Claims
- 1. A compound of the formula: ##STR12## wherein: n is 1-5;
- E is CO.sub.2 R.sup.8, CO.sub.2 R.sup.12, --CONHSO.sub.2 R.sup.9, --CONR.sup.10 R.sup.10, or --NHSO.sub.2 R.sup.9 ;
- R.sup.1 is H, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, --CF.sub.3, --OR.sup.10, --SR.sup.9, --S(O)R.sup.9, S(O).sub.2 R.sup.9, NR.sup.10 R.sup.10, --CHO, --CO.sub.2 R.sup.8, --(C.dbd.O)R.sup.11, --C(OH)R.sup.6 R.sup.6, --CN, NO.sub.2, N.sub.3, substituted or unsubstituted phenyl, or substituted or unsubstituted C.sub.1 -C.sub.6 phenylalkyl;
- R.sup.5 is H, lower alkyl, or phenyl lower alkyl;
- each R.sup.6 is independently H or lower alkyl, or two R.sup.6 's may be joined to form a ring of 3-6 atoms;
- R.sup.8 is H, C.sub.1 -C.sub.6 alkyl, substituted or unsubstituted phenyl, or substituted or unsubstituted benzyl;
- R.sup.9 is CF.sub.3, C.sub.1 -C.sub.6 alkyl, substituted or unsubstituted phenyl, or C.sub.1 -C.sub.6 phenylalkyl;
- R.sup.10 is R.sup.9, H, or --(C.dbd.O)R.sup.11, or two R.sup.10 groups joined to the same nitrogen may form a ring selected from the group consisting of pyrrolidine, piperidine, morpholine, thiamorpholine, piperazine, and N-methylpiperazine;
- R.sup.11 is H, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, CF.sub.3, unsubstituted phenyl, or unsubstituted C.sub.1 -C.sub.6 phenylalkyl;
- R.sup.12 is --CH.sub.2 CONR.sup.10 R.sup.10 ;
- R.sup.15 is C.sub.1 to C.sub.3 alkyl, halogen, CF.sub.3, N.sub.3, C.sub.1 to C.sub.3 alkoxy, C.sub.1 to C.sub.3 alkylthio, or C.sub.1 to C.sub.3 alkylcarbonyl;
- R.sup.16 is H or R.sup.15 ;
- substituted means the benzene ring carries 1 or 2 R.sup.15 substituents;
- and the pharmaceutically acceptable salts thereof.
- 2. A compound of claim 1 of the formula ##STR13## wherein the substituents are as follows:
- ______________________________________R.sup.1 A B______________________________________H --(CH.sub.2).sub.3 Ph --SCH.sub.2 C(O)OHH --(CH.sub.2).sub.3 Ph --S(CH.sub.2).sub.2 C(O)OHH --(CH.sub.2).sub.3 Ph --SCH.sub.2 C(O)OCH.sub.3H --(CH.sub.2).sub.2 Ph --SCH.sub.2 C(O)OHH --(CH.sub.2).sub.3 Ph --S(CH.sub.2).sub.2 C(O)NH.sub.2H --(CH.sub.2).sub.3 Ph --S(CH.sub.2).sub.2 C(O)N(CH.sub.3).sub.2H --(CH.sub.2).sub.3 Ph --SCH.sub.2 C(CH.sub.3).sub.2 C(O)OHH --(CH.sub.2).sub.3 Ph --SC(CH.sub.3).sub.2 CH.sub.2 C(O)OH7-F --(CH.sub.2).sub.3 Ph --SCH.sub.2 C(O)OCH.sub.37-F --(CH.sub.2).sub.3 Ph --SCH.sub.2 C(O)OH5-CF.sub.3 --(CH.sub.2).sub.3 Ph --SCH.sub.2 C(O)OHH --(CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-Cl --SCH.sub.2 C(O)OHH --(CH.sub.2).sub.4 Ph --SCH.sub.2 C(O)OH4-CH.sub.3 --(CH.sub.2).sub.3 Ph --SCH.sub.2 C(O)OH6-CH.sub.3 --(CH.sub.2).sub.3 Ph --SCH.sub.2 C(O)OH8-CH.sub.3 --(CH.sub.2).sub.3 Ph --SCH.sub.2 C(O)OH6-CF.sub.3 --(CH.sub.2).sub.3 Ph --SCH.sub.2 C(O)OH6-CH --(CH.sub.2).sub.3 Ph --SCH.sub.2 C(O)OH(CH.sub.3).sub.26-OCH.sub.3 --(CH.sub.2).sub.3 Ph --SCH.sub.2 C(O)OH7-Cl --(CH.sub.2).sub.3 Ph --SCH.sub.2 C(O)OH6-F --(CH.sub.2).sub.3 Ph --SCH.sub.2 C(O)OHH --(CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-Cl --SCH.sub.2 C(O)OHH --(CH.sub.2).sub.3 C.sub.6 H.sub.4 -2-Cl --SCH.sub.2 C(O)OHH --(CH.sub.2).sub.3 C.sub.6 H.sub.4 -3-Cl --SCH.sub.2 C(O)OHH --(CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-SCH.sub.3 --SCH.sub.2 C(O)OHH --(CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-Br --SCH.sub.2 C(O)OHH --(CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-F --SCH.sub.2 C(O)OHH --(CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-CH.sub.3 --SCH.sub.2 C(O)OHH --(CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-I --SCH.sub.2 C(O)OHH --(CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-OCH.sub.3 --SCH.sub.2 C(O)OHH --(CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-CF.sub.3 --SCH.sub.2 C(O)OHH --(CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-SCH.sub.3 --SCH(CH.sub.3)C(O)OHH --(CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-F --S(CH.sub.2).sub.2 C(O)OHH --(CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-SCH.sub.3 --S(CH.sub.2).sub.2 C(O)OHH --(CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-Br --S(CH.sub.2).sub.2 C(O)OHH --(CH.sub.2).sub.3 C.sub.6 H.sub.4 -4-Cl --S(CH.sub.2).sub.2 C(O)OH6-CH --(CH.sub.2).sub.3 Ph --S(CH.sub.2).sub.2 C(O)OH(CH.sub.3).sub.26-OCH.sub.3 --(CH.sub.2).sub.3 Ph --SCH.sub.2 C(O)OH6-OCH.sub.3 --(CH.sub.2).sub.3 Ph --S(CH.sub.2).sub.2 C(O)OH6-F --(CH.sub.2).sub.3 Ph --SCH.sub.2 C(O)OHH --(CH.sub.2).sub.3 -C.sub.6 H.sub.4 -4-N.sub.3 --S(CH.sub.2).sub.2 C(O)N(CH.sub.3).sub.2______________________________________
- 3. A compound of claim 1 of the formula ##STR14## wherein the substituents are as follows:
- ______________________________________EX-AMPLE R.sup.1 A B C______________________________________30 H --CH.sub.2 CHCH.sub.2 --(CH.sub.2).sub.3 --SCH.sub.2 CO.sub.2 H Ph-4-Cl31 H --CH.sub.3 --(CH.sub.2).sub.3 --SCH.sub.2 CO.sub.2 H Ph-4-Cl32 H --(CH.sub.2).sub.3 Ph --(CH.sub.2).sub.3 Ph --SCH.sub.2 CO.sub.2 H33 H --CH.sub.2 Ph --(CH.sub.2).sub.3 Ph --SCH.sub.2 CO.sub.2 H34 H --(CH.sub.2).sub.2 Ph --(CH.sub.2).sub.3 Ph --SCH.sub.2 CO.sub.2 H39 H --CH.sub.2 Ph --(CH.sub.2).sub.3 Ph --S(CH.sub.2).sub.2 CO.sub.2 H40 H --(CH.sub.2).sub.2 Ph --(CH.sub.2).sub.3 Ph --S(CH.sub.2).sub.2 CO.sub.2 H41 H --CH.sub.2 CHCH.sub.2 --(CH.sub.2).sub.3 --S(CH.sub.2).sub.2 Ph-4-Cl CO.sub.2 H42 7-Cl --CH.sub.2 Ph --(CH.sub.2).sub.3 Ph --S(CH.sub.2).sub.2 CO.sub.2 H43 6-CF.sub.3 --CH.sub.2 Ph --(CH.sub.2).sub.3 Ph --S(CH.sub.2).sub.2 CO.sub.2 H45 6-Meo --CH.sub.2 Ph --(CH.sub.2).sub.3 Ph --SCH.sub.2 CO.sub.2 H46 5-Br --CH.sub.2 Ph --(CH.sub.2).sub.3 Ph --SCH.sub.2 CO.sub.2 H47 H --C.sub.2 H.sub.5 --(CH.sub.2).sub.3 --SCH.sub.2 CO.sub.2 H Ph-4-Cl48 Hn-C.sub.3 H.sub.7 --(CH.sub.2).sub.3 --S(CH.sub.2).sub.2 Ph-4-Cl CO.sub.2 H51 H --CH.sub.2 CCH --(CH.sub.2).sub.3 Ph --SCH.sub.2 CO.sub.2 H52 H --CCH --(CH.sub.2).sub.3 Ph --SCH.sub.2 CO.sub.2 H______________________________________
- 4. The following compounds of claim 1:
- {[4-phenyl-1-(4-(2-quinolinylmethoxy)phenyl)butyl]thio}acetic acid;
- 3-{[4-phenyl-1-(4-(2-quinolinylmethoxy)phenyl)butyl}thio]propanoic acid;
- {[4-phenyl-1-(4-(2-quinolinylmethoxy)phenyl)butyl]thio}acetic}acid, methyl ester;
- {[3-phenyl-1-(4-(2-quinolinylmethoxy)phenyl)propyl]thio}acetic}acid;
- 3-{[4-phenyl-1-(4-(2-quinolinylmethoxy)phenyl)butyl]thio}propanamide;
- N,N-dimethyl-3-{[4-phenyl-1-(4-(2-quinolinylmethoxy)phenyl)butyl]thio}propanamide;
- 2,2-dimethyl-3-{[4-phenyl-1-(4-(2-quinolinylmethoxy)phenyl)butyl]thio}propanoic acid;
- 3,3-dimethyl-3-{[4-phenyl-1-(4-(2-quinolinylmethoxy)phenyl)butyl]thio}propanoic acid;
- {[1-(4-(7-fluoro-2-quinolinylmethoxy)phenyl)-4-phenylbutyl]thio}acetic acid, methyl ester;
- {[1-(4-(7-fluoro-2-quinolinylmethoxy)phenyl)-4-phenylbutyl]thio}acetic acid;
- {[4-(phenyl)-1-(4-((5-(trifluromethyl)-2-quinolinyl)methoxy)phenyl)butyl]thio}acetic acid;
- {[4-(4-chlorophenyl)-1-(4-(2-quinolinylmethoxy)phenyl)butyl]thio}acetic acid;
- {[5-phenyl-1-(4-(2-quinolinylmethoxy)phenyl)pentyl]thio}acetic acid;
- {[4-(4-chlorophenyl)-1-(4-(2-quinolinylmethoxy)phenyl)butyl]thio}acetic acid;
- {[1-(4-(2-quinolinylmethoxy)phenyl)-4-(4-trifluoromethyl)phenyl)butyl]thio}acetic acid;
- 2-{[1-(4-(2-quinolinylmethoxy)phenyl)-4-(4-(methylthio)phenyl)butyl]thio}propanoic acid;
- 3-{[4-(4-fluorophenyl)-1-(4-(2-quinolinylmethoxy)phenyl)butyl]thio}propanoic acid;
- 3-{[4-(4-(methylthio)phenyl)-1-(4-(2-quinolinylmethoxy)phenyl)butyl]thio}propanoic acid;
- 3-{[4-(4-bromophenyl)-1-(4-(2-quinolinylmethoxy)phenyl)butyl]thio}propanoic acid;
- 3-{[4-(4-chlorophenyl)-1-(4-(2-quinolinylmethoxy)phenyl)butyl]thio}propanoic acid;
- 3-{[1-(4-(6-isopropyl-2-quinolinylmethoxy)phenyl)-4-phenylbutyl]thio}propanoic acid;
- {[1-(4-(6-methoxy-2-quinolinylmethoxy)phenyl)-4-phenylbutyl]thio}acetic acid;
- 3-{[1-(4-(6-methoxy-2-quinolinylmethoxy)phenyl)-4-phenylbutyl]thio}propanoic acid;
- {[1-(4-(6-fluoro-2-quinolinylmethoxy)phenyl)-4-phenylbutyl]thio}acetic acid;
- 7(Chlorophenyl)-4-(4-(2-quinolinylmethoxy)phenyl)hept-2-en-4-ylthioacetic acid;
- 1-(4-Chlorophenyl)-4-(4-(2-quinolinylmethoxy)phenyl)pent-4-ylthioacetic acid;
- 1,7-Diphenyl-4-(4-(2-quinolinylmethoxy)phenyl)hept-4-yl-thioacetic acid;
- 1,5-Diphenyl-2-(4-(2-quinolinylmethoxy)phenyl)pent-2-ylthioacetic acid; and
- 1,6-Diphenyl-3-(4-(2-quinolinylmethoxy)phenyl)hex-3-ylthioacetic acid.
- 5. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 1 and a pharmaceutically acceptable carrier.
- 6. A method of preventing the synthesis, the action, or the release of SRS-A or leukotrienes in a mammal which comprises administering to said mammal an effective amount of a compound of claim 1.
- 7. The method of claim 6 wherein the mammal is man.
CROSS-REFERENCE
This is a continuation in part of U.S. Ser. No. 211,642, filed June 27, 1988, now abandoned.
US Referenced Citations (7)
Foreign Referenced Citations (4)
Number |
Date |
Country |
206751 |
Mar 1986 |
EPX |
131568 |
May 1986 |
EPX |
200101 |
Mar 1988 |
EPX |
339416 |
Apr 1989 |
EPX |
Non-Patent Literature Citations (4)
Entry |
Tennant et al., Chemical Abstracts, vol. 106, 1987, Abstract 207457. |
Chang et al., Chemical Abstracts, vol. 108, 1988, Abstract 2161405. |
Bundgaapd et al., J. Med. Chem. 1987, 30 451-454. |
Saari et al., J. Med. Chem. 1978 21(8), 746-753. |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
211642 |
Jun 1988 |
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