RU2262339C2 - Производные индолил-3-глиоксиловой кислоты - соединения, обладающие противоопухолевой активностью, фармацевтическая композиция, противоопухолевое средство (варианты) - Google Patents
Производные индолил-3-глиоксиловой кислоты - соединения, обладающие противоопухолевой активностью, фармацевтическая композиция, противоопухолевое средство (варианты) Download PDFInfo
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- RU2262339C2 RU2262339C2 RU2000128035/15A RU2000128035A RU2262339C2 RU 2262339 C2 RU2262339 C2 RU 2262339C2 RU 2000128035/15 A RU2000128035/15 A RU 2000128035/15A RU 2000128035 A RU2000128035 A RU 2000128035A RU 2262339 C2 RU2262339 C2 RU 2262339C2
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- acid
- glyoxylamide
- alkyl
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- 239000002246 antineoplastic agent Substances 0.000 title claims abstract description 13
- 230000000259 anti-tumor effect Effects 0.000 title claims abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 76
- -1 N-substituted indole-3-glyoxylamides Chemical class 0.000 claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 239000000725 suspension Substances 0.000 claims abstract description 9
- 239000002775 capsule Substances 0.000 claims abstract description 7
- 239000003826 tablet Substances 0.000 claims abstract description 6
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 5
- 239000003814 drug Substances 0.000 claims abstract description 5
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 3
- 239000006071 cream Substances 0.000 claims abstract description 3
- 239000002674 ointment Substances 0.000 claims abstract description 3
- 239000000829 suppository Substances 0.000 claims abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- PXZNKAFWRZAUAS-UHFFFAOYSA-N 2-[1-[(4-fluorophenyl)methyl]indol-3-yl]-2-oxo-n-pyridin-4-ylacetamide Chemical compound C1=CC(F)=CC=C1CN1C2=CC=CC=C2C(C(=O)C(=O)NC=2C=CN=CC=2)=C1 PXZNKAFWRZAUAS-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 125000003277 amino group Chemical group 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
- 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
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000008298 dragée Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 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
- 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
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 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
- 125000001424 substituent group Chemical group 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
- 229940079593 drug Drugs 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000005862 (C1-C6)alkanoyl 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
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 125000006294 amino alkylene group Chemical group 0.000 claims description 2
- 125000003435 aroyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 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
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000003978 infusion fluid Substances 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
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 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
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 239000001384 succinic acid Substances 0.000 claims description 2
- AMANDCZTVNQSNB-UHFFFAOYSA-N glyoxamide Chemical compound NC(=O)C=O AMANDCZTVNQSNB-UHFFFAOYSA-N 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
- UYUXSRADSPPKRZ-SKNVOMKLSA-N D-glucurono-6,3-lactone Chemical compound O=C[C@H](O)[C@H]1OC(=O)[C@@H](O)[C@H]1O UYUXSRADSPPKRZ-SKNVOMKLSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 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 26
- SOLIIYNRSAWTSQ-UHFFFAOYSA-N 2-[1-[(4-chlorophenyl)methyl]indol-3-yl]-2-oxo-n-pyridin-4-ylacetamide Chemical compound C1=CC(Cl)=CC=C1CN1C2=CC=CC=C2C(C(=O)C(=O)NC=2C=CN=CC=2)=C1 SOLIIYNRSAWTSQ-UHFFFAOYSA-N 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
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- 239000011541 reaction mixture Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
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- 210000004027 cell Anatomy 0.000 description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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- 125000004475 heteroaralkyl group Chemical group 0.000 description 4
- 238000000034 method Methods 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
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D403/12—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 linked by a chain containing hetero atoms as chain links
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19814838.0 | 1998-04-02 | ||
| DE19814838A DE19814838C2 (de) | 1998-04-02 | 1998-04-02 | Indolyl-3-glyoxylsäure-Derivate mit Antitumorwirkung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2000128035A RU2000128035A (ru) | 2002-09-20 |
| RU2262339C2 true RU2262339C2 (ru) | 2005-10-20 |
Family
ID=7863398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2000128035/15A RU2262339C2 (ru) | 1998-04-02 | 1999-03-22 | Производные индолил-3-глиоксиловой кислоты - соединения, обладающие противоопухолевой активностью, фармацевтическая композиция, противоопухолевое средство (варианты) |
Country Status (32)
| Country | Link |
|---|---|
| US (4) | US6232327B1 (https=) |
| EP (1) | EP1071420B1 (https=) |
| JP (2) | JP5253696B2 (https=) |
| KR (1) | KR100583545B1 (https=) |
| CN (1) | CN1148183C (https=) |
| AR (1) | AR018175A1 (https=) |
| AT (1) | ATE304352T1 (https=) |
| AU (1) | AU768510B2 (https=) |
| BG (1) | BG64838B1 (https=) |
| BR (1) | BR9909902A (https=) |
| CA (1) | CA2326833C (https=) |
| DE (2) | DE19814838C2 (https=) |
| DK (1) | DK1071420T3 (https=) |
| EE (1) | EE04354B1 (https=) |
| ES (1) | ES2249884T3 (https=) |
| GE (1) | GEP20032967B (https=) |
| HR (1) | HRP20000643A2 (https=) |
| HU (1) | HUP0101530A3 (https=) |
| ID (1) | ID26504A (https=) |
| IL (2) | IL138737A0 (https=) |
| IS (1) | IS2307B (https=) |
| NO (1) | NO327721B1 (https=) |
| NZ (1) | NZ507084A (https=) |
| PL (1) | PL192779B1 (https=) |
| RS (1) | RS49866B (https=) |
| RU (1) | RU2262339C2 (https=) |
| SK (1) | SK286393B6 (https=) |
| TR (1) | TR200002853T2 (https=) |
| TW (1) | TWI230608B (https=) |
| UA (1) | UA70942C2 (https=) |
| WO (1) | WO1999051224A1 (https=) |
| ZA (1) | ZA200006150B (https=) |
Families Citing this family (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19946301A1 (de) * | 1998-04-02 | 2001-04-19 | Asta Medica Ag | Indolyl-3-glyoxylsäure-Derivate mit therapeutisch wertvollen Eigenschaften |
| DE19814838C2 (de) | 1998-04-02 | 2001-01-18 | Asta Medica Ag | Indolyl-3-glyoxylsäure-Derivate mit Antitumorwirkung |
| WO2000067802A1 (en) * | 1999-05-10 | 2000-11-16 | Protarga, Inc. | Fatty acid-n-substituted indol-3-glyoxyl-amide compositions and uses thereof |
| US6849656B1 (en) * | 1999-09-17 | 2005-02-01 | Baylor University | Indole-containing and combretastatin-related anti-mitotic and anti-tubulin polymerization agents |
| EP1214298B1 (en) * | 1999-09-17 | 2012-05-30 | Baylor University | Indole-containing and combretastatin-related anti-mitotic and anti-tubulin polymerization agents |
| TWI269654B (en) * | 1999-09-28 | 2007-01-01 | Baxter Healthcare Sa | N-substituted indole-3-glyoxylamide compounds having anti-tumor action |
| EP1748046A3 (en) * | 1999-11-23 | 2007-08-22 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| GB9928696D0 (en) | 1999-12-03 | 2000-02-02 | Swan Thomas & Co Ltd | Optical devices and methods of manufacture thereof |
| IT1315267B1 (it) * | 1999-12-23 | 2003-02-03 | Novuspharma Spa | Derivati di 2-(1h-indol-3-il)-2-oxo-acetammidi ad attivita'antitumorale |
| DE19962300A1 (de) * | 1999-12-23 | 2001-06-28 | Asta Medica Ag | Substituierte N-Benzyl-Indol-3-yl-glyoxylsäure-Derivate mit Antitumorwirkung |
| IT1318641B1 (it) * | 2000-07-25 | 2003-08-27 | Novuspharma Spa | Ammidi di acidi 2-(1h-indol-3-il)-2-oxo-acetici ad attivita'antitumorale. |
| DE10037310A1 (de) * | 2000-07-28 | 2002-02-07 | Asta Medica Ag | Neue Indolderivate und deren Verwendung als Arzneimittel |
| CA2460347A1 (en) | 2001-09-13 | 2003-03-20 | Synta Pharmaceuticals Corp. | 3-glyoxlylamideindoles for treating cancer |
| TWI323658B (en) | 2001-12-06 | 2010-04-21 | Nat Health Research Institutes | Novel compounds of indol-3-yl-2-oxyacetylamide derivatives, pharmaceutical composition thereof, and method for manufacturing the same |
| US7109227B2 (en) | 2002-08-26 | 2006-09-19 | National Health Research Institutes | Imidazolamino compounds |
| CA2509222A1 (en) * | 2002-12-10 | 2004-06-24 | Wyeth | Substituted indole oxo-acetyl amino acetic acid derivatives as inhibitors of plasminogen activator inhibitor-1 (pai-1) |
| DE10318609A1 (de) * | 2003-04-24 | 2004-11-11 | Elbion Ag | 5-Hydroxyindole mit N-Oxidgruppen und deren Verwendung als Therapeutika |
| DE10318611A1 (de) | 2003-04-24 | 2004-11-11 | Elbion Ag | 4-, 6- oder 7-Hydroxyindole mit N-Oxidgruppen und deren Verwendung als Therapeutika |
| US7205299B2 (en) * | 2003-06-05 | 2007-04-17 | Zentaris Gmbh | Indole derivatives having an apoptosis-inducing effect |
| EP1484329A1 (de) * | 2003-06-06 | 2004-12-08 | Zentaris GmbH | Indolderivate mit Apoptose induzierender Wirkung |
| EP1641777A1 (de) * | 2003-06-05 | 2006-04-05 | Zentaris GmbH | Indolderivate mit apoptose induzierender wirkung |
| US20050075364A1 (en) * | 2003-07-01 | 2005-04-07 | Kap-Sun Yeung | Indole, azaindole and related heterocyclic N-substituted piperazine derivatives |
| US7211588B2 (en) * | 2003-07-25 | 2007-05-01 | Zentaris Gmbh | N-substituted indolyl-3-glyoxylamides, their use as medicaments and process for their preparation |
| WO2005023761A2 (en) | 2003-09-11 | 2005-03-17 | Kemia, Inc. | Cytokine inhibitors |
| US20050124623A1 (en) | 2003-11-26 | 2005-06-09 | Bender John A. | Diazaindole-dicarbonyl-piperazinyl antiviral agents |
| 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 |
| WO2006002887A1 (en) * | 2004-06-29 | 2006-01-12 | Baxter International Inc. | Aqueous drink solution of indibulin (d-24851) and an organic acid |
| ES2424255T3 (es) * | 2004-11-08 | 2013-09-30 | Baxter International Inc. | Composiciones particuladas de inhibidores de tubulina |
| US20060100209A1 (en) * | 2004-11-09 | 2006-05-11 | Chong-Hui Gu | Formulations 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 |
| 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 |
| CA2605214C (en) | 2004-12-31 | 2016-07-12 | Reddy Us Therapeutics, Inc. | Benzylamine derivatives as cetp inhibitors |
| US8604055B2 (en) | 2004-12-31 | 2013-12-10 | Dr. Reddy's Laboratories Ltd. | Substituted benzylamino quinolines as cholesterol ester-transfer protein inhibitors |
| EP2363128B1 (en) * | 2005-03-11 | 2016-02-17 | Vertex Pharmaceuticals Incorporated | Indole modulators of ATP-binding cassette transporters |
| US20060280787A1 (en) * | 2005-06-14 | 2006-12-14 | Baxter International Inc. | Pharmaceutical formulation of the tubulin inhibitor indibulin for oral administration with improved pharmacokinetic properties, and process for the manufacture thereof |
| US7598380B2 (en) * | 2005-08-03 | 2009-10-06 | Bristol-Myers Squibb Company | Method of preparation of azaindole derivatives |
| AU2006302371A1 (en) * | 2005-10-06 | 2007-04-19 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding cassette transporters |
| 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 |
| SG176477A1 (en) * | 2006-08-07 | 2011-12-29 | Ironwood Pharmaceuticals Inc | Indole compounds |
| CA2670778A1 (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 |
| EP1964835A1 (en) * | 2007-02-28 | 2008-09-03 | Centre National de la Recherche Scientifique | Derivatives of psammaplin A, a method for their synthesis and their use for the prevention or treatment of cancer |
| CN101085779A (zh) * | 2007-07-11 | 2007-12-12 | 中国人民武装警察部队医学院 | 取代吲哚－3－基草酰表鬼臼毒素衍生物及其盐及其用途 |
| GB0715103D0 (en) * | 2007-08-03 | 2007-09-12 | Lectus Therapeutics Ltd | Calcium ion channel modulators and uses thereof |
| GB0909441D0 (en) * | 2009-06-02 | 2009-07-15 | Univ Sheffield | Novel indole derivatives |
| US9585810B2 (en) | 2010-10-14 | 2017-03-07 | Fresenius Medical Care Holdings, Inc. | Systems and methods for delivery of peritoneal dialysis (PD) solutions with integrated inter-chamber diffuser |
| AR084433A1 (es) | 2010-12-22 | 2013-05-15 | Ironwood Pharmaceuticals Inc | Inhibidores de la faah y composiciones farmaceuticas que los contienen |
| HUE044867T2 (hu) | 2011-05-12 | 2019-11-28 | Proteostasis Therapeutics Inc | Proteosztázis szabályzók |
| EP2744803A2 (en) | 2011-08-18 | 2014-06-25 | Dr. Reddy's Laboratories Ltd. | Substituted heterocyclic amine compounds as cholestryl ester-transfer protein (cetp) inhibitors |
| MX352074B (es) | 2011-09-27 | 2017-11-08 | Dr Reddys Laboratories Ltd | Derivados de 5-bencilaminometil-6-aminopirazolo [3,4-b] piridina como inhibidores de proteina de transferencia de ester de colesterilo (cetp) utiles para el tratamiento de aterosclerosis. |
| CN102942516B (zh) * | 2012-11-05 | 2015-02-25 | 宁波大学 | 一种生物碱类化合物及其制备方法和应用 |
| WO2014089177A2 (en) | 2012-12-04 | 2014-06-12 | Massachusetts Institute Of Technology | Compounds, conjugates and compositions of epipolythiodiketopiperazines and polythiodiketopiperazines |
| EP2972394A4 (en) | 2013-03-15 | 2016-11-02 | Sloan Kettering Inst Cancer | HSP90-DESIGNING AND THERAPY |
| IL225540A (en) * | 2013-04-02 | 2015-09-24 | Igal Nir | A method, system, and software for automatically generating a speech database for speech recognition |
| WO2015073528A1 (en) | 2013-11-12 | 2015-05-21 | Proteostasis Therapeutics, Inc. | Proteasome activity enhancing compounds |
| CN105198788A (zh) * | 2015-09-30 | 2015-12-30 | 蒋军荣 | 一种吲哚氧代乙酰(n-二芳甲基)哌嗪衍生物及其制备方法和应用 |
| WO2017197045A1 (en) | 2016-05-11 | 2017-11-16 | Movassaghi Mohammad | Convergent and enantioselective total synthesis of communesin analogs |
| US11932650B2 (en) | 2017-05-11 | 2024-03-19 | Massachusetts Institute Of Technology | Potent agelastatin derivatives as modulators for cancer invasion and metastasis |
| 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 (en) | 2021-02-24 | 2022-09-01 | Massachusetts Institute Of Technology | Himastatin derivatives, and processes of preparation thereof, and uses thereof |
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| WO1998009946A1 (de) * | 1996-09-06 | 1998-03-12 | Asta Medica Aktiengesellschaft | N-substituierte indol-3-glyoxylamide mit antiasthmatischer, antiallergischer und immunsuppressiver/immunmodulierender wirkung |
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| GB1028812A (en) * | 1962-08-28 | 1966-05-11 | Ici Ltd | Indole derivatives |
| GB1089071A (en) * | 1964-02-28 | 1967-11-01 | Merck & Co Inc | Indole derivatives |
| FR2182915A1 (en) * | 1972-03-30 | 1973-12-14 | Nelson Res & Dev | Substd indoles, benzimidazoles - as anti-immune agents , antitumour agents, serotonin inhibitors, hypnotics |
| WO1994008581A1 (fr) * | 1992-10-20 | 1994-04-28 | Toray Industries, Inc. | Inhibiteur d'infiltration d'eosinophiles |
| US5405864A (en) * | 1993-10-15 | 1995-04-11 | Syntex (U.S.A.) Inc. | Chemotherapeutic maleimides |
| PL180523B1 (pl) * | 1994-04-01 | 2001-02-28 | Eli Lilly & Co | Nowy zwiazek, pochodna 1H-indolo-3-glioksylamidu i srodek farmaceutyczny PL PL PL PL PL PL PL PL PL PL |
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| US6262044B1 (en) * | 1998-03-12 | 2001-07-17 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (PTPASES) |
| DE19946301A1 (de) * | 1998-04-02 | 2001-04-19 | Asta Medica Ag | Indolyl-3-glyoxylsäure-Derivate mit therapeutisch wertvollen Eigenschaften |
| DE19814838C2 (de) * | 1998-04-02 | 2001-01-18 | Asta Medica Ag | Indolyl-3-glyoxylsäure-Derivate mit Antitumorwirkung |
| PL198983B1 (pl) * | 1998-04-28 | 2008-08-29 | Elbion Ag | Nowe hydroksyindole, ich zastosowanie jako inhibitorów fosfodiesterazy 4 oraz sposoby ich wytwarzania |
| JP2000239252A (ja) | 1999-02-16 | 2000-09-05 | Mitsubishi Chemicals Corp | インドール誘導体 |
| WO2000067802A1 (en) | 1999-05-10 | 2000-11-16 | Protarga, Inc. | Fatty acid-n-substituted indol-3-glyoxyl-amide compositions and uses thereof |
| DE19962300A1 (de) * | 1999-12-23 | 2001-06-28 | Asta Medica Ag | Substituierte N-Benzyl-Indol-3-yl-glyoxylsäure-Derivate mit Antitumorwirkung |
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| 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 |
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-
1998
- 1998-04-02 DE DE19814838A patent/DE19814838C2/de not_active Expired - Fee Related
-
1999
- 1999-03-22 WO PCT/EP1999/001918 patent/WO1999051224A1/de not_active Ceased
- 1999-03-22 PL PL343525A patent/PL192779B1/pl unknown
- 1999-03-22 ID IDW20001988A patent/ID26504A/id unknown
- 1999-03-22 DE DE59912562T patent/DE59912562D1/de not_active Expired - Lifetime
- 1999-03-22 CN CNB998059234A patent/CN1148183C/zh not_active Expired - Fee Related
- 1999-03-22 NZ NZ507084A patent/NZ507084A/en not_active IP Right Cessation
- 1999-03-22 SK SK1430-2000A patent/SK286393B6/sk not_active IP Right Cessation
- 1999-03-22 JP JP2000541995A patent/JP5253696B2/ja not_active Expired - Fee Related
- 1999-03-22 EE EEP200000581A patent/EE04354B1/xx not_active IP Right Cessation
- 1999-03-22 UA UA2000116192A patent/UA70942C2/uk unknown
- 1999-03-22 BR BR9909902-0A patent/BR9909902A/pt not_active IP Right Cessation
- 1999-03-22 KR KR1020007010934A patent/KR100583545B1/ko not_active Expired - Fee Related
- 1999-03-22 ES ES99910372T patent/ES2249884T3/es not_active Expired - Lifetime
- 1999-03-22 RS YUP-593/00A patent/RS49866B/sr unknown
- 1999-03-22 HR HR20000643A patent/HRP20000643A2/hr not_active Application Discontinuation
- 1999-03-22 RU RU2000128035/15A patent/RU2262339C2/ru not_active IP Right Cessation
- 1999-03-22 AT AT99910372T patent/ATE304352T1/de active
- 1999-03-22 DK DK99910372T patent/DK1071420T3/da active
- 1999-03-22 AU AU29349/99A patent/AU768510B2/en not_active Ceased
- 1999-03-22 HU HU0101530A patent/HUP0101530A3/hu unknown
- 1999-03-22 IL IL13873799A patent/IL138737A0/xx active IP Right Grant
- 1999-03-22 GE GEAP19995611A patent/GEP20032967B/en unknown
- 1999-03-22 EP EP99910372A patent/EP1071420B1/de not_active Expired - Lifetime
- 1999-03-22 CA CA002326833A patent/CA2326833C/en not_active Expired - Fee Related
- 1999-03-22 TR TR2000/02853T patent/TR200002853T2/xx unknown
- 1999-03-23 TW TW088104599A patent/TWI230608B/zh not_active IP Right Cessation
- 1999-03-31 AR ARP990101501A patent/AR018175A1/es unknown
- 1999-04-02 US US09/285,058 patent/US6232327B1/en not_active Expired - Lifetime
-
2000
- 2000-09-22 IS IS5635A patent/IS2307B/is unknown
- 2000-09-27 IL IL138737A patent/IL138737A/en not_active IP Right Cessation
- 2000-09-29 NO NO20004916A patent/NO327721B1/no not_active IP Right Cessation
- 2000-10-12 BG BG104849A patent/BG64838B1/bg unknown
- 2000-10-31 ZA ZA200006150A patent/ZA200006150B/en unknown
-
2001
- 2001-03-19 US US09/810,604 patent/US20030023093A1/en not_active Abandoned
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2002
- 2002-12-04 US US10/309,204 patent/US7579365B2/en not_active Expired - Fee Related
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2007
- 2007-08-20 US US11/894,591 patent/US20080027110A1/en not_active Abandoned
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2011
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