CA2022538C - Derives n-(vincristinoyl-23) et n-(noranhydro-5' vinblastinoyl-23) d'acide amino-1 methylphosphonique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent - Google Patents
Derives n-(vincristinoyl-23) et n-(noranhydro-5' vinblastinoyl-23) d'acide amino-1 methylphosphonique, leur procede de preparation et les compositions pharmaceutiques qui les contiennentInfo
- Publication number
- CA2022538C CA2022538C CA002022538A CA2022538A CA2022538C CA 2022538 C CA2022538 C CA 2022538C CA 002022538 A CA002022538 A CA 002022538A CA 2022538 A CA2022538 A CA 2022538A CA 2022538 C CA2022538 C CA 2022538C
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- ppm
- radical
- compounds
- formula
- general formula
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- 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.)
- Expired - Fee Related
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- 230000008569 process Effects 0.000 title claims description 6
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 83
- -1 alkyl radical Chemical class 0.000 claims abstract description 32
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- 239000000203 mixture Substances 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims abstract description 11
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- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims abstract description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
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- 238000010790 dilution Methods 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 208000010932 epithelial neoplasm Diseases 0.000 description 1
- 230000001605 fetal effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- 229960003390 magnesium sulfate Drugs 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 229940073640 magnesium sulfate anhydrous Drugs 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 201000009410 rhabdomyosarcoma Diseases 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- GBABOYUKABKIAF-IELIFDKJSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-IELIFDKJSA-N 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- 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 Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (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)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8910554A FR2651348B1 (US06252093-20010626-C00008.png) | 1989-08-04 | 1989-08-04 | |
| FR89.10554 | 1989-08-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2022538A1 CA2022538A1 (fr) | 1991-02-05 |
| CA2022538C true CA2022538C (fr) | 1996-09-24 |
Family
ID=9384495
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002022538A Expired - Fee Related CA2022538C (fr) | 1989-08-04 | 1990-08-02 | Derives n-(vincristinoyl-23) et n-(noranhydro-5' vinblastinoyl-23) d'acide amino-1 methylphosphonique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Country Status (15)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5508463A (en) * | 1994-03-17 | 1996-04-16 | Trustees Of The University Of Pennsylvania | α-aminophosphonates |
| EP1229934B1 (en) | 1999-10-01 | 2014-03-05 | Immunogen, Inc. | Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3354163A (en) * | 1966-12-15 | 1967-11-21 | Eli Lillty And Company | Nu-desmethylvinblastine |
| HU165986B (US06252093-20010626-C00008.png) * | 1973-02-16 | 1974-12-28 | ||
| US4307100A (en) * | 1978-08-24 | 1981-12-22 | Agence Nationale De Valorisation De La Recherche (Anvar) | Nor bis-indole compounds usable as medicaments |
| US4210584A (en) * | 1979-01-15 | 1980-07-01 | Eli Lilly And Company | Vindesine synthesis |
| LU84640A1 (fr) * | 1983-02-10 | 1984-11-08 | Onmichem S A | Nouveau procede d'obtention de la vincristine et du sulfate de vincristine |
| US4619935A (en) * | 1983-03-17 | 1986-10-28 | Eli Lilly And Company | Stable oncolytic formulations |
| US4522750A (en) * | 1984-02-21 | 1985-06-11 | Eli Lilly And Company | Cytotoxic compositions of transferrin coupled to vinca alkaloids |
| FR2623504B1 (fr) * | 1987-11-25 | 1990-03-09 | Adir | Nouveaux derives n-(vinblastinoyl-23) d'acide amino-1 methylphosphonique, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent |
| US4923876A (en) * | 1988-04-18 | 1990-05-08 | Cetus Corporation | Vinca alkaloid pharmaceutical compositions |
-
1989
- 1989-08-04 FR FR8910554A patent/FR2651348B1/fr not_active Expired - Fee Related
-
1990
- 1990-07-27 ZA ZA905924A patent/ZA905924B/xx unknown
- 1990-08-01 US US07/561,065 patent/US5100881A/en not_active Expired - Fee Related
- 1990-08-02 CA CA002022538A patent/CA2022538C/fr not_active Expired - Fee Related
- 1990-08-03 AU AU60149/90A patent/AU625885B2/en not_active Ceased
- 1990-08-03 ES ES90402226T patent/ES2060979T3/es not_active Expired - Lifetime
- 1990-08-03 DE DE69011235T patent/DE69011235T2/de not_active Expired - Fee Related
- 1990-08-03 AT AT90402226T patent/ATE109485T1/de active
- 1990-08-03 IE IE280890A patent/IE66007B1/en not_active IP Right Cessation
- 1990-08-03 JP JP2206668A patent/JPH075619B2/ja not_active Expired - Lifetime
- 1990-08-03 NZ NZ234771A patent/NZ234771A/en unknown
- 1990-08-03 DK DK90402226.6T patent/DK0412015T3/da active
- 1990-08-03 PT PT94906A patent/PT94906B/pt not_active IP Right Cessation
- 1990-08-03 EP EP90402226A patent/EP0412015B1/fr not_active Expired - Lifetime
- 1990-08-03 OA OA59827A patent/OA09299A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE66007B1 (en) | 1995-11-29 |
| NZ234771A (en) | 1992-05-26 |
| IE902808A1 (en) | 1991-02-27 |
| AU625885B2 (en) | 1992-07-16 |
| FR2651348B1 (US06252093-20010626-C00008.png) | 1993-01-22 |
| OA09299A (fr) | 1992-09-15 |
| ATE109485T1 (de) | 1994-08-15 |
| PT94906A (pt) | 1991-04-18 |
| DE69011235T2 (de) | 1995-03-09 |
| US5100881A (en) | 1992-03-31 |
| FR2651348A1 (US06252093-20010626-C00008.png) | 1991-03-01 |
| ES2060979T3 (es) | 1994-12-01 |
| JPH075619B2 (ja) | 1995-01-25 |
| DE69011235D1 (de) | 1994-09-08 |
| PT94906B (pt) | 1997-03-31 |
| JPH03118388A (ja) | 1991-05-20 |
| AU6014990A (en) | 1991-02-07 |
| EP0412015A1 (fr) | 1991-02-06 |
| EP0412015B1 (fr) | 1994-08-03 |
| ZA905924B (en) | 1991-05-29 |
| DK0412015T3 (da) | 1994-11-28 |
| CA2022538A1 (fr) | 1991-02-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |