NZ202708A - N-(vinblastinoyl-23)derivatives of amino acids,their preparation and pharmaceutical compositions - Google Patents
N-(vinblastinoyl-23)derivatives of amino acids,their preparation and pharmaceutical compositionsInfo
- Publication number
- NZ202708A NZ202708A NZ202708A NZ20270882A NZ202708A NZ 202708 A NZ202708 A NZ 202708A NZ 202708 A NZ202708 A NZ 202708A NZ 20270882 A NZ20270882 A NZ 20270882A NZ 202708 A NZ202708 A NZ 202708A
- Authority
- NZ
- New Zealand
- Prior art keywords
- group
- ethyl
- alkyl
- oyl
- deacetyl
- Prior art date
Links
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- 239000002256 antimetabolite Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
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- 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
- 230000015572 biosynthetic process Effects 0.000 description 1
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- 230000032823 cell division Effects 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 229960001338 colchicine Drugs 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
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- 229960003067 cystine Drugs 0.000 description 1
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 1
- 229960000975 daunorubicin Drugs 0.000 description 1
- YSMODUONRAFBET-UHFFFAOYSA-N delta-DL-hydroxylysine Natural products NCC(O)CCC(N)C(O)=O YSMODUONRAFBET-UHFFFAOYSA-N 0.000 description 1
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- YSMODUONRAFBET-UHNVWZDZSA-N erythro-5-hydroxy-L-lysine Chemical compound NC[C@H](O)CC[C@H](N)C(O)=O YSMODUONRAFBET-UHNVWZDZSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229960002949 fluorouracil Drugs 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 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
- 229960002743 glutamine Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 229960002885 histidine Drugs 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- QJHBJHUKURJDLG-UHFFFAOYSA-N hydroxy-L-lysine Natural products NCCCCC(NO)C(O)=O QJHBJHUKURJDLG-UHFFFAOYSA-N 0.000 description 1
- 229960002591 hydroxyproline Drugs 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 208000003747 lymphoid leukemia Diseases 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229960001428 mercaptopurine Drugs 0.000 description 1
- 230000031864 metaphase Effects 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 229960004452 methionine Drugs 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- 210000004688 microtubule Anatomy 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- OBEIXXHHUOSBLA-UQUCNHJPSA-N n-deformylvincristine 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)N3)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 OBEIXXHHUOSBLA-UQUCNHJPSA-N 0.000 description 1
- 230000002887 neurotoxic effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000009935 nitrosation Effects 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 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
- 238000001556 precipitation Methods 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 229960002429 proline Drugs 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000004083 survival effect Effects 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
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229960003087 tioguanine Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- OHSJPLSEQNCRLW-UHFFFAOYSA-N triphenylmethyl radical Chemical compound C1=CC=CC=C1[C](C=1C=CC=CC=1)C1=CC=CC=C1 OHSJPLSEQNCRLW-UHFFFAOYSA-N 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-M tryptophanate Chemical compound C1=CC=C2C(CC(N)C([O-])=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-M 0.000 description 1
- 229960004441 tyrosine Drugs 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
- CXBGOBGJHGGWIE-IYJDUVQVSA-N vindoline Chemical compound CN([C@H]1[C@](O)([C@@H]2OC(C)=O)C(=O)OC)C3=CC(OC)=CC=C3[C@]11CCN3CC=C[C@]2(CC)[C@@H]13 CXBGOBGJHGGWIE-IYJDUVQVSA-N 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
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU83822A LU83822A1 (fr) | 1981-12-08 | 1981-12-08 | Derives n-(vinblastinoyl-23)d'acides amines,leur preparation et leur application therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ202708A true NZ202708A (en) | 1986-01-24 |
Family
ID=19729780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ202708A NZ202708A (en) | 1981-12-08 | 1982-12-03 | N-(vinblastinoyl-23)derivatives of amino acids,their preparation and pharmaceutical compositions |
Country Status (24)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3484691D1 (de) * | 1983-04-29 | 1991-07-18 | Omnichem Sa | Konjugierte vinblastin-verbindungen und ihre derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zusammensetzungen. |
| US4675400A (en) * | 1985-06-17 | 1987-06-23 | Eli Lilly And Company | Bifunctional derivatives of 4-desacetyl indole-dihydroindole alkaloids |
| US4667030A (en) * | 1985-06-17 | 1987-05-19 | Eli Lilly And Company | Hydrazide succinimide derivatives of antineoplastic indole-dihydroindole alkaloids |
| JPH075608B2 (ja) * | 1986-01-13 | 1995-01-25 | イ−ル−セルタ−ク ソシエテ アノニム | ビンブラスチン誘導体 |
| US4906086A (en) * | 1987-06-19 | 1990-03-06 | Honda Giken Kogyo Kabushiki Kaisha | Rearview mirror device for motorcycles |
| FR2626882B1 (fr) * | 1988-02-08 | 1991-11-08 | Ire Celltarg Sa | Conjugues de derives de vinca comportant une chaine detergente en position c-3 |
| US10377774B2 (en) * | 2013-04-19 | 2019-08-13 | Jinan University | Vinblastine derivatives, preparation method therefor and application thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR204004A1 (es) | 1973-04-02 | 1975-11-12 | Lilly Co Eli | Procedimientos para preparar derivados de vinblastina leurosidina y leurocristina |
| US3848234A (en) * | 1973-04-04 | 1974-11-12 | Sperry Rand Corp | Multi-processor system with multiple cache memories |
| IL48685A (en) * | 1975-01-09 | 1980-03-31 | Lilly Co Eli | Amides of vincadioline and vinblastine |
| OA06421A (fr) * | 1980-06-10 | 1981-09-30 | Omnium Chimique Sa | Procédé de préparation de dérivés N-(vinblastinoyl-23) d'acides aminés et de peptides. |
-
1981
- 1981-12-08 LU LU83822A patent/LU83822A1/fr unknown
-
1982
- 1982-11-24 AU AU90847/82A patent/AU564951B2/en not_active Ceased
- 1982-11-30 IL IL67366A patent/IL67366A/xx unknown
- 1982-12-01 ZA ZA828823A patent/ZA828823B/xx unknown
- 1982-12-01 CH CH6980/82A patent/CH655727A5/fr not_active IP Right Cessation
- 1982-12-03 NZ NZ202708A patent/NZ202708A/en unknown
- 1982-12-03 CA CA000416996A patent/CA1198422A/en not_active Expired
- 1982-12-06 ES ES517942A patent/ES8401768A1/es not_active Expired
- 1982-12-06 NL NL8204711A patent/NL8204711A/nl not_active Application Discontinuation
- 1982-12-06 GR GR69997A patent/GR77280B/el unknown
- 1982-12-07 PT PT75949A patent/PT75949B/pt not_active IP Right Cessation
- 1982-12-07 FR FR828220476A patent/FR2517680B1/fr not_active Expired - Lifetime
- 1982-12-07 JP JP57214573A patent/JPS58116491A/ja active Granted
- 1982-12-07 IT IT68431/82A patent/IT1157126B/it active
- 1982-12-07 SE SE8206981A patent/SE452622B/sv not_active IP Right Cessation
- 1982-12-07 HU HU823919A patent/HU187803B/hu unknown
- 1982-12-07 DE DE19823245269 patent/DE3245269A1/de not_active Withdrawn
- 1982-12-07 DK DK541882A patent/DK161833C/da not_active IP Right Cessation
- 1982-12-07 IE IE2906/82A patent/IE55283B1/en not_active IP Right Cessation
- 1982-12-07 AT AT0444982A patent/AT390958B/de not_active IP Right Cessation
- 1982-12-07 BE BE0/209661A patent/BE895262A/fr not_active IP Right Cessation
- 1982-12-08 GB GB08234965A patent/GB2111055B/en not_active Expired
- 1982-12-08 OA OA57864A patent/OA07270A/xx unknown
- 1982-12-08 DD DD82245703A patent/DD205906A5/de not_active IP Right Cessation
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