TW200815407A - Substituted 3-cyanopyridines as protein kinase inhibitors - Google Patents

Info

Publication number

TW200815407A

TW200815407A TW096121311A TW96121311A TW200815407A TW 200815407 A TW200815407 A TW 200815407A TW 096121311 A TW096121311 A TW 096121311A TW 96121311 A TW96121311 A TW 96121311A TW 200815407 A TW200815407 A TW 200815407A

Authority

TW

Taiwan

Prior art keywords

methyl

amino

ylamino

phenyl

indol

Prior art date

2006-06-13

Links

• Espacenet
• Global Dossier
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• GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical class N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 title claims description 587
• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title 1
• 239000003909 protein kinase inhibitor Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 217
• 150000003839 salts Chemical class 0.000 claims abstract description 44
• 150000002148 esters Chemical class 0.000 claims abstract description 33
• 241000124008 Mammalia Species 0.000 claims abstract description 11
• 150000004677 hydrates Chemical class 0.000 claims abstract description 10
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 776
• -1 benzo[c]thienyl Chemical group 0.000 claims description 516
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 401
• 150000002825 nitriles Chemical class 0.000 claims description 359
• 239000002253 acid Substances 0.000 claims description 313
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 176
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 165
• 125000000217 alkyl group Chemical group 0.000 claims description 92
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 63
• 125000001072 heteroaryl group Chemical group 0.000 claims description 61
• 150000001412 amines Chemical class 0.000 claims description 50
• 125000003118 aryl group Chemical group 0.000 claims description 48
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 42
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 37
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 36
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 35
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 35
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 25
• VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 claims description 24
• 125000001041 indolyl group Chemical group 0.000 claims description 24
• 235000001968 nicotinic acid Nutrition 0.000 claims description 24
• 239000011664 nicotinic acid Substances 0.000 claims description 24
• 229960003512 nicotinic acid Drugs 0.000 claims description 24
• 125000000304 alkynyl group Chemical group 0.000 claims description 21
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 19
• 125000003277 amino group Chemical group 0.000 claims description 19
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
• 125000003342 alkenyl group Chemical group 0.000 claims description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
• 201000010099 disease Diseases 0.000 claims description 17
• 125000001188 haloalkyl group Chemical group 0.000 claims description 17
• 108090000315 Protein Kinase C Proteins 0.000 claims description 16
• 102000003923 Protein Kinase C Human genes 0.000 claims description 16
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 15
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 14
• 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 14
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
• 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 13
• 229920006391 phthalonitrile polymer Polymers 0.000 claims description 13
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 12
• 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 description 12
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
• 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
• LUQVCHRDAGWYMG-UHFFFAOYSA-N 4-phenylbenzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CC=CC=C1 LUQVCHRDAGWYMG-UHFFFAOYSA-N 0.000 claims description 11
• 206010003246 arthritis Diseases 0.000 claims description 11
• 229940079593 drug Drugs 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 125000000623 heterocyclic group Chemical group 0.000 claims description 11
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 11
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 11
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 10
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 10
• 150000002367 halogens Chemical class 0.000 claims description 10
• 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 10
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 10
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 9
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 9
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 9
• 125000005843 halogen group Chemical group 0.000 claims description 9
• 125000004076 pyridyl group Chemical group 0.000 claims description 9
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
• 102000001253 Protein Kinase Human genes 0.000 claims description 8
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
• 239000004305 biphenyl Substances 0.000 claims description 8
• 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims description 8
• 230000001575 pathological effect Effects 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• 125000003367 polycyclic group Chemical group 0.000 claims description 8
• 108060006633 protein kinase Proteins 0.000 claims description 8
• 239000000126 substance Substances 0.000 claims description 8
• 235000021419 vinegar Nutrition 0.000 claims description 8
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 7
• 208000006673 asthma Diseases 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• 125000005842 heteroatom Chemical group 0.000 claims description 7
• 230000001404 mediated effect Effects 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• 239000005711 Benzoic acid Substances 0.000 claims description 6
• LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 6
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
• 235000010233 benzoic acid Nutrition 0.000 claims description 6
• 235000010290 biphenyl Nutrition 0.000 claims description 6
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 208000024891 symptom Diseases 0.000 claims description 6
• 239000000052 vinegar Substances 0.000 claims description 6
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• XNLNVPMNYUHAIL-UHFFFAOYSA-N 5-pyridin-3-ylpyridine-3-carbonitrile Chemical compound N#CC1=CN=CC(C=2C=NC=CC=2)=C1 XNLNVPMNYUHAIL-UHFFFAOYSA-N 0.000 claims description 5
• 125000005605 benzo group Chemical group 0.000 claims description 5
• 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 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• 125000002971 oxazolyl group Chemical group 0.000 claims description 5
• 125000003386 piperidinyl group Chemical group 0.000 claims description 5
• 150000003573 thiols Chemical class 0.000 claims description 5
• 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims description 4
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 4
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
• 201000004681 Psoriasis Diseases 0.000 claims description 4
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
• 206010009887 colitis Diseases 0.000 claims description 4
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 4
• 230000005764 inhibitory process Effects 0.000 claims description 4
• 208000018937 joint inflammation Diseases 0.000 claims description 4
• 201000006417 multiple sclerosis Diseases 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 201000008482 osteoarthritis Diseases 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 150000003254 radicals Chemical class 0.000 claims description 4
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 4
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
• 229930192474 thiophene Natural products 0.000 claims description 4
• MLLWIGIVPMMGQD-UHFFFAOYSA-N 2-(1h-indol-5-ylamino)pyridine-3-carbonitrile Chemical compound N#CC1=CC=CN=C1NC1=CC=C(NC=C2)C2=C1 MLLWIGIVPMMGQD-UHFFFAOYSA-N 0.000 claims description 3
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
• MKKNTDWMTBRGCD-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)pyridine-3-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN=CC(C(O)=O)=C1 MKKNTDWMTBRGCD-UHFFFAOYSA-N 0.000 claims description 3
• 241000009298 Trigla lyra Species 0.000 claims description 3
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
• 230000002378 acidificating effect Effects 0.000 claims description 3
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 3
• 125000006309 butyl amino group Chemical group 0.000 claims description 3
• 239000004202 carbamide Substances 0.000 claims description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000006317 cyclopropyl amino group Chemical group 0.000 claims description 3
• 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 claims description 3
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
• 125000002757 morpholinyl group Chemical group 0.000 claims description 3
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
• HPARLNRMYDSBNO-UHFFFAOYSA-N 1,4-benzodioxine Chemical compound C1=CC=C2OC=COC2=C1 HPARLNRMYDSBNO-UHFFFAOYSA-N 0.000 claims description 2
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 2
• RQSCFNPNNLWQBJ-UHFFFAOYSA-N 2-methyl-1,3,4-thiadiazole Chemical compound CC1=NN=CS1 RQSCFNPNNLWQBJ-UHFFFAOYSA-N 0.000 claims description 2
• XNLWJFYYOIRPIO-UHFFFAOYSA-N 3-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1 XNLWJFYYOIRPIO-UHFFFAOYSA-N 0.000 claims description 2
• 229940123208 Biguanide Drugs 0.000 claims description 2
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
• METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 2
• 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
• JVXNCJLLOUQYBF-UHFFFAOYSA-N cyclohex-4-ene-1,3-dione Chemical compound O=C1CC=CC(=O)C1 JVXNCJLLOUQYBF-UHFFFAOYSA-N 0.000 claims description 2
• QPMLSUSACCOBDK-UHFFFAOYSA-N diazepane Chemical compound C1CCNNCC1 QPMLSUSACCOBDK-UHFFFAOYSA-N 0.000 claims description 2
• UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims description 2
• 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 2
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 2
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
• 235000013336 milk Nutrition 0.000 claims description 2
• 239000008267 milk Substances 0.000 claims description 2
• 210000004080 milk Anatomy 0.000 claims description 2
• 230000007170 pathology Effects 0.000 claims description 2
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 2
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 2
• 125000005493 quinolyl group Chemical group 0.000 claims description 2
• 230000001568 sexual effect Effects 0.000 claims description 2
• 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
• 239000008096 xylene Substances 0.000 claims description 2
• ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 claims 6
• DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims 4
• QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 2
• IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims 2
• GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims 2
• 229940005561 1,4-benzoquinone Drugs 0.000 claims 1
• XYUPPXPJWYLXSW-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=C[CH]C2=C=COC2=C1 XYUPPXPJWYLXSW-UHFFFAOYSA-N 0.000 claims 1
• KZNJSFHJUQDYHE-UHFFFAOYSA-N 1-methylanthracene Chemical compound C1=CC=C2C=C3C(C)=CC=CC3=CC2=C1 KZNJSFHJUQDYHE-UHFFFAOYSA-N 0.000 claims 1
• BLRHMMGNCXNXJL-UHFFFAOYSA-N 1-methylindole Chemical compound C1=CC=C2N(C)C=CC2=C1 BLRHMMGNCXNXJL-UHFFFAOYSA-N 0.000 claims 1
• FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical group CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 claims 1
• LYIUZNSEZMKOQV-UHFFFAOYSA-N 2-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=NC=CC=C1C#N LYIUZNSEZMKOQV-UHFFFAOYSA-N 0.000 claims 1
• YYXDQRRDNPRJFL-UHFFFAOYSA-N 2-aminopyridine-3-carbonitrile Chemical compound NC1=NC=CC=C1C#N YYXDQRRDNPRJFL-UHFFFAOYSA-N 0.000 claims 1
• SOFPIAMTOZWXKT-UHFFFAOYSA-N 2h-1,2,4-triazine-3-thione Chemical compound SC1=NC=CN=N1 SOFPIAMTOZWXKT-UHFFFAOYSA-N 0.000 claims 1
• LNVWRBNPXCUYJI-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazol-4-amine Chemical compound CC1=NNC(C)=C1N LNVWRBNPXCUYJI-UHFFFAOYSA-N 0.000 claims 1
• 125000001963 4 membered heterocyclic group Chemical group 0.000 claims 1
• YUWKEVJEMKKVGQ-UHFFFAOYSA-N 4-bromo-1h-pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC(Br)=CN1 YUWKEVJEMKKVGQ-UHFFFAOYSA-N 0.000 claims 1
• YCAXSFSUHXSJNU-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-4-[(4-methyl-1h-indol-7-yl)amino]pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=C(C)C2=C1NC=C2 YCAXSFSUHXSJNU-UHFFFAOYSA-N 0.000 claims 1
• JBACXOGAOBGKOL-UHFFFAOYSA-N 5-[4-methoxy-3-(2-methoxyethoxy)phenyl]-4-[(2-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OCCOC)=CC(C=2C(=C(C#N)C=NC=2)NC=2C=C3C=C(C)NC3=CC=2)=C1 JBACXOGAOBGKOL-UHFFFAOYSA-N 0.000 claims 1
• IHIJGMGZNYFVMD-UHFFFAOYSA-N 5-[6-[3-(dimethylamino)propoxy]pyridin-3-yl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=NC(OCCCN(C)C)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C IHIJGMGZNYFVMD-UHFFFAOYSA-N 0.000 claims 1
• WJRFOSBCACMRMM-UHFFFAOYSA-N 9H-fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1.C1=CC=C2CC3=CC=CC=C3C2=C1 WJRFOSBCACMRMM-UHFFFAOYSA-N 0.000 claims 1
• PIIXUVWJQUGIHG-WKILWMFISA-N C1=C(OC)C(OC)=CC=C1C1=CN=CC(C#N)=C1N[C@@H]1CC[C@@H](N)CC1 Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN=CC(C#N)=C1N[C@@H]1CC[C@@H](N)CC1 PIIXUVWJQUGIHG-WKILWMFISA-N 0.000 claims 1
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