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US 6,723,850 B1Granted
Process for the synthesis of (1-H)-benzo[c]quinolizin-3-ones derivatives
AssigneeApplied Research Systems ARS Holding N.V.
InventorsAntonio Guarna, Mario Serio, Ernesto Occhiato
Life of this patent
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Abstract
The present invention refers to a process for the preparation of (1H)-benzo[c]quinolizin-3-ones derivatives of general formula (I) which involves only three steps and the use, as starting products, of commercially available, or easily preparable, compounds. The compounds of formula (I) are useful as inhibitors of 5α-reductases.
Claims3
Process for the preparation of compounds of formula (I):
- wherein:
- R1, R2, R3, R4, R5, are the same or different, are chosen from the group consisting of H, C1-8alkyl, C2-8 alkenyl, C2-8alkinyl, cycloalkyl, aryl, halogen, CN, azide, NRR′, C1-8alkylamino, arylamino, C1-8alkyloxy, arylyoxy, COOR, CONRR′ wherein R and R′ are the same or different, are chosen from the group consisting of H, C1-8 alkyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, phenyl, naphthyl, arylC1-8alkyl;
- Q is selected from the group consisting of a single bond, C1-8alkyl, C2-8alkenyl, C2-8alkinyl, cycloalkyl, CO, CONR, NR, wherein R is as above defined;
- W is selected from the group consisting of H, C1-8alkyl, C2-8alkenyl, C2-8alkinyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, trifluoromethyl, C1-8 alkoxy, C1-8, alkoxy-C1-8alkyl, arylC1-8alkyl, aryl, aryloxy, arylamino, C1-8alkylcarbonyl, arylcarbonyl, arylcarboxyl, arycarboxyamide, halogen, CN, NRR′, C1-8alkylamino, wherein the groups alkyl, alkenyl, alkinyl, cycloalkyl, naphthyl, phenyl, can be substituted by halogen OR, phenyl, NRR′, CN, COOR, CONRR′, C1-8alkyl, wherein R and R′ are as above defined;
- n is an integer between 1 and 4;
- wherein:
- a thioamide of formula 3:
- wherein R3 and R4 are as above defined is N-alkylated with a vinyl ketone of formula 2:
- wherein R1, R2 and R3 are as above define to give the corresponding compound 4:
- wherein all of the substituents are as above defined said compound being methylated, at the sulfur atom to give the salt 5:
- wherein all the substituents are as above defined said compound 5 being directly reacted with a base to give compound 1.
8 more elements
Process for the preparation of compound of formula (I):
- wherein:
- R1, R2, R3, R4, R5, are the same or different, and are selected from the group consisting of H, C1-8 alkyl, C2-8 alkenyl, C2-8alkinyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, phenyl, naphthyl, halogen, C, azide, NRR′, C1-8alkylamino, arylamino, C1-8alkyloxy, arylyoxy, COOR, CONRR′ wherein R and R′ are the same or different, are selected from the group consisting of H, C1-8 alkyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, phenyl, naphthyl, arylC1-8alkyl;
- Q is chosen in the group consisting of a single bond, C1-8alkyl, C2-8alkenyl, C2-8alkinyl, cycloalkyl, CO, CONR and NR, wherein R is as above defined;
- W is selected from the group consisting of H, C1-8alkyl, C2-8alkenyl, C2-8alkinyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, trifluoromethyl, C1-8 alkoxy, C1-8, alkoxy-C1-8alkyl, arylC1-8alkyl, phenyl, naphthyl, aryloxy, arylamino, C1-8alkylcarbonyl, arylcarbonyl, arylcarboxyl, arycarboxyamide, halogen, CN, NRR′, and C1-8alkylamino;
- n is an integer between 1 and 4;
- wherein a thioamide of formula 3:
- wherein R3 and R4 are as above defined, is N-alkylated with a vinyl ketone of formula 2:
- wherein R1, R2 and R3 are as above defined to give the corresponding compound 4:
- wherein all of the substituents are as above defined, said compound 4 being methylated, at the sulfur atom to give the salt of formula 5:
- wherein all the substituents are as above defined, said compound of formula 5 being directly reacted with a base to give compound 1.
7 more elements
Process for the preparation of compound of formula (I):
- wherein:
- R1, R2, R3, R4, R5, are the same or different, and are selected from the group consisting of H, C1-8 alkyl, C2-8 alkenyl, C2-8alkinyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, and halogen;
- Q is selected from the group consisting of a simple bond, C1-8alkyl, C2-8alkenyl, C2-8alkinyl cyclopropane, cyclobutane, cyclopentane, cyclohexane and cycloheptane;
- W is selected from the group consisting of H, C1-8alkyl and C2-8alkenyl;
- and
- n is 1-4;
- wherein a thioamide of formula 3:
- wherein R3 and R4 are as above defined, is N-alkylated with a vinyl ketone of formula 2:
- wherein R1, R2 and R3 are as above defined to give the corresponding compound of formula 4:
- wherein all of the substituents are as above defined, compound 4 being methylated, at the sulfur atom to give the salt of formula 5:
- wherein all the substituents are as above defined, said compound of formula 5 being directly reacted with a base to give compound of formula 1.
8 more elements
Dependencies are inferred from the claim text.