JPS6129346B2 - - Google Patents
Info
- Publication number
- JPS6129346B2 JPS6129346B2 JP55092337A JP9233780A JPS6129346B2 JP S6129346 B2 JPS6129346 B2 JP S6129346B2 JP 55092337 A JP55092337 A JP 55092337A JP 9233780 A JP9233780 A JP 9233780A JP S6129346 B2 JPS6129346 B2 JP S6129346B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- trans
- general formula
- oxo
- quinazolin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 74
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- -1 2-hydroxyethoxy Chemical group 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000004414 alkyl thio group Chemical group 0.000 claims description 16
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 14
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- SHVQUBPOECYGEG-AATRIKPKSA-N (e)-3-(4-oxo-6-propan-2-ylquinazolin-3-yl)prop-2-enoic acid Chemical compound N1=CN(\C=C\C(O)=O)C(=O)C2=CC(C(C)C)=CC=C21 SHVQUBPOECYGEG-AATRIKPKSA-N 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- JVXJNZOYMJJARA-AATRIKPKSA-N (e)-3-(4-oxoquinazolin-3-yl)prop-2-enoic acid Chemical class C1=CC=C2C(=O)N(/C=C/C(=O)O)C=NC2=C1 JVXJNZOYMJJARA-AATRIKPKSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 5
- PITLDNPGQYPLHR-AATRIKPKSA-N (e)-3-(4-oxo-6-propan-2-yloxyquinazolin-3-yl)prop-2-enoic acid Chemical compound N1=CN(\C=C\C(O)=O)C(=O)C2=CC(OC(C)C)=CC=C21 PITLDNPGQYPLHR-AATRIKPKSA-N 0.000 claims description 4
- UAOUBVAQDAQRPA-ONEGZZNKSA-N (e)-3-(6-hydroxy-4-oxoquinazolin-3-yl)prop-2-enoic acid Chemical compound C1=C(O)C=C2C(=O)N(/C=C/C(=O)O)C=NC2=C1 UAOUBVAQDAQRPA-ONEGZZNKSA-N 0.000 claims description 4
- OKSWTTKPZQFGEH-UHFFFAOYSA-N 2-(diethylamino)ethylazanium;chloride Chemical compound Cl.CCN(CC)CCN OKSWTTKPZQFGEH-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 96
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
- 238000002360 preparation method Methods 0.000 description 32
- 239000011541 reaction mixture Substances 0.000 description 32
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 23
- 239000007787 solid Substances 0.000 description 22
- 239000000203 mixture Substances 0.000 description 21
- 238000001816 cooling Methods 0.000 description 17
- 238000000034 method Methods 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000012312 sodium hydride Substances 0.000 description 12
- 229910000104 sodium hydride Inorganic materials 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 239000012300 argon atmosphere Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- ZLDNFLVIPPOXQL-NSCUHMNNSA-N methyl (e)-3-chloroprop-2-enoate Chemical compound COC(=O)\C=C\Cl ZLDNFLVIPPOXQL-NSCUHMNNSA-N 0.000 description 8
- 239000004533 oil dispersion Substances 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- MHMUCYJKZUZMNJ-OWOJBTEDSA-N trans-3-chloroacrylic acid Chemical class OC(=O)\C=C\Cl MHMUCYJKZUZMNJ-OWOJBTEDSA-N 0.000 description 8
- PIINGYXNCHTJTF-UHFFFAOYSA-N 2-(2-azaniumylethylamino)acetate Chemical compound NCCNCC(O)=O PIINGYXNCHTJTF-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- VHFPVEGFRVEDBK-SNAWJCMRSA-N (e)-3-(6-methylsulfanyl-4-oxoquinazolin-3-yl)prop-2-enoic acid Chemical compound N1=CN(\C=C\C(O)=O)C(=O)C2=CC(SC)=CC=C21 VHFPVEGFRVEDBK-SNAWJCMRSA-N 0.000 description 4
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 4
- UVJOZVNJHJVGRR-UHFFFAOYSA-N 6-propan-2-yl-1h-quinazolin-4-one Chemical compound N1=CNC(=O)C2=CC(C(C)C)=CC=C21 UVJOZVNJHJVGRR-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- TVBMKOMPSZAWET-UHFFFAOYSA-N 6-(2-hydroxyethoxy)-1h-quinazolin-4-one Chemical compound N1=CNC(=O)C2=CC(OCCO)=CC=C21 TVBMKOMPSZAWET-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 208000024780 Urticaria Diseases 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 3
- 239000000427 antigen Substances 0.000 description 3
- 102000036639 antigens Human genes 0.000 description 3
- 108091007433 antigens Proteins 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000005185 salting out Methods 0.000 description 3
- ROQAHFSTZYOPRY-AATRIKPKSA-N (e)-3-(6-cyclopropyl-4-oxoquinazolin-3-yl)prop-2-enoic acid Chemical compound C1=C2C(=O)N(/C=C/C(=O)O)C=NC2=CC=C1C1CC1 ROQAHFSTZYOPRY-AATRIKPKSA-N 0.000 description 2
- UJWBZDOSXFXNGK-SNAWJCMRSA-N (e)-3-(6-methoxy-4-oxoquinazolin-3-yl)prop-2-enoic acid Chemical compound N1=CN(\C=C\C(O)=O)C(=O)C2=CC(OC)=CC=C21 UJWBZDOSXFXNGK-SNAWJCMRSA-N 0.000 description 2
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
- LHBXAYHOPMCNDF-UHFFFAOYSA-N 6-cyclopropyl-1h-quinazolin-4-one Chemical compound C1=C2C(=O)NC=NC2=CC=C1C1CC1 LHBXAYHOPMCNDF-UHFFFAOYSA-N 0.000 description 2
- MTLLYGIGUMMWBT-UHFFFAOYSA-N 6-methylsulfanyl-1h-quinazolin-4-one Chemical compound N1=CNC(=O)C2=CC(SC)=CC=C21 MTLLYGIGUMMWBT-UHFFFAOYSA-N 0.000 description 2
- 206010002198 Anaphylactic reaction Diseases 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 230000036783 anaphylactic response Effects 0.000 description 2
- 208000003455 anaphylaxis Diseases 0.000 description 2
- 230000003266 anti-allergic effect Effects 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- OKYCYJVRMSDLPV-VOTSOKGWSA-N methyl (e)-3-(6-cyclopropyl-4-oxoquinazolin-3-yl)prop-2-enoate Chemical compound C1=C2C(=O)N(/C=C/C(=O)OC)C=NC2=CC=C1C1CC1 OKYCYJVRMSDLPV-VOTSOKGWSA-N 0.000 description 2
- KXQYWAWWTVIWPJ-SNAWJCMRSA-N methyl (e)-3-(6-hydroxy-4-oxoquinazolin-3-yl)prop-2-enoate Chemical compound C1=C(O)C=C2C(=O)N(/C=C/C(=O)OC)C=NC2=C1 KXQYWAWWTVIWPJ-SNAWJCMRSA-N 0.000 description 2
- ANJXTHPVOKAXEZ-AATRIKPKSA-N methyl (e)-3-(6-methylsulfanyl-4-oxoquinazolin-3-yl)prop-2-enoate Chemical compound C1=C(SC)C=C2C(=O)N(/C=C/C(=O)OC)C=NC2=C1 ANJXTHPVOKAXEZ-AATRIKPKSA-N 0.000 description 2
- CMZYFKGGXJHXFT-CMDGGOBGSA-N methyl (e)-3-[6-[2-(diethylamino)ethoxy]-4-oxoquinazolin-3-yl]prop-2-enoate Chemical compound N1=CN(\C=C\C(=O)OC)C(=O)C2=CC(OCCN(CC)CC)=CC=C21 CMZYFKGGXJHXFT-CMDGGOBGSA-N 0.000 description 2
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- PAGFRECPFGERCK-IPZCTEOASA-M sodium;(e)-3-(4-oxo-6-propan-2-ylquinazolin-3-yl)prop-2-enoate Chemical compound [Na+].N1=CN(\C=C\C([O-])=O)C(=O)C2=CC(C(C)C)=CC=C21 PAGFRECPFGERCK-IPZCTEOASA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 239000005051 trimethylchlorosilane Substances 0.000 description 2
- JKFZRNRETYGBKI-AATRIKPKSA-N (e)-3-(4-oxo-6-propoxyquinazolin-3-yl)prop-2-enoic acid Chemical compound N1=CN(\C=C\C(O)=O)C(=O)C2=CC(OCCC)=CC=C21 JKFZRNRETYGBKI-AATRIKPKSA-N 0.000 description 1
- VBLWQMTYOGGUDD-VOTSOKGWSA-N (e)-3-(4-oxo-6-propylquinazolin-3-yl)prop-2-enoic acid Chemical compound N1=CN(\C=C\C(O)=O)C(=O)C2=CC(CCC)=CC=C21 VBLWQMTYOGGUDD-VOTSOKGWSA-N 0.000 description 1
- WQVBRDNBOVJZND-ONEGZZNKSA-N (e)-3-(6-bromo-4-oxoquinazolin-3-yl)prop-2-enoic acid Chemical compound C1=C(Br)C=C2C(=O)N(/C=C/C(=O)O)C=NC2=C1 WQVBRDNBOVJZND-ONEGZZNKSA-N 0.000 description 1
- PABRMOSEIGHZND-VOTSOKGWSA-N (e)-3-(6-butan-2-yl-4-oxoquinazolin-3-yl)prop-2-enoic acid Chemical compound N1=CN(\C=C\C(O)=O)C(=O)C2=CC(C(C)CC)=CC=C21 PABRMOSEIGHZND-VOTSOKGWSA-N 0.000 description 1
- AROLNQCDWFUIET-VOTSOKGWSA-N (e)-3-(6-butoxy-4-oxoquinazolin-3-yl)prop-2-enoic acid Chemical compound N1=CN(\C=C\C(O)=O)C(=O)C2=CC(OCCCC)=CC=C21 AROLNQCDWFUIET-VOTSOKGWSA-N 0.000 description 1
- FDEMINNFSRMQBH-BQYQJAHWSA-N (e)-3-(6-butyl-4-oxoquinazolin-3-yl)prop-2-enoic acid Chemical compound N1=CN(\C=C\C(O)=O)C(=O)C2=CC(CCCC)=CC=C21 FDEMINNFSRMQBH-BQYQJAHWSA-N 0.000 description 1
- HLWBYVFSUZBPGY-AATRIKPKSA-N (e)-3-(6-ethoxy-4-oxoquinazolin-3-yl)prop-2-enoic acid Chemical compound N1=CN(\C=C\C(O)=O)C(=O)C2=CC(OCC)=CC=C21 HLWBYVFSUZBPGY-AATRIKPKSA-N 0.000 description 1
- SCZYHQMFPKQDAP-AATRIKPKSA-N (e)-3-(6-ethyl-4-oxoquinazolin-3-yl)prop-2-enoic acid Chemical compound N1=CN(\C=C\C(O)=O)C(=O)C2=CC(CC)=CC=C21 SCZYHQMFPKQDAP-AATRIKPKSA-N 0.000 description 1
- VEOVOQYPZFYUSC-ONEGZZNKSA-N (e)-3-(6-fluoro-4-oxoquinazolin-3-yl)prop-2-enoic acid Chemical compound C1=C(F)C=C2C(=O)N(/C=C/C(=O)O)C=NC2=C1 VEOVOQYPZFYUSC-ONEGZZNKSA-N 0.000 description 1
- HPDHJUZEAIZERI-SNAWJCMRSA-N (e)-3-(6-methyl-4-oxoquinazolin-3-yl)prop-2-enoic acid Chemical compound N1=CN(\C=C\C(O)=O)C(=O)C2=CC(C)=CC=C21 HPDHJUZEAIZERI-SNAWJCMRSA-N 0.000 description 1
- LCNXPWGMYLCBGH-SNAWJCMRSA-N (e)-3-(6-methylsulfinyl-4-oxoquinazolin-3-yl)prop-2-enoic acid Chemical compound N1=CN(\C=C\C(O)=O)C(=O)C2=CC(S(=O)C)=CC=C21 LCNXPWGMYLCBGH-SNAWJCMRSA-N 0.000 description 1
- PVHUNVVTRFHOOK-SNAWJCMRSA-N (e)-3-(6-methylsulfonyl-4-oxoquinazolin-3-yl)prop-2-enoic acid Chemical compound N1=CN(\C=C\C(O)=O)C(=O)C2=CC(S(=O)(=O)C)=CC=C21 PVHUNVVTRFHOOK-SNAWJCMRSA-N 0.000 description 1
- GZZBEYDREHGWMY-VOTSOKGWSA-N (e)-3-(6-tert-butyl-4-oxoquinazolin-3-yl)prop-2-enoic acid Chemical compound N1=CN(\C=C\C(O)=O)C(=O)C2=CC(C(C)(C)C)=CC=C21 GZZBEYDREHGWMY-VOTSOKGWSA-N 0.000 description 1
- GXXMOSVTBDXJIY-AATRIKPKSA-N (e)-3-[6-(2-methylpropyl)-4-oxoquinazolin-3-yl]prop-2-enoic acid Chemical compound N1=CN(\C=C\C(O)=O)C(=O)C2=CC(CC(C)C)=CC=C21 GXXMOSVTBDXJIY-AATRIKPKSA-N 0.000 description 1
- ZOOZEDAPFYDZIF-LBEJWNQZSA-N (e)-n-[2-[di(propan-2-yl)amino]ethyl]-3-(4-oxo-6-propan-2-ylquinazolin-3-yl)prop-2-enamide;hydrochloride Chemical compound Cl.C1=C(C(C)C)C=C2C(=O)N(/C=C/C(=O)NCCN(C(C)C)C(C)C)C=NC2=C1 ZOOZEDAPFYDZIF-LBEJWNQZSA-N 0.000 description 1
- HCKNRHBSGZMOOF-UHFFFAOYSA-N 1-methoxy-2-methylperoxyethane Chemical compound COCCOOC HCKNRHBSGZMOOF-UHFFFAOYSA-N 0.000 description 1
- MKLDLMXFDMZYAD-UHFFFAOYSA-N 1h-quinazolin-2-one;hydrochloride Chemical compound Cl.C1=CC=C2NC(=O)N=CC2=C1 MKLDLMXFDMZYAD-UHFFFAOYSA-N 0.000 description 1
- PVJZBZSCGJAWNG-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonyl chloride Chemical compound CC1=CC(C)=C(S(Cl)(=O)=O)C(C)=C1 PVJZBZSCGJAWNG-UHFFFAOYSA-N 0.000 description 1
- IKQFHNIBFIMVOG-HRNDJLQDSA-N 2-(diethylamino)ethyl (E)-3-(6-methoxy-4-oxoquinazolin-3-yl)prop-2-enoate hydrochloride Chemical compound Cl.C1=C(OC)C=C2C(=O)N(/C=C/C(=O)OCCN(CC)CC)C=NC2=C1 IKQFHNIBFIMVOG-HRNDJLQDSA-N 0.000 description 1
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 1
- AEUZKXIHXKWHDD-UHFFFAOYSA-N 2-amino-5-(2-hydroxyethoxy)benzoic acid Chemical compound NC1=CC=C(OCCO)C=C1C(O)=O AEUZKXIHXKWHDD-UHFFFAOYSA-N 0.000 description 1
- ZAZGSPQJTLDUDD-UHFFFAOYSA-N 2-amino-5-[2-(diethylamino)ethoxy]benzoic acid;dihydrochloride Chemical compound Cl.Cl.CCN(CC)CCOC1=CC=C(N)C(C(O)=O)=C1 ZAZGSPQJTLDUDD-UHFFFAOYSA-N 0.000 description 1
- UERVAQKRBPRDJP-UHFFFAOYSA-N 2-amino-5-cyclopropylbenzoic acid Chemical compound C1=C(C(O)=O)C(N)=CC=C1C1CC1 UERVAQKRBPRDJP-UHFFFAOYSA-N 0.000 description 1
- QWNMKHLBVHTPFW-UHFFFAOYSA-N 2-amino-5-propan-2-ylbenzoic acid Chemical compound CC(C)C1=CC=C(N)C(C(O)=O)=C1 QWNMKHLBVHTPFW-UHFFFAOYSA-N 0.000 description 1
- LKWPCZDBLQUFJQ-UHFFFAOYSA-N 2-amino-5-propan-2-yloxybenzoic acid Chemical compound CC(C)OC1=CC=C(N)C(C(O)=O)=C1 LKWPCZDBLQUFJQ-UHFFFAOYSA-N 0.000 description 1
- XOTUAMWIFRDGMZ-UHFFFAOYSA-N 2-chloroprop-2-enoyl chloride Chemical compound ClC(=C)C(Cl)=O XOTUAMWIFRDGMZ-UHFFFAOYSA-N 0.000 description 1
- 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- DDOUPXWRCKUTLI-UHFFFAOYSA-N 6-[2-(diethylamino)ethoxy]-1h-quinazolin-4-one Chemical compound N1=CNC(=O)C2=CC(OCCN(CC)CC)=CC=C21 DDOUPXWRCKUTLI-UHFFFAOYSA-N 0.000 description 1
- WAYNEPFBWHYQOM-UHFFFAOYSA-N 6-[2-(diethylamino)ethoxy]-1h-quinazolin-4-one;hydrochloride Chemical compound Cl.N1=CNC(=O)C2=CC(OCCN(CC)CC)=CC=C21 WAYNEPFBWHYQOM-UHFFFAOYSA-N 0.000 description 1
- GOBVWEUSCRFCPB-UHFFFAOYSA-N 6-chloro-1h-quinazolin-4-one Chemical compound N1C=NC(=O)C2=CC(Cl)=CC=C21 GOBVWEUSCRFCPB-UHFFFAOYSA-N 0.000 description 1
- QJRNXXLTDWMENM-UHFFFAOYSA-N 6-hydroxy-1h-quinazolin-4-one Chemical compound N1C=NC(=O)C2=CC(O)=CC=C21 QJRNXXLTDWMENM-UHFFFAOYSA-N 0.000 description 1
- NOFVNLZQAOGUIT-UHFFFAOYSA-N 6-methoxy-1h-quinazolin-4-one Chemical compound N1=CNC(=O)C2=CC(OC)=CC=C21 NOFVNLZQAOGUIT-UHFFFAOYSA-N 0.000 description 1
- OHJKBCZDDATNSO-UHFFFAOYSA-N 6-propan-2-yloxy-1h-quinazolin-4-one Chemical compound N1=CNC(=O)C2=CC(OC(C)C)=CC=C21 OHJKBCZDDATNSO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 108010058846 Ovalbumin Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 206010045240 Type I hypersensitivity Diseases 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 230000002052 anaphylactic effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000002804 anti-anaphylactic effect Effects 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 238000010420 art technique Methods 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- 235000012241 calcium silicate Nutrition 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 229960003699 evans blue Drugs 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000007928 imidazolide derivatives Chemical class 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- SZQHBADGTWUZMX-VOTSOKGWSA-N methyl (e)-3-(4-oxo-6-propan-2-yloxyquinazolin-3-yl)prop-2-enoate Chemical compound C1=C(OC(C)C)C=C2C(=O)N(/C=C/C(=O)OC)C=NC2=C1 SZQHBADGTWUZMX-VOTSOKGWSA-N 0.000 description 1
- AAOIHFOCAQJJRT-VOTSOKGWSA-N methyl (e)-3-(4-oxo-6-propan-2-ylquinazolin-3-yl)prop-2-enoate Chemical compound C1=C(C(C)C)C=C2C(=O)N(/C=C/C(=O)OC)C=NC2=C1 AAOIHFOCAQJJRT-VOTSOKGWSA-N 0.000 description 1
- NGHCFPARWXWEAA-SNAWJCMRSA-N methyl (e)-3-(6-chloro-4-oxoquinazolin-3-yl)prop-2-enoate Chemical compound C1=C(Cl)C=C2C(=O)N(/C=C/C(=O)OC)C=NC2=C1 NGHCFPARWXWEAA-SNAWJCMRSA-N 0.000 description 1
- KSMSKCNSCVVPKC-AATRIKPKSA-N methyl (e)-3-(6-methoxy-4-oxoquinazolin-3-yl)prop-2-enoate Chemical compound C1=C(OC)C=C2C(=O)N(/C=C/C(=O)OC)C=NC2=C1 KSMSKCNSCVVPKC-AATRIKPKSA-N 0.000 description 1
- ZLDNFLVIPPOXQL-IHWYPQMZSA-N methyl (z)-3-chloroprop-2-enoate Chemical compound COC(=O)\C=C/Cl ZLDNFLVIPPOXQL-IHWYPQMZSA-N 0.000 description 1
- FVMMLVMSSWHEFY-UHFFFAOYSA-N methyl 2-amino-5-methylsulfanylbenzoate Chemical compound COC(=O)C1=CC(SC)=CC=C1N FVMMLVMSSWHEFY-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- CURJNMSGPBXOGK-UHFFFAOYSA-N n',n'-di(propan-2-yl)ethane-1,2-diamine Chemical compound CC(C)N(C(C)C)CCN CURJNMSGPBXOGK-UHFFFAOYSA-N 0.000 description 1
- HPTYODQESKFIKN-UHFFFAOYSA-N n,n-dimethylformamide;prop-2-enoic acid Chemical compound CN(C)C=O.OC(=O)C=C HPTYODQESKFIKN-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229940092253 ovalbumin Drugs 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- QUKMHYSWLFBRQU-FXRZFVDSSA-M sodium;(e)-3-(6-methoxy-4-oxoquinazolin-3-yl)prop-2-enoate Chemical compound [Na+].N1=CN(\C=C\C([O-])=O)C(=O)C2=CC(OC)=CC=C21 QUKMHYSWLFBRQU-FXRZFVDSSA-M 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/02—Monosaccharides
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5572879A | 1979-07-09 | 1979-07-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5625167A JPS5625167A (en) | 1981-03-10 |
| JPS6129346B2 true JPS6129346B2 (fr) | 1986-07-05 |
Family
ID=21999760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9233780A Granted JPS5625167A (en) | 1979-07-09 | 1980-07-08 | Transs33*44oxoo4hhquinazolinee33yl**22propenic acid derivative |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5625167A (fr) |
| KR (1) | KR840002243B1 (fr) |
| ZA (1) | ZA804015B (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3028835U (ja) * | 1996-03-08 | 1996-09-13 | 株式会社阪神技術研究所 | 現像処理装置 |
-
1980
- 1980-07-03 ZA ZA00804015A patent/ZA804015B/xx unknown
- 1980-07-08 JP JP9233780A patent/JPS5625167A/ja active Granted
- 1980-07-08 KR KR1019800002704A patent/KR840002243B1/ko active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3028835U (ja) * | 1996-03-08 | 1996-09-13 | 株式会社阪神技術研究所 | 現像処理装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA804015B (en) | 1981-06-24 |
| KR840002243B1 (ko) | 1984-12-07 |
| JPS5625167A (en) | 1981-03-10 |
| KR830003439A (ko) | 1983-06-20 |
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