CH642368A5 - Pyrido(1,2-a)pyrimidine und verfahren zu ihrer herstellung. - Google Patents

Pyrido(1,2-a)pyrimidine und verfahren zu ihrer herstellung. Download PDF

Info

Publication number: CH642368A5
Authority: CH; Switzerland
Prior art keywords: group; oxo; pyrido; pyrimidine; acid
Prior art date: 1977-12-29

Application number

CH1323178A

Other languages

German (de)

English (en)

Inventor

Istvan Hermecz

Zoltan Meszaros

Lelle Vasvari-Debreczy

Agnes Horvath

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

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

1978-12-28

Publication date

1984-04-13

1978-12-28 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1984-04-13 Publication of CH642368A5 publication Critical patent/CH642368A5/de

Links

238000000034 method Methods 0.000 title claims description 25
VFMCUTPRJLZEEW-UHFFFAOYSA-N 4h-pyrido[1,2-a]pyrimidine Chemical compound C1=CC=CN2CC=CN=C21 VFMCUTPRJLZEEW-UHFFFAOYSA-N 0.000 title description 4
-1 2-Methyl-4-oxo-4H-pyrido [1,2-a] pyrimidine-6-carboxylic acid Chemical compound 0.000 claims description 50
150000001875 compounds Chemical class 0.000 claims description 45
125000004432 carbon atom Chemical group C* 0.000 claims description 38
239000000203 mixture Substances 0.000 claims description 30
229910052739 hydrogen Inorganic materials 0.000 claims description 29
239000001257 hydrogen Substances 0.000 claims description 29
239000007858 starting material Substances 0.000 claims description 27
125000000217 alkyl group Chemical group 0.000 claims description 23
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
125000004494 ethyl ester group Chemical group 0.000 claims description 16
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
239000003054 catalyst Substances 0.000 claims description 13
229910052757 nitrogen Inorganic materials 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 9
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 8
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 7
230000002378 acidificating effect Effects 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
229910052763 palladium Inorganic materials 0.000 claims description 7
239000003208 petroleum Substances 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
229920000137 polyphosphoric acid Polymers 0.000 claims description 7
125000002252 acyl group Chemical group 0.000 claims description 5
125000002843 carboxylic acid group Chemical group 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 5
239000012442 inert solvent Substances 0.000 claims description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 5
238000006798 ring closing metathesis reaction Methods 0.000 claims description 5
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
238000007363 ring formation reaction Methods 0.000 claims description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
HXUIDZOMTRMIOE-UHFFFAOYSA-N 3-oxo-3-phenylpropionic acid Chemical compound OC(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-N 0.000 claims description 3
XXDZVNZFPKPWHT-UHFFFAOYSA-N O=C1C(=CN=C2N1C=C(C=C2)C(=O)O)C(=O)O Chemical compound O=C1C(=CN=C2N1C=C(C=C2)C(=O)O)C(=O)O XXDZVNZFPKPWHT-UHFFFAOYSA-N 0.000 claims description 3
239000005662 Paraffin oil Substances 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 claims description 3
239000000969 carrier Substances 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 3
125000002560 nitrile group Chemical group 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
239000007787 solid Substances 0.000 claims description 3
AVAQZFUVMGMHSC-SNAWJCMRSA-N (e)-2-cyano-3-ethoxyprop-2-enoic acid Chemical compound CCO\C=C(/C#N)C(O)=O AVAQZFUVMGMHSC-SNAWJCMRSA-N 0.000 claims description 2
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 claims description 2
QNLSLYKWBHYEHK-UHFFFAOYSA-N 2-(2-formylphenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1C=O QNLSLYKWBHYEHK-UHFFFAOYSA-N 0.000 claims description 2
YHXUUIXBGUFOKL-UHFFFAOYSA-N 2-formylbutanedioic acid Chemical compound OC(=O)CC(C=O)C(O)=O YHXUUIXBGUFOKL-UHFFFAOYSA-N 0.000 claims description 2
VOKUMXABRRXHAR-UHFFFAOYSA-N 2-methyl-3-oxopropanoic acid Chemical compound O=CC(C)C(O)=O VOKUMXABRRXHAR-UHFFFAOYSA-N 0.000 claims description 2
WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 2
239000007868 Raney catalyst Substances 0.000 claims description 2
229910000564 Raney nickel Inorganic materials 0.000 claims description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
230000015572 biosynthetic process Effects 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 claims description 2
JYJDSHOINDVLQU-UHFFFAOYSA-N ethyl 3-acetyl-4-oxopyrido[1,2-a]pyrimidine-6-carboxylate Chemical compound C1=C(C(C)=O)C(=O)N2C(C(=O)OCC)=CC=CC2=N1 JYJDSHOINDVLQU-UHFFFAOYSA-N 0.000 claims description 2
125000004997 halocarbonyl group Chemical group 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
238000005984 hydrogenation reaction Methods 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 2
229910052703 rhodium Inorganic materials 0.000 claims description 2
239000010948 rhodium Substances 0.000 claims description 2
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
239000007859 condensation product Substances 0.000 claims 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
150000003930 2-aminopyridines Chemical class 0.000 claims 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 claims 1
QMZBAEMEEKBAOC-UHFFFAOYSA-N 3-methyl-4-oxopyrido[1,2-a]pyrimidine-7-carboxylic acid Chemical compound CC1=CN=C2N(C1=O)C=C(C=C2)C(=O)O QMZBAEMEEKBAOC-UHFFFAOYSA-N 0.000 claims 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 claims 1
125000005907 alkyl ester group Chemical group 0.000 claims 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
230000003197 catalytic effect Effects 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 claims 1
229910052697 platinum Inorganic materials 0.000 claims 1
150000003222 pyridines Chemical class 0.000 claims 1
150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 70
239000000155 melt Substances 0.000 description 33
230000008018 melting Effects 0.000 description 14
238000002844 melting Methods 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 11
238000001953 recrystallisation Methods 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
238000009835 boiling Methods 0.000 description 7
239000013078 crystal Substances 0.000 description 7
239000000243 solution Substances 0.000 description 7
150000002148 esters Chemical class 0.000 description 6
239000000047 product Substances 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
235000010357 aspartame Nutrition 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
239000003921 oil Substances 0.000 description 4
TUCIOBMMDDOEMM-RIYZIHGNSA-N tyrphostin B42 Chemical compound C1=C(O)C(O)=CC=C1\C=C(/C#N)C(=O)NCC1=CC=CC=C1 TUCIOBMMDDOEMM-RIYZIHGNSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
235000011054 acetic acid Nutrition 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 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
238000001816 cooling Methods 0.000 description 3
FIKVWPJKNMTBBD-UHFFFAOYSA-N ethyl 6-aminopyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC=C(N)N=C1 FIKVWPJKNMTBBD-UHFFFAOYSA-N 0.000 description 3
230000002349 favourable effect Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
GVOCVCMKQNNYPG-UHFFFAOYSA-N CCOC(=O)C(C)=CNC1=CC(C(=O)OCC)=CC=N1 Chemical compound CCOC(=O)C(C)=CNC1=CC(C(=O)OCC)=CC=N1 GVOCVCMKQNNYPG-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
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-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
239000002168 alkylating agent Substances 0.000 description 2
229940100198 alkylating agent Drugs 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 2
230000003266 anti-allergic effect Effects 0.000 description 2
230000001088 anti-asthma Effects 0.000 description 2
239000000924 antiasthmatic agent Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
WLXALCKAKGDNAT-UHFFFAOYSA-N diazoethane Chemical compound CC=[N+]=[N-] WLXALCKAKGDNAT-UHFFFAOYSA-N 0.000 description 2
ZFRCVCAYDRJIJK-UHFFFAOYSA-N diethyl 2-[[(5-ethoxycarbonylpyridin-2-yl)amino]methylidene]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)=CNC1=CC=C(C(=O)OCC)C=N1 ZFRCVCAYDRJIJK-UHFFFAOYSA-N 0.000 description 2
KWUJMZRSAXCXPD-UHFFFAOYSA-N diethyl 4-oxopyrido[1,2-a]pyrimidine-3,6-dicarboxylate Chemical compound C1=C(C(=O)OCC)C(=O)N2C(C(=O)OCC)=CC=CC2=N1 KWUJMZRSAXCXPD-UHFFFAOYSA-N 0.000 description 2
LELKDPCCSLMHPV-UHFFFAOYSA-N diethyl 4-oxopyrido[1,2-a]pyrimidine-3,8-dicarboxylate Chemical compound C1=C(C(=O)OCC)C=CN2C1=NC=C(C(=O)OCC)C2=O LELKDPCCSLMHPV-UHFFFAOYSA-N 0.000 description 2
NWSJRMUWUWCSOY-UHFFFAOYSA-N diethyl 4-oxopyrido[1,2-a]pyrimidine-3,9-dicarboxylate Chemical compound CCOC(=O)C1=CC=CN2C1=NC=C(C(=O)OCC)C2=O NWSJRMUWUWCSOY-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
DTYDENRYZSEGNL-UHFFFAOYSA-N ethyl 6-aminopyridine-2-carboxylate Chemical compound CCOC(=O)C1=CC=CC(N)=N1 DTYDENRYZSEGNL-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
150000007517 lewis acids Chemical class 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
229910052987 metal hydride Inorganic materials 0.000 description 2
150000004681 metal hydrides Chemical class 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
JLIDRDJNLAWIKT-UHFFFAOYSA-N 1,2-dimethyl-3h-benzo[e]indole Chemical compound C1=CC=CC2=C(C(=C(C)N3)C)C3=CC=C21 JLIDRDJNLAWIKT-UHFFFAOYSA-N 0.000 description 1
FHARGMSSJPHLMO-UHFFFAOYSA-N 2-(2h-pyrimidin-1-yl)acetic acid Chemical compound OC(=O)CN1CN=CC=C1 FHARGMSSJPHLMO-UHFFFAOYSA-N 0.000 description 1
YIFCWYUSYGFFMH-UHFFFAOYSA-N 2-(ethoxymethylidene)propanedioic acid Chemical compound CCOC=C(C(O)=O)C(O)=O YIFCWYUSYGFFMH-UHFFFAOYSA-N 0.000 description 1
VISYPTDDWLOSGX-UHFFFAOYSA-N 2-benzoyl-3-ethoxyprop-2-enoic acid Chemical compound CCOC=C(C(O)=O)C(=O)C1=CC=CC=C1 VISYPTDDWLOSGX-UHFFFAOYSA-N 0.000 description 1
DERAACKMMNJAFU-UHFFFAOYSA-N 2-ethoxy-1,3-dioxane-4,6-dione Chemical compound CCOC1OC(=O)CC(=O)O1 DERAACKMMNJAFU-UHFFFAOYSA-N 0.000 description 1
NMUKFRCHLYPKSR-UHFFFAOYSA-N 2-formylglutaric acid Chemical compound OC(=O)CCC(C=O)C(O)=O NMUKFRCHLYPKSR-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
CVQGFKKCKVAEIK-UHFFFAOYSA-N 3-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC=CN2C(=O)C(C)=CN=C21 CVQGFKKCKVAEIK-UHFFFAOYSA-N 0.000 description 1
FHSUFDYFOHSYHI-UHFFFAOYSA-N 3-oxopentanoic acid Chemical compound CCC(=O)CC(O)=O FHSUFDYFOHSYHI-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
VJLHZZYJMCIFCR-UHFFFAOYSA-N 4-oxopyrido[1,2-a]pyrimidine-3,8-dicarboxylic acid Chemical compound O=C1C(=CN=C2N1C=CC(=C2)C(=O)O)C(=O)O VJLHZZYJMCIFCR-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
AXRPRDQOIUBSPO-UHFFFAOYSA-N C(C)OC(=O)C1CCCN2C1=NC=C(C2=O)C2=CC=CC=C2 Chemical compound C(C)OC(=O)C1CCCN2C1=NC=C(C2=O)C2=CC=CC=C2 AXRPRDQOIUBSPO-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
MHQCMLIOUODJCH-UHFFFAOYSA-N C(C)OC(CC1=CN=C2N(C1=O)C=CC=C2C(=O)OCC)=O Chemical compound C(C)OC(CC1=CN=C2N(C1=O)C=CC=C2C(=O)OCC)=O MHQCMLIOUODJCH-UHFFFAOYSA-N 0.000 description 1
KLOBBQHCJOWABB-UHFFFAOYSA-N C(C)OC(CC1C(C=CC=C1)=CNC1=NC(=CC=C1)C(=O)OCC)=O Chemical compound C(C)OC(CC1C(C=CC=C1)=CNC1=NC(=CC=C1)C(=O)OCC)=O KLOBBQHCJOWABB-UHFFFAOYSA-N 0.000 description 1
JQEAECYYXQXVES-UHFFFAOYSA-N C1(CC(=O)OC(NC2=NC=CC(=C2)C(=O)OCC)O1)=O Chemical compound C1(CC(=O)OC(NC2=NC=CC(=C2)C(=O)OCC)O1)=O JQEAECYYXQXVES-UHFFFAOYSA-N 0.000 description 1
CENLHUJPEBEWOT-UHFFFAOYSA-N CCOC(=O)C(C#N)=CNC1=CC=C(C(=O)OCC)C=N1 Chemical compound CCOC(=O)C(C#N)=CNC1=CC=C(C(=O)OCC)C=N1 CENLHUJPEBEWOT-UHFFFAOYSA-N 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
FGMNCHKQOYUADO-UHFFFAOYSA-N Cl.CC=1N=C2N(C(C1)=O)C(=CC=C2)C(=O)OCC Chemical compound Cl.CC=1N=C2N(C(C1)=O)C(=CC=C2)C(=O)OCC FGMNCHKQOYUADO-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
IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
LTYZMAHZKJQIMN-UHFFFAOYSA-N O=C1C(=CN=C2N1CCC(C2)C(=O)O)C(=O)O Chemical compound O=C1C(=CN=C2N1CCC(C2)C(=O)O)C(=O)O LTYZMAHZKJQIMN-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical group 0.000 description 1
150000001351 alkyl iodides Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000000489 anti-atherogenic effect Effects 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000000843 anti-fungal effect Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000000702 anti-platelet effect Effects 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
239000003146 anticoagulant agent Substances 0.000 description 1
229940121375 antifungal agent Drugs 0.000 description 1
239000002221 antipyretic Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
DULCUDSUACXJJC-UHFFFAOYSA-N benzeneacetic acid ethyl ester Natural products CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
230000004071 biological effect Effects 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
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
150000008050 dialkyl sulfates Chemical class 0.000 description 1
LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
LGMXTAWFVDGRBE-UHFFFAOYSA-N diethyl 2-[[(4-ethoxycarbonylpyridin-2-yl)amino]methylidene]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)=CNC1=CC(C(=O)OCC)=CC=N1 LGMXTAWFVDGRBE-UHFFFAOYSA-N 0.000 description 1
GMABSOBRIBTCNG-UHFFFAOYSA-N diethyl 2-[[(6-ethoxycarbonylpyridin-2-yl)amino]methylidene]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)=CNC1=CC=CC(C(=O)OCC)=N1 GMABSOBRIBTCNG-UHFFFAOYSA-N 0.000 description 1
KBFCODNYMKOLOB-UHFFFAOYSA-N diethyl 4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3,6-dicarboxylate Chemical compound C(C)OC(=O)C1=CN=C2N(C1=O)C(CCC2)C(=O)OCC KBFCODNYMKOLOB-UHFFFAOYSA-N 0.000 description 1
YIJHLNMUCLWCIP-UHFFFAOYSA-N diethyl 4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3,7-dicarboxylate Chemical compound O=C1C(=CN=C2N1CC(CC2)C(=O)OCC)C(=O)OCC YIJHLNMUCLWCIP-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
XWIUIRQSQROZGJ-UHFFFAOYSA-N ethyl 2-(2-formylphenyl)acetate Chemical compound CCOC(=O)CC1=CC=CC=C1C=O XWIUIRQSQROZGJ-UHFFFAOYSA-N 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
SDNBAOYWLYELRV-UHFFFAOYSA-N ethyl 2-methyl-4-oxopyrido[1,2-a]pyrimidine-6-carboxylate Chemical compound CC=1N=C2N(C(C1)=O)C(=CC=C2)C(=O)OCC SDNBAOYWLYELRV-UHFFFAOYSA-N 0.000 description 1
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 1
KKCJQYJWNJXNFH-UHFFFAOYSA-N ethyl 3-methyl-4-oxopyrido[1,2-a]pyrimidine-9-carboxylate Chemical compound CCOC(=O)C1=CC=CN2C1=NC=C(C)C2=O KKCJQYJWNJXNFH-UHFFFAOYSA-N 0.000 description 1
FIOMIGBEEKXMBN-UHFFFAOYSA-N ethyl 4-oxo-3-phenylpyrido[1,2-a]pyrimidine-6-carboxylate Chemical compound O=C1N2C(C(=O)OCC)=CC=CC2=NC=C1C1=CC=CC=C1 FIOMIGBEEKXMBN-UHFFFAOYSA-N 0.000 description 1
JPASKMJDUYKORW-UHFFFAOYSA-N ethyl 6-[[6-(2-ethoxy-2-oxoethyl)cyclohexa-2,4-dien-1-ylidene]methylamino]pyridine-3-carboxylate Chemical compound C(C)OC(=O)C=1C=CC(=NC1)NC=C1C(C=CC=C1)CC(=O)OCC JPASKMJDUYKORW-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
235000019253 formic acid Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
125000005528 methosulfate group Chemical group 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
230000001151 other effect Effects 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
239000002904 solvent Substances 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 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

Landscapes

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)
Pain & Pain Management (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Vascular Medicine (AREA)
Pulmonology (AREA)
Cardiology (AREA)
Hematology (AREA)
Diabetes (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Immunology (AREA)
Anesthesiology (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyridine Compounds (AREA)

CH1323178A 1977-12-29 1978-12-28 Pyrido(1,2-a)pyrimidine und verfahren zu ihrer herstellung. CH642368A5 (de)

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
CH642368A5 true CH642368A5 (de)	1984-04-13

Family

ID=10994685

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1323178A CH642368A5 (de)	1977-12-29	1978-12-28	Pyrido(1,2-a)pyrimidine und verfahren zu ihrer herstellung.

Country Status (8)

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

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 (ja) *	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 JP JP16453378A patent/JPS5498797A/ja active Pending
- 1978-12-27 FR FR7836463A patent/FR2413375A1/fr active Granted
- 1978-12-28 GB GB7850108A patent/GB2011410B/en not_active Expired
- 1978-12-28 CH CH1323178A patent/CH642368A5/de not_active IP Right Cessation
- 1978-12-29 BE BE192660A patent/BE873195A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPS5498797A (en)	1979-08-03
GB2011410A (en)	1979-07-11
GB2011410B (en)	1982-09-22
FR2413375A1 (fr)	1979-07-27
FR2413375B1 (ja)	1983-08-05
DE2853273A1 (de)	1979-07-12
BE873195A (fr)	1979-04-17
SU1022659A3 (ru)	1983-06-07
HU180701B (en)	1983-04-29

Legal Events

Date	Code	Title	Description
1987-08-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE1795769C3 (de)	1978-11-02	6,7,8,9-Tetrahydro-2H-pyrido [Ua] pyrimidinderivate, deren Salze mit Säuren und quaternäre Methosalze, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel
DE2614406A1 (de)	1976-10-14	Tetracyclische verbindungen, verfahren zu deren herstellung und arzneimittel, enthaltend diese verbindungen
DE2858259C2 (de)	1990-06-13	9,10-Dimathoxy-2,3,6,7-tetrahydro-4-H-pyrimido-(6,1-a)-isochinolin-4-on-Derivate und Verfahren zu ihrer Herstellung
DE2835004A1 (de)	1979-03-01	Pyrido eckige klammer auf 1,2-a eckige klammer zu pyrimidinderivate, verfahren zu deren herstellung und pharmazeutische praeparate
EP0386628B1 (de)	1993-06-23	Verfahren zur Herstellung von Indolcarbonsäurederivaten
CH621552A5 (ja)	1981-02-13
CH628894A5 (de)	1982-03-31	Verfahren zum herstellen von neuen benzo(a) chinolizidin-derivaten.
CH617694A5 (ja)	1980-06-13
CH642368A5 (de)	1984-04-13	Pyrido(1,2-a)pyrimidine und verfahren zu ihrer herstellung.
DE2624352C3 (de)	1979-06-28	Dibenzo [bfl thiepine, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende entzündungshemmende Zubereitungen
DE2836449C2 (ja)	1990-09-06
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