JP2015514780A5 - - Google Patents
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- JP2015514780A5 JP2015514780A5 JP2015507204A JP2015507204A JP2015514780A5 JP 2015514780 A5 JP2015514780 A5 JP 2015514780A5 JP 2015507204 A JP2015507204 A JP 2015507204A JP 2015507204 A JP2015507204 A JP 2015507204A JP 2015514780 A5 JP2015514780 A5 JP 2015514780A5
- Authority
- JP
- Japan
- Prior art keywords
- alkylene
- alkyl
- tetrahydro
- aryl
- isoindol
- 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.)
- Pending
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- 125000001072 heteroaryl group Chemical group 0.000 claims 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims 31
- 125000000217 alkyl group Chemical group 0.000 claims 25
- 150000003839 salts Chemical class 0.000 claims 21
- 150000001875 compounds Chemical class 0.000 claims 18
- -1 bromo, hydroxyl Chemical group 0.000 claims 14
- 239000003814 drug Substances 0.000 claims 14
- 125000005843 halogen group Chemical group 0.000 claims 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 14
- 125000001188 haloalkyl group Chemical group 0.000 claims 12
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 208000017169 kidney disease Diseases 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 201000009030 Carcinoma Diseases 0.000 claims 5
- 208000032839 leukemia Diseases 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 206010039491 Sarcoma Diseases 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 3
- 201000008383 nephritis Diseases 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 201000004624 Dermatitis Diseases 0.000 claims 2
- 208000005777 Lupus Nephritis Diseases 0.000 claims 2
- 206010025323 Lymphomas Diseases 0.000 claims 2
- 201000004253 NUT midline carcinoma Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 206010035664 Pneumonia Diseases 0.000 claims 2
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- 206010040047 Sepsis Diseases 0.000 claims 2
- 208000024313 Testicular Neoplasms Diseases 0.000 claims 2
- 208000009956 adenocarcinoma Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 230000003511 endothelial effect Effects 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000002346 iodo group Chemical group I* 0.000 claims 2
- 230000036210 malignancy Effects 0.000 claims 2
- 208000025113 myeloid leukemia Diseases 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 208000000587 small cell lung carcinoma Diseases 0.000 claims 2
- KTKRIGLYOPUJHW-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-3,6,6-trimethyl-5,7-dihydro-2h-isoindol-4-one Chemical compound C1=C2OCOC2=CC(C=2NC(=C3C(=O)CC(C)(C)CC3=2)C)=C1 KTKRIGLYOPUJHW-UHFFFAOYSA-N 0.000 claims 1
- IWSOERZTQGUJBE-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-3-methyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C1=C2OCOC2=CC(C=2NC(=C3C(=O)CCCC3=2)C)=C1 IWSOERZTQGUJBE-UHFFFAOYSA-N 0.000 claims 1
- JZCJXICMFMLUJZ-UHFFFAOYSA-N 1-(1h-benzimidazol-4-yl)-3-methyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=CC2=C1N=CN2 JZCJXICMFMLUJZ-UHFFFAOYSA-N 0.000 claims 1
- YOTIPHWJHFCAHM-UHFFFAOYSA-N 1-(1h-indol-4-yl)-3-methyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=CC2=C1C=CN2 YOTIPHWJHFCAHM-UHFFFAOYSA-N 0.000 claims 1
- PNFXBCAHIYXNCS-UHFFFAOYSA-N 1-(1h-indol-7-yl)-3-methyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=CC2=C1NC=C2 PNFXBCAHIYXNCS-UHFFFAOYSA-N 0.000 claims 1
- XWHDXODHBWZBOT-UHFFFAOYSA-N 1-(2,5-dimethylphenyl)-3,6,6-trimethyl-5,7-dihydro-2h-isoindol-4-one Chemical compound C=12CC(C)(C)CC(=O)C2=C(C)NC=1C1=CC(C)=CC=C1C XWHDXODHBWZBOT-UHFFFAOYSA-N 0.000 claims 1
- IPQGUMYPDJKXTB-UHFFFAOYSA-N 1-(2-aminophenyl)-3-methyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=CC=C1N IPQGUMYPDJKXTB-UHFFFAOYSA-N 0.000 claims 1
- KFQQPTLDTFBRQK-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-methyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=CC=C1Cl KFQQPTLDTFBRQK-UHFFFAOYSA-N 0.000 claims 1
- ATNQVJPFWABKDU-UHFFFAOYSA-N 1-(2-hydroxyphenyl)-3-methyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=CC=C1O ATNQVJPFWABKDU-UHFFFAOYSA-N 0.000 claims 1
- QZOYGSGPQBSZDX-UHFFFAOYSA-N 1-(2-methoxyphenyl)-3-methyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound COC1=CC=CC=C1C1=C(CCCC2=O)C2=C(C)N1 QZOYGSGPQBSZDX-UHFFFAOYSA-N 0.000 claims 1
- ZFIVCUMQHABKGM-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)-3-methyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=C(C)C(C)=C1 ZFIVCUMQHABKGM-UHFFFAOYSA-N 0.000 claims 1
- GSXPSDSZKQUFLI-UHFFFAOYSA-N 1-(3,5-dimethylphenyl)-3-methyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC(C)=CC(C)=C1 GSXPSDSZKQUFLI-UHFFFAOYSA-N 0.000 claims 1
- IATNVYSUJGABAI-UHFFFAOYSA-N 1-(3-methoxyphenyl)-3-methyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound COC1=CC=CC(C2=C3C(C(CCC3)=O)=C(C)N2)=C1 IATNVYSUJGABAI-UHFFFAOYSA-N 0.000 claims 1
- HNBNCLQGZIXKGD-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-methyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=C(Cl)C=C1 HNBNCLQGZIXKGD-UHFFFAOYSA-N 0.000 claims 1
- HRWQXKQANTYRCN-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3-methyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C1=CC(OC)=CC=C1C1=C(CCCC2=O)C2=C(C)N1 HRWQXKQANTYRCN-UHFFFAOYSA-N 0.000 claims 1
- DRAZPLJDOFGOIK-UHFFFAOYSA-N 1-(4-methylsulfonylphenyl)-2,5,6,7-tetrahydroisoindol-4-one Chemical compound CS(=O)(=O)c1ccc(cc1)-c1[nH]cc2c1CCCC2=O DRAZPLJDOFGOIK-UHFFFAOYSA-N 0.000 claims 1
- KYAWXAUITZHJRN-UHFFFAOYSA-N 1-(5-amino-2-phenoxyphenyl)-3,6-dimethyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound N1C(C)=C2C(=O)CC(C)CC2=C1C1=CC(N)=CC=C1OC1=CC=CC=C1 KYAWXAUITZHJRN-UHFFFAOYSA-N 0.000 claims 1
- WEJMCQNBCYFALA-UHFFFAOYSA-N 1-(5-amino-2-phenoxyphenyl)-3-methyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC(N)=CC=C1OC1=CC=CC=C1 WEJMCQNBCYFALA-UHFFFAOYSA-N 0.000 claims 1
- BGSQOSGWZRPTLA-UHFFFAOYSA-N 1-(5-amino-2-phenylsulfanylphenyl)-3-methyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC(N)=CC=C1SC1=CC=CC=C1 BGSQOSGWZRPTLA-UHFFFAOYSA-N 0.000 claims 1
- ONATZLYGADHBJA-UHFFFAOYSA-N 1-[2-(1-benzothiophen-7-ylmethoxy)phenyl]-3-methyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=CC=C1OCC1=CC=CC2=C1SC=C2 ONATZLYGADHBJA-UHFFFAOYSA-N 0.000 claims 1
- YMCHEABHBGZVDX-UHFFFAOYSA-N 1-[2-(2,3,3a,4,5,6,7,7a-octahydro-1H-indazol-5-ylmethoxy)phenyl]-3-methyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound Cc1[nH]c(c2CCCC(=O)c12)-c1ccccc1OCC1CCC2NNCC2C1 YMCHEABHBGZVDX-UHFFFAOYSA-N 0.000 claims 1
- WMYVPEGLLFWXFC-UHFFFAOYSA-N 1-[2-(cyclopentylmethoxy)phenyl]-3-methyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=CC=C1OCC1CCCC1 WMYVPEGLLFWXFC-UHFFFAOYSA-N 0.000 claims 1
- GYIIQSPBAWRRNV-UHFFFAOYSA-N 1-[2-(cyclopropylmethoxy)-5-methylsulfonylphenyl]-3-methyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC(S(C)(=O)=O)=CC=C1OCC1CC1 GYIIQSPBAWRRNV-UHFFFAOYSA-N 0.000 claims 1
- GQOVPCCOVGDBIY-UHFFFAOYSA-N 1-[2-(furan-2-yl)phenyl]-3-methyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=CC=C1C1=CC=CO1 GQOVPCCOVGDBIY-UHFFFAOYSA-N 0.000 claims 1
- DUSZXFWSVYJAOF-UHFFFAOYSA-N 1-[5-amino-2-(2,4-difluorophenoxy)phenyl]-3-methyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC(N)=CC=C1OC1=CC=C(F)C=C1F DUSZXFWSVYJAOF-UHFFFAOYSA-N 0.000 claims 1
- NTXWWEVXMMKHEZ-UHFFFAOYSA-N 2-[[2-(3-methyl-4-oxo-2,5,6,7-tetrahydroisoindol-1-yl)phenyl]methyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC1=CC=CC=C1C1=C(CCCC2=O)C2=C(C)N1 NTXWWEVXMMKHEZ-UHFFFAOYSA-N 0.000 claims 1
- ACVFVWRQUIKXGY-UHFFFAOYSA-N 3,6,6-trimethyl-1-(2-morpholin-4-ylphenyl)-5,7-dihydro-2h-isoindol-4-one Chemical compound C=12CC(C)(C)CC(=O)C2=C(C)NC=1C1=CC=CC=C1N1CCOCC1 ACVFVWRQUIKXGY-UHFFFAOYSA-N 0.000 claims 1
- SHSSQWGTZJDXJE-UHFFFAOYSA-N 3,6,6-trimethyl-1-(2-phenoxyphenyl)-5,7-dihydro-2h-isoindol-4-one Chemical compound C=12CC(C)(C)CC(=O)C2=C(C)NC=1C1=CC=CC=C1OC1=CC=CC=C1 SHSSQWGTZJDXJE-UHFFFAOYSA-N 0.000 claims 1
- KPLWFVHCDJNLEY-UHFFFAOYSA-N 3,6,6-trimethyl-1-(2-phenylmethoxyphenyl)-5,7-dihydro-2h-isoindol-4-one Chemical compound C=12CC(C)(C)CC(=O)C2=C(C)NC=1C1=CC=CC=C1OCC1=CC=CC=C1 KPLWFVHCDJNLEY-UHFFFAOYSA-N 0.000 claims 1
- UNKBHMZQVRQKMT-UHFFFAOYSA-N 3,6,6-trimethyl-1-phenyl-5,7-dihydro-2h-isoindol-4-one Chemical compound C=12CC(C)(C)CC(=O)C2=C(C)NC=1C1=CC=CC=C1 UNKBHMZQVRQKMT-UHFFFAOYSA-N 0.000 claims 1
- CJTIYLJHCHNPMW-UHFFFAOYSA-N 3,6-dimethyl-1-(2-phenoxyphenyl)-2,5,6,7-tetrahydroisoindol-4-one Chemical compound N1C(C)=C2C(=O)CC(C)CC2=C1C1=CC=CC=C1OC1=CC=CC=C1 CJTIYLJHCHNPMW-UHFFFAOYSA-N 0.000 claims 1
- JGAPUDSHJKIBTJ-UHFFFAOYSA-N 3-(3-methyl-4-oxo-2,5,6,7-tetrahydroisoindol-1-yl)-4-phenoxy-n-(1,3-thiazol-2-yl)benzamide Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC(C(=O)NC=2SC=CN=2)=CC=C1OC1=CC=CC=C1 JGAPUDSHJKIBTJ-UHFFFAOYSA-N 0.000 claims 1
- WVDPOAIKYQWDOZ-UHFFFAOYSA-N 3-(3-methyl-4-oxo-2,5,6,7-tetrahydroisoindol-1-yl)-4-phenoxybenzoic acid Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC(C(O)=O)=CC=C1OC1=CC=CC=C1 WVDPOAIKYQWDOZ-UHFFFAOYSA-N 0.000 claims 1
- CTBWYTRBGFAKKX-UHFFFAOYSA-N 3-(3-methyl-4-oxo-2,5,6,7-tetrahydroisoindol-1-yl)-n-(oxolan-2-ylmethyl)-4-phenoxybenzamide Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC(C(=O)NCC2OCCC2)=CC=C1OC1=CC=CC=C1 CTBWYTRBGFAKKX-UHFFFAOYSA-N 0.000 claims 1
- DFNGNBXFVXAOCM-UHFFFAOYSA-N 3-(4-oxo-2,5,6,7-tetrahydroisoindol-1-yl)benzamide Chemical compound NC(=O)c1cccc(c1)-c1[nH]cc2c1CCCC2=O DFNGNBXFVXAOCM-UHFFFAOYSA-N 0.000 claims 1
- WRXGMFLVIUSNDK-UHFFFAOYSA-N 3-[2-(2,4-difluorophenoxy)-5-(dimethylsulfamoylamino)phenyl]-1-methyl-7-oxo-2,4,5,6-tetrahydroisoindole Chemical compound N1C(C)=C(C(CCC2)=O)C2=C1C1=CC(NS(=O)(=O)N(C)C)=CC=C1OC1=CC=C(F)C=C1F WRXGMFLVIUSNDK-UHFFFAOYSA-N 0.000 claims 1
- KLYIVVNLQIHWNI-UHFFFAOYSA-N 3-methyl-1-(2-phenoxyphenyl)-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=CC=C1OC1=CC=CC=C1 KLYIVVNLQIHWNI-UHFFFAOYSA-N 0.000 claims 1
- VNWIMYPGWYDJDP-UHFFFAOYSA-N 3-methyl-1-(2-phenoxyphenyl)-6-propan-2-yl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound N1C(C)=C2C(=O)CC(C(C)C)CC2=C1C1=CC=CC=C1OC1=CC=CC=C1 VNWIMYPGWYDJDP-UHFFFAOYSA-N 0.000 claims 1
- PAOLRTCRMCYGGK-UHFFFAOYSA-N 3-methyl-1-(2-phenylmethoxyphenyl)-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=CC=C1OCC1=CC=CC=C1 PAOLRTCRMCYGGK-UHFFFAOYSA-N 0.000 claims 1
- QAVZHJBPFKNTBV-UHFFFAOYSA-N 3-methyl-1-(3,4,5-trimethoxyphenyl)-2,5,6,7-tetrahydroisoindol-4-one Chemical compound COC1=C(OC)C(OC)=CC(C2=C3C(C(CCC3)=O)=C(C)N2)=C1 QAVZHJBPFKNTBV-UHFFFAOYSA-N 0.000 claims 1
- ZCRMXBAXVISRIW-UHFFFAOYSA-N 3-methyl-1-(3-phenylmethoxyphenyl)-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C(C=1)=CC=CC=1OCC1=CC=CC=C1 ZCRMXBAXVISRIW-UHFFFAOYSA-N 0.000 claims 1
- KYPZUGNTMFFUGV-UHFFFAOYSA-N 3-methyl-1-(4-methylphenyl)-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=C(C)C=C1 KYPZUGNTMFFUGV-UHFFFAOYSA-N 0.000 claims 1
- SRFWHJITEQCFKW-UHFFFAOYSA-N 3-methyl-1-[2-(2-morpholin-4-ylethoxy)phenyl]-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=CC=C1OCCN1CCOCC1 SRFWHJITEQCFKW-UHFFFAOYSA-N 0.000 claims 1
- ZGXNSYXRSQHEEM-UHFFFAOYSA-N 3-methyl-1-[2-(oxan-4-ylmethoxy)phenyl]-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=CC=C1OCC1CCOCC1 ZGXNSYXRSQHEEM-UHFFFAOYSA-N 0.000 claims 1
- ISLIDDIUISDJBK-UHFFFAOYSA-N 3-methyl-1-[2-(oxolan-2-ylmethoxy)phenyl]-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=CC=C1OCC1CCCO1 ISLIDDIUISDJBK-UHFFFAOYSA-N 0.000 claims 1
- FFCIGHPMQLSGQS-UHFFFAOYSA-N 3-methyl-1-[2-(oxolan-3-ylmethoxy)phenyl]-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=CC=C1OCC1CCOC1 FFCIGHPMQLSGQS-UHFFFAOYSA-N 0.000 claims 1
- ISGFWRVRBVLULL-UHFFFAOYSA-N 3-methyl-1-[2-(phenoxymethyl)phenyl]-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=CC=C1COC1=CC=CC=C1 ISGFWRVRBVLULL-UHFFFAOYSA-N 0.000 claims 1
- KNAYLNPPQZHTRM-UHFFFAOYSA-N 3-methyl-1-[2-(pyridin-2-ylmethoxy)phenyl]-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=CC=C1OCC1=CC=CC=N1 KNAYLNPPQZHTRM-UHFFFAOYSA-N 0.000 claims 1
- MRUGCFKSMMOJMA-UHFFFAOYSA-N 3-methyl-1-[2-(pyridin-3-ylmethoxy)phenyl]-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=CC=C1OCC1=CC=CN=C1 MRUGCFKSMMOJMA-UHFFFAOYSA-N 0.000 claims 1
- GVLVEXRNIGZXQG-UHFFFAOYSA-N 3-methyl-1-[2-(quinolin-8-ylmethoxy)phenyl]-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C1=CN=C2C(COC3=CC=CC=C3C=3NC(=C4C(=O)CCCC4=3)C)=CC=CC2=C1 GVLVEXRNIGZXQG-UHFFFAOYSA-N 0.000 claims 1
- JSMVNMJPTVARQR-UHFFFAOYSA-N 3-methyl-1-[2-[(2-methylphenoxy)methyl]phenyl]-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=CC=C1COC1=CC=CC=C1C JSMVNMJPTVARQR-UHFFFAOYSA-N 0.000 claims 1
- XHJYEPAONLSFRZ-UHFFFAOYSA-N 3-methyl-1-[2-[[3-(trifluoromethyl)phenoxy]methyl]phenyl]-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=C1 XHJYEPAONLSFRZ-UHFFFAOYSA-N 0.000 claims 1
- WDQNILVOGXOEAK-UHFFFAOYSA-N 3-methyl-1-naphthalen-1-yl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C1=CC=C2C(C=3NC(=C4C(=O)CCCC4=3)C)=CC=CC2=C1 WDQNILVOGXOEAK-UHFFFAOYSA-N 0.000 claims 1
- YSRFOFRGKIZHIW-UHFFFAOYSA-N 3-methyl-1-phenyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=CC=C1 YSRFOFRGKIZHIW-UHFFFAOYSA-N 0.000 claims 1
- PYDJAYNMHQETSJ-UHFFFAOYSA-N 3-methyl-6-(2-methylpropyl)-1-(2-phenoxyphenyl)-2,5,6,7-tetrahydroisoindol-4-one Chemical compound N1C(C)=C2C(=O)CC(CC(C)C)CC2=C1C1=CC=CC=C1OC1=CC=CC=C1 PYDJAYNMHQETSJ-UHFFFAOYSA-N 0.000 claims 1
- BGLDFYUDXWBVGT-UHFFFAOYSA-N 4-(3-methyl-4-oxo-2,5,6,7-tetrahydroisoindol-1-yl)benzenesulfonamide Chemical compound C=12CCCC(=O)C2=C(C)NC=1C1=CC=C(S(N)(=O)=O)C=C1 BGLDFYUDXWBVGT-UHFFFAOYSA-N 0.000 claims 1
- 208000030507 AIDS Diseases 0.000 claims 1
- 208000007122 AIDS-Associated Nephropathy Diseases 0.000 claims 1
- 206010000830 Acute leukaemia Diseases 0.000 claims 1
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 1
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 1
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
- 208000026872 Addison Disease Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 201000003076 Angiosarcoma Diseases 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- 206010003571 Astrocytoma Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 1
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 1
- 206010004146 Basal cell carcinoma Diseases 0.000 claims 1
- 208000009137 Behcet syndrome Diseases 0.000 claims 1
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 1
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 206010008583 Chloroma Diseases 0.000 claims 1
- 206010008609 Cholangitis sclerosing Diseases 0.000 claims 1
- 208000005243 Chondrosarcoma Diseases 0.000 claims 1
- 201000009047 Chordoma Diseases 0.000 claims 1
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| EP2970312B1 (en) | 2013-03-11 | 2017-11-15 | The Regents of The University of Michigan | Bet bromodomain inhibitors and therapeutic methods using the same |
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| MX365864B (es) | 2013-06-21 | 2019-06-18 | Zenith Epigenetics Ltd | Inhibidores de bromodominio biciclicos novedosos. |
| CA2915622C (en) | 2013-06-21 | 2020-08-18 | Zenith Epigenetics Corp. | Novel substituted bicyclic compounds as bromodomain inhibitors |
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| EA201690087A1 (ru) | 2013-07-31 | 2016-08-31 | Зенит Эпидженетикс Корп. | Новые квиназолиноны как ингибиторы бромодомена |
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| AU2015222887B2 (en) | 2014-02-28 | 2019-06-27 | The Regents Of The University Of Michigan | 9H-pyrimido[4,5-b]indoles and related analogs as BET bromodomain inhibitors |
| WO2015164480A1 (en) | 2014-04-23 | 2015-10-29 | Incyte Corporation | 1H-PYRROLO[2,3-c]PYRIDIN-7(6H)-ONES AND PYRAZOLO[3,4-c]PYRIDIN-7(6H)-ONES AS INHIBITORS OF BET PROTEINS |
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| US10179125B2 (en) | 2014-12-01 | 2019-01-15 | Zenith Epigenetics Ltd. | Substituted pyridines as bromodomain inhibitors |
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2012
- 2012-04-20 CN CN201280073829.3A patent/CN104334526A/zh active Pending
- 2012-04-20 MX MX2014012635A patent/MX2014012635A/es unknown
- 2012-04-20 WO PCT/CN2012/074411 patent/WO2013155695A1/en not_active Ceased
- 2012-04-20 JP JP2015506064A patent/JP5989229B2/ja not_active Expired - Fee Related
- 2012-04-20 HK HK15107457.4A patent/HK1206744A1/xx unknown
- 2012-04-20 EP EP12874480.2A patent/EP2838881B1/en not_active Not-in-force
- 2012-04-20 CA CA 2870931 patent/CA2870931A1/en not_active Abandoned
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2013
- 2013-03-12 US US13/796,731 patent/US9776990B2/en not_active Expired - Fee Related
- 2013-04-19 WO PCT/US2013/037297 patent/WO2013158952A1/en not_active Ceased
- 2013-04-19 US US14/395,628 patent/US20150111890A1/en not_active Abandoned
- 2013-04-19 EP EP13719348.8A patent/EP2850071A1/en not_active Withdrawn
- 2013-04-19 MX MX2014012695A patent/MX2014012695A/es unknown
- 2013-04-19 CA CA 2870446 patent/CA2870446A1/en not_active Abandoned
- 2013-04-19 JP JP2015507204A patent/JP2015514780A/ja active Pending