MXPA04002323A - 1-GLIOXILILAMIDA-INDOLIZINAS PARA EL TRATAMIENTO DEL CáNCER. - Google Patents
1-GLIOXILILAMIDA-INDOLIZINAS PARA EL TRATAMIENTO DEL CáNCER.Info
- Publication number
- MXPA04002323A MXPA04002323A MXPA04002323A MXPA04002323A MXPA04002323A MX PA04002323 A MXPA04002323 A MX PA04002323A MX PA04002323 A MXPA04002323 A MX PA04002323A MX PA04002323 A MXPA04002323 A MX PA04002323A MX PA04002323 A MXPA04002323 A MX PA04002323A
- Authority
- MX
- Mexico
- Prior art keywords
- substituted
- group
- unsubstituted
- alkyl
- ring
- Prior art date
Links
- 206010028980 Neoplasm Diseases 0.000 title claims description 59
- 201000011510 cancer Diseases 0.000 title claims description 35
- 150000002478 indolizines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 152
- 125000003118 aryl group Chemical group 0.000 claims abstract description 47
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 45
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 12
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 239000003814 drug Substances 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 229940079593 drug Drugs 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 23
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
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- 229910017711 NHRa Inorganic materials 0.000 claims description 20
- -1 W-morpholino Chemical group 0.000 claims description 20
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
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- 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000002243 precursor Substances 0.000 claims description 7
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- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 150000002829 nitrogen Chemical class 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
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- 241000689227 Cora <basidiomycete fungus> Species 0.000 claims 1
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- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 150000002940 palladium Chemical class 0.000 claims 1
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- 239000008103 glucose Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000004408 hybridoma Anatomy 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000010166 immunofluorescence Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229940060367 inert ingredients Drugs 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000005341 metaphosphate group Chemical group 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- IZYBEMGNIUSSAX-UHFFFAOYSA-N methyl benzenecarboperoxoate Chemical compound COOC(=O)C1=CC=CC=C1 IZYBEMGNIUSSAX-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N methylsulphonylmethane Natural products CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229940127084 other anti-cancer agent Drugs 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 125000005968 oxazolinyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Chemical group 0.000 description 1
- 210000003049 pelvic bone Anatomy 0.000 description 1
- DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 229950009215 phenylbutanoic acid Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-M propynoate Chemical compound [O-]C(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-M 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 239000003104 tissue culture media Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 238000013414 tumor xenograft model Methods 0.000 description 1
- 230000001173 tumoral effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229940071104 xylenesulfonate Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32202001P | 2001-09-13 | 2001-09-13 | |
| PCT/US2002/029154 WO2003022846A1 (en) | 2001-09-13 | 2002-09-13 | 1-glyoxlylamide indolizines for treating cancer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA04002323A true MXPA04002323A (es) | 2005-04-08 |
Family
ID=23253054
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA04002323A MXPA04002323A (es) | 2001-09-13 | 2002-09-13 | 1-GLIOXILILAMIDA-INDOLIZINAS PARA EL TRATAMIENTO DEL CáNCER. |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US6861436B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1432709B8 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2005504795A (cg-RX-API-DMAC7.html) |
| KR (1) | KR20040053125A (cg-RX-API-DMAC7.html) |
| CN (1) | CN1568324A (cg-RX-API-DMAC7.html) |
| AT (1) | ATE300542T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU2002333626B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BR0212794A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2459886A1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE60205265T2 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2245747T3 (cg-RX-API-DMAC7.html) |
| IL (1) | IL160810A0 (cg-RX-API-DMAC7.html) |
| IS (1) | IS7176A (cg-RX-API-DMAC7.html) |
| MX (1) | MXPA04002323A (cg-RX-API-DMAC7.html) |
| NO (1) | NO20041035L (cg-RX-API-DMAC7.html) |
| NZ (1) | NZ531700A (cg-RX-API-DMAC7.html) |
| PT (1) | PT1432709E (cg-RX-API-DMAC7.html) |
| WO (1) | WO2003022846A1 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA200401996B (cg-RX-API-DMAC7.html) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005504795A (ja) * | 2001-09-13 | 2005-02-17 | シンタ ファーマスーティカルズ コーポレイション | 癌処置のための１−グリオキシリルアミドインドリジン類 |
| US20040116462A1 (en) * | 2002-12-12 | 2004-06-17 | Mitsunori Ono | Indolizine compounds |
| CA2496764A1 (en) * | 2002-09-13 | 2004-03-25 | Synta Pharmaceuticals Corp. | Synthesis of indolizines |
| DE10318611A1 (de) | 2003-04-24 | 2004-11-11 | Elbion Ag | 4-, 6- oder 7-Hydroxyindole mit N-Oxidgruppen und deren Verwendung als Therapeutika |
| WO2005099824A1 (en) * | 2004-03-30 | 2005-10-27 | Synta Pharmaceuticals, Corp. | 1-glyoxylamide indolizines for treating lung and ovarian cancer |
| GB0413605D0 (en) | 2004-06-17 | 2004-07-21 | Addex Pharmaceuticals Sa | Novel compounds |
| WO2006073938A2 (en) * | 2004-12-30 | 2006-07-13 | East Carolina University | Method for the synthesis of 3-substituted indolizine and benzoindolizine compounds |
| CA2608890C (en) * | 2005-05-20 | 2011-08-02 | Alantos-Pharmaceuticals, Inc. | Heterobicyclic metalloprotease inhibitors |
| US20070155738A1 (en) | 2005-05-20 | 2007-07-05 | Alantos Pharmaceuticals, Inc. | Heterobicyclic metalloprotease inhibitors |
| US8404736B2 (en) * | 2008-08-14 | 2013-03-26 | Beta Pharma Canada Inc. | Heterocyclic amide derivatives as EP4 receptor antagonists |
| CN102413825A (zh) | 2009-04-29 | 2012-04-11 | 阿马里纳股份公司 | 含有epa和心血管剂的药物组合物以及使用其的方法 |
| AR077428A1 (es) * | 2009-07-29 | 2011-08-24 | Sanofi Aventis | (aza) indolizinacarboxamidas ciclicas su preparacion y su uso como agentes farmaceuticos |
| CN113603694B (zh) * | 2021-07-16 | 2022-07-22 | 浙江工业大学 | 一种1,2-二酮类化合物及其制备方法和应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2287706A (en) | 1994-03-21 | 1995-09-27 | Fujisawa Pharmaceutical Co | Indolizine derivatives |
| FR2757166B1 (fr) * | 1996-12-12 | 1999-01-29 | Rhone Poulenc Rorer Sa | Derives du pyrrole, leur preparation et les compositions pharmaceutiques qui les contiennent |
| WO1998047507A1 (en) | 1997-04-24 | 1998-10-29 | Shionogi & Co., Ltd. | Method for the treatment of stroke using n-heterocyclic glyoxylamide compounds |
| KR20010034881A (ko) | 1998-05-21 | 2001-04-25 | 시오노 요시히코 | ｓＰＬＡ2 억제 효과를 갖는 피롤로[1,2-ｂ]피리다진 유도체 |
| CA2346334A1 (en) | 1998-10-14 | 2000-04-20 | Shionogi & Co., Ltd. | Composition for treating or preventing ischemia reperfusion injury |
| US6461538B2 (en) * | 1999-12-16 | 2002-10-08 | Fuji Photo Film Co., Ltd. | Production process for indolizine compounds and their use in organic light-emitting devices |
| JP2005504795A (ja) * | 2001-09-13 | 2005-02-17 | シンタ ファーマスーティカルズ コーポレイション | 癌処置のための１−グリオキシリルアミドインドリジン類 |
| US20040116462A1 (en) * | 2002-12-12 | 2004-06-17 | Mitsunori Ono | Indolizine compounds |
-
2002
- 2002-09-13 JP JP2003526921A patent/JP2005504795A/ja active Pending
- 2002-09-13 AT AT02798231T patent/ATE300542T1/de not_active IP Right Cessation
- 2002-09-13 BR BR0212794-6A patent/BR0212794A/pt not_active IP Right Cessation
- 2002-09-13 PT PT02798231T patent/PT1432709E/pt unknown
- 2002-09-13 CA CA002459886A patent/CA2459886A1/en not_active Abandoned
- 2002-09-13 WO PCT/US2002/029154 patent/WO2003022846A1/en not_active Ceased
- 2002-09-13 AU AU2002333626A patent/AU2002333626B2/en not_active Ceased
- 2002-09-13 DE DE60205265T patent/DE60205265T2/de not_active Expired - Fee Related
- 2002-09-13 CN CNA028202848A patent/CN1568324A/zh active Pending
- 2002-09-13 KR KR10-2004-7003754A patent/KR20040053125A/ko not_active Withdrawn
- 2002-09-13 EP EP02798231A patent/EP1432709B8/en not_active Expired - Lifetime
- 2002-09-13 US US10/244,088 patent/US6861436B2/en not_active Expired - Fee Related
- 2002-09-13 IL IL16081002A patent/IL160810A0/xx unknown
- 2002-09-13 MX MXPA04002323A patent/MXPA04002323A/es unknown
- 2002-09-13 NZ NZ531700A patent/NZ531700A/en unknown
- 2002-09-13 ES ES02798231T patent/ES2245747T3/es not_active Expired - Lifetime
-
2004
- 2004-03-11 IS IS7176A patent/IS7176A/is unknown
- 2004-03-11 NO NO20041035A patent/NO20041035L/no not_active Application Discontinuation
- 2004-03-11 ZA ZA200401996A patent/ZA200401996B/xx unknown
- 2004-05-20 US US10/849,978 patent/US20040214850A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005504795A (ja) | 2005-02-17 |
| PT1432709E (pt) | 2005-10-31 |
| NZ531700A (en) | 2006-10-27 |
| IS7176A (is) | 2004-03-11 |
| ES2245747T3 (es) | 2006-01-16 |
| CN1568324A (zh) | 2005-01-19 |
| BR0212794A (pt) | 2004-10-05 |
| DE60205265D1 (de) | 2005-09-01 |
| EP1432709A1 (en) | 2004-06-30 |
| NO20041035L (no) | 2004-04-30 |
| ZA200401996B (en) | 2005-05-31 |
| AU2002333626B2 (en) | 2006-06-29 |
| IL160810A0 (en) | 2004-08-31 |
| US6861436B2 (en) | 2005-03-01 |
| CA2459886A1 (en) | 2003-03-20 |
| EP1432709B1 (en) | 2005-07-27 |
| DE60205265T2 (de) | 2006-03-30 |
| KR20040053125A (ko) | 2004-06-23 |
| ATE300542T1 (de) | 2005-08-15 |
| HK1063322A1 (en) | 2004-12-24 |
| EP1432709B8 (en) | 2005-11-02 |
| WO2003022846A1 (en) | 2003-03-20 |
| US20030153759A1 (en) | 2003-08-14 |
| US20040214850A1 (en) | 2004-10-28 |
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