- PROCESS FOR PREPARATION OF TAZAROTENE
-
Disclosed herein is process for preparation of 6-[2-(4,4-dimethylthiochroman-6- yl)ethynyl]nicotinate known as Tazarotene of Formula (I) and its pharmaceutical acceptable salts, wherein said process comprises, reacting 4,4-dimethyl-6- acetylthiochroman with chlorinating reagent to get novel intermediate compound 6- (l,l-dichloroethyl)-4,4-dimethylthiochroman followed by converting the compound 6- (l,l-dichloroethyl)-4,4-dimethylthiochroman to get Tazarotene.
- -
-
Page/Page column 11
(2009/10/22)
-
- Process for the preparation of tazarotene intermediates and use thereof for the preparation of tazarotene
-
The present invention provides a novel intermediate of ethyl 6-[2-(4,4-dimethylthiochroman-6-yl)ethynyl] nicotinate or a pharmaceutically acceptable salt thereof and a process for its preparation. The present invention also provides for the preparation of ethyl 6-[2-(4,4-dimethylthiochroman-6-yl)ethynyl] nicotinate of Formula I or a pharmaceutically acceptable salt thereof using the intermediate.
- -
-
Page/Page column 8
(2010/11/28)
-
- Process for the preparation of Tazarotene
-
Tazarotene is prepared by deoxygenation of the corresponding S-oxide, in turn obtained according to two alternative synthetic pathways.
- -
-
Page/Page column 4
(2010/11/23)
-
- A process for the preparation of tazarotene
-
Tazarotene is prepared by deoxygenation of the corresponding S-oxide, in turn obtained according to two alternative synthetic pathways.
- -
-
Page/Page column 6
(2010/11/23)
-
- PROCESS FOR THE PREPARATION OF ACETYLENIC RETINOID
-
A process for the preparation of acetylenic retinoid, ethyl-6-[2- (4,4- dimethylthiochroman-6-yl)ethynyl]nicotinate, a compound of formula 1,comprising, (a) cyclizing phenyl-3-methylbut-2-enylsulfide, a compound of formula 6, in presence of an acid selected from sulfuric acid or p-toluenesulfonic acid to yield 4,4-dimethylthiochroman, a compound of formula 2; (b)acetylating the compound of formula 2, to 4,4 -dimethyl-6-acetylthiochroman, a compound of formula 3; (c)(i) reacting the compound of formula 3 with hydrazine;(ii) reacting resultant product of step (i) with iodine; (iii) converting the resultant product of step (ii) to 4,4-dimethyl-6- ethynyl thiochroman, a compound of formula 4 and (d) reacting the compound of formula 4 with ethyl-6-halonicotinate, a compound of formula 5, wherein X is Cl or Br, in presence of cuprous halide, a transition metal and an inorganic base.
- -
-
Page/Page column 19-20
(2008/06/13)
-
- Process for the preparation of 4,4-dimethyl-6-ethynylthiochroman
-
An improved process for the preparation of key intermediates for tazarotene, 4,4-dimethyl-6-ethynylthiochroman, is provided comprising (a) reacting 4,4-dimethyl-6-acetylthiochroman of the formula with an acid chloride and an amido-group containing compound of the general formula wherein R is hydrogen or a hydrocarbyl of from 1 to 15 carbon atoms and R1 and R2 can be the same or different and are hydrocarbyls of from 1 to 15 carbon atoms or R1 and R2 together with the nitrogen atom to which they are bonded are joined together to form a heterocyclic group, optionally containing one or more additional heterocyclic atoms, or one of R1 and R2 together with the nitrogen atom to which it bonded are joined together with the carbonyl radical to form a heterocyclic group, optionally containing one or more additional heterocyclic atoms to form a β-chloro vinyl carbonyl compound intermediate of the general formula wherein R has the aforestated meanings; and (b) reacting the β-chloro vinyl carbonyl compound intermediate with an alkali metal to provide the 4,4-dimethyl-6-ethynylthiochroman.
- -
-
-
- PROCESS FOR THE PREPARATION OF DISUBSTITUTED ACETYLENES BEARING HETEROAROMATIC AND HETEROBICYCLIC GROUPS
-
A process for the preparation of a disubstituted acetylene bearing heteroaromatic and heterobicyclic groups of formula I is provided wherein X is S, O, or NR1 wherein R1 is hydrogen or a C1-C6 straight or branched alkyl group; R is hydrogen or a C1-C6 straight or branched alkyl group; A is a substituted or unsubstituted pyridinyl, thienyl, furyl, pyridazinyl, pyrimidinyl or pyrazinyl group; n is 0--4; and B is H2 -COOH, -CH2OH, -CHO or a C1-C6 alkyl acetal derivative, -COR2or a C1-C6 alkyl ketal derivative where R2 is -(CH2),,,CH3 where m is 0-4 or COOR3 wherein R3 is a straight or branched C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aromatic group, a substituted or unsubstituted C3-C30 cycloalkyl, a substituted or unsubstituted C3-C30 cycloalkylalkyl, a substituted or unsubstituted C3-C30 cycloalkenyl, a substituted or unsubstituted C5-C30 aryl, a substituted or unsubstituted C5-C30 arylalkyl, a substituted or unsubstituted C5-C30heteroaryl, a substituted or unsubstituted C3-C30 heterocyclic ring, a substituted or unsubstituted C4-C30 heterocyclylalkyl, a substituted or unsubstituted C6-C30 heteroarylalkyl, the process comprising a Sonogashira coupling reaction between a compound of formula II wherein X and R have the aforestated meanings, with a compound of formula III wherein X' is a halogen and A, n and B have the aforestated meanings, in the presence of a base and a transition metal catalyst and in a polar aprotic solvent.
- -
-
Page/Page column 11
(2010/02/15)
-
- Polyaromatic propynyl compounds and pharmaceutical/cosmetic compositions comprised thereof
-
Novel pharmaceutically/cosmetically-active polyaromatic propynyl compounds have the structural formula (1): STR1 in which X is one of the radicals: STR2 and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.
- -
-
-
- Disubstituted acetylenes bearing heteroaromatic and heterobicyclic groups having retinoid like activity
-
Retinoid-like activity is exhibited by compounds of the formula STR1 where X is S, O, or NR' where R' is hydrogen or lower alkyl; R is hydrogen or lower alkyl; A is pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-4; and B is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH2 OH or an ether or ester derivative, or --CHO or an acetal derivative, or --COR1 or a ketal derivative where R1 is --(CH2)m CH3 where m is 0-4, or a pharmaceutically acceptable salt thereof.
- -
-
-
- Disubstituted acetylenes bearing heteroaromatic and heterobicyclic groups having retinoid like activity
-
Retinoid-like activity is exhibited by compounds of the formula STR1 where X is S, O, or NR' where R' is hydrogen or lower alkyl; R is hydrogen or lower alkyl; A is pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-2; and B is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH2 OH or an ether or ester derivative, or --CHO or an acetal derivative, or --COR1 or a ketal derivative where R1 is --(CH2)m CH3 where m is 0-4, or a pharmaceutically acceptable salt thereof.
- -
-
-
- Acetylenes disubstituted with a phenyl group and a heterobicyclic group having retinoid-like activity
-
Retinoid-like activity is exhibited by compounds of the formula STR1 where X is S, O or NR 1 where R 1 is hydrogen or lower alkyl; n is 0-5; R is H or lower alkyl and A is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH 2 OH or an ether or ester derivative thereof, or --CHO or an acetal derivative thereof, or --COR 2 or a ketal derivative thereof where R 2 is --(CH 2) m CH 3 where m is 0-4; or a pharmaceutically acceptable salt.
- -
-
-