JPWO2019141808A5 - - Google Patents
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- Publication number
- JPWO2019141808A5 JPWO2019141808A5 JP2020539797A JP2020539797A JPWO2019141808A5 JP WO2019141808 A5 JPWO2019141808 A5 JP WO2019141808A5 JP 2020539797 A JP2020539797 A JP 2020539797A JP 2020539797 A JP2020539797 A JP 2020539797A JP WO2019141808 A5 JPWO2019141808 A5 JP WO2019141808A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- dihydro
- quinazoline
- benzyl
- piperidine
- 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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- 125000001424 substituent group Chemical group 0.000 claims 33
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 15
- 125000003545 alkoxy group Chemical group 0.000 claims 13
- -1 azetidine-1,3-diyl Chemical group 0.000 claims 13
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 208000035475 disorder Diseases 0.000 claims 7
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 230000002265 prevention Effects 0.000 claims 6
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 4
- 208000027866 inflammatory disease Diseases 0.000 claims 4
- 208000014674 injury Diseases 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000006494 2-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 208000027418 Wounds and injury Diseases 0.000 claims 2
- 230000006378 damage Effects 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 208000019553 vascular disease Diseases 0.000 claims 2
- ZWWXEGGGSITMJD-UHFFFAOYSA-N 1,3-dimethyl-5-[4-[2-oxo-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-3-yl]piperidin-1-yl]pyrazole-4-carbonitrile Chemical compound CN1N=C(C(=C1N1CCC(CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)C(F)(F)F)=O)C#N)C ZWWXEGGGSITMJD-UHFFFAOYSA-N 0.000 claims 1
- MXCBRVWOFUZCQN-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-3-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-4H-quinazolin-2-one Chemical compound ClC1=C(CN2C(N(CC3=CC=CC=C23)C2CCN(CC2)C2=C(C=CC=C2C)F)=O)C=CC=C1 MXCBRVWOFUZCQN-UHFFFAOYSA-N 0.000 claims 1
- ROULNWHEFOIYHD-UHFFFAOYSA-N 1-[(2-cyclobutyloxyphenyl)methyl]-3-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-4H-quinazolin-2-one Chemical compound C1(CCC1)OC1=C(CN2C(N(CC3=CC=CC=C23)C2CCN(CC2)C2=C(C=CC=C2C)F)=O)C=CC=C1 ROULNWHEFOIYHD-UHFFFAOYSA-N 0.000 claims 1
- BQXOWWKUXNMIGH-UHFFFAOYSA-N 1-[(2-cyclopropyloxyphenyl)methyl]-3-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-4H-quinazolin-2-one Chemical compound C1(CC1)OC1=C(CN2C(N(CC3=CC=CC=C23)C2CCN(CC2)C2=C(C=CC=C2C)F)=O)C=CC=C1 BQXOWWKUXNMIGH-UHFFFAOYSA-N 0.000 claims 1
- VONVZIBWIUKDKS-UHFFFAOYSA-N 1-[(2-ethoxyphenyl)methyl]-3-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-4H-quinazolin-2-one Chemical compound C(C)OC1=C(CN2C(N(CC3=CC=CC=C23)C2CCN(CC2)C2=C(C=CC=C2C)F)=O)C=CC=C1 VONVZIBWIUKDKS-UHFFFAOYSA-N 0.000 claims 1
- MFISIQPKTILCSC-UHFFFAOYSA-N 1-[[2-(cyclopropylmethoxy)phenyl]methyl]-3-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-4H-quinazolin-2-one Chemical compound C1(CC1)COC1=C(CN2C(N(CC3=CC=CC=C23)C2CCN(CC2)C2=C(C=CC=C2C)F)=O)C=CC=C1 MFISIQPKTILCSC-UHFFFAOYSA-N 0.000 claims 1
- ODEVORZVJQIQDL-UHFFFAOYSA-N 1-[[2-[2-(dimethylamino)ethoxy]phenyl]methyl]-3-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-4H-quinazolin-2-one Chemical compound CN(CCOC1=C(CN2C(N(CC3=CC=CC=C23)C2CCN(CC2)C2=C(C=CC=C2C)F)=O)C=CC=C1)C ODEVORZVJQIQDL-UHFFFAOYSA-N 0.000 claims 1
- IUTHEOCJFAFDRT-BNEYPBHNSA-N 1-[[2-deuterio-6-(trifluoromethyl)phenyl]methyl]-3-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-4H-quinazolin-2-one Chemical compound FC(C=1C=CC=C(C=1CN1C(N(CC2=CC=CC=C12)C1CCN(CC1)C1=C(C=CC=C1C)F)=O)[2H])(F)F IUTHEOCJFAFDRT-BNEYPBHNSA-N 0.000 claims 1
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims 1
- NBAQMUNWXMJMOP-UHFFFAOYSA-N 2-[2-[[3-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-2-oxo-4H-quinazolin-1-yl]methyl]phenoxy]acetonitrile Chemical compound FC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(OCC#N)C=CC=C1)=O NBAQMUNWXMJMOP-UHFFFAOYSA-N 0.000 claims 1
- SMKLEDNDBVGHCV-UHFFFAOYSA-N 2-[2-[[3-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-2-oxo-4H-quinazolin-1-yl]methyl]phenoxy]ethyl acetate Chemical compound FC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(OCCOC(C)=O)C=CC=C1)=O SMKLEDNDBVGHCV-UHFFFAOYSA-N 0.000 claims 1
- MVALVRKWRZKPPO-JOCHJYFZSA-N 3-[(3R)-1-(2,4-dimethylpyridin-3-yl)pyrrolidin-3-yl]-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound CC1=NC=CC(=C1N1C[C@@H](CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)C(F)(F)F)=O)C MVALVRKWRZKPPO-JOCHJYFZSA-N 0.000 claims 1
- IXWZFXSOBMYKBS-LJQANCHMSA-N 3-[(3R)-1-(2,6-difluorophenyl)pyrrolidin-3-yl]-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound FC1=C(C(=CC=C1)F)N1C[C@@H](CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)C(F)(F)F)=O IXWZFXSOBMYKBS-LJQANCHMSA-N 0.000 claims 1
- IDLDOHAQPIPZJO-LJQANCHMSA-N 3-[(3R)-1-(2,6-difluorophenyl)pyrrolidin-3-yl]-8-methoxy-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound FC1=C(C(=CC=C1)F)N1C[C@@H](CC1)N1C(N(C2=C(C=CC=C2C1)OC)CC1=C(C=CC=C1)C(F)(F)F)=O IDLDOHAQPIPZJO-LJQANCHMSA-N 0.000 claims 1
- KNINFMMVCYMPGJ-OAQYLSRUSA-N 3-[(3R)-1-(2,6-dimethoxyphenyl)pyrrolidin-3-yl]-8-methoxy-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound COC1=C(C(=CC=C1)OC)N1C[C@@H](CC1)N1C(N(C2=C(C=CC=C2C1)OC)CC1=C(C=CC=C1)C(F)(F)F)=O KNINFMMVCYMPGJ-OAQYLSRUSA-N 0.000 claims 1
- CUHUVIUZGKYVMC-XMMPIXPASA-N 3-[(3R)-1-(2,6-dimethylphenyl)pyrrolidin-3-yl]-1-[(2-methoxyphenyl)methyl]-4H-quinazolin-2-one Chemical compound CC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)OC)=O CUHUVIUZGKYVMC-XMMPIXPASA-N 0.000 claims 1
- WKDINXKCGOAGPJ-HSZRJFAPSA-N 3-[(3R)-1-(2,6-dimethylphenyl)pyrrolidin-3-yl]-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound CC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)C(F)(F)F)=O WKDINXKCGOAGPJ-HSZRJFAPSA-N 0.000 claims 1
- ZLKLYTGXTUOQGL-HSZRJFAPSA-N 3-[(3R)-1-(2,6-dimethylphenyl)pyrrolidin-3-yl]-8-methoxy-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound CC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C(C=CC=C2C1)OC)CC1=C(C=CC=C1)C(F)(F)F)=O ZLKLYTGXTUOQGL-HSZRJFAPSA-N 0.000 claims 1
- NPRDJVCRYIYEDB-HXUWFJFHSA-N 3-[(3R)-1-(2-fluoro-4-methylpyridin-3-yl)pyrrolidin-3-yl]-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound FC1=NC=CC(=C1N1C[C@@H](CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)C(F)(F)F)=O)C NPRDJVCRYIYEDB-HXUWFJFHSA-N 0.000 claims 1
- VJWRZIKFISVDPM-HXUWFJFHSA-N 3-[(3R)-1-(2-fluoro-6-methoxyphenyl)pyrrolidin-3-yl]-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound FC1=C(C(=CC=C1)OC)N1C[C@@H](CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)C(F)(F)F)=O VJWRZIKFISVDPM-HXUWFJFHSA-N 0.000 claims 1
- HRPTYAYGHJGXTP-HXUWFJFHSA-N 3-[(3R)-1-(2-fluoro-6-methoxyphenyl)pyrrolidin-3-yl]-8-methoxy-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound FC1=C(C(=CC=C1)OC)N1C[C@@H](CC1)N1C(N(C2=C(C=CC=C2C1)OC)CC1=C(C=CC=C1)C(F)(F)F)=O HRPTYAYGHJGXTP-HXUWFJFHSA-N 0.000 claims 1
- MOGWOIFYBDUYGR-JOCHJYFZSA-N 3-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-1-[(2-methoxyphenyl)methyl]-4H-quinazolin-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)OC)=O MOGWOIFYBDUYGR-JOCHJYFZSA-N 0.000 claims 1
- YAPJCZSNWUNHRK-OAQYLSRUSA-N 3-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)C(F)(F)F)=O YAPJCZSNWUNHRK-OAQYLSRUSA-N 0.000 claims 1
- APFNSAAIJMORBR-OAQYLSRUSA-N 3-[(3R)-1-(2-methoxy-4-methylpyridin-3-yl)pyrrolidin-3-yl]-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound COC1=NC=CC(=C1N1C[C@@H](CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)C(F)(F)F)=O)C APFNSAAIJMORBR-OAQYLSRUSA-N 0.000 claims 1
- YUWWNJUYTSABNE-JOCHJYFZSA-N 3-[(3R)-1-(2-methoxy-6-methylphenyl)pyrrolidin-3-yl]-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound COC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)C(F)(F)F)=O YUWWNJUYTSABNE-JOCHJYFZSA-N 0.000 claims 1
- GZXPMBCGRLEEGF-OAQYLSRUSA-N 3-[(3R)-1-(2-methoxyphenyl)pyrrolidin-3-yl]-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound COC1=C(C=CC=C1)N1C[C@@H](CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)C(F)(F)F)=O GZXPMBCGRLEEGF-OAQYLSRUSA-N 0.000 claims 1
- IXWZFXSOBMYKBS-IBGZPJMESA-N 3-[(3S)-1-(2,6-difluorophenyl)pyrrolidin-3-yl]-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound FC1=C(C(=CC=C1)F)N1C[C@H](CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)C(F)(F)F)=O IXWZFXSOBMYKBS-IBGZPJMESA-N 0.000 claims 1
- WKDINXKCGOAGPJ-QHCPKHFHSA-N 3-[(3S)-1-(2,6-dimethylphenyl)pyrrolidin-3-yl]-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound CC1=C(C(=CC=C1)C)N1C[C@H](CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)C(F)(F)F)=O WKDINXKCGOAGPJ-QHCPKHFHSA-N 0.000 claims 1
- VJWRZIKFISVDPM-FQEVSTJZSA-N 3-[(3S)-1-(2-fluoro-6-methoxyphenyl)pyrrolidin-3-yl]-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound FC1=C(C(=CC=C1)OC)N1C[C@H](CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)C(F)(F)F)=O VJWRZIKFISVDPM-FQEVSTJZSA-N 0.000 claims 1
- GZXPMBCGRLEEGF-NRFANRHFSA-N 3-[(3S)-1-(2-methoxyphenyl)pyrrolidin-3-yl]-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound COC1=C(C=CC=C1)N1C[C@H](CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)C(F)(F)F)=O GZXPMBCGRLEEGF-NRFANRHFSA-N 0.000 claims 1
- OQQTYPFJRNAVCU-UHFFFAOYSA-N 3-[1-(2,6-difluorophenyl)piperidin-4-yl]-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound FC1=C(C(=CC=C1)F)N1CCC(CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)C(F)(F)F)=O OQQTYPFJRNAVCU-UHFFFAOYSA-N 0.000 claims 1
- PZYBSYOMHQMXGL-UHFFFAOYSA-N 3-[1-(2,6-dimethylphenyl)piperidin-4-yl]-1-[(2-methoxyphenyl)methyl]-4H-quinazolin-2-one Chemical compound CC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)OC)=O PZYBSYOMHQMXGL-UHFFFAOYSA-N 0.000 claims 1
- ZGSPTRGIBCWWRQ-UHFFFAOYSA-N 3-[1-(2,6-dimethylphenyl)piperidin-4-yl]-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound CC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)C(F)(F)F)=O ZGSPTRGIBCWWRQ-UHFFFAOYSA-N 0.000 claims 1
- LMZFFQWZRMWDJL-UHFFFAOYSA-N 3-[1-(2,6-dimethylphenyl)piperidin-4-yl]-8-methoxy-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound CC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=C(C=CC=C2C1)OC)CC1=C(C=CC=C1)C(F)(F)F)=O LMZFFQWZRMWDJL-UHFFFAOYSA-N 0.000 claims 1
- LKWNQRUJDBWFPC-UHFFFAOYSA-N 3-[1-(2-chloro-6-methylphenyl)piperidin-4-yl]-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound ClC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)C(F)(F)F)=O LKWNQRUJDBWFPC-UHFFFAOYSA-N 0.000 claims 1
- ZXGMCLXGAIDBJH-UHFFFAOYSA-N 3-[1-(2-fluoro-6-methoxyphenyl)piperidin-4-yl]-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound FC1=C(C(=CC=C1)OC)N1CCC(CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)C(F)(F)F)=O ZXGMCLXGAIDBJH-UHFFFAOYSA-N 0.000 claims 1
- JSCPXKOAEFZLBG-UHFFFAOYSA-N 3-[1-(2-fluoro-6-methoxyphenyl)piperidin-4-yl]-8-methoxy-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound FC1=C(C(=CC=C1)OC)N1CCC(CC1)N1C(N(C2=C(C=CC=C2C1)OC)CC1=C(C=CC=C1)C(F)(F)F)=O JSCPXKOAEFZLBG-UHFFFAOYSA-N 0.000 claims 1
- YIJVDIMJLAYCLF-UHFFFAOYSA-N 3-[1-(2-fluoro-6-methylphenyl)azepan-4-yl]-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CCC(CCC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)C(F)(F)F)=O YIJVDIMJLAYCLF-UHFFFAOYSA-N 0.000 claims 1
- MKGKQOGGQJXJJF-UHFFFAOYSA-N 3-[1-(2-fluoro-6-methylphenyl)azetidin-3-yl]-1-[[2-(trifluoromethyl)phenyl]methyl]-4H-quinazolin-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CC(C1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)C(F)(F)F)=O MKGKQOGGQJXJJF-UHFFFAOYSA-N 0.000 claims 1
- NYTGFQSTUXRTNM-UHFFFAOYSA-N 3-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-1-[(2-methoxyphenyl)methyl]-4H-quinazolin-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)OC)=O NYTGFQSTUXRTNM-UHFFFAOYSA-N 0.000 claims 1
- SEANTEBEHGMFEL-UHFFFAOYSA-N 3-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-1-[(2-propan-2-yloxyphenyl)methyl]-4H-quinazolin-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)OC(C)C)=O SEANTEBEHGMFEL-UHFFFAOYSA-N 0.000 claims 1
- JPTMBHWPALEFPA-UHFFFAOYSA-N 3-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-1-[(2-propan-2-ylphenyl)methyl]-4H-quinazolin-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=CC=CC=C2C1)CC1=C(C=CC=C1)C(C)C)=O JPTMBHWPALEFPA-UHFFFAOYSA-N 0.000 claims 1
- FQEBGPVKNUVGKY-UHFFFAOYSA-N 3-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-1-[(3-methoxypyrazin-2-yl)methyl]-4H-quinazolin-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=CC=CC=C2C1)CC1=NC=CN=C1OC)=O FQEBGPVKNUVGKY-UHFFFAOYSA-N 0.000 claims 1
- RWPISPUGJCEEFD-UHFFFAOYSA-N 3-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-1-[(3-propan-2-yloxypyrazin-2-yl)methyl]-4H-quinazolin-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=CC=CC=C2C1)CC1=NC=CN=C1OC(C)C)=O RWPISPUGJCEEFD-UHFFFAOYSA-N 0.000 claims 1
- BHEKIVOPJRWULV-UHFFFAOYSA-N 3-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-1-[(3-propan-2-yloxypyridin-2-yl)methyl]-4H-quinazolin-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=CC=CC=C2C1)CC1=NC=CC=C1OC(C)C)=O BHEKIVOPJRWULV-UHFFFAOYSA-N 0.000 claims 1
- YFLKLLNVZNVRMO-UHFFFAOYSA-N 3-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-1-[(3-propan-2-ylpyrazin-2-yl)methyl]-4H-quinazolin-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=CC=CC=C2C1)CC1=NC=CN=C1C(C)C)=O YFLKLLNVZNVRMO-UHFFFAOYSA-N 0.000 claims 1
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| US7834000B2 (en) | 2006-06-13 | 2010-11-16 | Vertex Pharmaceuticals Incorporated | CGRP receptor antagonists |
| CA2656507C (en) | 2006-07-17 | 2012-03-20 | Amgen Inc. | Quinazoline and pyridopyrimidine derivatives as p38 kinase inhibitors |
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| JP6417419B2 (ja) | 2013-09-04 | 2018-11-07 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | 免疫調節剤として有用な化合物 |
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| WO2015044900A1 (en) | 2013-09-27 | 2015-04-02 | Aurigene Discovery Technologies Limited | Therapeutic immunomodulating compounds |
| JO3789B1 (ar) * | 2015-03-13 | 2021-01-31 | Resverlogix Corp | التراكيب والوسائل العلاجية المعتمدة لمعالجة الامراض المتعلقة بالمتممة |
| EP3737684B1 (en) | 2018-01-10 | 2022-11-16 | Idorsia Pharmaceuticals Ltd | 2,4,6,7-tetrahydro-pyrazolo[4,3-d]pyrimidin-5-one derivatives and related compounds as c5a receptor modulators for treating vasculitis and inflammatory diseases |
| CA3087886A1 (en) | 2018-01-19 | 2019-07-25 | Idorsia Pharmaceuticals Ltd | C5a receptor modulators |
| US11685729B2 (en) | 2018-01-19 | 2023-06-27 | Idorsia Pharmaceuticals Ltd. | C5a receptor modulators |
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