Process for preparing benzopyran compounds

Details Process for preparing benzopyran compounds Process for preparing benzopyran compounds

1995-05-26

1997-04-01

Richter, Johann

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D40504

Patent

active

056167210

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP93/03257 filed Nov. 19, 1993.
The present invention relates to a new process for preparing certain substituted benzopyran compounds, intermediates useful in the process, and to a process for the preparation of the intermediates. Substituted benzopyran compounds are known in the art. For example, EP 0 173 516-A discloses a class of substituted benzopyran compounds which are described as compounds having activity as leukotriene antagonists and useful in therapy in the treatment of, for example, diseases induced by leukotrienes and 5-.alpha.-reductase.
The present invention relates to a new process for preparing certain of the benzopyran compounds described in EP 0 173 516-A, and in particular provides an efficient route to the compounds in which far fewer reaction steps are involved than has hitherto been described. A reduction in the number of reaction steps involved in preparing end products generally results in a much more efficient and cost-effective route than one involving large numbers of steps.
The present invention therefore provides in a first aspect a process for preparing a compound of structure (I): ##STR3## in which, R.sup.1 is C.sub.1-20 alkyl, C.sub.2-20 alkenyl, C.sub.2-20 alkynyl, or a group of structure: ##STR4## each of which may be substituted by one or two substituents selected independently from C.sub.1-20 alkyl, C.sub.2-20 alkenyl or C.sub.2-20 alkynyl, up to 5 carbon atom(s) of which may optionally be replaced by oxygen atom(s), sulphur atom(s), halogen atom(s), nitrogen atom(s), benzene ring(s), thiophene ring(s), naphthalene ring(s), carbocyclic ring(s) of from 4 to 7 carbon atom(s), carbonyl group(s), carbonyloxy group(s), hydroxy group(s), carboxy group(s), azido group(s) and/or nitro group(s); hydroxy, nitro, a group of general formula --COOR.sup.4 (wherein R.sup.4 represents hydrogen or C.sub.1-6 alkyl), C.sub.1-6 alkyl, C.sub.1-6 alkoxy or C.sub.1-6 alkylthio; vinylene, propenylene, butenylene, butadienylene or ethynylene group optionally being substituted by one, two or three C.sub.1-10 alkyl and/or phenyl group(s); and compound of structure (II) ##STR5## or a salt, hydrate or solvate thereof, in which R.sup.1, R.sup.2, R.sup.3, A and X are as described for structure (I), and optionally thereafter forming a salt, solvate or hydrate thereof.
Suitably, R.sup.1 is C.sub.1-20 alkyl, C.sub.2-20 alkenyl, C.sub.2-20 alkynyl, or a group of structure: ##STR6## each of which may be substituted by one or two substituents selected independently from C.sub.1-20 alkyl, C.sub.2-20 alkenyl or C.sub.2-20 alkynyl, up to 5 carbon atom(s) of which may optionally be replaced by oxygen atom(s), sulphur atom(s), halogen atom(s), nitrogen atom(s), benzene ring(s), thiophene ring(s), naphthalene ring(s), carbocyclic ring(s) of from 4 to 7 carbon atom(s), carbonyl group(s), carbonyloxy group(s), hydroxy group(s), carboxy group(s), azido group(s) and/or nitro group(s).
Preferably R.sup.1 is a group of structure (i) substituted or unsubstituted by one or two substituents selected independently from C.sub.1-20 alkyl, C.sub.2-20 alkenyl or C.sub.2-20 alkynyl, up to 5 carbon atom(s) of which may optionally be replaced by oxygen atom(s), sulphur atom(s), halogen atom(s), nitrogen atom(s), benzene ring(s), thiophene ring(s), naphthalene ring(s), carbocyclic ring(s) of from 4 to 7 carbon atom(s), carbonyl group(s), carbonyloxy group(s), hydroxy group(s), carboxy group(s), azido group(s) and/or nitro group(s).
More preferably R.sup.1 is a group of structure (i) substituted in the para position of the ring by a single substituent selected from the above, in particular R.sup.1 is a group of structure ##STR7##
Suitably, R.sup.2 is hydrogen or C.sub.1-6 alkyl; preferably R.sup.2 is hydrogen.
Suitably, R.sup.3 is hydrogen, halogen, hydroxy, nitro, a group of general formula --COOR.sup.4 (wherein R.sup.4 represents hydrogen or C.sub.1-6 alkyl) or C.sub.1-6 alkyl, C.sub.1-6 alkoxy or C.sub.1-6 alkylthio. Preferably R.sup.3 is hydrogen.
Suitably A is a single bond or a methylene, eth

REFERENCES:
patent: 4670452 (1987-06-01), Gould et al.

Affiliated with

Also associated with

Rating

Process for preparing benzopyran compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for preparing benzopyran compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for preparing benzopyran compounds will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-540188