CS221550B2 - Method of making the 2,3-and 3,4-disubstituted tetrahydropropyrollo /1,2-a/pyrimidine,mixture thereof and salts - Google Patents
Method of making the 2,3-and 3,4-disubstituted tetrahydropropyrollo /1,2-a/pyrimidine,mixture thereof and salts Download PDFInfo
- Publication number
- CS221550B2 CS221550B2 CS803171A CS317180A CS221550B2 CS 221550 B2 CS221550 B2 CS 221550B2 CS 803171 A CS803171 A CS 803171A CS 317180 A CS317180 A CS 317180A CS 221550 B2 CS221550 B2 CS 221550B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- group
- pyrimidine
- oxo
- pyrrolo
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 26
- 150000003839 salts Chemical class 0.000 title claims abstract description 16
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 42
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 20
- -1 3,4-disubstituted, tetrahydropyrrolo [1,2-a] pyrimidines Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 235000019271 petrolatum Nutrition 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 150000008282 halocarbons Chemical class 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 125000002560 nitrile group Chemical group 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 101100421674 Drosophila melanogaster slou gene Proteins 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
- 229910052757 nitrogen Inorganic materials 0.000 description 37
- 239000000243 solution Substances 0.000 description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
- 239000000155 melt Substances 0.000 description 25
- 239000013078 crystal Substances 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- AHFWKTKIRQCWCQ-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrol-5-amine Chemical class NC1=CCCN1 AHFWKTKIRQCWCQ-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- CSOYDALHEQEMAK-UHFFFAOYSA-N 2h-pyrimidine-1-carboxylic acid Chemical compound OC(=O)N1CN=CC=C1 CSOYDALHEQEMAK-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 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 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- PQCNCYLRDPVQDB-UHFFFAOYSA-N 2-methyl-2,3-dihydro-1h-pyrrol-5-amine Chemical group CC1CC=C(N)N1 PQCNCYLRDPVQDB-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 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
- 238000001816 cooling Methods 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- ZSIALBZCWCLSOG-UHFFFAOYSA-N pyrimidine;hydroiodide Chemical compound I.C1=CN=CN=C1 ZSIALBZCWCLSOG-UHFFFAOYSA-N 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 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
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XHUWDDXMORFULQ-UHFFFAOYSA-N ethyl 2h-pyrimidine-1-carboxylate Chemical compound CCOC(=O)N1CN=CC=C1 XHUWDDXMORFULQ-UHFFFAOYSA-N 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 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
- 150000002576 ketones Chemical class 0.000 description 2
- 239000012452 mother liquor Substances 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
- 239000003208 petroleum Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 150000003230 pyrimidines Chemical group 0.000 description 2
- JBDKAABFESSFMV-UHFFFAOYSA-N pyrrolo[1,2-a]pyrimidine Chemical class N1=CC=CN2C=CC=C21 JBDKAABFESSFMV-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- NLFAKPCNQNYINV-UHFFFAOYSA-N 2-(2-methylphenyl)butanoic acid Chemical compound CCC(C(O)=O)C1=CC=CC=C1C NLFAKPCNQNYINV-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
- CTSZPNIMMLSKDV-UHFFFAOYSA-N 2-methyl-1-pyrroline Chemical compound CC1=NCCC1 CTSZPNIMMLSKDV-UHFFFAOYSA-N 0.000 description 1
- JSTDQAGCAJCGDO-UHFFFAOYSA-N 2-oxo-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidine-3-carboxamide Chemical compound O=C1C(C(=O)N)=CN2CCCC2=N1 JSTDQAGCAJCGDO-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
- FOLFNFLOCQXIKY-UHFFFAOYSA-N 3-ethyl-2-methyl-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidin-4-one;hydrochloride Chemical compound Cl.O=C1C(CC)=C(C)N=C2CCCN21 FOLFNFLOCQXIKY-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
- 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 1
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 1
- SXQZMOCWTDSEPM-UHFFFAOYSA-N 6-methyl-2-oxo-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidine-3-carboxamide Chemical compound O=C1C(C(N)=O)=CN2C(C)CCC2=N1 SXQZMOCWTDSEPM-UHFFFAOYSA-N 0.000 description 1
- WUXKYIXAKPFHHT-UHFFFAOYSA-N 6-methyl-4-oxo-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidine-3-carboxamide Chemical compound C1=C(C(N)=O)C(=O)N2C(C)CCC2=N1 WUXKYIXAKPFHHT-UHFFFAOYSA-N 0.000 description 1
- UXZKYCSZTAPQDA-UHFFFAOYSA-N 6-methyl-4-oxo-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)N2C(C)CCC2=N1 UXZKYCSZTAPQDA-UHFFFAOYSA-N 0.000 description 1
- VAOLNWDEJMUXOX-UHFFFAOYSA-N 6-methyl-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidin-4-one Chemical compound C1=CC(=O)N2C(C)CCC2=N1 VAOLNWDEJMUXOX-UHFFFAOYSA-N 0.000 description 1
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
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- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
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- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 240000002871 Tectona grandis Species 0.000 description 1
- 241000404967 Toxotes Species 0.000 description 1
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- 125000004429 atom Chemical group 0.000 description 1
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- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 1
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- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 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
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 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
- KTMGNAIGXYODKQ-UHFFFAOYSA-N ethyl 2-cyano-3-ethoxyprop-2-enoate Chemical compound CCOC=C(C#N)C(=O)OCC KTMGNAIGXYODKQ-UHFFFAOYSA-N 0.000 description 1
- VVCYNVCCODBCOE-UHFFFAOYSA-N ethyl 2-methyl-3-oxopropanoate Chemical compound CCOC(=O)C(C)C=O VVCYNVCCODBCOE-UHFFFAOYSA-N 0.000 description 1
- XMXAWIPGXLYXFH-UHFFFAOYSA-N ethyl 4-oxo-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidine-3-carboxylate;hydrochloride Chemical compound Cl.O=C1C(C(=O)OCC)=CN=C2CCCN21 XMXAWIPGXLYXFH-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
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N gamma-butyrolactam Natural products O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 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
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- GOIKXGFPCJOMFO-UHFFFAOYSA-N methyl sulfate;pyrimidin-1-ium Chemical compound COS([O-])(=O)=O.C1=CN=C[NH+]=C1 GOIKXGFPCJOMFO-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 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
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- HNJBEVLQSNELDL-YZRHJBSPSA-N pyrrolidin-2-one Chemical group O=C1CC[14CH2]N1 HNJBEVLQSNELDL-YZRHJBSPSA-N 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur 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
- 229940104230 thymidine Drugs 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
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 (1)
| Publication Number | Publication Date |
|---|---|
| CS221550B2 true CS221550B2 (en) | 1983-04-29 |
Family
ID=10994745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS803171A CS221550B2 (en) | 1979-05-11 | 1980-05-06 | Method of making the 2,3-and 3,4-disubstituted tetrahydropropyrollo /1,2-a/pyrimidine,mixture thereof and salts |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4367229A (OSRAM) |
| JP (1) | JPS565479A (OSRAM) |
| AR (1) | AR225308A1 (OSRAM) |
| AU (1) | AU539466B2 (OSRAM) |
| BE (1) | BE883215A (OSRAM) |
| CA (1) | CA1149806A (OSRAM) |
| CH (1) | CH649551A5 (OSRAM) |
| CS (1) | CS221550B2 (OSRAM) |
| DD (1) | DD150612A5 (OSRAM) |
| DE (1) | DE3017625A1 (OSRAM) |
| DK (1) | DK152501C (OSRAM) |
| ES (1) | ES8104293A1 (OSRAM) |
| FI (1) | FI70218C (OSRAM) |
| FR (1) | FR2456105A1 (OSRAM) |
| GB (1) | GB2049694B (OSRAM) |
| GR (1) | GR68516B (OSRAM) |
| HU (1) | HU176942B (OSRAM) |
| IL (1) | IL59987A (OSRAM) |
| IT (1) | IT1147735B (OSRAM) |
| LU (1) | LU82435A1 (OSRAM) |
| NL (1) | NL8002682A (OSRAM) |
| NO (1) | NO155773C (OSRAM) |
| PL (1) | PL123709B1 (OSRAM) |
| PT (1) | PT71211A (OSRAM) |
| SE (1) | SE437030B (OSRAM) |
| SU (1) | SU1048986A3 (OSRAM) |
| YU (1) | YU122080A (OSRAM) |
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 (OSRAM) | 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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