CA1074305A - Amino-substituted tetracyclic compounds - Google Patents
Amino-substituted tetracyclic compoundsInfo
- Publication number
- CA1074305A CA1074305A CA318,926A CA318926A CA1074305A CA 1074305 A CA1074305 A CA 1074305A CA 318926 A CA318926 A CA 318926A CA 1074305 A CA1074305 A CA 1074305A
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- Canada
- Prior art keywords
- keto
- tribenzo
- tetrahydro
- methyl
- oxepine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Abstract
ABSTRACT OF THE DISCLOSURE
This invention relates to a process for the preparation of compounds of the general formula:
II
in which X represents oxygen, sulphur, the group or the group -CR8R9-, R1, R2, R3 and R4 represent hydrogen, hydroxy, halogen, alkyl (1-6 C) alkoxy (1-6 C), or trifluoromethyl.
R7 stands for hydrogen or alkyl (1-4 C), and R8, R9 stand for hydrogen or methyl, characterized in that a compound of the general formula:
III
is condensed with vinylmethylketone
This invention relates to a process for the preparation of compounds of the general formula:
II
in which X represents oxygen, sulphur, the group or the group -CR8R9-, R1, R2, R3 and R4 represent hydrogen, hydroxy, halogen, alkyl (1-6 C) alkoxy (1-6 C), or trifluoromethyl.
R7 stands for hydrogen or alkyl (1-4 C), and R8, R9 stand for hydrogen or methyl, characterized in that a compound of the general formula:
III
is condensed with vinylmethylketone
Description
3fJ . ~
This application is a divisional of our copending Canadian Patent Application Serial No. 199,996 filed l~ay 15, 1974.
The present invention relates to certain components useful in the preparation Ofnovelbiologically active aminosubsti~uted tetracyclic compounds and to processes for the preparation thereof.
In our copending Canadian application number 199,996, filed May 15, 1974 certain compounds are disclosed which possess valuable C.N.S. activities, but at the same time exhibited exceedingly low toxicity.
These compounds are of the general formula I:
; n ~ ~ ' I
as well as the pharmaceutically acceptable salts thereof, in which X stands for oxygen, sulphur, the group ~ NR7 or the group CR8Rg-;
Rl, R2, R3 and R4 represent hydrogen, hydroxy, halogen, alkyl 6 C), alkoxy (1-6 C), ~ ;lthio (1 6 C~
or trifluoromethyl;
R5 and R6 represent hydrogen, alkyl (1-6 C), aralkyl (7-10 C) or, together in combination with the nitrogen atom, a heterocyclic five- or six-membered ring;
R7 stands for hydrogen or alkyl (1-4 C);
R8 and Rg stand for hydrogen or methyl, n is the number 0, 1 or 2 and the dotted line means an optional C-C bond.
The present invention is directed to in~ermediates useful in the synthesis of the compounds of formula I. Such intermediates - 1 _ are compounds of the general formula II:
in which Rl, R2, R3, R4 and X have the meanings mentioned above. The compounds II are, as far as known, novel compounds.
The intermediate of formula II can be prepared in ~arious manners. The most simple method to prepare the compound 11 is the condensation of vinylmethylketone (CH3-~-CH=CH2) with a compound of the general formula III:
I\ ~ III
in which Rl, R2, R3, R4 and X have the meanings mentioned above. This condensation reaction in preparing the starting material II is performed in a suitable solvent, preferably in the presence of a base, such as sodium hydroxide, potassium hydroxide, sodium ethoxide or sodium hydride.
An intermediate product formed in this condensa~ion reaction, namely a compound of formula III with a r-keto-butyl moiety at position 6, can, if desired, be isolated though it is not necessary to do so.
Starting from a compound with formula II the endproducts according to formula I can be prepared in various manners. All these routes are known per se and are standard procedures commonly used for the preparation of similar compounds. These methods are described in our copending Canadian Patent application 199,996. Thus the compounds of formula I are prepared by a process which comprises either:
a) condensing a compound of the general formula IV:
~0'~43(~
IV
(C1~2)nY
in which n and X are as previously defined and Y is a leaving group, with ammonia or an amine of the general formula V:
______-- 6 HN ~ V
or an acid addition salt thereof, wherein R5 and R6 are as previously defined; or b) reducing a compound of the general formula VI:
in which R represents - (CH2)p -CH or - ~CH2)pN3 wherein p represents zero or one and X is as previously defined; or c) for preparing compounds of general formula I in which n is zero and the dotted line in the nucleus signifies an extra bond, reacting a compound of the general formula V as defined above with a compound o the general for~ula II:
~ II
~0~743~
in which X is as previously defined in the presence of a reducing agent;
or d) reducing a compound of the general formula IX:
~ R5~
This application is a divisional of our copending Canadian Patent Application Serial No. 199,996 filed l~ay 15, 1974.
The present invention relates to certain components useful in the preparation Ofnovelbiologically active aminosubsti~uted tetracyclic compounds and to processes for the preparation thereof.
In our copending Canadian application number 199,996, filed May 15, 1974 certain compounds are disclosed which possess valuable C.N.S. activities, but at the same time exhibited exceedingly low toxicity.
These compounds are of the general formula I:
; n ~ ~ ' I
as well as the pharmaceutically acceptable salts thereof, in which X stands for oxygen, sulphur, the group ~ NR7 or the group CR8Rg-;
Rl, R2, R3 and R4 represent hydrogen, hydroxy, halogen, alkyl 6 C), alkoxy (1-6 C), ~ ;lthio (1 6 C~
or trifluoromethyl;
R5 and R6 represent hydrogen, alkyl (1-6 C), aralkyl (7-10 C) or, together in combination with the nitrogen atom, a heterocyclic five- or six-membered ring;
R7 stands for hydrogen or alkyl (1-4 C);
R8 and Rg stand for hydrogen or methyl, n is the number 0, 1 or 2 and the dotted line means an optional C-C bond.
The present invention is directed to in~ermediates useful in the synthesis of the compounds of formula I. Such intermediates - 1 _ are compounds of the general formula II:
in which Rl, R2, R3, R4 and X have the meanings mentioned above. The compounds II are, as far as known, novel compounds.
The intermediate of formula II can be prepared in ~arious manners. The most simple method to prepare the compound 11 is the condensation of vinylmethylketone (CH3-~-CH=CH2) with a compound of the general formula III:
I\ ~ III
in which Rl, R2, R3, R4 and X have the meanings mentioned above. This condensation reaction in preparing the starting material II is performed in a suitable solvent, preferably in the presence of a base, such as sodium hydroxide, potassium hydroxide, sodium ethoxide or sodium hydride.
An intermediate product formed in this condensa~ion reaction, namely a compound of formula III with a r-keto-butyl moiety at position 6, can, if desired, be isolated though it is not necessary to do so.
Starting from a compound with formula II the endproducts according to formula I can be prepared in various manners. All these routes are known per se and are standard procedures commonly used for the preparation of similar compounds. These methods are described in our copending Canadian Patent application 199,996. Thus the compounds of formula I are prepared by a process which comprises either:
a) condensing a compound of the general formula IV:
~0'~43(~
IV
(C1~2)nY
in which n and X are as previously defined and Y is a leaving group, with ammonia or an amine of the general formula V:
______-- 6 HN ~ V
or an acid addition salt thereof, wherein R5 and R6 are as previously defined; or b) reducing a compound of the general formula VI:
in which R represents - (CH2)p -CH or - ~CH2)pN3 wherein p represents zero or one and X is as previously defined; or c) for preparing compounds of general formula I in which n is zero and the dotted line in the nucleus signifies an extra bond, reacting a compound of the general formula V as defined above with a compound o the general for~ula II:
~ II
~0~743~
in which X is as previously defined in the presence of a reducing agent;
or d) reducing a compound of the general formula IX:
~ R5~
2 n ~ R6 J
n which R5, R6, X and n are as previously defined, or e) for preparing compounds of general formula I, in which n is zero and the dotted line in the nucleus signifies an extra bond, reducing a compound of the general formula VII:
VII
NOH
in which X is as herein before defined, by reaction with a metal hydride or by catalytic hydrogenation; or f) for preparing compounds of general formula I, in which n is zero and the dotted line in the nucleus does not signify an extra bond reducing a compound of general formula VII as defined above by reaction with sodium or sodium amalgam; or g) for preparing compounds of general formula I in which n ~ , reducing a compound of general formula VIII:
0 ~ t VIII
(CH2) p C=O
N R5 ~ ;
6-' in which R , R6, X and p are as previously defined; and wherein steps ~a) to (g) may be foliowed by the additional step of alkylating or phenylalkylating a compound of formula I obtained in which one or both of R5 and R6 is hydrogen to obtain the corresponding compound of formula I in which one or both of R5 and R6 are alkyl or phenylalkyl groups;
and wherein a base of formula I may be connected into a correspor.ding pharmaceutically acid addition or quaternary ammonium salt.
The compounds according to this invention contain an asymmetric carbon at position 2 of the tetracyclic molecule. By resolving these compounds or a starting product in their synthesis, the optical isomers can also be obtained in a direct way.
In the Examples the following nomenclature and numbering has been used:
\ / ~O
1, 2, 3, 4-tetrahydro-9H-tribenzo 5 ~ (b,d,f3-cycloheptatriene g !~`
^~'~\~ X = O or S
!3 1, 2, 3, 4-tetrahydro-~ribenzo~b,d,f)-oxepine or -thiepine.
g g ' 1, 2, 3, 4-tetrahydro-9H-tribenzo h ~3~ (b,d,f)-azepine By way of example the preparation of various compounds of formula II disclosed. The preparation of analogous compounds proceeds in exactly the same way.
Example 2-keto-1,2,3,4-tetrahydro-tribenzo (b,d,f)-oxepine To a solution of 42 g of the compound 10-keto-10,11-dihydrodibenzo (b,f)-oxepine in 200 ml of dry ethanol a solution of sodium ethoxide (7 g of sodium in 500 ml of ethanol) is added dropwise. After stirring the mixture for 30 minutes 16.2 ml of vinylmethylketone in 50 ml of ethanol are added, whereupon the solution is refluxed for one hour. The solution is cooled then and poured into 2 N HCl. After extracting into ether, washing the ether layer with water ~till neutral) and drying the etherial phase, the solvent is evaporated.
The residue, a red coloured oil, is chromatographed after that over an alumina column and used for further conversion immediately. Yield:
37% oil. In the same manner are prepared:
2-keto-11-methyl-1, 2, 3, 4-tetrahydro-tribenzo (b,d,f)-oxepine; melting point 146-147C.
2-keto-11,1~-dimethyl-1, 2, 3, 4-tetrahydro-tribenzo (b,d,f}oxepine; (oil).
10743~ -keto-12-chloro-1, 2, 3, 4-tetrahydro-tribenzo (b,d,f)-oxepine; n.elting point 107-108C.
-keto-11-trifluoromethyl-1, 2, 3, 4-tetrahydro-tribenzo (b,d,f)-oxepine;
(oil).
-keto-6-chloro-1, 2, 3, 4-tetrahydro-tribenzo (b,d,f)-oxepine; melting point 128-129C.
-keto-6-methyl-1, 2, 3, 4-tetrahydro-tribenzo (b,d,f)-oxepine; ~oil).
-keto-1, 2, 3, 4-tetrahydro-tribenzo (b,d,f)-thiepine; (oil).
-keto-1, 2, 3, 4-tetrahydro-9H-tribenzo (b,d,f)-cycloheptatriene; melting point 132-133C.
-keto-12-hydroxy-1, 2, 3, 4-tetrahydro-9H-tribenzo (b,d,f)-cycloheptatriene;
(oil).
-keto-12-methoxy-1, 2, 3, 4-tetrahydroxy-9H-tribenzo (b,d,f)-cyclohepta-triene; (oil).
-keto-11-methyl-12-~ethoxy-1, 2, 3, 4-tetrahydro-9H-tribenzo (b,d,f)-cycloheptatriene; (oil).
-keto-12-nlethyl-1, 2, 3, 4-tetrahydro-9H-tribenzo (b,d,f)-cycloheptatriene;
melting point 158-163C.
-keto-12-trifluoromethyl-1, 2, 3, 4-tetrahydro-9H-tribenzo (b,d,f)-cycloheptatriene; (oil).
-keto-7-chloro-1, 2, 3, 4-tetrahydro-9H-tribenzo (b,d,f)-cycloheptatriene;
~oil).
-keto-1, 2, 3, 4-tetrahydro-9H-tribenzo (b,d,f)-azepine; (oil).
-keto-9-methyl-1, 2, 3, 4-tetrahydro-9H-tribenzo (b,d,f)-azepine; (oil).
-keto-7-methoxy-9-methyl-1, 2, 3~ 4-tetrahydro-9H-tribenzo (b,d,f)-azepine; (oil).
n which R5, R6, X and n are as previously defined, or e) for preparing compounds of general formula I, in which n is zero and the dotted line in the nucleus signifies an extra bond, reducing a compound of the general formula VII:
VII
NOH
in which X is as herein before defined, by reaction with a metal hydride or by catalytic hydrogenation; or f) for preparing compounds of general formula I, in which n is zero and the dotted line in the nucleus does not signify an extra bond reducing a compound of general formula VII as defined above by reaction with sodium or sodium amalgam; or g) for preparing compounds of general formula I in which n ~ , reducing a compound of general formula VIII:
0 ~ t VIII
(CH2) p C=O
N R5 ~ ;
6-' in which R , R6, X and p are as previously defined; and wherein steps ~a) to (g) may be foliowed by the additional step of alkylating or phenylalkylating a compound of formula I obtained in which one or both of R5 and R6 is hydrogen to obtain the corresponding compound of formula I in which one or both of R5 and R6 are alkyl or phenylalkyl groups;
and wherein a base of formula I may be connected into a correspor.ding pharmaceutically acid addition or quaternary ammonium salt.
The compounds according to this invention contain an asymmetric carbon at position 2 of the tetracyclic molecule. By resolving these compounds or a starting product in their synthesis, the optical isomers can also be obtained in a direct way.
In the Examples the following nomenclature and numbering has been used:
\ / ~O
1, 2, 3, 4-tetrahydro-9H-tribenzo 5 ~ (b,d,f3-cycloheptatriene g !~`
^~'~\~ X = O or S
!3 1, 2, 3, 4-tetrahydro-~ribenzo~b,d,f)-oxepine or -thiepine.
g g ' 1, 2, 3, 4-tetrahydro-9H-tribenzo h ~3~ (b,d,f)-azepine By way of example the preparation of various compounds of formula II disclosed. The preparation of analogous compounds proceeds in exactly the same way.
Example 2-keto-1,2,3,4-tetrahydro-tribenzo (b,d,f)-oxepine To a solution of 42 g of the compound 10-keto-10,11-dihydrodibenzo (b,f)-oxepine in 200 ml of dry ethanol a solution of sodium ethoxide (7 g of sodium in 500 ml of ethanol) is added dropwise. After stirring the mixture for 30 minutes 16.2 ml of vinylmethylketone in 50 ml of ethanol are added, whereupon the solution is refluxed for one hour. The solution is cooled then and poured into 2 N HCl. After extracting into ether, washing the ether layer with water ~till neutral) and drying the etherial phase, the solvent is evaporated.
The residue, a red coloured oil, is chromatographed after that over an alumina column and used for further conversion immediately. Yield:
37% oil. In the same manner are prepared:
2-keto-11-methyl-1, 2, 3, 4-tetrahydro-tribenzo (b,d,f)-oxepine; melting point 146-147C.
2-keto-11,1~-dimethyl-1, 2, 3, 4-tetrahydro-tribenzo (b,d,f}oxepine; (oil).
10743~ -keto-12-chloro-1, 2, 3, 4-tetrahydro-tribenzo (b,d,f)-oxepine; n.elting point 107-108C.
-keto-11-trifluoromethyl-1, 2, 3, 4-tetrahydro-tribenzo (b,d,f)-oxepine;
(oil).
-keto-6-chloro-1, 2, 3, 4-tetrahydro-tribenzo (b,d,f)-oxepine; melting point 128-129C.
-keto-6-methyl-1, 2, 3, 4-tetrahydro-tribenzo (b,d,f)-oxepine; ~oil).
-keto-1, 2, 3, 4-tetrahydro-tribenzo (b,d,f)-thiepine; (oil).
-keto-1, 2, 3, 4-tetrahydro-9H-tribenzo (b,d,f)-cycloheptatriene; melting point 132-133C.
-keto-12-hydroxy-1, 2, 3, 4-tetrahydro-9H-tribenzo (b,d,f)-cycloheptatriene;
(oil).
-keto-12-methoxy-1, 2, 3, 4-tetrahydroxy-9H-tribenzo (b,d,f)-cyclohepta-triene; (oil).
-keto-11-methyl-12-~ethoxy-1, 2, 3, 4-tetrahydro-9H-tribenzo (b,d,f)-cycloheptatriene; (oil).
-keto-12-nlethyl-1, 2, 3, 4-tetrahydro-9H-tribenzo (b,d,f)-cycloheptatriene;
melting point 158-163C.
-keto-12-trifluoromethyl-1, 2, 3, 4-tetrahydro-9H-tribenzo (b,d,f)-cycloheptatriene; (oil).
-keto-7-chloro-1, 2, 3, 4-tetrahydro-9H-tribenzo (b,d,f)-cycloheptatriene;
~oil).
-keto-1, 2, 3, 4-tetrahydro-9H-tribenzo (b,d,f)-azepine; (oil).
-keto-9-methyl-1, 2, 3, 4-tetrahydro-9H-tribenzo (b,d,f)-azepine; (oil).
-keto-7-methoxy-9-methyl-1, 2, 3~ 4-tetrahydro-9H-tribenzo (b,d,f)-azepine; (oil).
Claims (42)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. Process for the preparation of compounds of the general formula:
II
in which X represents oxygen, sulphur, the group ? NR7 or the group -CR8R9-, R1, R2, R3 and R4 represent hydrogen, hydroxy, halogen, alkyl (1-6 C) alkoxy (1-6 C), or trifluoromethyl, R7 stands for hydrogen or alkyl (1-4 C), and R8, R9 stand for hydrogen or methyl, characterized in that a compound of the general formula:
III
is condensed with vinylmethylketone .
II
in which X represents oxygen, sulphur, the group ? NR7 or the group -CR8R9-, R1, R2, R3 and R4 represent hydrogen, hydroxy, halogen, alkyl (1-6 C) alkoxy (1-6 C), or trifluoromethyl, R7 stands for hydrogen or alkyl (1-4 C), and R8, R9 stand for hydrogen or methyl, characterized in that a compound of the general formula:
III
is condensed with vinylmethylketone .
2. Process according to claim 1 in which the reaction is carried out in a solvent.
3. Process according to claim 1 in which the reaction is carried out in the presence of a base.
4. Process according to claim 3 in which the base is sodium hydroxide,
5. Process according to claim 1 in which the reaction is carried out in the presence of sodium methoxide and a solvent.
6. Compound of the formula II
when prepared by the process according to claim 1 or by an obvious chemical equivalent thereof.
when prepared by the process according to claim 1 or by an obvious chemical equivalent thereof.
7. A process for the preparation of 2-keto-1,2,3,4-tetrahydro-tribenzo (b,d,f)-oxepine which comprises reacting 10-keto-10,11-dihydro-dibenzo(b,f)-oxepine with methyl vinyl ketone.
8. 2-keto-1,2,3,4-tetrahydro-tribenzo (b,d,f)-oxepine when prepared by the process according to claim 7 or by an obvious chemical equivalent thereof.
9. A process for the preparation of 2-keto-11-methyl-1,2,3,4-tetrahydro-tribenzo-oxepine which comprises reacting 10-keto-7-methyl-10,11-dihydro-dibenzo (b,f)-oxepine with methyl vinyl ketone.
10. 2-keto-11-methyl-1,2,3,4-tetrahydro-tribenzo (b,d,f)-oxepine whenever prepared by the process according to claim 9 or by an obvious chemical equivalent thereof.
11. A process for the preparation of 2-keto-11,12-dimethyl-1,2,3,4-tetrahydro-tribenzo (b,d,f)-oxepine which comprises reacting 10-keto-7,8-dimethyl-10,11-dihydro-dibenzo (b,f) oxepine with methyl vinyl ketone.
12. 2-keto-11,12-dimethyl-1,2,3,4-tetrahydro-tribenzo (b,d.f)-oxepine whenever prepared by the process according to claim 11 or by an obvious chemical equivalent thereof.
13. A process for the preparation of 2-keto-12-chloro-1,2,3,4-tetrahydro-tribenzo (b,d,f)-oxepine which comprises reacting 10-keto-8-chloro-10,11-dihydro-dibenzo (b,f) oxepine with methyl vinyl ketone.
14 2-keto-12-chloro-1,2,3,4-tetrahydro-tribenzo (b,d,f)-oxepine whenever prepared by the process according to claim 13 or by an obvious chemical equivalent thereof.
15. A process for the preparation of 2-keto-11-trifluoromethyl-1,2,3,4-tetrahydro-tribenzo (b,d,f)-oxepine which comprises reacting 10-keto-7-trifluoromethyl-10,11-dihydro-dibenzo (b,f) oxepine with methyl vinyl ketone.
16. 2-keto-11-trifluoromethyl-1,2,3,4-tetrahydro-tribenzo (b,d,f)-oxepine whenever prepared by the process according to claim 15 or by an obvious chemical equivalent thereof.
17. A process for the preparation of 2-keto-6-chloro-1,2,3,4-tetrahy-dro-tribenzo (b,d,f)-oxepine which comprises reacting 10-keto-2-chloro-10,11-dihydro-dibenzo (b,f) oxepine with methyl vinyl ketone.
18. 2-keto-6-chloro-1,2,3,4-tetrahydro-tribenzo (b,d,f)-oxepine whenever prepared by the process according to claim 17 or by an obvious chemical equivalent thereof.
19. A process for the preparation of 2-keto-6-methyl-1,2,3,4-tetrahy-dro-tribenzo (b,d,f)-oxepine which comrpises reacting 10-keto-2-methyl-10,11-dihydro-dibenzo (b,f) oxepine with methyl vinyl ketone.
20. 2-keto-6-methyl-1,2,3,4-tetrahydro-tribenzo (b,d,f)-oxepine whenever prepared by the process according to claim 19 or by an obvious chemical equivalent thereof.
21. A process for the preparation of 2-keto-1,2,3,4-tetrahydro-tribenzo (b,d,f)-thiepine which comprises reacting 10-keto-10,11-dihydro-dibenzo (b,f)-thiepine with methy vinyl ketone.
22. 2-keto-1,2,3,4-tetrahydro-tribenzo (b,d,f)-thiepine whenever prepared by the process according to claim 21 or by an obvious chemical equivalent thereof.
23. A process for the preparation of 2-keto-1,2,3,4-tetrahydro-9H-tribenzo (b,d,f)-cycloheptatriene which comprises reacting 10-keto-10,11-dihydro-5H-dibenzo (a,d) cycloheptene with methyl vinyl ketone.
24. 2-keto-1,2,3,4-tetrahydro-9H-tribenzo (b,d,f)-cycloheptatriene whenever prepared by the process according to claim 23 or by an obvious chemical equivalent thereof.
25. A process for the preparation of 2-keto-12-hydroxy-1,2,3,4-tetrahydro-9H-tribenzo (b,d,f)-cycloheptatriene which comprises reacting 10-keto-8-hydroxy-10,11-dihydro-5H-dibenzo (a,d) cycloheptatriene with methyl vinyl ketone.
26. 2-keto-12-hydroxy-1,2,3,4-tetrahydro-9H-tribenzo (b,d,f)-cycloheptatriene whenever prepared by the process according to claim 25 or by an obvious chemical equivalent thereof.
27. A process for the preparation of 2-keto-12-methoxy-1,2,3,4-tetrahydroxy-9H-tribenzo (b,d,f)-cycloheptatriene which comprises reacting 10-keto-8-methoxy-10,11-dihydro-5H-dibenzo (a,d) cycloheptene with methyl vinyl ketone.
28. 2-keto-12-methoxy-1,2,3,4-tetrahydroxy-9H-tribenzo (b,d,f)-cycloheptatriene whenever prepared by the process of claim 27 or by an obvious chemical equivalent thereof.
29. A process for the preparation of 2-keto-11-methyl-12-methoxy-1,2,3,4-tetrahydro-9H-tribenzo (b,d,f)-cycloheptatriene which comprises reacting 10-keto-7-methyl-8-methoxy-10,11-dihydro-5H-dibenzo (a,d) cyclo-heptene with methyl vinyl ketone.
30. 2-keto-11-methyl-12-methoxy-1,2,3,4-tetrahydro-9H-tribenzo (b,d,f)-cycloheptatriene whenever prepared by the process of claim 29 or by an obvious chemical equivalent thereof.
31. A process for the preparation of 2-keto-12-methyl-1,2,3,4-tetra-hydro-9H-tribenzo (b,d,f)-cycloheptatriene which comprises reacting 10-keto-8-methyl-10,11-dihydro-5H-dibenzo (a,d) cycloheptene with methyl vinyl ketone.
32. 2-keto-12-methyl-1,2,3,4-tetrahydro-9H-tribenzo (b,d,f)-cyclohep-tatriene whenever prepared by the process of claim 31 or by an obvious chemical equivalent thereof.
33. A process for the preparation of 2-keto-12-trifluoromethyl-1,2,3,4-tetrahydro-9H-tribenzo (b,d,f)-cycloheptatriene which comprises reacting 10-keto-8-trifluoromethyl-10,11-dihydro-5H-dibenzo (a,d) cycloheptene with methyl vinyl ketone.
34. 2-keto-12-trifluoromethyl-1,2,3,4-tetrahydro-9H-tribenzo (b,d,f)-cycloheptatriene whenever prepared by the process of claim 33 or by an obvious chemical equivalent thereof.
35. A process for the preparation of 2-keto-7-chloro-1,2,3,4-tetrahydro-9H-tribenzo (b,d,f)-cycloheptatriene which comprises reacting 10-keto-3-chloro-10,11-dihydro-5H-dibenzo (a,d) cycloheptene with methyl vinyl ketone.
36. 2-keto-7-chloro-1,2,3,4-tetrahydro-9H-tribenzo (b,d,f)-cycloheptatriene whenever prepared by the process of claim 35 or by an obvious chemical equivalent thereof.
37. A process for the preparation of 2-keto-1,2,3,4-tetrahydro-9H-tribenzo (b,d,f)-azepine which comprises reacting 10-keto-10,11-dihydro-5H-dibenzo (b,f)azepine with methyl vinyl ketone.
38. 2-keto-1,2,3,4-tetrahydro-9H-tribenzo (b,d,f)-azepine whenever prepared by the process of claim 37 or by an obvious chemical equivalent thereof.
39. A process for the preparation of 2-keto-9-methyl-1,2,3,4-tetrahydro-9H-tribenzo (b,d,f)-azepine which comprises reacting 5-methyl-10-keto-0,11-dihydro-5H-dibenzo (b,f) azepine with methyl vinyl ketone.
40. 2-keto-9-methyl-1,2,3,4-tetrahydro-9H-tribenzo (b,d,f)-azepine whenever prepared by the process of claim 39 or by an obvious chemical equivalent thereof.
41. A process for the preparation of 2-keto-7-methoxy-9-methyl-1,2,3,4-tetrahydro-9H-tribenzo (b,d,f)-azepine which comprises reacting 3-methoxy-5-methyl-10-keto-10,11-dihydro-5H-dibenzo (b,f) azepine with methyl vinyl keto.
42. 2-keto-7-methoxy-9-methyl-1,2,3,4-tetrahydro-9H-tribenzo (b,d,f)-azepine whenever prepared by the process of claim 41 or by an obvious chemical equivalent thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA318,926A CA1074305A (en) | 1974-05-15 | 1979-01-02 | Amino-substituted tetracyclic compounds |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA199,996A CA1051877A (en) | 1974-05-15 | 1974-05-15 | Amino-substituted tetracyclic compounds |
| CA318,926A CA1074305A (en) | 1974-05-15 | 1979-01-02 | Amino-substituted tetracyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1074305A true CA1074305A (en) | 1980-03-25 |
Family
ID=25667573
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA318,926A Expired CA1074305A (en) | 1974-05-15 | 1979-01-02 | Amino-substituted tetracyclic compounds |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1074305A (en) |
-
1979
- 1979-01-02 CA CA318,926A patent/CA1074305A/en not_active Expired
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