5-amino-1-(4-naphthoylbenzyl)-1,2,3-triazole-4-carboxamides and analogs as antiproliferative agents

{
  "publication_number": "US4923885A",
  "country": "US",
  "kind": "A",
  "title": "5-amino-1-(4-naphthoylbenzyl)-1,2,3-triazole-4-carboxamides and analogs as antiproliferative agents",
  "abstract": "Novel 5-Amino-1-(4-Naphthoylbenzyl)-1,2,3-triazole-4-carboxamides and analogs are disclosed as having antiproliferative activities useful in the treatment and control of psoriasis, inflammatory bowel syndrome, cutaneous leishmanilisis and certain types of cancer.",
  "claims": [
    "1. A pharmaceutical composition for controlling, hyperliferation in mammalian cells comprising a pharmaceutical carrier and a therapeutically effective amount of a compound of formula ##STR8## wherein p is 0 to 2; m and n independently are 0 to 4; q is 0 to 3; Y is 0, S, SO, SO 2, CO, CHCN, CHF, CH 2, or C═NR 6 where R 6 represents (a) hydrogen; (b) loweralkyl; (c) hydroxy; (d) loweralkoxy; (e) amino; (f) loweralkylamino; (g) diloweralkylamino; or (h) cyano; R 4, R 5 and R 7 independently are (a) halogen; (b) cyano; (c) trifluoromethyl; (d) loweralkanoyl; (e) nitro; (f) loweralkyl; (g) loweralkoxy; (h) carboxy; (i) carbaloxy; (j) trifluoromethoxy; (k) acetamido; (l) loweralkylthio; (m) loweralkylsulfonyl; (n) loweralkylsulfonyl; (o) trichlorovinyl; (p) trifluoromethylthio; (q) trifluoromethylsulfinyl; or (r) trifluoromethylsulfonyl; R 2 is (a) amino; (b) mono or diloweralkylamino; (c) acetamido; (d) acetimido; (e) ureido; (f) formamido; (g) formimido; or (h) guanidino; and R 3 is (a) carbamoyl; (b) cyano; (c) carbazoyl; (d) carbazoyl; (e) amidino; or (f) N-hydroxycarbamoyl.",
    "2. The composition of claim 1 wherein n m, and q independently are 0, 1 or 2; p is 1; Y is O, S, CO, or CH 2; R4 is (a) fluoro; (b) chloro; (c) bromo; (d) methyl; (e) trifluoromethyl; (f) cyano; (g) carbomethoxy; (h) trifluoromethoxy; (i) trifluoromethylthio; (j) nitro; or (k) trichlorovinyl; R 5 and R 7 independently are (a) chloro; (b) bromo; (c) fluoro; (d) methyl; (e) trifluoromethyl; (f) cyano; (g) carbalkoxy; (h) trichlorovinyl; (i) nitro. (j) trifluoromethyoxy; or (k) trifluoromethylthio.",
    "3. The composition of claim 1 wherein p is 1; R 4 is chloro or fluoro; m is 0, 1 or 2; n and q independently are 0 or 1; and R 5 and R 7 independently are chloro or fluoro.",
    "4. The composition of claim 1 wherein the compound is 5-amino-1(4-[4-chloronaphthoyl]-3,5-dichlorobenzyl)-1,2,3-triazole-4-carboxamide.",
    "5. A compound of formula ##STR9## wherein p is 0 to 2; m and n independently are 0 to 4; q is 0 to 3; Y is O, S, SO, SO 2, CO, CHCN, CHF, CH 2, or C═NR 6 where R 6 represents (a) hydrogen; (b) loweralkyl; (c) hydroxy; (d) loweralkoxy; (e) amino; (f) loweralkylamino; (g) diloweralkylamino; or (h) cyano; R 4, R 5 and R 7 independently are (a) halogen; (b) cyano; (c) trifluoromethyl; (d) loweralkanoyl; (e) nitro; (f) loweralkyl; (g) loweralkoxy; (h) carboxy; (i) carbaloxy; (j) trifluoromethoxy; (k) acetamido; (l) loweralkylthio; (m) loweralkylsulfonyl; (n) loweralkylsulfonyl; (o) trichlorovinyl; (p) trifluoromethylthio; (q) trifluoromethylsulfinyl; or (r) trifluoromethylsulfonyl; R 2 is (a) amino; (b) mono or diloweralkylamino; (c) acetamido; (d) acetimido; (e) ureido; (f) formamido; (g) formimido; or (h) guanidino; and R 3 is (a) carbamoyl; (b) cyano; (c) carbazoyl; (d) carbazoyl; (e) amidino; or (f) N-hydroxycarbamoyl.",
    "6. The compound of claim 9 wherein R4 is (a) fluoro; (b) chloro; (c) bromo; (d) methyl; (e) trifluoromethyl; (f) cyano; (g) carbomethoxy; (h) trifluoromethoxy; (i) trifluoromethylthio; (j) nitro; or (k) trichlorovinyl; R 5 and R 7 independently are (a) chloro; (b) bromo; (c) fluoro; (d) methyl; (e) trifluoromethyl; (f) cyano; (g) carbalkoxy; (h) trichlorovinyl; (i) nitro. (j) trifluoromethyoxy; or (k) trifluoromethylthio.",
    "7. The compound of claim 9 wherein p is 1; R 4 is chloro or fluoro; m is 0, 1 or 2; n and q independently 0 or 1; and R 5 and R 7 independently are chloro or fluoro.",
    "8. The compound of claim 9 which is the compound is 5-amino-1-(4-[4-chloronaphthoyl]-3,5-dichlorobenzyl)-1,2,3-triazole-4-carboxamide."
  ],
  "cpc": [
    "C07D 249/04"
  ],
  "assignees": [
    "MERCK & CO INC"
  ],
  "filing_date": "1988-08-19",
  "publication_date": "1990-05-08",
  "grant_date": "1990-05-08",
  "priority_date": "1988-08-19",
  "application_number": "US-23377988-A",
  "family_id": "22878658",
  "citations": [
    "EP0151528A2",
    "US4227004A",
    "US4590201A"
  ]
}