Claims
- 1. A compound of the formula: ##STR24## wherein: R.sup.1 is H or loweralkyl;
- R.sup.2 is H or loweralkyl, or two R.sup.2 's may be joined to form a ring of 3-6 atoms;
- R.sup.3 is alkyl, C.sub.2 -C.sub.6 alkenyl, substituted or unsubstituted phenyl, or M-substituted alkyl;
- R.sup.4, R.sup.5 and R.sup.6 is each independently H, loweralkyl, C.sub.2 -C.sub.6 alkenyl, or --(CR.sup.2 R.sup.2).sub.p M;
- R.sup.7 and R.sup.8 are independently H, C.sub.1 -C.sub.3 alky, halogen, OH, ON, CF.sub.3, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, CO.sub.2 H, C.sub.1 -C.sub.3 alkoxycarbonyl, C.sub.1 -C.sub.3 alkylcarbonyl, or azide;
- R.sup.9 is CF.sub.3, loweralkyl, substituted or unsubstituted benzyl, or substituted or unsubstituted phenyl;
- R.sup.10 is H, loweralkyl, unsubstituted phenyl, unsubstituted benzyl, or two R.sup.10 's attached to a nitrogen may form a ring of 5 to 7 members;
- R.sup.11 is H or --(CH.sub.2).sub.q R.sup.9 ;
- R.sup.12 is loweralkyl, substituted or unsubstituted benzyl, or substituted or unsubstituted phenyl;
- R.sup.13 is H, loweralkyl, substituted or unsubstituted phenyl, or substituted or unsubstituted benzyl;
- R.sup.14 is CH.sub.2 CH(OH)CH.sub.2 OH, --CH.sub.2 O.sub.2 CC(CH.sub.3).sub.3, --CH(CH.sub.3) O.sub.2 CC(CH.sub.3).sub.3, or --(CH.sub.2).sub.2,
- E is CH.sub.2 OH, CO.sub.2 R.sup.13, CO.sub.2 R.sup.14, tetrazol-5-yl, CHO, C(O)NR.sup.2 R.sup.2, C(O)NHS(O).sub.2 R.sup.9, or C(O)N(OR.sup.2)R.sup.2 ;
- M is
- a) OR.sup.10 ;
- b) halogen;
- c) CF.sub.3 ;
- d)SR.sup.9 ;
- e)substituted or unsubstituted phenyl;
- f) COOR.sup.10 ; ##STR25## h) tetrazole; ##STR26## k) --NHSO.sub.2 R.sup.9 ; ##STR27## m) --S(O)R.sup.9 ; n) --CONR.sup.10 R.sup.10 ;
- o) --S(O).sub.2 NR.sup.10 R.sup.10 ;
- p) --S(O).sub.2 R.sup.9 ;
- q) NO.sub.2 ; ##STR28## u) ON; v) N.sub.3 ; or
- w) H;
- X is O, S, S(O), or S(O).sub.2 ;
- n is 1-5;
- p is 0-3; and
- q is 0-4;
- substituted means 1 or 2 substituents on the benzene ring selected from C.sub.1 -C.sub.3 alkyl, halogen, ON, CF.sub.3, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, CO.sub.2 H, C.sub.1 -C.sub.3 alkoxycarbonyl, C.sub.1 -C.sub.3 alkylcarbonyl, and azide;
- and the pharmaceutically acceptable salts thereof.
- 2. A compound of claim 1 wherein the substituents are as follows:
- ##STR29## Ex. Bnz R.sup.3 R.sup.4 R.sup.5 R.sup.6 (CR.sup.2 R.sup.2).sub.n E X 3. 4-ClBz Me 5-F H H CH.sub.2 CO.sub.2 Et S 4. 4-ClBz Me 5-F H H CH.sub.2 CO.sub.2 H S 5. 4-ClBz Me 5-F H H CH.sub.2 CO.sub.2 H SO.sub.2 6. 4-ClBz Me 5-F H H CH(CH.sub.3) CO.sub.2 H S 7. 4-ClBz Me 5-F H H C(CH.sub.3).sub.2 CO.sub.2 H S 8. 4-ClBz Ph 5-F H H CH.sub.2 CO.sub.2 H S 9. 4-ClBz Ph 5-F H H CH(CH.sub.3) CO.sub.2 H S 10. 4-ClBz Ph 5-i-Pr H H CH.sub.2 CO.sub.2 H S 11. 4-ClBz Ph 5-i-Pr H H CH(CH.sub.3) CO.sub.2 H S 12. 4-ClBz Ph 5-t-Bu H H CH.sub.2 CO.sub.2 H S 13. 4-ClBz Ph 5-t-Bu H H CH.sub.2 CO.sub.2 H SO 14. 4-ClBz Ph 5-t-Bu H H CH.sub.2 CO.sub.2 H SO.sub.2 15. 4-ClBz Ph 5-F H H (CH.sub.2).sub.2 CO.sub.2 H S 16. 4-ClBz Ph 5-i-Pr H H (CH.sub.2).sub.2 CO.sub.2 H S 17. 4-ClBz Me 5-F H H (CH.sub.2).sub.2 CO.sub.2 H S 18. 4-ClBz Ph 5-F H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 19. 4-ClBz Ph 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 20. 4-ClBz Ph 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO 21. 4-ClBz Ph 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO.sub.2 22. 4-ClBz Ph 5-Ph H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 23. 4-ClBz Me 5-F H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub. 2 H S 24. 4-ClBz Me 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 25. 4-ClBz t-Bu 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 26. 4-ClBz t-Bu 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO 27. 4-ClBz t-Bu 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO.sub.2 28. 4-ClBz t-Bu 5-Ph H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 29. 4-ClBz Ph 5-i-Pr H H (CH.sub.2).sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 30. 4-ClBz Ph 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H O 31. 4-ClBz Me 5-FH H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H O 32. 4-ClBz Ph 5-i-Pr H H (CH.sub.2).sub.2 CO.sub.2 H O 33. 4-ClBz Me 5-F H H (CH.sub.2).sub.2 CO.sub.2 H O 34. 4-ClBz t-Bu 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 OH S 35. 4-ClBz t-Bu 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub. 2 CONH.sub.2 S 36. 4-ClBz t-Bu 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CHO S 37. 4-ClBz t-Bu 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CONH S SO.sub.2 Ph 38. 4-ClBz Ph 5-i-Pr H H (CH.sub.2).sub.2 tetrazol-5-yl S 39. 4-ClBz CH.sub.2 CH.sub.2 OH 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 40. 4-ClBz CH.sub.2 CH.sub.2 OH 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO 41. 4-ClBz CH.sub.2 CH.sub.2 OH 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO.sub.2 42. 4-ClBz C(CH.sub.3).sub.2 CH.sub.2 CO.sub.2 H 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 43. 4-ClBz C(CH.sub.3).sub.2 CH.sub.2 CO.sub.2 Me 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 44. 4-ClBz c-Pr 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 45. 4-ClBz c-Pr 5-i-Pr H H CH.sub.2 C(CH.sub. 3).sub.2 CO.sub.2 H SO 46. B 4-Clz c-Pr 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO.sub.2 47. 4-ClBz i-Pr 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 48. 4-ClBz i-Pr 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO 49. 4-ClBz i-Pr 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO.sub.2 50. 4-ClBz C(CH.sub.3).sub.2 CH.sub.2 OH 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 54. 4-ClBz t-Bu 5-c-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 55. 4-ClBz t-Bu 5-c-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO 56. 4-ClBz t-Bu 5-c-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO.sub.2 63. 4-ClBz t-Bu 5-i-Pr H H ##STR30## CO.sub.2 H S 70. 4-ClBz t-Bu 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H O 71. 4-ClBz t-Bu 5-Ph H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H O 72. 4-ClBz i-Pr 5-Ph H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H O 73. 4-ClBz i-Pr 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H O 74. 4-MeOBz Ph 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 75. 4-OHBz Ph 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO.sub.2 76. 3-I, 4-OHBz Ph 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO.sub.2 77. 3,4-di-ClBz t-Bu 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 78. 4-ClBz Ph 5-Et H 7-Me CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 79. 4-ClBz Ph 6-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 80. 4-MeOBz n-Bu 4-Me H 6-i-Pr CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO.sub.2 81. 4-ClBz t-Bu 5-OEt H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 82. 2,6-di-ClBz Ph 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO.sub.2 83. 4-ClBz t-Bu 5-i-Pr H 7-Me CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 84. 3,5-di-ClBz Ph 5-i-Pr H 6-Me CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO.sub.2 85. 4-ClBz 4-MePh 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H O 86. 4,6-di-ClBz t-Bu 5-OMe H 4-Me CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 P H S 88. 4-ClBz 4-N.sub.3h 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 91. 4-BrBz t-Bu 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO 92. 4-BrBz Ph 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO.sub.2 93. 4-BrBz Ph 5-MeO H 6-Me CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO.sub.2 94. 4-IBz Ph 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO.sub.2 95. 4-SMeBz Ph 4-Me 5-i-Pr 7-Ac CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 96. 4-S(O).sub.2 NMe.sub.2 4-CNPh 4-N.sub.3 5-OEt 7-OAc CH.sub.2 C(CH.sub.3).sub.2 COCH.sub.2 OH S 98. 4-ClBz Ph 5-C(OH)(CH.sub.3).sub.2 H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO.sub.2 99. 4-ClBz Ph 5-CH(CH.sub.3)CH.sub.2 OH H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO.sub.2 100. 4-ClBz t-Bu 5-C(OH)(CH.sub.3).sub.2 H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 101. 4-ClBz t-Bu 5-CH(CH.sub.3)CH.sub.2 OH H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 102. 4-ClBz n-Bu 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 103. 4-ClBz n-Bu 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO.sub.2 104. 4-ClBz Cyclohexyl 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 105. 4-ClBz Cyclohexyl 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO 106. 4-ClBz Cyclohexyl 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO.sub.2 107. 4-ClBz t-Bu 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CONHCH.sub.2 CO.sub.2 H S 108. 4-ClBz CH.sub.2 -c-Pr 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 109. 4-ClBz CH.sub.2 -c-Pr 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CONHCH.sub.2 CO.sub.2 H S 110. 4-ClBz Ph 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CONHCH.sub.2 CO.sub.2 H SO.sub.2 111. 4-ClBz Ph 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CONHCH.sub.2 CO.sub.2 H S 112. 4-ClBz t-Bu 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CON(Me).sub.2 S 113. 4-ClBz CH.sub.2 -c-Pr 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CONH.sub.2 S 114. 4-OHBz t-Bu 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 115a. 4-NO.sub.2Bz Ph 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 CH.sub.3 SO.sub.2 115b. 4-NH.sub.2Bz Ph 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO.sub.2 117. 4-ClBz t-Bu 5-i-Pr H H CH(CH.sub.3) CO.sub.2 H S 118. 4-CH.sub.3 SO.sub.2Bz t-Bu 5-i-Pr 7-Cl H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 119. 4-ClBz CH.sub.2 -c-Pr 5-i-Pr 4-CF.sub.3 7-Br CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H O 120. 4-ClBz t-Bu 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H O 122. 4-ClBz t-Bu 5-i-Pr 4-SEt H CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 OCOCH.sub.2 CO.sub.2 H S 123. 4-ClBz t-Bu 5-i-Pr 7-COMe H CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 NHCOCH.sub.2 CO.sub.2 H S 124. 4-ClBz t-Bu 5-i-Pr H H ##STR31## CO.sub.2 H S 125. 4-MeOBz 4-N.sub.3Ph 5-i-Pr HH CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO.sub.2 126. 3-CNBz t-Bu 5-i-Pr 4-S(O).sub.2 H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S Me 127. 4-ClBz CH.sub.2 CH.sub.2 CHCH.sub.2 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 128. 4-ClBz Bz 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S 129. 4-ClBz 2-(i-Pr)Ph 5-i-Pr H H CH.sub.2 C(CH.sub. 3).sub.2 CO.sub.2 H S 130. 4-ClBz 2-(i-Pr)Ph 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H SO.sub.2 131. 4-ClBz t-Bu 5-i-Pr H H CH.sub.2 C(CH.sub.3).sub.2 CO.sub.2 H S
- 3. The compounds of claim 1 which are:
- ethyl 1-(p-chlorobenzyl)-5-chloro-3-thiophenylindole-2-carboxylate;
- 1-(p-chlorobenzyl)-5-chloro3-thiophenylindole -2-carboxylic acid;
- ethyl 1-(p-chlorobenzyl)-5-fluoro3-methylthioindole-2-acetate;
- 1-(p-chlorobenzyl)-5-fluoro-3-methylthioindole -2-acetic acid;
- 1-(p-chlorobenzyl)-5-fluoro-3-methylsulfonylindole -2-acetic acid;
- 1-(p-chlorobenzyl)-5-fluoro-.alpha.-methyl-3-methylthioindole-2-acetic acid;
- 1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-5-fluoro -3-methylthioindole-2-acetic acid;
- 1-(p-chlorobenzyl)-5-fluoro-.alpha.-methyl-3-phenylthioindole-2-acetic acid;
- 1-(p-chlorobenzyl)-3-phenylthio-5-(i-propyl) -indole-2-acetic acid;
- 1-(p-chlorobenzyl)-.alpha.-methyl-3-phenylthio-5-(i-propyl)-indole-2-acetic acid;
- 1-(p-chlorobenzyl)-5-(t-butyl)-3-phenylthio -indole-2-acetic acid;
- 1-(p-chlorobenzyl)-5-(t-butyl)-3-phenylsulfinylindole -2-acetic acid;
- 1-(p chlorobenzyl)-5-(t-butyl)-3-phenylsulfonylindole-2-acetic acid;
- 1-(p-chlorobenzyl)-5-fluoro-3-phenylthioindole -2-propanoic acid;
- 1-(p-chlorobenzyl)-3-phenylthio-5-(i-propyl) -indole-2-propanoic acid;
- 1-(p-chlorobenzyl)-5-fluoro-3-methylthioindole -2-propanoic acid;
- 1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-5-fluoro-3-phenylthioindole-2-propanoic acid;
- 1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-3-phenylthio -5-(i-propyl)-indole-2-propanoic acid;
- 1-(p-chlorobenzyl)-.alpha..alpha.-dimethyl-3-phenylsulfinyl-5-(i-propyl)-indole-2-propanoic acid;
- 1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-3-phenylsulfonyl-5-(i-propyl)-indole-2-propanoic acid;
- 1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-5-phenyl-3-phenylthioindole-2-propanoic acid;
- 1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-5-fluoro-3-methylthioindole-2-propanoic acid;
- 1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-3-methylthio -5-(i-propyl)-indole-2-propanoic acid;
- 1-(p-chlorobenzyl)-3-(t-butylthio)-.alpha.,.alpha.-dimethyl-5-propyl)-indole-2-propanoic acid;
- 1-(p-chlorobenzyl)-3-(t-butylsulfinyl)-.alpha.,.alpha.-dimethyl-5-(i-propyl)-indole-2-propanoic acid;
- 1-(p-chlorobenzyl)-3-(t-butylsulfonyl)-.alpha.,.alpha.-dimethyl-5-(i-propyl)-indole-2-propanoic acid;
- 1-(p-chlorobenzyl)-3-(t-butylthio)-.alpha.,.alpha.-dimethyl -5-phenylindole-2-propanoic acid;
- 1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-3-(phenylthio) -5-(i-propyl)-indole-2-butanoic acid;
- 3-[1-(p-chlorobenzyl)-3-(t-butylthio)-5-(i-propyl)-indole-2-yl]-2,2-dimethylpropanol;
- 1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-5-isopropyl -3-(n-butylthio)indole-2-propanoic acid;
- 1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-5-isopropyl -3-cyclohexylthioindole-2-propanoic acid;
- N-[1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-5-isopropyl -3-t-butylthioindole-2-propanoyl]glycine sodium salt;
- 1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-5-isopropyl -3-cyclopropylmethylthioindole-2-propanoic acid;
- 1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-5-isopropyl -3-cyclopropylmethylthioindole-2-propionamide;
- 1-(p-aminobenzyl)-.alpha.,.alpha.-dimethyl-5-isopropyl -3-phenylsulfonylindole-2-propanoic acid;
- 1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-5-isopropyl -3-(5-chlorobenzothiazol-2-ylthio)indole-2-propanoic acid;
- 1[(p-chlorobenzyl)-5-(isopropyl)-3-(t-butylthio)-indole-2-methyl]-1-cyclopentane carboxylic acid;
- 1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-5-isopropyl-3-(1-buten-4-ylthio)indole-2-propanoic acid, sodium salt;
- 1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-5-isopropyl -3-(benzylthio)indole-2-propanoic acid;
- 1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-5-isopropyl -3-(2-isopropylphenylthio)indole-2-propanoic acid;
- 1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-5-isopropyl -3-(2-isopropylphenylsulfonyl)indole-2-propanoic acid; and
- 1-(p-chlorobenzyl)-3-(t-butylthio)-.alpha.,.alpha.-dimethyl -5-(i-propyl)indole-2-propanoic acid, sodium salt.
- 4. The compounds of claims 3 which are:
- 1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-3-phenylthio -5-(i-propyl)-indole-2-propanoic acid;
- 1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-3-phenylsulfonyl -5-(i-propyl)-indole-2-propanoic acid;
- 1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-5-phenyl-3-phenylthioindole-2-propanoic acid;
- 1-(p-chlorobenzyl)-3-(t-butylthio)-.alpha.,.alpha.-dimethyl-5-(i-propyl)-indole-2-propanoic acid;
- 1-(p-chlorobenzyl)-3-(t-butylsulfonyl)-.alpha.,.alpha.-dimethyl-5-(i-propyl)-indole-2-propanoic acid;
- 1-(p-chlorobenzyl)-3-(t-butylthio)-.alpha.,.alpha.-dimethyl-5-phenylindole-2-propanoic acid;
- 1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-5-isopropyl -3-cyclohexylthioindole-2-propanoic acid;
- N-[1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl -5-isopropyl-3-t-butylthioindole-2-propanoyl]glycine sodium salt;
- 1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-5-isopropyl -3-cyclopropylmethylthioindole-2-propanoic acid;
- 1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-5-isopropyl -3-cyclopropylmethylthioindole-2-propionamide;
- 1-(p-chlorobenzyl)-.alpha.,.alpha.-dimethyl-5-isopropyl -3-(2-isopropylphenylsulfonyl)indole-2-propanoic acid; and
- 1-(p-chlorobenzyl)-3-(t-butylthio)-.alpha.,.alpha.-dimethyl-5-(i propyl)indole-2-propanoic acid, sodium salt.
- 5. A compound of claim 1 of the formula: ##STR32## wherein: R.sup.3 is loweralkyl alkylcycloalkyl, alkyl substituted phenyl, unsubstituted phenyl, or unsubstituted benzyl;
- R.sup.4 is loweralkyl, halo, substituted or unsubstituted phenyl, or alkoxy;
- R.sup.7 is alkyl, alkoxy, azide, halogen, or hydroxy;
- R.sup.13 is H or loweralkyl;
- E is CO.sub.2 R.sup.13, CONH.sub.2, or tetrazol-5-yl; and
- n is 1-3.
- 6. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 1 and a pharmaceutically acceptable carrier.
- 7. A method of preventing the synthesis of leukotrienes in a mammal which comprises administering to said mammal an effective amount of a compound of claim 1.
- 8. The method of claim 7 wherein the mammal is man.
CROSS-REFERENCE
This is a continuation-in-part of U.S. Ser. No. 942,900, filed Dec. 17, 1986, abandoned.
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Number |
Name |
Date |
Kind |
3198807 |
Thominet |
Aug 1965 |
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3502667 |
Makenishi |
Mar 1970 |
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4654360 |
Greenhouse et al. |
Mar 1987 |
|
4876246 |
Guindon et al. |
Oct 1989 |
|
Foreign Referenced Citations (1)
Number |
Date |
Country |
166591 |
Feb 1986 |
EPX |
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
942900 |
Dec 1986 |
|