HUE029370T2 - Rákellenes aktivitású vegyületek - Google Patents
Rákellenes aktivitású vegyületek Download PDFInfo
- Publication number
- HUE029370T2 HUE029370T2 HUE08829410A HUE08829410A HUE029370T2 HU E029370 T2 HUE029370 T2 HU E029370T2 HU E08829410 A HUE08829410 A HU E08829410A HU E08829410 A HUE08829410 A HU E08829410A HU E029370 T2 HUE029370 T2 HU E029370T2
- Authority
- HU
- Hungary
- Prior art keywords
- optionally substituted
- amino
- methyl
- pyridyl
- chloro
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 255
- 230000001093 anti-cancer Effects 0.000 title claims description 7
- -1 oxyloxy Chemical group 0.000 claims description 186
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 141
- 238000000034 method Methods 0.000 claims description 105
- 125000003118 aryl group Chemical group 0.000 claims description 99
- 125000000217 alkyl group Chemical group 0.000 claims description 82
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 79
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 76
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 74
- 239000000203 mixture Substances 0.000 claims description 74
- 125000001424 substituent group Chemical group 0.000 claims description 59
- 125000005110 aryl thio group Chemical group 0.000 claims description 49
- 125000002252 acyl group Chemical group 0.000 claims description 42
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 39
- 125000004414 alkyl thio group Chemical group 0.000 claims description 33
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 30
- 125000003107 substituted aryl group Chemical group 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 230000002062 proliferating effect Effects 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 230000006978 adaptation Effects 0.000 claims description 22
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 22
- 125000004104 aryloxy group Chemical group 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 20
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 238000000338 in vitro Methods 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 15
- 230000002147 killing effect Effects 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 230000001413 cellular effect Effects 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000004193 piperazinyl group Chemical group 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
- 241001024304 Mino Species 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 230000001939 inductive effect Effects 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 3
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 239000001294 propane Substances 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical class OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 claims 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- 101100190464 Caenorhabditis elegans pid-2 gene Proteins 0.000 claims 1
- AIKKULXCBHRFOS-UHFFFAOYSA-N Formothion Chemical group COP(=S)(OC)SCC(=O)N(C)C=O AIKKULXCBHRFOS-UHFFFAOYSA-N 0.000 claims 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 claims 1
- 241001391926 Neea Species 0.000 claims 1
- 241001387976 Pera Species 0.000 claims 1
- 230000005856 abnormality Effects 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- 125000001118 alkylidene group Chemical group 0.000 claims 1
- 125000001769 aryl amino group Chemical group 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000004803 chlorobenzyl group Chemical group 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000002009 diols Chemical class 0.000 claims 1
- 125000005313 fatty acid group Chemical group 0.000 claims 1
- 101150043124 kmo-1 gene Proteins 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000013011 mating Effects 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 229920001296 polysiloxane Polymers 0.000 claims 1
- IKNCGYCHMGNBCP-UHFFFAOYSA-N propan-1-olate Chemical compound CCC[O-] IKNCGYCHMGNBCP-UHFFFAOYSA-N 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 210000002966 serum Anatomy 0.000 claims 1
- 230000001256 tonic effect Effects 0.000 claims 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 1
- 210000004027 cell Anatomy 0.000 description 308
- 239000000543 intermediate Substances 0.000 description 77
- 206010028980 Neoplasm Diseases 0.000 description 71
- 238000011282 treatment Methods 0.000 description 63
- 230000037060 G2 phase arrest Effects 0.000 description 48
- 201000011510 cancer Diseases 0.000 description 48
- 241000699670 Mus sp. Species 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 38
- 239000002904 solvent Substances 0.000 description 38
- 241000282414 Homo sapiens Species 0.000 description 33
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- 230000005778 DNA damage Effects 0.000 description 32
- 231100000277 DNA damage Toxicity 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- 208000035269 cancer or benign tumor Diseases 0.000 description 27
- 235000019439 ethyl acetate Nutrition 0.000 description 27
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- 230000022131 cell cycle Effects 0.000 description 26
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- 229960003957 dexamethasone Drugs 0.000 description 19
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 230000003013 cytotoxicity Effects 0.000 description 17
- 231100000135 cytotoxicity Toxicity 0.000 description 17
- 230000005855 radiation Effects 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
- 230000004663 cell proliferation Effects 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 230000010190 G1 phase Effects 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
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- 239000012267 brine Substances 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- 238000004809 thin layer chromatography Methods 0.000 description 12
- 238000002054 transplantation Methods 0.000 description 12
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 12
- 239000012623 DNA damaging agent Substances 0.000 description 11
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- RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 description 11
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- 108091003079 Bovine Serum Albumin Proteins 0.000 description 10
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 10
- 239000012894 fetal calf serum Substances 0.000 description 10
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- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
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- MZTRIZBHLSXPLR-UHFFFAOYSA-N 1-[[6-benzyl-5-(trifluoromethyl)pyridin-2-yl]amino]-3,4-dimethylpyrrole-2,5-dione Chemical compound O=C1C(C)=C(C)C(=O)N1NC1=CC=C(C(F)(F)F)C(CC=2C=CC=CC=2)=N1 MZTRIZBHLSXPLR-UHFFFAOYSA-N 0.000 description 8
- AJJLKXUFMLSMAK-UHFFFAOYSA-N 1-[[6-chloro-5-(trifluoromethyl)pyridin-2-yl]amino]-3-methyl-4-(3-methylbutyl)pyrrole-2,5-dione Chemical compound O=C1C(CCC(C)C)=C(C)C(=O)N1NC1=CC=C(C(F)(F)F)C(Cl)=N1 AJJLKXUFMLSMAK-UHFFFAOYSA-N 0.000 description 8
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- UKJRLNJDHAAXBH-UHFFFAOYSA-N 3,4-dimethyl-1-[[4-(trifluoromethyl)quinolin-2-yl]amino]pyrrole-2,5-dione Chemical compound O=C1C(C)=C(C)C(=O)N1NC1=CC(C(F)(F)F)=C(C=CC=C2)C2=N1 UKJRLNJDHAAXBH-UHFFFAOYSA-N 0.000 description 7
- NCHWAOFXSKUWFY-UHFFFAOYSA-N 3-(butoxymethyl)-1-[[6-chloro-5-(trifluoromethyl)pyridin-2-yl]amino]-4-methylpyrrole-2,5-dione Chemical compound O=C1C(COCCCC)=C(C)C(=O)N1NC1=CC=C(C(F)(F)F)C(Cl)=N1 NCHWAOFXSKUWFY-UHFFFAOYSA-N 0.000 description 7
- IFXWZAPBANIBTK-UHFFFAOYSA-N 3-butyl-1-[[6-chloro-5-(trifluoromethyl)pyridin-2-yl]amino]-4-methylpyrrole-2,5-dione Chemical compound O=C1C(CCCC)=C(C)C(=O)N1NC1=CC=C(C(F)(F)F)C(Cl)=N1 IFXWZAPBANIBTK-UHFFFAOYSA-N 0.000 description 7
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- GGZMTTCIDWSCQV-UHFFFAOYSA-N 2-[[6-chloro-5-(trifluoromethyl)pyridin-2-yl]amino]-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound N1=C(Cl)C(C(F)(F)F)=CC=C1NN1C(=O)C(CCCC2)=C2C1=O GGZMTTCIDWSCQV-UHFFFAOYSA-N 0.000 description 6
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- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 6
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- ZGYRTJADPPDDMY-UHFFFAOYSA-N titanium;tetrahydrate Chemical compound O.O.O.O.[Ti] ZGYRTJADPPDDMY-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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- 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
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
- C07D207/452—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/50—Nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07—ORGANIC CHEMISTRY
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
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- Engineering & Computer Science (AREA)
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- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
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| US8227202B2 (en) | 2008-07-10 | 2012-07-24 | Nodality, Inc. | Methods for diagnosis, prognosis and methods of treatment |
| CN104523661A (zh) * | 2009-02-06 | 2015-04-22 | 南加利福尼亚大学 | 含有单萜的治疗组合物 |
| US20100215644A1 (en) * | 2009-02-25 | 2010-08-26 | Nodality, Inc. A Delaware Corporation | Analysis of nodes in cellular pathways |
| CN104744215B (zh) | 2010-03-03 | 2019-03-15 | 尼昂克技术公司 | 包含单萜的药物组合物 |
| US20160038600A1 (en) | 2012-08-03 | 2016-02-11 | Neonc Technologies Inc. | Pharmaceutical compositions comprising poh derivatives |
| EP2609064B1 (en) | 2010-08-27 | 2016-09-28 | Neonc Technologies Inc. | Pharmaceutical compositions comprising derivatives of perillyl alcohol |
| DK2651864T3 (en) | 2010-12-17 | 2016-09-05 | Neonc Tech Inc | Methods and devices for use of isoperillylalkohol |
| WO2013020024A2 (en) * | 2011-08-03 | 2013-02-07 | Karyopharm Therapeutics, Inc. | Maleimide compounds and methods of treatment |
| US9814693B2 (en) | 2012-05-09 | 2017-11-14 | Delmar Pharmaceuticals, Inc. | Veterinary use of dianhydrogalactitol, diacetyldianhydrogalactitol, and dibromodulcitol to treat malignancies |
| CN104781257A (zh) | 2012-06-14 | 2015-07-15 | 第一三共株式会社 | 哌啶基吡唑并吡啶衍生物 |
| JP2016506921A (ja) * | 2013-01-30 | 2016-03-07 | バイエル ファーマ アクチエンゲゼルシャフト | アミノ置換イソチアゾール |
| US9540462B2 (en) | 2014-12-05 | 2017-01-10 | Massachusetts Institute Of Technology | Catechol-rich polymers from N-substituted maleimides |
| WO2016119052A1 (en) | 2015-01-26 | 2016-08-04 | Ottawa Hospital Research Institute | Compositions and methods for enhancing oncolytic virus efficacy |
| EP3872069A1 (en) | 2015-02-12 | 2021-09-01 | Neonc Technologies, Inc. | Pharmaceutical compositions comprising perillyl alcohol derivatives |
| WO2017157885A1 (de) | 2016-03-16 | 2017-09-21 | Bayer Cropscience Aktiengesellschaft | N-(cyanbenzyl)-6-(cyclopropylcarbonylamino)-4-(phenyl)-pyridin-2-carboxamid-derivate und verwandte verbindungen als pestizide pflanzenschutzmittel |
| USD915100S1 (en) | 2016-03-31 | 2021-04-06 | Ocean 22, Llc | Spooled item holding device |
| USD801721S1 (en) | 2016-03-31 | 2017-11-07 | Patricia Grayson Briden | Spooled item holding device |
| TW201811766A (zh) | 2016-08-29 | 2018-04-01 | 瑞士商諾華公司 | N-(吡啶-2-基)吡啶-磺醯胺衍生物及其用於疾病治療之用途 |
| US12419832B2 (en) | 2018-01-29 | 2025-09-23 | Cognos Therapeutics, Inc. | Intratumoral delivery of bortezomib |
| JOP20200187A1 (ar) | 2018-02-02 | 2020-07-29 | Boehringer Ingelheim Int | مشتقات ترايازولو بيريميدين للاستخدام كمثبطات جريلين o- أسيل ترانسفيراز (goat) |
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