LU82514A1 - Derives n-(vinblastinoyl-23)d'acides amines,leur preparation et leur application therapeutique - Google Patents
Derives n-(vinblastinoyl-23)d'acides amines,leur preparation et leur application therapeutique Download PDFInfo
- Publication number
- LU82514A1 LU82514A1 LU82514A LU82514A LU82514A1 LU 82514 A1 LU82514 A1 LU 82514A1 LU 82514 A LU82514 A LU 82514A LU 82514 A LU82514 A LU 82514A LU 82514 A1 LU82514 A1 LU 82514A1
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- LU
- Luxembourg
- Prior art keywords
- vinblastine
- ethyl
- deacetyl
- carboxamide
- acid
- Prior art date
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- 150000003862 amino acid derivatives Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000340 anti-metabolite Effects 0.000 description 1
- 230000002927 anti-mitotic effect Effects 0.000 description 1
- 230000000118 anti-neoplastic effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229940053202 antiepileptics carboxamide derivative Drugs 0.000 description 1
- 229940100197 antimetabolite Drugs 0.000 description 1
- 239000002256 antimetabolite Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 150000008209 arabinosides Chemical class 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 235000009582 asparagine Nutrition 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 150000001576 beta-amino acids Chemical class 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- HYPLQEHLQMSBKE-VIFPVBQESA-N butyl (2s)-2-amino-4-methylpentanoate Chemical compound CCCCOC(=O)[C@@H](N)CC(C)C HYPLQEHLQMSBKE-VIFPVBQESA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 230000003327 cancerostatic effect Effects 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000032823 cell division Effects 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229960001338 colchicine Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229960003067 cystine Drugs 0.000 description 1
- 229940104302 cytosine Drugs 0.000 description 1
- NDMPLJNOPCLANR-PETVRERISA-N deacetylvinblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](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 NDMPLJNOPCLANR-PETVRERISA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000031864 metaphase Effects 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- QVDXUKJJGUSGLS-UHFFFAOYSA-N methyl 2-amino-4-methylpentanoate Chemical compound COC(=O)C(N)CC(C)C QVDXUKJJGUSGLS-UHFFFAOYSA-N 0.000 description 1
- QVDXUKJJGUSGLS-LURJTMIESA-N methyl L-leucinate Chemical compound COC(=O)[C@@H](N)CC(C)C QVDXUKJJGUSGLS-LURJTMIESA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 description 1
- 210000004688 microtubule Anatomy 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 231100000189 neurotoxic Toxicity 0.000 description 1
- 230000002887 neurotoxic effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 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 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- YNSIUGHLISOIRQ-SWSODSCOSA-N vinglycinate Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(=O)CN(C)C)[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 YNSIUGHLISOIRQ-SWSODSCOSA-N 0.000 description 1
- 229950008883 vinglycinate Drugs 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- DVPVGSLIUJPOCJ-XXRQFBABSA-N x1j761618a Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(=O)CN(C)C)[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.C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(=O)CN(C)C)[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 DVPVGSLIUJPOCJ-XXRQFBABSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/04—Dimeric indole alkaloids, e.g. vincaleucoblastine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Priority Applications (28)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| OA56972A OA06421A (fr) | 1980-06-10 | 1979-12-13 | Procédé de préparation de dérivés N-(vinblastinoyl-23) d'acides aminés et de peptides. |
| LU82514A LU82514A1 (fr) | 1980-06-10 | 1980-06-10 | Derives n-(vinblastinoyl-23)d'acides amines,leur preparation et leur application therapeutique |
| ES502644A ES502644A0 (es) | 1980-06-10 | 1981-05-30 | Procedimiento de obtencion de nuevos derivados de la vin- blastina |
| AU71262/81A AU541747B2 (en) | 1980-06-10 | 1981-06-02 | N-(vinblastinoyl-23)derivatives of amino acid and peptides |
| GR65133A GR74565B (enrdf_load_stackoverflow) | 1980-06-10 | 1981-06-02 | |
| NZ197299A NZ197299A (en) | 1980-06-10 | 1981-06-03 | N-(vinblastin-23-oyl)derivatives of aminoacids |
| US06/269,876 US4388305A (en) | 1980-06-10 | 1981-06-03 | Vinblastin-23-oyl amino acid derivatives for use as antitumor agents |
| CA000379041A CA1196326A (en) | 1980-06-10 | 1981-06-04 | Vinblastin-23-oyl amino acid derivatives |
| IL63038A IL63038A0 (en) | 1980-06-10 | 1981-06-04 | Vinblastine derivatives |
| IE1275/81A IE51403B1 (en) | 1980-06-10 | 1981-06-04 | N-(vinblastinolyl-23)derivatives of amino acid and peptides and methods for their preparation |
| AT0253881A AT390793B (de) | 1980-06-10 | 1981-06-05 | Verfahren zur herstellung von neuen n-(vinblastin-23-oyl)-aminosaeurederivaten und von deren saeureadditionssalzen |
| ZA00813781A ZA813781B (en) | 1980-06-10 | 1981-06-05 | N-(vinblastinoyl-23)derivatives of amino acid and peptides |
| DE19813122479 DE3122479A1 (de) | 1980-06-10 | 1981-06-05 | N-(vinblastin-23-oyl)-aminosaeurederivate |
| GB8117454A GB2078730A (en) | 1980-06-10 | 1981-06-08 | N-(vinblastinoyl-23) derivatives of amino acid and peptides |
| IT67782/81A IT1144601B (it) | 1980-06-10 | 1981-06-08 | Derivati della vinblastina procedimento per la loro preparazione e composizioni farmaceutiche contenenti tali derivati |
| JP8798581A JPS5728094A (en) | 1980-06-10 | 1981-06-08 | N-(vinblastine-23-oyl)amino acid derivative |
| DE8181870028T DE3166150D1 (en) | 1980-06-10 | 1981-06-09 | N-(vinblastinoyl-23) derivatives of amino acids and peptides and their preparation |
| AT81870028T ATE9475T1 (de) | 1980-06-10 | 1981-06-09 | Aminosaeure- und peptid-n-(vinblastinoyl-23)derivate und ihre herstellung. |
| BE0/205032A BE889136A (fr) | 1980-06-10 | 1981-06-09 | Derives n-(vinglastinoyl-23) d'acides amines et de peptides, leur preparation et leur application therapeutique |
| SE8103594A SE8103594L (sv) | 1980-06-10 | 1981-06-09 | N-(vinblastin-23-oyl)aminosyraderivat |
| DD81230660A DD160417A5 (de) | 1980-06-10 | 1981-06-09 | Verfahren zur herstellung von n-(vinblastin-23-oyl)-aminosaeurederivate |
| DK250181A DK160614C (da) | 1980-06-10 | 1981-06-09 | Analogifremgangsmaade til fremstilling af vinblastinderivater og farmaceutisk acceptable salte deraf |
| PT73161A PT73161B (fr) | 1980-06-10 | 1981-06-09 | Procede pour la preparation de derives de n-(vynblastinoyl-23) aux amino-acides et peptides et son application terapeutique |
| FR8111330A FR2483926A1 (fr) | 1980-06-10 | 1981-06-09 | Derives n-(vinblastinoyl-23) d'acides amines et de peptides, leur preparation et leur application therapeutique |
| EP81870028A EP0041935B1 (fr) | 1980-06-10 | 1981-06-09 | Dérivés n-(vinblastinoyl-23) d'acides aminés et de peptides ainsi que leur préparation |
| HU811725A HU185261B (en) | 1980-06-10 | 1981-06-10 | Process for preparing n-/vinblastinoyl-23/-derivatives of some aminoacids and peptides |
| NL8102802A NL8102802A (nl) | 1980-06-10 | 1981-06-10 | N-(vinblastin-23-oyl)aminozuurderivaten. |
| US06/446,708 US4639456A (en) | 1980-06-10 | 1982-12-03 | Vinblastin-23-oyl amino acid derivatives |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU82514A LU82514A1 (fr) | 1980-06-10 | 1980-06-10 | Derives n-(vinblastinoyl-23)d'acides amines,leur preparation et leur application therapeutique |
| LU82514 | 1980-06-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU82514A1 true LU82514A1 (fr) | 1982-01-20 |
Family
ID=19729417
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU82514A LU82514A1 (fr) | 1980-06-10 | 1980-06-10 | Derives n-(vinblastinoyl-23)d'acides amines,leur preparation et leur application therapeutique |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5728094A (enrdf_load_stackoverflow) |
| BE (1) | BE889136A (enrdf_load_stackoverflow) |
| LU (1) | LU82514A1 (enrdf_load_stackoverflow) |
| ZA (1) | ZA813781B (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0233101A1 (fr) * | 1986-01-13 | 1987-08-19 | Ire-Celltarg S.A. | Dérivés de vinblastine et composition pharmaceutique les contenant |
| US8940754B2 (en) * | 2010-02-22 | 2015-01-27 | The Scripps Research Institute | 10′-fluorinated Vinca alkaloids provide enhanced biological activity against MDR cancer cells |
-
1980
- 1980-06-10 LU LU82514A patent/LU82514A1/fr unknown
-
1981
- 1981-06-05 ZA ZA00813781A patent/ZA813781B/xx unknown
- 1981-06-08 JP JP8798581A patent/JPS5728094A/ja active Granted
- 1981-06-09 BE BE0/205032A patent/BE889136A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0210836B2 (enrdf_load_stackoverflow) | 1990-03-09 |
| ZA813781B (en) | 1982-06-30 |
| JPS5728094A (en) | 1982-02-15 |
| BE889136A (fr) | 1981-12-09 |
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