DE60205265T2 - 1-glyoxylamidindolizine zur behandlung von krebs - Google Patents
1-glyoxylamidindolizine zur behandlung von krebs Download PDFInfo
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- DE60205265T2 DE60205265T2 DE60205265T DE60205265T DE60205265T2 DE 60205265 T2 DE60205265 T2 DE 60205265T2 DE 60205265 T DE60205265 T DE 60205265T DE 60205265 T DE60205265 T DE 60205265T DE 60205265 T2 DE60205265 T2 DE 60205265T2
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- Prior art keywords
- substituted
- unsubstituted
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- compound
- alkyl
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- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
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- 230000002349 favourable effect Effects 0.000 description 1
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- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
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- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
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- 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 239000007788 liquid Substances 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
- 210000000032 mammalian fat body Anatomy 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
- 125000005341 metaphosphate group Chemical group 0.000 description 1
- 230000009401 metastasis Effects 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
- DBNQIOANXZVWIP-UHFFFAOYSA-N n,n-dimethyl-1,1-bis[(2-methylpropan-2-yl)oxy]methanamine Chemical compound CC(C)(C)OC(N(C)C)OC(C)(C)C DBNQIOANXZVWIP-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
- 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
- 150000007530 organic bases Chemical class 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 Substances 0.000 description 1
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 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
- 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
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 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
- 239000000376 reactant Substances 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
- 230000000630 rising effect Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 239000000523 sample 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
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
- 241000894007 species Species 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
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 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 Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 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
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 210000001694 thigh bone Anatomy 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
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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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32202001P | 2001-09-13 | 2001-09-13 | |
| US322020P | 2001-09-13 | ||
| PCT/US2002/029154 WO2003022846A1 (en) | 2001-09-13 | 2002-09-13 | 1-glyoxlylamide indolizines for treating cancer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60205265D1 DE60205265D1 (de) | 2005-09-01 |
| DE60205265T2 true DE60205265T2 (de) | 2006-03-30 |
Family
ID=23253054
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60205265T Expired - Fee Related DE60205265T2 (de) | 2001-09-13 | 2002-09-13 | 1-glyoxylamidindolizine zur behandlung von krebs |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US6861436B2 (enExample) |
| EP (1) | EP1432709B8 (enExample) |
| JP (1) | JP2005504795A (enExample) |
| KR (1) | KR20040053125A (enExample) |
| CN (1) | CN1568324A (enExample) |
| AT (1) | ATE300542T1 (enExample) |
| AU (1) | AU2002333626B2 (enExample) |
| BR (1) | BR0212794A (enExample) |
| CA (1) | CA2459886A1 (enExample) |
| DE (1) | DE60205265T2 (enExample) |
| ES (1) | ES2245747T3 (enExample) |
| IL (1) | IL160810A0 (enExample) |
| IS (1) | IS7176A (enExample) |
| MX (1) | MXPA04002323A (enExample) |
| NO (1) | NO20041035L (enExample) |
| NZ (1) | NZ531700A (enExample) |
| PT (1) | PT1432709E (enExample) |
| WO (1) | WO2003022846A1 (enExample) |
| ZA (1) | ZA200401996B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040116462A1 (en) * | 2002-12-12 | 2004-06-17 | Mitsunori Ono | Indolizine compounds |
| PT1432709E (pt) * | 2001-09-13 | 2005-10-31 | Synta Pharmaceuticals Corp | Indolizinas de 1-glioxilamida para o trtamento do cancro |
| JP2006504692A (ja) * | 2002-09-13 | 2006-02-09 | シンタ ファーマシューティカルズ コーポレーション | インドリジンの合成方法 |
| 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 |
| US20070293456A9 (en) * | 2004-12-30 | 2007-12-20 | Anthony Hayford | Method for the synthesis of 3-substituted indolizine and benzoindolizine compounds |
| WO2006128184A2 (en) * | 2005-05-20 | 2006-11-30 | Alantos-Pharmaceuticals, Inc. | Pyrimidine or triazine fused bicyclic metalloprotease inhibitors |
| US20070155738A1 (en) | 2005-05-20 | 2007-07-05 | Alantos Pharmaceuticals, Inc. | Heterobicyclic metalloprotease inhibitors |
| CA2733247C (en) * | 2008-08-14 | 2018-04-03 | Beta Pharma Canada Inc. | Heterocyclic amide derivatives as ep4 receptor antagonists |
| EP4008327A1 (en) | 2009-04-29 | 2022-06-08 | Amarin Pharmaceuticals Ireland Limited | Pharmaceutical compositions comprising epa and a cardiovascular agent and methods of using the same |
| 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 |
| US6472389B1 (en) | 1998-05-21 | 2002-10-29 | Shionogi & Co., Ltd. | Pyrrolo[1,2-b] pyridazine derivatives having sPLA2 inhibitory effect |
| 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 |
| PT1432709E (pt) * | 2001-09-13 | 2005-10-31 | Synta Pharmaceuticals Corp | Indolizinas de 1-glioxilamida para o trtamento do cancro |
| US20040116462A1 (en) * | 2002-12-12 | 2004-06-17 | Mitsunori Ono | Indolizine compounds |
-
2002
- 2002-09-13 PT PT02798231T patent/PT1432709E/pt unknown
- 2002-09-13 ES ES02798231T patent/ES2245747T3/es not_active Expired - Lifetime
- 2002-09-13 AU AU2002333626A patent/AU2002333626B2/en not_active Ceased
- 2002-09-13 US US10/244,088 patent/US6861436B2/en not_active Expired - Fee Related
- 2002-09-13 WO PCT/US2002/029154 patent/WO2003022846A1/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 BR BR0212794-6A patent/BR0212794A/pt not_active IP Right Cessation
- 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 AT AT02798231T patent/ATE300542T1/de not_active IP Right Cessation
- 2002-09-13 IL IL16081002A patent/IL160810A0/xx unknown
- 2002-09-13 MX MXPA04002323A patent/MXPA04002323A/es unknown
- 2002-09-13 JP JP2003526921A patent/JP2005504795A/ja active Pending
- 2002-09-13 NZ NZ531700A patent/NZ531700A/en unknown
- 2002-09-13 CA CA002459886A patent/CA2459886A1/en not_active Abandoned
-
2004
- 2004-03-11 IS IS7176A patent/IS7176A/is unknown
- 2004-03-11 ZA ZA200401996A patent/ZA200401996B/xx unknown
- 2004-03-11 NO NO20041035A patent/NO20041035L/no not_active Application Discontinuation
- 2004-05-20 US US10/849,978 patent/US20040214850A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| IL160810A0 (en) | 2004-08-31 |
| CA2459886A1 (en) | 2003-03-20 |
| NO20041035L (no) | 2004-04-30 |
| AU2002333626B2 (en) | 2006-06-29 |
| KR20040053125A (ko) | 2004-06-23 |
| ZA200401996B (en) | 2005-05-31 |
| MXPA04002323A (es) | 2005-04-08 |
| EP1432709B1 (en) | 2005-07-27 |
| EP1432709A1 (en) | 2004-06-30 |
| US6861436B2 (en) | 2005-03-01 |
| JP2005504795A (ja) | 2005-02-17 |
| EP1432709B8 (en) | 2005-11-02 |
| IS7176A (is) | 2004-03-11 |
| ES2245747T3 (es) | 2006-01-16 |
| WO2003022846A1 (en) | 2003-03-20 |
| HK1063322A1 (en) | 2004-12-24 |
| DE60205265D1 (de) | 2005-09-01 |
| PT1432709E (pt) | 2005-10-31 |
| BR0212794A (pt) | 2004-10-05 |
| CN1568324A (zh) | 2005-01-19 |
| ATE300542T1 (de) | 2005-08-15 |
| US20030153759A1 (en) | 2003-08-14 |
| NZ531700A (en) | 2006-10-27 |
| US20040214850A1 (en) | 2004-10-28 |
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