Patent Publication Number: US-3880902-A

Title: Indanol diesters with thiocarbonic acid

Description:
United States Patent Breuer INDANOL DIESTERS WITH THIOCARBONIC ACID [75] Inventor: Hermann Breuer, Regensburg,  
 Germany [73] Assignee: E. R. Squibb &amp; Sons. Inc.,  
 Princeton, NJ.  
 [22] Filed: Apr. 11, 1974 [2] Appl. N0.: 460,007  
 [52] U.S. Cl. 260/455 B; 424/30l [51] Int. Cl. C07c 154/00 [58] Field of Search 260/455 B [56] References Cited UNITED STATES PATENTS.  
 3,637,790 1/1972 Truhcr et all. 260/455 B Primary E.\&#39;aminerLewis Gotts Assistant E.\&#39;aminerD. R. Phillips Attorney, Agent, or Firm-Lawrence S. Levinson; Merle J. Smith 57 ABSTRACT New indanol diesters with thiocarbonic acid which have the formula wherein R and R, each is hydrogen, lower alkyl, halo or trifluoromethyl are useful as fungistatic agents.  
 8 Claims, N0 Drawings INDANOL DIESTERS WITH THIOCARBONIC ACID SUMMARY OF THE INVENTION This invention relates to new indanol 0.0&#39;-diesters with thiocarbonic acid which have the formula S (I) o-c-o J wherein R and R, are independently hydrogen or halo. especially chloro. Preferably R and R, are the same.  
 DETAILED DESCRIPTION OF THE lNVENTlON The compounds of formula I are produced by reacting an unsubstituted or substituted indanol of the formula (III) with thiophosgene or with a thionocarbonic acid ester chloride of the formula in an inert organic solvent like chloroform in the presence of a base like sodium hydroxide.  
  The new compounds of this invention are fungistatic agents useful against infections caused by Dermatophytes such as &#39;I&#39;riclwplrrmn manrugrophylus and can be applied topically to the skin of an affected animal species such as mice, guinea pigs or the like in a conventional vehicle such as cream, ointment or lotion at a concentration of about 0.1 to 3 /z (by weight).  
  The following examples are illustrative of the invention.  
 EXAMPLE 1 A solution of l6.86 g. (0.1 mol.) of 7-chloro-4- indanol in 50 ml. of 2N sodium hydroxide solution is added dropwise at 20 C. with vigorous stirring to a solution of 5.75 g. (0.05 mol.) of thiophosgene in 25 ml. of anhydrous chloroform. The mixture is stirred at room temperature for hours. The layers are separated, the chloroform layer is washed twice with water, dried with calcium chloride and concentrated. 14.9 g. of crude 7-chloro-4-indanol. 0,0&#39;-diester with thioearbonic acid are obtained. The crude product is purified by recrystallizing twice from ethanol, yield 8.25 g.; m.p. l-l67C.  
 EXAMPLE 2 By substituting S-indanol for the 7-chloro-4-indanol in the procedure of Example l. S-indanol. 0.0-diester with thiocarbonic acid is obtained. yield 63%; mp l46l48C.  
 EXAMPLE 3 By substituting 4-indanol for the 7-chloro-4-indanol in the procedure of Example 1, 4-indanol, 0,0&#39;-diester with thiocarbonic acid is obtained.  
 EXAMPLE 4 By substituting 7-chloro-5-indanol for the 7-chloro- 4-indanol in the procedure of Example 1, 7-chloro-5- indanol. 0,0&#39;-diester with thiocarbonic acid is obtained.  
 EXAMPLE 5 By reacting chlorothioformic acid, 0, 2-indanyl ester with 7-trifluoromethyl-5-indanol in Example 1, 7-trifluoromethyl-S-indanol, 0,0&#39;-diester with thiocarbonic acid is obtained.  
 EXAMPLE 6 By substituting 6-methyl-4-indanol for the 7-chloro- 4-indanol in the procedure of Examale l. 6-methyl-4- indanol. 0.0&#39;-diester with thiocarbonic acid is obtained.  
 EXAMPLE 7 By substituting 6-bromo-4-indanol for the 7-chloro- 4-indanol in the procedure of Example 1, 6-bromo-4- indanol. 0.0&#39;-diester with thiocarbonic acid is obtained.  
 What is claimed is:  
 l. A compound of the formula wherein R and R, each is hydrogen. lower alkyl. halo or trifluoromethyl.  
 2. A compound of the formula ll o c o wherein R and R, have the same meaning as in claim 1.  
 3. A compound of the formula