JP2008524327A5 - - Google Patents
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- Publication number
- JP2008524327A5 JP2008524327A5 JP2007548240A JP2007548240A JP2008524327A5 JP 2008524327 A5 JP2008524327 A5 JP 2008524327A5 JP 2007548240 A JP2007548240 A JP 2007548240A JP 2007548240 A JP2007548240 A JP 2007548240A JP 2008524327 A5 JP2008524327 A5 JP 2008524327A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- protecting group
- oxycarbonyl
- amine protecting
- compound
- 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
Links
- 238000000034 method Methods 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 22
- 125000006242 amine protecting group Chemical group 0.000 claims 14
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 14
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 7
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 7
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 7
- VSNKRNNQPLVZNF-UHFFFAOYSA-N 1-chloro-2-diaminophosphoryloxyethane Chemical compound NP(N)(=O)OCCCl VSNKRNNQPLVZNF-UHFFFAOYSA-N 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 5
- 238000010511 deprotection reaction Methods 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 3
- -1 benzenesulfonyloxy Chemical group 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 239000007789 gas Substances 0.000 claims 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 238000010531 catalytic reduction reaction Methods 0.000 claims 1
- ANCLJVISBRWUTR-UHFFFAOYSA-N diaminophosphinic acid Chemical compound NP(N)(O)=O ANCLJVISBRWUTR-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 238000006317 isomerization reaction Methods 0.000 claims 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims 1
- 229940011051 isopropyl acetate Drugs 0.000 claims 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- HJKYXKSLRZKNSI-UHFFFAOYSA-I pentapotassium;hydrogen sulfate;oxido sulfate;sulfuric acid Chemical compound [K+].[K+].[K+].[K+].[K+].OS([O-])(=O)=O.[O-]S([O-])(=O)=O.OS(=O)(=O)O[O-].OS(=O)(=O)O[O-] HJKYXKSLRZKNSI-UHFFFAOYSA-I 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 229920001843 polymethylhydrosiloxane Polymers 0.000 claims 1
- 229910000077 silane Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/018,391 | 2004-12-21 | ||
| US11/018,391 US8198247B2 (en) | 2004-12-21 | 2004-12-21 | Process for and intermediates in the preparation of canfosfamide and its salts |
| PCT/US2005/042693 WO2006068769A1 (en) | 2004-12-21 | 2005-11-23 | Process for and intermediates in the preparation of canfosfamide and its salts, pharmaceutical compositions containing some intermediates, and their use as anticancer agents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008524327A JP2008524327A (ja) | 2008-07-10 |
| JP2008524327A5 true JP2008524327A5 (enExample) | 2008-12-18 |
| JP5060306B2 JP5060306B2 (ja) | 2012-10-31 |
Family
ID=36216909
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007548240A Expired - Fee Related JP5060306B2 (ja) | 2004-12-21 | 2005-11-23 | カンホスファミドおよびその塩の製造方法および製造中間体、中間体を含む医薬組成物ならびに抗ガン剤としてのその使用 |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US8198247B2 (enExample) |
| EP (1) | EP1827605B1 (enExample) |
| JP (1) | JP5060306B2 (enExample) |
| KR (1) | KR20070089795A (enExample) |
| CN (1) | CN101080251B (enExample) |
| AR (1) | AR052167A1 (enExample) |
| AU (1) | AU2005319579B2 (enExample) |
| BR (1) | BRPI0519141A2 (enExample) |
| CA (1) | CA2587088A1 (enExample) |
| EA (1) | EA016052B1 (enExample) |
| IL (1) | IL182835A0 (enExample) |
| MX (1) | MX2007007215A (enExample) |
| TW (1) | TW200633717A (enExample) |
| WO (1) | WO2006068769A1 (enExample) |
| ZA (1) | ZA200704318B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100056825A1 (en) * | 2008-08-28 | 2010-03-04 | Telik, Inc. | Formulations of canfosfamide and their preparation |
| US8324426B2 (en) | 2008-08-28 | 2012-12-04 | Telik, Inc. | Formulations of canfosfamide and their preparation |
| CA2733732A1 (en) * | 2011-02-25 | 2012-08-25 | Telik, Inc. | Formulations of canfosfamide and their preparation |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5556942A (en) | 1991-04-29 | 1996-09-17 | Terrapin Technologies, Inc. | Glutathione S-transferase-activated compounds |
| EP1072608B1 (en) * | 1998-04-16 | 2005-06-15 | Teijin Limited | Glutathione derivatives and dosage forms thereof |
| US6417397B1 (en) * | 1999-10-04 | 2002-07-09 | The Regents Of The University Of California, San Diego | N-substituted alkylamino acids for use as amino-protecting groups |
| UA74574C2 (en) | 2000-05-02 | 2006-01-16 | Telik Inc | Bis (n,n'-bis(2-halogenethyl)amino)phosphodiamates, a method for producing thereof (variants), a pharmaceutical composition containing them, and a method for the treatment of tumors |
| US6506739B1 (en) | 2001-05-01 | 2003-01-14 | Telik, Inc. | Bis-(N,N'-bis-(2-haloethyl)amino)phosphoramidates as antitumor agents |
| WO2006074249A1 (en) * | 2005-01-06 | 2006-07-13 | Telik, Inc. | Tripeptide and tetrapeptide thioethers |
-
2004
- 2004-12-21 US US11/018,391 patent/US8198247B2/en not_active Expired - Fee Related
-
2005
- 2005-11-23 TW TW094141102A patent/TW200633717A/zh unknown
- 2005-11-23 EP EP05852166.7A patent/EP1827605B1/en not_active Expired - Lifetime
- 2005-11-23 CN CN2005800428600A patent/CN101080251B/zh not_active Expired - Fee Related
- 2005-11-23 KR KR1020077012351A patent/KR20070089795A/ko not_active Abandoned
- 2005-11-23 JP JP2007548240A patent/JP5060306B2/ja not_active Expired - Fee Related
- 2005-11-23 EA EA200701180A patent/EA016052B1/ru not_active IP Right Cessation
- 2005-11-23 CA CA002587088A patent/CA2587088A1/en not_active Abandoned
- 2005-11-23 AU AU2005319579A patent/AU2005319579B2/en not_active Ceased
- 2005-11-23 MX MX2007007215A patent/MX2007007215A/es active IP Right Grant
- 2005-11-23 WO PCT/US2005/042693 patent/WO2006068769A1/en not_active Ceased
- 2005-11-23 BR BRPI0519141-6A patent/BRPI0519141A2/pt not_active IP Right Cessation
- 2005-12-15 AR ARP050105289A patent/AR052167A1/es not_active Application Discontinuation
-
2007
- 2007-04-26 IL IL182835A patent/IL182835A0/en unknown
- 2007-05-25 ZA ZA200704318A patent/ZA200704318B/xx unknown
-
2012
- 2012-03-23 US US13/429,065 patent/US8334266B2/en not_active Expired - Fee Related