JP2016510783A5 - - Google Patents
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- Publication number
- JP2016510783A5 JP2016510783A5 JP2015562111A JP2015562111A JP2016510783A5 JP 2016510783 A5 JP2016510783 A5 JP 2016510783A5 JP 2015562111 A JP2015562111 A JP 2015562111A JP 2015562111 A JP2015562111 A JP 2015562111A JP 2016510783 A5 JP2016510783 A5 JP 2016510783A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyridin
- methylsulfonyl
- piperazin
- furo
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 31
- 150000003839 salts Chemical class 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 16
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 14
- 125000002947 alkylene group Chemical group 0.000 claims 12
- 229910052799 carbon Inorganic materials 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- -1 3-((pyridin-2-ylmethyl) amino) phenyl Chemical group 0.000 claims 9
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- FYNCIYHECMWXPK-UHFFFAOYSA-N 5h-furo[3,2-c]pyridin-4-one Chemical compound O=C1NC=CC2=C1C=CO2 FYNCIYHECMWXPK-UHFFFAOYSA-N 0.000 claims 2
- 229940125763 bromodomain inhibitor Drugs 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000003566 oxetanyl group Chemical group 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- SKWUKCZJCFEDGL-UHFFFAOYSA-N 2-(1,4-diazepan-1-ylmethyl)-5-methyl-7-[2-(pyridin-2-ylmethylamino)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C1=2OC(CN3CCNCCC3)=CC=2C(=O)N(C)C=C1C(C=1)=CC=NC=1NCC1=CC=CC=N1 SKWUKCZJCFEDGL-UHFFFAOYSA-N 0.000 claims 1
- VVULLKQYMRSJHE-UHFFFAOYSA-N 2-(1,4-diazepan-1-ylmethyl)-7-(3,4-dimethoxyphenyl)-5-methylfuro[3,2-c]pyridin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN(C)C(=O)C2=C1OC(CN1CCNCCC1)=C2 VVULLKQYMRSJHE-UHFFFAOYSA-N 0.000 claims 1
- WUQUNDCQNMGOJS-UHFFFAOYSA-N 2-[(2-aminoethylamino)methyl]-7-(3,4-dimethoxyphenyl)-5-methylfuro[3,2-c]pyridin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN(C)C(=O)C2=C1OC(CNCCN)=C2 WUQUNDCQNMGOJS-UHFFFAOYSA-N 0.000 claims 1
- XZBPCZMBXNAIQV-UHFFFAOYSA-N 2-[(3,3-difluoropiperidin-1-yl)methyl]-5-methyl-7-[2-(oxan-4-ylmethoxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C1=2OC(CN3CC(F)(F)CCC3)=CC=2C(=O)N(C)C=C1C(C=1)=CC=NC=1OCC1CCOCC1 XZBPCZMBXNAIQV-UHFFFAOYSA-N 0.000 claims 1
- DDBJXQIYRNMXCR-UHFFFAOYSA-N 2-[(3-fluoropiperidin-1-yl)methyl]-7-(4-methoxyphenyl)-5-methylfuro[3,2-c]pyridin-4-one Chemical compound C1=CC(OC)=CC=C1C1=CN(C)C(=O)C2=C1OC(CN1CC(F)CCC1)=C2 DDBJXQIYRNMXCR-UHFFFAOYSA-N 0.000 claims 1
- KNDSMZOBNSXMJT-UHFFFAOYSA-N 2-[(4-acetyl-2-methylpiperazin-1-yl)methyl]-5-methyl-7-[2-(oxan-4-ylmethoxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one;hydrochloride Chemical compound Cl.CC1CN(C(C)=O)CCN1CC1=CC(C(N(C)C=C2C=3C=C(OCC4CCOCC4)N=CC=3)=O)=C2O1 KNDSMZOBNSXMJT-UHFFFAOYSA-N 0.000 claims 1
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 1
- XGYILSHXIHSUOO-UHFFFAOYSA-N 3-(cyclopropylmethoxy)-4-[5-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-oxofuro[3,2-c]pyridin-7-yl]benzoic acid Chemical compound C1=2OC(CN3CCN(CC3)S(C)(=O)=O)=CC=2C(=O)N(C)C=C1C1=CC=C(C(O)=O)C=C1OCC1CC1 XGYILSHXIHSUOO-UHFFFAOYSA-N 0.000 claims 1
- FDLRRZYLHCNCKI-UHFFFAOYSA-N 5-methyl-2-(morpholin-4-ylmethyl)-7-[2-(oxan-4-ylmethoxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C1=2OC(CN3CCOCC3)=CC=2C(=O)N(C)C=C1C(C=1)=CC=NC=1OCC1CCOCC1 FDLRRZYLHCNCKI-UHFFFAOYSA-N 0.000 claims 1
- LJYRYWKCKYKAET-GOSISDBHSA-N 5-methyl-2-[(1r)-1-(4-methylsulfonylpiperazin-1-yl)ethyl]-7-[2-(oxan-4-ylmethoxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound N1([C@H](C)C=2OC3=C(C(N(C)C=C3C=3C=C(OCC4CCOCC4)N=CC=3)=O)C=2)CCN(S(C)(=O)=O)CC1 LJYRYWKCKYKAET-GOSISDBHSA-N 0.000 claims 1
- LJYRYWKCKYKAET-SFHVURJKSA-N 5-methyl-2-[(1s)-1-(4-methylsulfonylpiperazin-1-yl)ethyl]-7-[2-(oxan-4-ylmethoxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound N1([C@@H](C)C=2OC3=C(C(N(C)C=C3C=3C=C(OCC4CCOCC4)N=CC=3)=O)C=2)CCN(S(C)(=O)=O)CC1 LJYRYWKCKYKAET-SFHVURJKSA-N 0.000 claims 1
- PBNOUWNDUBZSPQ-UHFFFAOYSA-N 5-methyl-2-[(2-methylpiperazin-1-yl)methyl]-7-[2-(oxan-4-ylmethoxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one;hydrochloride Chemical compound Cl.CC1CNCCN1CC1=CC(C(N(C)C=C2C=3C=C(OCC4CCOCC4)N=CC=3)=O)=C2O1 PBNOUWNDUBZSPQ-UHFFFAOYSA-N 0.000 claims 1
- YRTOQQVSMZLXDL-UHFFFAOYSA-N 5-methyl-2-[(4-methyl-1,4-diazepan-1-yl)methyl]-7-[3-(pyridin-2-ylmethylamino)phenyl]furo[3,2-c]pyridin-4-one;hydrochloride Chemical compound Cl.C1CN(C)CCCN1CC1=CC(C(N(C)C=C2C=3C=C(NCC=4N=CC=CC=4)C=CC=3)=O)=C2O1 YRTOQQVSMZLXDL-UHFFFAOYSA-N 0.000 claims 1
- YYLOVEDYTPNZLM-UHFFFAOYSA-N 5-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-7-(3-phenylmethoxyphenyl)furo[3,2-c]pyridin-4-one Chemical compound C1=2OC(CN3CCN(CC3)S(C)(=O)=O)=CC=2C(=O)N(C)C=C1C(C=1)=CC=CC=1OCC1=CC=CC=C1 YYLOVEDYTPNZLM-UHFFFAOYSA-N 0.000 claims 1
- VJSUIISNWBLXEU-UHFFFAOYSA-N 5-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-7-[2-(1-phenylethylamino)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C=1C=CC=CC=1C(C)NC(N=CC=1)=CC=1C(C=1O2)=CN(C)C(=O)C=1C=C2CN1CCN(S(C)(=O)=O)CC1 VJSUIISNWBLXEU-UHFFFAOYSA-N 0.000 claims 1
- LXQMPGUFEUSBHM-UHFFFAOYSA-N 5-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-7-[2-(oxan-4-ylmethoxy)pyridin-4-yl]furo[2,3-d]pyridazin-4-one Chemical compound CN1N=C(C2=C(C1=O)C=C(O2)CN2CCN(CC2)S(=O)(=O)C)C2=CC(=NC=C2)OCC2CCOCC2 LXQMPGUFEUSBHM-UHFFFAOYSA-N 0.000 claims 1
- ORGIADDXKMFHEG-UHFFFAOYSA-N 5-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-7-[2-(oxan-4-ylmethoxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C1=2OC(CN3CCN(CC3)S(C)(=O)=O)=CC=2C(=O)N(C)C=C1C(C=1)=CC=NC=1OCC1CCOCC1 ORGIADDXKMFHEG-UHFFFAOYSA-N 0.000 claims 1
- WEMVJRAJRHBMHP-UHFFFAOYSA-N 5-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-7-[3-(1-phenylethylamino)phenyl]furo[3,2-c]pyridin-4-one Chemical compound C=1C=CC=CC=1C(C)NC(C=1)=CC=CC=1C(C=1O2)=CN(C)C(=O)C=1C=C2CN1CCN(S(C)(=O)=O)CC1 WEMVJRAJRHBMHP-UHFFFAOYSA-N 0.000 claims 1
- FZCIRGODGLUISW-UHFFFAOYSA-N 5-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-7-[5-(1-phenylethoxy)pyridin-3-yl]furo[3,2-c]pyridin-4-one Chemical compound C=1C=CC=CC=1C(C)OC(C=1)=CN=CC=1C(C=1O2)=CN(C)C(=O)C=1C=C2CN1CCN(S(C)(=O)=O)CC1 FZCIRGODGLUISW-UHFFFAOYSA-N 0.000 claims 1
- LJYRYWKCKYKAET-UHFFFAOYSA-N 5-methyl-2-[1-(4-methylsulfonylpiperazin-1-yl)ethyl]-7-[2-(oxan-4-ylmethoxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C=1C(C(N(C)C=C2C=3C=C(OCC4CCOCC4)N=CC=3)=O)=C2OC=1C(C)N1CCN(S(C)(=O)=O)CC1 LJYRYWKCKYKAET-UHFFFAOYSA-N 0.000 claims 1
- DSTYYMIHIUMGID-CYBMUJFWSA-N 5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-7-(2-oxo-1,3-dihydropyrrolo[2,3-b]pyridin-4-yl)furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C=4CC(=O)NC=4N=CC=3)=O)=C2O1 DSTYYMIHIUMGID-CYBMUJFWSA-N 0.000 claims 1
- ANZGHRYXXJSLFU-MRXNPFEDSA-N 5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-7-(3-propan-2-yloxypyridin-4-yl)furo[3,2-c]pyridin-4-one Chemical compound CC(C)OC1=CN=CC=C1C1=CN(C)C(=O)C2=C1OC(CN1[C@@H](CN(CC1)S(C)(=O)=O)C)=C2 ANZGHRYXXJSLFU-MRXNPFEDSA-N 0.000 claims 1
- CZTJIXVUZMIAJF-LJQANCHMSA-N 5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-7-[2-(2-pyrrolidin-1-ylethoxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C=C(OCCN4CCCC4)N=CC=3)=O)=C2O1 CZTJIXVUZMIAJF-LJQANCHMSA-N 0.000 claims 1
- JBFGXWICIPTWHK-GOSISDBHSA-N 5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-7-[2-[2-(2-oxopyrrolidin-1-yl)ethoxy]pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C=C(OCCN4C(CCC4)=O)N=CC=3)=O)=C2O1 JBFGXWICIPTWHK-GOSISDBHSA-N 0.000 claims 1
- ZEXMGFHHBCQZFB-TZHYSIJRSA-N 5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-7-[3-(oxetan-2-ylmethoxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)OCC3OCC3)=O)=C2O1 ZEXMGFHHBCQZFB-TZHYSIJRSA-N 0.000 claims 1
- ZYZMKDLDCHNQEM-OAHLLOKOSA-N 5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-7-[3-(oxetan-3-yloxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)OC3COC3)=O)=C2O1 ZYZMKDLDCHNQEM-OAHLLOKOSA-N 0.000 claims 1
- AEVIANLNHWLUML-QNSVNVJESA-N 5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-7-[3-(oxolan-3-ylmethoxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)OCC3COCC3)=O)=C2O1 AEVIANLNHWLUML-QNSVNVJESA-N 0.000 claims 1
- XIMCNZHZTMYTKK-TZHYSIJRSA-N 5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-7-[3-(oxolan-3-yloxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)OC3COCC3)=O)=C2O1 XIMCNZHZTMYTKK-TZHYSIJRSA-N 0.000 claims 1
- GPNARNKKVSQDKQ-GOSISDBHSA-N 5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-7-[3-[2-(2-oxopyrrolidin-1-yl)ethoxy]pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)OCCN3C(CCC3)=O)=O)=C2O1 GPNARNKKVSQDKQ-GOSISDBHSA-N 0.000 claims 1
- ZEXMGFHHBCQZFB-IAGOWNOFSA-N 5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-7-[3-[[(2r)-oxetan-2-yl]methoxy]pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)OC[C@@H]3OCC3)=O)=C2O1 ZEXMGFHHBCQZFB-IAGOWNOFSA-N 0.000 claims 1
- ZEXMGFHHBCQZFB-SJORKVTESA-N 5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-7-[3-[[(2s)-oxetan-2-yl]methoxy]pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)OC[C@H]3OCC3)=O)=C2O1 ZEXMGFHHBCQZFB-SJORKVTESA-N 0.000 claims 1
- UGUGLNIFVYATCV-UHFFFAOYSA-N 5-methyl-7-[2-(oxan-4-ylmethoxy)pyridin-4-yl]-2-(1,4-oxazepan-4-ylmethyl)furo[3,2-c]pyridin-4-one Chemical compound C1=2OC(CN3CCOCCC3)=CC=2C(=O)N(C)C=C1C(C=1)=CC=NC=1OCC1CCOCC1 UGUGLNIFVYATCV-UHFFFAOYSA-N 0.000 claims 1
- HVJNEUPSYMMECJ-CYBMUJFWSA-N 7-(2-aminopyridin-4-yl)-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C=C(N)N=CC=3)=O)=C2O1 HVJNEUPSYMMECJ-CYBMUJFWSA-N 0.000 claims 1
- UVHOTKWPYIGJOA-UHFFFAOYSA-N 7-(3,4-dimethoxyphenyl)-5-methyl-2-(morpholin-4-ylmethyl)furo[3,2-c]pyridin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN(C)C(=O)C2=C1OC(CN1CCOCC1)=C2 UVHOTKWPYIGJOA-UHFFFAOYSA-N 0.000 claims 1
- GAJMGOCHIMRYAH-UHFFFAOYSA-N 7-(3,4-dimethoxyphenyl)-5-methyl-2-(piperidin-1-ylmethyl)furo[3,2-c]pyridin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN(C)C(=O)C2=C1OC(CN1CCCCC1)=C2 GAJMGOCHIMRYAH-UHFFFAOYSA-N 0.000 claims 1
- SBTNGPOTCXTYMB-UHFFFAOYSA-N 7-(3,4-dimethoxyphenyl)-5-methyl-2-[(3-methylmorpholin-4-yl)methyl]furo[3,2-c]pyridin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN(C)C(=O)C2=C1OC(CN1C(COCC1)C)=C2 SBTNGPOTCXTYMB-UHFFFAOYSA-N 0.000 claims 1
- SVUMANNVOCNDAY-UHFFFAOYSA-N 7-(3,4-dimethoxyphenyl)-5-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]furo[2,3-d]pyridazin-4-one Chemical compound COC=1C=C(C=CC1OC)C1=NN(C(C2=C1OC(=C2)CN2CCN(CC2)S(=O)(=O)C)=O)C SVUMANNVOCNDAY-UHFFFAOYSA-N 0.000 claims 1
- VPGFVXUZUMEVBI-UHFFFAOYSA-N 7-(3,4-dimethoxyphenyl)-5-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]furo[3,2-c]pyridin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN(C)C(=O)C2=C1OC(CN1CCN(CC1)S(C)(=O)=O)=C2 VPGFVXUZUMEVBI-UHFFFAOYSA-N 0.000 claims 1
- NQSYBFFTCCDUGQ-OAHLLOKOSA-N 7-(3,4-dimethoxyphenyl)-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN(C)C(=O)C2=C1OC(CN1[C@@H](CN(CC1)S(C)(=O)=O)C)=C2 NQSYBFFTCCDUGQ-OAHLLOKOSA-N 0.000 claims 1
- PZYFABOJKXAFSS-CQSZACIVSA-N 7-(3-aminophenyl)-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C=C(N)C=CC=3)=O)=C2O1 PZYFABOJKXAFSS-CQSZACIVSA-N 0.000 claims 1
- WWQFFZOCZFZRSP-OAHLLOKOSA-N 7-(3-cyclopropyloxypyridin-4-yl)-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)OC3CC3)=O)=C2O1 WWQFFZOCZFZRSP-OAHLLOKOSA-N 0.000 claims 1
- YADJSPPQXGQMCB-OAHLLOKOSA-N 7-(3-ethoxypyridin-4-yl)-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound CCOC1=CN=CC=C1C1=CN(C)C(=O)C2=C1OC(CN1[C@@H](CN(CC1)S(C)(=O)=O)C)=C2 YADJSPPQXGQMCB-OAHLLOKOSA-N 0.000 claims 1
- PSNZFFGOHFCPKC-CYBMUJFWSA-N 7-(3-hydroxypyridin-4-yl)-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)O)=O)=C2O1 PSNZFFGOHFCPKC-CYBMUJFWSA-N 0.000 claims 1
- KIWPYLUFZAGLGZ-MRXNPFEDSA-N 7-[2-(2-methoxyethoxy)pyridin-4-yl]-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C1=NC(OCCOC)=CC(C=2C=3OC(CN4[C@@H](CN(CC4)S(C)(=O)=O)C)=CC=3C(=O)N(C)C=2)=C1 KIWPYLUFZAGLGZ-MRXNPFEDSA-N 0.000 claims 1
- QETXRIOCXCNBFV-MRXNPFEDSA-N 7-[2-(cyclopropylmethoxy)pyridin-4-yl]-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C=C(OCC4CC4)N=CC=3)=O)=C2O1 QETXRIOCXCNBFV-MRXNPFEDSA-N 0.000 claims 1
- SJNJBIGYYCYNFE-MRXNPFEDSA-N 7-[2-(cyclopropylmethylamino)pyridin-3-yl]-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=NC=CC=3)NCC3CC3)=O)=C2O1 SJNJBIGYYCYNFE-MRXNPFEDSA-N 0.000 claims 1
- KXDRQTINKBLAEK-TZHYSIJRSA-N 7-[3-(1-methoxypropan-2-yloxy)pyridin-4-yl]-5-methyl-2-[[(2R)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound COCC(C)OC=1C=NC=CC1C=1C2=C(C(N(C1)C)=O)C=C(O2)CN2[C@@H](CN(CC2)S(=O)(=O)C)C KXDRQTINKBLAEK-TZHYSIJRSA-N 0.000 claims 1
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- PEZPDAJVRQMYEJ-OAHLLOKOSA-N 7-[3-(2-hydroxyethoxy)pyridin-4-yl]-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)OCCO)=O)=C2O1 PEZPDAJVRQMYEJ-OAHLLOKOSA-N 0.000 claims 1
- HODLGFLRFMOVJV-MRXNPFEDSA-N 7-[3-(2-methoxyethoxy)pyridin-4-yl]-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound COCCOC1=CN=CC=C1C1=CN(C)C(=O)C2=C1OC(CN1[C@@H](CN(CC1)S(C)(=O)=O)C)=C2 HODLGFLRFMOVJV-MRXNPFEDSA-N 0.000 claims 1
- BJQQEUIUICVSTJ-TZHYSIJRSA-N 7-[3-(2-methoxypropoxy)pyridin-4-yl]-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound COC(C)COC1=CN=CC=C1C1=CN(C)C(=O)C2=C1OC(CN1[C@@H](CN(CC1)S(C)(=O)=O)C)=C2 BJQQEUIUICVSTJ-TZHYSIJRSA-N 0.000 claims 1
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- ZRIWCCGYWSMJPP-UHFFFAOYSA-N 7-[3-(cyclopropylmethylamino)pyridin-4-yl]-5-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]furo[3,2-c]pyridin-4-one Chemical compound C1=2OC(CN3CCN(CC3)S(C)(=O)=O)=CC=2C(=O)N(C)C=C1C1=CC=NC=C1NCC1CC1 ZRIWCCGYWSMJPP-UHFFFAOYSA-N 0.000 claims 1
- DDNKKCFLCRCHDR-MRXNPFEDSA-N 7-[3-(cyclopropylmethylamino)pyridin-4-yl]-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)NCC3CC3)=O)=C2O1 DDNKKCFLCRCHDR-MRXNPFEDSA-N 0.000 claims 1
- NNADKDPXRPINPF-AAFJCEBUSA-N 7-[3-[(2,2-difluorocyclopropyl)methoxy]pyridin-4-yl]-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)OCC3C(C3)(F)F)=O)=C2O1 NNADKDPXRPINPF-AAFJCEBUSA-N 0.000 claims 1
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- FBIMSDPPUYQICZ-UHFFFAOYSA-N n-[4-[2-[[4-(methanesulfonamido)piperidin-1-yl]methyl]-5-methyl-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC(C=2C=3OC(CN4CCC(CC4)NS(C)(=O)=O)=CC=3C(=O)N(C)C=2)=C1 FBIMSDPPUYQICZ-UHFFFAOYSA-N 0.000 claims 1
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- ACAJTXVTNBDQFS-UHFFFAOYSA-N n-[4-[5-methyl-2-[(4-methyl-1,4-diazepan-1-yl)methyl]-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C1CN(C)CCCN1CC1=CC(C(N(C)C=C2C=3C=C(NC(C)=O)N=CC=3)=O)=C2O1 ACAJTXVTNBDQFS-UHFFFAOYSA-N 0.000 claims 1
- RKMXICFSVCXHEP-UHFFFAOYSA-N n-[4-[5-methyl-2-[(4-methyl-3-oxopiperazin-1-yl)methyl]-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C1C(=O)N(C)CCN1CC1=CC(C(N(C)C=C2C=3C=C(NC(C)=O)N=CC=3)=O)=C2O1 RKMXICFSVCXHEP-UHFFFAOYSA-N 0.000 claims 1
- FCKPKEVVECUGED-UHFFFAOYSA-N n-[4-[5-methyl-2-[(4-methylpiperazin-1-yl)methyl]-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C1CN(C)CCN1CC1=CC(C(N(C)C=C2C=3C=C(NC(C)=O)N=CC=3)=O)=C2O1 FCKPKEVVECUGED-UHFFFAOYSA-N 0.000 claims 1
- REVVQHQBCHKAMB-UHFFFAOYSA-N n-[4-[5-methyl-2-[(4-methylsulfonyl-2-oxopiperazin-1-yl)methyl]-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC(C=2C=3OC(CN4C(CN(CC4)S(C)(=O)=O)=O)=CC=3C(=O)N(C)C=2)=C1 REVVQHQBCHKAMB-UHFFFAOYSA-N 0.000 claims 1
- QQTMSFFWDWGMFQ-UHFFFAOYSA-N n-[4-[5-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC(C=2C=3OC(CN4CCN(CC4)S(C)(=O)=O)=CC=3C(=O)N(C)C=2)=C1 QQTMSFFWDWGMFQ-UHFFFAOYSA-N 0.000 claims 1
- YWNGWHICJNAASW-UHFFFAOYSA-N n-[4-[5-methyl-2-[1-(4-methylsulfonylpiperazin-1-yl)ethyl]-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C=1C(C(N(C)C=C2C=3C=C(NC(C)=O)N=CC=3)=O)=C2OC=1C(C)N1CCN(S(C)(=O)=O)CC1 YWNGWHICJNAASW-UHFFFAOYSA-N 0.000 claims 1
- JUWVNUCBAGPWBE-UHFFFAOYSA-N n-[4-[5-methyl-2-[2-(4-methylsulfonylpiperazin-1-yl)propan-2-yl]-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC(C=2C=3OC(=CC=3C(=O)N(C)C=2)C(C)(C)N2CCN(CC2)S(C)(=O)=O)=C1 JUWVNUCBAGPWBE-UHFFFAOYSA-N 0.000 claims 1
- MCTBSAVNHXJNFR-CQSZACIVSA-N n-[4-[5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C=C(NC(C)=O)N=CC=3)=O)=C2O1 MCTBSAVNHXJNFR-CQSZACIVSA-N 0.000 claims 1
- XGAYYTTXMZNIOV-OAHLLOKOSA-N n-[4-[5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]cyclopropanecarboxamide Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C=C(NC(=O)C4CC4)N=CC=3)=O)=C2O1 XGAYYTTXMZNIOV-OAHLLOKOSA-N 0.000 claims 1
- OYIJHPYBIDDJDH-AWEZNQCLSA-N n-[4-[5-methyl-2-[[(3s)-3-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C1CN(S(C)(=O)=O)[C@@H](C)CN1CC1=CC(C(N(C)C=C2C=3C=C(NC(C)=O)N=CC=3)=O)=C2O1 OYIJHPYBIDDJDH-AWEZNQCLSA-N 0.000 claims 1
- LQEKXFBNRMBUIZ-UHFFFAOYSA-N n-[4-[5-methyl-4-oxo-2-(piperazin-1-ylmethyl)furo[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC(C=2C=3OC(CN4CCNCC4)=CC=3C(=O)N(C)C=2)=C1 LQEKXFBNRMBUIZ-UHFFFAOYSA-N 0.000 claims 1
- JZLISRGVTWVVDJ-UHFFFAOYSA-N n-[4-[5-methyl-4-oxo-2-[(3-oxopiperazin-1-yl)methyl]furo[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC(C=2C=3OC(CN4CC(=O)NCC4)=CC=3C(=O)N(C)C=2)=C1 JZLISRGVTWVVDJ-UHFFFAOYSA-N 0.000 claims 1
- ASNAWWMWJGMFDW-CQSZACIVSA-N n-[5-[5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-3-yl]acetamide Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C=C(NC(C)=O)C=NC=3)=O)=C2O1 ASNAWWMWJGMFDW-CQSZACIVSA-N 0.000 claims 1
- NTLJCXXBLSXRBV-CQSZACIVSA-N n-[6-[5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3N=C(NC(C)=O)C=CC=3)=O)=C2O1 NTLJCXXBLSXRBV-CQSZACIVSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
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| US9765039B2 (en) | 2012-11-21 | 2017-09-19 | Zenith Epigenetics Ltd. | Biaryl derivatives as bromodomain inhibitors |
| US9073878B2 (en) | 2012-11-21 | 2015-07-07 | Zenith Epigenetics Corp. | Cyclic amines as bromodomain inhibitors |
| JP2016507496A (ja) | 2012-12-21 | 2016-03-10 | ゼニス・エピジェネティクス・コーポレイションＺｅｎｉｔｈ Ｅｐｉｇｅｎｅｔｉｃｓ Ｃｏｒｐ． | ブロモドメイン阻害剤としての新規複素環式化合物 |
| SG11201506924YA (en) | 2013-03-15 | 2015-09-29 | Incyte Corp | Tricyclic heterocycles as bet protein inhibitors |
| JP6461118B2 (ja) | 2013-06-21 | 2019-01-30 | ゼニス・エピジェネティクス・リミテッドＺｅｎｉｔｈ Ｅｐｉｇｅｎｅｔｉｃｓ Ｌｔｄ． | ブロモドメイン阻害剤としての新規の置換された二環式化合物 |
| SI3010503T1 (sl) | 2013-06-21 | 2020-07-31 | Zenith Epigenetics Ltd. | Novi biciklični inhibitorji bromodomene |
| EP3019502B1 (en) | 2013-07-08 | 2017-05-17 | Incyte Holdings Corporation | Tricyclic heterocycles as bet protein inhibitors |
| JP6542212B2 (ja) | 2013-07-31 | 2019-07-10 | ゼニス・エピジェネティクス・リミテッドＺｅｎｉｔｈ Ｅｐｉｇｅｎｅｔｉｃｓ Ｌｔｄ． | ブロモドメイン阻害剤としての新規キナゾリノン |
| SG10201804471PA (en) | 2013-10-18 | 2018-07-30 | Celgene Quanticel Research Inc | Bromodomain inhibitors |
| WO2015081189A1 (en) | 2013-11-26 | 2015-06-04 | Incyte Corporation | Bicyclic heterocycles as bet protein inhibitors |
| US9399640B2 (en) | 2013-11-26 | 2016-07-26 | Incyte Corporation | Substituted pyrrolo[2,3-c]pyridines and pyrazolo[3,4-c]pyridines as BET protein inhibitors |
| WO2015095492A1 (en) | 2013-12-19 | 2015-06-25 | Incyte Corporation | Tricyclic heterocycles as bet protein inhibitors |
| PL3134403T3 (pl) | 2014-04-23 | 2020-07-13 | Incyte Corporation | 1H-pirolo[2,3-c]pirydyn-7(6H)-ony i pirazolo[3,4-c]pirydyn-7(6H)-ony jako inhibitory białek BET |
| JP6599979B2 (ja) | 2014-09-15 | 2019-10-30 | インサイト・コーポレイション | Ｂｅｔタンパク質阻害剤として用いるための三環式複素環化合物 |
| US10179125B2 (en) | 2014-12-01 | 2019-01-15 | Zenith Epigenetics Ltd. | Substituted pyridines as bromodomain inhibitors |
| US10710992B2 (en) | 2014-12-01 | 2020-07-14 | Zenith Epigenetics Ltd. | Substituted pyridinones as bromodomain inhibitors |
| WO2016092375A1 (en) | 2014-12-11 | 2016-06-16 | Zenith Epigenetics Corp. | Substituted heterocycles as bromodomain inhibitors |
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| WO2017075377A1 (en) | 2015-10-29 | 2017-05-04 | Incyte Corporation | Amorphous solid form of a bet protein inhibitor |
| CN108884083B (zh) * | 2016-04-07 | 2022-02-25 | 葛兰素史克知识产权第二有限公司 | 作为溴结构域抑制剂的苯并[b]呋喃类化合物 |
| EP3445750A4 (en) * | 2016-04-18 | 2019-11-27 | Celgene Quanticel Research, Inc. | THERAPEUTIC COMPOUNDS |
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| CN109641874A (zh) | 2016-05-10 | 2019-04-16 | C4医药公司 | 用于靶蛋白降解的c3-碳连接的戊二酰亚胺降解决定子体 |
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| CN109790143A (zh) | 2016-05-10 | 2019-05-21 | C4医药公司 | 用于靶蛋白降解的胺连接的c3-戊二酰亚胺降解决定子体 |
| WO2017197056A1 (en) * | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | Bromodomain targeting degronimers for target protein degradation |
| CA3028689A1 (en) | 2016-06-20 | 2017-12-28 | Incyte Corporation | Crystalline solid forms of a bet inhibitor |
| CN109641892B (zh) * | 2016-08-16 | 2021-07-02 | 默克专利有限公司 | 用作可逆btk抑制剂的2-氧代-咪唑并吡啶及其用途 |
| WO2018064589A1 (en) | 2016-09-29 | 2018-04-05 | Dana-Farber Cancer Institute, Inc. | Targeted protein degradation using a mutant e3 ubiquitin ligase |
| WO2018094553A1 (zh) * | 2016-11-22 | 2018-05-31 | 上海联影医疗科技有限公司 | 显示方法和装置 |
| WO2018195155A1 (en) * | 2017-04-18 | 2018-10-25 | Celgene Quanticel Research, Inc. | Therapeutic compounds |
| CN110769822A (zh) | 2017-06-20 | 2020-02-07 | C4医药公司 | 用于蛋白降解的n/o-连接的降解决定子和降解决定子体 |
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| GB201716369D0 (en) * | 2017-10-06 | 2017-11-22 | Glaxosmithkline Intellectual Property (No 2) Ltd | Compounds |
| GB201716392D0 (en) * | 2017-10-06 | 2017-11-22 | Glaxosmithkline Intellectual Property (No 2) Ltd | Compounds |
| CN111372585A (zh) | 2017-11-16 | 2020-07-03 | C4医药公司 | 用于靶蛋白降解的降解剂和降解决定子 |
| CN108358793B (zh) * | 2018-02-12 | 2021-03-23 | 三峡大学 | 一种由炔烃合成的仲胺类化合物及其合成方法 |
| EP3773576A4 (en) | 2018-03-26 | 2021-12-29 | C4 Therapeutics, Inc. | Cereblon binders for the degradation of ikaros |
| EP3781156A4 (en) | 2018-04-16 | 2022-05-18 | C4 Therapeutics, Inc. | SPIROCYCLIC COMPOUNDS |
| CN120698983A (zh) | 2018-12-20 | 2025-09-26 | C4医药公司 | 靶向蛋白降解 |
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| CN112625036A (zh) * | 2019-10-08 | 2021-04-09 | 上海海和药物研究开发股份有限公司 | 一类具有brd4抑制活性的化合物、其制备方法及用途 |
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| GB9004781D0 (en) | 1990-03-02 | 1990-04-25 | Glaxo Group Ltd | Device |
| FR2795730B1 (fr) * | 1999-07-01 | 2001-08-31 | Adir | Nouveaux inhibiteurs de metalloproteases, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| EP1217000A1 (en) | 2000-12-23 | 2002-06-26 | Aventis Pharma Deutschland GmbH | Inhibitors of factor Xa and factor VIIa |
| JP2006524672A (ja) | 2003-04-25 | 2006-11-02 | ユニバーシティー・カッレッジ・カーディフ・コンサルタンツ・リミテッド | ウイルス感染の治療において使用するための複素環式化合物 |
| CN1901958B (zh) | 2003-11-03 | 2011-03-09 | 葛兰素集团有限公司 | 流体分配装置 |
| DK2410844T3 (en) | 2009-03-27 | 2016-07-04 | Merck Sharp & Dohme | Inhibitors of hepatitis C virus replication |
| KR20120078703A (ko) | 2009-08-26 | 2012-07-10 | 다케다 야쿠힌 고교 가부시키가이샤 | 융합 헤테로시클릭 고리 유도체 및 이의 용도 |
| US8927718B2 (en) * | 2009-08-26 | 2015-01-06 | Takeda Pharmaceutical Company Limited | Fused heterocyclic ring derivative and use thereof |
| AU2010314395B2 (en) | 2009-11-05 | 2015-04-09 | Glaxosmithkline Llc | Benzodiazepine bromodomain inhibitor |
| GB0919434D0 (en) | 2009-11-05 | 2009-12-23 | Glaxosmithkline Llc | Novel compounds |
| GB0919423D0 (en) | 2009-11-05 | 2009-12-23 | Glaxosmithkline Llc | Novel compounds |
| CN102276616B (zh) | 2011-08-04 | 2013-09-04 | 中国科学院长春应用化学研究所 | 一种呋喃[3,2-c]吡啶-4(5H)-酮类化合物合成方法 |
| WO2013027168A1 (en) * | 2011-08-22 | 2013-02-28 | Pfizer Inc. | Novel heterocyclic compounds as bromodomain inhibitors |
| WO2013097052A1 (en) * | 2011-12-30 | 2013-07-04 | Abbott Laboratories | Bromodomain inhibitors |
| SG10201804471PA (en) * | 2013-10-18 | 2018-07-30 | Celgene Quanticel Research Inc | Bromodomain inhibitors |
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- 2014-03-12 RU RU2015137103A patent/RU2655727C9/ru not_active IP Right Cessation
- 2014-03-12 CA CA2903357A patent/CA2903357A1/en not_active Abandoned
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- 2014-03-12 EP EP14709932.9A patent/EP2970323B1/en active Active
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