IL43283A - 7h-indolo(2,3-c) quinoline derivatives,their preparation and pharmaceutical compositions containing them - Google Patents
7h-indolo(2,3-c) quinoline derivatives,their preparation and pharmaceutical compositions containing themInfo
- Publication number
- IL43283A IL43283A IL43283A IL4328373A IL43283A IL 43283 A IL43283 A IL 43283A IL 43283 A IL43283 A IL 43283A IL 4328373 A IL4328373 A IL 4328373A IL 43283 A IL43283 A IL 43283A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- compound
- hydrogen
- lower alkyl
- compounds
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Claims (25)
1. Compounds of the formula wherein and R^ are hydrogen, lower alkyl, lower alkenyl or a radical of the formula -A-N' . ^R7 or -A-O-B, wherein A is a straight chain lower alkylene of _1, 2 or 3 carbon atoms, Rg and R^ are hydrogen or lower alkyl , or taken together with the nitrogen atom, are a saturated heterocyclic group of 5 or 6 members , which may contain one oxygen atom and B is hydrogen or lower alkyl; nitro; as well as -Ν-oxides of these compounds and addition salts of these compounds with acids. 43283/
2. Compounds according to Claim 1 of the formula wherein R2 and R^ are hydrogen, lower alkyl or a radical of the formula -A'- Λ R- or -A'-O-B, wherein A' is a straight chain lower alkylene of 2 or 3 carbon . atoms , R, and R_ are hydrogen, lower alkyl, or taken b together with the nitrogen atom form a morpholino group,- and. B is hydrogen- or lower - R. lower alkyl, lower alkoxy or nitro; as addition salts of these compounds with acids.
3. Compounds according to Claim 1 of the formula 43283/2 wherein R' and R'4, independently, are hydrogen, ^R6 lower alkyl, lower alkenyl or -A-N , wherein ^R,7 A is a straight chain lower alkylene of 1, 2 or 3 carbon atoms, and Rg and R^ , independently are* "hydroge --or-i.
4. Owe"r-~ai-k- l-y-' ■ or taken together with the nitrogen agom, are a saturated heterocyclic group of 5 or 6 members, which may contain one oxygen atom; and.
5. R'g is nitro, halogen, preferably .chlorine; R' - is a radical (2-Dimethylaminoethyl) -7H-indolo [2 , 3-c] quinolin (2-diethylaminoethyl) -7H-indolo [2 , 3-c] quinolin-
6. Compounds of the formula I'a in Claim 3, whe R-. is chloro.
7. 10-Chloro-5- (2-dimethylaminoethyl) -7H-indolo-[2 , 3-c] quinolin-6 (5H) -one.
8. lO-Chloro-5- (2-methylaminoethyl) -7H-indolo [2 , 3-c^-quinolin-6 (5H) -one.
9. lO-Chloro-5- (2-aminoethyl) -7H-indolo [2 ,3-c] -quinolin-6 (5H) -one.
10. lO-Chloro-7- (2-dimethylaminoe hyl) -7H-indolo-[2 , 3-c] quinolin-6 (5H) -one.
11. Compounds of formula I in Claim 1, substantially ' as described herein with, reference to the Examples."
12. A process for the preparation of compounds of formula'-3 in -Oiain iw-as' we ^ as ¾)- -oxi'des Ό-f «thes"e5>-compQunds tua, and addition salts of these compounds with acids, characterized in that a compound of the formula s re that in the production of a compound of the -formula wherein R^ and/or R^ are/is lower alkyl, lower alkenyl or a radical of the formula -A-N or 'R7 -A-O-B, wherein A, B, R, and R7 are as an obtained compound of the formula wherein one of and R24 is hydrogen and the other is a radical of the formula -Α-Ι and R^, R^ , A, B, Rg and R^ are as above, or a compound of the formula wherein R"2 and R"1^ are hydrogen, lower alkyl or lower alkenyl, provided that at least one of R"2 or R'"4 is hydrogen; and R.^ and R5 are as above , is reacted with a compound of the formula X - W wherein X is a halogen atom and W is lower alkyl, lower alkenyl or a radical • ■ of the formula -A-N or -A-O-B, wherein A, B, Rg and are as above, that in the prpduction_of a compound of the formula I, vherein :R1 and/or R^ are/is halogen or nitro, an obtained compound of the formula I, wherein -j^ and/or ^ is hydrogen is halogenated or n trated, that, in the production of a compound of the formula I, wherein R, R. are/is aminonethyl, in a compound of the formula 43283/2 wherein R" and Rm are hydrogen, lower alkyl, lower alkenyl or cyano, provided that at least one of R" and R"1 is cyano; and ^ and R5 are as above , the cyano. roup is reduced to the aminocethyl group, that in the production of a compound of the formula wherein P^, R2 and are as above, a ~Gompound-of -the..-f.ornula wherein R^, and R5 are as a¾ovef is c'yclized, and that, if desired, a compound of the formula is converted into an
13. · . Process according to Claim 12 for the preparation of compounds' of the'-'formula * ' " wherein R„ and R, are hydrogen, lower alkyl or a radical of the -A'-O-B, wherein A' is a straight chain lower alkylene of 2 or 3 carbon- atoms, R, and R-, are hydrogen, lower alkyl, or taken together with the nitrogen atom, form a morpholino group, and B is hydrogen, or lower alkyl; 43283/2 provided that at least one of R~ or R. is a radical of the formula -A'-N or -A'-O-B; R1 and R5 are hydrogen, halogen, lower alkyl, lower alkoxy, or n tro; and of addition salts of these compounds with acids, characterized in that a compound of the formula wherein Y is a leaving group and R^, R2J R, and Rc are as above, 4 is reacted with a strong base, that in the Oroduction of a compound of the formula 43283/2 , and R^ an R,- are as a ove, an obtaine wherein one of R22 and 24 is hydrogen an the other is a radical of the formula -A' or. -A'-O-B, R24 is hydrogen ~ and R±t R5, A', B, Rg and R? are as above, compound of the formula 43283/2 wherein R"2 and R'"4 are hydrogen or lower alkyl, provided that at least one of R'^ or R'"4 is hydrogen; and R.^ and 5 are as above , is reacted with a compound of the formula X - W wherein X is a halogen atom and W is lower alkyl or a radical of the formula -A-H or -A-O-B, wherein A, B, and are as above, that in the production of a compound of the formula I, wherein R^ and/or R^ are/is halogen or nitro. an obtained compound o"f the 'for uTa ~I, therein "is J hydrogen, is halogenated or nitrated, that in the production of a compound of the formula wherein R, , R and Rc are as above, 43283/2 ompound of the formula wherein ^, R2 and ^ are as. above, is cyclized, and that, if desired, a compound of the formula I is converted into an addition salt with an acid.
14. Process as claimed in _Claim_12..or .2.3 -for— e--.^-preparation of a compound of the formula I according to Claim 12 or 13, characterized in that, a compound of the formula II is reacted with a strong base in the presence an inert solvent at a temperature in the range of from about 100° to about 200°C.
15. Process as claimed in any one of Claims 12-14 for the preparation of compounds of the formula 43283/2 wherein R' ~ and R'4, independently, are hydrogen, carbon atoms and Rg and R^ , independently, are hydrogen or lower alkyl, or taken together with the nitrogen atom, are a saturated heterocyclic group of 5 or 6 members, which may contain an oxygen atom, and R'.. is nitro, halogen, preferably chlorine> provided that one of R' or R' . is a radical of the formula or addition salts thereof with acids, characterized in that a compound of the formula above. is utilized as starting material of the formula II" that a compound of the formula 43283/2 wherein R'^^'and E"^ are hydrogen, lower alkyl or lower alkenyl, provided that at least one of R"21 or R"^ is hydrogen, and Rj- is as above , is utilized as starting material of the formula II1 or in that a compound ,of .the,.f rmula,„„ R wherein 2, R^, R^ and Y are as above, s utilized as starting material of the formula II 43283/3 . τ
16. Process as claimed in any one of claims 12 to 15 for the^ reparatiOii-' f 5-(2-dImekhy a¾lnoeth'y^ [2 , 3-c] - quinolin-6 (5H)-one , characterized in that 3-azido-l-(2- \^ dimethylaminoethyl)-4-phenylcarbostyril is utilized as starting . material of the formula II" .
17. Process as claimed in any one of claims 12 to 15 for the preparation of 7-(2-diethylaminoethyl)-7H-indolo[ 2, 3-c]-quinolin-6(5H)-one, characterized in that 7H-indolo[2,3-c]-quinolin-6 (5H)-one is utilized as starting material of the formula II ' .
18. Process according to claim 12 : or 15 for the preparation of a compound of the formula I'a, wherein is chloro, characterized in that a compound of the formula II, II1 or II" , wherein R<- is chloro is utilized as starting material. 43283/2
19. Process as claimed in claim 12 or 18 for the preparation of lO-chloro-5-( 2-dimeth laminoethyl)-7H-indolo[ 2 ,3-c ] quinolin-6(5H)-onef characterized in that 5-chloro-N- ( 2-dime¾iylamino-ethyl)-3-(2-flu0rophenyl)-ind(i'le-2-carboxamide is utilized as starting material of the formula II. 1
20. Process as claimed in claim 12 or 18 for the preparation of 10-chloro-5-(2-methylaminoethyl)-7H-indolo[2,3-c]-quinolin-6(5H)-one, characterized in that 5-chloro-3-^-fluorophenyl)^-(2-methylaminoethyl)-indole-2-carboxamid is utilized as starting material of the formula II.
21. Process as claimed in claim 12 or 18 for the preparation of 10-chloro-5-(2-aminoethyl)-7H-indolo[2,3-c]quinolin-6(5H)-one, characterized in that N-(2-aminoethyl)-5-chloro-3-(2-fluorophenyl)-indole-2-carboxamide is utilized as starting material of the formula II.
22. Process as claimed of claim 12 or 18 for the prepara-tion of 10-chloro-7-(2-dimethylaminoethyl)-7H-indolo[2f3-c]-quinolin-6(5H)-one, characterized in that 10-chloro-7H-indolo [2,3-c]quinolin-6(5H)-one is utilized as starting material of. the formula II 1. 43283/2
23. Process for the preparation of compounds of the formula I in Claim 1 as hereinbefore particularly described, especially with reference to the foregoing Examples.
24. Compounds of formula I in Claim 1 as well as ωι-Κ-oxides: of these compounds and addition salts of these compounds with acids, when prepared by a process according to any of Claims 12-23.
25. Compositions having antitumor properties, containing a compound of the formula I in Claim 1 or an ta~N-G¾ide of suc a compound or an addition salt of such a compound with an acid and a carrier. Applicants LD CQHN AND VK
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29219372A | 1972-09-25 | 1972-09-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL43283A0 IL43283A0 (en) | 1975-08-31 |
| IL43283A true IL43283A (en) | 1976-12-31 |
Family
ID=23123617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL43283A IL43283A (en) | 1972-09-25 | 1973-09-21 | 7h-indolo(2,3-c) quinoline derivatives,their preparation and pharmaceutical compositions containing them |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS4969698A (en) |
| AR (1) | AR205437A1 (en) |
| AT (1) | AT340425B (en) |
| BE (1) | BE805199A (en) |
| CH (1) | CH587274A5 (en) |
| DD (1) | DD109388A5 (en) |
| DE (1) | DE2348149A1 (en) |
| ES (1) | ES419019A1 (en) |
| FR (1) | FR2200004B1 (en) |
| GB (1) | GB1400934A (en) |
| HU (1) | HU168788B (en) |
| IE (1) | IE38331B1 (en) |
| IL (1) | IL43283A (en) |
| LU (1) | LU68486A1 (en) |
| NL (1) | NL7313186A (en) |
| SU (1) | SU525428A3 (en) |
| ZA (1) | ZA735679B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004108671A1 (en) * | 2003-06-06 | 2004-12-16 | Suven Life Sciences Limited | Substituted indoles with serotonin receptor affinity, process for their preparation and pharmaceutical compositions containing them |
| US20050089936A1 (en) * | 2003-10-23 | 2005-04-28 | Jianping Cai | Combinatorial library of 3-aryl-1H-indole-2-carboxylic acid amides |
| ITMI20040874A1 (en) * | 2004-04-30 | 2004-07-30 | Ist Naz Stud Cura Dei Tumori | INDOLIC AND AZAINDOLIC DERIVATIVES WITH ANTI-TUMORAL ACTION |
| FR2887881B1 (en) * | 2005-07-01 | 2009-10-09 | Pierre Fabre Medicament Sa | PROTEIN INHIBITORS KINASES |
| JP5496877B2 (en) | 2007-04-16 | 2014-05-21 | アッヴィ・インコーポレイテッド | 7-substituted indole Mcl-1 inhibitors |
| CN114605407B (en) * | 2022-03-14 | 2024-06-04 | 澳门科技大学 | Indoloquinolinone compound and synthetic method and application thereof |
-
1973
- 1973-01-01 AR AR250218A patent/AR205437A1/en active
- 1973-08-20 ZA ZA735679A patent/ZA735679B/en unknown
- 1973-08-30 CH CH1244073A patent/CH587274A5/xx not_active IP Right Cessation
- 1973-09-21 IL IL43283A patent/IL43283A/en unknown
- 1973-09-21 JP JP48106066A patent/JPS4969698A/ja active Pending
- 1973-09-21 IE IE1693/73A patent/IE38331B1/en unknown
- 1973-09-24 GB GB4469173A patent/GB1400934A/en not_active Expired
- 1973-09-24 AT AT818873A patent/AT340425B/en not_active IP Right Cessation
- 1973-09-24 LU LU68486A patent/LU68486A1/xx unknown
- 1973-09-24 DD DD173636A patent/DD109388A5/xx unknown
- 1973-09-24 BE BE135940A patent/BE805199A/en unknown
- 1973-09-24 FR FR7334085A patent/FR2200004B1/fr not_active Expired
- 1973-09-24 SU SU1959333A patent/SU525428A3/en active
- 1973-09-25 NL NL7313186A patent/NL7313186A/xx not_active Application Discontinuation
- 1973-09-25 DE DE19732348149 patent/DE2348149A1/en active Pending
- 1973-09-25 HU HUHO1616A patent/HU168788B/hu unknown
-
1974
- 1974-09-24 ES ES419019A patent/ES419019A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1400934A (en) | 1975-07-16 |
| ZA735679B (en) | 1974-07-31 |
| DE2348149A1 (en) | 1974-04-04 |
| JPS4969698A (en) | 1974-07-05 |
| AR205437A1 (en) | 1976-05-07 |
| IE38331B1 (en) | 1978-02-15 |
| IE38331L (en) | 1974-03-25 |
| AT340425B (en) | 1977-12-12 |
| ATA818873A (en) | 1977-04-15 |
| CH587274A5 (en) | 1977-04-29 |
| BE805199A (en) | 1974-03-25 |
| DD109388A5 (en) | 1974-11-05 |
| IL43283A0 (en) | 1975-08-31 |
| LU68486A1 (en) | 1975-06-16 |
| ES419019A1 (en) | 1976-06-16 |
| HU168788B (en) | 1976-07-28 |
| NL7313186A (en) | 1974-03-27 |
| AU6062073A (en) | 1975-03-27 |
| FR2200004B1 (en) | 1976-07-02 |
| SU525428A3 (en) | 1976-08-15 |
| FR2200004A1 (en) | 1974-04-19 |
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