HU176942B - Sposob poluchenija 2,3- i 3,4-dvuzamehhjonnykh tetragidro-pirrolo!1,2-a!-pirimidinov - Google Patents
Sposob poluchenija 2,3- i 3,4-dvuzamehhjonnykh tetragidro-pirrolo!1,2-a!-pirimidinov Download PDFInfo
- Publication number
- HU176942B HU176942B HU79CI1930A HUCI001930A HU176942B HU 176942 B HU176942 B HU 176942B HU 79CI1930 A HU79CI1930 A HU 79CI1930A HU CI001930 A HUCI001930 A HU CI001930A HU 176942 B HU176942 B HU 176942B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- compound
- ethyl
- oxo
- pyrimidine
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 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 abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 44
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- -1 diethyl ethoxymethylene methyl Chemical group 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- OKANYBNORCUPKZ-UHFFFAOYSA-N ethyl 2-ethyl-3-oxobutanoate Chemical compound CCOC(=O)C(CC)C(C)=O OKANYBNORCUPKZ-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
- 239000007858 starting material Substances 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- CYXQJHOJIQTXLE-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrolizine Chemical class C1=CN2CCCC2=C1 CYXQJHOJIQTXLE-UHFFFAOYSA-N 0.000 claims 1
- GKECDORWWXXNRY-UHFFFAOYSA-N 2h-pyridin-3-one Chemical compound O=C1CN=CC=C1 GKECDORWWXXNRY-UHFFFAOYSA-N 0.000 claims 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- UXBNAFJJFIQVQN-UHFFFAOYSA-N cinnoline-3-carbohydrazide Chemical compound N1=NC(=CC2=CC=CC=C12)C(=O)NN UXBNAFJJFIQVQN-UHFFFAOYSA-N 0.000 claims 1
- XWIUIRQSQROZGJ-UHFFFAOYSA-N ethyl 2-(2-formylphenyl)acetate Chemical compound CCOC(=O)CC1=CC=CC=C1C=O XWIUIRQSQROZGJ-UHFFFAOYSA-N 0.000 claims 1
- VVCYNVCCODBCOE-UHFFFAOYSA-N ethyl 2-methyl-3-oxopropanoate Chemical compound CCOC(=O)C(C)C=O VVCYNVCCODBCOE-UHFFFAOYSA-N 0.000 claims 1
- 238000001640 fractional crystallisation Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 abstract description 6
- AHFWKTKIRQCWCQ-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrol-5-amine Chemical compound NC1=CCCN1 AHFWKTKIRQCWCQ-UHFFFAOYSA-N 0.000 abstract description 4
- 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 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
- 238000000921 elemental analysis Methods 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 239000013078 crystal Substances 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- CSOYDALHEQEMAK-UHFFFAOYSA-N 2h-pyrimidine-1-carboxylic acid Chemical compound OC(=O)N1CN=CC=C1 CSOYDALHEQEMAK-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 8
- NJBMZYSKLWQXLJ-UHFFFAOYSA-N 3,4-dihydro-2h-pyrrol-5-amine Chemical compound NC1=NCCC1 NJBMZYSKLWQXLJ-UHFFFAOYSA-N 0.000 description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000003857 carboxamides Chemical class 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 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 3
- 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 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- DDQFWSHGBVMBEM-UHFFFAOYSA-N 2-methyl-3,4-dihydro-2h-pyrrol-5-amine Chemical compound CC1CCC(N)=N1 DDQFWSHGBVMBEM-UHFFFAOYSA-N 0.000 description 2
- SVQKXZYJADNQFF-UHFFFAOYSA-N 2H-pyrimidine-1-carboxylic acid hydrochloride Chemical compound Cl.OC(=O)N1CN=CC=C1 SVQKXZYJADNQFF-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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 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 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 239000000047 product Substances 0.000 description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 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
- 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
- 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
- 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
- BBNOFIWVEKYAFR-UHFFFAOYSA-N 6-methyl-2-oxo-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidine-3-carbohydrazide;hydrochloride Chemical compound Cl.O=C1C(C(=O)NN)=CN2C(C)CCC2=N1 BBNOFIWVEKYAFR-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
- 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
- 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 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-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
- 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
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- AVMNFQHJOOYCAP-UHFFFAOYSA-N acetic acid;propanoic acid Chemical compound CC(O)=O.CCC(O)=O AVMNFQHJOOYCAP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000003257 anti-anginal effect Effects 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
- 230000009286 beneficial effect Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 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
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 239000012153 distilled water Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- ABKSWKSXYNINDR-UHFFFAOYSA-M ethyl 1-methyl-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)=C2CCCN21 ABKSWKSXYNINDR-UHFFFAOYSA-M 0.000 description 1
- 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 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical compound Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
- 239000004922 lacquer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 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
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- ZJMLWSBTWUELPE-UHFFFAOYSA-N oxo(phenyl)methanesulfonic acid Chemical compound OS(=O)(=O)C(=O)C1=CC=CC=C1 ZJMLWSBTWUELPE-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- ZSIALBZCWCLSOG-UHFFFAOYSA-N pyrimidine;hydroiodide Chemical compound I.C1=CN=CN=C1 ZSIALBZCWCLSOG-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- JXAZAUKOWVKTLO-UHFFFAOYSA-L sodium pyrosulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OS([O-])(=O)=O JXAZAUKOWVKTLO-UHFFFAOYSA-L 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 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
- 230000001256 tonic effect Effects 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)
Priority Applications (30)
| 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 |
| ES491153A ES8104293A1 (es) | 1979-05-11 | 1980-05-03 | Procedimiento de preparar derivados pirrolo(1,2-a)pirimidi- nicos |
| GR61849A GR68516B (OSRAM) | 1979-05-11 | 1980-05-03 | |
| IL59987A IL59987A (en) | 1979-05-11 | 1980-05-04 | Antianginal compositions containing 3-substituted-tetrahydro-pyrrolo(1,2-a)pyrimidinone derivatives and some new 3-substituted-tetrahydro-pyrrolo(1,2-a)pyrimidin-2-ones |
| 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 |
| SU802919651A SU1048986A3 (ru) | 1979-05-11 | 1980-05-08 | Способ получени 3-замещенных тетрагидропирроло/1,2- @ / пиримидинов,их кислотно-аддитивных или четвертичных солей |
| YU01220/80A YU122080A (en) | 1979-05-11 | 1980-05-08 | Process for obtaining geminal dihalo derivatives of condensed pyrimidin-4-one compounds |
| PL1980224124A PL123709B1 (en) | 1979-05-11 | 1980-05-08 | Process for preparing 3-substituted tetrahydropyrrole/1,2-a/pyrimidines |
| 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 |
| DE19803017625 DE3017625A1 (de) | 1979-05-11 | 1980-05-08 | Verfahren zur herstellung von 3-substituierten tetrahydro-pyrrolo eckige klammer auf 1,2-a eckige klammer zu pyrimidinen und die verbindungen enthaltende pharmazeutische praeparate sowie neue 3-substituierte-tetrahydro-pyrrolo eckige klammer auf 1,2-a eckige klammer zu pyrimidine |
| DK204880A DK152501C (da) | 1979-05-11 | 1980-05-09 | Fremgangsmaade til fremstilling af pyrrolooe1,2-aaapyrimidiner eller salte deraf |
| GB8015420A GB2049694B (en) | 1979-05-11 | 1980-05-09 | Anti-anginal 3-substituted-tetrahydropyrolo(1,2)pyrimidines |
| FR8010477A FR2456105A1 (fr) | 1979-05-11 | 1980-05-09 | Procede pour la preparation de tetrahydro-pyrrolo (1,2-a) pyrimidines substituees en position 3, compositions pharmaceutiques contenant ces composes et nouvelles tetrahydro-pyrrolo (1,2-a) pyrimidines substituees en position 3 |
| FI801515A FI70218C (fi) | 1979-05-11 | 1980-05-09 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 3-substituerade tetrahydropyrrolo/1,2-a/pyrimidiner |
| AU58276/80A AU539466B2 (en) | 1979-05-11 | 1980-05-09 | Tetrahydro-pyrrolo/1,2-a/pyrimidines |
| NO801376A NO155773C (no) | 1979-05-11 | 1980-05-09 | Analogifremgangsmaate ved fremstilling av terapeutisk aktive 3-substituerte tetrahydropyrrolo (1,2-a) pyrimidinderivater. |
| IT67738/80A IT1147735B (it) | 1979-05-11 | 1980-05-09 | Procedimento per la preparazione di tetraido pirrolo (1,2-a) pirimidine 3-sostituite,composizioni faramceutiche che le contengono e tetraidro pirrolo (1,2-a) pirimidine 3-sosti-tuite |
| DD80220986A DD150612A5 (de) | 1979-05-11 | 1980-05-09 | Verfahren zur herstellung von 3-substituierten tetrahydro-pyrrolo(1,2-a)pyrimidinen |
| AR280967A AR225308A1 (es) | 1979-05-11 | 1980-05-09 | Procedimiento para producir tetrahidro-pirrolo(1,2-a)pirimidinas sustituidas en posicion 3 |
| PT71211A PT71211A (en) | 1979-05-11 | 1980-05-09 | Process for the preparation of 3-substituted-tetrahydropyrrolo/1,2-a/pyrimidines and pharmaceutical compositions containing the same and new 3-substituted-tetrahydro-pyrrolo/1,2-a/ pyrimidines |
| NL8002682A NL8002682A (nl) | 1979-05-11 | 1980-05-09 | Werkwijze voor de bereiding van 3-gesubstitueerde terahydro-pyrrolo/1,2-a/pyrimidinen en farmaceutische preparaten die deze verbindingen bevatten, alsmede nieuwe 3-gesubstitueerde tetrahydropyrrolo/1,2-a/ pyrimidinen. |
| BE0/200548A BE883215A (fr) | 1979-05-11 | 1980-05-09 | Tetrahydro-pyrrolo-(1,2-a) pyrimidines substituees en position 3, leur preparation et compositions pharmaceutique contenant ces composes |
| LU82435A LU82435A1 (de) | 1979-05-11 | 1980-05-09 | Verfahren zur herstellung von 3-substituierten tetrahydropyrrolo(1,2-a)pyrimidinen,und die verbindungen enthaltende pharmazeutische praeparate sowie neue 3-substituierte-tetrahydropyrrolo(1,2-a)pyrimidine |
| US06/148,239 US4367229A (en) | 1979-05-11 | 1980-05-09 | 3-Substituted-tetrahydro-pyrrolo[1,2-a]pyrimidines and pharmaceutical compositions |
| CH3661/80A CH649551A5 (de) | 1979-05-11 | 1980-05-09 | 3-substituierte-tetrahydro-pyrrolo(1,2-a)pyrimidine, verfahren zu ihrer herstellung sowie ihrer verwendung in pharmazeutischen praeparaten. |
| AT247480A AT384221B (de) | 1979-05-11 | 1980-05-09 | Verfahren zur herstellung von neuen 3-substituierten tetrahydro-pyrrolo(1,2-a) pyrimidin-derivaten sowie von deren saeureadditions- und quaternaeren salzen |
| JP6161380A JPS565479A (en) | 1979-05-11 | 1980-05-09 | Novel 33substituteddtetrahydropyrrolopyrimidines and their manufacture |
| CA000351663A CA1149806A (en) | 1979-05-11 | 1980-05-09 | 3-substituted-tetrahydro-pyrrolo[1,2-a] pyrimidines, process for the preparation thereof and pharmaceutical compositions containing the same |
| US06/416,130 US4482557A (en) | 1979-05-11 | 1982-09-09 | 3-Substituted-2-oxo-tetrahydro-pyrrol[1,2-a]pyrimidines having digitalis-like activity |
| AT16784A AT391079B (de) | 1979-05-11 | 1984-01-19 | Verwendung von 3-substituierten tetrahydropyrrolo(1,2-a)pyrimidin-derivaten sowie von deren saeureadditions- und quaternaeren salzen zur herstellung von pharmazeutischen praeparaten |
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 |
|---|---|
| HU176942B true HU176942B (hu) | 1981-06-28 |
Family
ID=10994745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU79CI1930A HU176942B (hu) | 1979-05-11 | 1979-05-11 | Sposob poluchenija 2,3- i 3,4-dvuzamehhjonnykh tetragidro-pirrolo!1,2-a!-pirimidinov |
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
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3388129A (en) | 1-methyl ergot alkaloids | |
| US3755340A (en) | Amino derivatives of pyrazolopyridine carboxylic acids and esters | |
| US2924603A (en) | Aralkylbenzmorphan derivatives | |
| DK161966B (da) | Fremgangsmaade til fremstilling af 5-aroylerede 1,2-dihydro-3h-pyrrolooe1,2-aaapyrrol-1-carboxylsyrer eller estere eller farmaceutisk acceptable salte deraf | |
| HU176942B (hu) | Sposob poluchenija 2,3- i 3,4-dvuzamehhjonnykh tetragidro-pirrolo!1,2-a!-pirimidinov | |
| US3526636A (en) | Imidazoisoindoles | |
| IE52289B1 (en) | 2-amino-3(halobenzoyl)-methylphenylacetic acids,esters and salts thereof | |
| US3681355A (en) | Ergonarcarnines | |
| IL26725A (en) | Benzodiazepine derivatives and process for the manufacture thereof | |
| US3086972A (en) | Aza-thiaxanthene derivatives | |
| US4404205A (en) | 2-Oxo-2,6,7,8,9,10 hexahydro-pyrimido[1,2-a]azepines and antianginal method of use thereof and of 4-oxo-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepines | |
| US3426017A (en) | Sulfonylurea compounds | |
| US3882119A (en) | Tetracyclic substituted phthalazine compounds | |
| US3928368A (en) | Alcohol derivatives of pyrazolo{8 3,4-b{9 pyridines | |
| US4482557A (en) | 3-Substituted-2-oxo-tetrahydro-pyrrol[1,2-a]pyrimidines having digitalis-like activity | |
| US2807616A (en) | Oxazolopyrimidines and method of preparing same | |
| IL34468A (en) | Acidic salt salts of the history of indonopyridine, their preparation and pharmaceutical preparations containing them | |
| JPS6210996B2 (OSRAM) | ||
| EP0258048B1 (en) | 2-amino-3-aroyl-gamma-oxobenzenebutanoic acids and esters | |
| US3953465A (en) | 2-[α-(3-Trifluoromethylphenoxyl)-4-chlorobenzyl]oxazole and methods for preparing the same | |
| US4156728A (en) | 3-Substituted-2(1H)pyridone-6-carboxylic acids | |
| IL34689A (en) | 1h-2,3,4,5-tetrahydro-1,5-benzodiazepin-4-ones,their preparation and pharmaceutical compositions containing them | |
| US4054571A (en) | Nitrogen-containing polycyclic compounds and a process for the preparation thereof | |
| US3551430A (en) | Esters of hexahydro - 9,10 - dialkoxy - 2h-benzo(a)quinolizine-1-propionic acid | |
| CA1192189A (en) | E-homo-eburnane derivatives and a process for preparing same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |