SE437158B - Substituerade pyrido/1,2-a/pyrimidiner, forfarande for framstellning derav och farmaceutisk komposition - Google Patents
Substituerade pyrido/1,2-a/pyrimidiner, forfarande for framstellning derav och farmaceutisk kompositionInfo
- Publication number
- SE437158B SE437158B SE8003433A SE8003433A SE437158B SE 437158 B SE437158 B SE 437158B SE 8003433 A SE8003433 A SE 8003433A SE 8003433 A SE8003433 A SE 8003433A SE 437158 B SE437158 B SE 437158B
- Authority
- SE
- Sweden
- Prior art keywords
- trans
- oxo
- ethenyl
- carboxylic acid
- pyrimidine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 150000003230 pyrimidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 118
- 239000000203 mixture Substances 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 230000003266 anti-allergic effect Effects 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- PNWRNPXJVJQYSL-BQYQJAHWSA-N 6-ethyl-5-[(e)-2-(3-methoxyphenyl)ethenyl]-7-oxo-1,8a-dihydrocyclopropa[1,2]pyrido[3,6-c]pyrimidine-1a-carboxylic acid Chemical compound N1=C2C=CC3(C(O)=O)CC3N2C(=O)C(CC)=C1\C=C\C1=CC=CC(OC)=C1 PNWRNPXJVJQYSL-BQYQJAHWSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 238000005888 cyclopropanation reaction Methods 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- WGHBWPBRGRQGFJ-VQHVLOKHSA-N 3-ethyl-2-[(e)-2-(3-methoxyphenyl)ethenyl]-4-oxopyrido[1,2-a]pyrimidine-7-carboxylic acid Chemical compound N1=C2C=CC(C(O)=O)=CN2C(=O)C(CC)=C1\C=C\C1=CC=CC(OC)=C1 WGHBWPBRGRQGFJ-VQHVLOKHSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- FTDNJRKTOUVQTL-ZRDIBKRKSA-N 2-[(e)-2-(3-ethoxy-2-methoxyphenyl)ethenyl]-4-oxo-3-propylpyrido[1,2-a]pyrimidine-7-carboxylic acid Chemical compound N1=C2C=CC(C(O)=O)=CN2C(=O)C(CCC)=C1\C=C\C1=CC=CC(OCC)=C1OC FTDNJRKTOUVQTL-ZRDIBKRKSA-N 0.000 claims description 3
- MWHNTGGIOOKBRO-ZRDIBKRKSA-N 3-butyl-4-oxo-2-[(e)-2-phenylethenyl]pyrido[1,2-a]pyrimidine-7-carboxylic acid Chemical compound N1=C2C=CC(C(O)=O)=CN2C(=O)C(CCCC)=C1\C=C\C1=CC=CC=C1 MWHNTGGIOOKBRO-ZRDIBKRKSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 3
- OCDHKWKQEWDBAZ-CMDGGOBGSA-N 5-[(e)-2-(3-ethoxyphenyl)ethenyl]-6-ethyl-7-oxo-1,8a-dihydrocyclopropa[1,2]pyrido[3,6-c]pyrimidine-1a-carboxylic acid Chemical compound CCOC1=CC=CC(\C=C\C2=C(C(=O)N3C4CC4(C=CC3=N2)C(O)=O)CC)=C1 OCDHKWKQEWDBAZ-CMDGGOBGSA-N 0.000 claims description 2
- 230000000767 anti-ulcer Effects 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 230000003178 anti-diabetic effect Effects 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- -1 6,7-methylene compounds Chemical class 0.000 description 107
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 49
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 239000002253 acid Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000002244 precipitate Substances 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 150000004702 methyl esters Chemical class 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 229920002554 vinyl polymer Polymers 0.000 description 14
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 13
- 239000005457 ice water Substances 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 150000002576 ketones Chemical class 0.000 description 10
- 238000011282 treatment Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 125000004494 ethyl ester group Chemical group 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 description 7
- KGBJXKLZZUNXQI-VQHVLOKHSA-N 3-methyl-4-oxo-2-[(e)-2-phenylethenyl]pyrido[1,2-a]pyrimidine-7-carboxylic acid Chemical compound N1=C2C=CC(C(O)=O)=CN2C(=O)C(C)=C1\C=C\C1=CC=CC=C1 KGBJXKLZZUNXQI-VQHVLOKHSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 6
- 238000007363 ring formation reaction Methods 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- ZVNGGZZUMWVPKQ-CSKARUKUSA-N 2-[(e)-2-(2,3-dimethoxyphenyl)ethenyl]-3-ethyl-4-oxopyrido[1,2-a]pyrimidine-7-carboxylic acid Chemical compound N1=C2C=CC(C(O)=O)=CN2C(=O)C(CC)=C1\C=C\C1=CC=CC(OC)=C1OC ZVNGGZZUMWVPKQ-CSKARUKUSA-N 0.000 description 5
- NNJFRARRNSPGFB-PKNBQFBNSA-N 2-[(e)-2-(2-methylphenyl)ethenyl]-4-oxo-3-propylpyrido[1,2-a]pyrimidine-7-carboxylic acid Chemical compound N1=C2C=CC(C(O)=O)=CN2C(=O)C(CCC)=C1\C=C\C1=CC=CC=C1C NNJFRARRNSPGFB-PKNBQFBNSA-N 0.000 description 5
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 5
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 5
- MHGMBZMMKSZOGS-CMDGGOBGSA-N 6-ethyl-5-[(e)-2-(2-methylphenyl)ethenyl]-7-oxo-1,8a-dihydrocyclopropa[1,2]pyrido[3,6-c]pyrimidine-1a-carboxylic acid Chemical compound N1=C2C=CC3(C(O)=O)CC3N2C(=O)C(CC)=C1\C=C\C1=CC=CC=C1C MHGMBZMMKSZOGS-CMDGGOBGSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 description 5
- IXXDBGSSNAQIJA-UHFFFAOYSA-N 4-oxopyrido[1,2-a]pyrimidine-7-carboxylic acid Chemical compound C1=CC(=O)N2C=C(C(=O)O)C=CC2=N1 IXXDBGSSNAQIJA-UHFFFAOYSA-N 0.000 description 4
- ZOZBRCKHXFEHNY-MDZDMXLPSA-N 5-[(e)-2-(2,3-dimethoxyphenyl)ethenyl]-7-oxo-6-propyl-1,8a-dihydrocyclopropa[1,2]pyrido[3,6-c]pyrimidine-1a-carboxylic acid Chemical compound N1=C2C=CC3(C(O)=O)CC3N2C(=O)C(CCC)=C1\C=C\C1=CC=CC(OC)=C1OC ZOZBRCKHXFEHNY-MDZDMXLPSA-N 0.000 description 4
- VZHYHFJIYRNWJU-MDZDMXLPSA-N 5-[(e)-2-(2-methylphenyl)ethenyl]-7-oxo-6-propyl-1,8a-dihydrocyclopropa[1,2]pyrido[3,6-c]pyrimidine-1a-carboxylic acid Chemical compound N1=C2C=CC3(C(O)=O)CC3N2C(=O)C(CCC)=C1\C=C\C1=CC=CC=C1C VZHYHFJIYRNWJU-MDZDMXLPSA-N 0.000 description 4
- WZZJIHMWWUMTTN-CMDGGOBGSA-N 6-ethyl-7-oxo-5-[(e)-2-phenylethenyl]-1,8a-dihydrocyclopropa[1,2]pyrido[3,6-c]pyrimidine-1a-carboxylic acid Chemical compound N1=C2C=CC3(C(O)=O)CC3N2C(=O)C(CC)=C1\C=C\C1=CC=CC=C1 WZZJIHMWWUMTTN-CMDGGOBGSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
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- 239000008101 lactose Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 3
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 3
- YVXHRAYXYLVPEG-PKNBQFBNSA-N 4-oxo-2-[(e)-2-phenylethenyl]-3-propylpyrido[1,2-a]pyrimidine-7-carboxylic acid Chemical compound N1=C2C=CC(C(O)=O)=CN2C(=O)C(CCC)=C1\C=C\C1=CC=CC=C1 YVXHRAYXYLVPEG-PKNBQFBNSA-N 0.000 description 3
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- 239000005977 Ethylene Substances 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
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- 229940067606 lecithin Drugs 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
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- 235000019698 starch Nutrition 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
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- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- JUWAVQMZQGPJCK-PKNBQFBNSA-N 2-[(e)-2-(2,3-dimethoxyphenyl)ethenyl]-4-oxo-3-propylpyrido[1,2-a]pyrimidine-7-carboxylic acid Chemical compound N1=C2C=CC(C(O)=O)=CN2C(=O)C(CCC)=C1\C=C\C1=CC=CC(OC)=C1OC JUWAVQMZQGPJCK-PKNBQFBNSA-N 0.000 description 2
- WIAKUXSZKOKEBR-CSKARUKUSA-N 2-[(e)-2-(3-methoxyphenyl)ethenyl]-4-oxo-3-propylpyrido[1,2-a]pyrimidine-7-carboxylic acid Chemical compound N1=C2C=CC(C(O)=O)=CN2C(=O)C(CCC)=C1\C=C\C1=CC=CC(OC)=C1 WIAKUXSZKOKEBR-CSKARUKUSA-N 0.000 description 2
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 2
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- GYELGGWGTBIBIX-SOFGYWHQSA-N 4-oxo-2-[(e)-2-phenylethenyl]pyrido[1,2-a]pyrimidine-7-carboxylic acid Chemical compound C=1C(=O)N2C=C(C(=O)O)C=CC2=NC=1\C=C\C1=CC=CC=C1 GYELGGWGTBIBIX-SOFGYWHQSA-N 0.000 description 2
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- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- LPWFRMWAZWNDMK-ZRDIBKRKSA-N methyl 2-[(e)-2-(2-methylphenyl)ethenyl]-4-oxo-3-propylpyrido[1,2-a]pyrimidine-7-carboxylate Chemical compound N1=C2C=CC(C(=O)OC)=CN2C(=O)C(CCC)=C1\C=C\C1=CC=CC=C1C LPWFRMWAZWNDMK-ZRDIBKRKSA-N 0.000 description 1
- JACPDLJUQLKABC-UHFFFAOYSA-N methyl 6-aminopyridine-3-carboxylate Chemical compound COC(=O)C1=CC=C(N)N=C1 JACPDLJUQLKABC-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- YPLIFKZBNCNJJN-UHFFFAOYSA-N n,n-bis(ethylamino)ethanamine Chemical compound CCNN(CC)NCC YPLIFKZBNCNJJN-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 231100000048 toxicity data Toxicity 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7915810 | 1979-05-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8003433L SE8003433L (sv) | 1980-11-09 |
| SE437158B true SE437158B (sv) | 1985-02-11 |
Family
ID=10504995
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8003433A SE437158B (sv) | 1979-05-08 | 1980-05-07 | Substituerade pyrido/1,2-a/pyrimidiner, forfarande for framstellning derav och farmaceutisk komposition |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US4310526A (cs) |
| JP (1) | JPS562983A (cs) |
| AT (1) | AT375370B (cs) |
| AU (1) | AU527931B2 (cs) |
| BE (1) | BE883150A (cs) |
| CA (1) | CA1134359A (cs) |
| CH (1) | CH647777A5 (cs) |
| CS (2) | CS528780A2 (cs) |
| DE (1) | DE3015738A1 (cs) |
| DK (1) | DK200280A (cs) |
| ES (1) | ES8104287A1 (cs) |
| FI (1) | FI68824C (cs) |
| FR (1) | FR2456093A1 (cs) |
| GB (1) | GB2050353B (cs) |
| GR (1) | GR68075B (cs) |
| HU (1) | HU181778B (cs) |
| IE (1) | IE49787B1 (cs) |
| IL (1) | IL59802A (cs) |
| IT (1) | IT1209326B (cs) |
| LU (1) | LU82419A1 (cs) |
| NL (1) | NL8002656A (cs) |
| NO (1) | NO153137C (cs) |
| NZ (1) | NZ193579A (cs) |
| PH (1) | PH16695A (cs) |
| PT (1) | PT71197A (cs) |
| SE (1) | SE437158B (cs) |
| SU (2) | SU1217259A3 (cs) |
| ZA (1) | ZA802390B (cs) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT377586B (de) | 1981-06-30 | 1985-04-10 | Erba Farmitalia | Verfahren zur herstellung von substituierten pyrrolo-(2,1-b)-chinazolinen und pyrido(2,1-b)chinazolinen |
| US4537962A (en) * | 1982-02-04 | 1985-08-27 | Farmitalia Carlo Erba, S.P.A. | Substituted 1,3,4-thiadiazolo[3,2-A]pyrimidines and compositions containing them |
| CA1211111A (en) * | 1982-02-15 | 1986-09-09 | Isao Yanagisawa | Process for preparing novel pyrimidone compounds |
| ES521739A0 (es) * | 1982-04-29 | 1984-07-01 | Erba Farmitalia | Procedimiento para preparar derivados cicloalifaticos condensados de pirido(1,2-a)pirimidinas sustituidas. |
| IL69274A (en) * | 1982-08-05 | 1986-08-31 | Erba Farmitalia | (substituted amino)derivatives of 3-benzylidene-pyrrolo(2,1-b)quinazolin-9-ones and 6-benzylidene-pyrido(2,1-b)quinazolin-11-ones,their preparation and pharmaceutical compositions containing them |
| GB8300728D0 (en) * | 1983-01-12 | 1983-02-16 | Erba Farmitalia | Substituted carboxy-thiazolo / 3 2 - a / pyrimidine derivatives |
| US4457932A (en) * | 1983-07-22 | 1984-07-03 | Bristol-Myers Company | Anti-ulcer agents |
| GB8501015D0 (en) * | 1985-01-16 | 1985-02-20 | Riker Laboratories Inc | Drug |
| JP2668259B2 (ja) * | 1988-02-18 | 1997-10-27 | 塩野義製薬株式会社 | 複素環化合物および抗潰瘍剤 |
| CA2724008A1 (en) * | 2008-01-11 | 2009-09-11 | Prasada Rao V.S. Lingam | Fused pyrimidine derivatives as trpv3 modulators |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4209622A (en) * | 1973-03-30 | 1980-06-24 | Chinoin Gygyszer es Vegyeszeti Termekek Gyara Rt. | 3-(Ethoxycarbonyl-methyl)-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine |
| US3935197A (en) * | 1975-05-16 | 1976-01-27 | E. R. Squibb & Sons, Inc. | 2-Styryl-4H-pyrido(1,2-a)pyrimidin-4-ones |
| 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 |
| HU184058B (en) | 1977-12-29 | 1984-06-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing new compounds with nitrogen bridge head |
| HU180701B (en) | 1977-12-29 | 1983-04-29 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing pyrido-/1,2-a/pyrimidines containing a carboxylic or ester group on the pirimidimering |
-
1980
- 1980-04-10 IL IL59802A patent/IL59802A/xx unknown
- 1980-04-10 US US06/138,879 patent/US4310526A/en not_active Expired - Lifetime
- 1980-04-10 AU AU57319/80A patent/AU527931B2/en not_active Ceased
- 1980-04-17 GB GB8012638A patent/GB2050353B/en not_active Expired
- 1980-04-18 PH PH23918A patent/PH16695A/en unknown
- 1980-04-21 ZA ZA00802390A patent/ZA802390B/xx unknown
- 1980-04-23 GR GR61754A patent/GR68075B/el unknown
- 1980-04-24 DE DE19803015738 patent/DE3015738A1/de not_active Withdrawn
- 1980-04-30 NZ NZ193579A patent/NZ193579A/xx unknown
- 1980-05-05 LU LU82419A patent/LU82419A1/fr unknown
- 1980-05-06 IT IT8021821A patent/IT1209326B/it active
- 1980-05-06 FI FI801464A patent/FI68824C/fi not_active IP Right Cessation
- 1980-05-07 SE SE8003433A patent/SE437158B/sv not_active IP Right Cessation
- 1980-05-07 CH CH3571/80A patent/CH647777A5/de not_active IP Right Cessation
- 1980-05-07 ES ES491238A patent/ES8104287A1/es not_active Expired
- 1980-05-07 SU SU802917352A patent/SU1217259A3/ru active
- 1980-05-07 IE IE945/80A patent/IE49787B1/en unknown
- 1980-05-07 DK DK200280A patent/DK200280A/da not_active Application Discontinuation
- 1980-05-07 BE BE2/500A patent/BE883150A/fr not_active IP Right Cessation
- 1980-05-07 NO NO801342A patent/NO153137C/no unknown
- 1980-05-07 CS CS805287A patent/CS528780A2/cs unknown
- 1980-05-07 CA CA000351417A patent/CA1134359A/en not_active Expired
- 1980-05-07 PT PT71197A patent/PT71197A/pt unknown
- 1980-05-07 HU HU801121A patent/HU181778B/hu unknown
- 1980-05-07 CS CS803213A patent/CS244107B2/cs unknown
- 1980-05-08 AT AT0245680A patent/AT375370B/de not_active IP Right Cessation
- 1980-05-08 JP JP6001780A patent/JPS562983A/ja active Pending
- 1980-05-08 FR FR8010290A patent/FR2456093A1/fr active Granted
- 1980-05-08 NL NL8002656A patent/NL8002656A/nl not_active Application Discontinuation
-
1981
- 1981-05-27 US US06/267,450 patent/US4341780A/en not_active Expired - Fee Related
- 1981-06-24 SU SU813308438A patent/SU1158045A3/ru active
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