FI63577C - Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 3,4-dihydropyrimido(1,2-a)bentsimidatsol-2(1h)-on-derivat - Google Patents
Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 3,4-dihydropyrimido(1,2-a)bentsimidatsol-2(1h)-on-derivat Download PDFInfo
- Publication number
- FI63577C FI63577C FI773724A FI773724A FI63577C FI 63577 C FI63577 C FI 63577C FI 773724 A FI773724 A FI 773724A FI 773724 A FI773724 A FI 773724A FI 63577 C FI63577 C FI 63577C
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- FI
- Finland
- Prior art keywords
- formula
- mixture
- dihydropyrimido
- benzimidazol
- compound
- Prior art date
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- AXJLWOZOUQAJCH-UHFFFAOYSA-N 3-(2-amino-5-cyanobenzimidazol-1-yl)propanoic acid Chemical compound N#CC1=CC=C2N(CCC(O)=O)C(N)=NC2=C1 AXJLWOZOUQAJCH-UHFFFAOYSA-N 0.000 description 1
- AFSDRVUYYAKKAE-UHFFFAOYSA-N 3-(4-benzoyl-2-nitroanilino)propanoic acid Chemical compound C1=C([N+]([O-])=O)C(NCCC(=O)O)=CC=C1C(=O)C1=CC=CC=C1 AFSDRVUYYAKKAE-UHFFFAOYSA-N 0.000 description 1
- HOYFZPFXOIOCNQ-UHFFFAOYSA-N 3-(4-cyano-2-nitroanilino)propanoic acid Chemical compound OC(=O)CCNC1=CC=C(C#N)C=C1[N+]([O-])=O HOYFZPFXOIOCNQ-UHFFFAOYSA-N 0.000 description 1
- YJHHPOVQQUWTCH-UHFFFAOYSA-N 3-(5-acetyl-2-aminobenzimidazol-1-yl)propanoic acid Chemical compound CC(=O)C1=CC=C2N(CCC(O)=O)C(N)=NC2=C1 YJHHPOVQQUWTCH-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- UGQOAAAVARWPRF-UHFFFAOYSA-N 4,5-dimethyl-1h-benzimidazol-2-amine Chemical compound CC1=CC=C2N=C(N)NC2=C1C UGQOAAAVARWPRF-UHFFFAOYSA-N 0.000 description 1
- RIBRJYQGDNOFEF-UHFFFAOYSA-N 4,6-dimethyl-1h-benzimidazol-2-amine Chemical compound CC1=CC(C)=C2NC(N)=NC2=C1 RIBRJYQGDNOFEF-UHFFFAOYSA-N 0.000 description 1
- XBLPHYSLHRGMNW-UHFFFAOYSA-N 4-chloro-3-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC(C#N)=CC=C1Cl XBLPHYSLHRGMNW-UHFFFAOYSA-N 0.000 description 1
- HOFKXNBVTNUDSH-UHFFFAOYSA-N 4-chloro-5-methylbenzene-1,2-diamine Chemical compound CC1=CC(N)=C(N)C=C1Cl HOFKXNBVTNUDSH-UHFFFAOYSA-N 0.000 description 1
- GRWXTRRBUDFFIM-UHFFFAOYSA-N 4-methylsulfanylbenzene-1,2-diamine Chemical compound CSC1=CC=C(N)C(N)=C1 GRWXTRRBUDFFIM-UHFFFAOYSA-N 0.000 description 1
- HAADRTMPUSJNOI-UHFFFAOYSA-N 5,6-dichloro-1h-benzimidazol-2-amine Chemical compound ClC1=C(Cl)C=C2NC(N)=NC2=C1 HAADRTMPUSJNOI-UHFFFAOYSA-N 0.000 description 1
- YPFQISHSXCFZMU-UHFFFAOYSA-N 5,6-dimethyl-1h-benzimidazol-2-amine Chemical compound C1=C(C)C(C)=CC2=C1NC(N)=N2 YPFQISHSXCFZMU-UHFFFAOYSA-N 0.000 description 1
- RRJIGHUKYPLKIW-UHFFFAOYSA-N 5-chloro-6-methyl-1h-benzimidazol-2-amine Chemical compound C1=C(Cl)C(C)=CC2=C1NC(N)=N2 RRJIGHUKYPLKIW-UHFFFAOYSA-N 0.000 description 1
- RHIPJPVWXDTEOX-UHFFFAOYSA-N 6-methylsulfanyl-1h-benzimidazol-2-amine Chemical compound CSC1=CC=C2N=C(N)NC2=C1 RHIPJPVWXDTEOX-UHFFFAOYSA-N 0.000 description 1
- CBXXFKUEWZXGAE-UHFFFAOYSA-N 7,8-dimethoxy-4,10-dihydro-3h-pyrimido[1,2-a]benzimidazol-2-one Chemical compound N1=C2NC(=O)CCN2C2=C1C=C(OC)C(OC)=C2 CBXXFKUEWZXGAE-UHFFFAOYSA-N 0.000 description 1
- ANZGAGYAWCRIOP-UHFFFAOYSA-N 7,8-dimethyl-4,10-dihydro-3h-pyrimido[1,2-a]benzimidazol-2-one Chemical compound N1=C2NC(=O)CCN2C2=C1C=C(C)C(C)=C2 ANZGAGYAWCRIOP-UHFFFAOYSA-N 0.000 description 1
- MHNNGFWZFMRICE-UHFFFAOYSA-N 8-(1-hydroxyethyl)-10h-pyrimido[1,2-a]benzimidazol-2-one Chemical compound O=C1C=CN2C3=CC=C(C(O)C)C=C3NC2=N1 MHNNGFWZFMRICE-UHFFFAOYSA-N 0.000 description 1
- GJYVNFASHFTWEU-UHFFFAOYSA-N 8-acetyl-4,10-dihydro-3h-pyrimido[1,2-a]benzimidazol-2-one Chemical class C1CC(=O)NC2=NC3=CC(C(=O)C)=CC=C3N21 GJYVNFASHFTWEU-UHFFFAOYSA-N 0.000 description 1
- YBPAGIDHPNXNDD-UHFFFAOYSA-N 8-methylsulfanyl-4,10-dihydro-3h-pyrimido[1,2-a]benzimidazol-2-one Chemical compound C1CC(=O)NC2=NC3=CC(SC)=CC=C3N21 YBPAGIDHPNXNDD-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- SRCBPDWALPBSMM-UHFFFAOYSA-N C(C)(=O)C1=CC2=C(N(C(=N2)N)CCC#N)C=C1.C(C)(=O)C1=CC2=C(N3C(=N2)NC(CC3)=O)C=C1 Chemical compound C(C)(=O)C1=CC2=C(N(C(=N2)N)CCC#N)C=C1.C(C)(=O)C1=CC2=C(N3C(=N2)NC(CC3)=O)C=C1 SRCBPDWALPBSMM-UHFFFAOYSA-N 0.000 description 1
- NUOCKWRABJBCSY-UHFFFAOYSA-N C(C=C)(=O)OC.N1C(NC2=C1C=CC=C2)=O Chemical compound C(C=C)(=O)OC.N1C(NC2=C1C=CC=C2)=O NUOCKWRABJBCSY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 206010010356 Congenital anomaly Diseases 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 229940127218 antiplatelet drug Drugs 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 238000005574 benzylation reaction Methods 0.000 description 1
- 229940000635 beta-alanine Drugs 0.000 description 1
- AGSPXMVUFBBBMO-UHFFFAOYSA-N beta-aminopropionitrile Chemical compound NCCC#N AGSPXMVUFBBBMO-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect 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
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000002680 cardiopulmonary resuscitation Methods 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229940102213 injectable suspension Drugs 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 239000002032 methanolic fraction Substances 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- LNDNYPUTPRJGSQ-UHFFFAOYSA-N methyl 3-(2-amino-5-benzoylbenzimidazol-1-yl)propanoate Chemical compound C=1C=C2N(CCC(=O)OC)C(N)=NC2=CC=1C(=O)C1=CC=CC=C1 LNDNYPUTPRJGSQ-UHFFFAOYSA-N 0.000 description 1
- DDUOVZQJFWRKOV-UHFFFAOYSA-N methyl 3-(2-amino-5-cyanobenzimidazol-1-yl)propanoate Chemical compound COC(CCN1C(=NC2=C1C=CC(=C2)C#N)N)=O DDUOVZQJFWRKOV-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 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
- 238000002156 mixing Methods 0.000 description 1
- YWANGSCDWBUSBK-UHFFFAOYSA-N n-(5-chloro-2-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1[N+]([O-])=O YWANGSCDWBUSBK-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 238000003260 vortexing Methods 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Hematology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5142676 | 1976-12-09 | ||
| GB51426/76A GB1585965A (en) | 1976-12-09 | 1976-12-09 | 3,4-dihydropyrimido (1,2 - )benzimidazol - 2(1h) - ones |
| GB3334177 | 1977-08-09 | ||
| GB3334177 | 1977-08-09 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI773724A7 FI773724A7 (fi) | 1978-06-10 |
| FI63577B FI63577B (fi) | 1983-03-31 |
| FI63577C true FI63577C (fi) | 1983-07-11 |
Family
ID=26261828
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI773724A FI63577C (fi) | 1976-12-09 | 1977-12-09 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 3,4-dihydropyrimido(1,2-a)bentsimidatsol-2(1h)-on-derivat |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4167569A (cs) |
| JP (1) | JPS5390296A (cs) |
| AT (1) | AT359068B (cs) |
| AU (1) | AU514427B2 (cs) |
| CA (1) | CA1086727A (cs) |
| CH (1) | CH633291A5 (cs) |
| CS (1) | CS199696B2 (cs) |
| DD (1) | DD133330A5 (cs) |
| DE (1) | DE2754930A1 (cs) |
| ES (1) | ES464862A1 (cs) |
| FI (1) | FI63577C (cs) |
| FR (1) | FR2373543A1 (cs) |
| GR (1) | GR65298B (cs) |
| HU (1) | HU176540B (cs) |
| IE (1) | IE45924B1 (cs) |
| IL (1) | IL53507A (cs) |
| IT (1) | IT1143729B (cs) |
| NL (1) | NL7713658A (cs) |
| NO (1) | NO774216L (cs) |
| NZ (1) | NZ185823A (cs) |
| PL (1) | PL107142B1 (cs) |
| SE (1) | SE435385B (cs) |
| SU (1) | SU843751A3 (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE51802B1 (en) * | 1979-12-03 | 1987-04-01 | Fujisawa Pharmaceutical Co | Quinazoline derivatives,processes for their preparation and pharmaceutical compositions containing them |
| CA1157858A (en) | 1979-12-03 | 1983-11-29 | Ikuo Ueda | Quinazoline derivatives |
| DE3208218A1 (de) * | 1982-03-06 | 1983-09-08 | Basf Ag, 6700 Ludwigshafen | Isoindolinfarbstoffe und deren verwendung |
| RU2394824C1 (ru) * | 2008-12-25 | 2010-07-20 | Государственное научное учреждение Северо-Кавказский зональный научно-исследовательский ветеринарный институт Российской академии сельскохозяйственных наук | ПРОИЗВОДНЫЕ ПИРИДО [1,2-a]БЕНЗИМИДАЗОЛА, ОБЛАДАЮЩИЕ АНТИБАКТЕРИАЛЬНЫМ ДЕЙСТВИЕМ, И СПОСОБ ИХ ПОЛУЧЕНИЯ |
| MY167785A (en) | 2012-06-27 | 2018-09-25 | 4Sg Ag | Bifluorodioxalane-amino-benzimidazole kinase inhibitors for the treatment of cancer, autoimmuneinflammation and cns disorders |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3468888A (en) * | 1967-04-11 | 1969-09-23 | Smithkline Corp | 2-substituted pyrimido(1,2-a) benzimidazoles |
| US3988340A (en) * | 1975-01-23 | 1976-10-26 | Bristol-Myers Company | 6-Alkoxymethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-ones and 7-alkoxymethyl-6-[H]-1,2,3,4-tetrahydropyrimido[2,1-b]quinazolin-2-ones |
| US4072679A (en) * | 1976-06-15 | 1978-02-07 | E. R. Squibb & Sons, Inc. | 1,4- AND 4,10-DIHYDRO-4-OXO-PYRIMIDO (1,2-A)-benzimidazole-3-carboxylic acids, esters and amides |
-
1977
- 1977-11-23 US US05/855,003 patent/US4167569A/en not_active Expired - Lifetime
- 1977-11-28 IE IE2408/77A patent/IE45924B1/en unknown
- 1977-11-29 CA CA291,976A patent/CA1086727A/en not_active Expired
- 1977-11-30 NZ NZ185823A patent/NZ185823A/xx unknown
- 1977-12-01 IL IL53507A patent/IL53507A/xx unknown
- 1977-12-01 AU AU31121/77A patent/AU514427B2/en not_active Expired
- 1977-12-05 HU HU77IE816A patent/HU176540B/hu unknown
- 1977-12-07 DD DD7700202450A patent/DD133330A5/xx unknown
- 1977-12-07 GR GR54931A patent/GR65298B/el unknown
- 1977-12-07 ES ES464862A patent/ES464862A1/es not_active Expired
- 1977-12-08 NO NO774216A patent/NO774216L/no unknown
- 1977-12-08 SE SE7713958A patent/SE435385B/sv unknown
- 1977-12-08 CH CH1507777A patent/CH633291A5/de not_active IP Right Cessation
- 1977-12-08 PL PL1977202753A patent/PL107142B1/pl unknown
- 1977-12-08 FR FR7737011A patent/FR2373543A1/fr active Granted
- 1977-12-09 NL NL7713658A patent/NL7713658A/xx not_active Application Discontinuation
- 1977-12-09 SU SU772552626A patent/SU843751A3/ru active
- 1977-12-09 AT AT883677A patent/AT359068B/de not_active IP Right Cessation
- 1977-12-09 DE DE19772754930 patent/DE2754930A1/de not_active Withdrawn
- 1977-12-09 IT IT30558/77A patent/IT1143729B/it active
- 1977-12-09 CS CS778270A patent/CS199696B2/cs unknown
- 1977-12-09 JP JP14866977A patent/JPS5390296A/ja active Pending
- 1977-12-09 FI FI773724A patent/FI63577C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA1086727A (en) | 1980-09-30 |
| FR2373543B1 (cs) | 1980-05-16 |
| JPS5390296A (en) | 1978-08-08 |
| SU843751A3 (ru) | 1981-06-30 |
| DD133330A5 (de) | 1978-12-27 |
| GR65298B (en) | 1980-08-01 |
| ATA883677A (de) | 1980-03-15 |
| CS199696B2 (en) | 1980-07-31 |
| IL53507A0 (en) | 1978-03-10 |
| PL202753A1 (pl) | 1978-10-09 |
| US4167569A (en) | 1979-09-11 |
| NL7713658A (nl) | 1978-06-13 |
| AU514427B2 (en) | 1981-02-12 |
| AT359068B (de) | 1980-10-27 |
| AU3112177A (en) | 1979-06-07 |
| NZ185823A (en) | 1980-08-26 |
| DE2754930A1 (de) | 1978-06-15 |
| PL107142B1 (pl) | 1980-01-31 |
| IE45924L (en) | 1978-06-09 |
| SE435385B (sv) | 1984-09-24 |
| HU176540B (en) | 1981-03-28 |
| IT1143729B (it) | 1986-10-22 |
| FR2373543A1 (fr) | 1978-07-07 |
| FI63577B (fi) | 1983-03-31 |
| IE45924B1 (en) | 1982-12-29 |
| SE7713958L (sv) | 1978-06-10 |
| IL53507A (en) | 1981-07-31 |
| CH633291A5 (de) | 1982-11-30 |
| ES464862A1 (es) | 1979-01-01 |
| NO774216L (no) | 1978-06-12 |
| FI773724A7 (fi) | 1978-06-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: IMPERIAL CHEMICAL INDUSTRIES LIMITED |