# US 5,348,969 A · Diphenyloxazolyl-oxazoles as platelet aggregation inhibitors > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,348,969 A - Document ID: US5348969A - Status: Granted - Kind: A - Application number: 07/862,902 - Filed: 1992-04-03 - Granted: 1994-09-20 - Earliest claimed: 1992-04-03 - Assignees: Bristol-Myers Squibb Company - Inventors: Jeffrey L. Romine; Nicholas A. Meanwell - Web page: https://patentgrep.com/patent/US5348969A ## CPC - C07D 263/34: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms - C07D 263/32: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms - C07D 413/04: directly linked by a ring-member-to-ring-member bond - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) ## Abstract A novel series of oxazole derivatives having enhanced water solubility bioavailability and metabolic stability is disclosed in the Formula I ##STR1## Y is CH.sub.3, Ph, or OH, provided that when Y is OH, the compound exists in the keto-enol tautaumerism form ##STR2## R.sup.1 is Ph or Th; R.sup.2 is H or CH.sub.2 R.sup.3 ; R.sup.3 is H, OCH.sub.3, C.sub.1 -C.sub.5 lower alkyl, or CO.sub.2 R.sup.4 ; R.sup.4 is H or C.sub.1 -C.sub.5 lower alkyl; R.sup.5 is H or CH.sub.3 ; R.sup.6 is OHCHN or H.sub.2 N; and R.sup.7 is H or OH; or pharmaceutically acceptable salt thereof. The compounds are useful as inhibitors of ADP-induced blood platelet aggregation in human platelet-rich plasma. ## Claims ### Claim 1 A compound of the formula ##STR51## Y is CH.sub.3, Ph, or OH, provided that when Y is OH, the compound exists in the keto-enol tautaumerism form ##STR52## R.sup.1 is Ph or Th; R.sup.2 is H or CH.sub.2 R.sup.3 ; R.sup.3 is H, OCH.sub.3, C.sub.1 -C.sub.5 lower alkyl, or CO.sub.2 R.sup.4 ; R.sup.4 is H or C.sub.1 -C.sub.5 lower alkyl; R.sup.5 is H or CH.sub.3 ; or pharmaceutically acceptable salt thereof. ### Claim 2 (depends on 1) The compound of claim 1 which is methyl[2'-(4,5-diphenyl-2-oxazolyl)-[1,1'-biphenyl]-3-yloxy]acetate. ### Claim 3 (depends on 1) The compound of claim 1 which is [2'-(4,5-diphenyl-2-oxazolyl)-[1,1'-biphenyl]-3-yloxy]acetic acid. ### Claim 4 (depends on 1) The compound of claim 1 which is methyl 3-[4-(4,5-diphenyl-2-oxazolyl)-1-methyl-3-pyrazolyl]phenoxy]acetate. ### Claim 5 (depends on 1) The compound of claim 1 which is methyl[3-[4-(4,5-diphenyl-2-oxazolyl)-1-methyl-5-pyrazolyl]phenoxy]acetate ### Claim 6 (depends on 1) The compound of claim 1 which is 3-[4-(4,5-diphenyl-2-oxazolyl)-1-methyl-3-pyrazolyl]phenoxy]acetic acid. ### Claim 7 (depends on 1) The compound of claim 1 which is 3-[4-(4,5-diphenyl-2-oxazolyl)-1-methyl-5-pyrazolyl]phenoxy]acetic acid. ### Claim 8 (depends on 1) The compound of claim 1 is which is 1,1-dimethylethyl-[3-[4-(4,5-diphenyl-2-oxazolyl)-5-pyrazolyl]phenoxy]acet ate. ### Claim 9 (depends on 1) The compound of claim 1 which is [3-[4-(4,5-diphenyl-2-oxazolyl)-5-pyrazolyl]phenoxy]acetic acid. ### Claim 10 (depends on 1) The compound of claim 1 which is methyl[3-[4-(4,5-diphenyl-2-oxazolyl)-5-pyrazolyl]phenoxy]acetate. ### Claim 11 (depends on 1) The compound of claim 1 which is 2-[5-(3-methyoxyphenyl)-4-(2-methyloxazolyl]-4,5-diphenyloxazole. ### Claim 12 (depends on 1) The compound of claim 1 which is methyl[3-[4-(4,5-diphenyl-2-oxazolyl)-2-methyl-5-oxazolyl]phenoxy]acetate. ### Claim 13 (depends on 1) The compound of claim 1 which is [3-[4-(4,5-diphenyl-2-oxazolyl)-2-methyl-5-oxazolyl]phenoxy]acetic acid. ### Claim 14 (depends on 1) The compound of claim 1 which is methyl[3-[4-(4,5-diphenyl-2-oxazolyl)-2-phenyl-5-oxazolyl]phenoxy]acetate. ### Claim 15 (depends on 1) The compound of claim 1 which is [3-[4-(4,5-diphenyl-2-oxazolyl)-2-phenyl-5-oxazolyl]phenoxy]acetic acid. ### Claim 16 (depends on 1) The compound of claim 1 which is methyl[3-[4-(4,5-diphenyl-2-oxazolyl)-4,5-dihydro-5-oxazolyl]phenoxy]aceta te. ### Claim 17 (depends on 1) The compound of claim 1 which is methyl[3-[4-(4,5-diphenyl-2-oxazolyl)-4,5-dihydro-2-methyl-5-oxazolyl]phen oxy]acetate. ### Claim 18 (depends on 1) The compound of claim 1 which is methyl[3-[4-(4,5-diphenyl-2-oxazolyl)-4,5-dihydro-2-phenyl-5-oxazolyl]phen oxy]acetate. ### Claim 19 (depends on 1) The compound of claim 1 which is methyl[3-[4-(4,5-diphenyl-2-oxazolyl)-2-oxo-5-oxazolidinyl]phenoxy]acetate . ### Claim 20 (depends on 1) The compound of claim 1 which is [3-[4-(4,5-diphenyl-2-oxazolyl)-2-oxo-5-oxazolidinyl]phenoxy]acetic acid. ### Claim 21 The intermediate methyl 4,5-diphenyl-2-oxazole carboxylate. ### Claim 22 The intermediate 2'-(4,5-diphenyl-2-oxazolyl)-[1,1'-biphenyl-3-ol]. ### Claim 23 The intermediate 3-[4-(4,5-diphenyl-2-oxazolyl)-[1-methylpyrazolyl]phenol. ### Claim 24 The intermediate 1-[3-hydroxyphenyl]-2-[(dimethylamino)methylene]-2-(4,5-diphenyl-2-oxazoly l)ethanone. ### Claim 25 The intermediate 1,1-dimethylethyl-[3-[3-[(dimethylamino)methylene]-2-(4,5-diphenyl-2-oxazo lyl)-1-oxo-2-propenyl]phenoxy]acetate. ### Claim 26 The intermediate 2-[5-(3-methyoxyphenyl)-4-oxazolyl]-4,5-diphenyloxazole. ### Claim 27 The intermediate 3-[4-(4,5-diphenyl-2-oxazolyl)-2-methyl-5-oxazolyl]phenol. ### Claim 28 The intermediate 1,1-dimethylethyl-[3-[4-(4,5-diphenyl-2-oxazolyl)-5-pyrazolyl]phenoxy]acet ate. ### Claim 29 (depends on 1) A method for inhibiting blood platelet aggregation in a mammal which comprises administering a therapeutically effective amount of a compound of claim 1 or a pharmaceutically acceptable salt thereof. ### Claim 30 (depends on 1) The pharmaceutical composition for inhibiting blood platelet aggregation comprising a therapeutically effective amount of a compound of claim 1 of a pharmaceutically acceptable acid addition salt thereof and a pharmaceutical carrier.