PL104309B1 - Sposob wytwarzania nowych,dimetrycznych indolodwuwodoroindolokarbonamidow - Google Patents
Sposob wytwarzania nowych,dimetrycznych indolodwuwodoroindolokarbonamidow Download PDFInfo
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- PL104309B1 PL104309B1 PL1977200607A PL20060777A PL104309B1 PL 104309 B1 PL104309 B1 PL 104309B1 PL 1977200607 A PL1977200607 A PL 1977200607A PL 20060777 A PL20060777 A PL 20060777A PL 104309 B1 PL104309 B1 PL 104309B1
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- vlb
- group
- formula
- acid
- azide
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- -1 INDOLIUM HYDROGEN Chemical class 0.000 title claims description 42
- 239000001257 hydrogen Substances 0.000 title claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 150000001412 amines Chemical class 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 45
- 150000001540 azides Chemical class 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 150000001408 amides Chemical class 0.000 claims description 17
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 8
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 claims description 6
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
- KKYSBGWCYXYOHA-UHFFFAOYSA-N 3-methylthiopropylamine Chemical compound CSCCCN KKYSBGWCYXYOHA-UHFFFAOYSA-N 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- SXJOFVRRTUCRID-UHFFFAOYSA-N 1h-indole-2-carbonyl azide Chemical compound C1=CC=C2NC(C(=O)N=[N+]=[N-])=CC2=C1 SXJOFVRRTUCRID-UHFFFAOYSA-N 0.000 claims 1
- YSWFMQGCLBXBHU-UHFFFAOYSA-N 2-aminoethyl butanoate Chemical compound CCCC(=O)OCCN YSWFMQGCLBXBHU-UHFFFAOYSA-N 0.000 claims 1
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- 238000001228 spectrum Methods 0.000 description 18
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- 239000002904 solvent Substances 0.000 description 14
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 4
- JXLYSJRDGCGARV-PJXZDTQASA-N Leurosidine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-PJXZDTQASA-N 0.000 description 4
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- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical class C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
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- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
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- JXLYSJRDGCGARV-CFWMRBGOSA-N vinblastine 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-CFWMRBGOSA-N 0.000 description 1
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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)
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72165076A | 1976-09-08 | 1976-09-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL200607A1 PL200607A1 (pl) | 1978-05-22 |
| PL104309B1 true PL104309B1 (pl) | 1979-08-31 |
Family
ID=24898757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1977200607A PL104309B1 (pl) | 1976-09-08 | 1977-09-01 | Sposob wytwarzania nowych,dimetrycznych indolodwuwodoroindolokarbonamidow |
Country Status (27)
| Country | Link |
|---|---|
| JP (1) | JPS5340799A (en, 2012) |
| AR (3) | AR226411A1 (en, 2012) |
| AT (1) | AT360513B (en, 2012) |
| AU (1) | AU511055B2 (en, 2012) |
| BE (1) | BE858451A (en, 2012) |
| CA (1) | CA1082179A (en, 2012) |
| CH (1) | CH631990A5 (en, 2012) |
| DD (1) | DD133055A5 (en, 2012) |
| DE (1) | DE2739443A1 (en, 2012) |
| DK (1) | DK146822C (en, 2012) |
| ES (1) | ES462229A1 (en, 2012) |
| FR (1) | FR2364220A1 (en, 2012) |
| GB (1) | GB1586709A (en, 2012) |
| GR (1) | GR69783B (en, 2012) |
| HU (1) | HU180722B (en, 2012) |
| IE (1) | IE45558B1 (en, 2012) |
| IL (1) | IL52731A0 (en, 2012) |
| MX (1) | MX4740E (en, 2012) |
| NL (1) | NL7709806A (en, 2012) |
| NZ (1) | NZ184932A (en, 2012) |
| PH (1) | PH14771A (en, 2012) |
| PL (1) | PL104309B1 (en, 2012) |
| PT (1) | PT66984B (en, 2012) |
| RO (3) | RO77922A (en, 2012) |
| SE (1) | SE434953B (en, 2012) |
| YU (1) | YU209777A (en, 2012) |
| ZA (1) | ZA774988B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE30561E (en) * | 1976-12-06 | 1981-03-31 | Eli Lilly And Company | Vinca alkaloid intermediates |
| US4199504A (en) * | 1978-05-15 | 1980-04-22 | Eli Lilly And Company | Bridged cathranthus alkaloid dimers |
| AR225153A1 (es) * | 1978-10-10 | 1982-02-26 | Lilly Co Eli | Un procedimiento para la preparacion de sulfato de vindesina |
| US4357334A (en) | 1980-03-20 | 1982-11-02 | Eli Lilly And Company | Use of VLB 3-(2-chloroethyl) carboxamide in treating neoplasms |
| 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. |
| US4362664A (en) * | 1980-12-29 | 1982-12-07 | Eli Lilly And Company | Vinblastine oxazolidinedione disulfides and related compounds |
| EP0233101A1 (fr) * | 1986-01-13 | 1987-08-19 | Ire-Celltarg S.A. | Dérivés de vinblastine et composition pharmaceutique les contenant |
Family Cites Families (2)
| 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 |
| IL48685A (en) * | 1975-01-09 | 1980-03-31 | Lilly Co Eli | Amides of vincadioline and vinblastine |
-
1977
- 1977-08-10 GR GR54126A patent/GR69783B/el unknown
- 1977-08-15 IL IL52731A patent/IL52731A0/xx not_active IP Right Cessation
- 1977-08-15 IE IE1700/77A patent/IE45558B1/en not_active IP Right Cessation
- 1977-08-15 CA CA284,711A patent/CA1082179A/en not_active Expired
- 1977-08-16 NZ NZ184932A patent/NZ184932A/xx unknown
- 1977-08-17 ZA ZA00774988A patent/ZA774988B/xx unknown
- 1977-08-19 AU AU28039/77A patent/AU511055B2/en not_active Expired
- 1977-09-01 PT PT66984A patent/PT66984B/pt unknown
- 1977-09-01 DE DE19772739443 patent/DE2739443A1/de active Granted
- 1977-09-01 PL PL1977200607A patent/PL104309B1/pl not_active IP Right Cessation
- 1977-09-01 AR AR269062A patent/AR226411A1/es active
- 1977-09-02 GB GB36691/77A patent/GB1586709A/en not_active Expired
- 1977-09-02 YU YU02097/77A patent/YU209777A/xx unknown
- 1977-09-02 PH PH20192A patent/PH14771A/en unknown
- 1977-09-06 NL NL7709806A patent/NL7709806A/xx not_active Application Discontinuation
- 1977-09-06 RO RO7798857A patent/RO77922A/ro unknown
- 1977-09-06 RO RO7798856A patent/RO77921A/ro unknown
- 1977-09-06 CH CH1089377A patent/CH631990A5/de not_active IP Right Cessation
- 1977-09-07 MX MX776104U patent/MX4740E/es unknown
- 1977-09-07 RO RO7791544A patent/RO72474A/ro unknown
- 1977-09-07 HU HU77EI762A patent/HU180722B/hu unknown
- 1977-09-07 AT AT644277A patent/AT360513B/de not_active IP Right Cessation
- 1977-09-07 FR FR7727080A patent/FR2364220A1/fr active Granted
- 1977-09-07 SE SE7710059A patent/SE434953B/xx not_active IP Right Cessation
- 1977-09-07 DK DK398577A patent/DK146822C/da not_active IP Right Cessation
- 1977-09-07 BE BE1008362A patent/BE858451A/xx not_active IP Right Cessation
- 1977-09-08 JP JP10834477A patent/JPS5340799A/ja active Granted
- 1977-09-08 ES ES462229A patent/ES462229A1/es not_active Expired
- 1977-09-08 DD DD7700200940A patent/DD133055A5/xx unknown
-
1979
- 1979-07-25 AR AR277455A patent/AR230642A1/es active
- 1979-07-25 AR AR277456A patent/AR231643A1/es active
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Decisions on the lapse of the protection rights |
Effective date: 20060515 |