SE437030B - 3-substituerade tetrahydro-pyrrolo/1,2-a/pyrimidiner, forfarande for framstellning derav och farmaceutiska preparat innehallande dessa foreningar - Google Patents
3-substituerade tetrahydro-pyrrolo/1,2-a/pyrimidiner, forfarande for framstellning derav och farmaceutiska preparat innehallande dessa foreningarInfo
- Publication number
- SE437030B SE437030B SE8003477A SE8003477A SE437030B SE 437030 B SE437030 B SE 437030B SE 8003477 A SE8003477 A SE 8003477A SE 8003477 A SE8003477 A SE 8003477A SE 437030 B SE437030 B SE 437030B
- Authority
- SE
- Sweden
- Prior art keywords
- general formula
- pyrrolo
- lower alkyl
- oxo
- pyrimidine
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 39
- 238000000034 method Methods 0.000 title claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 4
- 150000003230 pyrimidines Chemical class 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- -1 diethylethoxy-methylene-methyl Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- AHFWKTKIRQCWCQ-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrol-5-amine Chemical class NC1=CCCN1 AHFWKTKIRQCWCQ-UHFFFAOYSA-N 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 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 8
- 150000002825 nitriles Chemical class 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 claims description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 230000003257 anti-anginal effect Effects 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- VVCYNVCCODBCOE-UHFFFAOYSA-N ethyl 2-methyl-3-oxopropanoate Chemical compound CCOC(=O)C(C)C=O VVCYNVCCODBCOE-UHFFFAOYSA-N 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- DULCUDSUACXJJC-UHFFFAOYSA-N Ethyl phenylacetate Chemical compound CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 claims 2
- RRQDQAFGOYUKOZ-UHFFFAOYSA-N 3h-pyrrolo[1,2-a]pyrimidin-4-one Chemical compound O=C1CC=NC2=CC=CN12 RRQDQAFGOYUKOZ-UHFFFAOYSA-N 0.000 claims 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims 1
- KTMGNAIGXYODKQ-UHFFFAOYSA-N ethyl 2-cyano-3-ethoxyprop-2-enoate Chemical compound CCOC=C(C#N)C(=O)OCC KTMGNAIGXYODKQ-UHFFFAOYSA-N 0.000 claims 1
- 238000001640 fractional crystallisation Methods 0.000 claims 1
- JBDKAABFESSFMV-UHFFFAOYSA-N pyrrolo[1,2-a]pyrimidine Chemical class N1=CC=CN2C=CC=C21 JBDKAABFESSFMV-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 34
- 238000002844 melting Methods 0.000 description 32
- 230000008018 melting Effects 0.000 description 32
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 239000013078 crystal Substances 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 229910052799 carbon Inorganic materials 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 239000007858 starting material Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- CSOYDALHEQEMAK-UHFFFAOYSA-N 2h-pyrimidine-1-carboxylic acid Chemical compound OC(=O)N1CN=CC=C1 CSOYDALHEQEMAK-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- XJZCMNZCVOSPLA-UHFFFAOYSA-N ethyl 2-oxo-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidine-3-carboxylate Chemical compound O=C1C(C(=O)OCC)=CN2CCCC2=N1 XJZCMNZCVOSPLA-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 150000003857 carboxamides Chemical class 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 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 2
- QBHRODVYNZFUMW-UHFFFAOYSA-N 3-methyl-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidin-4-one Chemical compound O=C1C(C)=CN=C2CCCN21 QBHRODVYNZFUMW-UHFFFAOYSA-N 0.000 description 2
- UZURIMJIPBRTBY-UHFFFAOYSA-N 3-phenyl-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidin-2-one Chemical compound O=C1N=C2CCCN2C=C1C1=CC=CC=C1 UZURIMJIPBRTBY-UHFFFAOYSA-N 0.000 description 2
- YBDQDRXVEDGNOI-UHFFFAOYSA-N 3-phenyl-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidin-4-one Chemical compound C=1N=C2CCCN2C(=O)C=1C1=CC=CC=C1 YBDQDRXVEDGNOI-UHFFFAOYSA-N 0.000 description 2
- FIIXTQKDPFFJFO-UHFFFAOYSA-N 4-oxo-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidine-3-carboxamide Chemical compound O=C1C(C(=O)N)=CN=C2CCCN21 FIIXTQKDPFFJFO-UHFFFAOYSA-N 0.000 description 2
- LNRTVAGIGIAARK-UHFFFAOYSA-N 4-oxo-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidine-3-carboxylic acid Chemical compound O=C1C(C(=O)O)=CN=C2CCCN21 LNRTVAGIGIAARK-UHFFFAOYSA-N 0.000 description 2
- KRYURACLPUIPBO-UHFFFAOYSA-N 7,8-Dihydro-3-methylpyrrolo[1,2-a]pyrimidin-2(6H)-one Chemical compound O=C1C(C)=CN2CCCC2=N1 KRYURACLPUIPBO-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- XWIUIRQSQROZGJ-UHFFFAOYSA-N ethyl 2-(2-formylphenyl)acetate Chemical compound CCOC(=O)CC1=CC=CC=C1C=O XWIUIRQSQROZGJ-UHFFFAOYSA-N 0.000 description 2
- WXOQPVPCAAVXOV-UHFFFAOYSA-N ethyl 4-oxo-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidine-3-carboxylate Chemical compound O=C1C(C(=O)OCC)=CN=C2CCCN21 WXOQPVPCAAVXOV-UHFFFAOYSA-N 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 230000000297 inotrophic effect Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- ZSIALBZCWCLSOG-UHFFFAOYSA-N pyrimidine;hydroiodide Chemical compound I.C1=CN=CN=C1 ZSIALBZCWCLSOG-UHFFFAOYSA-N 0.000 description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- MWZBABGITKVXKB-UHFFFAOYSA-N 1-methyl-4-oxo-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidin-1-ium-3-carboxamide;methyl sulfate Chemical compound COS([O-])(=O)=O.C1=C(C(N)=O)C(=O)N2CCCC2=[N+]1C MWZBABGITKVXKB-UHFFFAOYSA-N 0.000 description 1
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical class O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 1
- YXWVHJSAAGVQMQ-UHFFFAOYSA-N 1h-pyrrolo[1,2-a]pyrimidin-2-one Chemical compound N1C(=O)C=CN2C=CC=C21 YXWVHJSAAGVQMQ-UHFFFAOYSA-N 0.000 description 1
- MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 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
- PQCNCYLRDPVQDB-UHFFFAOYSA-N 2-methyl-2,3-dihydro-1h-pyrrol-5-amine Chemical compound CC1CC=C(N)N1 PQCNCYLRDPVQDB-UHFFFAOYSA-N 0.000 description 1
- BFWIEFMIJQMCCG-UHFFFAOYSA-N 2-oxo-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidine-3-carbohydrazide Chemical compound O=C1C(C(=O)NN)=CN2CCCC2=N1 BFWIEFMIJQMCCG-UHFFFAOYSA-N 0.000 description 1
- AVLHVNKKTRBNFT-UHFFFAOYSA-N 2-oxo-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidine-3-carboxylic acid Chemical compound O=C1C(C(=O)O)=CN2CCCC2=N1 AVLHVNKKTRBNFT-UHFFFAOYSA-N 0.000 description 1
- LYMLIEWJWWFMOW-UHFFFAOYSA-N 2H-pyrimidine-1-carbohydrazide Chemical compound NNC(=O)N1CN=CC=C1 LYMLIEWJWWFMOW-UHFFFAOYSA-N 0.000 description 1
- SVQKXZYJADNQFF-UHFFFAOYSA-N 2H-pyrimidine-1-carboxylic acid hydrochloride Chemical compound Cl.OC(=O)N1CN=CC=C1 SVQKXZYJADNQFF-UHFFFAOYSA-N 0.000 description 1
- MTDGTZKRYXZSMA-UHFFFAOYSA-N 3,6-dimethyl-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidin-4-one Chemical compound C1=C(C)C(=O)N2C(C)CCC2=N1 MTDGTZKRYXZSMA-UHFFFAOYSA-N 0.000 description 1
- GJUCKMAZGUZQMM-UHFFFAOYSA-N 3-ethyl-2-methyl-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidin-4-one Chemical compound O=C1C(CC)=C(C)N=C2CCCN21 GJUCKMAZGUZQMM-UHFFFAOYSA-N 0.000 description 1
- PQVHMOLNSYFXIJ-UHFFFAOYSA-N 4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]pyrazole-3-carboxylic acid Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(N1CC2=C(CC1)NN=N2)=O)C(=O)O PQVHMOLNSYFXIJ-UHFFFAOYSA-N 0.000 description 1
- DZXWMORFICYADZ-UHFFFAOYSA-N 4-oxo-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidine-3-carbonitrile Chemical compound O=C1C(C#N)=CN=C2CCCN12 DZXWMORFICYADZ-UHFFFAOYSA-N 0.000 description 1
- SZJBTCYRDPBPDP-UHFFFAOYSA-N 6-methyl-3-phenyl-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidin-2-one Chemical compound C=1N2C(C)CCC2=NC(=O)C=1C1=CC=CC=C1 SZJBTCYRDPBPDP-UHFFFAOYSA-N 0.000 description 1
- VNMVJRDSSOQOJA-UHFFFAOYSA-N 6-methyl-4-oxo-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidine-3-carbonitrile Chemical compound C1=C(C#N)C(=O)N2C(C)CCC2=N1 VNMVJRDSSOQOJA-UHFFFAOYSA-N 0.000 description 1
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
- YIOSBVGXNFWVER-UHFFFAOYSA-N 7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidin-4-one Chemical compound O=C1C=CN=C2CCCN12 YIOSBVGXNFWVER-UHFFFAOYSA-N 0.000 description 1
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
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- 239000005695 Ammonium acetate Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- UAXKROOTZSAURN-UHFFFAOYSA-N C(C)OC(=O)C1C(N=C2N(C1)CCC2)=O Chemical compound C(C)OC(=O)C1C(N=C2N(C1)CCC2)=O UAXKROOTZSAURN-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010052895 Coronary artery insufficiency Diseases 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- UJVJGYQUOOQTAW-UHFFFAOYSA-N Pyrimine Natural products OC(=O)C1CCC(C=2N=CC=CC=2)=N1 UJVJGYQUOOQTAW-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 description 1
- 102000002852 Vasopressins Human genes 0.000 description 1
- 108010004977 Vasopressins Proteins 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- WLXALCKAKGDNAT-UHFFFAOYSA-N diazoethane Chemical compound CC=[N+]=[N-] WLXALCKAKGDNAT-UHFFFAOYSA-N 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- DBPZGIYFXPPTLH-UHFFFAOYSA-M ethyl 1,6-dimethyl-4-oxo-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidin-1-ium-3-carboxylate;iodide Chemical compound [I-].O=C1C(C(=O)OCC)=C[N+](C)=C2CCC(C)N21 DBPZGIYFXPPTLH-UHFFFAOYSA-M 0.000 description 1
- OKANYBNORCUPKZ-UHFFFAOYSA-N ethyl 2-ethyl-3-oxobutanoate Chemical compound CCOC(=O)C(CC)C(C)=O OKANYBNORCUPKZ-UHFFFAOYSA-N 0.000 description 1
- GBLDIXVFALGTKZ-UHFFFAOYSA-N ethyl 6-methyl-2-oxo-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidine-3-carboxylate Chemical compound O=C1C(C(=O)OCC)=CN2C(C)CCC2=N1 GBLDIXVFALGTKZ-UHFFFAOYSA-N 0.000 description 1
- LMJSWYGTDLUTNW-UHFFFAOYSA-N ethyl 6-methyl-4-oxo-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidine-3-carboxylate Chemical compound O=C1C(C(=O)OCC)=CN=C2CCC(C)N21 LMJSWYGTDLUTNW-UHFFFAOYSA-N 0.000 description 1
- BAUGGERDLBPICM-UHFFFAOYSA-N ethyl 6-methyl-4-oxo-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidine-3-carboxylate;hydrochloride Chemical compound Cl.O=C1C(C(=O)OCC)=CN=C2CCC(C)N21 BAUGGERDLBPICM-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000005240 left ventricle Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229960001789 papaverine Drugs 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 210000004197 pelvis Anatomy 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- ACLAUFPCYXSVEK-UHFFFAOYSA-N pyrrolo[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C1=C(C(=O)O)C=NC2=CC=CN21 ACLAUFPCYXSVEK-UHFFFAOYSA-N 0.000 description 1
- DXVAQZJPPDWTNY-UHFFFAOYSA-N pyrrolo[3,2-d]pyrimidin-2-one Chemical class O=C1N=CC2=NC=CC2=N1 DXVAQZJPPDWTNY-UHFFFAOYSA-N 0.000 description 1
- 150000004944 pyrrolopyrimidines Chemical class 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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
- 229960003726 vasopressin Drugs 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Cardiology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79CI1930A HU176942B (hu) | 1979-05-11 | 1979-05-11 | Sposob poluchenija 2,3- i 3,4-dvuzamehhjonnykh tetragidro-pirrolo!1,2-a!-pirimidinov |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8003477L SE8003477L (sv) | 1980-11-12 |
| SE437030B true SE437030B (sv) | 1985-02-04 |
Family
ID=10994745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8003477A SE437030B (sv) | 1979-05-11 | 1980-05-08 | 3-substituerade tetrahydro-pyrrolo/1,2-a/pyrimidiner, forfarande for framstellning derav och farmaceutiska preparat innehallande dessa foreningar |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4367229A (enExample) |
| JP (1) | JPS565479A (enExample) |
| AR (1) | AR225308A1 (enExample) |
| AU (1) | AU539466B2 (enExample) |
| BE (1) | BE883215A (enExample) |
| CA (1) | CA1149806A (enExample) |
| CH (1) | CH649551A5 (enExample) |
| CS (1) | CS221550B2 (enExample) |
| DD (1) | DD150612A5 (enExample) |
| DE (1) | DE3017625A1 (enExample) |
| DK (1) | DK152501C (enExample) |
| ES (1) | ES8104293A1 (enExample) |
| FI (1) | FI70218C (enExample) |
| FR (1) | FR2456105A1 (enExample) |
| GB (1) | GB2049694B (enExample) |
| GR (1) | GR68516B (enExample) |
| HU (1) | HU176942B (enExample) |
| IL (1) | IL59987A (enExample) |
| IT (1) | IT1147735B (enExample) |
| LU (1) | LU82435A1 (enExample) |
| NL (1) | NL8002682A (enExample) |
| NO (1) | NO155773C (enExample) |
| PL (1) | PL123709B1 (enExample) |
| PT (1) | PT71211A (enExample) |
| SE (1) | SE437030B (enExample) |
| SU (1) | SU1048986A3 (enExample) |
| YU (1) | YU122080A (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4482557A (en) * | 1979-05-11 | 1984-11-13 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. | 3-Substituted-2-oxo-tetrahydro-pyrrol[1,2-a]pyrimidines having digitalis-like activity |
| CA1211111A (en) * | 1982-02-15 | 1986-09-09 | Isao Yanagisawa | Process for preparing novel pyrimidone compounds |
| US5344933A (en) * | 1991-09-11 | 1994-09-06 | Fuji Photo Film Co., Ltd. | Pyrrole ring-or condensed pyrrole ring-containing azomethine dye |
| AU719308B2 (en) | 1997-01-22 | 2000-05-04 | Ciba Specialty Chemicals Holding Inc. | Photoactivatable nitrogen-containing bases based on alpha-amino ketones |
| JP2000026465A (ja) * | 1998-07-14 | 2000-01-25 | Fuji Photo Film Co Ltd | ピロロ［１，２−ａ］ピリミジン化合物及びそれを用いた感熱記録材料 |
| US11983498B2 (en) * | 2021-03-18 | 2024-05-14 | Augmented Intelligence Technologies, Inc. | System and methods for language processing of document sequences using a neural network |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1803758U (de) | 1959-09-03 | 1960-01-07 | Eugen Haller | Spritz- und spanschutz -geraet. |
| DE1795769C3 (de) * | 1966-11-02 | 1978-11-02 | Chinoin Gyogyszer- Es Vegyeszeti Termekek Gyara Rt, Budapest | 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 |
| DE1803785A1 (de) * | 1968-10-18 | 1970-06-04 | Hoechst Ag | Verfahren zur Herstellung von 1,2-disubstituierten 6-Oxo-1.4.5.6-tetrahydropyrimidinen |
| BE788601A (fr) * | 1971-09-10 | 1973-03-08 | Takeda Chemical Industries Ltd | Procede de preparation de derives de pyrimidine |
| HU167676B (enExample) | 1972-11-29 | 1975-11-28 | ||
| 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 |
| HU178496B (en) * | 1977-12-29 | 1982-05-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing 6,7,8,9-tetrahydro-4h-pyrido/1,2-a/pyrimidine derivatives with antiallergic activity |
-
1979
- 1979-05-11 HU HU79CI1930A patent/HU176942B/hu not_active IP Right Cessation
-
1980
- 1980-05-03 ES ES491153A patent/ES8104293A1/es not_active Expired
- 1980-05-03 GR GR61849A patent/GR68516B/el unknown
- 1980-05-04 IL IL59987A patent/IL59987A/xx unknown
- 1980-05-06 CS CS803171A patent/CS221550B2/cs unknown
- 1980-05-08 DE DE19803017625 patent/DE3017625A1/de not_active Withdrawn
- 1980-05-08 PL PL1980224124A patent/PL123709B1/pl unknown
- 1980-05-08 SU SU802919651A patent/SU1048986A3/ru active
- 1980-05-08 SE SE8003477A patent/SE437030B/sv not_active IP Right Cessation
- 1980-05-08 YU YU01220/80A patent/YU122080A/xx unknown
- 1980-05-09 BE BE0/200548A patent/BE883215A/fr not_active IP Right Cessation
- 1980-05-09 JP JP6161380A patent/JPS565479A/ja active Pending
- 1980-05-09 FR FR8010477A patent/FR2456105A1/fr active Granted
- 1980-05-09 CH CH3661/80A patent/CH649551A5/de not_active IP Right Cessation
- 1980-05-09 IT IT67738/80A patent/IT1147735B/it active
- 1980-05-09 DD DD80220986A patent/DD150612A5/de not_active IP Right Cessation
- 1980-05-09 DK DK204880A patent/DK152501C/da not_active IP Right Cessation
- 1980-05-09 FI FI801515A patent/FI70218C/fi not_active IP Right Cessation
- 1980-05-09 AR AR280967A patent/AR225308A1/es active
- 1980-05-09 NL NL8002682A patent/NL8002682A/nl not_active Application Discontinuation
- 1980-05-09 CA CA000351663A patent/CA1149806A/en not_active Expired
- 1980-05-09 GB GB8015420A patent/GB2049694B/en not_active Expired
- 1980-05-09 PT PT71211A patent/PT71211A/pt unknown
- 1980-05-09 LU LU82435A patent/LU82435A1/de unknown
- 1980-05-09 AU AU58276/80A patent/AU539466B2/en not_active Ceased
- 1980-05-09 NO NO801376A patent/NO155773C/no unknown
- 1980-05-09 US US06/148,239 patent/US4367229A/en not_active Expired - Lifetime
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