UA75060C2 - Substituted n-benzyl-indole-3-yl-glyoxylic acid derivatives having antitumor activity, use thereof and pharmaceutical composition based thereon - Google Patents
Substituted n-benzyl-indole-3-yl-glyoxylic acid derivatives having antitumor activity, use thereof and pharmaceutical composition based thereon Download PDFInfo
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- UA75060C2 UA75060C2 UA2002076107A UA2002076107A UA75060C2 UA 75060 C2 UA75060 C2 UA 75060C2 UA 2002076107 A UA2002076107 A UA 2002076107A UA 2002076107 A UA2002076107 A UA 2002076107A UA 75060 C2 UA75060 C2 UA 75060C2
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- Prior art keywords
- acid
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- alkyl
- substituted
- cooh
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 230000000259 anti-tumor effect Effects 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 239000002253 acid Substances 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 239000000725 suspension Substances 0.000 claims abstract description 10
- 239000003085 diluting agent Substances 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 4
- 150000007524 organic acids Chemical class 0.000 claims abstract description 4
- 235000005985 organic acids Nutrition 0.000 claims abstract description 4
- 239000002775 capsule Substances 0.000 claims abstract description 3
- 239000006071 cream Substances 0.000 claims abstract description 3
- 238000001802 infusion Methods 0.000 claims abstract description 3
- 239000002674 ointment Substances 0.000 claims abstract description 3
- 239000000829 suppository Substances 0.000 claims abstract description 3
- -1 nitro, amino Chemical group 0.000 claims description 48
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 4
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- 239000002246 antineoplastic agent Substances 0.000 claims description 3
- 125000005239 aroylamino group Chemical group 0.000 claims description 3
- 229940093915 gynecological organic acid Drugs 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 3
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 2
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 125000005421 aryl sulfonamido group Chemical group 0.000 claims description 2
- 235000010323 ascorbic acid Nutrition 0.000 claims description 2
- 239000011668 ascorbic acid Substances 0.000 claims description 2
- 229960005070 ascorbic acid Drugs 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- 239000000174 gluconic acid Substances 0.000 claims description 2
- 235000012208 gluconic acid Nutrition 0.000 claims description 2
- 229940097043 glucuronic acid Drugs 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000004310 lactic acid Substances 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 235000001968 nicotinic acid Nutrition 0.000 claims description 2
- 229960003512 nicotinic acid Drugs 0.000 claims description 2
- 239000011664 nicotinic acid Substances 0.000 claims description 2
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 239000008298 dragée Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 239000003826 tablet Substances 0.000 abstract description 2
- MRDIZANPJLYUKO-UHFFFAOYSA-N 2-(1-benzylindol-3-yl)-2-oxoacetic acid Chemical class C12=CC=CC=C2C(C(=O)C(=O)O)=CN1CC1=CC=CC=C1 MRDIZANPJLYUKO-UHFFFAOYSA-N 0.000 abstract 1
- 239000002671 adjuvant Substances 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 230000001173 tumoral effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 10
- 150000001408 amides Chemical class 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000000010 aprotic solvent Substances 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- AMANDCZTVNQSNB-UHFFFAOYSA-N glyoxamide Chemical compound NC(=O)C=O AMANDCZTVNQSNB-UHFFFAOYSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- DWLVFWDCSFTDOD-UHFFFAOYSA-N indol-3-yl-glyoxylic acid Natural products C1=CC=C2C(C(=O)C(=O)O)=CNC2=C1 DWLVFWDCSFTDOD-UHFFFAOYSA-N 0.000 description 4
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 4
- 239000012454 non-polar solvent Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
- 150000002475 indoles Chemical class 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- RVPTXIBMGYNFNG-UHFFFAOYSA-N 1-[(4-nitrophenyl)methyl]indole Chemical compound C1=CC([N+](=O)[O-])=CC=C1CN1C2=CC=CC=C2C=C1 RVPTXIBMGYNFNG-UHFFFAOYSA-N 0.000 description 2
- MQLACMBJVPINKE-UHFFFAOYSA-N 10-[(3-hydroxy-4-methoxyphenyl)methylidene]anthracen-9-one Chemical compound C1=C(O)C(OC)=CC=C1C=C1C2=CC=CC=C2C(=O)C2=CC=CC=C21 MQLACMBJVPINKE-UHFFFAOYSA-N 0.000 description 2
- WNZLDRIGCVYTOQ-UHFFFAOYSA-N 2-(1h-indol-2-yl)-2-oxoacetic acid Chemical compound C1=CC=C2NC(C(=O)C(=O)O)=CC2=C1 WNZLDRIGCVYTOQ-UHFFFAOYSA-N 0.000 description 2
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- KGCNHWXDPDPSBV-UHFFFAOYSA-N p-nitrobenzyl chloride Chemical compound [O-][N+](=O)C1=CC=C(CCl)C=C1 KGCNHWXDPDPSBV-UHFFFAOYSA-N 0.000 description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
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- 102000000587 Glycerolphosphate Dehydrogenase Human genes 0.000 description 1
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- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000006294 amino alkylene group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000004421 aryl sulphonamide group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 238000005574 benzylation reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000000368 destabilizing effect Effects 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 description 1
- 125000004475 heteroaralkyl group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000004688 microtubule Anatomy 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000000394 mitotic effect Effects 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- CBFZWGRQXZYRRR-UHFFFAOYSA-N pyridin-4-amine;hydrochloride Chemical compound Cl.NC1=CC=NC=C1 CBFZWGRQXZYRRR-UHFFFAOYSA-N 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical group C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
Classifications
-
- 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
- A61K31/44—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
-
- 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
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19962300A DE19962300A1 (de) | 1999-12-23 | 1999-12-23 | Substituierte N-Benzyl-Indol-3-yl-glyoxylsäure-Derivate mit Antitumorwirkung |
| PCT/EP2000/012947 WO2001047913A2 (de) | 1999-12-23 | 2000-12-19 | Substituierte n-benzyl-indol-3-yl- glyoxylsäure-derivate antitumorwirkung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA75060C2 true UA75060C2 (en) | 2006-03-15 |
Family
ID=7934006
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2002076107A UA75060C2 (en) | 1999-12-23 | 2000-12-19 | Substituted n-benzyl-indole-3-yl-glyoxylic acid derivatives having antitumor activity, use thereof and pharmaceutical composition based thereon |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US6432987B2 (no) |
| EP (1) | EP1240157B1 (no) |
| JP (1) | JP2003519137A (no) |
| KR (1) | KR100747425B1 (no) |
| CN (1) | CN1283637C (no) |
| AR (1) | AR027098A1 (no) |
| AT (1) | ATE259364T1 (no) |
| AU (1) | AU772745B2 (no) |
| BG (1) | BG106924A (no) |
| BR (1) | BR0016712A (no) |
| CA (1) | CA2395259A1 (no) |
| CO (1) | CO5251472A1 (no) |
| CZ (1) | CZ20022094A3 (no) |
| DE (2) | DE19962300A1 (no) |
| DK (1) | DK1240157T3 (no) |
| ES (1) | ES2215768T3 (no) |
| HK (1) | HK1054038B (no) |
| HU (1) | HUP0203716A3 (no) |
| IL (1) | IL150235A0 (no) |
| MX (1) | MXPA02006229A (no) |
| NO (1) | NO324750B1 (no) |
| NZ (2) | NZ519977A (no) |
| PL (1) | PL195014B1 (no) |
| PT (1) | PT1240157E (no) |
| RU (1) | RU2266280C2 (no) |
| SK (1) | SK8752002A3 (no) |
| TR (1) | TR200400601T4 (no) |
| TW (1) | TWI284128B (no) |
| UA (1) | UA75060C2 (no) |
| WO (1) | WO2001047913A2 (no) |
| ZA (1) | ZA200204896B (no) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19814838C2 (de) * | 1998-04-02 | 2001-01-18 | Asta Medica Ag | Indolyl-3-glyoxylsäure-Derivate mit Antitumorwirkung |
| DE19946301A1 (de) * | 1998-04-02 | 2001-04-19 | Asta Medica Ag | Indolyl-3-glyoxylsäure-Derivate mit therapeutisch wertvollen Eigenschaften |
| DE10037310A1 (de) * | 2000-07-28 | 2002-02-07 | Asta Medica Ag | Neue Indolderivate und deren Verwendung als Arzneimittel |
| DE10318611A1 (de) * | 2003-04-24 | 2004-11-11 | Elbion Ag | 4-, 6- oder 7-Hydroxyindole mit N-Oxidgruppen und deren Verwendung als Therapeutika |
| DE10318609A1 (de) * | 2003-04-24 | 2004-11-11 | Elbion Ag | 5-Hydroxyindole mit N-Oxidgruppen und deren Verwendung als Therapeutika |
| CA2526663C (en) * | 2003-06-05 | 2011-07-19 | Zentaris Gmbh | Indole derivatives with apoptosis-inducing effect |
| US7211588B2 (en) * | 2003-07-25 | 2007-05-01 | Zentaris Gmbh | N-substituted indolyl-3-glyoxylamides, their use as medicaments and process for their preparation |
| CN102060806A (zh) | 2003-09-11 | 2011-05-18 | iTherX药品公司 | 细胞因子抑制剂 |
| US7268159B2 (en) * | 2003-09-25 | 2007-09-11 | Wyeth | Substituted indoles |
| DE102004031538A1 (de) * | 2004-06-29 | 2006-02-09 | Baxter International Inc., Deerfield | Pharmazeutische Darreichungsform zur oralen Verabreichung eines schwerlöslichen Wirkstoffs, Verfahren zu deren Herstellung und Kit |
| ES2644450T3 (es) | 2004-12-31 | 2017-11-29 | Dr. Reddy's Laboratories Ltd. | Nuevos derivados de bencilamina como inhibidores de CETP |
| US8604055B2 (en) | 2004-12-31 | 2013-12-10 | Dr. Reddy's Laboratories Ltd. | Substituted benzylamino quinolines as cholesterol ester-transfer protein inhibitors |
| WO2006099256A2 (en) * | 2005-03-11 | 2006-09-21 | Vertex Pharmaceuticals Incorporated | Modulators of atp-binding cassette transporters |
| EP2049520A4 (en) | 2006-08-07 | 2011-01-05 | Ironwood Pharmaceuticals Inc | indole compounds |
| WO2008066807A1 (en) * | 2006-11-28 | 2008-06-05 | Ziopharm Oncology, Inc. | Use of indolyl-3-glyoxylic acid derivatives including indibulin, alone or in combination with further agents for treating cancer |
| EP3791880A1 (en) | 2009-04-29 | 2021-03-17 | Amarin Pharmaceuticals Ireland Limited | Pharmaceutical compositions comprising epa |
| AR084433A1 (es) | 2010-12-22 | 2013-05-15 | Ironwood Pharmaceuticals Inc | Inhibidores de la faah y composiciones farmaceuticas que los contienen |
| CA2845284C (en) | 2011-08-18 | 2018-03-06 | Dr. Reddy's Laboratories Ltd. | Substituted heterocyclic amine compounds as cholesteryl ester-transfer protein (cetp) inhibitors |
| JP6140168B2 (ja) | 2011-09-27 | 2017-05-31 | ドクター レディズ ラボラトリーズ リミテッド | アテローム性動脈硬化症の処置のために有用なコレステリルエステル転送タンパク質（ｃｅｔｐ）インヒビターとしての５−ベンジルアミノメチル−６−アミノピラゾロ［３，４−ｂ］ピリジン誘導体 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU665690B2 (en) * | 1992-05-08 | 1996-01-11 | Otsuka Pharmaceutical Factory, Inc. | Indole derivative |
| IL109311A0 (en) * | 1993-04-16 | 1994-07-31 | Lilly Co Eli | 1H-indole-3-acetamide sPla2 inhibitors |
| KR100362864B1 (ko) * | 1994-02-22 | 2003-04-16 | 메렐 파마슈티칼스 인크. | 에스트로겐관련신생물및질환의치료에유용한신규인돌유도체 |
| DK1950200T3 (da) * | 1994-04-01 | 2012-04-10 | Lilly Co Eli | [[3-(2-AMINO-1,2-DIOXOETHYL)-2-ETHYL-1-(PHENYLMETHYL)-11H-INDOL-4-YL]OXY]EDDIKESYREMETHYLESTER SOM sPLA2-INHIBITOR |
| DE19636150A1 (de) * | 1996-09-06 | 1998-03-12 | Asta Medica Ag | N-substituierte Indol-3-glyoxylamide mit antiasthmatischer, antiallergischer und immunsuppressiver/immunmodulierender Wirkung |
| EP0987250A4 (en) * | 1997-02-20 | 2000-12-06 | Shionogi & Co | INDOLDICARBONIC ACID DERIVATIVES |
| US5972988A (en) * | 1997-03-26 | 1999-10-26 | Eli Lilly And Company | Method for treatment of chronic bronchitis using indole compounds |
| WO1998047507A1 (en) * | 1997-04-24 | 1998-10-29 | Shionogi & Co., Ltd. | Method for the treatment of stroke using n-heterocyclic glyoxylamide compounds |
| TW455581B (en) * | 1997-06-26 | 2001-09-21 | Lilly Co Eli | Process for preparing 4-substituted-1H-indole-3-glyoxamides |
| EP1011670A4 (en) * | 1997-08-28 | 2004-10-27 | Lilly Co Eli | PROCESS FOR TREATING NON-RHUMATOID POLYARTHRITIS |
| JP2001517707A (ja) * | 1997-09-26 | 2001-10-09 | イーライ・リリー・アンド・カンパニー | 嚢胞性繊維症の処置方法 |
| AU1200899A (en) * | 1997-10-27 | 1999-05-17 | Eli Lilly And Company | Morpholino-n-ethyl ester prodrugs of indole spla2 inhibitors |
| WO1999021545A1 (en) * | 1997-10-27 | 1999-05-06 | Eli Lilly And Company | ISOPROPYL ESTER PRODRUGS OF INDOLE sPLA2 INHIBITORS |
| AU1279899A (en) * | 1997-10-27 | 1999-05-17 | Eli Lilly And Company | N,n-diethylglycolamido ester prodrugs of indole spla2 inhibitors |
| WO1999024033A1 (en) * | 1997-11-12 | 1999-05-20 | Shionogi & Co., Ltd. | Method for the treatment of disorders associated with apoptosis using n-heterocyclic glyoxylamide compounds |
| AU1405899A (en) * | 1997-11-14 | 1999-06-07 | Eli Lilly And Company | Treatment for alzheimer's disease |
| ID26250A (id) * | 1998-02-25 | 2000-12-07 | Genetics Inst | Inhibitor-inhibitor dari enzim-enzim fosfolipase |
| DE19814838C2 (de) * | 1998-04-02 | 2001-01-18 | Asta Medica Ag | Indolyl-3-glyoxylsäure-Derivate mit Antitumorwirkung |
| DZ2770A1 (fr) * | 1998-04-17 | 2003-12-01 | Lilly Co Eli | Procédé de préparation de 1h-indol-3 glyoxamides substituées en position 4. |
| TR200003130T2 (tr) * | 1998-04-28 | 2001-01-22 | Arzneimittelwerk Dresden Gmbh | Yeni hidroksiindoller, bunların fosfodiesteraz 4 inhibitörleri olarak kullanımları ve hazırlanmaları için işlemler |
| DE19818964A1 (de) * | 1998-04-28 | 1999-11-04 | Dresden Arzneimittel | Neue Hydroxyindole, deren Verwendung als Inhibitoren der Phospodiesterase 4 und Verfahren zu deren Herstellung |
| WO1999057100A1 (en) * | 1998-05-01 | 1999-11-11 | Eli Lilly And Company | Spla2 inhibitor compounds for treatment of disease |
| NZ507391A (en) * | 1998-05-01 | 2003-12-19 | Lilly Co Eli | The compound ((3-(2-amino-1,2-dioxoethyl)-2-methyl-1- (phenylmethyl)-1H-indol-4-yl)oxy)acetic acid N-morpholino ethyl ester and its use as a sPLA 2 inhibitor |
| AU4834200A (en) * | 1999-05-10 | 2000-11-21 | Protarga, Inc. | Fatty acid-n-substituted indol-3-glyoxyl-amide compositions and uses thereof |
| TWI269654B (en) * | 1999-09-28 | 2007-01-01 | Baxter Healthcare Sa | N-substituted indole-3-glyoxylamide compounds having anti-tumor action |
-
1999
- 1999-12-23 DE DE19962300A patent/DE19962300A1/de not_active Withdrawn
-
2000
- 2000-12-15 US US09/736,431 patent/US6432987B2/en not_active Expired - Fee Related
- 2000-12-19 AU AU20119/01A patent/AU772745B2/en not_active Ceased
- 2000-12-19 BR BR0016712-6A patent/BR0016712A/pt not_active Application Discontinuation
- 2000-12-19 JP JP2001549383A patent/JP2003519137A/ja not_active Withdrawn
- 2000-12-19 NZ NZ519977A patent/NZ519977A/en unknown
- 2000-12-19 SK SK875-2002A patent/SK8752002A3/sk unknown
- 2000-12-19 PL PL355684A patent/PL195014B1/pl unknown
- 2000-12-19 TW TW089127265A patent/TWI284128B/zh not_active IP Right Cessation
- 2000-12-19 CN CNB008182094A patent/CN1283637C/zh not_active Expired - Fee Related
- 2000-12-19 TR TR2004/00601T patent/TR200400601T4/xx unknown
- 2000-12-19 MX MXPA02006229A patent/MXPA02006229A/es active IP Right Grant
- 2000-12-19 CA CA002395259A patent/CA2395259A1/en not_active Abandoned
- 2000-12-19 UA UA2002076107A patent/UA75060C2/uk unknown
- 2000-12-19 AT AT00983349T patent/ATE259364T1/de not_active IP Right Cessation
- 2000-12-19 DK DK00983349T patent/DK1240157T3/da active
- 2000-12-19 WO PCT/EP2000/012947 patent/WO2001047913A2/de active IP Right Grant
- 2000-12-19 ES ES00983349T patent/ES2215768T3/es not_active Expired - Lifetime
- 2000-12-19 DE DE50005284T patent/DE50005284D1/de not_active Expired - Fee Related
- 2000-12-19 KR KR1020027007933A patent/KR100747425B1/ko not_active IP Right Cessation
- 2000-12-19 RU RU2002120462/04A patent/RU2266280C2/ru not_active IP Right Cessation
- 2000-12-19 EP EP00983349A patent/EP1240157B1/de not_active Expired - Lifetime
- 2000-12-19 HU HU0203716A patent/HUP0203716A3/hu unknown
- 2000-12-19 CZ CZ20022094A patent/CZ20022094A3/cs unknown
- 2000-12-19 PT PT00983349T patent/PT1240157E/pt unknown
- 2000-12-19 NZ NZ533731A patent/NZ533731A/en unknown
- 2000-12-19 IL IL15023500A patent/IL150235A0/xx not_active IP Right Cessation
- 2000-12-22 CO CO00097375A patent/CO5251472A1/es not_active Application Discontinuation
- 2000-12-22 AR ARP000106916A patent/AR027098A1/es not_active Application Discontinuation
-
2002
- 2002-06-19 ZA ZA200204896A patent/ZA200204896B/en unknown
- 2002-06-21 NO NO20023039A patent/NO324750B1/no unknown
- 2002-07-16 BG BG106924A patent/BG106924A/bg unknown
-
2003
- 2003-09-09 HK HK03106408.0A patent/HK1054038B/zh not_active IP Right Cessation
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