CS211852B1 - Derivative of the 5h-izoindolo/1,2-b/3/benzazepin-5-one - Google Patents
Derivative of the 5h-izoindolo/1,2-b/3/benzazepin-5-one Download PDFInfo
- Publication number
- CS211852B1 CS211852B1 CS802885A CS288580A CS211852B1 CS 211852 B1 CS211852 B1 CS 211852B1 CS 802885 A CS802885 A CS 802885A CS 288580 A CS288580 A CS 288580A CS 211852 B1 CS211852 B1 CS 211852B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- benzazepin
- isoindolo
- derivative
- izoindolo
- formula
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- WWVGXWRJWMUFSY-UHFFFAOYSA-N 1-benzazepin-5-one Chemical compound O=C1C=CC=NC2=CC=CC=C12 WWVGXWRJWMUFSY-UHFFFAOYSA-N 0.000 claims description 2
- KPJPHPFMCOKUMW-UHFFFAOYSA-N iodomethane Chemical compound I[CH2] KPJPHPFMCOKUMW-UHFFFAOYSA-N 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AKNNEGZIBPJZJG-MSOLQXFVSA-N (-)-noscapine Chemical compound CN1CCC2=CC=3OCOC=3C(OC)=C2[C@@H]1[C@@H]1C2=CC=C(OC)C(OC)=C2C(=O)O1 AKNNEGZIBPJZJG-MSOLQXFVSA-N 0.000 description 1
- KCOKVCKMOZEQMO-UHFFFAOYSA-N 3-benzazepin-1-one Chemical compound O=C1C=NC=CC2=CC=CC=C12 KCOKVCKMOZEQMO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000008896 Opium Substances 0.000 description 1
- XXNNKVDBGXCFHP-HBFSDRIKSA-N Papaverrubine A Natural products O(C)[C@H]1O[C@@H]2[C@H](NCCc3c2cc2OCOc2c3)c2c1c1OCOc1cc2 XXNNKVDBGXCFHP-HBFSDRIKSA-N 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- AKNNEGZIBPJZJG-UHFFFAOYSA-N alpha-noscapine Natural products CN1CCC2=CC=3OCOC=3C(OC)=C2C1C1C2=CC=C(OC)C(OC)=C2C(=O)O1 AKNNEGZIBPJZJG-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- PLPRGLOFPNJOTN-UHFFFAOYSA-N narcotine Natural products COc1ccc2C(OC(=O)c2c1OC)C3Cc4c(CN3C)cc5OCOc5c4OC PLPRGLOFPNJOTN-UHFFFAOYSA-N 0.000 description 1
- 229960001027 opium Drugs 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
POPIS VYNÁLEZU
K AUTORSKÉMU OSVEDČENIU 211 852 (11) (Bl) ČESKOSLOVENSKÁSOCIALISTICKÁREPUBLIKA( 19 )
(61) (23) Výstavná priorita(22) Přihlášené 06 04 79(21) PV 2885-80 (51) IntCI? C 07 D 491/147// C 07 D 223/16 A 61 K 31/33
ÚŘAD PRO VYNÁLEZYA OBJEVY (40) Zverejnené 31 07 81(45) Vydané n g3 (75)
Autor vynálezu PEOKSA BOHUMIL ing.CSc., HLOHOVECV01ICKÝ ZDENO ďr.ing.CSc.
FUŠKA JÁN ing.CSc., BRATISLAVA (54) Derivát 5H-izoindolo£l,2-b| [3] benzazepin-5-ónu
vynález sa tiež týká spSsobu výroby derivátu vzorca I. Látka vzorca I, ktorá doteraz nebole opísaná, je cennou, farmakologicky významnou látkoua potenciálnymi cytotoxickými vlastnosíami.
Zlúčeniny základného skeletu 7,S-dihydro-5H-izoindolo-fl,2-b] [3] benzazepin-5-ónu bolí zís-kané napr. oxidáciou papaverrubínu A CWalterová, Šantavý, Coll.Czech.Chem.Commun. 33, 1623,1968), izoláciou zo zmeai vedíajSích opiových alkaloidov (Trojánek a sp. Coll.Czech.Chem.Commun40, 681, 1975), alebo syntézou vychádzajúcou z narkotínu (Teitel a sp. Can.J.Chem. 50, 2022.1972). Látky uvedeného základného skeletu, ale s dvojitou vazbou v polohe 7t8 sa doteraz nepo- 211 852
Claims (2)
1. Derivát 5H-izoindolo[l,2-bJy3jbenzazepin-5-ónu vzorce I
(I) ty o 0
2. SpSaob výroby derivátu JH-izoindolo^l^-b^/S/^enzazepin-S-ónu vzorca I, pódia bodu 1,vyznačujúci aa tým, že sa najprv 7,8-dihydro-3,4,12-trimetoxy-7-dimetylamíno-10,ll-metyléndioxy-*-5H-izoindolo£l,2-bj£}Jbenzazepin-5-ón prevádza posobením metyljodidu na jódmetylát, ktorý aapotom rozkládá účinkom roztoku hydroxidu draselného.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS802885A CS211852B1 (en) | 1979-04-06 | 1980-04-24 | Derivative of the 5h-izoindolo/1,2-b/3/benzazepin-5-one |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS235479A CS211851B1 (en) | 1979-04-06 | 1979-04-06 | Derivatives of the 7,8 dihydro-5h-izoindolo-/1,2-b/3/benzazepine-5- |
| CS802885A CS211852B1 (en) | 1979-04-06 | 1980-04-24 | Derivative of the 5h-izoindolo/1,2-b/3/benzazepin-5-one |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS211852B1 true CS211852B1 (en) | 1982-02-26 |
Family
ID=5360441
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS235479A CS211851B1 (en) | 1979-04-06 | 1979-04-06 | Derivatives of the 7,8 dihydro-5h-izoindolo-/1,2-b/3/benzazepine-5- |
| CS802885A CS211852B1 (en) | 1979-04-06 | 1980-04-24 | Derivative of the 5h-izoindolo/1,2-b/3/benzazepin-5-one |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS235479A CS211851B1 (en) | 1979-04-06 | 1979-04-06 | Derivatives of the 7,8 dihydro-5h-izoindolo-/1,2-b/3/benzazepine-5- |
Country Status (1)
| Country | Link |
|---|---|
| CS (2) | CS211851B1 (cs) |
-
1979
- 1979-04-06 CS CS235479A patent/CS211851B1/cs unknown
-
1980
- 1980-04-24 CS CS802885A patent/CS211852B1/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS211851B1 (en) | 1982-02-26 |
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