Processes for production of quinoline or quinazoline derivatives

Details Processes for production of quinoline or quinazoline derivatives Processes for production of quinoline or quinazoline derivatives

1995-09-26

1997-12-16

Ivy, C. Warren

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546156, 546167, 544283, 514259, 514314, C07D21520, C07D21512, C07D23972, C07D23976

Patent

active

056986998

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/JP95/01210, filed 19 Jun. 1995.


TECHNICAL FIELD

This invention relates to processes for producing novel quinoline or quinazoline derivatives and their salts, which are useful as antiinflammatory agents, and to their intermediate compounds.


BACKGROUND ART

The present applicant previously filed patent applications on novel quinoline or quinazoline derivatives of value as antiinflammatory agents, particularly antiarthritic drugs (JP Application 206128/93 and JP Application 8232/94).
Referring to the technology for production of such novel quinoline or quinazoline derivatives and particularly in regard to the introduction of a 1,2,4-triazole group, this step was performed by the known reaction in the presence of a base. ##STR2##
However, this reaction involved an isomerization reaction, Under basic conditions, of 1,2,4-triazole, thus giving rise to 1,3,4-triazole (4) as a byproduct in a proportion of 10-20%. ##STR3## As a consequence, the yield was low and the necessary purification required a complicated procedure such as silica gel chromatography.


DISCLOSURE OF INVENTION

This invention is directed to:
1. A process for producing a compound of general formula (2) ##STR4## wherein Y represents a nitrogen atom or C-G in which G represents a carboxyl group which may optionally be esterified or amidated, an acyl group, a hydroxyalkyl group which may optionally be protected, or a halogen atom; ring A and ring B each may optionally be substituted; k represents 0 or 1; or a salt thereof, which comprises subjecting a compound of general formula (1) ##STR5## wherein Y, ring A, ring B, and k are respectively as defined above; X represents a leaving group; or a salt thereof to deamination reaction.
2. A process for producing a compound of general formula (1) ##STR6## wherein X, Y, ring A, ring B, and k are respectively as defined above; or a salt thereof, which comprises reacting a compound of general formula (3) ##STR7## wherein X, Y, ring A, ring B and k are respectively as defined above; or a salt thereof with 4-amino-1,2,4-triazole.
3. A process for producing a compound of general formula (2) ##STR8## wherein Y, ring A, ring B, and k are respectively as defined above; or a salt thereof, which comprises reacting a compound of general formula (3) ##STR9## wherein X, Y, ring A, ring B and k are respectively as defined above; or a salt thereof with 4-amino-1,2,4-triazole to give a compound of general formula (1) ##STR10## wherein X, Y, ring A, ring B, and k are respectively as defined above; or a salt thereof and subjecting the last-mentioned compound or salt thus obtained to deamination reaction.
4. The process according to the above items 1 or 3, wherein said deamination reaction is conducted using nitrous acid.
5. The process claimed in the above items 2 or 3, wherein X is a halogen atom.
6. The process claimed in the above items 1 or 3, wherein the compound of general formula (2) is ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-(1,2,4-triazol-1-ylmethyl)quinolin e-3-carboxylate.
7. A compound of general formula (1) ##STR11## wherein Y represents a nitrogen atom or C-G in which G represents a carboxyl group which may optionally be esterified or amidated, an acyl group, a hydroxyalkyl group which may optionally be protected, or a halogen atom; ring A and ring B each may optionally be substituted; k represents 0 or 1; X represents a leaving group; or a salt thereof.
8. The compound or salt of the above item 7, wherein Y represents C-G, where G represents C.sub.1-6 alkyloxycarbonyl.
9. The compound or salt of the above item 8, wherein G represents ethoxycarbonyl.
10. The compound or salt of the above item 7, wherein ring A is substituted by two alkoxy groups which may be the same or different.
11. The compound or salt of the above item 7, wherein ring A is substituted by two methoxy groups.
12. The compound or salt of the above item 7, wherein ring B is substituted by two alkoxy groups which may be the same or different.
13. The compound or salt of the above item 7, wherein ring

REFERENCES:
patent: 5436247 (1995-07-01), Sohda
Astlefore et al., "Synthesis of 1-Alkyl-1,2,4-triazoles: A New One-Pot Regiospecific Procedure", J. Org. Chem., vol. 54, No. 3, 1989, pp. 731-732 .

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