# US 3,987,160 A · Pharmaceutical compositions comprising azapurinones useful in treating allergic respiratory disorders > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 3,987,160 A - Document ID: US3987160A - Status: Granted - Kind: A - Application number: 05/364,425 - Filed: 1973-05-29 - Granted: 1976-10-19 - Earliest claimed: 1970-12-15 - Assignees: May & Baker Limited - Inventors: Barbara Joyce Broughton; Bryan John Large; Stuart Malcolm Marshall; David Lord Pain; Kenneth Robert Harry Wooldridge - Web page: https://patentgrep.com/patent/US3987160A ## CPC - C07D 239/47: One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine - C07D 239/48: Two nitrogen atoms - C07D 317/68: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen - C07D 487/04: Ortho-condensed systems - Y02P 20/55: Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS ## Abstract 8-Azapurin-6-ones substituted in the 2-position by an unsubstituted or substituted phenyl or naphthyl group, or by an alkenyl or alkynyl group, a cycloalkyl group, an alkyl group contaning 2 to 10 carbon atoms, or an alkyl group containing 1 to 10 carbon atoms carrying one or more substitutents selected from halogen atoms and hydroxy, cycloalkyl, alkoxy, phenyl and substituted phenyl groups, and pharmaceutically acceptable salts thereof, possess pharmacological properties useful, for example, in the treatment of allergic bronchial asthma. ## Claims ### Claim 1 A pharmaceutical composition useful for the treatment of allergic respiratory disorders manifested by the interaction of tissue-fixed antibodies with specific antigens in human subjects which comprises at least one 8-azapurin-6-one derivative of the formula: ##SPC14## wherein R is phenyl, or phenyl with one to three substituents selected from the group consisting of hydroxy, alkyl, alkoxy, alkenyloxy, phenoxy, phenylalkoxy, and alkylthio, said alkyl and alkyl portion of said alkylthio and phenylalkoxy containing 1 to 6 carbon atoms each, said alkoxy containing 1 to 10 carbon atoms each, and said alkenyloxy containing 2 to 10 carbon atoms each, or a pharmaceutically acceptable salt thereof, in association with a pharmaceutical carrier, the composition containing 0.1 to 50% by weight of said azapurinone compound. ### Claim 2 (depends on 1) The pharmaceutical composition of claim 1 comprising an 8-azapurin-6-one derivative of the formula: ##SPC15## wherein R.sup.8 is hydroxy, alkoxy of 1 through 6 carbon atoms, alkenyloxy of 2 through 6 carbon atoms, or phenylalkoxy in which the alkoxy portion is of 1 through 6 carbon atoms, R.sup.9 is hydroxy, alkyl or alkoxy of 1 through 6 carbon atoms, or phenylalkoxy in which the alkoxy portion is of 1 through 6 carbon atoms, and m is 0, 1 or 2, the atoms or groups represented by the symbol R.sup.9 being the same or different when m is 2, or a pharmaceutically acceptable salt thereof. ### Claim 3 (depends on 1) The pharmaceutical composition of claim 1 comprising an 8-azapurin-6-one derivative of the formula: ##SPC16## wherein R.sup.10 is phenyl or a group of the formula: ##SPC17## wherein R.sup.11 is hydroxy, straight- or branched-chain alkoxy of 1 to 10 carbon atoms, straight- or branched-chain alkenyloxy of 2 to 10 carbon atoms, phenoxy, phenylalkoxy in which the alkoxy moiety is straight- or branched-chain of 1 to 6 carbon atoms, or straight- or branched-chain alkylthio of 1 to 6 carbon atoms, and the symbols R.sup.12 are the same or different and each is hydrogen, hydroxy, straight- or branched-chain alkyl or alkoxy of 1 to 6 carbon atoms, or phenylalkoxy in which the alkoxy moiety is straight- or branched-chain of 1 to 6 carbon atoms, or a pharmaceutically acceptable salt thereof. ### Claim 4 (depends on 1) The pharmaceutical composition of claim 1 in which R is selected from the group consisting of 2-hydroxyphenyl, 2-ethoxyphenyl, 2-isopropoxyphenyl, 2-n-butoxyphenyl, 2-sec-butoxyphenyl, 2-isobutoxyphenyl, 2-n-pentyloxyphenyl, 2-isopentyloxyphenyl, 5-tert-butyl-2-methoxyphenyl, 2-n-hexyloxyphenyl, 2-benzyloxyphenyl, 5-hydroxy-2-methoxyphenyl, 2,4-dimethoxyphenyl, 2,5-dimethoxyphenyl, 2,5-dibenzyloxyphenyl, 5-benzyloxy-2-methoxyphenyl, 2,5-dihydroxyphenyl, 2-methoxy-5-methylphenyl, 2-allyloxyphenyl, phenyl, and 3-n-hexyloxyphenyl. ### Claim 5 (depends on 1) The pharmaceutical composition of claim 1 comprising 8-aza-2-(2-methoxyphenyl)purin-6-one, or a pharmaceutically acceptable salt thereof. ### Claim 6 (depends on 1) The pharmaceutical composition of claim 1 comprising 8-aza-2-(2-propoxyphenyl)purin-6-one, or a pharmaceutically acceptable salt thereof. ### Claim 7 (depends on 1, 15) The composition of claim 1 in liquid form capable of producing an aerosol for administration to human subjects suffering from a respiratory disorder comprising, in a pressurized pack, a solution or suspension of an effective amount of at least one 8-azapurin-6-one as defined in claim 15, or a pharmaceutically acceptable salt thereof, in a pharmaceutically acceptable liquid medium and a volatile liquid propellant in amount sufficient to produce an aerosol. ### Claim 8 (depends on 7) The composition of claim 7 in which the amount of said azapurinone present is 0.2 to 5% by weight of the liquid composition. ### Claim 9 (depends on 1) A pressurized pack provided with a valve permitting emission of an aerosol containing a solution or suspension of at least one 8-azapurin-6-one as defined in claim 1, or a pharmaceutically acceptable salt thereof, in a pharmaceutically acceptable liquid medium under a gaseous pressure capable of converting the 8-azapurin-6-one solution or suspension in the container into an aerosol on release through the valve. ### Claim 10 (depends on 1) The composition of claim 1 in the form of relatively slowly dissolving tablets suitable for sub-lingual administration. ### Claim 11 (depends on 1) A method of treatment of allergic respiratory disorders manifested by the interaction of tissue-fixed antibodies with specific antigens in human subjects which comprises administering orally, sub-lingually, nasally, rectally, or parenterally to the human subject an 8-azapurin-6-one as defined in claim 1, or a pharmaceutically acceptable salt thereof, in an amount sufficient to alleviate the respiratory disorder. ### Claim 12 (depends on 11) The method of claim 11 in which the respiratory disorder is allergic bronchial asthma. ### Claim 13 (depends on 11) The method of claim 11 wherein the 8-azapurin-6-one is a compound of the formula: ##SPC18## wherein R.sup.8 is hydroxy, alkoxy of 1 through 6 carbon atoms, alkenyloxy of 2 through 6 carbon atoms, or phenylalkoxy in which the alkoxy portion is of 1 through 6 carbon atoms, R.sup.9 is hydroxy, alkyl or alkoxy of 1 through 6 carbon atoms, or phenylalkoxy in which the alkoxy portion is of 1 through 6 carbon atoms, and m is 0, 1 or 2, the atoms or groups represented by the symbol R.sup.9 being the same or different when m is 2, or a pharmaceutically acceptable salt thereof. ### Claim 14 (depends on 11) The method of claim 11 in which the 8-azapurin-6-one is a compound of the formula: ##SPC19## wherein R.sup.10 is phenyl or a group of the formula: ##SPC20## wherein R.sup.11 is hydroxy, straight- or branched-chain alkoxy of 1 to 10 carbon atoms, straight- or branched-chain alkenyloxy of 2 to 10 carbon atoms, phenoxy, phenylalkoxy in which the alkoxy moiety is straight- or branched-chain of 1 to 6 carbon atoms, or straight- or branched-chain alkylthio of 1 to 6 carbon atoms, and the symbols R.sup.12 are the same or different and each is hydrogen, hydroxy, straight- or branched-chain alkyl or alkoxy of 1 to 6 carbon atoms, or phenylalkoxy in which the alkoxy moiety is straight- or branched-chain of 1 to 6 carbon atoms, or a pharmaceutically acceptable salt thereof. ### Claim 15 (depends on 11) The method of claim 11 in which the 8-azapurin-6-one is a compound in which R is selected from the group consisting of 2-hydroxyphenyl, 2-ethoxyphenyl, 2-isopropoxyphenyl, 2-n-butoxyphenyl, 2-sec-butoxyphenyl, 2-isobutoxphenyl, 2-n-pentyloxyphenyl, 2-isopentyloxyphenyl, 5-tert-butyl-2-methoxyphenyl, 2-n-hexyloxyphenyl, 2-benzyloxyphenyl, 5-hydroxy-2-methoxyphenyl, 2,4-dimethoxyphenyl, 2,5-dimethoxyphenyl, 2,5-dibenzyloxyphenyl, 5-benzyloxy-2-methoxyphenyl, 2,5-dihydroxyphenyl, 2-methoxy-5-methylphenyl, 2-allyloxyphenyl, phenyl, and 3-n-hexyloxyphenyl. ### Claim 16 (depends on 11) The method of claim 11 in which the 8-azapurin-6-one is 8-aza-2-(2-methoxyphenyl)purin-6-one, or a pharmaceutically acceptable salt thereof. ### Claim 17 (depends on 11) The method of claim 11 in which the 8-azapurin-6-one is 8-aza-2-(2-propoxyphenyl)purin-6-one, or a pharmaceutically acceptable salt thereof.