UA75872C2 - Indolyl-3- glyoxylic acid with useful therapeutic properties - Google Patents
Indolyl-3- glyoxylic acid with useful therapeutic properties Download PDFInfo
- Publication number
- UA75872C2 UA75872C2 UA2002043433A UA2002043433A UA75872C2 UA 75872 C2 UA75872 C2 UA 75872C2 UA 2002043433 A UA2002043433 A UA 2002043433A UA 2002043433 A UA2002043433 A UA 2002043433A UA 75872 C2 UA75872 C2 UA 75872C2
- Authority
- UA
- Ukraine
- Prior art keywords
- group
- alkyl
- radical
- acid
- glyoxylamide
- Prior art date
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- HHLFWLYXYJOTON-UHFFFAOYSA-N Glyoxylic acid Natural products OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- -1 N-substituted indol-3- glyoxylamides Chemical class 0.000 claims abstract description 33
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 230000033115 angiogenesis Effects 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 230000002401 inhibitory effect Effects 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 8
- AWMLDBKLOPNOAR-UHFFFAOYSA-N 2-(1h-indol-3-yl)-2-oxoacetamide Chemical class C1=CC=C2C(C(=O)C(=O)N)=CNC2=C1 AWMLDBKLOPNOAR-UHFFFAOYSA-N 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 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
- 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
- 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- 125000001495 ethyl group Chemical class [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 238000001802 infusion Methods 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 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
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000000999 tert-butyl group Chemical class [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 2
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical group C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 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
- 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
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 150000002148 esters Chemical class 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
- 229910052500 inorganic mineral Inorganic materials 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
- 239000011707 mineral Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000002674 ointment 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
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 239000001384 succinic acid Substances 0.000 claims description 2
- 239000000829 suppository Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 230000014399 negative regulation of angiogenesis Effects 0.000 claims 2
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 claims 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
- 125000006294 amino alkylene group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 abstract description 13
- 239000003814 drug Substances 0.000 abstract description 6
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- 206010059866 Drug resistance Diseases 0.000 abstract description 4
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- 206010044221 Toxic encephalopathy Diseases 0.000 abstract description 4
- 231100000228 neurotoxicity Toxicity 0.000 abstract description 4
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- 239000004037 angiogenesis inhibitor Substances 0.000 abstract description 2
- 229940121369 angiogenesis inhibitor Drugs 0.000 abstract description 2
- 208000011645 metastatic carcinoma Diseases 0.000 abstract 1
- 206010061289 metastatic neoplasm Diseases 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 description 19
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- 239000002246 antineoplastic agent Substances 0.000 description 9
- 230000005012 migration Effects 0.000 description 8
- 238000013508 migration Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
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- 229940079593 drug Drugs 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- 230000001772 anti-angiogenic effect Effects 0.000 description 4
- 210000004204 blood vessel Anatomy 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000004614 tumor growth Effects 0.000 description 4
- 229940041181 antineoplastic drug Drugs 0.000 description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
- 230000012292 cell migration Effects 0.000 description 3
- 230000009401 metastasis Effects 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
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- 206010048723 Multiple-drug resistance Diseases 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 230000001740 anti-invasion Effects 0.000 description 2
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- 238000011319 anticancer therapy Methods 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 238000004113 cell culture Methods 0.000 description 2
- 230000030833 cell death Effects 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- 231100000433 cytotoxic Toxicity 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 231100000518 lethal Toxicity 0.000 description 2
- 230000001665 lethal effect Effects 0.000 description 2
- 238000004393 prognosis Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- VEEGZPWAAPPXRB-BJMVGYQFSA-N (3e)-3-(1h-imidazol-5-ylmethylidene)-1h-indol-2-one Chemical compound O=C1NC2=CC=CC=C2\C1=C/C1=CN=CN1 VEEGZPWAAPPXRB-BJMVGYQFSA-N 0.000 description 1
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 101100393871 Arabidopsis thaliana GT12 gene Proteins 0.000 description 1
- 206010003591 Ataxia Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 1
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 1
- 201000008808 Fibrosarcoma Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 108700041567 MDR Genes Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010029113 Neovascularisation Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010064390 Tumour invasion Diseases 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000033 alkoxyamino group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 230000004219 arterial function Effects 0.000 description 1
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- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 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
- 230000009400 cancer invasion Effects 0.000 description 1
- 125000005111 carboxyalkoxy group Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000021164 cell adhesion Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000004709 cell invasion Effects 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000000052 comparative effect Effects 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
- 239000000824 cytostatic agent Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 230000034994 death Effects 0.000 description 1
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- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 210000002889 endothelial cell Anatomy 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 description 1
- 210000002744 extracellular matrix Anatomy 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000009454 functional inhibition Effects 0.000 description 1
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
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- 201000005787 hematologic cancer Diseases 0.000 description 1
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- 230000002452 interceptive effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
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- 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
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- 230000000750 progressive effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 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
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- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
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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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19946301A DE19946301A1 (de) | 1998-04-02 | 1999-09-28 | Indolyl-3-glyoxylsäure-Derivate mit therapeutisch wertvollen Eigenschaften |
| PCT/EP2000/009390 WO2001022954A2 (fr) | 1999-09-28 | 2000-09-26 | Derives d"acide indolyl-3-glyoxyle a bonnes proprietes therapeutiques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA75872C2 true UA75872C2 (en) | 2006-06-15 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2002043433A UA75872C2 (en) | 1999-09-28 | 2000-09-26 | Indolyl-3- glyoxylic acid with useful therapeutic properties |
Country Status (32)
| Country | Link |
|---|---|
| EP (1) | EP1218006B1 (fr) |
| JP (1) | JP2003510274A (fr) |
| KR (1) | KR100759242B1 (fr) |
| CN (1) | CN1301712C (fr) |
| AR (1) | AR025885A1 (fr) |
| AT (1) | ATE459356T1 (fr) |
| AU (1) | AU783436B2 (fr) |
| BG (1) | BG106639A (fr) |
| BR (1) | BR0014378A (fr) |
| CA (1) | CA2386069C (fr) |
| CZ (1) | CZ303246B6 (fr) |
| DE (1) | DE50015879D1 (fr) |
| DZ (1) | DZ3196A1 (fr) |
| EE (1) | EE200200169A (fr) |
| ES (1) | ES2342042T3 (fr) |
| GE (1) | GEP20043250B (fr) |
| HK (1) | HK1048941B (fr) |
| HR (1) | HRP20020369A2 (fr) |
| HU (1) | HUP0202788A3 (fr) |
| IL (2) | IL148670A0 (fr) |
| IS (1) | IS6319A (fr) |
| MX (1) | MXPA02002824A (fr) |
| NO (1) | NO322614B1 (fr) |
| NZ (1) | NZ517988A (fr) |
| PL (1) | PL199576B1 (fr) |
| RS (1) | RS51302B (fr) |
| RU (1) | RU2282444C2 (fr) |
| SK (1) | SK287533B6 (fr) |
| TW (1) | TWI269654B (fr) |
| UA (1) | UA75872C2 (fr) |
| WO (1) | WO2001022954A2 (fr) |
| ZA (1) | ZA200202556B (fr) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19962300A1 (de) * | 1999-12-23 | 2001-06-28 | Asta Medica Ag | Substituierte N-Benzyl-Indol-3-yl-glyoxylsäure-Derivate mit Antitumorwirkung |
| US7030123B2 (en) | 2000-05-31 | 2006-04-18 | Astrazeneca Ab | Indole derivatives with vascular damaging activity |
| DE10037310A1 (de) | 2000-07-28 | 2002-02-07 | Asta Medica Ag | Neue Indolderivate und deren Verwendung als Arzneimittel |
| EP1484329A1 (fr) * | 2003-06-06 | 2004-12-08 | Zentaris GmbH | Dérivés d'indole déstinés à l'induction d'apoptose |
| EP1595878A1 (fr) * | 2004-05-15 | 2005-11-16 | Zentaris GmbH | Derives d'indole destines a l'induction d'apoptose |
| NZ543853A (en) * | 2003-06-05 | 2009-09-25 | Zentaris Gmbh | Indole derivatives with apoptosis-inducing effect |
| US20050124623A1 (en) | 2003-11-26 | 2005-06-09 | Bender John A. | Diazaindole-dicarbonyl-piperazinyl antiviral agents |
| CN103356636A (zh) * | 2004-05-23 | 2013-10-23 | 杰勒德·M·豪斯 | Theramutein调节剂 |
| BRPI0517652A (pt) * | 2004-11-08 | 2008-10-14 | Baxter Healthcare Sa | composições farmacêuticas nanoparticuladas de inibidores de tubulina, métodos para as suas preparações e respectivos usos |
| US20060100432A1 (en) | 2004-11-09 | 2006-05-11 | Matiskella John D | Crystalline materials of 1-(4-benzoyl-piperazin-1-yl)-2-[4-methoxy-7-(3-methyl-[1,2,4]triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-ethane-1,2-dione |
| US8604055B2 (en) | 2004-12-31 | 2013-12-10 | Dr. Reddy's Laboratories Ltd. | Substituted benzylamino quinolines as cholesterol ester-transfer protein inhibitors |
| KR101238525B1 (ko) | 2004-12-31 | 2013-02-28 | 레디 유에스 테라퓨틱스 인코포레이티드 | Ｃｅｔｐ 저해제로서의 신규 벤질아민 유도체 |
| US7851476B2 (en) | 2005-12-14 | 2010-12-14 | Bristol-Myers Squibb Company | Crystalline forms of 1-benzoyl-4-[2-[4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-YL)-1-[(phosphonooxy)methyl]-1H-pyrrolo[2,3-C]pyridin-3-YL]-1,2-dioxoethyl]-piperazine |
| US7807671B2 (en) | 2006-04-25 | 2010-10-05 | Bristol-Myers Squibb Company | Diketo-piperazine and piperidine derivatives as antiviral agents |
| JP2010511041A (ja) * | 2006-11-28 | 2010-04-08 | ジオファーム オンコロジー， インコーポレイテッド | インジブリンを含むインドリル−３−グリオキシル酸誘導体の癌を処置するための単独またはさらなる薬剤との組み合わせでの使用 |
| CN103827105B (zh) | 2011-08-18 | 2016-08-17 | 雷迪博士实验室有限公司 | 作为胆固醇酯转移蛋白(cetp)抑制剂的取代的杂环胺化合物 |
| 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 |
| US9353150B2 (en) | 2012-12-04 | 2016-05-31 | Massachusetts Institute Of Technology | Substituted pyrazino[1′,2′:1 ,5]pyrrolo[2,3-b]-indole-1,4-diones for cancer treatment |
| AU2014228822A1 (en) | 2013-03-15 | 2015-10-01 | Memorial Sloan-Kettering Cancer Center | HSP90-targeted cardiac imaging and therapy |
| US10918627B2 (en) | 2016-05-11 | 2021-02-16 | Massachusetts Institute Of Technology | Convergent and enantioselective total synthesis of Communesin analogs |
| WO2018209239A1 (fr) | 2017-05-11 | 2018-11-15 | Massachusetts Institute Of Technology | Dérivés d'agélastatine puissants en tant que modulateurs de l'invasion et de la métastase du cancer |
| CN109111501B (zh) * | 2017-06-23 | 2022-04-22 | 首都医科大学 | 脂肪氨基酸修饰的吲哚乙醇衍生物, 其合成，活性和应用 |
| US10640508B2 (en) | 2017-10-13 | 2020-05-05 | Massachusetts Institute Of Technology | Diazene directed modular synthesis of compounds with quaternary carbon centers |
| US11535634B2 (en) | 2019-06-05 | 2022-12-27 | Massachusetts Institute Of Technology | Compounds, conjugates, and compositions of epipolythiodiketopiperazines and polythiodiketopiperazines and uses thereof |
| WO2022182415A1 (fr) | 2021-02-24 | 2022-09-01 | Massachusetts Institute Of Technology | Dérivés d'himastatine, leurs procédés de préparation et leurs utilisations |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU4128089A (en) | 1988-09-15 | 1990-03-22 | Rorer International (Overseas) Inc. | Monoclonal antibodies specific to human epidermal growth factor receptor and therapeutic methods employing same |
| JP3163631B2 (ja) * | 1992-10-20 | 2001-05-08 | 東レ株式会社 | 好酸球浸潤抑制剤 |
| DE19636150A1 (de) * | 1996-09-06 | 1998-03-12 | Asta Medica Ag | N-substituierte Indol-3-glyoxylamide mit antiasthmatischer, antiallergischer und immunsuppressiver/immunmodulierender Wirkung |
| CA2286038A1 (fr) | 1997-04-08 | 1998-10-15 | Banyu Pharmaceutical Co., Ltd. | Gene associe a la metastase cancereuse |
| GEP20032920B (en) * | 1998-02-25 | 2003-03-25 | Genetics Inst | Inhibitors of Phospholipase Enzymes |
| WO1999046237A1 (fr) * | 1998-03-12 | 1999-09-16 | Novo Nordisk A/S | Modulateurs de proteine-tyrosine-phosphatases |
| DE19814838C2 (de) * | 1998-04-02 | 2001-01-18 | Asta Medica Ag | Indolyl-3-glyoxylsäure-Derivate mit Antitumorwirkung |
| ES2222706T3 (es) * | 1998-04-28 | 2005-02-01 | Elbion Ag | Nuevos hidroxiindoles, su utilizacion como inhibidores de la fosfodiesterasa 4, y procedimiento para su preparacion. |
| JP2000239252A (ja) * | 1999-02-16 | 2000-09-05 | Mitsubishi Chemicals Corp | インドール誘導体 |
| AU4834200A (en) * | 1999-05-10 | 2000-11-21 | Protarga, Inc. | Fatty acid-n-substituted indol-3-glyoxyl-amide compositions and uses thereof |
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2000
- 2000-09-22 TW TW089119680A patent/TWI269654B/zh not_active IP Right Cessation
- 2000-09-26 CA CA2386069A patent/CA2386069C/fr not_active Expired - Fee Related
- 2000-09-26 BR BR0014378-2A patent/BR0014378A/pt not_active Application Discontinuation
- 2000-09-26 ES ES00967789T patent/ES2342042T3/es not_active Expired - Lifetime
- 2000-09-26 SK SK407-2002A patent/SK287533B6/sk not_active IP Right Cessation
- 2000-09-26 UA UA2002043433A patent/UA75872C2/uk unknown
- 2000-09-26 RS YUP-227/02A patent/RS51302B/sr unknown
- 2000-09-26 DZ DZ003196A patent/DZ3196A1/fr active
- 2000-09-26 RU RU2002111866/15A patent/RU2282444C2/ru not_active IP Right Cessation
- 2000-09-26 CN CNB008134499A patent/CN1301712C/zh not_active Expired - Fee Related
- 2000-09-26 EP EP00967789A patent/EP1218006B1/fr not_active Expired - Lifetime
- 2000-09-26 GE GEAP20006425A patent/GEP20043250B/en unknown
- 2000-09-26 HU HU0202788A patent/HUP0202788A3/hu unknown
- 2000-09-26 AU AU77829/00A patent/AU783436B2/en not_active Ceased
- 2000-09-26 NZ NZ517988A patent/NZ517988A/en not_active IP Right Cessation
- 2000-09-26 PL PL364811A patent/PL199576B1/pl not_active IP Right Cessation
- 2000-09-26 KR KR1020027003937A patent/KR100759242B1/ko not_active IP Right Cessation
- 2000-09-26 AT AT00967789T patent/ATE459356T1/de not_active IP Right Cessation
- 2000-09-26 JP JP2001526166A patent/JP2003510274A/ja active Pending
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- 2000-09-26 WO PCT/EP2000/009390 patent/WO2001022954A2/fr active IP Right Grant
- 2000-09-26 MX MXPA02002824A patent/MXPA02002824A/es active IP Right Grant
- 2000-09-26 DE DE50015879T patent/DE50015879D1/de not_active Expired - Lifetime
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