FI111247B - Uusi b-fenyyli-isoseriinijohdannainen, sen valmistus ja käyttö - Google Patents
Uusi b-fenyyli-isoseriinijohdannainen, sen valmistus ja käyttö Download PDFInfo
- Publication number
- FI111247B FI111247B FI923679A FI923679A FI111247B FI 111247 B FI111247 B FI 111247B FI 923679 A FI923679 A FI 923679A FI 923679 A FI923679 A FI 923679A FI 111247 B FI111247 B FI 111247B
- Authority
- FI
- Finland
- Prior art keywords
- compound
- preparation
- salt
- ester
- phenylisoserine
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- RZARFIRJROUVLM-GVHYBUMESA-N (3r)-3-amino-2-hydroxy-3-phenylpropanoic acid Chemical class OC(=O)C(O)[C@H](N)C1=CC=CC=C1 RZARFIRJROUVLM-GVHYBUMESA-N 0.000 claims abstract description 3
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- -1 alkali metal salt Chemical class 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- RZARFIRJROUVLM-JGVFFNPUSA-N (2r,3s)-3-azaniumyl-2-hydroxy-3-phenylpropanoate Chemical compound [O-]C(=O)[C@H](O)[C@@H]([NH3+])C1=CC=CC=C1 RZARFIRJROUVLM-JGVFFNPUSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 229930012538 Paclitaxel Natural products 0.000 abstract 1
- 229960001592 paclitaxel Drugs 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 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 abstract 1
- 239000002253 acid Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- ZLRFPQPVXRIBCQ-UHFFFAOYSA-N 2-$l^{1}-oxidanyl-2-methylpropane Chemical group CC(C)(C)[O] ZLRFPQPVXRIBCQ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical group C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- IDKGOWNLIAJLAU-UHFFFAOYSA-N 3-(benzylamino)-2-hydroxy-3-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(O)C(O)=O)NCC1=CC=CC=C1 IDKGOWNLIAJLAU-UHFFFAOYSA-N 0.000 description 1
- 206010000830 Acute leukaemia Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- WZPZWAQKLOPJEL-DTWKUNHWSA-N methyl (2r,3s)-3-amino-2-hydroxy-3-phenylpropanoate Chemical compound COC(=O)[C@H](O)[C@@H](N)C1=CC=CC=C1 WZPZWAQKLOPJEL-DTWKUNHWSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- 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
- 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
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9002099 | 1990-02-21 | ||
| FR9002099A FR2658510B1 (fr) | 1990-02-21 | 1990-02-21 | Nouveau derive de la beta-phenylisoserine, sa preparation et son emploi. |
| FR9100132 | 1991-01-07 | ||
| PCT/FR1991/000132 WO1991013053A1 (fr) | 1990-02-21 | 1991-02-20 | DERIVE DE LA β-PHENYLISOSERINE, SA PREPARATION ET SON EMPLOI |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI923679A0 FI923679A0 (fi) | 1992-08-17 |
| FI923679A FI923679A (fi) | 1992-08-17 |
| FI111247B true FI111247B (fi) | 2003-06-30 |
Family
ID=9393962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI923679A FI111247B (fi) | 1990-02-21 | 1992-08-17 | Uusi b-fenyyli-isoseriinijohdannainen, sen valmistus ja käyttö |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US5359124A (de) |
| EP (1) | EP0515540B1 (de) |
| JP (1) | JP3057097B2 (de) |
| KR (1) | KR100197481B1 (de) |
| AT (1) | ATE108176T1 (de) |
| AU (1) | AU642717B2 (de) |
| CA (1) | CA2071983C (de) |
| CZ (1) | CZ279656B6 (de) |
| DE (1) | DE69102762T2 (de) |
| DK (1) | DK0515540T3 (de) |
| ES (1) | ES2056639T3 (de) |
| FI (1) | FI111247B (de) |
| FR (1) | FR2658510B1 (de) |
| HU (1) | HU209615B (de) |
| IE (1) | IE64397B1 (de) |
| IL (1) | IL97277A (de) |
| NO (1) | NO179865C (de) |
| PT (1) | PT96849B (de) |
| RU (1) | RU2074172C1 (de) |
| SK (1) | SK278304B6 (de) |
| WO (1) | WO1991013053A1 (de) |
| YU (1) | YU48671B (de) |
| ZA (1) | ZA911211B (de) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5939561A (en) * | 1992-03-10 | 1999-08-17 | Rhone-Poulence Rorer S.A. | Process for the preparation of β-phenylisoserine and β-lactam and their analogues |
| FR2688499B1 (fr) * | 1992-03-10 | 1994-05-06 | Rhone Poulenc Rorer Sa | Procede de preparation de la beta-phenylisoserine et de ses analogues. |
| EP0639186B1 (de) * | 1992-04-17 | 1999-06-23 | Abbott Laboratories | Taxol-derivate |
| IL107950A (en) | 1992-12-15 | 2001-04-30 | Upjohn Co | b 7, b 8 - Matano - Taxols, their preparation and pharmaceutical preparations against malignant tumors containing them |
| ATE192147T1 (de) * | 1993-06-11 | 2000-05-15 | Upjohn Co | Delta 6, 7-taxolen, antineoplastische verwendung und diese enthaltende pharmazeutische zusammenstellungen |
| IL127597A (en) * | 1994-01-28 | 2003-07-31 | Upjohn Co | Iso-taxol analogs |
| US5580899A (en) | 1995-01-09 | 1996-12-03 | The Liposome Company, Inc. | Hydrophobic taxane derivatives |
| US6107332A (en) | 1995-09-12 | 2000-08-22 | The Liposome Company, Inc. | Hydrolysis-promoting hydrophobic taxane derivatives |
| US6051600A (en) * | 1995-09-12 | 2000-04-18 | Mayhew; Eric | Liposomal hydrolysis-promoting hydrophobic taxane derivatives |
| EP2861256B1 (de) | 2012-06-15 | 2019-10-23 | The Brigham and Women's Hospital, Inc. | Zusammensetzungen zur behandlung von krebs und verfahren zur herstellung davon |
| AU2015241198A1 (en) | 2014-04-03 | 2016-11-17 | Invictus Oncology Pvt. Ltd. | Supramolecular combinatorial therapeutics |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1108180A (en) * | 1976-07-21 | 1981-09-01 | Hamao Umezawa | Analogs of bestatin |
| FR2629819B1 (fr) * | 1988-04-06 | 1990-11-16 | Rhone Poulenc Sante | Procede de preparation de derives de la baccatine iii et de la desacetyl-10 baccatine iii |
| FR2629818B1 (fr) * | 1988-04-06 | 1990-11-16 | Centre Nat Rech Scient | Procede de preparation du taxol |
| US5175315A (en) * | 1989-05-31 | 1992-12-29 | Florida State University | Method for preparation of taxol using β-lactam |
| FR2662440B1 (fr) * | 1990-05-22 | 1992-07-31 | Rhone Poulenc Sante | Procede de preparation stereoselective de derives de la phenylisoserine. |
| FR2662441B1 (fr) * | 1990-05-22 | 1992-10-23 | Rhone Poulenc Sante | Procede de preparation enantioselective de derives de la phenylisoserine. |
-
1990
- 1990-02-21 FR FR9002099A patent/FR2658510B1/fr not_active Expired - Lifetime
-
1991
- 1991-02-19 ZA ZA911211A patent/ZA911211B/xx unknown
- 1991-02-19 IL IL9727791A patent/IL97277A/en not_active IP Right Cessation
- 1991-02-20 DK DK91905054.2T patent/DK0515540T3/da active
- 1991-02-20 AU AU73453/91A patent/AU642717B2/en not_active Expired
- 1991-02-20 DE DE69102762T patent/DE69102762T2/de not_active Expired - Lifetime
- 1991-02-20 CA CA002071983A patent/CA2071983C/fr not_active Expired - Lifetime
- 1991-02-20 WO PCT/FR1991/000132 patent/WO1991013053A1/fr active IP Right Grant
- 1991-02-20 SK SK438-91A patent/SK278304B6/sk not_active IP Right Cessation
- 1991-02-20 JP JP3505196A patent/JP3057097B2/ja not_active Expired - Lifetime
- 1991-02-20 CZ CS91438A patent/CZ279656B6/cs not_active IP Right Cessation
- 1991-02-20 EP EP91905054A patent/EP0515540B1/de not_active Expired - Lifetime
- 1991-02-20 AT AT91905054T patent/ATE108176T1/de not_active IP Right Cessation
- 1991-02-20 KR KR1019920701998A patent/KR100197481B1/ko not_active IP Right Cessation
- 1991-02-20 US US07/920,508 patent/US5359124A/en not_active Expired - Lifetime
- 1991-02-20 IE IE58691A patent/IE64397B1/en not_active IP Right Cessation
- 1991-02-20 HU HU9202667A patent/HU209615B/hu unknown
- 1991-02-20 ES ES91905054T patent/ES2056639T3/es not_active Expired - Lifetime
- 1991-02-20 RU SU915053004A patent/RU2074172C1/ru active
- 1991-02-21 PT PT96849A patent/PT96849B/pt not_active IP Right Cessation
- 1991-02-21 YU YU31191A patent/YU48671B/sh unknown
-
1992
- 1992-08-17 FI FI923679A patent/FI111247B/fi active
- 1992-08-18 NO NO923226A patent/NO179865C/no not_active IP Right Cessation
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