FI67549C - Foerfarande foer framstaellning av 9-(substituerad-amino)-4-oxo-6,7-dihydro-4h-pyrido(1,2-a)pyrimidin-3-karboxylsyraderivat - Google Patents
Foerfarande foer framstaellning av 9-(substituerad-amino)-4-oxo-6,7-dihydro-4h-pyrido(1,2-a)pyrimidin-3-karboxylsyraderivat Download PDFInfo
- Publication number
- FI67549C FI67549C FI801511A FI801511A FI67549C FI 67549 C FI67549 C FI 67549C FI 801511 A FI801511 A FI 801511A FI 801511 A FI801511 A FI 801511A FI 67549 C FI67549 C FI 67549C
- Authority
- FI
- Finland
- Prior art keywords
- oxo
- pyrido
- pyrimidine
- methyl
- dihydro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 150000003839 salts Chemical group 0.000 claims description 9
- -1 9- (substituted-amino) -4-oxo-6,7-dihydro-4H-pyrido [1,2-a] pyrimidine-3-carboxylic acid Chemical class 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 150000004677 hydrates Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000002844 melting Methods 0.000 description 20
- 230000008018 melting Effects 0.000 description 20
- 239000000047 product Substances 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- QGVBBYJIRIGIIT-UHFFFAOYSA-N 9-anilino-6-methyl-4-oxo-6,7-dihydropyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C12=NC=C(C(O)=O)C(=O)N2C(C)CC=C1NC1=CC=CC=C1 QGVBBYJIRIGIIT-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 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 4
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000002516 radical scavenger Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YWLVFQUVWLTLJA-UHFFFAOYSA-N 9,9-dibromo-6-methyl-4-oxo-7,8-dihydro-6h-pyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)N2C(C)CCC(Br)(Br)C2=N1 YWLVFQUVWLTLJA-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- CSOYDALHEQEMAK-UHFFFAOYSA-N 2h-pyrimidine-1-carboxylic acid Chemical compound OC(=O)N1CN=CC=C1 CSOYDALHEQEMAK-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910052740 iodine Chemical group 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- HLERUSAEASQGKG-UHFFFAOYSA-N 2,6-dibromo-6-methyl-4-oxo-8,9-dihydro-7H-pyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound BrC1(CCCC=2N1C(C(=C(N=2)Br)C(=O)O)=O)C HLERUSAEASQGKG-UHFFFAOYSA-N 0.000 description 1
- WELIVEBWRWAGOM-UHFFFAOYSA-N 3-amino-n-[2-[2-(3-aminopropanoylamino)ethyldisulfanyl]ethyl]propanamide Chemical compound NCCC(=O)NCCSSCCNC(=O)CCN WELIVEBWRWAGOM-UHFFFAOYSA-N 0.000 description 1
- KOXNRJHZWXSKMF-UHFFFAOYSA-N 6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)N2C(C)CCCC2=N1 KOXNRJHZWXSKMF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WJAMXEPOSKIQNN-UHFFFAOYSA-N 9,9-dibromo-6-methyl-4-oxo-7,8-dihydro-6h-pyrido[1,2-a]pyrimidine-3-carbonitrile Chemical compound C1=C(C#N)C(=O)N2C(C)CCC(Br)(Br)C2=N1 WJAMXEPOSKIQNN-UHFFFAOYSA-N 0.000 description 1
- YHTRJLYVAGCNAK-UHFFFAOYSA-N 9,9-dibromo-6-methyl-7,8-dihydro-6h-pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC(=O)N2C(C)CCC(Br)(Br)C2=N1 YHTRJLYVAGCNAK-UHFFFAOYSA-N 0.000 description 1
- VNYHORWRAFWGHB-UHFFFAOYSA-N 9,9-dibromo-8-methyl-4-oxo-7,8-dihydro-6H-pyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound BrC1(C(CCN2C1=NC=C(C2=O)C(=O)O)C)Br VNYHORWRAFWGHB-UHFFFAOYSA-N 0.000 description 1
- TZOBDIKCZMHEPQ-UHFFFAOYSA-N 9-(benzylamino)-6-methyl-4-oxo-6,7-dihydropyrido[1,2-a]pyrimidine-3-carboxamide Chemical compound C(C1=CC=CC=C1)NC1=CCC(N2C1=NC=C(C2=O)C(=O)N)C TZOBDIKCZMHEPQ-UHFFFAOYSA-N 0.000 description 1
- SQAKEHWOXJPZGL-UHFFFAOYSA-N 9-(butylamino)-6-methyl-4-oxo-6,7-dihydropyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound CCCCNC1=CCC(C)N2C1=NC=C(C(O)=O)C2=O SQAKEHWOXJPZGL-UHFFFAOYSA-N 0.000 description 1
- BFFHWTMPHZNPDX-UHFFFAOYSA-N 9-anilino-4-oxo-6,7-dihydropyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C=1CCN2C(=O)C(C(=O)O)=CN=C2C=1NC1=CC=CC=C1 BFFHWTMPHZNPDX-UHFFFAOYSA-N 0.000 description 1
- LBGAWFWSIGIGOC-UHFFFAOYSA-N BrC1(CCC(N2C1=NC(=CC2=O)C(=O)O)C)Br Chemical compound BrC1(CCC(N2C1=NC(=CC2=O)C(=O)O)C)Br LBGAWFWSIGIGOC-UHFFFAOYSA-N 0.000 description 1
- MTJHABMXCIDLSU-UHFFFAOYSA-N BrC1(CCC(N2C1=NC=C(C2=O)C(=O)O)C)Br.C(C)OC(=O)C2=CN=C1N(C2=O)C(CCC1(Br)Br)C Chemical group BrC1(CCC(N2C1=NC=C(C2=O)C(=O)O)C)Br.C(C)OC(=O)C2=CN=C1N(C2=O)C(CCC1(Br)Br)C MTJHABMXCIDLSU-UHFFFAOYSA-N 0.000 description 1
- IONAPZNHJDWMQW-UHFFFAOYSA-N BrC1(CCCN2C1=NC=C(C2=O)C(=O)O)Br.BrC2(CCC(N1C2=NC=C(C1=O)C(=O)O)C)Br Chemical group BrC1(CCCN2C1=NC=C(C2=O)C(=O)O)Br.BrC2(CCC(N1C2=NC=C(C1=O)C(=O)O)C)Br IONAPZNHJDWMQW-UHFFFAOYSA-N 0.000 description 1
- NNKLVCNXGMSPPK-UHFFFAOYSA-N C1(=CC=CC=C1)NC1=C(CCN2C1=NC=C(C2=O)C(=O)O)C Chemical compound C1(=CC=CC=C1)NC1=C(CCN2C1=NC=C(C2=O)C(=O)O)C NNKLVCNXGMSPPK-UHFFFAOYSA-N 0.000 description 1
- AUZSASNPAJHAGA-UHFFFAOYSA-N C1(=CC=CC=C1)NC1=CCC(N2C1=NC=C(C2=O)C#N)C Chemical compound C1(=CC=CC=C1)NC1=CCC(N2C1=NC=C(C2=O)C#N)C AUZSASNPAJHAGA-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 240000006890 Erythroxylum coca Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 102100022769 POC1 centriolar protein homolog B Human genes 0.000 description 1
- 101710125069 POC1 centriolar protein homolog B Proteins 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000008957 cocaer Nutrition 0.000 description 1
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- PZRGKPUNLYQYPK-UHFFFAOYSA-N ethyl 6-methyl-9-(n-methylanilino)-4-oxo-6,7-dihydropyrido[1,2-a]pyrimidine-3-carboxylate Chemical compound C=1CC(C)N2C(=O)C(C(=O)OCC)=CN=C2C=1N(C)C1=CC=CC=C1 PZRGKPUNLYQYPK-UHFFFAOYSA-N 0.000 description 1
- PAVAOTMMHDGALM-UHFFFAOYSA-N ethyl 9,9-dibromo-6-methyl-4-oxo-7,8-dihydro-6h-pyrido[1,2-a]pyrimidine-3-carboxylate Chemical compound O=C1C(C(=O)OCC)=CN=C2N1C(C)CCC2(Br)Br PAVAOTMMHDGALM-UHFFFAOYSA-N 0.000 description 1
- ZMOWLJVWJYBTLK-UHFFFAOYSA-N ethyl 9-anilino-6-methyl-4-oxo-6,7-dihydropyrido[1,2-a]pyrimidine-3-carboxylate Chemical compound C=1CC(C)N2C(=O)C(C(=O)OCC)=CN=C2C=1NC1=CC=CC=C1 ZMOWLJVWJYBTLK-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 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
- 239000008096 xylene Substances 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
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI001933 | 1979-05-11 | ||
| HU79CI1933A HU178452B (en) | 1979-05-11 | 1979-05-11 | Process for preparing 9-substituted amino-4-oxo-6,7-dihydro-4h-pyrido/1,2-a/pyrimidine derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI801511A7 FI801511A7 (fi) | 1980-11-12 |
| FI67549B FI67549B (fi) | 1984-12-31 |
| FI67549C true FI67549C (fi) | 1985-04-10 |
Family
ID=10994748
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI801511A FI67549C (fi) | 1979-05-11 | 1980-05-09 | Foerfarande foer framstaellning av 9-(substituerad-amino)-4-oxo-6,7-dihydro-4h-pyrido(1,2-a)pyrimidin-3-karboxylsyraderivat |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4452982A (cs) |
| JP (1) | JPS5618981A (cs) |
| AT (1) | AT375938B (cs) |
| AU (1) | AU546194B2 (cs) |
| BE (1) | BE883218A (cs) |
| CA (1) | CA1140124A (cs) |
| CH (1) | CH653335A5 (cs) |
| CS (1) | CS236752B2 (cs) |
| DD (1) | DD150604A5 (cs) |
| DE (1) | DE3017560A1 (cs) |
| DK (1) | DK204980A (cs) |
| ES (1) | ES8105004A1 (cs) |
| FI (1) | FI67549C (cs) |
| FR (1) | FR2456100B1 (cs) |
| GB (1) | GB2051784B (cs) |
| HU (1) | HU178452B (cs) |
| IL (1) | IL59968A (cs) |
| IT (1) | IT8067718A0 (cs) |
| LU (1) | LU82434A1 (cs) |
| NL (1) | NL8002679A (cs) |
| PL (1) | PL127344B1 (cs) |
| PT (1) | PT71214A (cs) |
| SE (1) | SE441748B (cs) |
| SU (1) | SU1024007A3 (cs) |
| YU (1) | YU122180A (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU178453B (en) * | 1979-05-11 | 1982-05-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing 9-hydrazino-4-oxo-6,7,8,9-tetrahydro-4h-p-pyrido-square bracket-1,2-a-square bracket closed-pyrimidine derivatives |
| US5252572A (en) * | 1988-02-03 | 1993-10-12 | Chinoin Gyogyszer- Es Vegyeszeti Termekek Gyara Rt. | Pyridopyrimidine derivatives, pharmaceutical compositions containing them and process for preparing same |
| JP4747414B2 (ja) * | 1999-11-09 | 2011-08-17 | 株式会社セガ | キーボード取付構造を有するビデオゲーム機 |
| AU2003270783C1 (en) * | 2002-09-20 | 2010-05-20 | Merck Sharp & Dohme Corp. | Octahydro-2-H-naphtho[1,2-F] indole-4-carboxamide derivatives as selective glucocorticoid receptor modulators |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3141043A (en) * | 1961-03-24 | 1964-07-14 | Purdue Research Foundation | Cyclopentadienylimines, process for their production and condensation products thereof |
| AT296996B (de) * | 1966-11-02 | 1972-03-10 | Chinoin Gyogyszer Es Vegyeszet | Verfahren zur Herstellung von Homopyrimidazolderivaten und deren Säureadditionssalzen und quaternären Ammoniumsalzen |
| HU178496B (en) * | 1977-12-29 | 1982-05-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing 6,7,8,9-tetrahydro-4h-pyrido/1,2-a/pyrimidine derivatives with antiallergic activity |
| HU180439B (en) * | 1977-12-29 | 1983-03-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing 9-amino-pyrido-square bracket-1,2-a-square bracket closed-pyrimidine derivatives |
-
1979
- 1979-05-11 HU HU79CI1933A patent/HU178452B/hu unknown
-
1980
- 1980-05-01 IL IL59968A patent/IL59968A/xx unknown
- 1980-05-08 SE SE8003480A patent/SE441748B/sv not_active IP Right Cessation
- 1980-05-08 YU YU01221/80A patent/YU122180A/xx unknown
- 1980-05-08 CS CS803259A patent/CS236752B2/cs unknown
- 1980-05-08 SU SU802923101A patent/SU1024007A3/ru active
- 1980-05-08 DE DE19803017560 patent/DE3017560A1/de not_active Withdrawn
- 1980-05-09 LU LU82434A patent/LU82434A1/fr unknown
- 1980-05-09 IT IT8067718A patent/IT8067718A0/it unknown
- 1980-05-09 BE BE0/200551A patent/BE883218A/fr not_active IP Right Cessation
- 1980-05-09 DK DK204980A patent/DK204980A/da not_active Application Discontinuation
- 1980-05-09 AU AU58279/80A patent/AU546194B2/en not_active Ceased
- 1980-05-09 PT PT71214A patent/PT71214A/pt unknown
- 1980-05-09 CH CH3664/80A patent/CH653335A5/de not_active IP Right Cessation
- 1980-05-09 GB GB8015470A patent/GB2051784B/en not_active Expired
- 1980-05-09 FI FI801511A patent/FI67549C/fi not_active IP Right Cessation
- 1980-05-09 NL NL8002679A patent/NL8002679A/nl unknown
- 1980-05-09 FR FR8010480A patent/FR2456100B1/fr not_active Expired
- 1980-05-09 US US06/148,238 patent/US4452982A/en not_active Expired - Lifetime
- 1980-05-09 DD DD80220984A patent/DD150604A5/de unknown
- 1980-05-09 CA CA000351664A patent/CA1140124A/en not_active Expired
- 1980-05-09 JP JP6161480A patent/JPS5618981A/ja active Pending
- 1980-05-09 AT AT0247780A patent/AT375938B/de not_active IP Right Cessation
- 1980-05-10 PL PL1980224164A patent/PL127344B1/pl unknown
- 1980-05-10 ES ES491770A patent/ES8105004A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES491770A0 (es) | 1981-06-01 |
| PT71214A (en) | 1980-06-01 |
| DD150604A5 (de) | 1981-09-09 |
| YU122180A (en) | 1983-02-28 |
| FI801511A7 (fi) | 1980-11-12 |
| CH653335A5 (de) | 1985-12-31 |
| US4452982A (en) | 1984-06-05 |
| IT8067718A0 (it) | 1980-05-09 |
| NL8002679A (nl) | 1980-11-13 |
| ATA247780A (de) | 1984-02-15 |
| SE8003480L (sv) | 1980-11-12 |
| FR2456100A1 (fr) | 1980-12-05 |
| ES8105004A1 (es) | 1981-06-01 |
| CS236752B2 (en) | 1985-05-15 |
| DE3017560A1 (de) | 1980-11-13 |
| PL224164A1 (cs) | 1981-02-13 |
| FI67549B (fi) | 1984-12-31 |
| LU82434A1 (fr) | 1980-07-31 |
| AU5827980A (en) | 1980-11-13 |
| SU1024007A3 (ru) | 1983-06-15 |
| JPS5618981A (en) | 1981-02-23 |
| GB2051784B (en) | 1983-03-02 |
| IL59968A0 (en) | 1980-07-31 |
| DK204980A (da) | 1980-11-12 |
| IL59968A (en) | 1984-05-31 |
| SE441748B (sv) | 1985-11-04 |
| GB2051784A (en) | 1981-01-21 |
| PL127344B1 (en) | 1983-10-31 |
| HU178452B (en) | 1982-05-28 |
| AU546194B2 (en) | 1985-08-22 |
| CA1140124A (en) | 1983-01-25 |
| AT375938B (de) | 1984-09-25 |
| BE883218A (fr) | 1980-09-01 |
| FR2456100B1 (fr) | 1985-08-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: CHINOIN GYOGUSZER ES VEGYESZETI TERMEKEK |