CA3046805A1 - Spiropiperidine derivatives - Google Patents

Info

Publication number

CA3046805A1

CA3046805A1 CA3046805A CA3046805A CA3046805A1 CA 3046805 A1 CA3046805 A1 CA 3046805A1 CA 3046805 A CA3046805 A CA 3046805A CA 3046805 A CA3046805 A CA 3046805A CA 3046805 A1 CA3046805 A1 CA 3046805A1

Authority

CA

Canada

Prior art keywords

spiro

carboxamide

piperidine

chromane

quinolyl

Prior art date

2016-12-14

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.)

Pending

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• JUXAVSAMVBLDKO-UHFFFAOYSA-N 1-(1-azabicyclo[2.2.2]octan-3-yl)-3-[3-(1h-indol-3-yl)-1-oxo-1-spiro[1,2-dihydroindene-3,4'-piperidine]-1'-ylpropan-2-yl]urea Chemical class C1N(CC2)CCC2C1NC(=O)NC(C(=O)N1CCC2(C3=CC=CC=C3CC2)CC1)CC1=CNC2=CC=CC=C12 JUXAVSAMVBLDKO-UHFFFAOYSA-N 0.000 title abstract description 11
• 150000001875 compounds Chemical class 0.000 claims abstract description 310
• 238000000034 method Methods 0.000 claims abstract description 84
• 102000015303 Fatty Acid Synthases Human genes 0.000 claims abstract description 51
• 108010039731 Fatty Acid Synthases Proteins 0.000 claims abstract description 51
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 40
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
• 230000001404 mediated effect Effects 0.000 claims abstract description 14
• 125000003003 spiro group Chemical group 0.000 claims description 420
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 290
• -1 substituted Chemical class 0.000 claims description 238
• 125000001183 hydrocarbyl group Chemical group 0.000 claims description 145
• 229910052736 halogen Inorganic materials 0.000 claims description 124
• 150000002367 halogens Chemical class 0.000 claims description 124
• 125000000623 heterocyclic group Chemical group 0.000 claims description 119
• 239000002253 acid Substances 0.000 claims description 72
• 125000001072 heteroaryl group Chemical group 0.000 claims description 62
• 125000000217 alkyl group Chemical group 0.000 claims description 59
• 229910052757 nitrogen Inorganic materials 0.000 claims description 54
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 52
• 150000003839 salts Chemical class 0.000 claims description 51
• 125000001624 naphthyl group Chemical group 0.000 claims description 47
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 44
• 229910052717 sulfur Inorganic materials 0.000 claims description 33
• 125000003386 piperidinyl group Chemical group 0.000 claims description 31
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
• 125000003118 aryl group Chemical group 0.000 claims description 15
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
• 208000021017 Weight Gain Diseases 0.000 claims description 13
• 235000019786 weight gain Nutrition 0.000 claims description 13
• IDKWKFTXXFZPQK-UHFFFAOYSA-N spiro[3,4-dihydrochromene-2,4'-piperidine] Chemical compound C1CNCCC21OC1=CC=CC=C1CC2 IDKWKFTXXFZPQK-UHFFFAOYSA-N 0.000 claims description 9
• 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims description 8
• 230000004584 weight gain Effects 0.000 claims description 8
• 125000002619 bicyclic group Chemical group 0.000 claims description 7
• 239000000164 antipsychotic agent Substances 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• WMZKTNCWQSQTHO-UHFFFAOYSA-N N-ethoxy-5-(8-methoxyquinolin-7-yl)spiro[3H-1-benzofuran-2,4'-piperidine]-1'-carboxamide Chemical compound C(C)ONC(=O)N1CCC2(CC1)OC1=C(C2)C=C(C=C1)C1=CC=C2C=CC=NC2=C1OC WMZKTNCWQSQTHO-UHFFFAOYSA-N 0.000 claims description 4
• 150000003857 carboxamides Chemical class 0.000 claims description 4
• 238000002651 drug therapy Methods 0.000 claims description 4
• CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 claims description 3
• BLWXFEUDFIEAIO-UHFFFAOYSA-N N-ethoxy-5-(7-methylpyrazolo[1,5-a]pyridin-6-yl)spiro[3H-1-benzofuran-2,4'-piperidine]-1'-carboxamide Chemical compound CCONC(=O)N1CCC2(Cc3cc(ccc3O2)-c2ccc3ccnn3c2C)CC1 BLWXFEUDFIEAIO-UHFFFAOYSA-N 0.000 claims description 3
• 229960004372 aripiprazole Drugs 0.000 claims description 3
• 229960004170 clozapine Drugs 0.000 claims description 3
• QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical group C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 claims description 3
• 229960005017 olanzapine Drugs 0.000 claims description 3
• KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 claims description 3
• 229960004431 quetiapine Drugs 0.000 claims description 3
• URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 claims description 3
• 229960001534 risperidone Drugs 0.000 claims description 3
• RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 claims description 3
• 229960000607 ziprasidone Drugs 0.000 claims description 3
• MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 claims description 3
• YAGOXVDHIALYFC-UHFFFAOYSA-N 1-[6-(8-chloroquinolin-7-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-yl]propan-1-one Chemical compound CCC(=O)N1CCC2(CC1)OCc1cc(ccc1O2)-c1ccc2cccnc2c1Cl YAGOXVDHIALYFC-UHFFFAOYSA-N 0.000 claims description 2
• HNTNWJFGZVHFDS-UHFFFAOYSA-N 6-(8-methoxyquinolin-7-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound COC=1C(=CC=C2C=CC=NC=12)C=1C=C2CCC3(CCN(CC3)C(=O)N)OC2=CC=1 HNTNWJFGZVHFDS-UHFFFAOYSA-N 0.000 claims description 2
• MCLRMCGTPPMNBQ-UHFFFAOYSA-N 6-isoquinolin-3-ylspiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide Chemical compound NC(=O)N1CCC2(CC1)OCc1cc(ccc1O2)-c1cc2ccccc2cn1 MCLRMCGTPPMNBQ-UHFFFAOYSA-N 0.000 claims description 2
• CVAFKDLVSQVYAX-UHFFFAOYSA-N N-ethoxy-6-isoquinolin-3-ylspiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide Chemical compound C(C)ONC(=O)N1CCC2(CC1)OCC1=C(O2)C=CC(=C1)C=1N=CC2=CC=CC=C2C=1 CVAFKDLVSQVYAX-UHFFFAOYSA-N 0.000 claims description 2
• QFFXSEJHIBDNFY-UHFFFAOYSA-N N-methoxy-5-(7-methylpyrazolo[1,5-a]pyridin-6-yl)spiro[3H-1-benzofuran-2,4'-piperidine]-1'-carboxamide Chemical compound CONC(=O)N1CCC2(Cc3cc(ccc3O2)-c2ccc3ccnn3c2C)CC1 QFFXSEJHIBDNFY-UHFFFAOYSA-N 0.000 claims description 2
• QCPUQKQVJVVYEK-UHFFFAOYSA-N cyclopropyl-(6-quinolin-3-ylspiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-yl)methanone Chemical compound O=C(C1CC1)N1CCC2(CC1)OCc1cc(ccc1O2)-c1cnc2ccccc2c1 QCPUQKQVJVVYEK-UHFFFAOYSA-N 0.000 claims description 2
• VPFPEPIBJBVRRN-UHFFFAOYSA-N spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide Chemical compound N1(CCC2(OCC3=C(O2)C=CC=C3)CC1)C(=O)N VPFPEPIBJBVRRN-UHFFFAOYSA-N 0.000 claims description 2
• 229910052760 oxygen Inorganic materials 0.000 claims 4
• CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims 3
• CGCKKVHXTGJLJS-UHFFFAOYSA-N 1-(6-quinolin-3-ylspiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-yl)propan-1-one Chemical compound N1=CC(=CC2=CC=CC=C12)C1=CC2=C(OC3(CCN(CC3)C(CC)=O)OC2)C=C1 CGCKKVHXTGJLJS-UHFFFAOYSA-N 0.000 claims 2
• SLWIMVMLZCYJTA-UHFFFAOYSA-N 1'-propanoyl-6-quinolin-3-ylspiro[3H-chromene-2,4'-piperidine]-4-one Chemical compound CCC(=O)N1CCC2(CC1)CC(=O)c1cc(ccc1O2)-c1cnc2ccccc2c1 SLWIMVMLZCYJTA-UHFFFAOYSA-N 0.000 claims 1
• IGQCXTAAKJZYMH-UHFFFAOYSA-N 1-(4-hydroxy-6-quinolin-3-ylspiro[3,4-dihydrochromene-2,4'-piperidine]-1'-yl)propan-1-one Chemical compound CCC(=O)N1CCC2(CC1)CC(O)c1cc(ccc1O2)-c1cnc2ccccc2c1 IGQCXTAAKJZYMH-UHFFFAOYSA-N 0.000 claims 1
• XZDRGWBFJUVQBE-UHFFFAOYSA-N 1-(6-quinolin-3-ylspiro[3,4-dihydrochromene-2,4'-piperidine]-1'-yl)propan-1-one Chemical compound CCC(=O)N1CCC2(CC1)CCc1cc(ccc1O2)-c1cnc2ccccc2c1 XZDRGWBFJUVQBE-UHFFFAOYSA-N 0.000 claims 1
• WWOIXEZKQUAMDA-UHFFFAOYSA-N 1-(6-quinolin-3-ylspiro[chromene-2,4'-piperidine]-1'-yl)propan-1-one Chemical compound N1=CC(=CC2=CC=CC=C12)C=1C=C2C=CC3(CCN(CC3)C(CC)=O)OC2=CC=1 WWOIXEZKQUAMDA-UHFFFAOYSA-N 0.000 claims 1
• ZCIUDHYNDOQRFW-UHFFFAOYSA-N 1-[6-(1,5-naphthyridin-3-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-yl]propan-1-one Chemical compound CCC(=O)N1CCC2(CC1)OCc1cc(ccc1O2)-c1cnc2cccnc2c1 ZCIUDHYNDOQRFW-UHFFFAOYSA-N 0.000 claims 1
• QMKIWQDHETYEEG-UHFFFAOYSA-N 1-[6-(1-methylisoquinolin-6-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-yl]propan-1-one Chemical compound CC1=NC=CC2=CC(=CC=C12)C=1C=C2CCC3(CCN(CC3)C(CC)=O)OC2=CC=1 QMKIWQDHETYEEG-UHFFFAOYSA-N 0.000 claims 1
• DSUACZAXIJPLGH-UHFFFAOYSA-N 1-[6-(1-methylisoquinolin-6-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-yl]propan-1-one Chemical compound CCC(=O)N1CCC2(CC1)OCc1cc(ccc1O2)-c1ccc2c(C)nccc2c1 DSUACZAXIJPLGH-UHFFFAOYSA-N 0.000 claims 1
• BVFNCPAMMNRSII-UHFFFAOYSA-N 1-[6-(4-methylquinolin-3-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-yl]propan-1-one Chemical compound CCC(=O)N1CCC2(CC1)CCc1cc(ccc1O2)-c1cnc2ccccc2c1C BVFNCPAMMNRSII-UHFFFAOYSA-N 0.000 claims 1
• ARQXXAKYDNYALM-UHFFFAOYSA-N 1-[6-(4-methylquinolin-3-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-yl]propan-1-one Chemical compound CCC(=O)N1CCC2(CC1)OCc1cc(ccc1O2)-c1cnc2ccccc2c1C ARQXXAKYDNYALM-UHFFFAOYSA-N 0.000 claims 1
• CAUHLHFEVMZAGI-UHFFFAOYSA-N 1-[6-(8-chloroquinolin-7-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-yl]-2-hydroxyethanone Chemical compound OCC(=O)N1CCC2(CC1)CCc1cc(ccc1O2)-c1ccc2cccnc2c1Cl CAUHLHFEVMZAGI-UHFFFAOYSA-N 0.000 claims 1
• UMEZKVFPBSMCMZ-UHFFFAOYSA-N 1-[6-(8-chloroquinolin-7-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-yl]propan-1-one Chemical compound CCC(=O)N1CCC2(CC1)CCc1cc(ccc1O2)-c1ccc2cccnc2c1Cl UMEZKVFPBSMCMZ-UHFFFAOYSA-N 0.000 claims 1
• URRAEBMQSHSIBQ-UHFFFAOYSA-N 1-[6-(8-methoxyquinolin-7-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-yl]propan-1-one Chemical compound CCC(=O)N1CCC2(CC1)CCc1cc(ccc1O2)-c1ccc2cccnc2c1OC URRAEBMQSHSIBQ-UHFFFAOYSA-N 0.000 claims 1
• RCXQHSIVMADDEV-UHFFFAOYSA-N 1-[6-(8-methoxyquinolin-7-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-yl]propan-1-one Chemical compound CCC(=O)N1CCC2(CC1)OCc1cc(ccc1O2)-c1ccc2cccnc2c1OC RCXQHSIVMADDEV-UHFFFAOYSA-N 0.000 claims 1
• ZKLKGWJMNULWCB-UHFFFAOYSA-N 1-[6-(8-methylquinolin-3-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-yl]propan-1-one Chemical compound CCC(=O)N1CCC2(CC1)CCc1cc(ccc1O2)-c1cnc2c(C)cccc2c1 ZKLKGWJMNULWCB-UHFFFAOYSA-N 0.000 claims 1
• OLTUTPILWTXELR-UHFFFAOYSA-N 1-[6-(8-methylquinolin-6-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-yl]propan-1-one Chemical compound CCC(=O)N1CCC2(CC1)CCc1cc(ccc1O2)-c1cc(C)c2ncccc2c1 OLTUTPILWTXELR-UHFFFAOYSA-N 0.000 claims 1
• MBGZPPDTXKKNRC-UHFFFAOYSA-N 1-[6-(8-methylquinolin-7-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-yl]propan-1-one Chemical compound CC=1C(=CC=C2C=CC=NC=12)C=1C=C2CCC3(CCN(CC3)C(CC)=O)OC2=CC=1 MBGZPPDTXKKNRC-UHFFFAOYSA-N 0.000 claims 1
• BRRQJWQWFZORBD-UHFFFAOYSA-N 1-[6-(8-methylquinolin-7-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-yl]propan-1-one Chemical compound CCC(=O)N1CCC2(CC1)OCc1cc(ccc1O2)-c1ccc2cccnc2c1C BRRQJWQWFZORBD-UHFFFAOYSA-N 0.000 claims 1
• QFUUJADEIXXLCI-UHFFFAOYSA-N 2-hydroxy-1-[6-(8-methylquinolin-7-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-yl]ethanone Chemical compound OCC(=O)N1CCC2(CC1)OC1=CC=C(C=C1CC2)C1=CC=C2C=CC=NC2=C1C QFUUJADEIXXLCI-UHFFFAOYSA-N 0.000 claims 1
• YQQLXQBBDLSPKB-UHFFFAOYSA-N 2-hydroxy-1-[6-(8-methylquinolin-7-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-yl]ethanone Chemical compound Cc1c(ccc2cccnc12)-c1ccc2OC3(CCN(CC3)C(=O)CO)OCc2c1 YQQLXQBBDLSPKB-UHFFFAOYSA-N 0.000 claims 1
• MBDTWNUXFNLLST-UHFFFAOYSA-N 2-methyl-1-(6-quinolin-3-ylspiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-yl)propan-1-one Chemical compound CC(C)C(=O)N1CCC2(CC1)OCc1cc(ccc1O2)-c1cnc2ccccc2c1 MBDTWNUXFNLLST-UHFFFAOYSA-N 0.000 claims 1
• MWRUYUNGWDZYJJ-UHFFFAOYSA-N 2-methyl-1-(6-quinolin-7-ylspiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-yl)propan-1-one Chemical compound CC(C(=O)N1CCC2(CC1)OCC1=C(O2)C=CC(=C1)C1=CC=C2C=CC=NC2=C1)C MWRUYUNGWDZYJJ-UHFFFAOYSA-N 0.000 claims 1
• XYNOIPHVLUZEIK-UHFFFAOYSA-N 4-hydroxy-6-(8-methylquinolin-7-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound OC1CC2(CCN(CC2)C(=O)N)OC2=CC=C(C=C12)C1=CC=C2C=CC=NC2=C1C XYNOIPHVLUZEIK-UHFFFAOYSA-N 0.000 claims 1
• NYLQWFUTFIHDJT-UHFFFAOYSA-N 5-(4-methylquinolin-3-yl)spiro[3H-1-benzofuran-2,4'-piperidine]-1'-carboxamide Chemical compound CC1=C(C=NC2=CC=CC=C12)C=1C=CC2=C(CC3(CCN(CC3)C(=O)N)O2)C=1 NYLQWFUTFIHDJT-UHFFFAOYSA-N 0.000 claims 1
• RSSMTUQEWCUWCM-UHFFFAOYSA-N 5-(7-methylpyrazolo[1,5-a]pyridin-6-yl)-N-(oxan-2-yloxy)spiro[3H-1-benzofuran-2,4'-piperidine]-1'-carboxamide Chemical compound Cc1c(ccc2ccnn12)-c1ccc2OC3(Cc2c1)CCN(CC3)C(=O)NOC1CCCCO1 RSSMTUQEWCUWCM-UHFFFAOYSA-N 0.000 claims 1
• UIJZMADUSNRCNQ-UHFFFAOYSA-N 5-(8-methoxyquinolin-7-yl)-N-(oxan-2-yloxy)spiro[3H-1-benzofuran-2,4'-piperidine]-1'-carboxamide Chemical compound COC=1C(=CC=C2C=CC=NC=12)C=1C=CC2=C(CC3(CCN(CC3)C(=O)NOC3OCCCC3)O2)C=1 UIJZMADUSNRCNQ-UHFFFAOYSA-N 0.000 claims 1
• HZLVDRXQJCLCTK-UHFFFAOYSA-N 5-(8-methoxyquinolin-7-yl)spiro[3H-1-benzofuran-2,4'-piperidine]-1'-carboxamide Chemical compound COC=1C(=CC=C2C=CC=NC=12)C=1C=CC2=C(CC3(CCN(CC3)C(=O)N)O2)C=1 HZLVDRXQJCLCTK-UHFFFAOYSA-N 0.000 claims 1
• TXACCBYTSBIFAH-UHFFFAOYSA-N 5-(8-methylquinolin-7-yl)spiro[3H-1-benzofuran-2,4'-piperidine]-1'-carboxamide Chemical compound CC=1C(=CC=C2C=CC=NC=12)C=1C=CC2=C(CC3(CCN(CC3)C(=O)N)O2)C=1 TXACCBYTSBIFAH-UHFFFAOYSA-N 0.000 claims 1
• HMJGVEKYBCUJTO-UHFFFAOYSA-N 5-fluoro-6-(8-methylquinolin-7-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound FC1=C2CCC3(CCN(CC3)C(=O)N)OC2=CC=C1C1=CC=C2C=CC=NC2=C1C HMJGVEKYBCUJTO-UHFFFAOYSA-N 0.000 claims 1
• GSRZFGYBHQQWLB-UHFFFAOYSA-N 5-methyl-6-(1-methylisoquinolin-6-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound CC1=C2CCC3(CCN(CC3)C(=O)N)OC2=CC=C1C=1C=C2C=CN=C(C2=CC=1)C GSRZFGYBHQQWLB-UHFFFAOYSA-N 0.000 claims 1
• CFADSSLZPAEWFT-UHFFFAOYSA-N 5-methyl-6-(8-methylquinolin-7-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound CC1=C2CCC3(CCN(CC3)C(=O)N)OC2=CC=C1C1=CC=C2C=CC=NC2=C1C CFADSSLZPAEWFT-UHFFFAOYSA-N 0.000 claims 1
• OZOSZQXKECJJPS-UHFFFAOYSA-N 6-(1,3-benzothiazol-5-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound S1C=NC2=C1C=CC(=C2)C=1C=C2CCC3(CCN(CC3)C(=O)N)OC2=CC=1 OZOSZQXKECJJPS-UHFFFAOYSA-N 0.000 claims 1
• ZUKSCHWPPNFUJY-UHFFFAOYSA-N 6-(1,3-benzothiazol-6-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound S1C=NC2=C1C=C(C=C2)C=1C=C2CCC3(CCN(CC3)C(=O)N)OC2=CC=1 ZUKSCHWPPNFUJY-UHFFFAOYSA-N 0.000 claims 1
• CHNFOEKWAAGEKM-UHFFFAOYSA-N 6-(1,3-benzoxazol-5-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound O1C=NC2=C1C=CC(=C2)C=1C=C2CCC3(CCN(CC3)C(=O)N)OC2=CC=1 CHNFOEKWAAGEKM-UHFFFAOYSA-N 0.000 claims 1
• WQRGGDRKNANGSE-UHFFFAOYSA-N 6-(1,8-naphthyridin-3-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound N1=CC(=CC2=CC=CN=C12)C=1C=C2CCC3(CCN(CC3)C(=O)N)OC2=CC=1 WQRGGDRKNANGSE-UHFFFAOYSA-N 0.000 claims 1
• OWTMHQUGLUXFFX-UHFFFAOYSA-N 6-(1-benzofuran-5-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound O1C=CC2=C1C=CC(=C2)C=1C=C2CCC3(CCN(CC3)C(=O)N)OC2=CC=1 OWTMHQUGLUXFFX-UHFFFAOYSA-N 0.000 claims 1
• FYRBKOMFWPITJD-UHFFFAOYSA-N 6-(1-methylbenzimidazol-5-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound CN1C=NC2=C1C=CC(=C2)C=1C=C2CCC3(CCN(CC3)C(=O)N)OC2=CC=1 FYRBKOMFWPITJD-UHFFFAOYSA-N 0.000 claims 1
• XJBUYKCMJZCJTL-UHFFFAOYSA-N 6-(1-methylindol-5-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound CN1C=CC2=CC(=CC=C12)C=1C=C2CCC3(CCN(CC3)C(=O)N)OC2=CC=1 XJBUYKCMJZCJTL-UHFFFAOYSA-N 0.000 claims 1
• SOKYCUZJULWMMR-UHFFFAOYSA-N 6-(1-methylisoquinolin-6-yl)-N-(2-methylpropyl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound C(C(C)C)NC(=O)N1CCC2(CC1)OC1=CC=C(C=C1CC2)C=1C=C2C=CN=C(C2=CC=1)C SOKYCUZJULWMMR-UHFFFAOYSA-N 0.000 claims 1
• SRYFCLVBSCPZMG-UHFFFAOYSA-N 6-(1-methylisoquinolin-6-yl)-N-propan-2-yloxyspiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound C(C)(C)ONC(=O)N1CCC2(CC1)OC1=CC=C(C=C1CC2)C=1C=C2C=CN=C(C2=CC=1)C SRYFCLVBSCPZMG-UHFFFAOYSA-N 0.000 claims 1
• PAAZIQYGTGILRW-UHFFFAOYSA-N 6-(1-methylisoquinolin-6-yl)-N-propan-2-yloxyspiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide Chemical compound C(C)(C)ONC(=O)N1CCC2(CC1)OCC1=C(O2)C=CC(=C1)C=1C=C2C=CN=C(C2=CC=1)C PAAZIQYGTGILRW-UHFFFAOYSA-N 0.000 claims 1
• WZDMMHQUMIKHHG-UHFFFAOYSA-N 6-(1-methylisoquinolin-6-yl)-N-propoxyspiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound CC1=NC=CC2=CC(=CC=C12)C=1C=C2CCC3(CCN(CC3)C(=O)NOCCC)OC2=CC=1 WZDMMHQUMIKHHG-UHFFFAOYSA-N 0.000 claims 1
• NOSJQBRADLJKSX-UHFFFAOYSA-N 6-(1-methylisoquinolin-6-yl)-N-propylspiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound CC1=NC=CC2=CC(=CC=C12)C=1C=C2CCC3(CCN(CC3)C(=O)NCCC)OC2=CC=1 NOSJQBRADLJKSX-UHFFFAOYSA-N 0.000 claims 1
• WFDZTTUTOCDTPU-UHFFFAOYSA-N 6-(1-methylisoquinolin-6-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound CC1=NC=CC2=CC(=CC=C12)C=1C=C2CCC3(CCN(CC3)C(=O)N)OC2=CC=1 WFDZTTUTOCDTPU-UHFFFAOYSA-N 0.000 claims 1
• HZXRIPIILLWWJH-UHFFFAOYSA-N 6-(1-methylisoquinolin-6-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide Chemical compound Cc1nccc2cc(ccc12)-c1ccc2OC3(CCN(CC3)C(N)=O)OCc2c1 HZXRIPIILLWWJH-UHFFFAOYSA-N 0.000 claims 1
• OVZDRWVZRLEZEZ-UHFFFAOYSA-N 6-(1H-indol-3-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound N1C=C(C2=CC=CC=C12)C=1C=C2CCC3(CCN(CC3)C(=O)N)OC2=CC=1 OVZDRWVZRLEZEZ-UHFFFAOYSA-N 0.000 claims 1
• RFGXTJDVUOLIHQ-UHFFFAOYSA-N 6-(1H-indol-3-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide Chemical compound NC(=O)N1CCC2(CC1)OCc1cc(ccc1O2)-c1c[nH]c2ccccc12 RFGXTJDVUOLIHQ-UHFFFAOYSA-N 0.000 claims 1
• YVCMGXVXMGQAJL-UHFFFAOYSA-N 6-(1H-indol-5-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound N1C=CC2=CC(=CC=C12)C=1C=C2CCC3(CCN(CC3)C(=O)N)OC2=CC=1 YVCMGXVXMGQAJL-UHFFFAOYSA-N 0.000 claims 1
• GMTVGDMMOCWZFY-UHFFFAOYSA-N 6-(3-methylisoquinolin-6-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound CC=1N=CC2=CC=C(C=C2C=1)C=1C=C2CCC3(CCN(CC3)C(=O)N)OC2=CC=1 GMTVGDMMOCWZFY-UHFFFAOYSA-N 0.000 claims 1
• JKBLCVHNHZTKMT-UHFFFAOYSA-N 6-(3-methylisoquinolin-6-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide Chemical compound Cc1cc2cc(ccc2cn1)-c1ccc2OC3(CCN(CC3)C(N)=O)OCc2c1 JKBLCVHNHZTKMT-UHFFFAOYSA-N 0.000 claims 1
• ILESCJMILHPURO-UHFFFAOYSA-N 6-(4-methylquinolin-3-yl)-N-propan-2-yloxyspiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound C(C)(C)ONC(=O)N1CCC2(CC1)OC1=CC=C(C=C1CC2)C=1C=NC2=CC=CC=C2C=1C ILESCJMILHPURO-UHFFFAOYSA-N 0.000 claims 1
• XWAVLOKSTBAIOU-UHFFFAOYSA-N 6-(4-methylquinolin-3-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound CC1=C(C=NC2=CC=CC=C12)C=1C=C2CCC3(CCN(CC3)C(=O)N)OC2=CC=1 XWAVLOKSTBAIOU-UHFFFAOYSA-N 0.000 claims 1
• OTGIOEZPHWEIJM-UHFFFAOYSA-N 6-(5-chloroimidazo[1,2-a]pyridin-6-yl)-N-(2-methylpropyl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound CC(C)CNC(=O)N1CCC2(CC1)CCc1cc(ccc1O2)-c1ccc2nccn2c1Cl OTGIOEZPHWEIJM-UHFFFAOYSA-N 0.000 claims 1
• NRDSIJWBOZNGMW-UHFFFAOYSA-N 6-(7-methylpyrazolo[1,5-a]pyridin-6-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound Cc1c(ccc2ccnn12)-c1ccc2OC3(CCN(CC3)C(N)=O)CCc2c1 NRDSIJWBOZNGMW-UHFFFAOYSA-N 0.000 claims 1
• YDSFQSQPXQEJLA-UHFFFAOYSA-N 6-(8-chloroquinolin-7-yl)-N-(oxan-2-yloxy)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound ClC=1C(=CC=C2C=CC=NC=12)C=1C=C2CCC3(CCN(CC3)C(=O)NOC3OCCCC3)OC2=CC=1 YDSFQSQPXQEJLA-UHFFFAOYSA-N 0.000 claims 1
• YKCLTNCAPLFEEU-UHFFFAOYSA-N 6-(8-chloroquinolin-7-yl)-N-ethylspiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound ClC=1C(=CC=C2C=CC=NC=12)C=1C=C2CCC3(CCN(CC3)C(=O)NCC)OC2=CC=1 YKCLTNCAPLFEEU-UHFFFAOYSA-N 0.000 claims 1
• ZVJZXMLYQNAZKT-UHFFFAOYSA-N 6-(8-chloroquinolin-7-yl)-N-hydroxyspiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound ClC=1C(=CC=C2C=CC=NC=12)C=1C=C2CCC3(CCN(CC3)C(=O)NO)OC2=CC=1 ZVJZXMLYQNAZKT-UHFFFAOYSA-N 0.000 claims 1
• GHEQVQKGMXJSLP-UHFFFAOYSA-N 6-(8-chloroquinolin-7-yl)-N-hydroxyspiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide Chemical compound ONC(=O)N1CCC2(CC1)OCc1cc(ccc1O2)-c1ccc2cccnc2c1Cl GHEQVQKGMXJSLP-UHFFFAOYSA-N 0.000 claims 1
• HSBZGOZWPJZOCH-UHFFFAOYSA-N 6-(8-chloroquinolin-7-yl)-N-methoxyspiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide Chemical compound ClC=1C(=CC=C2C=CC=NC=12)C1=CC2=C(OC3(CCN(CC3)C(=O)NOC)OC2)C=C1 HSBZGOZWPJZOCH-UHFFFAOYSA-N 0.000 claims 1
• PAUGVYAZAASZBG-UHFFFAOYSA-N 6-(8-chloroquinolin-7-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound ClC=1C(=CC=C2C=CC=NC=12)C=1C=C2CCC3(CCN(CC3)C(=O)N)OC2=CC=1 PAUGVYAZAASZBG-UHFFFAOYSA-N 0.000 claims 1
• YHTVVSPEHSCAAM-UHFFFAOYSA-N 6-(8-chloroquinolin-7-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide Chemical compound ClC=1C(=CC=C2C=CC=NC=12)C1=CC2=C(OC3(CCN(CC3)C(=O)N)OC2)C=C1 YHTVVSPEHSCAAM-UHFFFAOYSA-N 0.000 claims 1
• VBXOLDBYMAZMSU-UHFFFAOYSA-N 6-(8-methoxyquinolin-7-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide Chemical compound COc1c(ccc2cccnc12)-c1ccc2OC3(CCN(CC3)C(N)=O)OCc2c1 VBXOLDBYMAZMSU-UHFFFAOYSA-N 0.000 claims 1
• DQXITAQBNKVVPN-UHFFFAOYSA-N 6-(8-methyl-4-oxo-1H-quinolin-7-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound OC1=CC=NC2=C(C(=CC=C12)C=1C=C2CCC3(CCN(CC3)C(=O)N)OC2=CC=1)C DQXITAQBNKVVPN-UHFFFAOYSA-N 0.000 claims 1
• RMYSCOXINKRMSC-UHFFFAOYSA-N 6-(8-methylquinolin-7-yl)-4-oxospiro[3H-chromene-2,4'-piperidine]-1'-carboxamide Chemical compound CC=1C(=CC=C2C=CC=NC=12)C=1C=C2C(CC3(CCN(CC3)C(=O)N)OC2=CC=1)=O RMYSCOXINKRMSC-UHFFFAOYSA-N 0.000 claims 1
• AYACNUYVEKENPM-UHFFFAOYSA-N 6-(8-methylquinolin-7-yl)-N-propan-2-yloxyspiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound C(C)(C)ONC(=O)N1CCC2(CC1)OC1=CC=C(C=C1CC2)C1=CC=C2C=CC=NC2=C1C AYACNUYVEKENPM-UHFFFAOYSA-N 0.000 claims 1
• DYGIJPKEYHPUGO-UHFFFAOYSA-N 6-(8-methylquinolin-7-yl)-N-propan-2-yloxyspiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide Chemical compound CC(C)ONC(=O)N1CCC2(CC1)OCc1cc(ccc1O2)-c1ccc2cccnc2c1C DYGIJPKEYHPUGO-UHFFFAOYSA-N 0.000 claims 1
• JLMRVEUGLPEBKH-UHFFFAOYSA-N 6-(8-methylquinolin-7-yl)-N-propan-2-ylspiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound C(C)(C)NC(=O)N1CCC2(CC1)OC1=CC=C(C=C1CC2)C1=CC=C2C=CC=NC2=C1C JLMRVEUGLPEBKH-UHFFFAOYSA-N 0.000 claims 1
• SCDZXEAPCSCUKV-UHFFFAOYSA-N 6-(8-methylquinolin-7-yl)-N-propoxyspiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound CC=1C(=CC=C2C=CC=NC=12)C=1C=C2CCC3(CCN(CC3)C(=O)NOCCC)OC2=CC=1 SCDZXEAPCSCUKV-UHFFFAOYSA-N 0.000 claims 1
• PAXIHGGOLOUFRL-UHFFFAOYSA-N 6-(8-methylquinolin-7-yl)-N-propylspiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound CC=1C(=CC=C2C=CC=NC=12)C=1C=C2CCC3(CCN(CC3)C(=O)NCCC)OC2=CC=1 PAXIHGGOLOUFRL-UHFFFAOYSA-N 0.000 claims 1
• WZJSVCDAAFEZHZ-UHFFFAOYSA-N 6-isoquinolin-3-yl-N-(oxan-2-yloxy)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide Chemical compound O=C(NOC1CCCCO1)N1CCC2(CC1)OCc1cc(ccc1O2)-c1cc2ccccc2cn1 WZJSVCDAAFEZHZ-UHFFFAOYSA-N 0.000 claims 1
• KLOAXWXWIWKCKB-UHFFFAOYSA-N 6-isoquinolin-3-yl-N-methoxyspiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound C1=NC(=CC2=CC=CC=C12)C=1C=C2CCC3(CCN(CC3)C(=O)NOC)OC2=CC=1 KLOAXWXWIWKCKB-UHFFFAOYSA-N 0.000 claims 1
• NBUPJTRIWLLZRJ-UHFFFAOYSA-N 6-isoquinolin-3-yl-N-methoxyspiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide Chemical compound CONC(=O)N1CCC2(CC1)OCc1cc(ccc1O2)-c1cc2ccccc2cn1 NBUPJTRIWLLZRJ-UHFFFAOYSA-N 0.000 claims 1
• DABPGVZTYMDPTP-UHFFFAOYSA-N 6-isoquinolin-3-ylspiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound C1=NC(=CC2=CC=CC=C12)C=1C=C2CCC3(CCN(CC3)C(=O)N)OC2=CC=1 DABPGVZTYMDPTP-UHFFFAOYSA-N 0.000 claims 1
• RFAIHKLGBQXIRR-UHFFFAOYSA-N 6-thieno[2,3-b]pyridin-5-ylspiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide Chemical compound NC(=O)N1CCC2(CC1)OCc1cc(ccc1O2)-c1cnc2sccc2c1 RFAIHKLGBQXIRR-UHFFFAOYSA-N 0.000 claims 1
• USTICMVVVLGCAB-UHFFFAOYSA-N 8-chloro-N-methoxy-6-(8-methylquinolin-7-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound ClC=1C=C(C=C2CCC3(CCN(CC3)C(=O)NOC)OC=12)C1=CC=C2C=CC=NC2=C1C USTICMVVVLGCAB-UHFFFAOYSA-N 0.000 claims 1
• PNFPJIRDUGYZKS-UHFFFAOYSA-N 8-fluoro-N-methoxy-6-(8-methylquinolin-7-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound FC=1C=C(C=C2CCC3(CCN(CC3)C(=O)NOC)OC=12)C1=CC=C2C=CC=NC2=C1C PNFPJIRDUGYZKS-UHFFFAOYSA-N 0.000 claims 1
• FSUMQKBOYIXDFY-UHFFFAOYSA-N N-(2-methylpropyl)-6-(8-methylquinolin-7-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound C(C(C)C)NC(=O)N1CCC2(CC1)OC1=CC=C(C=C1CC2)C1=CC=C2C=CC=NC2=C1C FSUMQKBOYIXDFY-UHFFFAOYSA-N 0.000 claims 1
• SOHUSVRTCWBMAD-UHFFFAOYSA-N N-ethoxy-5-(4-methylquinolin-3-yl)spiro[3H-1-benzofuran-2,4'-piperidine]-1'-carboxamide Chemical compound C(C)ONC(=O)N1CCC2(CC1)OC1=C(C2)C=C(C=C1)C=1C=NC2=CC=CC=C2C=1C SOHUSVRTCWBMAD-UHFFFAOYSA-N 0.000 claims 1
• AUAGRRUUXHWTFG-UHFFFAOYSA-N N-ethoxy-5-(8-methylquinolin-7-yl)spiro[3H-1-benzofuran-2,4'-piperidine]-1'-carboxamide Chemical compound C(C)ONC(=O)N1CCC2(CC1)OC1=C(C2)C=C(C=C1)C1=CC=C2C=CC=NC2=C1C AUAGRRUUXHWTFG-UHFFFAOYSA-N 0.000 claims 1
• FJNBOCPBKOFCKF-UHFFFAOYSA-N N-ethoxy-6-(1-methylisoquinolin-6-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound C(C)ONC(=O)N1CCC2(CC1)OC1=CC=C(C=C1CC2)C=1C=C2C=CN=C(C2=CC=1)C FJNBOCPBKOFCKF-UHFFFAOYSA-N 0.000 claims 1
• MWLOGKJDLSOVPG-UHFFFAOYSA-N N-ethoxy-6-(1-methylisoquinolin-6-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide Chemical compound CCONC(=O)N1CCC2(CC1)OCc1cc(ccc1O2)-c1ccc2c(C)nccc2c1 MWLOGKJDLSOVPG-UHFFFAOYSA-N 0.000 claims 1
• NNSJSJJIBLVNNW-UHFFFAOYSA-N N-ethoxy-6-(4-methylquinolin-3-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound C(C)ONC(=O)N1CCC2(CC1)OC1=CC=C(C=C1CC2)C=1C=NC2=CC=CC=C2C=1C NNSJSJJIBLVNNW-UHFFFAOYSA-N 0.000 claims 1
• BPMCIBBOBINBQG-UHFFFAOYSA-N N-ethoxy-6-(4-methylquinolin-3-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide Chemical compound CCONC(=O)N1CCC2(CC1)OCc1cc(ccc1O2)-c1cnc2ccccc2c1C BPMCIBBOBINBQG-UHFFFAOYSA-N 0.000 claims 1
• GAACBXGWOAPUPK-UHFFFAOYSA-N N-ethoxy-6-isoquinolin-3-ylspiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound C(C)ONC(=O)N1CCC2(CC1)OC1=CC=C(C=C1CC2)C=1N=CC2=CC=CC=C2C=1 GAACBXGWOAPUPK-UHFFFAOYSA-N 0.000 claims 1
• MHNDXNDGCJBXRC-UHFFFAOYSA-N N-ethoxy-7-(8-methylquinolin-7-yl)spiro[4,5-dihydro-1,3-benzodioxepine-2,4'-piperidine]-1'-carboxamide Chemical compound CCONC(=O)N1CCC2(CC1)OCCc1cc(ccc1O2)-c1ccc2cccnc2c1C MHNDXNDGCJBXRC-UHFFFAOYSA-N 0.000 claims 1
• PWFLVGVAAPRUHM-UHFFFAOYSA-N N-ethyl-5-(4-methylquinolin-3-yl)spiro[3H-1-benzofuran-2,4'-piperidine]-1'-carboxamide Chemical compound C(C)NC(=O)N1CCC2(CC1)OC1=C(C2)C=C(C=C1)C=1C=NC2=CC=CC=C2C=1C PWFLVGVAAPRUHM-UHFFFAOYSA-N 0.000 claims 1
• NLIFOVUGMWKPHX-UHFFFAOYSA-N N-ethyl-5-(7-methylpyrazolo[1,5-a]pyridin-6-yl)spiro[3H-1-benzofuran-2,4'-piperidine]-1'-carboxamide Chemical compound CCNC(=O)N1CCC2(Cc3cc(ccc3O2)-c2ccc3ccnn3c2C)CC1 NLIFOVUGMWKPHX-UHFFFAOYSA-N 0.000 claims 1
• LWXBJLKGJWDUFW-UHFFFAOYSA-N N-ethyl-5-(8-methoxyquinolin-7-yl)spiro[3H-1-benzofuran-2,4'-piperidine]-1'-carboxamide Chemical compound C(C)NC(=O)N1CCC2(CC1)OC1=C(C2)C=C(C=C1)C1=CC=C2C=CC=NC2=C1OC LWXBJLKGJWDUFW-UHFFFAOYSA-N 0.000 claims 1
• FGFRTZVNADVTJA-UHFFFAOYSA-N N-ethyl-5-(8-methylquinolin-7-yl)spiro[3H-1-benzofuran-2,4'-piperidine]-1'-carboxamide Chemical compound C(C)NC(=O)N1CCC2(CC1)OC1=C(C2)C=C(C=C1)C1=CC=C2C=CC=NC2=C1C FGFRTZVNADVTJA-UHFFFAOYSA-N 0.000 claims 1
• ZNPROSXLICUTTE-UHFFFAOYSA-N N-ethyl-6-(1-methylisoquinolin-6-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound C(C)NC(=O)N1CCC2(CC1)OC1=CC=C(C=C1CC2)C=1C=C2C=CN=C(C2=CC=1)C ZNPROSXLICUTTE-UHFFFAOYSA-N 0.000 claims 1
• WHWGRZCKOXJYPL-UHFFFAOYSA-N N-ethyl-6-(1-methylisoquinolin-6-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide Chemical compound CCNC(=O)N1CCC2(CC1)OCc1cc(ccc1O2)-c1ccc2c(C)nccc2c1 WHWGRZCKOXJYPL-UHFFFAOYSA-N 0.000 claims 1
• SIWQSJQYPQHCNK-UHFFFAOYSA-N N-ethyl-6-(3-methylisoquinolin-6-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide Chemical compound CCNC(=O)N1CCC2(CC1)OCc1cc(ccc1O2)-c1ccc2cnc(C)cc2c1 SIWQSJQYPQHCNK-UHFFFAOYSA-N 0.000 claims 1
• DFAOEQFVRNJITR-UHFFFAOYSA-N N-hydroxy-5-(4-methylquinolin-3-yl)spiro[3H-1-benzofuran-2,4'-piperidine]-1'-carboxamide Chemical compound CC1=C(C=NC2=CC=CC=C12)C=1C=CC2=C(CC3(CCN(CC3)C(=O)NO)O2)C=1 DFAOEQFVRNJITR-UHFFFAOYSA-N 0.000 claims 1
• ZKYRVKFYEOOJHW-UHFFFAOYSA-N N-hydroxy-5-(8-methoxyquinolin-7-yl)spiro[3H-1-benzofuran-2,4'-piperidine]-1'-carboxamide Chemical compound COC=1C(=CC=C2C=CC=NC=12)C=1C=CC2=C(CC3(CCN(CC3)C(=O)NO)O2)C=1 ZKYRVKFYEOOJHW-UHFFFAOYSA-N 0.000 claims 1
• JAJKDSCUBGJMOM-UHFFFAOYSA-N N-hydroxy-5-(8-methylquinolin-7-yl)spiro[3H-1-benzofuran-2,4'-piperidine]-1'-carboxamide Chemical compound CC=1C(=CC=C2C=CC=NC=12)C=1C=CC2=C(CC3(CCN(CC3)C(=O)NO)O2)C=1 JAJKDSCUBGJMOM-UHFFFAOYSA-N 0.000 claims 1
• DGXMLLJGNBUGST-UHFFFAOYSA-N N-hydroxy-6-(1-methylisoquinolin-6-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide Chemical compound Cc1nccc2cc(ccc12)-c1ccc2OC3(CCN(CC3)C(=O)NO)OCc2c1 DGXMLLJGNBUGST-UHFFFAOYSA-N 0.000 claims 1
• LRJHEZKHDOFCOT-UHFFFAOYSA-N N-hydroxy-6-(4-methylquinolin-3-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide Chemical compound Cc1c(cnc2ccccc12)-c1ccc2OC3(CCN(CC3)C(=O)NO)OCc2c1 LRJHEZKHDOFCOT-UHFFFAOYSA-N 0.000 claims 1
• RUVXLCHAQOPRGN-UHFFFAOYSA-N N-hydroxy-6-(5-methylimidazo[1,2-a]pyridin-6-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound Cc1c(ccc2nccn12)-c1ccc2OC3(CCN(CC3)C(=O)NO)CCc2c1 RUVXLCHAQOPRGN-UHFFFAOYSA-N 0.000 claims 1
• OUYMVYNBWUBBMQ-UHFFFAOYSA-N N-hydroxy-6-isoquinolin-3-ylspiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound C1=NC(=CC2=CC=CC=C12)C=1C=C2CCC3(CCN(CC3)C(=O)NO)OC2=CC=1 OUYMVYNBWUBBMQ-UHFFFAOYSA-N 0.000 claims 1
• VNGVNDFEFACDIB-UHFFFAOYSA-N N-hydroxy-6-isoquinolin-3-ylspiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide Chemical compound ONC(=O)N1CCC2(CC1)OCc1cc(ccc1O2)-c1cc2ccccc2cn1 VNGVNDFEFACDIB-UHFFFAOYSA-N 0.000 claims 1
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• FACKOKZUFULCSS-XMMPIXPASA-N [(2R)-oxolan-2-yl]-(6-quinolin-3-ylspiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-yl)methanone Chemical compound O=C([C@H]1CCCO1)N1CCC2(CC1)OCc1cc(ccc1O2)-c1cnc2ccccc2c1 FACKOKZUFULCSS-XMMPIXPASA-N 0.000 claims 1
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• OUJZRBDXIWVNBC-AREMUKBSSA-N [6-(1-methylisoquinolin-6-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-yl]-[(2R)-oxolan-2-yl]methanone Chemical compound CC1=NC=CC2=CC(=CC=C12)C=1C=C2CCC3(CCN(CC3)C(=O)[C@@H]3OCCC3)OC2=CC=1 OUJZRBDXIWVNBC-AREMUKBSSA-N 0.000 claims 1
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• JZYIRYKYIVLDDV-HSZRJFAPSA-N [6-(8-methoxyquinolin-7-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-yl]-[(2R)-oxolan-2-yl]methanone Chemical compound COc1c(ccc2cccnc12)-c1ccc2OC3(CCN(CC3)C(=O)[C@H]3CCCO3)OCc2c1 JZYIRYKYIVLDDV-HSZRJFAPSA-N 0.000 claims 1
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