DD242045A5 - Neue pyrolo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel - Google Patents
Neue pyrolo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel Download PDFInfo
- Publication number
- DD242045A5 DD242045A5 DD85284206A DD28420685A DD242045A5 DD 242045 A5 DD242045 A5 DD 242045A5 DD 85284206 A DD85284206 A DD 85284206A DD 28420685 A DD28420685 A DD 28420685A DD 242045 A5 DD242045 A5 DD 242045A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- group
- pyrrolo
- dihydro
- compounds
- benzimidazol
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 12
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
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- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 10
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
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- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
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- CWNPEXKRKGHOEK-UHFFFAOYSA-N [4-(7,7-dimethyl-6-oxo-1,5-dihydropyrrolo[2,3-f]benzimidazol-2-yl)-3-methoxyphenyl]urea Chemical compound COC1=CC(NC(N)=O)=CC=C1C(NC1=C2)=NC1=CC1=C2NC(=O)C1(C)C CWNPEXKRKGHOEK-UHFFFAOYSA-N 0.000 description 1
- NSRZDDOMBYIBMG-UHFFFAOYSA-N [4-(7-carbamoyl-7-methyl-6-oxo-1,5-dihydropyrrolo[2,3-f]benzimidazol-2-yl)-3-methoxyphenyl] methanesulfonate Chemical compound COC1=CC(OS(C)(=O)=O)=CC=C1C(NC1=C2)=NC1=CC1=C2NC(=O)C1(C)C(N)=O NSRZDDOMBYIBMG-UHFFFAOYSA-N 0.000 description 1
- GKIJSMFSZVEYPE-UHFFFAOYSA-N [4-(7-cyano-7-methyl-6-oxo-1,5-dihydropyrrolo[2,3-f]benzimidazol-2-yl)-3-methoxyphenyl] methanesulfonate Chemical compound COC1=CC(OS(C)(=O)=O)=CC=C1C(NC1=C2)=NC1=CC1=C2NC(=O)C1(C)C#N GKIJSMFSZVEYPE-UHFFFAOYSA-N 0.000 description 1
- OPVKFWDKGKLHLK-UHFFFAOYSA-N [4-(7-ethyl-6-oxo-5,7-dihydro-1h-pyrrolo[2,3-f]benzimidazol-2-yl)-3-methoxyphenyl] trifluoromethanesulfonate Chemical compound N=1C=2C=C3C(CC)C(=O)NC3=CC=2NC=1C1=CC=C(OS(=O)(=O)C(F)(F)F)C=C1OC OPVKFWDKGKLHLK-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- WOXQTRUXNFNMDU-UHFFFAOYSA-N benzimidazol-5-one Chemical compound O=C1C=CC2=NC=NC2=C1 WOXQTRUXNFNMDU-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 150000004650 carbonic acid diesters Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- VHXCTSJJRXAEOG-UHFFFAOYSA-N chembl37055 Chemical compound N=1C=2C=C3C(C)(C)C(=O)NC3=CC=2NC=1C1=CC=C(O)C=C1 VHXCTSJJRXAEOG-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- PWAPCRSSMCLZHG-UHFFFAOYSA-N cyclopentylidene Chemical group [C]1CCCC1 PWAPCRSSMCLZHG-UHFFFAOYSA-N 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- ZXBPEFQLXCGHGI-UHFFFAOYSA-N ethyl 2-(2-methoxy-4-methylsulfonyloxyphenyl)-7-methyl-6-oxo-1,5-dihydropyrrolo[2,3-f]benzimidazole-7-carboxylate Chemical compound N1C=2C=C3C(C(=O)OCC)(C)C(=O)NC3=CC=2N=C1C1=CC=C(OS(C)(=O)=O)C=C1OC ZXBPEFQLXCGHGI-UHFFFAOYSA-N 0.000 description 1
- OMMBECRMRVYMNU-UHFFFAOYSA-N ethyl 2-(4-imidazol-1-ylphenyl)-7-methyl-6-oxo-1,5-dihydropyrrolo[2,3-f]benzimidazole-7-carboxylate Chemical compound N=1C=2C=C3C(C(=O)OCC)(C)C(=O)NC3=CC=2NC=1C(C=C1)=CC=C1N1C=CN=C1 OMMBECRMRVYMNU-UHFFFAOYSA-N 0.000 description 1
- KPMKGWOCQQVYQM-UHFFFAOYSA-N ethyl 2-[4-(methanesulfonamido)-2-methoxyphenyl]-7-methyl-6-oxo-1,5-dihydropyrrolo[2,3-f]benzimidazole-7-carboxylate Chemical compound N=1C=2C=C3C(C(=O)OCC)(C)C(=O)NC3=CC=2NC=1C1=CC=C(NS(C)(=O)=O)C=C1OC KPMKGWOCQQVYQM-UHFFFAOYSA-N 0.000 description 1
- WOWWECUMSNGXPS-UHFFFAOYSA-N ethyl 4-(7,7-dimethyl-6-oxo-1,5-dihydropyrrolo[2,3-f]benzimidazol-2-yl)-3-methoxybenzoate Chemical compound COC1=CC(C(=O)OCC)=CC=C1C(NC1=C2)=NC1=CC1=C2NC(=O)C1(C)C WOWWECUMSNGXPS-UHFFFAOYSA-N 0.000 description 1
- YQPMMOSBGXZXDY-UHFFFAOYSA-N ethyl 7-ethyl-2-[4-(methanesulfonamido)-2-methoxyphenyl]-6-oxo-1,5-dihydropyrrolo[2,3-f]benzimidazole-7-carboxylate Chemical compound N1C=2C=C3C(C(=O)OCC)(CC)C(=O)NC3=CC=2N=C1C1=CC=C(NS(C)(=O)=O)C=C1OC YQPMMOSBGXZXDY-UHFFFAOYSA-N 0.000 description 1
- WCWPPPIAUGCIFE-UHFFFAOYSA-N ethyl 7-methyl-6-oxo-2-phenyl-1,5-dihydropyrrolo[2,3-f]benzimidazole-7-carboxylate Chemical compound N1C=2C=C3C(C(=O)OCC)(C)C(=O)NC3=CC=2N=C1C1=CC=CC=C1 WCWPPPIAUGCIFE-UHFFFAOYSA-N 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- JHFHCNZDHHLPQG-UHFFFAOYSA-N methyl 2-(2-methoxy-4-methylsulfonyloxyphenyl)-6-oxo-5,7-dihydro-1h-pyrrolo[2,3-f]benzimidazole-7-carboxylate Chemical compound N=1C=2C=C3C(C(=O)OC)C(=O)NC3=CC=2NC=1C1=CC=C(OS(C)(=O)=O)C=C1OC JHFHCNZDHHLPQG-UHFFFAOYSA-N 0.000 description 1
- YZTZIPYVNIBMPL-UHFFFAOYSA-N methyl 2-[4-(7,7-dimethyl-6-oxo-1,5-dihydropyrrolo[2,3-f]benzimidazol-2-yl)-3-methoxyphenoxy]acetate Chemical compound COC1=CC(OCC(=O)OC)=CC=C1C(NC1=C2)=NC1=CC1=C2NC(=O)C1(C)C YZTZIPYVNIBMPL-UHFFFAOYSA-N 0.000 description 1
- VZCVDTMSMPJURJ-UHFFFAOYSA-N methyl 2-[4-(methanesulfonamido)-2-methoxyphenyl]-6-oxo-5,7-dihydro-1h-pyrrolo[2,3-f]benzimidazole-7-carboxylate Chemical compound N=1C=2C=C3C(C(=O)OC)C(=O)NC3=CC=2NC=1C1=CC=C(NS(C)(=O)=O)C=C1OC VZCVDTMSMPJURJ-UHFFFAOYSA-N 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- JAZOSZIQIJNSNZ-UHFFFAOYSA-N n-[3-methoxy-4-(7-methyl-6-oxo-5,7-dihydro-1h-pyrrolo[2,3-f]benzimidazol-2-yl)phenyl]methanesulfonamide Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1C(NC1=C2)=NC1=CC1=C2C(C)C(=O)N1 JAZOSZIQIJNSNZ-UHFFFAOYSA-N 0.000 description 1
- FFLDOSMYULAOAY-UHFFFAOYSA-N n-[4-(7,7-diethyl-6-oxo-1,5-dihydropyrrolo[2,3-f]benzimidazol-2-yl)-3-methoxyphenyl]methanesulfonamide Chemical compound N1C=2C=C3C(CC)(CC)C(=O)NC3=CC=2N=C1C1=CC=C(NS(C)(=O)=O)C=C1OC FFLDOSMYULAOAY-UHFFFAOYSA-N 0.000 description 1
- HEIGEAJXEMYNCJ-UHFFFAOYSA-N n-[4-(7-ethyl-6-oxo-5,7-dihydro-1h-pyrrolo[2,3-f]benzimidazol-2-yl)-3-methoxyphenyl]acetamide Chemical compound N1C=2C=C3C(CC)C(=O)NC3=CC=2N=C1C1=CC=C(NC(C)=O)C=C1OC HEIGEAJXEMYNCJ-UHFFFAOYSA-N 0.000 description 1
- MFJCFXYDZHLLSF-UHFFFAOYSA-N n-butyl-4-(7,7-dimethyl-6-oxo-1,5-dihydropyrrolo[2,3-f]benzimidazol-2-yl)-3-methoxybenzenesulfonamide Chemical compound COC1=CC(S(=O)(=O)NCCCC)=CC=C1C(NC1=C2)=NC1=CC1=C2NC(=O)C1(C)C MFJCFXYDZHLLSF-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 230000009090 positive inotropic effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Steroid Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843445669 DE3445669A1 (de) | 1984-12-14 | 1984-12-14 | Neue pyrrolo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD242045A5 true DD242045A5 (de) | 1987-01-14 |
Family
ID=6252801
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD85284206A DD242045A5 (de) | 1984-12-14 | 1985-12-12 | Neue pyrolo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US4710510A (it) |
| EP (1) | EP0186010B1 (it) |
| JP (1) | JPS61158984A (it) |
| AT (1) | ATE49970T1 (it) |
| AU (1) | AU580822B2 (it) |
| CA (1) | CA1262908A (it) |
| CS (1) | CS276403B6 (it) |
| DD (1) | DD242045A5 (it) |
| DE (2) | DE3445669A1 (it) |
| DK (1) | DK579185A (it) |
| ES (1) | ES8702409A1 (it) |
| FI (1) | FI79318C (it) |
| GR (1) | GR852979B (it) |
| HU (1) | HU194241B (it) |
| SU (1) | SU1440348A3 (it) |
| ZA (1) | ZA859382B (it) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3501497A1 (de) * | 1985-01-18 | 1986-07-24 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue pyrrolo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel sowie zwischenprodukte |
| DE3531678A1 (de) * | 1985-09-05 | 1987-03-12 | Boehringer Mannheim Gmbh | Neue pyrrolo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3626664A1 (de) * | 1986-08-07 | 1988-02-11 | Boehringer Mannheim Gmbh | Tricyclische benzotriazole, verfahren zu ihrer herstellung sowie arzneimittel |
| DE3639466A1 (de) * | 1986-11-18 | 1988-05-19 | Thomae Gmbh Dr K | Neue pyrrolo-benzimidazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| DE3642315A1 (de) * | 1986-12-11 | 1988-06-23 | Boehringer Mannheim Gmbh | Neue pyrrolobenzimidazole, verfahren zu ihrer herstellung sowie arzneimittel |
| DE3701277A1 (de) * | 1987-01-17 | 1988-07-28 | Boehringer Mannheim Gmbh | Neue tricyclische benzimidazole, verfahren zu ihrer herstellung und verwendung als arzneimittel |
| DE3740985A1 (de) * | 1987-12-03 | 1989-06-15 | Boehringer Mannheim Gmbh | Verwendung linear anellierter tricyclen als hemmer der erythrozytenaggregation |
| EP0322746B1 (en) * | 1987-12-30 | 1996-05-29 | Orion Corporation Limited | Heterocyclic compounds |
| US4963677A (en) * | 1987-12-30 | 1990-10-16 | Orion Corporation Ltd. | Heterocyclic lactam compounds |
| DE3803775A1 (de) * | 1988-02-09 | 1989-08-17 | Boehringer Mannheim Gmbh | Neue substituierte lactame, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten |
| DE4027592A1 (de) * | 1990-08-31 | 1992-03-05 | Beiersdorf Ag | Neue pyrrolobenzimidazole, imidazobenzoxazinone und imidazochinolone, verfahren zu ihrer herstellung und ihre verwendung sowie die verbindungen enthaltende zubereitungen |
| US7186745B2 (en) * | 2001-03-06 | 2007-03-06 | Astrazeneca Ab | Indolone derivatives having vascular damaging activity |
| EP1377549A1 (en) * | 2001-03-12 | 2004-01-07 | Millennium Pharmaceuticals, Inc. | Functionalized heterocycles as modulators of chemokine receptor function and methods of use therefor |
| WO2005072681A2 (en) * | 2004-01-23 | 2005-08-11 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments of inflammatory and neurotic pain. |
| MX2015003330A (es) | 2012-09-13 | 2015-06-05 | Hoffmann La Roche | 2-oxo-2,3-dihidro-indoles para el tratamiento de trastornos del sistema nervioso central (cns). |
| MY187540A (en) | 2014-08-01 | 2021-09-28 | Nuevolution As | Compounds active towards bromodomains |
| GB201709456D0 (en) * | 2017-06-14 | 2017-07-26 | Ucb Biopharma Sprl | Therapeutic agents |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4234571A (en) * | 1979-06-11 | 1980-11-18 | Syntex (U.S.A.) Inc. | Nonapeptide and decapeptide derivatives of luteinizing hormone releasing hormone |
| EP0033612B1 (en) * | 1980-02-02 | 1984-04-11 | Beecham Group Plc | Pyrano derivatives, a process for their preparation and antihypertensive compositions containing them |
| FR2476644A1 (fr) * | 1980-02-21 | 1981-08-28 | Sarget Lab | Orthoarylydeneaminophenethylamine, leur preparation et leur utilisation therapeutique |
| DE3224512A1 (de) * | 1982-07-01 | 1984-01-05 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue imidazolderivate, ihre herstellung und diese verbindungen enthaltende arzneimittel |
| SU1068439A1 (ru) * | 1982-10-28 | 1984-01-23 | Новокузнецкий научно-исследовательский химико-фармацевтический институт | Производные имидазо(4,5- @ ) индолов |
| US4579865A (en) * | 1983-02-14 | 1986-04-01 | Usv Pharmaceutical Corp. | Benzofuranyl carbamates |
| US4548943A (en) * | 1984-05-11 | 1985-10-22 | E. I. Du Pont De Nemours And Company | Antiinflammatory, analgesic, or anti-primary dysmenorrheal arylmethylene- and arylmethylindenoimidazoles |
| PL144822B1 (en) * | 1984-05-12 | 1988-07-30 | Boehringer Mannheim Gmbh | Method of obtaining novel pyrolobenzimidazoles |
| DE3501497A1 (de) * | 1985-01-18 | 1986-07-24 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue pyrrolo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel sowie zwischenprodukte |
| DE3531678A1 (de) * | 1985-09-05 | 1987-03-12 | Boehringer Mannheim Gmbh | Neue pyrrolo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
-
1984
- 1984-12-14 DE DE19843445669 patent/DE3445669A1/de not_active Withdrawn
-
1985
- 1985-12-06 EP EP85115547A patent/EP0186010B1/de not_active Expired - Lifetime
- 1985-12-06 AT AT85115547T patent/ATE49970T1/de not_active IP Right Cessation
- 1985-12-06 DE DE8585115547T patent/DE3575725D1/de not_active Expired - Lifetime
- 1985-12-09 ZA ZA859382A patent/ZA859382B/xx unknown
- 1985-12-09 AU AU51006/85A patent/AU580822B2/en not_active Ceased
- 1985-12-10 ES ES549776A patent/ES8702409A1/es not_active Expired
- 1985-12-10 US US06/807,260 patent/US4710510A/en not_active Expired - Fee Related
- 1985-12-12 DD DD85284206A patent/DD242045A5/de not_active IP Right Cessation
- 1985-12-12 GR GR852979A patent/GR852979B/el unknown
- 1985-12-12 FI FI854926A patent/FI79318C/fi not_active IP Right Cessation
- 1985-12-12 CS CS859195A patent/CS276403B6/cs unknown
- 1985-12-13 CA CA000497668A patent/CA1262908A/en not_active Expired
- 1985-12-13 HU HU854775A patent/HU194241B/hu not_active IP Right Cessation
- 1985-12-13 SU SU853995762A patent/SU1440348A3/ru active
- 1985-12-13 JP JP60279391A patent/JPS61158984A/ja active Granted
- 1985-12-13 DK DK579185A patent/DK579185A/da not_active Application Discontinuation
-
1987
- 1987-10-01 US US07/103,895 patent/US4810801A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ATE49970T1 (de) | 1990-02-15 |
| HUT40436A (en) | 1986-12-28 |
| US4810801A (en) | 1989-03-07 |
| FI79318B (fi) | 1989-08-31 |
| AU5100685A (en) | 1986-06-19 |
| ES549776A0 (es) | 1987-01-16 |
| CS919585A3 (en) | 1992-01-15 |
| CS276403B6 (en) | 1992-05-13 |
| JPS61158984A (ja) | 1986-07-18 |
| EP0186010A1 (de) | 1986-07-02 |
| FI854926A0 (fi) | 1985-12-12 |
| ES8702409A1 (es) | 1987-01-16 |
| FI854926A (fi) | 1986-06-15 |
| DE3575725D1 (de) | 1990-03-08 |
| GR852979B (it) | 1986-04-08 |
| JPH0471914B2 (it) | 1992-11-16 |
| AU580822B2 (en) | 1989-02-02 |
| ZA859382B (en) | 1986-08-27 |
| DE3445669A1 (de) | 1986-06-19 |
| US4710510A (en) | 1987-12-01 |
| FI79318C (fi) | 1989-12-11 |
| DK579185A (da) | 1986-06-15 |
| EP0186010B1 (de) | 1990-01-31 |
| DK579185D0 (da) | 1985-12-13 |
| SU1440348A3 (ru) | 1988-11-23 |
| CA1262908A (en) | 1989-11-14 |
| HU194241B (en) | 1988-01-28 |
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| Date | Code | Title | Description |
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| ENJ | Ceased due to non-payment of renewal fee |