CS263291A3 - Taxol water-soluble derivatives - Google Patents
Taxol water-soluble derivatives Download PDFInfo
- Publication number
- CS263291A3 CS263291A3 CS912632A CS263291A CS263291A3 CS 263291 A3 CS263291 A3 CS 263291A3 CS 912632 A CS912632 A CS 912632A CS 263291 A CS263291 A CS 263291A CS 263291 A3 CS263291 A3 CS 263291A3
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- taxol
- derivatives
- group
- water
- solution
- Prior art date
Links
- 229960001592 paclitaxel Drugs 0.000 title claims description 101
- 229930012538 Paclitaxel Natural products 0.000 title claims description 95
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
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- 150000004579 taxol derivatives Chemical class 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 27
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- 238000000034 method Methods 0.000 claims description 24
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- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- SVWLIIFHXFGESG-UHFFFAOYSA-N formic acid;methanol Chemical compound OC.OC=O SVWLIIFHXFGESG-UHFFFAOYSA-N 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical group O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical class C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- PBMIETCUUSQZCG-UHFFFAOYSA-N n'-cyclohexylmethanediimine Chemical compound N=C=NC1CCCCC1 PBMIETCUUSQZCG-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000002271 resection Methods 0.000 description 1
- 150000003342 selenium Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical group C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring 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)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/573,731 US5059699A (en) | 1990-08-28 | 1990-08-28 | Water soluble derivatives of taxol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS263291A3 true CS263291A3 (en) | 1992-05-13 |
Family
ID=24293168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS912632A CS263291A3 (en) | 1990-08-28 | 1991-08-27 | Taxol water-soluble derivatives |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US5059699A (pl) |
| EP (1) | EP0473326A1 (pl) |
| JP (1) | JPH0699410B2 (pl) |
| KR (1) | KR0132157B1 (pl) |
| CN (1) | CN1059337A (pl) |
| AU (2) | AU645340B2 (pl) |
| CA (1) | CA2049160C (pl) |
| CS (1) | CS263291A3 (pl) |
| EG (1) | EG19914A (pl) |
| FI (1) | FI913651A7 (pl) |
| HU (1) | HU210326B (pl) |
| IE (1) | IE913015A1 (pl) |
| IL (1) | IL99183A0 (pl) |
| MX (2) | MX9100832A (pl) |
| MY (1) | MY107794A (pl) |
| NO (1) | NO913007L (pl) |
| NZ (1) | NZ239377A (pl) |
| OA (1) | OA10035A (pl) |
| PL (4) | PL166218B1 (pl) |
| PT (1) | PT98787A (pl) |
| RU (2) | RU2059630C1 (pl) |
| TW (1) | TW209214B (pl) |
| YU (1) | YU144891A (pl) |
| ZA (1) | ZA916450B (pl) |
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| US4469868A (en) * | 1982-05-24 | 1984-09-04 | Warner-Lambert Company | Alkylimidazo[1,2-c]pyrazolo[3,4-e]pyrimidines |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2601675B1 (fr) * | 1986-07-17 | 1988-09-23 | Rhone Poulenc Sante | Derives du taxol, leur preparation et les compositions pharmaceutiques qui les contiennent |
| FR2601676B1 (fr) * | 1986-07-17 | 1988-09-23 | Rhone Poulenc Sante | Procede de preparation du taxol et du desacetyl-10 taxol |
| US4942184A (en) * | 1988-03-07 | 1990-07-17 | The United States Of America As Represented By The Department Of Health And Human Services | Water soluble, antineoplastic derivatives of taxol |
| FR2629818B1 (fr) * | 1988-04-06 | 1990-11-16 | Centre Nat Rech Scient | Procede de preparation du taxol |
| US4960790A (en) * | 1989-03-09 | 1990-10-02 | University Of Kansas | Derivatives of taxol, pharmaceutical compositions thereof and methods for the preparation thereof |
-
1990
- 1990-08-28 US US07/573,731 patent/US5059699A/en not_active Expired - Fee Related
-
1991
- 1991-05-01 US US07/694,077 patent/US5352805A/en not_active Expired - Lifetime
- 1991-05-21 TW TW080103944A patent/TW209214B/zh active
- 1991-07-31 FI FI913651A patent/FI913651A7/fi not_active Application Discontinuation
- 1991-08-01 NO NO91913007A patent/NO913007L/no unknown
- 1991-08-13 NZ NZ239377A patent/NZ239377A/xx unknown
- 1991-08-13 CN CN91105549A patent/CN1059337A/zh active Pending
- 1991-08-13 EP EP91307460A patent/EP0473326A1/en not_active Withdrawn
- 1991-08-14 IL IL99183A patent/IL99183A0/xx unknown
- 1991-08-14 CA CA002049160A patent/CA2049160C/en not_active Expired - Fee Related
- 1991-08-15 ZA ZA916450A patent/ZA916450B/xx unknown
- 1991-08-19 OA OA60065A patent/OA10035A/en unknown
- 1991-08-21 HU HU912755A patent/HU210326B/hu not_active IP Right Cessation
- 1991-08-23 MY MYPI91001533A patent/MY107794A/en unknown
- 1991-08-26 KR KR1019910014772A patent/KR0132157B1/ko not_active Expired - Fee Related
- 1991-08-27 CS CS912632A patent/CS263291A3/cs unknown
- 1991-08-27 IE IE301591A patent/IE913015A1/en unknown
- 1991-08-27 MX MX9100832A patent/MX9100832A/es not_active IP Right Cessation
- 1991-08-27 RU SU915001413A patent/RU2059630C1/ru active
- 1991-08-27 PT PT98787A patent/PT98787A/pt not_active Application Discontinuation
- 1991-08-28 AU AU82745/91A patent/AU645340B2/en not_active Ceased
- 1991-08-28 PL PL91295891A patent/PL166218B1/pl unknown
- 1991-08-28 PL PL91291546A patent/PL166213B1/pl unknown
- 1991-08-28 EG EG51691A patent/EG19914A/xx active
- 1991-08-28 JP JP3217092A patent/JPH0699410B2/ja not_active Expired - Lifetime
- 1991-08-28 PL PL91295892A patent/PL166242B1/pl unknown
- 1991-08-28 YU YU144891A patent/YU144891A/sh unknown
- 1991-08-28 PL PL91295890A patent/PL166224B1/pl unknown
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1992
- 1992-10-14 RU RU9292004362A patent/RU2043346C1/ru active
- 1992-10-14 MX MX9205895A patent/MX9205895A/es not_active IP Right Cessation
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- 1993-04-26 AU AU37184/93A patent/AU654085B1/en not_active Ceased
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