NO327466B1 - Indol-2-karboksamider, fremgangsmate for fremstilling, et farmasoytisk preparat omfattende disse, samt deres anvendelse - Google Patents

Info

Publication number

NO327466B1

NO327466B1 NO20042592A NO20042592A NO327466B1 NO 327466 B1 NO327466 B1 NO 327466B1 NO 20042592 A NO20042592 A NO 20042592A NO 20042592 A NO20042592 A NO 20042592A NO 327466 B1 NO327466 B1 NO 327466B1

Authority

NO

Norway

Prior art keywords

chloro

carboxylic acid

piperidin

indole

ylmethyl

Prior art date

2001-11-22

Links

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• 238000000034 method Methods 0.000 title claims description 82
• 230000008569 process Effects 0.000 title claims description 6
• 238000002360 preparation method Methods 0.000 title description 30
• VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical class C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 title 1
• 239000008194 pharmaceutical composition Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 315
• 239000000460 chlorine Substances 0.000 claims description 183
• 229910052801 chlorine Inorganic materials 0.000 claims description 181
• -1 phenylpyridyl Chemical group 0.000 claims description 141
• 239000000203 mixture Substances 0.000 claims description 92
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 68
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 62
• 125000000217 alkyl group Chemical group 0.000 claims description 49
• 150000003839 salts Chemical class 0.000 claims description 43
• 125000001072 heteroaryl group Chemical group 0.000 claims description 41
• 239000001257 hydrogen Substances 0.000 claims description 40
• 229910052739 hydrogen Inorganic materials 0.000 claims description 40
• 150000002367 halogens Chemical class 0.000 claims description 37
• 229910052736 halogen Inorganic materials 0.000 claims description 36
• 108010074860 Factor Xa Proteins 0.000 claims description 34
• ZRQQXFMGYSOKDF-UHFFFAOYSA-N 1-propan-2-ylpiperidin-4-amine Chemical compound CC(C)N1CCC(N)CC1 ZRQQXFMGYSOKDF-UHFFFAOYSA-N 0.000 claims description 33
• 125000004122 cyclic group Chemical group 0.000 claims description 32
• 230000015572 biosynthetic process Effects 0.000 claims description 29
• RASORPKPULRQAN-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-[(1-pyridin-4-ylpiperidin-4-yl)methyl]indole-2-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3C=C2C(=O)NCC2CCN(CC2)C=2C=CN=CC=2)=NO1 RASORPKPULRQAN-UHFFFAOYSA-N 0.000 claims description 26
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 26
• RJCRRLMFYIXJAH-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]indole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=CC=CC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 RJCRRLMFYIXJAH-UHFFFAOYSA-N 0.000 claims description 24
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 22
• 125000002950 monocyclic group Chemical group 0.000 claims description 20
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
• 125000001041 indolyl group Chemical group 0.000 claims description 17
• 125000003386 piperidinyl group Chemical group 0.000 claims description 15
• OEACEEHJARIXJW-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indole-5-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC(C(O)=O)=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 OEACEEHJARIXJW-UHFFFAOYSA-N 0.000 claims description 14
• 229910052794 bromium Inorganic materials 0.000 claims description 14
• 229910052731 fluorine Inorganic materials 0.000 claims description 14
• 125000000524 functional group Chemical group 0.000 claims description 14
• 150000002431 hydrogen Chemical class 0.000 claims description 14
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 14
• 125000004076 pyridyl group Chemical group 0.000 claims description 14
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 13
• 238000002560 therapeutic procedure Methods 0.000 claims description 13
• 125000000335 thiazolyl group Chemical group 0.000 claims description 13
• 125000002619 bicyclic group Chemical group 0.000 claims description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
• 230000023555 blood coagulation Effects 0.000 claims description 11
• 150000002148 esters Chemical class 0.000 claims description 11
• 230000002401 inhibitory effect Effects 0.000 claims description 11
• 125000004193 piperazinyl group Chemical group 0.000 claims description 11
• 208000007536 Thrombosis Diseases 0.000 claims description 10
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 10
• 239000002243 precursor Substances 0.000 claims description 10
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
• 239000003146 anticoagulant agent Substances 0.000 claims description 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 9
• DQJGJGNWFRPEHZ-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indole-4-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=C(C(O)=O)C=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 DQJGJGNWFRPEHZ-UHFFFAOYSA-N 0.000 claims description 8
• ZFCKJGACJXTSOI-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-7-methylindole-2-carboxylic acid Chemical compound C1=2C(C)=CC=CC=2C=C(C(O)=O)N1CC(=NO1)C=C1C1=CC=C(Cl)S1 ZFCKJGACJXTSOI-UHFFFAOYSA-N 0.000 claims description 8
• MMGXOGPDBICRQF-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical group C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 MMGXOGPDBICRQF-UHFFFAOYSA-N 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• 125000002883 imidazolyl group Chemical group 0.000 claims description 8
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 8
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 8
• 208000001435 Thromboembolism Diseases 0.000 claims description 7
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
• 125000002843 carboxylic acid 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
• 229910052740 iodine Inorganic materials 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• KBXWLAQHWUNMMX-UHFFFAOYSA-N 1-(4-methoxyphenyl)indole-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1N1C2=CC=CC=C2C=C1C(O)=O KBXWLAQHWUNMMX-UHFFFAOYSA-N 0.000 claims description 6
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 6
• 230000020764 fibrinolysis Effects 0.000 claims description 6
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 6
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 6
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
• 238000001356 surgical procedure Methods 0.000 claims description 6
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 230000002792 vascular Effects 0.000 claims description 6
• UQUFONQTPPAJAO-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C2=CC=CC=C2C=C1C(=O)NC1CCN(C(C)C)CC1 UQUFONQTPPAJAO-UHFFFAOYSA-N 0.000 claims description 5
• DLMIMIWKEZCOGZ-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)ethyl]-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC=CC=C2N1CCC1=CC=C(Cl)C=C1Cl DLMIMIWKEZCOGZ-UHFFFAOYSA-N 0.000 claims description 5
• FWLFQJFZPDIYBO-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-3,7-diiodo-4-methoxy-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=C(I)C=2C(OC)=CC=C(I)C=2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 FWLFQJFZPDIYBO-UHFFFAOYSA-N 0.000 claims description 5
• OYIDOIKTXHNHIG-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-[(1-propan-2-ylpiperidin-4-yl)methyl]indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1CNC(=O)C1=CC2=CC=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 OYIDOIKTXHNHIG-UHFFFAOYSA-N 0.000 claims description 5
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 5
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
• MGMRQNKJMRCNMF-UHFFFAOYSA-N [1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]indol-2-yl]-[4-(pyridin-4-ylamino)piperidin-1-yl]methanone Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3C=C2C(=O)N2CCC(CC2)NC=2C=CN=CC=2)=NO1 MGMRQNKJMRCNMF-UHFFFAOYSA-N 0.000 claims description 5
• 230000001154 acute effect Effects 0.000 claims description 5
• 238000009833 condensation Methods 0.000 claims description 5
• 230000005494 condensation Effects 0.000 claims description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
• 208000037803 restenosis Diseases 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• 239000011593 sulfur Chemical group 0.000 claims description 5
• BYYGHUVCRZUIRW-UHFFFAOYSA-N 1-(2,2-dimethylpropanoyloxy)ethyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indole-5-carboxylate Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC(C(=O)OC(C)OC(=O)C(C)(C)C)=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 BYYGHUVCRZUIRW-UHFFFAOYSA-N 0.000 claims description 4
• PFJWZQPHCQIIKR-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC=CC=C2N1C1=CC(Cl)=CC(Cl)=C1 PFJWZQPHCQIIKR-UHFFFAOYSA-N 0.000 claims description 4
• CRPZABPLZRHXOL-UHFFFAOYSA-N 1-(3-methoxybenzoyl)-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound COC1=CC=CC(C(=O)N2C3=CC=CC=C3C=C2C(=O)NC2CCN(CC2)C(C)C)=C1 CRPZABPLZRHXOL-UHFFFAOYSA-N 0.000 claims description 4
• PJTYIXSRDGSRKB-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC=CC=C2N1C1=CC=C(Cl)C=C1 PJTYIXSRDGSRKB-UHFFFAOYSA-N 0.000 claims description 4
• PVDKWERHFVOLOH-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC=CC=C2N1CC1=CC=CC=C1Cl PVDKWERHFVOLOH-UHFFFAOYSA-N 0.000 claims description 4
• XYPXJXNGUNXJSO-UHFFFAOYSA-N 1-[(3,5-dichlorophenyl)methyl]-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC=CC=C2N1CC1=CC(Cl)=CC(Cl)=C1 XYPXJXNGUNXJSO-UHFFFAOYSA-N 0.000 claims description 4
• BWFWPGPBRJZFKC-UHFFFAOYSA-N 1-[(3-methoxyphenyl)methyl]-5-methyl-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound COC1=CC=CC(CN2C3=CC=C(C)C=C3C=C2C(=O)NC2CCN(CC2)C(C)C)=C1 BWFWPGPBRJZFKC-UHFFFAOYSA-N 0.000 claims description 4
• BZQFXVVHJMEYGC-UHFFFAOYSA-N 1-[(3-methoxyphenyl)methyl]-5-phenylmethoxy-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound COC1=CC=CC(CN2C3=CC=C(OCC=4C=CC=CC=4)C=C3C=C2C(=O)NC2CCN(CC2)C(C)C)=C1 BZQFXVVHJMEYGC-UHFFFAOYSA-N 0.000 claims description 4
• PQDRFBZXRKOETO-UHFFFAOYSA-N 1-[(6-chloro-1-benzothiophen-2-yl)methyl]-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC=CC=C2N1CC1=CC2=CC=C(Cl)C=C2S1 PQDRFBZXRKOETO-UHFFFAOYSA-N 0.000 claims description 4
• DSBLCMAHBANTAE-UHFFFAOYSA-N 1-[2-(3-methoxyphenyl)ethyl]indole-2-carboxylic acid Chemical compound COC1=CC=CC(CCN2C3=CC=CC=C3C=C2C(O)=O)=C1 DSBLCMAHBANTAE-UHFFFAOYSA-N 0.000 claims description 4
• TUJRINRCZRSTKI-UHFFFAOYSA-N 1-[2-(4-chloro-2-fluoroanilino)-2-oxoethyl]-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC=CC=C2N1CC(=O)NC1=CC=C(Cl)C=C1F TUJRINRCZRSTKI-UHFFFAOYSA-N 0.000 claims description 4
• XMBHXMWOQCBVDD-UHFFFAOYSA-N 1-[2-(4-chloroanilino)-2-oxoethyl]-5-nitro-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC([N+]([O-])=O)=CC=C2N1CC(=O)NC1=CC=C(Cl)C=C1 XMBHXMWOQCBVDD-UHFFFAOYSA-N 0.000 claims description 4
• RPXARQCXLPPUMJ-UHFFFAOYSA-N 1-[2-(4-chloroanilino)-2-oxoethyl]-n-[(1-pyridin-4-ylpiperidin-4-yl)methyl]indole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)CN1C2=CC=CC=C2C=C1C(=O)NCC1CCN(C=2C=CN=CC=2)CC1 RPXARQCXLPPUMJ-UHFFFAOYSA-N 0.000 claims description 4
• AXJHGZQKOZQHQC-UHFFFAOYSA-N 1-[2-(4-chloroanilino)-2-oxoethyl]indole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=CC=CC=C2N1CC(=O)NC1=CC=C(Cl)C=C1 AXJHGZQKOZQHQC-UHFFFAOYSA-N 0.000 claims description 4
• LBQLDTXJHMXFGR-UHFFFAOYSA-N 1-[2-[(5-chlorothiophen-2-yl)amino]-2-oxoethyl]-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC=CC=C2N1CC(=O)NC1=CC=C(Cl)S1 LBQLDTXJHMXFGR-UHFFFAOYSA-N 0.000 claims description 4
• VBPAXWNURRSMSW-UHFFFAOYSA-N 1-[[3-(5-chlorothiophen-2-yl)-1,2-oxazol-5-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC=CC=C2N1CC1=CC(C=2SC(Cl)=CC=2)=NO1 VBPAXWNURRSMSW-UHFFFAOYSA-N 0.000 claims description 4
• YNGBTQWWOMFMNU-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-3-cyano-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=C(C#N)C2=CC=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 YNGBTQWWOMFMNU-UHFFFAOYSA-N 0.000 claims description 4
• KPIQURKZNMPNNM-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-3-fluoro-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=C(F)C2=CC=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 KPIQURKZNMPNNM-UHFFFAOYSA-N 0.000 claims description 4
• QJEVVAJVLUWEQH-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4,7-dimethoxy-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC=2C(OC)=CC=C(OC)C=2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 QJEVVAJVLUWEQH-UHFFFAOYSA-N 0.000 claims description 4
• XDHLEMSKBSBEDC-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-cyclopropylpiperidin-4-yl)indole-2-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3C=C2C(=O)NC2CCN(CC2)C2CC2)=NO1 XDHLEMSKBSBEDC-UHFFFAOYSA-N 0.000 claims description 4
• GZYLKYFEFKEDRG-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-methylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1CN(C)CCC1NC(=O)C1=CC2=CC=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 GZYLKYFEFKEDRG-UHFFFAOYSA-N 0.000 claims description 4
• WKYZTNUDHMDOAY-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1CN(CCC)CCC1NC(=O)C1=CC2=CC=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 WKYZTNUDHMDOAY-UHFFFAOYSA-N 0.000 claims description 4
• CNGMHTSQLMODBT-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(4-ethylpiperazin-1-yl)indole-2-carboxamide Chemical compound C1CN(CC)CCN1NC(=O)C1=CC2=CC=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 CNGMHTSQLMODBT-UHFFFAOYSA-N 0.000 claims description 4
• GJUUXHXBHXTVKN-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(4-methylpiperazin-1-yl)indole-2-carboxamide Chemical compound C1CN(C)CCN1NC(=O)C1=CC2=CC=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 GJUUXHXBHXTVKN-UHFFFAOYSA-N 0.000 claims description 4
• YXKCQZAYGJLSQA-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(4-propan-2-ylpiperazin-1-yl)indole-2-carboxamide Chemical compound C1CN(C(C)C)CCN1NC(=O)C1=CC2=CC=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 YXKCQZAYGJLSQA-UHFFFAOYSA-N 0.000 claims description 4
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