HRP20200341T1 - Bromodomenski (bet) inhibitori - Google Patents
Bromodomenski (bet) inhibitori Download PDFInfo
- Publication number
- HRP20200341T1 HRP20200341T1 HRP20200341TT HRP20200341T HRP20200341T1 HR P20200341 T1 HRP20200341 T1 HR P20200341T1 HR P20200341T T HRP20200341T T HR P20200341TT HR P20200341 T HRP20200341 T HR P20200341T HR P20200341 T1 HRP20200341 T1 HR P20200341T1
- Authority
- HR
- Croatia
- Prior art keywords
- methylisoquinolin
- methylsulfonylphenyl
- alkyl
- hydrogen
- pharmaceutically acceptable
- Prior art date
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- 102000001805 Bromodomains Human genes 0.000 title 1
- 108050009021 Bromodomains Proteins 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 19
- 229910052739 hydrogen Inorganic materials 0.000 claims 19
- 239000001257 hydrogen Substances 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 17
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 15
- 125000003118 aryl group Chemical group 0.000 claims 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims 14
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical group 0.000 claims 14
- 125000000623 heterocyclic group Chemical group 0.000 claims 13
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 12
- 150000002431 hydrogen Chemical group 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- BIBKQXXWGSXVCX-UHFFFAOYSA-N 4-[2-(2,4-difluorophenoxy)-5-methylsulfonylphenyl]-2-methylisoquinolin-1-one Chemical compound Cn1cc(-c2cc(ccc2Oc2ccc(F)cc2F)S(C)(=O)=O)c2ccccc2c1=O BIBKQXXWGSXVCX-UHFFFAOYSA-N 0.000 claims 2
- WERZRMYQMCOATQ-UHFFFAOYSA-N 4-[2-(4-aminocyclohexyl)oxy-5-methylsulfonylphenyl]-2-methylisoquinolin-1-one Chemical compound Cn1cc(-c2cc(ccc2OC2CCC(N)CC2)S(C)(=O)=O)c2ccccc2c1=O WERZRMYQMCOATQ-UHFFFAOYSA-N 0.000 claims 2
- VIPASDXCXKWHNQ-UHFFFAOYSA-N 4-[2-(cyclopropylmethoxy)-5-ethylsulfonylphenyl]-2-methylisoquinolin-1-one Chemical compound CCS(=O)(=O)c1ccc(OCC2CC2)c(c1)-c1cn(C)c(=O)c2ccccc12 VIPASDXCXKWHNQ-UHFFFAOYSA-N 0.000 claims 2
- UWZAJPITKGWMFJ-UHFFFAOYSA-N 4-[2-(cyclopropylmethoxy)-5-methylsulfonylphenyl]-2-methylisoquinolin-1-one Chemical compound Cn1cc(-c2cc(ccc2OCC2CC2)S(C)(=O)=O)c2ccccc2c1=O UWZAJPITKGWMFJ-UHFFFAOYSA-N 0.000 claims 2
- YZOPGLSDJSTSFD-UHFFFAOYSA-N 4-[2-(cyclopropylmethoxy)-5-methylsulfonylphenyl]-6-fluoro-2-methylisoquinolin-1-one Chemical compound Cn1cc(-c2cc(ccc2OCC2CC2)S(C)(=O)=O)c2cc(F)ccc2c1=O YZOPGLSDJSTSFD-UHFFFAOYSA-N 0.000 claims 2
- SAHBYBMZDQHFBT-UHFFFAOYSA-N 4-[2-(cyclopropylmethoxy)-5-methylsulfonylphenyl]-7-fluoro-2-methylisoquinolin-1-one Chemical compound Cn1cc(-c2cc(ccc2OCC2CC2)S(C)(=O)=O)c2ccc(F)cc2c1=O SAHBYBMZDQHFBT-UHFFFAOYSA-N 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- NHZGVIKTCUYUSB-UHFFFAOYSA-N 2-methyl-4-(5-methylsulfonyl-2-propoxyphenyl)isoquinolin-1-one Chemical compound CCCOc1ccc(cc1-c1cn(C)c(=O)c2ccccc12)S(C)(=O)=O NHZGVIKTCUYUSB-UHFFFAOYSA-N 0.000 claims 1
- MAZPOVPRTCRJER-UHFFFAOYSA-N 2-methyl-4-(5-methylsulfonyl-2-propylphenyl)isoquinolin-1-one Chemical compound CCCc1ccc(cc1-c1cn(C)c(=O)c2ccccc12)S(C)(=O)=O MAZPOVPRTCRJER-UHFFFAOYSA-N 0.000 claims 1
- INXNDKZZPZLIDT-UHFFFAOYSA-N 2-methyl-4-[5-(methylsulfonylmethyl)-2-(2,2,2-trifluoroethoxy)phenyl]isoquinolin-1-one Chemical compound Cn1cc(-c2cc(CS(C)(=O)=O)ccc2OCC(F)(F)F)c2ccccc2c1=O INXNDKZZPZLIDT-UHFFFAOYSA-N 0.000 claims 1
- IMLQTINKTRHTSF-UHFFFAOYSA-N 2-methyl-4-[5-methylsulfonyl-2-(oxan-3-yloxy)phenyl]isoquinolin-1-one Chemical compound Cn1cc(-c2cc(ccc2OC2CCCOC2)S(C)(=O)=O)c2ccccc2c1=O IMLQTINKTRHTSF-UHFFFAOYSA-N 0.000 claims 1
- LCOUXAUKQIPINJ-UHFFFAOYSA-N 2-methyl-4-[5-methylsulfonyl-2-(oxan-4-ylamino)phenyl]isoquinolin-1-one Chemical compound Cn1cc(-c2cc(ccc2NC2CCOCC2)S(C)(=O)=O)c2ccccc2c1=O LCOUXAUKQIPINJ-UHFFFAOYSA-N 0.000 claims 1
- UVICTECUAZWRBM-UHFFFAOYSA-N 2-methyl-4-[5-methylsulfonyl-2-(oxan-4-yloxy)phenyl]isoquinolin-1-one Chemical compound Cn1cc(-c2cc(ccc2OC2CCOCC2)S(C)(=O)=O)c2ccccc2c1=O UVICTECUAZWRBM-UHFFFAOYSA-N 0.000 claims 1
- SBHWUTKUDWGWRZ-UHFFFAOYSA-N 2-methyl-4-[5-methylsulfonyl-2-(oxolan-3-ylamino)phenyl]isoquinolin-1-one Chemical compound Cn1cc(-c2cc(ccc2NC2CCOC2)S(C)(=O)=O)c2ccccc2c1=O SBHWUTKUDWGWRZ-UHFFFAOYSA-N 0.000 claims 1
- WHLMQCSMDPUERJ-UHFFFAOYSA-N 2-methyl-4-[5-methylsulfonyl-2-(oxolan-3-yloxy)phenyl]isoquinolin-1-one Chemical compound Cn1cc(-c2cc(ccc2OC2CCOC2)S(C)(=O)=O)c2ccccc2c1=O WHLMQCSMDPUERJ-UHFFFAOYSA-N 0.000 claims 1
- NLTGVCQAQLMSKM-UHFFFAOYSA-N 4-(2-but-2-ynoxy-5-ethylsulfonylphenyl)-2-methylisoquinolin-1-one Chemical compound CCS(=O)(=O)c1ccc(OCC#CC)c(c1)-c1cn(C)c(=O)c2ccccc12 NLTGVCQAQLMSKM-UHFFFAOYSA-N 0.000 claims 1
- IDLCHRKCJBAIIS-UHFFFAOYSA-N 4-(2-but-2-ynoxy-5-methylsulfonylphenyl)-2-methylisoquinolin-1-one Chemical compound CC#CCOc1ccc(cc1-c1cn(C)c(=O)c2ccccc12)S(C)(=O)=O IDLCHRKCJBAIIS-UHFFFAOYSA-N 0.000 claims 1
- NBKHPLWGRRYKTG-UHFFFAOYSA-N 4-(2-butyl-5-methylsulfonylphenyl)-2-methylisoquinolin-1-one Chemical compound CCCCc1ccc(cc1-c1cn(C)c(=O)c2ccccc12)S(C)(=O)=O NBKHPLWGRRYKTG-UHFFFAOYSA-N 0.000 claims 1
- HCCWYWKLKVGHFT-UHFFFAOYSA-N 4-(2-ethoxy-5-methylsulfonylphenyl)-2-methylisoquinolin-1-one Chemical compound CCOc1ccc(cc1-c1cn(C)c(=O)c2ccccc12)S(C)(=O)=O HCCWYWKLKVGHFT-UHFFFAOYSA-N 0.000 claims 1
- HJTZDNRUVYTTFW-UHFFFAOYSA-N 4-(2-ethyl-5-methylsulfonylphenyl)-2-methylisoquinolin-1-one Chemical compound CCc1ccc(cc1-c1cn(C)c(=O)c2ccccc12)S(C)(=O)=O HJTZDNRUVYTTFW-UHFFFAOYSA-N 0.000 claims 1
- NPTDHSPXINASFY-UHFFFAOYSA-N 4-[2-(2-cyclopropylethyl)-5-methylsulfonylphenyl]-2-methylisoquinolin-1-one Chemical compound Cn1cc(-c2cc(ccc2CCC2CC2)S(C)(=O)=O)c2ccccc2c1=O NPTDHSPXINASFY-UHFFFAOYSA-N 0.000 claims 1
- JBNZNDKUKGSZAK-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)oxy-5-methylsulfonylphenyl]-2-methylisoquinolin-1-one Chemical compound Cn1cc(-c2cc(ccc2OC2CCC(O)CC2)S(C)(=O)=O)c2ccccc2c1=O JBNZNDKUKGSZAK-UHFFFAOYSA-N 0.000 claims 1
- JKAZCBBXOKWWEH-UHFFFAOYSA-N 4-[2-(cyclopropylmethoxy)-5-ethylsulfonylphenyl]-6-fluoro-2-methylisoquinolin-1-one Chemical compound CCS(=O)(=O)c1ccc(OCC2CC2)c(c1)-c1cn(C)c(=O)c2ccc(F)cc12 JKAZCBBXOKWWEH-UHFFFAOYSA-N 0.000 claims 1
- FVZMZBYEWQNJTG-UHFFFAOYSA-N 4-[2-(cyclopropylmethoxy)-5-methylsulfonylphenyl]-2-methyl-6-(trifluoromethyl)isoquinolin-1-one Chemical compound Cn1cc(-c2cc(ccc2OCC2CC2)S(C)(=O)=O)c2cc(ccc2c1=O)C(F)(F)F FVZMZBYEWQNJTG-UHFFFAOYSA-N 0.000 claims 1
- XEKCYOIHCBZJCW-UHFFFAOYSA-N 4-[2-(cyclopropylmethoxy)-5-methylsulfonylphenyl]-6-methoxy-2-methylisoquinolin-1-one Chemical compound COc1ccc2c(c1)c(cn(C)c2=O)-c1cc(ccc1OCC1CC1)S(C)(=O)=O XEKCYOIHCBZJCW-UHFFFAOYSA-N 0.000 claims 1
- VZNDCJGNWDMXTH-UHFFFAOYSA-N 4-[2-(cyclopropylmethoxy)-5-propan-2-ylsulfonylphenyl]-2-methylisoquinolin-1-one Chemical compound CC(C)S(=O)(=O)c1ccc(OCC2CC2)c(c1)-c1cn(C)c(=O)c2ccccc12 VZNDCJGNWDMXTH-UHFFFAOYSA-N 0.000 claims 1
- ZQFBIHHSESXZCD-UHFFFAOYSA-N 4-[2-(cyclopropylmethoxy)-5-propan-2-ylsulfonylphenyl]-6-methoxy-2-methylisoquinolin-1-one Chemical compound COc1ccc2c(c1)c(cn(C)c2=O)-c1cc(ccc1OCC1CC1)S(=O)(=O)C(C)C ZQFBIHHSESXZCD-UHFFFAOYSA-N 0.000 claims 1
- ZRXSHUIWXRFENX-UHFFFAOYSA-N 4-[2-(cyclopropylmethylamino)-5-ethylsulfonylphenyl]-2-methylisoquinolin-1-one Chemical compound CCS(=O)(=O)c1ccc(NCC2CC2)c(c1)-c1cn(C)c(=O)c2ccccc12 ZRXSHUIWXRFENX-UHFFFAOYSA-N 0.000 claims 1
- HRKMXMKJFSTWOC-UHFFFAOYSA-N 4-[2-(cyclopropylmethylamino)-5-ethylsulfonylphenyl]-7-fluoro-2-methylisoquinolin-1-one Chemical compound CCS(=O)(=O)c1ccc(NCC2CC2)c(c1)-c1cn(C)c(=O)c2cc(F)ccc12 HRKMXMKJFSTWOC-UHFFFAOYSA-N 0.000 claims 1
- IZGWLFIQKXUUDY-UHFFFAOYSA-N 4-[2-(cyclopropylmethylamino)-5-methylsulfonylphenyl]-2-methylisoquinolin-1-one Chemical compound Cn1cc(-c2cc(ccc2NCC2CC2)S(C)(=O)=O)c2ccccc2c1=O IZGWLFIQKXUUDY-UHFFFAOYSA-N 0.000 claims 1
- VZZGFPYGXOOQHB-UHFFFAOYSA-N 4-[2-(cyclopropylmethylamino)-5-methylsulfonylphenyl]-7-fluoro-2-methylisoquinolin-1-one Chemical compound Cn1cc(-c2cc(ccc2NCC2CC2)S(C)(=O)=O)c2ccc(F)cc2c1=O VZZGFPYGXOOQHB-UHFFFAOYSA-N 0.000 claims 1
- AIKNMWUWNIWCCY-UHFFFAOYSA-N 4-[2-[(4-hydroxycyclohexyl)amino]-5-methylsulfonylphenyl]-2-methylisoquinolin-1-one Chemical compound Cn1cc(-c2cc(ccc2NC2CCC(O)CC2)S(C)(=O)=O)c2ccccc2c1=O AIKNMWUWNIWCCY-UHFFFAOYSA-N 0.000 claims 1
- CQOLECCTLXEOIC-UHFFFAOYSA-N 4-[5-(ethylsulfonylmethyl)-2-(2,2,2-trifluoroethoxy)phenyl]-2-methylisoquinolin-1-one Chemical compound CCS(=O)(=O)Cc1ccc(OCC(F)(F)F)c(c1)-c1cn(C)c(=O)c2ccccc12 CQOLECCTLXEOIC-UHFFFAOYSA-N 0.000 claims 1
- ZCIJDOBKOPLQDK-UHFFFAOYSA-N 4-[5-ethylsulfonyl-2-(4-hydroxycyclohexyl)oxyphenyl]-2-methylisoquinolin-1-one Chemical compound CCS(=O)(=O)c1ccc(OC2CCC(O)CC2)c(c1)-c1cn(C)c(=O)c2ccccc12 ZCIJDOBKOPLQDK-UHFFFAOYSA-N 0.000 claims 1
- FGXFOHHRANPSDF-UHFFFAOYSA-N 4-[5-ethylsulfonyl-2-(4-hydroxycyclohexyl)oxyphenyl]-6-fluoro-2-methylisoquinolin-1-one Chemical compound CCS(=O)(=O)c1ccc(OC2CCC(O)CC2)c(c1)-c1cn(C)c(=O)c2ccc(F)cc12 FGXFOHHRANPSDF-UHFFFAOYSA-N 0.000 claims 1
- KUQQNXCPTAGBCT-UHFFFAOYSA-N 4-[5-ethylsulfonyl-2-(4-hydroxycyclohexyl)oxyphenyl]-7-fluoro-2-methylisoquinolin-1-one Chemical compound CCS(=O)(=O)c1ccc(OC2CCC(O)CC2)c(c1)-c1cn(C)c(=O)c2cc(F)ccc12 KUQQNXCPTAGBCT-UHFFFAOYSA-N 0.000 claims 1
- LIUACDNICWVNCA-UHFFFAOYSA-N 6-fluoro-4-[2-(4-hydroxycyclohexyl)oxy-5-methylsulfonylphenyl]-2-methylisoquinolin-1-one Chemical compound Cn1cc(-c2cc(ccc2OC2CCC(O)CC2)S(C)(=O)=O)c2cc(F)ccc2c1=O LIUACDNICWVNCA-UHFFFAOYSA-N 0.000 claims 1
- XGZPZRNPDSWUBR-UHFFFAOYSA-N 7-fluoro-4-[2-(4-hydroxycyclohexyl)oxy-5-methylsulfonylphenyl]-2-methylisoquinolin-1-one Chemical compound Cn1cc(-c2cc(ccc2OC2CCC(O)CC2)S(C)(=O)=O)c2ccc(F)cc2c1=O XGZPZRNPDSWUBR-UHFFFAOYSA-N 0.000 claims 1
- DPXIJYRZFACPMV-UHFFFAOYSA-N N-[2-(2-methyl-1-oxoisoquinolin-4-yl)-4-methylsulfonylphenyl]acetamide Chemical compound CC(=O)Nc1ccc(cc1-c1cn(C)c(=O)c2ccccc12)S(C)(=O)=O DPXIJYRZFACPMV-UHFFFAOYSA-N 0.000 claims 1
- HJHXEBFFCPOBNP-UHFFFAOYSA-N N-[2-(2-methyl-1-oxoisoquinolin-4-yl)-4-methylsulfonylphenyl]cyclopropanecarboxamide Chemical compound Cn1cc(-c2cc(ccc2NC(=O)C2CC2)S(C)(=O)=O)c2ccccc2c1=O HJHXEBFFCPOBNP-UHFFFAOYSA-N 0.000 claims 1
- LJRQCCWVBVFMBE-UHFFFAOYSA-N N-[2-(2-methyl-1-oxoisoquinolin-4-yl)-4-methylsulfonylphenyl]propanamide Chemical compound CCC(=O)Nc1ccc(cc1-c1cn(C)c(=O)c2ccccc12)S(C)(=O)=O LJRQCCWVBVFMBE-UHFFFAOYSA-N 0.000 claims 1
- ZGAFZOGKXSSCEU-UHFFFAOYSA-N N-[4-(2,4-difluorophenoxy)-3-(2-methyl-1-oxoisoquinolin-4-yl)phenyl]ethanesulfonamide Chemical compound CCS(=O)(=O)Nc1ccc(Oc2ccc(F)cc2F)c(c1)-c1cn(C)c(=O)c2ccccc12 ZGAFZOGKXSSCEU-UHFFFAOYSA-N 0.000 claims 1
- RYGKANGIHXJREX-UHFFFAOYSA-N N-[4-methyl-3-(2-methyl-1-oxoisoquinolin-4-yl)phenyl]methanesulfonamide Chemical compound Cc1ccc(NS(C)(=O)=O)cc1-c1cn(C)c(=O)c2ccccc12 RYGKANGIHXJREX-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- HLRKRSZFFZPUDT-UHFFFAOYSA-N [4-(cyclopropylmethoxy)-3-(2-methyl-1-oxoisoquinolin-4-yl)phenyl] sulfamate Chemical compound Cn1cc(-c2cc(OS(N)(=O)=O)ccc2OCC2CC2)c2ccccc2c1=O HLRKRSZFFZPUDT-UHFFFAOYSA-N 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000035897 transcription Effects 0.000 claims 1
- 238000013518 transcription Methods 0.000 claims 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/94—Oxygen atom, e.g. piperidine N-oxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/69—Two or more oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
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- C—CHEMISTRY; METALLURGY
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Claims (17)
1. Spoj Formule (I) ili njegova farmaceutski prihvatljiva sol,
[image]
naznačen time, da
R2 je odabran od CH3, CH2CH3, CH2CF3, CH2F, CHF2, CF3, CH2D, CHD2 ili CD3;
X5 je C-R5 ili N;
X6 je C-R6 ili N;
X7 je C-R7 ili N;
X8 je C-R8 ili N; gdje ne manje od dva od X5, X6, X7 ili X8 može biti N;
R5 je vodik, halogen, -CN, -OR61, -NHR61, -N(R61)2, alkil, cikloalkil, cikloalkilalkil, aril, aralkil, heterociklil, heterociklilalkil, heteroaryl ili heteroarilalkil, gdje je svaki R61 neovisno odabran od alkila, cikloalkila, cikloalkilalkila, arila, aralkila, heterociklila, heterociklilalkila, heteroarila ili heteroarilalkila;
R6 je vodik, halogen, -CN, -OR61, -NHR61, -N(R61)2, alkil, cikloalkil, cikloalkilalkil, aril, aralkil, heterociklil, heterociklilalkil, heteroaril ili heteroarilalkil, gdje je svaki R61 neovisno odabran od alkila, cikloalkila, cikloalkilalkila, arila, aralkila, heterociklila, heterociklilalkila, heteroarila ili heteroarilalkila;
R7 je vodik, halogen, -CN, -OR61, -NHR61, -N(R61)2, alkil, cikloalkil, cikloalkilalkil, aril, aralkil, heterociklil, heterociklilalkil, heteroaril ili heteroarilalkil, gdje je svaki R61 neovisno odabran od alkila, cikloalkila, cikloalkilalkila, arila, aralkila, heterociklila, heterociklilalkila, heteroarila ili heteroarilalkila;
R8 je vodik, halogen ili alkil;
RA je
[image]
X2 je N ili C-R12, gdje je R12 vodik, halogen, alkil ili alkoksi;
R13 je -Y-Z;
Y je odabran od veze, -CH2- ili -CH(C1-C4 alkil)- ;
Z je odabran od -SO2R21, -N(R22)SO2R21, -SO2N(R22)2, -N(R22)SO2N(R22)2,-CON(R22)2, -N(R22)CO2R21, -N(R22)CON(R22)2, -N(R22)COR21, -COR21, -OC(O)N(R22)2, -OSO2N(R22)2 ili -N(R22)SO3R21;
X3 je N ili C-R14, gdje je R14 vodik, halogen, -CN, alkil, cikloalkil ili alkoksi;
X4 je N ili C-R15, gdje je R15 vodik, halogen, alkil, -CN ili alkoksi;
R16 je vodik, halogen, -N(H)COX ili -W-X, gdje je W veza, -O-, -S- ili -NH-, a X je odabran od alkila, arila, aralkila, cikloalkila, cikloalkilalkila, alkinila, cikloalkilalkinila, heterociklila, heterociklilalkila, heteroarila ili heteroarilalkila;
svaki R21 je neovisno odabran od alkila, cikloalkila, cikloalkilalkila, arila, aralkila, heterociklila, heterociklilalkila, heteroarila ili heteroarilalkila; i
svaki R22 je neovisno odabran od vodika, alkila, cikloalkila, cikloalkilalkila, arila, aralkila, heterociklila, heterociklilalkila, heteroarila ili heteroarilalkila.
2. Spoj ili njegova farmaceutski prihvatljiva sol u skladu s patentnim zahtjevom 1, naznačen time, da ima strukturu Formule (Ib),
[image]
naznačen time, da
R2 je odabran od CH3;
X5 je C-H;
X6 je C-R6;
X7 je C-R7;
X8 je C-H;
R6 je vodik ili halogen;
R7 je vodik ili halogen;
RA je
[image]
X2 je C-H;
R13 je -Y-Z;
Y je odabran od veze ili -CH2-;
Z je odabran od -SO2R21, -N(R22)SO2R21, -SO2N(R22)2, -N(R22)SO2N(R22)2, -CON(R22)2, -N(R22)CO2R21, -N(R22)CON(R22)2, -N(R22)COR21, -OC(O)N(R22)2, -OSO2N(R22)2 ili -N(R22)SO3R21;
X3 je C-R14, gdje je R14 vodik, halogen, C1-C3 alkil ili C1-C3 alkoksi;
X4 je C-R15, gdje je R15 vodik ili halogen;
R16 je -W-X, gdje je W veza, -O-, -S- ili -NH-, a X je odabran od alkila, arila, aralkila, cikloalkila, cikloalkilalkila, heterociklila, heterociklilalkila, heteroarila ili heteroarilalkila;
svaki R21 je neovisno odabran od alkila, cikloalkila, cikloalkilalkila, arila, aralkila, heterociklila, heterociklilalkila, heteroarila ili heteroarilalkila; i
svaki R22 je neovisno odabran od vodika, alkila, cikloalkila, cikloalkilalkila, arila, aralkila, heterociklila, heterociklilalkila, heteroarila ili heteroarilalkila.
3. Spoj ili njegova farmaceutski prihvatljiva sol u skladu s patentnim zahtjevom 2, naznačen time, da je R6 halogen a R7 je vodik ili kada je R6 vodik a R7 je halogen ili kada je R6 vodik i R7 je vodik.
4. Spoj ili njegova farmaceutski prihvatljiva sol u skladu s patentnim zahtjevom 2, naznačen time, da je Y veza.
5. Spoj ili njegova farmaceutski prihvatljiva sol u skladu s patentnim zahtjevom 4, naznačen time, da Z je -N(R22)SO2R21 ili -N(R22)SO2N(R22)2.
6. Spoj ili njegova farmaceutski prihvatljiva sol u skladu s patentnim zahtjevom 4, naznačen time, da Z je -SO2R21.
7. Spoj ili njegova farmaceutski prihvatljiva sol u skladu s patentnim zahtjevom 6, naznačen time, da je R21 heterociklil ili heterociklilalkil.
8. Spoj ili njegova farmaceutski prihvatljiva sol u skladu s patentnim zahtjevom 5, naznačen time, da je R22 vodik ili metil.
9. Spoj ili njegova farmaceutski prihvatljiva sol u skladu s patentnim zahtjevom 6, naznačen time, da je R21 alkil, C1-C4 alkil, cikloalkil ili cikloalkilalkil.
10. Spoj ili njegova farmaceutski prihvatljiva sol u skladu s patentnim zahtjevom 2, naznačen time, da W je veza, kada je W -O- ili kada W je -NH-.
11. Spoj ili njegova farmaceutski prihvatljiva sol u skladu s patentnim zahtjevom 10, naznačen time, da X je alkil, X je cikloalkilalkil ili X je aril.
12. Spoj ili njegova farmaceutski prihvatljiva sol u skladu s patentnim zahtjevom 9, naznačen time, da C1-C4 alkil je C1 alkil.
13. Spoj ili njegova farmaceutski prihvatljiva sol u skladu s patentnim zahtjevom 2, naznačen time, da je Y veza, Z je -SO2R21, W je -O-, a X je aril ili cikloalkilalkil.
14. Spoj ili njegova farmaceutski prihvatljiva sol, naznačen time, da je odabran od:
N-[4-metil-3-(2-metil-1-oksoizokinolin-4-il)fenil]metansulfonamida;
4-[2-(ciklopropilmetoksi)-5-metilsulfonilfenil]-2-metilizokinolin-1-ona;
4-[2-(ciklopropilmetoksi)-5-metilsulfonilfenil]-6-fluoro-2-metilizokinolin-1-ona;
4-[2-(ciklopropilmetoksi)-5-metilsulfonilfenil]-7-fluoro-2-metilizokinolin-1-ona;
4-[2-(2,4-difluorofenoksi)-5-metilsulfonilfenil]-2-metilizokinolin-1-ona;
N-[4-(2,4-difluorofenoksi)-3-(2-metil-1-oksoizokinolin-4-il)fenil]etansulfonamida;
4-[2-(ciklopropilmetoksi)-5-etilsulfonilfenil]-2-metilizokinolin-1-ona;
4-[2-(ciklopropilmetoksi)-5-etilsulfonilfenil]-6-fluoro-2-metilizokinolin-1-ona;
2-metil-4-[5-metilsulfonil-2-(oksolan-3-iloksi)fenil]izokinolin-1-ona;
2-metil-4-[5-metilsulfonil-2-(oksan-4-iloksi)fenil]izokinolin-1-ona;
4-(2-etoksi-5-metilsulfonilfenil)-2-metilizokinolin-1-ona;
2-metil-4-(5-metilsulfonil-2-propoksifenil)izokinolin-1-ona;
2-metil-4-[5-metilsulfonil-2-(oksan-3-iloksi)fenil]izokinolin-1-ona;
4-[2-(trans-4-hidroksicikloheksil)oksi-5-metilsulfonilfenil]-2-metilizokinolin-1-ona;
4-[5-etilsulfonil-2-(trans-4-hidroksicikloheksil)oksifenil]-2-metilizokinolin-1-ona;
4-[2-(trans-4-aminocikloheksil)oksi-5-metilsulfonilfenil]-2-metilizokinolin-1-ona;
4-[2-(cis-4-aminocikloheksil)oksi-5-metilsulfonilfenil]-2-metilizokinolin-1-ona;
4-(2-but-2-inoksi-5-metilsulfonilfenil)-2-metilizokinolin-1-ona;
4-(2-but-2-inoksi-5-etilsulfonilfenil)-2-metilizokinolin-1-ona;
6-fluoro-4-[2-(trans-4-hidroksicikloheksil)oksi-5-metilsulfonilfenil]-2-metilizokinolin-1-ona;
7-fluoro-4-[2-(trans-4-hidroksicikloheksil)oksi-5-metilsulfonilfenil]-2-metilizokinolin-1-ona;
4-[5-etilsulfonil-2-(trans-4-hidroksicikloheksil)oksifenil]-6-fluoro-2-metilizokinolin-1-ona;
4-[5-etilsulfonil-2-(trans-4-hidroksicikloheksil)oksifenil]-7-fluoro-2-metilizokinolin-1-ona;
2-metil-4-[5-metilsulfonil-2-(oksolan-3-ilamino)fenil]izokinolin-1-ona;
2-metil-4-[5-metilsulfonil-2-(oksan-4-ilamino)fenil]izokinolin-1-ona;
4-[2-[(trans-4-hidroksicikloheksil)amino]-5-metilsulfonilfenil]-2-metilizokinolin-1-ona;
4-[2-(ciklopropilmetilamino)-5-etilsulfonilfenil]-2-metilizokinolin-1-ona;
4-[2-(ciklopropilmetilamino)-5-metilsulfonilfenil]-2-metilizokinolin-1-ona;
4-[2-(ciklopropilmetilamino)-5-etilsulfonilfenil]-7-fluoro-2-metilizokinolin-1-ona;
4-[2-(ciklopropilmetilamino)-5-metilsulfonilfenil]-7-fluoro-2-metilizokinolin-1-ona;
4-[2-(ciklopropilmetoksi)-5-metilsulfonilfenil]-2-metil-6-(trifluorometil)izokinolin-1-ona;
4-[2-(ciklopropilmetoksi)-5-metilsulfonilfenil]-6-metoksi-2-metilizokinolin-1-ona;
[4-(ciklopropilmetoksi)-3-(2-metil-1-oksoizokinolin-4-il)fenil]sulfamata;
N-[2-(2-metil-1-oksoizokinolin-4-il)-4-metilsulfonilfenil]-ciklopropanekarboksamida;
N-[2-(2-metil-1-oksoizokinolin-4-il)-4-metilsulfonilfenil]propanamida;
N-[2-(2-metil-1-oksoizokinolin-4-il)-4-metilsulfonilfenil]acetamida;
2-metil-4-(5-metilsulfonil-2-propylfenil)izokinolin-1-ona;
4-(2-etil-5-metilsulfonilfenil)-2-metilizokinolin-1-ona;
4-(2-butil-5-metilsulfonilfenil)-2-metilizokinolin-1-ona;
4-[2-(2-ciklopropiletil)-5-metilsulfonilfenil]-2-metilizokinolin-1-ona;
4-[2-(ciklopropilmetoksi)-5-propan-2-ilsulfonilfenil]-2-metilizokinolin-1-ona;
4-[2-(ciklopropilmetoksi)-5-propan-2-ilsulfonilfenil]-6-metoksi-2-metilizokinolin-1-ona;
4-[5-(etilsulfonilmetil)-2-(2,2,2-trifluoroetoksi)fenil]-2-metilizokinolin-1-ona; i
2-metil-4-[5-(metilsulfonilmetil)-2-(2,2,2-trifluoroetoksi)fenil]izokinolin-1-ona.
15. Spoj ili njegova farmaceutski prihvatljiva sol u skladu s patentnim zahtjevom 1, naznačen time, da ima strukturu koja je odabrana iz skupine koja se sastoji od
4-[2-(ciklopropilmetoksi)-5-metilsulfonilfenil]-2-metilizokinolin-1-ona,
4-[2-(ciklopropilmetoksi)-5-metilsulfonilfenil]-6-fluoro-2-metilizokinolin-1-ona,
4-[2-(ciklopropilmetoksi)-5-metilsulfonilfenil]-7-fluoro-2-metilizokinolin-1-ona,
4-[2-(2,4-difluorofenoksi)-5-metilsulfonilfenil]-2-metilizokinolin-1-ona, i
4-[2-(ciklopropilmetoksi)-5-etilsulfonilfenil]-2-metilizokinolin-1-ona.
16. Farmaceutski pripravak, naznačen time, da sadrži spoj ili njegovu farmaceutski prihvatljivu sol u skladu s bilo kojim od patentnih zahtjeva 1 do 15 i farmaceutski prihvatljivu pomoćnu tvar.
17. Spoj ili njegova farmaceutski prihvatljiva sol u skladu s bilo kojim od patentnih zahtjeva 1 do 15, ili farmaceutski pripravak iz patentnog zahtjeva 16, naznačen time, da se koristi kao lijek za liječenje karcinoma ili kao regulator transkripcije u stanici.
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PCT/US2014/061261 WO2015058160A1 (en) | 2013-10-18 | 2014-10-17 | Bromodomain inhibitors |
EP14854531.2A EP3057586B1 (en) | 2013-10-18 | 2014-10-17 | Bromodomain inhibitors |
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HRP20200341TT HRP20200341T1 (hr) | 2013-10-18 | 2020-02-28 | Bromodomenski (bet) inhibitori |
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