KR20070089795A - 칸포스파미드 및 그의 염의 제조 방법 및 중간체, 일부중간체를 함유하는 약제학적 조성물, 및 항암제로서의그들의 용도 - Google Patents
칸포스파미드 및 그의 염의 제조 방법 및 중간체, 일부중간체를 함유하는 약제학적 조성물, 및 항암제로서의그들의 용도 Download PDFInfo
- Publication number
- KR20070089795A KR20070089795A KR1020077012351A KR20077012351A KR20070089795A KR 20070089795 A KR20070089795 A KR 20070089795A KR 1020077012351 A KR1020077012351 A KR 1020077012351A KR 20077012351 A KR20077012351 A KR 20077012351A KR 20070089795 A KR20070089795 A KR 20070089795A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- optionally substituted
- protecting group
- amine
- oxycarbonyl
- 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.)
- Abandoned
Links
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- 238000000034 method Methods 0.000 title claims abstract description 34
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
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- 239000000543 intermediate Substances 0.000 title abstract description 5
- 230000008569 process Effects 0.000 claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 132
- 229910052757 nitrogen Inorganic materials 0.000 claims description 70
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 49
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 49
- 125000006242 amine protecting group Chemical group 0.000 claims description 45
- 206010028980 Neoplasm Diseases 0.000 claims description 40
- -1 Phenyloxy Chemical group 0.000 claims description 33
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 23
- 201000011510 cancer Diseases 0.000 claims description 23
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 22
- 229940011051 isopropyl acetate Drugs 0.000 claims description 22
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 22
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- 125000004434 sulfur atom Chemical group 0.000 claims description 6
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- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 4
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- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- HJKYXKSLRZKNSI-UHFFFAOYSA-I pentapotassium;hydrogen sulfate;oxido sulfate;sulfuric acid Chemical group [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 description 2
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- 239000008346 aqueous phase Substances 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
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- 230000000171 quenching effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 206010038038 rectal cancer Diseases 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 201000001275 rectum cancer Diseases 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000003938 response to stress Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 210000000130 stem cell Anatomy 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- ZGYICYBLPGRURT-UHFFFAOYSA-N tri(propan-2-yl)silicon Chemical compound CC(C)[Si](C(C)C)C(C)C ZGYICYBLPGRURT-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/36—Amides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0205—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-(X)3-C(=0)-, e.g. statine or derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2408—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of hydroxyalkyl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/26—Amides of acids of phosphorus containing P-halide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0215—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing natural amino acids, forming a peptide bond via their side chain functional group, e.g. epsilon-Lys, gamma-Glu
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/0606—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing heteroatoms not provided for by C07K5/06086 - C07K5/06139, e.g. Ser, Met, Cys, Thr
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/018,391 US8198247B2 (en) | 2004-12-21 | 2004-12-21 | Process for and intermediates in the preparation of canfosfamide and its salts |
| US11/018,391 | 2004-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20070089795A true KR20070089795A (ko) | 2007-09-03 |
Family
ID=36216909
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020077012351A Abandoned KR20070089795A (ko) | 2004-12-21 | 2005-11-23 | 칸포스파미드 및 그의 염의 제조 방법 및 중간체, 일부중간체를 함유하는 약제학적 조성물, 및 항암제로서의그들의 용도 |
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 |
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| US5556942A (en) * | 1991-04-29 | 1996-09-17 | Terrapin Technologies, Inc. | Glutathione S-transferase-activated compounds |
| US6627732B1 (en) * | 1998-04-16 | 2003-09-30 | Teijin Limited | Glutathione derivatives and their dosage forms |
| 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 |
| CN101090977B (zh) * | 2005-01-06 | 2013-04-10 | 泰立克公司 | 三肽和四肽硫醚 |
-
2004
- 2004-12-21 US US11/018,391 patent/US8198247B2/en not_active Expired - Fee Related
-
2005
- 2005-11-23 BR BRPI0519141-6A patent/BRPI0519141A2/pt not_active IP Right Cessation
- 2005-11-23 EA EA200701180A patent/EA016052B1/ru not_active IP Right Cessation
- 2005-11-23 WO PCT/US2005/042693 patent/WO2006068769A1/en not_active Ceased
- 2005-11-23 MX MX2007007215A patent/MX2007007215A/es active IP Right Grant
- 2005-11-23 AU AU2005319579A patent/AU2005319579B2/en not_active Ceased
- 2005-11-23 EP EP05852166.7A patent/EP1827605B1/en not_active Expired - Lifetime
- 2005-11-23 CA CA002587088A patent/CA2587088A1/en not_active Abandoned
- 2005-11-23 JP JP2007548240A patent/JP5060306B2/ja not_active Expired - Fee Related
- 2005-11-23 TW TW094141102A patent/TW200633717A/zh unknown
- 2005-11-23 CN CN2005800428600A patent/CN101080251B/zh not_active Expired - Fee Related
- 2005-11-23 KR KR1020077012351A patent/KR20070089795A/ko not_active Abandoned
- 2005-12-15 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
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2012
- 2012-03-23 US US13/429,065 patent/US8334266B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006068769A1 (en) | 2006-06-29 |
| AU2005319579B2 (en) | 2011-07-21 |
| CN101080251A (zh) | 2007-11-28 |
| JP2008524327A (ja) | 2008-07-10 |
| US8334266B2 (en) | 2012-12-18 |
| BRPI0519141A2 (pt) | 2008-12-30 |
| IL182835A0 (en) | 2007-08-19 |
| TW200633717A (en) | 2006-10-01 |
| JP5060306B2 (ja) | 2012-10-31 |
| AR052167A1 (es) | 2007-03-07 |
| EP1827605A1 (en) | 2007-09-05 |
| MX2007007215A (es) | 2007-08-14 |
| EP1827605B1 (en) | 2014-03-26 |
| US20120238772A1 (en) | 2012-09-20 |
| CA2587088A1 (en) | 2006-06-29 |
| AU2005319579A1 (en) | 2006-06-29 |
| US20060135409A1 (en) | 2006-06-22 |
| ZA200704318B (en) | 2008-09-25 |
| US8198247B2 (en) | 2012-06-12 |
| EA016052B1 (ru) | 2012-01-30 |
| CN101080251B (zh) | 2012-08-29 |
| EA200701180A1 (ru) | 2008-04-28 |
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