SK16594A3 - New 3-substituded tetrazolyl-4-oxo-4h-pyrido[1,2-a] pyrimidines derivatives - Google Patents
New 3-substituded tetrazolyl-4-oxo-4h-pyrido[1,2-a] pyrimidines derivatives Download PDFInfo
- Publication number
- SK16594A3 SK16594A3 SK165-94A SK16594A SK16594A3 SK 16594 A3 SK16594 A3 SK 16594A3 SK 16594 A SK16594 A SK 16594A SK 16594 A3 SK16594 A3 SK 16594A3
- Authority
- SK
- Slovakia
- Prior art keywords
- pyrido
- oxo
- pyrimidine
- tetrazol
- methyl
- Prior art date
Links
- 150000003230 pyrimidines Chemical class 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 238000002360 preparation method Methods 0.000 claims abstract description 46
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 4
- NYJWYCAHJRGKMI-UHFFFAOYSA-N pyrido[1,2-a]pyrimidin-4-one Chemical class C1=CC=CN2C(=O)C=CN=C21 NYJWYCAHJRGKMI-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 80
- 229910052799 carbon Inorganic materials 0.000 claims description 79
- 239000000203 mixture Substances 0.000 claims description 68
- -1 sulfuric acid ester Chemical group 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 238000002425 crystallisation Methods 0.000 claims description 8
- 230000008025 crystallization Effects 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 6
- AOPPLHKZRHZMGX-UHFFFAOYSA-N 3-(2-propan-2-yltetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CC(C)N1N=NC(C=2C(N3C=CC=CC3=NC=2)=O)=N1 AOPPLHKZRHZMGX-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 5
- SMHIZHSNVPZCNO-UHFFFAOYSA-N 9-methyl-3-(2-propyltetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCN1N=NC(C=2C(N3C=CC=C(C)C3=NC=2)=O)=N1 SMHIZHSNVPZCNO-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- CXDYEKMKXMVZET-UHFFFAOYSA-N 9-methyl-3-(1-propan-2-yltetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CC(C)N1N=NN=C1C(C1=O)=CN=C2N1C=CC=C2C CXDYEKMKXMVZET-UHFFFAOYSA-N 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 3
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 229910052740 iodine Chemical group 0.000 claims description 2
- 239000011630 iodine Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 208000025865 Ulcer Diseases 0.000 abstract description 6
- 231100000397 ulcer Toxicity 0.000 abstract description 4
- 230000002265 prevention Effects 0.000 abstract description 3
- 230000002178 gastroprotective effect Effects 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- 125000005843 halogen group Chemical group 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 105
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 64
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 63
- 229910052757 nitrogen Inorganic materials 0.000 description 46
- 238000004458 analytical method Methods 0.000 description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 239000013078 crystal Substances 0.000 description 32
- 229910000027 potassium carbonate Inorganic materials 0.000 description 32
- 235000011181 potassium carbonates Nutrition 0.000 description 32
- 239000011541 reaction mixture Substances 0.000 description 23
- 239000000706 filtrate Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 17
- 238000003756 stirring Methods 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- HIANJWSAHKJQTH-UHFFFAOYSA-N pemirolast Chemical compound CC1=CC=CN(C2=O)C1=NC=C2C=1N=NNN=1 HIANJWSAHKJQTH-UHFFFAOYSA-N 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- FDESMPVXUFITNN-UHFFFAOYSA-N 3-(2h-tetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical class C=1N=C2C=CC=CN2C(=O)C=1C1=NN=NN1 FDESMPVXUFITNN-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 229960000905 indomethacin Drugs 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- PUHOBIKKRNSOGJ-UHFFFAOYSA-N 6-methyl-3-(2h-tetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound O=C1N2C(C)=CC=CC2=NC=C1C1=NN=NN1 PUHOBIKKRNSOGJ-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VFMCUTPRJLZEEW-UHFFFAOYSA-N 4h-pyrido[1,2-a]pyrimidine Chemical compound C1=CC=CN2CC=CN=C21 VFMCUTPRJLZEEW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003518 caustics Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 2
- YXZFFTJAHVMMLF-UHFFFAOYSA-N 1-bromo-3-methylbutane Chemical compound CC(C)CCBr YXZFFTJAHVMMLF-UHFFFAOYSA-N 0.000 description 2
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 description 2
- WJDSFMYSFJVOIB-UHFFFAOYSA-N 3-(1-ethyltetrazol-5-yl)-6-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound CCN1N=NN=C1C(C1=O)=CN=C2N1C(C)=CC=C2 WJDSFMYSFJVOIB-UHFFFAOYSA-N 0.000 description 2
- JXKREGFNAXBKOD-UHFFFAOYSA-N 3-[1-[(4-bromophenyl)methyl]tetrazol-5-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC(Br)=CC=C1CN1C(C=2C(N3C=CC=CC3=NC=2)=O)=NN=N1 JXKREGFNAXBKOD-UHFFFAOYSA-N 0.000 description 2
- VGMDPUAUNOKGRK-UHFFFAOYSA-N 6-methyl-3-(1-propyltetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCN1N=NN=C1C(C1=O)=CN=C2N1C(C)=CC=C2 VGMDPUAUNOKGRK-UHFFFAOYSA-N 0.000 description 2
- NRDKLCINVVDIJT-UHFFFAOYSA-N 9-methyl-3-(1-methyltetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CC1=CC=CN(C2=O)C1=NC=C2C1=NN=NN1C NRDKLCINVVDIJT-UHFFFAOYSA-N 0.000 description 2
- GVWDJYRYKJRTII-UHFFFAOYSA-N 9-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound CC1=CC=CN2C1=NC=CC2=O GVWDJYRYKJRTII-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 208000007107 Stomach Ulcer Diseases 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- ZUZMMWXMHNDRLQ-UHFFFAOYSA-N methyl 5-(4-oxopyrido[1,2-a]pyrimidin-3-yl)tetrazole-1-carboxylate Chemical compound COC(=O)N1N=NN=C1C(C1=O)=CN=C2N1C=CC=C2 ZUZMMWXMHNDRLQ-UHFFFAOYSA-N 0.000 description 2
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 230000036269 ulceration Effects 0.000 description 2
- YZIFVWOCPGPNHB-UHFFFAOYSA-N 1,2-dichloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C(Cl)=C1 YZIFVWOCPGPNHB-UHFFFAOYSA-N 0.000 description 1
- YLRBJYMANQKEAW-UHFFFAOYSA-N 1-bromo-4-(bromomethyl)benzene Chemical compound BrCC1=CC=C(Br)C=C1 YLRBJYMANQKEAW-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
- BHEMTARGRZWOQN-UHFFFAOYSA-N 2-[(4-nitrophenyl)methyl]tetrazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1CN1N=NC=N1 BHEMTARGRZWOQN-UHFFFAOYSA-N 0.000 description 1
- BGRKDLVBPMCBJW-UHFFFAOYSA-N 2-ethyltetrazole Chemical compound CCN1N=CN=N1 BGRKDLVBPMCBJW-UHFFFAOYSA-N 0.000 description 1
- OQUFOZNPBIIJTN-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;sodium Chemical compound [Na].OC(=O)CC(O)(C(O)=O)CC(O)=O OQUFOZNPBIIJTN-UHFFFAOYSA-N 0.000 description 1
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
- WAWWZQNTXKPLRL-UHFFFAOYSA-N 3-(1-cyclopentyltetrazol-5-yl)-9-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound CC1=CC=CN(C2=O)C1=NC=C2C1=NN=NN1C1CCCC1 WAWWZQNTXKPLRL-UHFFFAOYSA-N 0.000 description 1
- ZMJINVDEIBYACB-UHFFFAOYSA-N 3-(1-ethyltetrazol-5-yl)-9-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound CCN1N=NN=C1C(C1=O)=CN=C2N1C=CC=C2C ZMJINVDEIBYACB-UHFFFAOYSA-N 0.000 description 1
- VXLBOTGUKFKVLV-UHFFFAOYSA-N 3-(1-propan-2-yltetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CC(C)N1N=NN=C1C(C1=O)=CN=C2N1C=CC=C2 VXLBOTGUKFKVLV-UHFFFAOYSA-N 0.000 description 1
- XYJTTXWOSPWPBN-UHFFFAOYSA-N 3-(1-propyltetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCN1N=NN=C1C(C1=O)=CN=C2N1C=CC=C2 XYJTTXWOSPWPBN-UHFFFAOYSA-N 0.000 description 1
- RDILCDJJJFZTGD-UHFFFAOYSA-N 3-(2-butyltetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCN1N=NC(C=2C(N3C=CC=CC3=NC=2)=O)=N1 RDILCDJJJFZTGD-UHFFFAOYSA-N 0.000 description 1
- JLWCYHMLCOXZDW-UHFFFAOYSA-N 3-(2-cyclopentyltetrazol-5-yl)-9-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound CC1=CC=CN(C2=O)C1=NC=C2C(=N1)N=NN1C1CCCC1 JLWCYHMLCOXZDW-UHFFFAOYSA-N 0.000 description 1
- GKQNRLGTUUZPFC-UHFFFAOYSA-N 3-(2-ethyltetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCN1N=NC(C=2C(N3C=CC=CC3=NC=2)=O)=N1 GKQNRLGTUUZPFC-UHFFFAOYSA-N 0.000 description 1
- CMAJTMKPHHZJQL-UHFFFAOYSA-N 3-(2-methyltetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CN1N=NC(C=2C(N3C=CC=CC3=NC=2)=O)=N1 CMAJTMKPHHZJQL-UHFFFAOYSA-N 0.000 description 1
- LAFBCSYHONXKHK-UHFFFAOYSA-N 3-[1-[(4-chlorophenyl)methyl]tetrazol-5-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1CN1C(C=2C(N3C=CC=CC3=NC=2)=O)=NN=N1 LAFBCSYHONXKHK-UHFFFAOYSA-N 0.000 description 1
- LANITNFNPRGYMD-UHFFFAOYSA-N 3-[2-(2-methylpropyl)tetrazol-5-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CC(C)CN1N=NC(C=2C(N3C=CC=CC3=NC=2)=O)=N1 LANITNFNPRGYMD-UHFFFAOYSA-N 0.000 description 1
- DAMPMRDGEYZAFV-UHFFFAOYSA-N 3-[2-[(4-chlorophenyl)methyl]tetrazol-5-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1CN1N=C(C=2C(N3C=CC=CC3=NC=2)=O)N=N1 DAMPMRDGEYZAFV-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 1
- VTEOBYZEHQZZKT-UHFFFAOYSA-N 6-methyl-3-(1-methyltetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound O=C1N2C(C)=CC=CC2=NC=C1C1=NN=NN1C VTEOBYZEHQZZKT-UHFFFAOYSA-N 0.000 description 1
- VKHNHADDMLRPCA-UHFFFAOYSA-N 6-methyl-3-(1-pentyltetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCCN1N=NN=C1C(C1=O)=CN=C2N1C(C)=CC=C2 VKHNHADDMLRPCA-UHFFFAOYSA-N 0.000 description 1
- FQOLPGJLMXLTDJ-UHFFFAOYSA-N 6-methyl-3-(2-propan-2-yltetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CC(C)N1N=NC(C=2C(N3C(C)=CC=CC3=NC=2)=O)=N1 FQOLPGJLMXLTDJ-UHFFFAOYSA-N 0.000 description 1
- OYKXXDRNBFOWGB-UHFFFAOYSA-N 6-methyl-3-(2-propyltetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCN1N=NC(C=2C(N3C(C)=CC=CC3=NC=2)=O)=N1 OYKXXDRNBFOWGB-UHFFFAOYSA-N 0.000 description 1
- CJPFVFYOKDJVCX-UHFFFAOYSA-N 6-methyl-3-[1-[(4-nitrophenyl)methyl]tetrazol-5-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound O=C1N2C(C)=CC=CC2=NC=C1C1=NN=NN1CC1=CC=C([N+]([O-])=O)C=C1 CJPFVFYOKDJVCX-UHFFFAOYSA-N 0.000 description 1
- VPQJECKKYRMMMK-UHFFFAOYSA-N 9-methyl-3-(1-prop-2-ynyltetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CC1=CC=CN(C2=O)C1=NC=C2C1=NN=NN1CC#C VPQJECKKYRMMMK-UHFFFAOYSA-N 0.000 description 1
- RDOMYEDOUXBCJP-UHFFFAOYSA-N 9-methyl-3-(1-propyltetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCN1N=NN=C1C(C1=O)=CN=C2N1C=CC=C2C RDOMYEDOUXBCJP-UHFFFAOYSA-N 0.000 description 1
- FXCDVGKNSZAZFS-UHFFFAOYSA-N 9-methyl-3-(2-prop-2-ynyltetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CC1=CC=CN(C2=O)C1=NC=C2C=1N=NN(CC#C)N=1 FXCDVGKNSZAZFS-UHFFFAOYSA-N 0.000 description 1
- DJQBYXKYQXHFGY-UHFFFAOYSA-N 9-methyl-3-(2-propan-2-yltetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CC(C)N1N=NC(C=2C(N3C=CC=C(C)C3=NC=2)=O)=N1 DJQBYXKYQXHFGY-UHFFFAOYSA-N 0.000 description 1
- UTJMUBBBNMPTML-UHFFFAOYSA-N 9-methyl-3-(2-propyltetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one;hydrochloride Chemical compound Cl.CCCN1N=NC(C=2C(N3C=CC=C(C)C3=NC=2)=O)=N1 UTJMUBBBNMPTML-UHFFFAOYSA-N 0.000 description 1
- WXWWEFZPRLRGFL-UHFFFAOYSA-N 9-methyl-3-(2h-tetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one;potassium Chemical compound [K].CC1=CC=CN(C2=O)C1=NC=C2C1=NN=NN1 WXWWEFZPRLRGFL-UHFFFAOYSA-N 0.000 description 1
- HQNOOINDPVPMOP-UHFFFAOYSA-N 9-methyl-3-[1-(1-phenylethyl)tetrazol-5-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound N1=NN=C(C=2C(N3C=CC=C(C)C3=NC=2)=O)N1C(C)C1=CC=CC=C1 HQNOOINDPVPMOP-UHFFFAOYSA-N 0.000 description 1
- IGNPZUGJOVUOSG-UHFFFAOYSA-N 9-methyl-3-[1-(2-methylpropyl)tetrazol-5-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CC(C)CN1N=NN=C1C(C1=O)=CN=C2N1C=CC=C2C IGNPZUGJOVUOSG-UHFFFAOYSA-N 0.000 description 1
- FJXOVZAJYHNCKK-UHFFFAOYSA-N 9-methyl-3-[1-(3-methylbutyl)tetrazol-5-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CC(C)CCN1N=NN=C1C(C1=O)=CN=C2N1C=CC=C2C FJXOVZAJYHNCKK-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- RUARIYVAIZJNEZ-UHFFFAOYSA-N C(CCC)N1N=C(N=N1)C1=CN=C2N(C1=O)C=CC=C2C Chemical compound C(CCC)N1N=C(N=N1)C1=CN=C2N(C1=O)C=CC=C2C RUARIYVAIZJNEZ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- PIMWEADLSLQGIL-UHFFFAOYSA-N Cl.C(C)(C)N1N=C(N=N1)C1=CN=C2N(C1=O)C=CC=C2C Chemical compound Cl.C(C)(C)N1N=C(N=N1)C1=CN=C2N(C1=O)C=CC=C2C PIMWEADLSLQGIL-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 206010061164 Gastric mucosal lesion Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- BRTFVKHPEHKBQF-UHFFFAOYSA-N bromocyclopentane Chemical compound BrC1CCCC1 BRTFVKHPEHKBQF-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- XLBRAOZPILSVOH-UHFFFAOYSA-N methanesulfonic acid;9-methyl-3-(2-propyltetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CS(O)(=O)=O.CCCN1N=NC(C=2C(N3C=CC=C(C)C3=NC=2)=O)=N1 XLBRAOZPILSVOH-UHFFFAOYSA-N 0.000 description 1
- XQDDLDRCJQAHAY-UHFFFAOYSA-N methyl 5-(4-oxopyrido[1,2-a]pyrimidin-3-yl)tetrazole-2-carboxylate Chemical compound COC(=O)N1N=NC(C=2C(N3C=CC=CC3=NC=2)=O)=N1 XQDDLDRCJQAHAY-UHFFFAOYSA-N 0.000 description 1
- YMUYMNFNXOYJLB-UHFFFAOYSA-N methyl 5-(9-methyl-4-oxopyrido[1,2-a]pyrimidin-3-yl)-1,3-dihydrotetrazole-2-carboxylate Chemical compound N1N(C(=O)OC)NN=C1C(C1=O)=CN=C2N1C=CC=C2C YMUYMNFNXOYJLB-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 230000009854 mucosal lesion Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- KGCNHWXDPDPSBV-UHFFFAOYSA-N p-nitrobenzyl chloride Chemical compound [O-][N+](=O)C1=CC=C(CCl)C=C1 KGCNHWXDPDPSBV-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 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
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU620590A HU209793B (en) | 1990-09-25 | 1990-09-25 | Process for the production of pyrido[1,2-a]pyrimidine-derivatives and pharmaceutical compositions containing the same |
| PCT/HU1992/000031 WO1993004065A1 (en) | 1990-09-25 | 1992-08-13 | NEW 3-(SUBSTITUTED TETRAZOLYL)-4-OXO-4H-PYRIDO-[1,2-a]PYRIMIDINES, SALTS THEREOF, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND PROCESS FOR PREPARING SAME |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK16594A3 true SK16594A3 (en) | 1994-08-10 |
Family
ID=10971360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK165-94A SK16594A3 (en) | 1990-09-25 | 1992-08-13 | New 3-substituded tetrazolyl-4-oxo-4h-pyrido[1,2-a] pyrimidines derivatives |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5475000A (enExample) |
| EP (1) | EP0641340A1 (enExample) |
| JP (1) | JPH06509800A (enExample) |
| CN (1) | CN1071925A (enExample) |
| AU (1) | AU663886B2 (enExample) |
| BG (1) | BG98448A (enExample) |
| CA (1) | CA2114145A1 (enExample) |
| CZ (1) | CZ27694A3 (enExample) |
| EE (1) | EE9400115A (enExample) |
| FI (1) | FI940591A7 (enExample) |
| HU (1) | HU209793B (enExample) |
| IL (1) | IL102788A (enExample) |
| MX (1) | MX9204659A (enExample) |
| PT (1) | PT100774A (enExample) |
| SI (1) | SI9200172A (enExample) |
| SK (1) | SK16594A3 (enExample) |
| TW (1) | TW222632B (enExample) |
| WO (1) | WO1993004065A1 (enExample) |
| YU (1) | YU76092A (enExample) |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3055911A (en) * | 1958-04-29 | 1962-09-25 | William G Finnegan | Substituted tetrazoles |
| US4122274A (en) * | 1977-05-25 | 1978-10-24 | Bristol-Myers Company | 3-Tetrazolo-5,6,7,8-substituted-pyrido[1,2-a]pyrimidin-4-ones |
| JPS5536447A (en) * | 1978-09-07 | 1980-03-14 | Otsuka Pharmaceut Co Ltd | Butyramide derivative |
| US4432986A (en) * | 1979-06-18 | 1984-02-21 | Riker Laboratories, Inc. | Tetrazoles bonded to certain polycyclic aromatic systems and anti-allergic use thereof |
| US4474792A (en) * | 1979-06-18 | 1984-10-02 | Riker Laboratories, Inc. | N-Tetrazolyl benzamides and anti-allergic use thereof |
| FI73423C (fi) * | 1980-02-29 | 1987-10-09 | Otsuka Pharma Co Ltd | Foerfarande foer framstaellning av farmakologiskt verksamma tetrazolderivat. |
| US4457932A (en) * | 1983-07-22 | 1984-07-03 | Bristol-Myers Company | Anti-ulcer agents |
| FR2549831A1 (fr) * | 1983-07-27 | 1985-02-01 | Rhone Poulenc Agrochimie | Nouveaux derives d'acides aryloxybenzoiques, et leur utilisation comme herbicides |
| US4845227A (en) * | 1984-06-18 | 1989-07-04 | Eli Lilly And Company | Aromatase inhibitors from azoles |
| US5237070A (en) * | 1985-07-22 | 1993-08-17 | Riker Laboratories, Inc. | Substituted DI-t-butylphenols |
| US5049572A (en) * | 1987-04-06 | 1991-09-17 | Riker Laboratories, Inc. | Substituted di-t-butylphenols and anti-allergic use thereof |
| JP2668259B2 (ja) * | 1988-02-18 | 1997-10-27 | 塩野義製薬株式会社 | 複素環化合物および抗潰瘍剤 |
| HUT64064A (en) * | 1992-02-13 | 1993-11-29 | Chinoin Gyogyszer Es Vegyeszet | Process for producing puyrido/1,2-a/pyrimidine derivatives and pharmaceutical compositions comprising same as active ingredient |
-
1990
- 1990-09-25 HU HU620590A patent/HU209793B/hu not_active IP Right Cessation
-
1992
- 1992-08-07 YU YU76092A patent/YU76092A/sh unknown
- 1992-08-11 IL IL10278892A patent/IL102788A/en not_active IP Right Cessation
- 1992-08-12 MX MX9204659A patent/MX9204659A/es unknown
- 1992-08-13 US US08/193,080 patent/US5475000A/en not_active Expired - Fee Related
- 1992-08-13 CA CA002114145A patent/CA2114145A1/en not_active Abandoned
- 1992-08-13 SK SK165-94A patent/SK16594A3/sk unknown
- 1992-08-13 JP JP5504219A patent/JPH06509800A/ja active Pending
- 1992-08-13 PT PT100774A patent/PT100774A/pt not_active Application Discontinuation
- 1992-08-13 AU AU24628/92A patent/AU663886B2/en not_active Ceased
- 1992-08-13 WO PCT/HU1992/000031 patent/WO1993004065A1/en not_active Ceased
- 1992-08-13 EP EP92917915A patent/EP0641340A1/en not_active Withdrawn
- 1992-08-13 SI SI19929200172A patent/SI9200172A/sl unknown
- 1992-08-13 CN CN92110634A patent/CN1071925A/zh active Pending
- 1992-09-19 TW TW081107387A patent/TW222632B/zh active
-
1994
- 1994-02-09 FI FI940591A patent/FI940591A7/fi not_active Application Discontinuation
- 1994-02-09 CZ CZ94276A patent/CZ27694A3/cs unknown
- 1994-02-10 BG BG98448A patent/BG98448A/xx unknown
- 1994-08-10 EE EE9400115A patent/EE9400115A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUT64954A (en) | 1994-03-28 |
| TW222632B (enExample) | 1994-04-21 |
| JPH06509800A (ja) | 1994-11-02 |
| BG98448A (bg) | 1994-11-15 |
| EE9400115A (et) | 1995-12-15 |
| IL102788A (en) | 1996-03-31 |
| SI9200172A (en) | 1993-03-31 |
| HU906205D0 (en) | 1991-03-28 |
| YU76092A (sr) | 1996-01-09 |
| CN1071925A (zh) | 1993-05-12 |
| FI940591A0 (fi) | 1994-02-09 |
| MX9204659A (es) | 1993-12-31 |
| AU663886B2 (en) | 1995-10-26 |
| EP0641340A1 (en) | 1995-03-08 |
| CZ27694A3 (en) | 1994-08-17 |
| CA2114145A1 (en) | 1993-03-04 |
| FI940591A7 (fi) | 1994-02-09 |
| US5475000A (en) | 1995-12-12 |
| WO1993004065A1 (en) | 1993-03-04 |
| AU2462892A (en) | 1993-03-16 |
| PT100774A (pt) | 1993-10-29 |
| HU209793B (en) | 1994-11-28 |
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