CA2946609A1 - Inhibiteurs de naphtaquinone methyltransferase et leurs utilisations - Google Patents
Inhibiteurs de naphtaquinone methyltransferase et leurs utilisations Download PDFInfo
- Publication number
- CA2946609A1 CA2946609A1 CA2946609A CA2946609A CA2946609A1 CA 2946609 A1 CA2946609 A1 CA 2946609A1 CA 2946609 A CA2946609 A CA 2946609A CA 2946609 A CA2946609 A CA 2946609A CA 2946609 A1 CA2946609 A1 CA 2946609A1
- Authority
- CA
- Canada
- Prior art keywords
- optionally substituted
- hydrogen
- compound
- alkyl
- hydrocarbyl
- 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.)
- Abandoned
Links
- 150000002791 naphthoquinones Chemical class 0.000 title description 3
- 239000003697 methyltransferase inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 234
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 81
- 238000000034 method Methods 0.000 claims abstract description 76
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 70
- 101001008816 Homo sapiens N-lysine methyltransferase KMT5A Proteins 0.000 claims abstract description 68
- 102100027771 N-lysine methyltransferase KMT5A Human genes 0.000 claims abstract description 67
- 201000010099 disease Diseases 0.000 claims abstract description 64
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 56
- 150000003839 salts Chemical class 0.000 claims abstract description 54
- 206010006187 Breast cancer Diseases 0.000 claims abstract description 42
- 201000011510 cancer Diseases 0.000 claims abstract description 42
- 208000026310 Breast neoplasm Diseases 0.000 claims abstract description 41
- 230000000694 effects Effects 0.000 claims abstract description 36
- 230000002062 proliferating effect Effects 0.000 claims abstract description 36
- 201000001441 melanoma Diseases 0.000 claims abstract description 25
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 23
- 208000032839 leukemia Diseases 0.000 claims abstract description 19
- 238000002372 labelling Methods 0.000 claims abstract description 11
- 208000037819 metastatic cancer Diseases 0.000 claims abstract description 9
- 208000011575 metastatic malignant neoplasm Diseases 0.000 claims abstract description 9
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 184
- 229910052739 hydrogen Inorganic materials 0.000 claims description 150
- 239000001257 hydrogen Substances 0.000 claims description 148
- 125000000623 heterocyclic group Chemical group 0.000 claims description 140
- 125000001072 heteroaryl group Chemical group 0.000 claims description 129
- 125000003118 aryl group Chemical group 0.000 claims description 87
- 229910052736 halogen Inorganic materials 0.000 claims description 83
- 125000001424 substituent group Chemical group 0.000 claims description 73
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 72
- 150000002367 halogens Chemical group 0.000 claims description 67
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 66
- 125000003545 alkoxy group Chemical group 0.000 claims description 64
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 64
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 63
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 62
- 125000002252 acyl group Chemical group 0.000 claims description 58
- 125000001188 haloalkyl group Chemical group 0.000 claims description 56
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 53
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 46
- 229910052757 nitrogen Inorganic materials 0.000 claims description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- 239000012472 biological sample Substances 0.000 claims description 30
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 26
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 22
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 11
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 11
- 229910052727 yttrium Inorganic materials 0.000 claims description 7
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000006659 (C1-C20) hydrocarbyl group Chemical group 0.000 claims description 4
- 206010027480 Metastatic malignant melanoma Diseases 0.000 claims description 3
- 208000021039 metastatic melanoma Diseases 0.000 claims description 3
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 42
- WNOYGCGQDNUSDN-UHFFFAOYSA-N CCCCC1=C(SC2=CC=CC=C2)C(=O)C2=C(C=CC=C2)C1=O Chemical compound CCCCC1=C(SC2=CC=CC=C2)C(=O)C2=C(C=CC=C2)C1=O WNOYGCGQDNUSDN-UHFFFAOYSA-N 0.000 claims 1
- 239000012453 solvate Substances 0.000 abstract description 29
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- 238000011282 treatment Methods 0.000 abstract description 22
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- 125000000217 alkyl group Chemical group 0.000 description 195
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- 125000004452 carbocyclyl group Chemical group 0.000 description 70
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- 125000005842 heteroatom Chemical group 0.000 description 51
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- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 42
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
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- 239000002246 antineoplastic agent Substances 0.000 description 28
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 25
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- 125000004122 cyclic group Chemical group 0.000 description 23
- 210000001519 tissue Anatomy 0.000 description 23
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 22
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 21
- 125000000753 cycloalkyl group Chemical group 0.000 description 20
- 125000005843 halogen group Chemical group 0.000 description 20
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 description 19
- 125000004404 heteroalkyl group Chemical group 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
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- 239000003755 preservative agent Substances 0.000 description 17
- 241001465754 Metazoa Species 0.000 description 16
- 102000016397 Methyltransferase Human genes 0.000 description 16
- 108060004795 Methyltransferase Proteins 0.000 description 16
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 16
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 16
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- 229910052760 oxygen Inorganic materials 0.000 description 16
- 239000001301 oxygen Substances 0.000 description 16
- 229910052717 sulfur Inorganic materials 0.000 description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 239000011593 sulfur Chemical group 0.000 description 15
- 239000000843 powder Substances 0.000 description 14
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 12
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 12
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- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 11
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- 125000003107 substituted aryl group Chemical group 0.000 description 11
- 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 description 10
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- 229960001295 tocopherol Drugs 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000005881 triazolinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
- 229940117013 triethanolamine oleate Drugs 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960005066 trisodium edetate Drugs 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 230000003827 upregulation Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 208000037965 uterine sarcoma Diseases 0.000 description 1
- 206010046885 vaginal cancer Diseases 0.000 description 1
- 208000013139 vaginal neoplasm Diseases 0.000 description 1
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- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 201000005102 vulva cancer Diseases 0.000 description 1
- 208000028010 vulval Paget disease Diseases 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000008170 walnut oil Substances 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
- 229940033942 zoladex Drugs 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/10—Quinones the quinoid structure being part of a condensed ring system containing two rings
- C07C50/12—Naphthoquinones, i.e. C10H6O2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/30—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
- C07C233/32—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/30—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/10—Quinones the quinoid structure being part of a condensed ring system containing two rings
- C07C50/14—Quinones the quinoid structure being part of a condensed ring system containing two rings with unsaturation outside the ring system, e.g. vitamin K1
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/112—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- C07D295/116—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings with the doubly bound oxygen or sulfur atoms directly attached to a carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B13/00—Oxyketone dyes
- C09B13/02—Oxyketone dyes of the naphthalene series, e.g. naphthazarin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201461990905P | 2014-05-09 | 2014-05-09 | |
US61/990,905 | 2014-05-09 | ||
US201462033938P | 2014-08-06 | 2014-08-06 | |
US62/033,938 | 2014-08-06 | ||
PCT/US2015/029977 WO2015172076A1 (fr) | 2014-05-09 | 2015-05-08 | Inhibiteurs de naphtaquinone méthyltransférase et leurs utilisations |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2946609A1 true CA2946609A1 (fr) | 2015-11-12 |
Family
ID=54393067
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2946609A Abandoned CA2946609A1 (fr) | 2014-05-09 | 2015-05-08 | Inhibiteurs de naphtaquinone methyltransferase et leurs utilisations |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP3140274A1 (fr) |
JP (1) | JP2017515900A (fr) |
AU (1) | AU2015255692A1 (fr) |
CA (1) | CA2946609A1 (fr) |
WO (1) | WO2015172076A1 (fr) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
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CN107879958B (zh) * | 2017-10-30 | 2019-07-19 | 黑龙江八一农垦大学 | 2-(4-甲氧基苯巯基)-5,8-二甲氧基-1,4-萘醌及其制备方法和含其的药物 |
CN109574959A (zh) * | 2019-01-16 | 2019-04-05 | 郑州大学 | 一种硫胺化1,4-萘醌化合物及其制备方法 |
CN111620840B (zh) * | 2020-06-17 | 2023-06-30 | 温州医科大学 | 一种2-吗啉基-3-芳硒基萘醌的合成方法 |
CN111606843A (zh) * | 2020-06-17 | 2020-09-01 | 温州医科大学 | 一种2-苯硒基-3-胺基-1,4-萘醌的合成方法 |
IL301739A (en) | 2020-10-05 | 2023-05-01 | Enliven Therapeutics Inc | 5- and 6-Azaindole compounds for inhibition of BCR-ABL tyrosine kinases |
CN115093338A (zh) * | 2021-09-24 | 2022-09-23 | 洛阳职业技术学院 | 一种靶向抑制维生素k循环的小分子化合物的合成方法 |
WO2023078252A1 (fr) | 2021-11-02 | 2023-05-11 | Flare Therapeutics Inc. | Agonistes inverses de pparg et leurs utilisations |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2522379C (fr) * | 2003-04-10 | 2012-10-23 | Chiron Corporation | Le coronavirus du syndrome respiratoire aigu grave |
EP2601527A1 (fr) * | 2010-08-05 | 2013-06-12 | Cellzome AG | Procédés pour l'identification de molécules interagissant avec la méthyltransférase et pour la purification de protéines de type méthyltransférase |
-
2015
- 2015-05-08 AU AU2015255692A patent/AU2015255692A1/en not_active Abandoned
- 2015-05-08 EP EP15788940.3A patent/EP3140274A1/fr not_active Withdrawn
- 2015-05-08 JP JP2017511562A patent/JP2017515900A/ja active Pending
- 2015-05-08 CA CA2946609A patent/CA2946609A1/fr not_active Abandoned
- 2015-05-08 WO PCT/US2015/029977 patent/WO2015172076A1/fr active Application Filing
Also Published As
Publication number | Publication date |
---|---|
AU2015255692A1 (en) | 2016-11-03 |
JP2017515900A (ja) | 2017-06-15 |
WO2015172076A1 (fr) | 2015-11-12 |
EP3140274A1 (fr) | 2017-03-15 |
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