SE464523B - 8,13-dioxobens(5,6)-isoindolo(2,1,6)isokinolinderivat och ett foerfarande foer framstaellning av detta - Google Patents
8,13-dioxobens(5,6)-isoindolo(2,1,6)isokinolinderivat och ett foerfarande foer framstaellning av dettaInfo
- Publication number
- SE464523B SE464523B SE8904107A SE8904107A SE464523B SE 464523 B SE464523 B SE 464523B SE 8904107 A SE8904107 A SE 8904107A SE 8904107 A SE8904107 A SE 8904107A SE 464523 B SE464523 B SE 464523B
- Authority
- SE
- Sweden
- Prior art keywords
- hydroxy
- methyl
- formula
- compound
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 15
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- KQPYUDDGWXQXHS-UHFFFAOYSA-N juglone Chemical compound O=C1C=CC(=O)C2=C1C=CC=C2O KQPYUDDGWXQXHS-UHFFFAOYSA-N 0.000 claims description 8
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- ZEMNVPLWDUWKEG-UHFFFAOYSA-N 3,4-dihydro-1h-isoquinoline-2-carbaldehyde Chemical compound C1=CC=C2CN(C=O)CCC2=C1 ZEMNVPLWDUWKEG-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- -1 methylenedioxy group Chemical group 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- QKDLQFSLLCQTOH-UHFFFAOYSA-N Trichodonin Natural products C1C(O)C2C3(COC(=O)C)C(C=O)C(C)(C)CCC3OC(=O)C22C(=O)C(=C)C1C2 QKDLQFSLLCQTOH-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- SGXDXUYKISDCAZ-UHFFFAOYSA-N N,N-diethylglycine Chemical compound CCN(CC)CC(O)=O SGXDXUYKISDCAZ-UHFFFAOYSA-N 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- JDNTWHVOXJZDSN-UHFFFAOYSA-N iodoacetic acid Chemical compound OC(=O)CI JDNTWHVOXJZDSN-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
464 523 Rs | I Rz Q O O \_// \_/ \ / \_// \_ 1 |. l I | (1) R3/'\\ /'\ / \ // \_/ \\_/ “M5 l ---JJ H 2.- »__-o O (vari: Rl är en väteatom eller en metylgrupp; R2 är en väteatom eller en hydroxyl-, Cl_4-alkoxi- eller C2_4- alkanoyloxigrupp; R3 är en väteatom eller (när R2 har annan betydelse än en väteatom) eventuellt en hydroxi-, Cl_4-alkoxi- eller C2_4-al- kanoyloxigrupp, eller R2 och R3 tillsammans är en metylendi- oxigrupp; R är en väteatom eller en halogenatom eller en metylgrupp; R5 och R6 är vardera en väteatom eller en grupp -OCOCH NR7R8 8 2 /vari R7 och R , som kan vara lika eller olika, vardera är en väteatom eller en C3_7-cykloalkylgrupp eller en rak eller gre- nad Cl_4-alkylgrppâ, eventuellt substituerad med en hydroxyl- grupp, eller -NR R bildar en mättad heterocyklisk aminogrupp, som har 5-7 ringmedlemmar och eventuellt i ringen innehåller en syre- eller svavelatom eller en grupp -NH- eller -N(R)-, vari R är en Ci_4-alkylgrupp eventuellt substituerad med en 6 hydroxylgrupp/ med det förbehållet att när en av R5 och R är 2NR7R8 och salter därav. Det anges däri att sådana föreningar uppvisar speciellt en väteatom är den andra en grupp OCOCH intressanta farmakologiska egenskaper, särskilt anti-cancer- aktivitet.
Enligt en ytterligare aspekt av föreliggande uppfinning till- handahålles ett förfarande för framställning av föreningarna med formeln (2), vilket innefattar att man kondenserar 5-hyd- roxi-1,4-naftokinon med N-formyl-l,2,3,4-tetrahydroisokinolin- 9 -4-metyl-3-karboxylsyra i närvaro av en alkansyraanhydrid, såsom ättiksyraanhyarid, vid förhöja temperatur, t.ex. 1oo°c. “ Både 5-hydroxi-1,4-naftokinon och N-formyl-1,2,3,4-tetrahydro- isokinolin-4-metyl-3-karboxylsyra är kända föreningar. 3 464 523 Följande exempel åskådliggör uppfinningen. Samtliga tempera- turer avser °C.
Exempel l 5,8,l3,l4-tetrahydro-(9- och l2-hydroxi)-14-metylbens/5,6/iso- indol/2,l/isokinolin-8,13-dion Ättiksyraanhydrid (160 ml) sattes till en blandning av N-for- myl-l,2,3,4-tetrahydroisokinolin-4-metyl-3-karboxylsyra (20 g) och 5-hydroxi-1,4-naftokinon (3l,78 g). Reaktionsblandningen upphettades vid lO0° en halv timme och fick därefter kallna över natten (16 timmar) följt av ytterligare kylning i en timme. En fällning bildades som filtrerades och genom tunn- skiktskromatografi visades vara en blandning av 9-hydroxi- och 12-hydroxiisomererna. Isomererna separerades genom kromatogra- fi på silikagel (med användning av diklormetan som lösnings- medel). Från tidigare fraktioner erhölls 9-hydroxiisomeren av titelföreningen, vilken var minimikomponenten. Maximikomponen- ten, 12-hydroxiisomeren av titelföreningen, samlades från senare fraktioner,,lmax 243 nm, Eâ ll03, 397 nm, Eå 381.
Exempel 2 Klorättiksyra, /5,8,l3,14-tetrahydro-14-metyl-8,l3-dioxi- bens/5,6/isoindol/2,l-b/isokinolin-12-yl/-ester Natriumhydrid (60 % dispersion) tvättades med petroleumeter (kokpunkt 40-60°) under kväve, tetrahydrofuran (10 ml) till- sattes följt av 12-hydroxiisomeren från exempel l (0,5 g) upp- löst i tetrahydrofuran (10 ml). Reaktionsblandningen omrör- des i 10 minuter och kloracetylklorid (0,l5 ml) tillsattes.
Blandningen omrördes därefter i ytterligare 10 minuter. 2-pro- panol (l ml) tillsattes följt av en liten mängd vatten, som tillsattes droppvis. Blandningen hälldes på is och extrahera- des med etylacetat (3 gånger). Kristallisation skedde vid in- dunstning till liten volym och gav titelföreningen (168 mg), smältpunkt 218-222° (sönderdelning). 464 523 Exempel 3 Jodättiksyra, /5,8,13,14-tetrahydro-14-metyl-8,l3-dioxobens- /5,6/isoindol/2,l-b/isokinolin-12-yl/-ester Föreningen enligt exempel 2 (2,45 g) löstes i aceton (200 ml) och natriumjodid (6 g) tillsattes. Reaktionsblandningen omrör- des i 18 timmar vid rumstemperatur, indunstades därefter till torrhet och återlöstes i kloroform. Det oorganiska materialet avlägsnades genom filtrering och lösningen indunstades där- efter till torrhet. Kristallisation ur diklormetan-petroleum- eter (kokpunkt 40-60°) gav titelföreningen, smältpunkt 205- 2l0° (sönderdelning).
Exempel 4 (Dietylamino)ättiksyra, /5,8,l3,14-tetrahydro-l4-metyl-8,13- dioxobens/5,6/isoindol/2,l-b/isokinolin-l2-yl/-ester Föreningen från exempel 3 (lg) och dietylamin (O,42 ml) i aceton (lO0 ml) omrördes vid rumstemperatur i l5 minuter. Den erhållna lösningen indunstades sedan till torrhet under redu- cerat tryck och gav en olja, vilken efter blandning med etyl- acetat gav en fast substans som tvättades med vatten och tor- kades. Kristallisation ur metylacetat gav titelföreningen (410 mg), smautpunkt 19o-193°.;(max 243 nm, så 981, ,g(cnc13) 1,50 (14-CH3), 3,97, 4,07 (CH2 av ester), 1,33 (CH3 av etyl), 2,99 (CH2 av etyl).
Exempel 5 (Dietylamino)ättiksyra, /5,8,13,14-tetrahydro-14-metyl-8,l3- dioxobens/5,6/isoindol/2,l-b/isokinolin-12-yl/ester, hydroklo- šië Föreningen från exempel 4 (375 mg), 0,lN saltsyra (20 ml) och vatten (375 ml) omrördes vid rumstemperatur i 30 minuter, filtrerades och frystorkades och gav titelföreningen (40 mg), .Å max 244 nm, 481 5 ester), 1,71 (CH3 av etyl), 3,78 (CH2 av etyl). Ü»
Claims (6)
1. l. Föreningar med formeln (2) ?H3 9 TIO _//'\_/'\ /°\_//°\_ g 1 u I I n (2) '\\_/°\_/ \_//'\_/'\\_/° 'älv Zl! vari en av R9 och Rlo är en hydroxigrupp och den andra är en väteatom.
2. En förening med formeln (2) enligt patentkravet l, nämligen 5,8,l3,l4-tetrahydro-9-hydroxi-14-metylbens/5,6/isoindol/2,l-b/ -isokinolin-8,13-dion.
3. En förening med formeln (2) enligt patentkravet l, nämligen 5,8,13,14-tetrahydro-12-hydroxi-14-metylbens/5,6/isoindol/2,l- b/isokinolin-8,13-dion.
4. Ett förfarande för framställning av en förening med formeln (2) enligt patentkravet l, k ä n n e t e c k n a t därav, att man kondenserar 5-hydroxi-1,4-naftokinon med N-formyl-l,2,3,4- tetrahydroisokinolin-4-mety1-3-karboxylsyra i närvaro av en alkansyraanhydrid.
5. Förfarande enligt patentkravet 4, k ä n n e t e c k n a t därav, att nämnda alkansyraanhydrid är ättiksyraanhydrid.
6. Förfarande enligt patentkravet 4, k ä n n e t e c k n a t därav, att produkterna enligt patentkraven 2 och 3 därefter avskiljes.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB858513460A GB8513460D0 (en) | 1985-05-29 | 1985-05-29 | Chemical compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8904107D0 SE8904107D0 (sv) | 1989-12-05 |
| SE464523B true SE464523B (sv) | 1991-05-06 |
Family
ID=10579796
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8602434A SE8602434L (sv) | 1985-05-29 | 1986-05-28 | Kemiska foreningar |
| SE8904107A SE464523B (sv) | 1985-05-29 | 1989-12-05 | 8,13-dioxobens(5,6)-isoindolo(2,1,6)isokinolinderivat och ett foerfarande foer framstaellning av detta |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8602434A SE8602434L (sv) | 1985-05-29 | 1986-05-28 | Kemiska foreningar |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4900737A (sv) |
| JP (1) | JPS6212778A (sv) |
| KR (1) | KR860009015A (sv) |
| BE (1) | BE904835A (sv) |
| CH (2) | CH668596A5 (sv) |
| DE (1) | DE3617938A1 (sv) |
| DK (1) | DK246986A (sv) |
| ES (2) | ES8800942A1 (sv) |
| FI (1) | FI862277A7 (sv) |
| FR (1) | FR2584072B1 (sv) |
| GB (2) | GB8513460D0 (sv) |
| IT (1) | IT1191931B (sv) |
| NL (1) | NL8601381A (sv) |
| NO (1) | NO862120L (sv) |
| NZ (1) | NZ216338A (sv) |
| PH (2) | PH24002A (sv) |
| SE (2) | SE8602434L (sv) |
| ZA (1) | ZA864015B (sv) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK616087A (da) * | 1986-11-27 | 1988-05-28 | Glaxo Group Ltd | Isoquinolinderivater og farmaceutiske praeparater indeholdende dem |
| GB8800312D0 (en) * | 1988-01-07 | 1988-02-10 | Glaxo Group Ltd | Process |
| FR2801309B1 (fr) * | 1999-11-18 | 2002-01-04 | Adir | Nouveaux composes analogues de la camptothecine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| CN114805204B (zh) * | 2022-04-01 | 2023-09-15 | 云南师范大学 | 一种制备4-碘异喹啉-1(2h)-酮类化合物的方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4029659A (en) * | 1971-03-29 | 1977-06-14 | Omnium Chimique Societe Anonyme | N-disubstituted aminoethyl esters of 11-methoxy-raubasinic acid |
| US3894029A (en) * | 1971-08-26 | 1975-07-08 | Basf Ag | Production of camptothecin and camptothecin-like compounds |
| US3903276A (en) * | 1972-03-20 | 1975-09-02 | American Home Prod | N-carboxymethyl-N-substituted glycinate esters of 3-hydroxy-1,4-benzodiazepin-2-ones for inducing a calming effect |
| US4301285A (en) * | 1980-10-02 | 1981-11-17 | American Home Products Corporation | Sydnonimine CNS stimulants |
| NL8202626A (nl) * | 1982-06-29 | 1984-01-16 | Stichting Rega V Z W | Derivaten van 9-(2-hydroxyethoxymethyl)guanine. |
| DK158666C (da) * | 1982-11-04 | 1990-11-19 | Glaxo Group Ltd | Analogifremgangsmaade til fremstilling af 5,14-dihydrobenz-oe5,6aa-isoindolooe2,1-baa-isoquinolin-8,13-dion |
| DK160991C (da) * | 1984-05-03 | 1991-11-11 | Glaxo Group Ltd | 5,14-dihydrobenzoe5,6aaisoindolooe2,1-baaisoquinolin-8,13-dionderivater, fremgangsmaade til fremstilling deraf og farmaceutisk praeparat indeholdende en saadan forbindelse |
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1985
- 1985-05-29 GB GB858513460A patent/GB8513460D0/en active Pending
-
1986
- 1986-05-27 DK DK246986A patent/DK246986A/da not_active Application Discontinuation
- 1986-05-28 CH CH2151/86A patent/CH668596A5/de not_active IP Right Cessation
- 1986-05-28 SE SE8602434A patent/SE8602434L/sv unknown
- 1986-05-28 KR KR1019860004188A patent/KR860009015A/ko not_active Withdrawn
- 1986-05-28 BE BE0/216713A patent/BE904835A/fr not_active IP Right Cessation
- 1986-05-28 DE DE19863617938 patent/DE3617938A1/de not_active Withdrawn
- 1986-05-28 ES ES555407A patent/ES8800942A1/es not_active Expired
- 1986-05-28 IT IT48070/86A patent/IT1191931B/it active
- 1986-05-28 NO NO862120A patent/NO862120L/no unknown
- 1986-05-28 GB GB8612950A patent/GB2175587B/en not_active Expired
- 1986-05-28 NZ NZ216338A patent/NZ216338A/xx unknown
- 1986-05-29 PH PH33829A patent/PH24002A/en unknown
- 1986-05-29 ZA ZA864015A patent/ZA864015B/xx unknown
- 1986-05-29 NL NL8601381A patent/NL8601381A/nl not_active Application Discontinuation
- 1986-05-29 FI FI862277A patent/FI862277A7/fi not_active Application Discontinuation
- 1986-05-29 JP JP61122395A patent/JPS6212778A/ja active Pending
- 1986-05-29 FR FR868607726A patent/FR2584072B1/fr not_active Expired - Fee Related
-
1987
- 1987-08-31 ES ES557703A patent/ES8801212A1/es not_active Expired
- 1987-12-02 PH PH36162A patent/PH24375A/en unknown
-
1988
- 1988-05-28 CH CH2310/88A patent/CH671959A5/de not_active IP Right Cessation
- 1988-09-28 US US07/250,216 patent/US4900737A/en not_active Expired - Fee Related
-
1989
- 1989-12-05 SE SE8904107A patent/SE464523B/sv not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2584072B1 (fr) | 1991-04-19 |
| CH668596A5 (de) | 1989-01-13 |
| IT8648070A0 (it) | 1986-05-28 |
| FI862277A7 (fi) | 1986-11-30 |
| FI862277A0 (fi) | 1986-05-29 |
| FR2584072A1 (fr) | 1987-01-02 |
| CH671959A5 (sv) | 1989-10-13 |
| GB8513460D0 (en) | 1985-07-03 |
| ES8801212A1 (es) | 1988-01-01 |
| IT1191931B (it) | 1988-03-31 |
| GB8612950D0 (en) | 1986-07-02 |
| US4900737A (en) | 1990-02-13 |
| ES557703A0 (es) | 1988-01-01 |
| NL8601381A (nl) | 1986-12-16 |
| SE8602434D0 (sv) | 1986-05-28 |
| BE904835A (fr) | 1986-11-28 |
| NZ216338A (en) | 1989-03-29 |
| NO862120L (no) | 1986-12-01 |
| DK246986D0 (da) | 1986-05-27 |
| SE8602434L (sv) | 1986-11-30 |
| GB2175587A (en) | 1986-12-03 |
| GB2175587B (en) | 1989-10-11 |
| DK246986A (da) | 1986-11-30 |
| ES555407A0 (es) | 1987-12-01 |
| ZA864015B (en) | 1988-01-27 |
| JPS6212778A (ja) | 1987-01-21 |
| DE3617938A1 (de) | 1986-12-04 |
| PH24375A (en) | 1990-06-13 |
| SE8904107D0 (sv) | 1989-12-05 |
| KR860009015A (ko) | 1986-12-19 |
| AU5807386A (en) | 1986-12-04 |
| PH24002A (en) | 1990-02-09 |
| AU591905B2 (en) | 1989-12-21 |
| ES8800942A1 (es) | 1987-12-01 |
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