SU1022659A3 - Способ получени производных пиридо (1,2- @ ) пиримидина или их кислотно-аддитивных солей - Google Patents

Способ получени производных пиридо (1,2- @ ) пиримидина или их кислотно-аддитивных солей Download PDF

Info

Publication number: SU1022659A3
Authority: SU; USSR - Soviet Union
Prior art keywords: acid; hydrogen; pyrimidine; oxo; pyrido
Prior art date: 1977-12-29

Application number

SU782700554A

Other languages

English (en)

Russian (ru)

Inventor

Хермец Иштван

Месарош Золтан

Вашвари Лелле

Хорват Агнеш

Original Assignee

Хиноин Дьедьсер Еш Ведьесети Термекек Дъяра Рт (Инопредприятие)

Priority date (The priority date 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 date listed.)

1977-12-29

Filing date

1978-12-25

Publication date

1983-06-07

1978-12-25 Application filed by Хиноин Дьедьсер Еш Ведьесети Термекек Дъяра Рт (Инопредприятие) filed Critical Хиноин Дьедьсер Еш Ведьесети Термекек Дъяра Рт (Инопредприятие)

1983-06-07 Application granted granted Critical

1983-06-07 Publication of SU1022659A3 publication Critical patent/SU1022659A3/ru

Links

238000000034 method Methods 0.000 title claims description 23
239000002253 acid Substances 0.000 title claims description 22
150000003839 salts Chemical class 0.000 title claims description 7
239000000654 additive Substances 0.000 title description 2
230000000996 additive effect Effects 0.000 title description 2
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
239000001257 hydrogen Substances 0.000 claims abstract description 18
150000001875 compounds Chemical class 0.000 claims abstract description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
239000000203 mixture Substances 0.000 claims description 29
238000007363 ring formation reaction Methods 0.000 claims description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
239000000047 product Substances 0.000 claims description 10
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 8
239000003054 catalyst Substances 0.000 claims description 7
229920000137 polyphosphoric acid Polymers 0.000 claims description 6
MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 5
229910052763 palladium Inorganic materials 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
230000002378 acidificating effect Effects 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
239000005662 Paraffin oil Substances 0.000 claims description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 3
238000005984 hydrogenation reaction Methods 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
239000007859 condensation product Substances 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
125000000217 alkyl group Chemical group 0.000 claims 2
XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
239000007858 starting material Substances 0.000 abstract description 14
ICSNLGPSRYBMBD-UHFFFAOYSA-N alpha-aminopyridine Natural products NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 abstract description 4
VFMCUTPRJLZEEW-UHFFFAOYSA-N 4h-pyrido[1,2-a]pyrimidine Chemical class C1=CC=CN2CC=CN=C21 VFMCUTPRJLZEEW-UHFFFAOYSA-N 0.000 abstract description 3
239000000543 intermediate Substances 0.000 abstract description 3
150000003930 2-aminopyridines Chemical class 0.000 abstract description 2
239000000126 substance Substances 0.000 abstract description 2
125000000962 organic group Chemical group 0.000 abstract 1
230000000144 pharmacologic effect Effects 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
-1 C-C4-alkyl Chemical group 0.000 description 22
125000004494 ethyl ester group Chemical group 0.000 description 16
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
239000000155 melt Substances 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
239000013078 crystal Substances 0.000 description 7
230000008018 melting Effects 0.000 description 7
238000002844 melting Methods 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
238000009835 boiling Methods 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 4
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
230000015572 biosynthetic process Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
FHARGMSSJPHLMO-UHFFFAOYSA-N 2-(2h-pyrimidin-1-yl)acetic acid Chemical compound OC(=O)CN1CN=CC=C1 FHARGMSSJPHLMO-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-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
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
KINYSOSBLZADNX-UHFFFAOYSA-N ethyl 3-acetyl-4-oxopyrido[1,2-a]pyrimidine-9-carboxylate Chemical compound CCOC(=O)C1=CC=CN2C1=NC=C(C(C)=O)C2=O KINYSOSBLZADNX-UHFFFAOYSA-N 0.000 description 2
GTVZYZXAOMRCCB-UHFFFAOYSA-N ethyl 5-amino-3-oxopent-4-enoate Chemical compound C(C)OC(CC(=O)C=CN)=O GTVZYZXAOMRCCB-UHFFFAOYSA-N 0.000 description 2
FIKVWPJKNMTBBD-UHFFFAOYSA-N ethyl 6-aminopyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC=C(N)N=C1 FIKVWPJKNMTBBD-UHFFFAOYSA-N 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000003921 oil Substances 0.000 description 2
229960003424 phenylacetic acid Drugs 0.000 description 2
239000003279 phenylacetic acid Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
YPOXGDJGKBXRFP-UHFFFAOYSA-N pyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=N1 YPOXGDJGKBXRFP-UHFFFAOYSA-N 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
LAAGXYIBSJMFCU-UHFFFAOYSA-N 2-methyl-4-oxopyrido[1,2-a]pyrimidine-7-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=NC(C)=CC(=O)N21 LAAGXYIBSJMFCU-UHFFFAOYSA-N 0.000 description 1
DWVRHHMREUOGFX-UHFFFAOYSA-N 2-methyl-4-oxopyrido[1,2-a]pyrimidine-9-carboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=NC(C)=CC(=O)N21 DWVRHHMREUOGFX-UHFFFAOYSA-N 0.000 description 1
NLNGTEGRUVLYBX-UHFFFAOYSA-N 2h-pyrimidine-1,4-dicarboxylic acid Chemical compound OC(=O)N1CN=C(C(O)=O)C=C1 NLNGTEGRUVLYBX-UHFFFAOYSA-N 0.000 description 1
FEVRXPAVKXZDPQ-UHFFFAOYSA-N 2h-pyrimidine-1,5-dicarboxylic acid Chemical compound OC(=O)N1CN=CC(C(O)=O)=C1 FEVRXPAVKXZDPQ-UHFFFAOYSA-N 0.000 description 1
GOMRDTNNYBINCH-UHFFFAOYSA-N 3-cyano-4-oxopyrido[1,2-a]pyrimidine-8-carboxylic acid Chemical compound C1=C(C(=O)O)C=CN2C1=NC=C(C#N)C2=O GOMRDTNNYBINCH-UHFFFAOYSA-N 0.000 description 1
NECNSGIEEXDQJK-UHFFFAOYSA-N 4-oxopyrido[1,2-a]pyrimidine-9-carboxylic acid Chemical class OC(=O)C1=CC=CN2C1=NC=CC2=O NECNSGIEEXDQJK-UHFFFAOYSA-N 0.000 description 1
FPXDWQCNXFONMN-UHFFFAOYSA-N 4h-pyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C1=CC=CN2CC(C(=O)O)=CN=C21 FPXDWQCNXFONMN-UHFFFAOYSA-N 0.000 description 1
KSONDAXLKNQLTD-UHFFFAOYSA-N C(C)C1=CC=C(C=2N1C(C(=C(N2)CC)C(=O)O)=O)C(=O)O Chemical compound C(C)C1=CC=C(C=2N1C(C(=C(N2)CC)C(=O)O)=O)C(=O)O KSONDAXLKNQLTD-UHFFFAOYSA-N 0.000 description 1
SJMLHNQFZUDGCG-UHFFFAOYSA-N C(C)OC(=O)C1CCCN2C1=NC=C(C2=O)C#N Chemical compound C(C)OC(=O)C1CCCN2C1=NC=C(C2=O)C#N SJMLHNQFZUDGCG-UHFFFAOYSA-N 0.000 description 1
QTUPUPWXBDJVTI-UHFFFAOYSA-N C(C)OC(=O)C=1C=CC=2N(C(C=C(N2)C2=CC=CC=C2)=O)C1 Chemical compound C(C)OC(=O)C=1C=CC=2N(C(C=C(N2)C2=CC=CC=C2)=O)C1 QTUPUPWXBDJVTI-UHFFFAOYSA-N 0.000 description 1
GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 1
DULCUDSUACXJJC-UHFFFAOYSA-N Ethyl phenylacetate Chemical compound CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 description 1
LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 description 1
YTDAKAUOCHMPSQ-UHFFFAOYSA-N NC=CC(CC(=O)O)=O Chemical compound NC=CC(CC(=O)O)=O YTDAKAUOCHMPSQ-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 1
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
229940005991 chloric acid Drugs 0.000 description 1
QBPFLULOKWLNNW-UHFFFAOYSA-N chrysazin Chemical compound O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O QBPFLULOKWLNNW-UHFFFAOYSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000000378 dietary effect Effects 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
KIAGEDYOPMHRRB-UHFFFAOYSA-N ethyl 2-aminopyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC=CN=C1N KIAGEDYOPMHRRB-UHFFFAOYSA-N 0.000 description 1
XVBZFXZNJAFCHL-UHFFFAOYSA-N ethyl 2-aminopyridine-4-carboxylate Chemical compound CCOC(=O)C1=CC=NC(N)=C1 XVBZFXZNJAFCHL-UHFFFAOYSA-N 0.000 description 1
ZUBMZHJPTYYMRG-UHFFFAOYSA-N ethyl 3-amino-2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=CN ZUBMZHJPTYYMRG-UHFFFAOYSA-N 0.000 description 1
VFKWUZBDWZFVLF-UHFFFAOYSA-N ethyl 3-amino-2-phenylprop-2-enoate Chemical compound C(C)OC(C(=CN)C1=CC=CC=C1)=O VFKWUZBDWZFVLF-UHFFFAOYSA-N 0.000 description 1
DTYDENRYZSEGNL-UHFFFAOYSA-N ethyl 6-aminopyridine-2-carboxylate Chemical compound CCOC(=O)C1=CC=CC(N)=N1 DTYDENRYZSEGNL-UHFFFAOYSA-N 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
DWRWSNAREGLUHZ-UHFFFAOYSA-N ethyl pyrimidine-4-carboxylate Chemical compound CCOC(=O)C1=CC=NC=N1 DWRWSNAREGLUHZ-UHFFFAOYSA-N 0.000 description 1
239000000374 eutectic mixture Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000004907 flux Effects 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000005457 ice water Substances 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
150000002690 malonic acid derivatives Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
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 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 1
239000010690 paraffinic oil Substances 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
150000003151 propanoic acid esters Chemical class 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
NYJWYCAHJRGKMI-UHFFFAOYSA-N pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC=CN2C(=O)C=CN=C21 NYJWYCAHJRGKMI-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- 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

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Pain & Pain Management (AREA)
Neurosurgery (AREA)
Vascular Medicine (AREA)
Pulmonology (AREA)
Cardiology (AREA)
Hematology (AREA)
Anesthesiology (AREA)
Diabetes (AREA)
Urology & Nephrology (AREA)
Heart & Thoracic Surgery (AREA)
Immunology (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyridine Compounds (AREA)

SU782700554A 1977-12-29 1978-12-25 Способ получени производных пиридо (1,2- @ ) пиримидина или их кислотно-аддитивных солей SU1022659A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU77CI1796A HU180701B (en)	1977-12-29	1977-12-29	Process for preparing pyrido-/1,2-a/pyrimidines containing a carboxylic or ester group on the pirimidimering

Publications (1)

Publication Number	Publication Date
SU1022659A3 true SU1022659A3 (ru)	1983-06-07

Family

ID=10994685

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU782700554A SU1022659A3 (ru)	1977-12-29	1978-12-25	Способ получени производных пиридо (1,2- @ ) пиримидина или их кислотно-аддитивных солей

Country Status (8)

Country	Link
JP (1)	JPS5498797A (de)
BE (1)	BE873195A (de)
CH (1)	CH642368A5 (de)
DE (1)	DE2853273A1 (de)
FR (1)	FR2413375A1 (de)
GB (1)	GB2011410B (de)
HU (1)	HU180701B (de)
SU (1)	SU1022659A3 (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL59802A (en)	1979-05-08	1983-07-31	Erba Farmitalia	Substituted pyrido(1,2-a)pyrimidine carboxylic acid derivatives,their preparation and pharmaceutical compositions containing them
CN101628913B (zh) *	2008-07-18	2013-01-23	中国科学院广州生物医药与健康研究院	用作雌激素相关受体调节剂的化合物及其应用

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU168014B (de) *	1973-03-30	1976-02-28
US3898224A (en) *	1974-09-09	1975-08-05	Squibb & Sons Inc	1,6,7,8-Tetrahydro-4-oxo-4H-pyrido {8 1,2-A{9 pyrimidine-9-carboalkoxy compounds
HU173438B (hu) *	1975-11-27	1979-05-28	Chinoin Gyogyszer Es Vegyeszet	Sposob poluchenija novykh proizvodnykh 4-okso-1,6,7,8-/tetragidro-4h-pirido/1,2/pirimidina s zaderzhivajuhhejj vozgoranie aktivnot'ju i protivosvertivajuhhem effektom
HU174693B (hu) *	1976-02-12	1980-03-28	Chinoin Gyogyszer Es Vegyeszet	Sposob poluchenija kondensirovannykh proizvodnykh pirimidina
HU178910B (en) *	1977-08-19	1982-07-28	Chinoin Gyogyszer Es Vegyeszet	Process for preparing 2,3-disubstituted-4-oxo-4h-pyrido/1,2-a/-pyrimidines

1977
- 1977-12-29 HU HU77CI1796A patent/HU180701B/hu unknown
1978
- 1978-12-09 DE DE19782853273 patent/DE2853273A1/de not_active Ceased
- 1978-12-25 SU SU782700554A patent/SU1022659A3/ru active
- 1978-12-27 FR FR7836463A patent/FR2413375A1/fr active Granted
- 1978-12-27 JP JP16453378A patent/JPS5498797A/ja active Pending
- 1978-12-28 CH CH1323178A patent/CH642368A5/de not_active IP Right Cessation
- 1978-12-28 GB GB7850108A patent/GB2011410B/en not_active Expired
- 1978-12-29 BE BE192660A patent/BE873195A/xx not_active IP Right Cessation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
) 1. Vale II. L. and Spitzmiller E.R.. Tetrahydro-and Octahydropyr ido *

Also Published As

Publication number	Publication date
BE873195A (fr)	1979-04-17
GB2011410A (en)	1979-07-11
HU180701B (en)	1983-04-29
CH642368A5 (de)	1984-04-13
GB2011410B (en)	1982-09-22
DE2853273A1 (de)	1979-07-12
FR2413375B1 (de)	1983-08-05
FR2413375A1 (fr)	1979-07-27
JPS5498797A (en)	1979-08-03

Publication	Publication Date	Title
Althuis et al.	1979	Development of ethyl 3, 4-dihydro-4-oxopyrimido [4, 5-b] quinoline-2-carboxylate, a new prototype with oral antiallergy activity
WO1993007149A1 (en)	1993-04-15	Pyrazolopyrimidinone antianginal agents
Cheng et al.	1958	Potential Purine Antagonists VII. Synthesis of 6-Alkylpyrazolo-[3, 4-d] pyrimidines1, 2a
NO134212B (de)	1976-05-24
NO151287B (no)	1984-12-03	Analogifremgangsmaate for fremstilling av terapeutisk aktive 9-hydrazono-6,7,8,9-tetrahydro-4h-pyrido(1,2-a)-pyrimidinderivater
Ferrarini et al.	1990	One step synthesis of pyrimido [1, 2‐a][1, 8] naphthyridinones, pyrido [1, 2‐a] pyrimidinones and 1, 8‐naphthyridinones. Antihypertensive agents. V
SU969165A3 (ru)	1982-10-23	Способ получени конденсированных пиримидинов или их солей,или их оптических изомеров
Angier et al.	1948	Synthesis of pteroylglutamic acid. III
JPH0585553B2 (de)	1993-12-07
Suzuki et al.	1980	Synthesis of antimicrobial agents. IV. Synthesis and antimicrobial activities of imidazo [4, 5-b][1, 8] naphthyridine derivatives
Kurihara et al.	1981	Reaction of ethyl 3‐ethoxymethylene‐2, 4‐dioxovalerate and ethyl ethoxymethyleneoxaloacetate with 3‐aminopyrazole analogs. Synthesis and chemistry of 3, 6, 7‐trisubstituted pyrazolo [1, 5‐a] pyrimidine derivatives
SU589917A3 (ru)	1978-01-25	Способ получени производных пиримидина
HU181778B (en)	1983-11-28	Process for manufacturing substituted pyrido/1,2-a/ pyrimidines
Debeljak-Sustar et al.	1978	Heterocycles. 168. Neighboring group interaction in ortho-substituted aminopyridines. Pyridopyrimidines and related systems
Podanyi et al.	1986	Nitrogen bridgehead compounds. Part 63. Ring-chain tautomerism of [(alpha-N-hetaryl) aminomethylene] malononitriles
Ratajczyk et al.	1975	The cyclocondensation of 5‐amino‐1, 3‐dimethylpyrazole with ethyl acetoacetate. Synthesis of isomeric pyrazolopyridones
SU931108A3 (ru)	1982-05-23	Способ получени гексагидробензопирано/3,2-с/ пиридинов
JPS6045199B2 (ja)	1985-10-08	新規なイミダゾベンゾオキサジン及びそれらを含む製薬組成物
US3539568A (en)	1970-11-10	Process for preparing dicarboximide derivatives
MIYASHITA et al.	1991	Ring Transformation of Condensed Pyrimidines by Enamines and Ynamines. Formation of Condensed Pyridines and Condensed Diazocines
Gueiffier et al.	1990	Heterocyclic compounds with a bridgehead nitrogen atom. Synthesis in the imidazo [1, 2‐c] quinazoline series
Horváth et al.	1983	Nitrogen bridgehead compounds. Part 30. Vilsmeier–Haack formylation of 6, 7, 8, 9-tetrahydro-4 H-pyrido [1, 2-a] pyrimidin-4-ones
Ahmed	2002	A Convenient Synthesis for Some New Pyrido [4′, 3′: 4, 5] thieno [2, 3-d] pyrimidines and Related Fused 1, 2, 4-Triazolo and 1, 3, 4-Thiadiazolo-derivatives
Santilli et al.	1977	Synthesis of thiopyrano [2, 3‐d] pyrimidines and thieno [2, 3‐d] pyrimidines
HU180701B (en)	1983-04-29	Process for preparing pyrido-/1,2-a/pyrimidines containing a carboxylic or ester group on the pirimidimering