CS199696B2 - Method of producing derivatives of pyrimido/1,2-a/benzimidazole - Google Patents
Method of producing derivatives of pyrimido/1,2-a/benzimidazole Download PDFInfo
- Publication number
- CS199696B2 CS199696B2 CS778270A CS827077A CS199696B2 CS 199696 B2 CS199696 B2 CS 199696B2 CS 778270 A CS778270 A CS 778270A CS 827077 A CS827077 A CS 827077A CS 199696 B2 CS199696 B2 CS 199696B2
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- Czechoslovakia
- Prior art keywords
- hydrogen
- carbon atoms
- formula
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- 238000000034 method Methods 0.000 title claims abstract description 16
- JYZIHLWOWKMNNX-UHFFFAOYSA-N benzimidazole Chemical compound C1=C[CH]C2=NC=NC2=C1 JYZIHLWOWKMNNX-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 239000007858 starting material Substances 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- -1 atoms hydrogen Chemical class 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000003701 inert diluent Substances 0.000 claims description 2
- TZEMTMCOYZMUSN-UHFFFAOYSA-N 1H-benzimidazole 1H-pyrimidin-2-one Chemical compound O=C1N=CC=CN1.C1=CC=C2NC=NC2=C1 TZEMTMCOYZMUSN-UHFFFAOYSA-N 0.000 claims 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 1
- 238000001727 in vivo Methods 0.000 abstract description 7
- 238000000338 in vitro Methods 0.000 abstract description 3
- 238000011282 treatment Methods 0.000 abstract description 3
- 208000007536 Thrombosis Diseases 0.000 abstract description 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 2
- 238000011321 prophylaxis Methods 0.000 abstract description 2
- 210000001772 blood platelet Anatomy 0.000 abstract 2
- OLBDJDMNOKPXML-UHFFFAOYSA-N 3,4-dihydropyrimido[1,2-a]benzimidazole Chemical group C1=CC=C2N3CCC=NC3=NC2=C1 OLBDJDMNOKPXML-UHFFFAOYSA-N 0.000 abstract 1
- GJYVNFASHFTWEU-UHFFFAOYSA-N 8-acetyl-4,10-dihydro-3h-pyrimido[1,2-a]benzimidazol-2-one Chemical compound C1CC(=O)NC2=NC3=CC(C(=O)C)=CC=C3N21 GJYVNFASHFTWEU-UHFFFAOYSA-N 0.000 abstract 1
- 238000004220 aggregation Methods 0.000 abstract 1
- 230000002776 aggregation Effects 0.000 abstract 1
- 208000019553 vascular disease Diseases 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- 239000000203 mixture Substances 0.000 description 34
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 21
- 229910052799 carbon Inorganic materials 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical compound C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 8
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- 210000004369 blood Anatomy 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 206010043554 thrombocytopenia Diseases 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 description 3
- ASVPUUDJBLBNEH-UHFFFAOYSA-N 1-(2-amino-3h-benzimidazol-5-yl)ethanone Chemical compound CC(=O)C1=CC=C2N=C(N)NC2=C1 ASVPUUDJBLBNEH-UHFFFAOYSA-N 0.000 description 3
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 102000008186 Collagen Human genes 0.000 description 3
- 108010035532 Collagen Proteins 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229920001436 collagen Polymers 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- GPMHHSJZGVOEFS-UHFFFAOYSA-N 2-Amino-5-benzoylbenzimidazole Chemical compound C1=C2NC(N)=NC2=CC=C1C(=O)C1=CC=CC=C1 GPMHHSJZGVOEFS-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- PNMKRBOIMTZVLQ-UHFFFAOYSA-N 2-amino-3h-benzimidazole-5-carbonitrile Chemical compound C1=C(C#N)C=C2NC(N)=NC2=C1 PNMKRBOIMTZVLQ-UHFFFAOYSA-N 0.000 description 2
- RZBWGEXTRWUGBV-UHFFFAOYSA-N 3,6-dimethylbenzene-1,2-diamine Chemical class CC1=CC=C(C)C(N)=C1N RZBWGEXTRWUGBV-UHFFFAOYSA-N 0.000 description 2
- IFODSVOKJRKVAH-UHFFFAOYSA-N 5,6-di(propan-2-yloxy)-1h-benzimidazol-2-amine Chemical compound C1=C(OC(C)C)C(OC(C)C)=CC2=C1NC(N)=N2 IFODSVOKJRKVAH-UHFFFAOYSA-N 0.000 description 2
- OPGUZRRLMQSMAQ-UHFFFAOYSA-N 5-(4-methoxyphenyl)-1-phenylbenzimidazole Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N(C=N2)C=3C=CC=CC=3)C2=C1 OPGUZRRLMQSMAQ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000001177 diphosphate Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000000025 haemostatic effect Effects 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
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- 239000000126 substance Substances 0.000 description 2
- OPOULJSODSJJOS-UHFFFAOYSA-N (2-amino-3h-benzimidazol-5-yl)-(4-chlorophenyl)methanone Chemical compound C1=C2NC(N)=NC2=CC=C1C(=O)C1=CC=C(Cl)C=C1 OPOULJSODSJJOS-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- WZXFIDXRXIOGTR-UHFFFAOYSA-N 1,3-benzodioxole-4,5-diamine Chemical compound NC1=CC=C2OCOC2=C1N WZXFIDXRXIOGTR-UHFFFAOYSA-N 0.000 description 1
- ZCFSWYZFGJAUKK-UHFFFAOYSA-N 1,4-dimethyl-2,3-dinitrobenzene Chemical class CC1=CC=C(C)C([N+]([O-])=O)=C1[N+]([O-])=O ZCFSWYZFGJAUKK-UHFFFAOYSA-N 0.000 description 1
- YHDWKSALBRHRCQ-UHFFFAOYSA-N 1-(2-amino-3h-benzimidazol-5-yl)butan-1-one Chemical compound CCCC(=O)C1=CC=C2N=C(N)NC2=C1 YHDWKSALBRHRCQ-UHFFFAOYSA-N 0.000 description 1
- VEIXVSPCPGWULB-UHFFFAOYSA-N 1-(4-amino-3-nitrophenyl)ethanone Chemical compound CC(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 VEIXVSPCPGWULB-UHFFFAOYSA-N 0.000 description 1
- DSPHFASHOJAOKN-UHFFFAOYSA-N 1-[(7-oxobenzo[a]phenalen-2-yl)amino]anthracene-9,10-dione Chemical compound C1=CC2=CC(NC3=C4C(=O)C5=CC=CC=C5C(C4=CC=C3)=O)=CC(C=3C(=CC=CC=3)C3=O)=C2C3=C1 DSPHFASHOJAOKN-UHFFFAOYSA-N 0.000 description 1
- FFZKHULPLWYDQD-UHFFFAOYSA-N 12,14-dioxa-2,6,8-triazatetracyclo[7.7.0.02,7.011,15]hexadeca-1(16),7,9,11(15)-tetraen-5-one Chemical compound C1=C2N3CCC(=O)NC3=NC2=CC2=C1OCO2 FFZKHULPLWYDQD-UHFFFAOYSA-N 0.000 description 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
- JCRWHUMNIOSWNT-UHFFFAOYSA-N 2-oxo-4,10-dihydro-3h-pyrimido[1,2-a]benzimidazole-8-carbonitrile Chemical compound N#CC1=CC=C2N3CCC(=O)NC3=NC2=C1 JCRWHUMNIOSWNT-UHFFFAOYSA-N 0.000 description 1
- VWLLPPSBBHDXHK-UHFFFAOYSA-N 3,4-diaminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1N VWLLPPSBBHDXHK-UHFFFAOYSA-N 0.000 description 1
- SPVQXWWWBMKQGE-UHFFFAOYSA-N 4,10-dihydro-3h-pyrimido[1,2-a]benzimidazol-2-one Chemical class C1=CC=C2N3CCC(=O)NC3=NC2=C1 SPVQXWWWBMKQGE-UHFFFAOYSA-N 0.000 description 1
- FSCNFDUBSHSRET-UHFFFAOYSA-N 4,5-di(propan-2-yloxy)benzene-1,2-diamine Chemical compound CC(C)OC1=CC(N)=C(N)C=C1OC(C)C FSCNFDUBSHSRET-UHFFFAOYSA-N 0.000 description 1
- ZSAWWJYNDFERFN-UHFFFAOYSA-N 4,7-dimethyl-1h-benzimidazol-2-amine Chemical compound CC1=CC=C(C)C2=C1N=C(N)N2 ZSAWWJYNDFERFN-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 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
- WPMJALPQMIIHOE-UHFFFAOYSA-N 5-ethylsulfanyl-2-nitroaniline Chemical compound CCSC1=CC=C([N+]([O-])=O)C(N)=C1 WPMJALPQMIIHOE-UHFFFAOYSA-N 0.000 description 1
- WOIHSHXQQGYBGM-UHFFFAOYSA-N 5h-[1,3]dioxolo[4,5-f]benzimidazol-6-amine Chemical compound C1=C2NC(N)=NC2=CC2=C1OCO2 WOIHSHXQQGYBGM-UHFFFAOYSA-N 0.000 description 1
- CHFVQSSDSNUKHT-UHFFFAOYSA-N 6,7-dimethyl-4,10-dihydro-3h-pyrimido[1,2-a]benzimidazol-2-one Chemical compound N1C(=O)CCN2C3=C(C)C(C)=CC=C3N=C21 CHFVQSSDSNUKHT-UHFFFAOYSA-N 0.000 description 1
- WOGAYIVDKAOUQL-UHFFFAOYSA-N 7,8-dichloro-3,4-dihydro-1H-pyrimido[1,2-a]benzimidazol-2-one Chemical compound ClC=1C(=CC2=C(N3C(=N2)NC(CC3)=O)C=1)Cl WOGAYIVDKAOUQL-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
- IMQLCZMXGMSLQG-UHFFFAOYSA-N 7-acetyl-4,10-dihydro-3h-pyrimido[1,2-a]benzimidazol-2-one Chemical compound N1C(=O)CCN2C3=CC(C(=O)C)=CC=C3N=C21 IMQLCZMXGMSLQG-UHFFFAOYSA-N 0.000 description 1
- UISDXYAYVAQNOK-UHFFFAOYSA-N 8-(4-chlorobenzoyl)-4,10-dihydro-3h-pyrimido[1,2-a]benzimidazol-2-one Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(N2C(NC(=O)CC2)=N2)C2=C1 UISDXYAYVAQNOK-UHFFFAOYSA-N 0.000 description 1
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- HVTXXNGFDDGPBL-UHFFFAOYSA-N 8-benzoyl-4,10-dihydro-3h-pyrimido[1,2-a]benzimidazol-2-one Chemical compound C=1C=C2N3CCC(=O)NC3=NC2=CC=1C(=O)C1=CC=CC=C1 HVTXXNGFDDGPBL-UHFFFAOYSA-N 0.000 description 1
- PNCXFUNZJXQLCB-UHFFFAOYSA-N 8-butanoyl-4,10-dihydro-3h-pyrimido[1,2-a]benzimidazol-2-one Chemical compound C1CC(=O)NC2=NC3=CC(C(=O)CCC)=CC=C3N21 PNCXFUNZJXQLCB-UHFFFAOYSA-N 0.000 description 1
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- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 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
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 241000282412 Homo Species 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
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 206010033661 Pancytopenia Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229940030225 antihemorrhagics Drugs 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000011549 crystallization solution Substances 0.000 description 1
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 208000024389 cytopenia Diseases 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 210000002381 plasma Anatomy 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
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000012289 standard assay Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011273 tar residue Substances 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
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 208000021331 vascular occlusion disease Diseases 0.000 description 1
- 238000005303 weighing 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS791656A CS199697B2 (cs) | 1977-08-09 | 1979-03-13 | Způsob výroby derivátů pyrimido[ 1,2-a ] benzimidazolu |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB51426/76A GB1585965A (en) | 1976-12-09 | 1976-12-09 | 3,4-dihydropyrimido (1,2 - )benzimidazol - 2(1h) - ones |
| GB3334177 | 1977-08-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS199696B2 true CS199696B2 (en) | 1980-07-31 |
Family
ID=26261828
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS778270A CS199696B2 (en) | 1976-12-09 | 1977-12-09 | Method of producing derivatives of pyrimido/1,2-a/benzimidazole |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4167569A (de) |
| JP (1) | JPS5390296A (de) |
| AT (1) | AT359068B (de) |
| AU (1) | AU514427B2 (de) |
| CA (1) | CA1086727A (de) |
| CH (1) | CH633291A5 (de) |
| CS (1) | CS199696B2 (de) |
| DD (1) | DD133330A5 (de) |
| DE (1) | DE2754930A1 (de) |
| ES (1) | ES464862A1 (de) |
| FI (1) | FI63577C (de) |
| FR (1) | FR2373543A1 (de) |
| GR (1) | GR65298B (de) |
| HU (1) | HU176540B (de) |
| IE (1) | IE45924B1 (de) |
| IL (1) | IL53507A (de) |
| IT (1) | IT1143729B (de) |
| NL (1) | NL7713658A (de) |
| NO (1) | NO774216L (de) |
| NZ (1) | NZ185823A (de) |
| PL (1) | PL107142B1 (de) |
| SE (1) | SE435385B (de) |
| SU (1) | SU843751A3 (de) |
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 |
| EA029718B1 (ru) | 2012-06-27 | 2018-05-31 | 4-Эс-Си Дискавери Гмбх | Бифтордиоксалан-аминобензимидазольные ингибиторы киназы для лечения рака, аутоиммунного воспаления и нарушений цнс |
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 GR GR54931A patent/GR65298B/el unknown
- 1977-12-07 DD DD7700202450A patent/DD133330A5/de unknown
- 1977-12-07 ES ES464862A patent/ES464862A1/es not_active Expired
- 1977-12-08 FR FR7737011A patent/FR2373543A1/fr active Granted
- 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 NO NO774216A patent/NO774216L/no unknown
- 1977-12-08 SE SE7713958A patent/SE435385B/sv unknown
- 1977-12-09 DE DE19772754930 patent/DE2754930A1/de not_active Withdrawn
- 1977-12-09 AT AT883677A patent/AT359068B/de not_active IP Right Cessation
- 1977-12-09 IT IT30558/77A patent/IT1143729B/it active
- 1977-12-09 NL NL7713658A patent/NL7713658A/xx not_active Application Discontinuation
- 1977-12-09 CS CS778270A patent/CS199696B2/cs unknown
- 1977-12-09 JP JP14866977A patent/JPS5390296A/ja active Pending
- 1977-12-09 SU SU772552626A patent/SU843751A3/ru active
- 1977-12-09 FI FI773724A patent/FI63577C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7713658A (nl) | 1978-06-13 |
| PL202753A1 (pl) | 1978-10-09 |
| ES464862A1 (es) | 1979-01-01 |
| ATA883677A (de) | 1980-03-15 |
| FI63577C (fi) | 1983-07-11 |
| DE2754930A1 (de) | 1978-06-15 |
| AU3112177A (en) | 1979-06-07 |
| JPS5390296A (en) | 1978-08-08 |
| DD133330A5 (de) | 1978-12-27 |
| AT359068B (de) | 1980-10-27 |
| IE45924L (en) | 1978-06-09 |
| CA1086727A (en) | 1980-09-30 |
| PL107142B1 (pl) | 1980-01-31 |
| IL53507A (en) | 1981-07-31 |
| SE7713958L (sv) | 1978-06-10 |
| NO774216L (no) | 1978-06-12 |
| IE45924B1 (en) | 1982-12-29 |
| US4167569A (en) | 1979-09-11 |
| IT1143729B (it) | 1986-10-22 |
| FR2373543A1 (fr) | 1978-07-07 |
| AU514427B2 (en) | 1981-02-12 |
| FR2373543B1 (de) | 1980-05-16 |
| HU176540B (en) | 1981-03-28 |
| NZ185823A (en) | 1980-08-26 |
| FI773724A7 (fi) | 1978-06-10 |
| FI63577B (fi) | 1983-03-31 |
| SU843751A3 (ru) | 1981-06-30 |
| SE435385B (sv) | 1984-09-24 |
| GR65298B (en) | 1980-08-01 |
| CH633291A5 (de) | 1982-11-30 |
| IL53507A0 (en) | 1978-03-10 |
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