JP2020511412A5 - - Google Patents
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- Publication number
- JP2020511412A5 JP2020511412A5 JP2019531624A JP2019531624A JP2020511412A5 JP 2020511412 A5 JP2020511412 A5 JP 2020511412A5 JP 2019531624 A JP2019531624 A JP 2019531624A JP 2019531624 A JP2019531624 A JP 2019531624A JP 2020511412 A5 JP2020511412 A5 JP 2020511412A5
- Authority
- JP
- Japan
- Prior art keywords
- spiro
- piperidine
- carboxamide
- quinolyl
- chroman
- Prior art date
- 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.)
- Granted
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- -1 1-Methyl-6-isoquinolyl Chemical group 0.000 claims 120
- 125000003003 spiro group Chemical group 0.000 claims 25
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 16
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 12
- ZPKJBVIFUSGFLJ-UHFFFAOYSA-N spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound N1(CCC2(CC1)OC1=CC=CC=C1CC2)C(=O)N ZPKJBVIFUSGFLJ-UHFFFAOYSA-N 0.000 claims 12
- IDKWKFTXXFZPQK-UHFFFAOYSA-N spiro[3,4-dihydrochromene-2,4'-piperidine] Chemical compound C1CNCCC21OC1=CC=CC=C1CC2 IDKWKFTXXFZPQK-UHFFFAOYSA-N 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 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 5
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 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
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 230000000561 anti-psychotic effect Effects 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- UXUIBUJCFRKDTO-UHFFFAOYSA-N spiro[3h-1-benzofuran-2,4'-piperidine]-1'-carboxamide Chemical compound C1CN(C(=O)N)CCC11OC2=CC=CC=C2C1 UXUIBUJCFRKDTO-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
- 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
- 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
- HQZKZLSBSXALRZ-UHFFFAOYSA-N 1-[6-(5-methylimidazo[1,2-a]pyridin-6-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-yl]propan-1-one Chemical compound CCC(=O)N1CCC2(CC1)CCc1cc(ccc1O2)-c1ccc2nccn2c1C HQZKZLSBSXALRZ-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
- 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 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
- OCVXSFKKWXMYPF-UHFFFAOYSA-N 2-chloroimidazole Chemical compound ClC1=NC=CN1 OCVXSFKKWXMYPF-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
- TYHZPQIIWZXODF-UHFFFAOYSA-N 5-(4-methylquinolin-3-yl)spiro[3H-1-benzofuran-2,4'-piperidine] Chemical compound CC1=C(C=NC2=CC=CC=C12)C=1C=CC2=C(CC3(CCNCC3)O2)C=1 TYHZPQIIWZXODF-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
- XQIIQWXAXPZDJN-UHFFFAOYSA-N 5-(7-methylpyrazolo[1,5-a]pyridin-6-yl)spiro[3H-1-benzofuran-2,4'-piperidine] Chemical compound Cc1c(ccc2ccnn12)-c1ccc2OC3(Cc2c1)CCNCC3 XQIIQWXAXPZDJN-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
- FVJODJYTITYLGK-UHFFFAOYSA-N 5-(8-methoxyquinolin-7-yl)spiro[3H-1-benzofuran-2,4'-piperidine] Chemical compound COC=1C(=CC=C2C=CC=NC=12)C=1C=CC2=C(CC3(CCNCC3)O2)C=1 FVJODJYTITYLGK-UHFFFAOYSA-N 0.000 claims 1
- JLTKVXOAYOSQSK-UHFFFAOYSA-N 5-(8-methylquinolin-7-yl)spiro[3H-1-benzofuran-2,4'-piperidine] Chemical compound CC=1C(=CC=C2C=CC=NC=12)C=1C=CC2=C(CC3(CCNCC3)O2)C=1 JLTKVXOAYOSQSK-UHFFFAOYSA-N 0.000 claims 1
- DUOBKZMDHNGONA-UHFFFAOYSA-N 5-fluoro-6-(1-methylisoquinolin-6-yl)spiro[3,4-dihydrochromene-2,4'-piperidine] Chemical compound Cc1nccc2cc(ccc12)-c1ccc2OC3(CCNCC3)CCc2c1F DUOBKZMDHNGONA-UHFFFAOYSA-N 0.000 claims 1
- OVXYNIWJOLBVQC-UHFFFAOYSA-N 6-(1-benzofuran-2-yl)spiro[3,4-dihydrochromene-2,4'-piperidine] Chemical compound O1C(=CC2=C1C=CC=C2)C=1C=C2CCC3(CCNCC3)OC2=CC=1 OVXYNIWJOLBVQC-UHFFFAOYSA-N 0.000 claims 1
- LRKGJEQDFKNONY-UHFFFAOYSA-N 6-(1-methylindol-5-yl)spiro[3,4-dihydrochromene-2,4'-piperidine] Chemical compound CN1C=CC2=CC(=CC=C12)C=1C=C2CCC3(CCNCC3)OC2=CC=1 LRKGJEQDFKNONY-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
- HCCQXPPAOUUZIH-UHFFFAOYSA-N 6-(1-methylisoquinolin-6-yl)spiro[3,4-dihydrochromene-2,4'-piperidine] Chemical compound CC1=NC=CC2=CC(=CC=C12)C=1C=C2CCC3(CCNCC3)OC2=CC=1 HCCQXPPAOUUZIH-UHFFFAOYSA-N 0.000 claims 1
- LQFDPBNNDIIMNK-UHFFFAOYSA-N 6-(1-methylisoquinolin-6-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine] Chemical compound Cc1nccc2cc(ccc12)-c1ccc2OC3(CCNCC3)OCc2c1 LQFDPBNNDIIMNK-UHFFFAOYSA-N 0.000 claims 1
- KDPRYCRYUBKSIB-UHFFFAOYSA-N 6-(1H-indol-3-yl)spiro[3,4-dihydrochromene-2,4'-piperidine] Chemical compound N1C=C(C2=CC=CC=C12)C=1C=C2CCC3(CCNCC3)OC2=CC=1 KDPRYCRYUBKSIB-UHFFFAOYSA-N 0.000 claims 1
- PJVLJRQOMDYHOU-UHFFFAOYSA-N 6-(1H-indol-3-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine] Chemical compound C1CC2(CCN1)OCc1cc(ccc1O2)-c1c[nH]c2ccccc12 PJVLJRQOMDYHOU-UHFFFAOYSA-N 0.000 claims 1
- RFALSXHBFNTBER-UHFFFAOYSA-N 6-(3-methylisoquinolin-6-yl)spiro[3,4-dihydrochromene-2,4'-piperidine] Chemical compound CC=1N=CC2=CC=C(C=C2C=1)C=1C=C2CCC3(CCNCC3)OC2=CC=1 RFALSXHBFNTBER-UHFFFAOYSA-N 0.000 claims 1
- DXQBRBYSJIXMFA-UHFFFAOYSA-N 6-(4-methylquinolin-3-yl)spiro[3,4-dihydrochromene-2,4'-piperidine] Chemical compound CC1=C(C=NC2=CC=CC=C12)C=1C=C2CCC3(CCNCC3)OC2=CC=1 DXQBRBYSJIXMFA-UHFFFAOYSA-N 0.000 claims 1
- SHNTWTPCHTUAQC-UHFFFAOYSA-N 6-(4-methylquinolin-3-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine] Chemical compound CC1=C(C=NC2=CC=CC=C12)C1=CC2=C(OC3(CCNCC3)OC2)C=C1 SHNTWTPCHTUAQC-UHFFFAOYSA-N 0.000 claims 1
- NDLJDWLULCJDIU-UHFFFAOYSA-N 6-(7-methylpyrazolo[1,5-a]pyridin-6-yl)spiro[3,4-dihydrochromene-2,4'-piperidine] Chemical compound Cc1c(ccc2ccnn12)-c1ccc2OC3(CCNCC3)CCc2c1 NDLJDWLULCJDIU-UHFFFAOYSA-N 0.000 claims 1
- UAVOJYDHGPZCKW-UHFFFAOYSA-N 6-(8-chloroquinolin-7-yl)-N-ethoxyspiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide Chemical compound CCONC(=O)N1CCC2(CC1)OCc1cc(ccc1O2)-c1ccc2cccnc2c1Cl UAVOJYDHGPZCKW-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
- DZGKKIOGQFTMDV-UHFFFAOYSA-N 6-(8-chloroquinolin-7-yl)spiro[3,4-dihydrochromene-2,4'-piperidine] Chemical compound ClC=1C(=CC=C2C=CC=NC=12)C=1C=C2CCC3(CCNCC3)OC2=CC=1 DZGKKIOGQFTMDV-UHFFFAOYSA-N 0.000 claims 1
- FKHWBGRXYAKJAM-UHFFFAOYSA-N 6-(8-chloroquinolin-7-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine] Chemical compound ClC=1C(=CC=C2C=CC=NC=12)C1=CC2=C(OC3(CCNCC3)OC2)C=C1 FKHWBGRXYAKJAM-UHFFFAOYSA-N 0.000 claims 1
- POZMQLAYQQNGHH-UHFFFAOYSA-N 6-(8-methoxyquinolin-7-yl)spiro[3,4-dihydrochromene-2,4'-piperidine] Chemical compound COC=1C(=CC=C2C=CC=NC=12)C=1C=C2CCC3(CCNCC3)OC2=CC=1 POZMQLAYQQNGHH-UHFFFAOYSA-N 0.000 claims 1
- PPIUKOQHEQKKSG-UHFFFAOYSA-N 6-(8-methoxyquinolin-7-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine] Chemical compound COc1c(ccc2cccnc12)-c1ccc2OC3(CCNCC3)OCc2c1 PPIUKOQHEQKKSG-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
- WIUHGYTZBJXVFR-UHFFFAOYSA-N 6-(8-methylquinolin-7-yl)spiro[3,4-dihydrochromene-2,4'-piperidine] Chemical compound CC=1C(=CC=C2C=CC=NC=12)C=1C=C2CCC3(CCNCC3)OC2=CC=1 WIUHGYTZBJXVFR-UHFFFAOYSA-N 0.000 claims 1
- XJXZYSJSPHDXAM-UHFFFAOYSA-N 6-(8-methylquinolin-7-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine] Chemical compound Cc1c(ccc2cccnc12)-c1ccc2OC3(CCNCC3)OCc2c1 XJXZYSJSPHDXAM-UHFFFAOYSA-N 0.000 claims 1
- OGJNYXKNYWTWAE-UHFFFAOYSA-N 6-isoquinolin-3-yl-N-(oxan-2-yloxy)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound C1=NC(=CC2=CC=CC=C12)C=1C=C2CCC3(CCN(CC3)C(=O)NOC3OCCCC3)OC2=CC=1 OGJNYXKNYWTWAE-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
- FNYUVMQXNBOHBU-UHFFFAOYSA-N 6-isoquinolin-3-ylspiro[4H-1,3-benzodioxine-2,4'-piperidine] Chemical compound C1CC2(CCN1)OCc1cc(ccc1O2)-c1cc2ccccc2cn1 FNYUVMQXNBOHBU-UHFFFAOYSA-N 0.000 claims 1
- YOVBBTXYDZUBFN-UHFFFAOYSA-N 6-thieno[2,3-b]pyridin-5-ylspiro[3,4-dihydrochromene-2,4'-piperidine]-1'-carboxamide Chemical compound S1C=CC=2C1=NC=C(C=2)C=1C=C2CCC3(CCN(CC3)C(=O)N)OC2=CC=1 YOVBBTXYDZUBFN-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
- WHAJVUDBUCPMNE-UHFFFAOYSA-N 7-(8-methylquinolin-7-yl)spiro[4,5-dihydro-1,3-benzodioxepine-2,4'-piperidine] Chemical compound Cc1c(ccc2cccnc12)-c1ccc2OC3(CCNCC3)OCCc2c1 WHAJVUDBUCPMNE-UHFFFAOYSA-N 0.000 claims 1
- WANBIFTYZHKRKM-UHFFFAOYSA-N 7-fluoro-6-(1-methylisoquinolin-6-yl)spiro[3,4-dihydrochromene-2,4'-piperidine] Chemical compound FC1=C(C=C2CCC3(CCNCC3)OC2=C1)C=1C=C2C=CN=C(C2=CC=1)C WANBIFTYZHKRKM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- CWKLTLCHXRBTLG-UHFFFAOYSA-N CC1=NC=CC2=C1C=CC(=C2)C3=CC4=C(C=C3)OC5(CC4)CCN(CC5)OC(C)C Chemical compound CC1=NC=CC2=C1C=CC(=C2)C3=CC4=C(C=C3)OC5(CC4)CCN(CC5)OC(C)C CWKLTLCHXRBTLG-UHFFFAOYSA-N 0.000 claims 1
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- 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
- ODORWARUGMYXOU-UHFFFAOYSA-N N-hydroxy-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)NO)OC2=CC=1 ODORWARUGMYXOU-UHFFFAOYSA-N 0.000 claims 1
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- 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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- YERJYWJGCQPONY-UHFFFAOYSA-N [2-[6-(8-chloroquinolin-7-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-yl]-2-oxoethyl] acetate Chemical compound C(C)(=O)OCC(=O)N1CCC2(CC1)OC1=CC=C(C=C1CC2)C1=CC=C2C=CC=NC2=C1Cl YERJYWJGCQPONY-UHFFFAOYSA-N 0.000 claims 1
- FUSOKXVXXBINOX-UHFFFAOYSA-N [2-[6-(8-methylquinolin-7-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-yl]-2-oxoethyl] acetate Chemical compound CC(=O)OCC(=O)N1CCC2(CC1)OCc1cc(ccc1O2)-c1ccc2cccnc2c1C FUSOKXVXXBINOX-UHFFFAOYSA-N 0.000 claims 1
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- 239000002253 acid Substances 0.000 claims 1
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- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- AUQYCFIWDTVLHD-UHFFFAOYSA-N cyclobutyl-(6-quinolin-3-ylspiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-yl)methanone Chemical compound O=C(C1CCC1)N1CCC2(CC1)OCc1cc(ccc1O2)-c1cnc2ccccc2c1 AUQYCFIWDTVLHD-UHFFFAOYSA-N 0.000 claims 1
- XTIHTUDCFNABQA-UHFFFAOYSA-N cyclobutyl-(6-quinolin-3-ylspiro[chromene-2,4'-piperidine]-1'-yl)methanone Chemical compound C1(CCC1)C(=O)N1CCC2(CC1)OC1=CC=C(C=C1C=C2)C=1C=NC2=CC=CC=C2C=1 XTIHTUDCFNABQA-UHFFFAOYSA-N 0.000 claims 1
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- MONCVWRHYIWAPR-UHFFFAOYSA-N cyclopropyl-[6-(1-methylisoquinolin-6-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-yl]methanone Chemical compound C1(CC1)C(=O)N1CCC2(CC1)OC1=CC=C(C=C1CC2)C=1C=C2C=CN=C(C2=CC=1)C MONCVWRHYIWAPR-UHFFFAOYSA-N 0.000 claims 1
- OWMYGJGYCILYAD-UHFFFAOYSA-N cyclopropyl-[6-(8-methoxyquinolin-7-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-yl]methanone Chemical compound C1(CC1)C(=O)N1CCC2(CC1)OC1=CC=C(C=C1CC2)C1=CC=C2C=CC=NC2=C1OC OWMYGJGYCILYAD-UHFFFAOYSA-N 0.000 claims 1
- HZMPCVDTHUIMCH-UHFFFAOYSA-N cyclopropyl-[6-(8-methylquinolin-6-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-yl]methanone Chemical compound C1(CC1)C(=O)N1CCC2(CC1)OC1=CC=C(C=C1CC2)C=1C=C2C=CC=NC2=C(C=1)C HZMPCVDTHUIMCH-UHFFFAOYSA-N 0.000 claims 1
- GBOOLCCFGYYBMT-UHFFFAOYSA-N cyclopropyl-[6-(8-methylquinolin-7-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-yl]methanone Chemical compound Cc1c(ccc2cccnc12)-c1ccc2OC3(CCN(CC3)C(=O)C3CC3)OCc2c1 GBOOLCCFGYYBMT-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 238000002651 drug therapy Methods 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- UTWGRMYWDUMKNY-UHFFFAOYSA-N indole-1-carboxylic acid Chemical compound C1=CC=C2N(C(=O)O)C=CC2=C1 UTWGRMYWDUMKNY-UHFFFAOYSA-N 0.000 claims 1
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- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 claims 1
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| EP3554637A4 (en) * | 2016-12-14 | 2020-05-20 | 89Bio Ltd. | SPIROPIPERID DERIVATIVES |
| HU231333B1 (hu) * | 2018-07-13 | 2023-01-28 | Richter Gedeon Nyrt | Spirokromán származékok |
| HU231414B1 (hu) | 2018-07-13 | 2023-08-28 | Richter Gedeon Nyrt. | Tiadiazin származékok |
| TWI767148B (zh) | 2018-10-10 | 2022-06-11 | 美商弗瑪治療公司 | 抑制脂肪酸合成酶(fasn) |
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| EP0683782A4 (en) | 1993-02-12 | 1996-03-27 | Merck & Co Inc | SPIRO (2H-1-BENZOPYRAN-2,4-PIPERIDINE) AS CLASS III ANTI-ARRHYTHMIC. |
| BRPI0613427A2 (pt) | 2005-07-19 | 2012-10-30 | Merck & Co Inc | composto ou seu sal ou éster, composição farmacêutica, agente terapêutico, e , uso do composto ou seu sal ou éster |
| AR057570A1 (es) | 2005-11-14 | 2007-12-05 | Solvay Pharm Gmbh | Derivados de n-sulfamoil-n'-benzopiranopiperidinas espirocondensadas, composiciones farmaceuticas que los comprenden, un procedimiento para su preparacion y su uso en la preparacion de medicamentos para el tratamiento de enfermedades mediadas por las isoenzimas anhidrasas carbonicas subtipos ii y/o |
| AU2006313725A1 (en) | 2005-11-14 | 2007-05-18 | Solvay Pharmaceuticals Gmbh | N-sulfamoyl-N'-benzopyranpiperidines as inhbitors of carbonic anhydrases |
| AU2008205642B2 (en) | 2007-01-12 | 2013-06-06 | Msd K.K. | Spirochromanon derivatives |
| PE20081559A1 (es) | 2007-01-12 | 2008-11-20 | Merck & Co Inc | DERIVADOS DE ESPIROCROMANONA SUSTITUIDOS COMO INHIBIDORES DE ACETIL CoA CARBOXILASA |
| CA2712897A1 (en) | 2008-01-30 | 2009-08-06 | Pharmacopeia, Inc. | Substituted spirocyclic piperidine derivatives as histamine-3 (h3) receptor ligands |
| JP5501256B2 (ja) | 2008-07-04 | 2014-05-21 | Ｍｓｄ株式会社 | 新規スピロクロマノンカルボン酸 |
| TW201300393A (zh) | 2011-05-20 | 2013-01-01 | Kowa Co | 新穎之螺哌啶衍生物及含有其之醫藥 |
| CN103304571B (zh) * | 2012-03-06 | 2018-02-16 | 凯惠科技发展(上海)有限公司 | 螺环化合物、其制备方法、中间体、药物组合物和应用 |
| CN109792272A (zh) | 2016-08-10 | 2019-05-21 | Idac控股公司 | 针对下一代无线系统的空间调制 |
| EP3554637A4 (en) * | 2016-12-14 | 2020-05-20 | 89Bio Ltd. | SPIROPIPERID DERIVATIVES |
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