JP2004537598A5 - - Google Patents
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- JP2004537598A5 JP2004537598A5 JP2003519052A JP2003519052A JP2004537598A5 JP 2004537598 A5 JP2004537598 A5 JP 2004537598A5 JP 2003519052 A JP2003519052 A JP 2003519052A JP 2003519052 A JP2003519052 A JP 2003519052A JP 2004537598 A5 JP2004537598 A5 JP 2004537598A5
- Authority
- JP
- Japan
- Prior art keywords
- och
- alkyl
- formula
- chc
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 44
- 239000002253 acid Substances 0.000 claims 16
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 14
- 101150065749 Churc1 gene Proteins 0.000 claims 14
- 102100038239 Protein Churchill Human genes 0.000 claims 14
- -1 1-isopropyl Chemical group 0.000 claims 5
- 238000000034 method Methods 0.000 claims 4
- 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- OQQXGCLLMDQESN-UHFFFAOYSA-N cyclohexylcarbamic acid Chemical compound OC(=O)NC1CCCCC1 OQQXGCLLMDQESN-UHFFFAOYSA-N 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- GHXZPUGJZVBLGC-UHFFFAOYSA-N iodoethene Chemical compound IC=C GHXZPUGJZVBLGC-UHFFFAOYSA-N 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 238000006400 oxidative hydrolysis reaction Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 0 CC(C)C(C(C)C(*)C(C)CC=CC(C)C(*)[C@@](C)C=CCCc1ccccc1)OC(N)=O Chemical compound CC(C)C(C(C)C(*)C(C)CC=CC(C)C(*)[C@@](C)C=CCCc1ccccc1)OC(N)=O 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229930001119 polyketide Natural products 0.000 description 2
- 150000003881 polyketide derivatives Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- RSKRBPAWAPOJKO-DAMUDMPHSA-N CC(C/C(/C)=C\C(C)C(C(C)/C=C\C(Cc1ccccc1)=O)O)C(C(C)C(C(C)/C=C\C=C)OC(N)=O)O Chemical compound CC(C/C(/C)=C\C(C)C(C(C)/C=C\C(Cc1ccccc1)=O)O)C(C(C)C(C(C)/C=C\C=C)OC(N)=O)O RSKRBPAWAPOJKO-DAMUDMPHSA-N 0.000 description 1
- OGAXODFPSAOVSK-KQPCLCFSSA-N CC(C/C(/C)=C\C(C)C(C(C)/C=C\C(Cc1ccccn1)=O)O)C(C(C)C(C(C)/C=C\C=C)OC(N)=O)O Chemical compound CC(C/C(/C)=C\C(C)C(C(C)/C=C\C(Cc1ccccn1)=O)O)C(C(C)C(C(C)/C=C\C=C)OC(N)=O)O OGAXODFPSAOVSK-KQPCLCFSSA-N 0.000 description 1
- UMDSYFREFUYICD-AJIDPHOHSA-N CC(C/C(/C)=C\C(C)C(C(C)/C=C\CO)O)C(C(C)C(C(C)/C=C\C=C)OC(N)=O)O Chemical compound CC(C/C(/C)=C\C(C)C(C(C)/C=C\CO)O)C(C(C)C(C(C)/C=C\C=C)OC(N)=O)O UMDSYFREFUYICD-AJIDPHOHSA-N 0.000 description 1
- YRBWQWMUTLMFOM-FJMIUWCCSA-N CCC(/C=C\C(C)C(C(C)/C=C(/C)\CC(C)C(C(C)C(C(C)/C=C\C=C)OC(N)=O)O)N=O)O Chemical compound CCC(/C=C\C(C)C(C(C)/C=C(/C)\CC(C)C(C(C)C(C(C)/C=C\C=C)OC(N)=O)O)N=O)O YRBWQWMUTLMFOM-FJMIUWCCSA-N 0.000 description 1
- ANCBHUWOSRUAIQ-YJRRHQFJSA-N CCCCC(C)C(C(C)C(C(C)C/C(/C)=C\C(C)C(C(C)/C=C\C(Cc1ccccc1)=O)O)O)O Chemical compound CCCCC(C)C(C(C)C(C(C)C/C(/C)=C\C(C)C(C(C)/C=C\C(Cc1ccccc1)=O)O)O)O ANCBHUWOSRUAIQ-YJRRHQFJSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- ZDQWVKDDJDIVAL-UHFFFAOYSA-N catecholborane Chemical compound C1=CC=C2O[B]OC2=C1 ZDQWVKDDJDIVAL-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- IPJKJLXEVHOKSE-UHFFFAOYSA-L manganese dihydroxide Chemical compound [OH-].[OH-].[Mn+2] IPJKJLXEVHOKSE-UHFFFAOYSA-L 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910001868 water Inorganic materials 0.000 description 1
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31030701P | 2001-08-06 | 2001-08-06 | |
| US34453201P | 2001-10-25 | 2001-10-25 | |
| US34118901P | 2001-12-13 | 2001-12-13 | |
| US34904702P | 2002-01-16 | 2002-01-16 | |
| US35899702P | 2002-02-22 | 2002-02-22 | |
| PCT/EP2002/008734 WO2003014102A1 (en) | 2001-08-06 | 2002-08-05 | Certain substituted polyketides, pharmaceutical compositions containing them and their use in treating tumors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004537598A JP2004537598A (ja) | 2004-12-16 |
| JP2004537598A5 true JP2004537598A5 (enExample) | 2006-01-05 |
| JP4243183B2 JP4243183B2 (ja) | 2009-03-25 |
Family
ID=27540954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003519052A Expired - Fee Related JP4243183B2 (ja) | 2001-08-06 | 2002-08-05 | 一定の置換ポリケチド、それらを含む医薬組成物および腫瘍処置におけるそれらの使用 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US6972292B2 (enExample) |
| EP (1) | EP1417195A1 (enExample) |
| JP (1) | JP4243183B2 (enExample) |
| CN (1) | CN100522956C (enExample) |
| BR (1) | BR0211762A (enExample) |
| CA (1) | CA2454081A1 (enExample) |
| WO (1) | WO2003014102A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005084349A2 (en) * | 2004-03-02 | 2005-09-15 | Kosan Biosciences, Inc. | Compounds useful for the synthesis of (+)-discodermolide and methods therefor |
| US7214708B2 (en) * | 2004-11-18 | 2007-05-08 | Kosan Biosciences Incorporated | Synthetic discodermolide analogs |
| CN112424255A (zh) * | 2018-07-17 | 2021-02-26 | 引能仕株式会社 | 反应性稀释剂、组合物、密封材、固化物、基板、电子部件、环氧化合物、及化合物的制造方法 |
| CN113527238B (zh) * | 2021-08-02 | 2022-12-13 | 昆明学院 | 一种海绵内生真菌来源的聚酮化合物及其在制备抗炎药物中的应用 |
| CN119462593A (zh) * | 2024-10-11 | 2025-02-18 | 暨南大学 | 多环聚酮类化合物和其制备方法、药物组合物及应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4939168A (en) * | 1989-08-11 | 1990-07-03 | Harbor Branch Oceanographics Institution, Inc. | Discodermolide compounds, compositions containing same and methods of preparation and use |
| US5789605A (en) | 1996-12-03 | 1998-08-04 | Trustees Of The University Of Pennsylvania | Synthetic techniques and intermediates for polyhydroxy, dienyl lactones and mimics thereof |
| US6870058B2 (en) | 1996-12-03 | 2005-03-22 | The Trustees Of The University Of Pennsylvania | Compounds which mimic the chemical and biological properties of discodermolide |
| US6242616B1 (en) * | 1996-12-03 | 2001-06-05 | The Trustees Of The University Of Pennsylvania | Synthetic techniques and intermediates for polyhydroxy, dienyl lactone derivatives |
| US6096904A (en) | 1996-12-03 | 2000-08-01 | The Trustees Of The University Of Pennsylvania | Synthetic techniques and intermediates for polyhydroxy, dienyl lactone derivatives |
| US6127406A (en) | 1998-10-09 | 2000-10-03 | Harbor Branch Oceanographic Institution, Inc. | Discodermolide compounds and methods of use |
-
2002
- 2002-08-05 EP EP02794555A patent/EP1417195A1/en not_active Withdrawn
- 2002-08-05 US US10/212,535 patent/US6972292B2/en not_active Expired - Fee Related
- 2002-08-05 CN CNB028154991A patent/CN100522956C/zh not_active Expired - Fee Related
- 2002-08-05 JP JP2003519052A patent/JP4243183B2/ja not_active Expired - Fee Related
- 2002-08-05 CA CA002454081A patent/CA2454081A1/en not_active Abandoned
- 2002-08-05 WO PCT/EP2002/008734 patent/WO2003014102A1/en not_active Ceased
- 2002-08-05 BR BR0211762-2A patent/BR0211762A/pt not_active IP Right Cessation
-
2004
- 2004-09-28 US US10/951,857 patent/US7192980B2/en not_active Expired - Fee Related
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