257 hydrogen Substances 0.000 claims description 12
• 125000002883 imidazolyl group Chemical group 0.000 claims description 12
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 12
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 12
• 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 claims description 11
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 11
• 239000001301 oxygen Substances 0.000 claims description 11
• 230000002062 proliferating effect Effects 0.000 claims description 11
• 125000000335 thiazolyl group Chemical group 0.000 claims description 11
• 125000003282 alkyl amino group Chemical group 0.000 claims description 10
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
• 125000002619 bicyclic group Chemical group 0.000 claims description 10
• 125000002971 oxazolyl group Chemical group 0.000 claims description 10
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
• 150000003839 salts Chemical class 0.000 claims description 10
• 125000003107 substituted aryl group Chemical group 0.000 claims description 10
• 229940124597 therapeutic agent Drugs 0.000 claims description 10
• 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 9
• 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
• 229910052698 phosphorus Inorganic materials 0.000 claims description 9
• 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 claims description 8
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 8
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 8
• 125000004122 cyclic group Chemical group 0.000 claims description 8
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 8
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 8
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 8
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 7
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 7
• 125000002252 acyl group Chemical group 0.000 claims description 6
• 150000001408 amides Chemical class 0.000 claims description 6
• 125000003943 azolyl group Chemical group 0.000 claims description 6
• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 5
• CPSUAFUQJBJMPO-UHFFFAOYSA-N 2-phenylpropanediamide Chemical compound NC(=O)C(C(N)=O)C1=CC=CC=C1 CPSUAFUQJBJMPO-UHFFFAOYSA-N 0.000 claims description 4
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
• 125000002723 alicyclic group Chemical group 0.000 claims description 4
• 150000003973 alkyl amines Chemical class 0.000 claims description 4
• 125000001207 fluorophenyl group Chemical group 0.000 claims description 4
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 4
• 230000001225 therapeutic effect Effects 0.000 claims description 4
• LEXZOOBHELGMSY-UHFFFAOYSA-N 2-pyridin-3-ylpropanediamide Chemical compound NC(=O)C(C(N)=O)C1=CC=CN=C1 LEXZOOBHELGMSY-UHFFFAOYSA-N 0.000 claims description 3
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 3
• 241001465754 Metazoa Species 0.000 claims description 3
• YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 3
• DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 3
• 125000000732 arylene group Chemical group 0.000 claims description 3
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• 125000005549 heteroarylene group Chemical group 0.000 claims description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 2
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• FEHLGOYZDFFMND-UHFFFAOYSA-N cyclopropane-1,1-dicarboxamide Chemical compound NC(=O)C1(C(N)=O)CC1 FEHLGOYZDFFMND-UHFFFAOYSA-N 0.000 claims 9
• 229910014585 C2-Ce Inorganic materials 0.000 claims 7
• 102000027430 HGF receptors Human genes 0.000 claims 6
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
• XZOWIJDBQIHMFC-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O.CCCC(N)=O XZOWIJDBQIHMFC-UHFFFAOYSA-N 0.000 claims 3
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
• YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims 2
• ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims 2
• IQHXABCGSFAKPN-UHFFFAOYSA-N pyrrolidine-3-carboxamide Chemical compound NC(=O)C1CCNC1 IQHXABCGSFAKPN-UHFFFAOYSA-N 0.000 claims 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
• OYOYNTSZERVIQZ-UHFFFAOYSA-N 2-piperidin-4-ylpropanediamide Chemical compound NC(=O)C(C(N)=O)C1CCNCC1 OYOYNTSZERVIQZ-UHFFFAOYSA-N 0.000 claims 1
• NUPSTLJOGDSEDG-UHFFFAOYSA-N 3-cyclohexyl-n-[3-fluoro-4-[2-(1-methylimidazol-4-yl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]-2-oxoimidazolidine-1-carboxamide Chemical compound CN1C=NC(C=2SC3=C(OC=4C(=CC(NC(=O)N5C(N(C6CCCCC6)CC5)=O)=CC=4)F)C=CN=C3C=2)=C1 NUPSTLJOGDSEDG-UHFFFAOYSA-N 0.000 claims 1
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
• DQRXNPIGWYMKBX-UHFFFAOYSA-N 7-(4-amino-2-fluorophenoxy)-n-(3-methoxyphenyl)thieno[3,2-b]pyridin-2-amine Chemical compound COC1=CC=CC(NC=2SC3=C(OC=4C(=CC(N)=CC=4)F)C=CN=C3C=2)=C1 DQRXNPIGWYMKBX-UHFFFAOYSA-N 0.000 claims 1
• 101100134925 Gallus gallus COR6 gene Proteins 0.000 claims 1
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• BWDJXPQOTCXSQC-UHFFFAOYSA-N N'-[3-fluoro-4-[2-(3-hydroxyazetidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]-N'-(2-methoxyphenyl)propanediamide Chemical compound FC=1C=C(C=CC1OC1=C2C(=NC=C1)C=C(S2)C(=O)N2CC(C2)O)N(C(CC(=O)N)=O)C2=C(C=CC=C2)OC BWDJXPQOTCXSQC-UHFFFAOYSA-N 0.000 claims 1
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• BSEXNZMHLUMQKR-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1.NC(=O)C1CC1 BSEXNZMHLUMQKR-UHFFFAOYSA-N 0.000 claims 1
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
• NTFOMPCTOJCWEK-UHFFFAOYSA-N imidazolidine-1-carboxamide Chemical compound NC(=O)N1CCNC1 NTFOMPCTOJCWEK-UHFFFAOYSA-N 0.000 claims 1
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• PUBLBUWIHAWTIR-UHFFFAOYSA-N n-[4-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]sulfanylphenyl]-2-oxo-3-phenylimidazolidine-1-carboxamide Chemical compound CN1C=CN=C1C1=CC2=NC=CC(SC=3C=CC(NC(=O)N4C(N(CC4)C=4C=CC=CC=4)=O)=CC=3)=C2S1 PUBLBUWIHAWTIR-UHFFFAOYSA-N 0.000 claims 1
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