CA1158246A - Process of producing 2-phenylimidazo¬2,1-b| benzothiazole derivatives - Google Patents
Process of producing 2-phenylimidazo¬2,1-b| benzothiazole derivativesInfo
- Publication number
- CA1158246A CA1158246A CA000358790A CA358790A CA1158246A CA 1158246 A CA1158246 A CA 1158246A CA 000358790 A CA000358790 A CA 000358790A CA 358790 A CA358790 A CA 358790A CA 1158246 A CA1158246 A CA 1158246A
- Authority
- CA
- Canada
- Prior art keywords
- group
- benzothiazole
- imidazo
- hydrogen atom
- hydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 55
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title claims description 105
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- GNWRURVYHSXDSD-UHFFFAOYSA-N 2-phenylimidazo[2,1-b][1,3]benzothiazole Chemical class N1=C2SC3=CC=CC=C3N2C=C1C1=CC=CC=C1 GNWRURVYHSXDSD-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 112
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 52
- 125000003545 alkoxy group Chemical group 0.000 claims description 45
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 30
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
- RBQGKSWYSQGVDV-UHFFFAOYSA-N imidazo[2,1-b][1,3]benzothiazole Chemical compound C1=CC=C2N3C=CN=C3SC2=C1 RBQGKSWYSQGVDV-UHFFFAOYSA-N 0.000 claims description 28
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- -1 7-hydroxy-2-(p-methoxyphenyl)imidazo[2,1-b]benzothiazole Chemical compound 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000003277 amino group Chemical group 0.000 claims description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 17
- 125000004442 acylamino group Chemical group 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 14
- 125000004423 acyloxy group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 230000002152 alkylating effect Effects 0.000 claims description 8
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 7
- 230000003301 hydrolyzing effect Effects 0.000 claims description 7
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- DKEORPCGPBNOGO-UHFFFAOYSA-N 1,2-bis(4-chlorophenyl)imidazo[2,1-b][1,3]benzothiazole Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)N2C3=CC=CC=C3SC2=N1 DKEORPCGPBNOGO-UHFFFAOYSA-N 0.000 claims description 3
- GAOABCYCDYYUPR-UHFFFAOYSA-N 1-methyl-2-phenylimidazo[2,1-b][1,3]benzothiazole Chemical compound N1=C2SC3=CC=CC=C3N2C(C)=C1C1=CC=CC=C1 GAOABCYCDYYUPR-UHFFFAOYSA-N 0.000 claims description 3
- CPQINPMPUAUCJV-UHFFFAOYSA-N 2-imidazo[2,1-b][1,3]benzothiazol-2-ylphenol Chemical compound OC1=CC=CC=C1C1=CN2C3=CC=CC=C3SC2=N1 CPQINPMPUAUCJV-UHFFFAOYSA-N 0.000 claims description 3
- ZDWZHQCEMKRACL-UHFFFAOYSA-N 2-phenylimidazo[2,1-b][1,3]benzothiazol-6-ol Chemical compound C=1C(O)=CC=C(N2C=3)C=1SC2=NC=3C1=CC=CC=C1 ZDWZHQCEMKRACL-UHFFFAOYSA-N 0.000 claims description 3
- DPGKZDHSXINFBS-UHFFFAOYSA-N 3-imidazo[2,1-b][1,3]benzothiazol-2-ylphenol Chemical compound OC1=CC=CC(C=2N=C3N(C4=CC=CC=C4S3)C=2)=C1 DPGKZDHSXINFBS-UHFFFAOYSA-N 0.000 claims description 3
- DLPHWSNCEACAOY-UHFFFAOYSA-N 4-imidazo[2,1-b][1,3]benzothiazol-2-ylphenol Chemical compound C1=CC(O)=CC=C1C1=CN2C3=CC=CC=C3SC2=N1 DLPHWSNCEACAOY-UHFFFAOYSA-N 0.000 claims description 3
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 230000002140 halogenating effect Effects 0.000 claims description 3
- ULABPUCCHHYSTN-UHFFFAOYSA-N n-(3-imidazo[2,1-b][1,3]benzothiazol-2-ylphenyl)formamide Chemical compound O=CNC1=CC=CC(C=2N=C3N(C4=CC=CC=C4S3)C=2)=C1 ULABPUCCHHYSTN-UHFFFAOYSA-N 0.000 claims description 3
- 230000000802 nitrating effect Effects 0.000 claims description 3
- 125000002560 nitrile group Chemical group 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- YKDCWDJZZCLDPW-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-nitrosoimidazo[2,1-b][1,3]benzothiazole Chemical compound C1=CC(Cl)=CC=C1C1=C(N=O)N2C3=CC=CC=C3SC2=N1 YKDCWDJZZCLDPW-UHFFFAOYSA-N 0.000 claims description 2
- FCVPVNGXQLCEAW-UHFFFAOYSA-N methyl 3-imidazo[2,1-b][1,3]benzothiazol-2-ylbenzoate Chemical compound COC(=O)C1=CC=CC(C=2N=C3N(C4=CC=CC=C4S3)C=2)=C1 FCVPVNGXQLCEAW-UHFFFAOYSA-N 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- QNRFRGWVMABQKT-UHFFFAOYSA-N 2,6-dichloro-4-imidazo[2,1-b][1,3]benzothiazol-2-ylphenol Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1C1=CN2C3=CC=CC=C3SC2=N1 QNRFRGWVMABQKT-UHFFFAOYSA-N 0.000 claims 2
- IPBFEKWXKVTISK-UHFFFAOYSA-N 2-chloro-5-imidazo[2,1-b][1,3]benzothiazol-2-ylphenol Chemical compound C1=C(Cl)C(O)=CC(C=2N=C3N(C4=CC=CC=C4S3)C=2)=C1 IPBFEKWXKVTISK-UHFFFAOYSA-N 0.000 claims 2
- WUTCLFXGLBVBRQ-UHFFFAOYSA-N 2-(3-nitrophenyl)imidazo[2,1-b][1,3]benzothiazole Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C3N(C4=CC=CC=C4S3)C=2)=C1 WUTCLFXGLBVBRQ-UHFFFAOYSA-N 0.000 claims 1
- SWHIDPKIUAIOLB-UHFFFAOYSA-N 2-(4-hydroxyphenyl)imidazo[2,1-b][1,3]benzothiazol-6-ol Chemical compound C1=CC(O)=CC=C1C1=CN2C3=CC=C(O)C=C3SC2=N1 SWHIDPKIUAIOLB-UHFFFAOYSA-N 0.000 claims 1
- SJVSPBJRLIELAI-UHFFFAOYSA-N 4-imidazo[2,1-b][1,3]benzothiazol-2-ylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CN2C3=CC=CC=C3SC2=N1 SJVSPBJRLIELAI-UHFFFAOYSA-N 0.000 claims 1
- YYMOKOGEQBFACD-UHFFFAOYSA-N 5-imidazo[2,1-b][1,3]benzothiazol-2-yl-2-methylphenol Chemical compound C1=C(O)C(C)=CC=C1C1=CN2C3=CC=CC=C3SC2=N1 YYMOKOGEQBFACD-UHFFFAOYSA-N 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 8
- 239000000043 antiallergic agent Substances 0.000 abstract description 7
- 239000003435 antirheumatic agent Substances 0.000 abstract description 7
- 229940123907 Disease modifying antirheumatic drug Drugs 0.000 abstract description 6
- 230000003356 anti-rheumatic effect Effects 0.000 abstract description 6
- 230000004957 immunoregulator effect Effects 0.000 abstract description 4
- 229940124597 therapeutic agent Drugs 0.000 abstract description 4
- 208000023275 Autoimmune disease Diseases 0.000 abstract description 3
- 230000001088 anti-asthma Effects 0.000 abstract description 3
- 230000001093 anti-cancer Effects 0.000 abstract description 3
- 239000000924 antiasthmatic agent Substances 0.000 abstract description 3
- 238000002844 melting Methods 0.000 description 102
- 230000008018 melting Effects 0.000 description 102
- 238000000921 elemental analysis Methods 0.000 description 92
- 239000000203 mixture Substances 0.000 description 58
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 52
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 239000013078 crystal Substances 0.000 description 42
- 239000000243 solution Substances 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 230000002829 reductive effect Effects 0.000 description 33
- 239000011541 reaction mixture Substances 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 239000000460 chlorine Substances 0.000 description 25
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000001914 filtration Methods 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 229940093499 ethyl acetate Drugs 0.000 description 16
- 235000019439 ethyl acetate Nutrition 0.000 description 16
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 150000003431 steroids Chemical class 0.000 description 6
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
- 239000002168 alkylating agent Substances 0.000 description 5
- 229940100198 alkylating agent Drugs 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- HJRJRUMKQCMYDL-UHFFFAOYSA-N 1-chloro-2,4,6-trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(Cl)C([N+]([O-])=O)=C1 HJRJRUMKQCMYDL-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001350 alkyl halides Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229960000443 hydrochloric acid Drugs 0.000 description 4
- 235000011167 hydrochloric acid Nutrition 0.000 description 4
- 125000006501 nitrophenyl group Chemical group 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- 206010020751 Hypersensitivity Diseases 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000024932 T cell mediated immunity Effects 0.000 description 3
- 206010053613 Type IV hypersensitivity reaction Diseases 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- UVNXNSUKKOLFBM-UHFFFAOYSA-N imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=CSC2=NC=CN21 UVNXNSUKKOLFBM-UHFFFAOYSA-N 0.000 description 3
- 229960003390 magnesium sulfate Drugs 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- 229940086542 triethylamine Drugs 0.000 description 3
- 230000005951 type IV hypersensitivity Effects 0.000 description 3
- 208000027930 type IV hypersensitivity disease Diseases 0.000 description 3
- FSWUAVKROUPVFE-UHFFFAOYSA-N (3-imidazo[2,1-b][1,3]benzothiazol-2-ylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC(C=2N=C3N(C4=CC=CC=C4S3)C=2)=C1 FSWUAVKROUPVFE-UHFFFAOYSA-N 0.000 description 2
- ZSAFAOWYNUCHMX-UHFFFAOYSA-N (4-imidazo[2,1-b][1,3]benzothiazol-2-ylphenyl) acetate Chemical compound C1=CC(OC(=O)C)=CC=C1C1=CN2C3=CC=CC=C3SC2=N1 ZSAFAOWYNUCHMX-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- PMIPPNWVHPYERP-UHFFFAOYSA-N 2-(4-chlorophenyl)imidazo[2,1-b][1,3]benzothiazol-1-amine Chemical compound N1=C2SC3=CC=CC=C3N2C(N)=C1C1=CC=C(Cl)C=C1 PMIPPNWVHPYERP-UHFFFAOYSA-N 0.000 description 2
- POOOQPHNOURAEX-UHFFFAOYSA-N 2-(4-chlorophenyl)imidazo[2,1-b][1,3]benzothiazole Chemical compound C1=CC(Cl)=CC=C1C1=CN2C3=CC=CC=C3SC2=N1 POOOQPHNOURAEX-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- BBDALXOIBXSIKO-UHFFFAOYSA-N 6-methylsulfanyl-2-phenylimidazo[2,1-b][1,3]benzothiazole Chemical compound C=1C(SC)=CC=C(N2C=3)C=1SC2=NC=3C1=CC=CC=C1 BBDALXOIBXSIKO-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- 230000003266 anti-allergic effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- 230000003308 immunostimulating effect Effects 0.000 description 2
- 230000001506 immunosuppresive effect Effects 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
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- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- LURSUHVHQZXABT-UHFFFAOYSA-N methanesulfinyl chloride Chemical compound CS(Cl)=O LURSUHVHQZXABT-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- RMSLJAAYFCOBMH-UHFFFAOYSA-N methyl 2-hydroxy-5-imidazo[2,1-b][1,3]benzothiazol-2-ylbenzoate Chemical compound C1=C(O)C(C(=O)OC)=CC(C=2N=C3N(C4=CC=CC=C4S3)C=2)=C1 RMSLJAAYFCOBMH-UHFFFAOYSA-N 0.000 description 1
- MDBXJUJHNJYSCQ-UHFFFAOYSA-N methyl 5-imidazo[2,1-b][1,3]benzothiazol-2-yl-2-methylbenzenesulfinate Chemical compound C1=C(C)C(S(=O)OC)=CC(C=2N=C3N(C4=CC=CC=C4S3)C=2)=C1 MDBXJUJHNJYSCQ-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- QEUHDFNROWXUEI-UHFFFAOYSA-N n-(3-imidazo[2,1-b][1,3]benzothiazol-2-ylphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(C=2N=C3N(C4=CC=CC=C4S3)C=2)=C1 QEUHDFNROWXUEI-UHFFFAOYSA-N 0.000 description 1
- SEZFJHXUSOEBSH-UHFFFAOYSA-N n-(4-imidazo[2,1-b][1,3]benzothiazol-2-ylphenyl)acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CN2C3=CC=CC=C3SC2=N1 SEZFJHXUSOEBSH-UHFFFAOYSA-N 0.000 description 1
- DWKMMHAIALSICX-GZTJUZNOSA-N n-[(e)-benzylideneamino]-4-phenyl-1,3-thiazol-2-amine Chemical compound N=1C(C=2C=CC=CC=2)=CSC=1N\N=C\C1=CC=CC=C1 DWKMMHAIALSICX-GZTJUZNOSA-N 0.000 description 1
- NOVCAJILRHDVQR-UHFFFAOYSA-N n-methyl-2-phenylimidazo[2,1-b][1,3]benzothiazol-6-amine Chemical compound C=1C(NC)=CC=C(N2C=3)C=1SC2=NC=3C1=CC=CC=C1 NOVCAJILRHDVQR-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- DBSMLQTUDJVICQ-CJODITQLSA-N onametostat Chemical compound NC1=C2C=CN([C@@H]3C[C@H](CCC4=CC=C5C=C(Br)C(N)=NC5=C4)[C@@H](O)[C@H]3O)C2=NC=N1 DBSMLQTUDJVICQ-CJODITQLSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- AKEKKCGPLHMFCI-UHFFFAOYSA-L potassium sodium hydrogen carbonate Chemical compound [Na+].[K+].OC([O-])=O.OC([O-])=O AKEKKCGPLHMFCI-UHFFFAOYSA-L 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[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
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Substances ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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
- C07D277/82—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP106438/1979 | 1979-08-21 | ||
| JP10643879A JPS5630990A (en) | 1979-08-21 | 1979-08-21 | 2-phenylimidazo 2,1-b benzothiazole derivative and its preparation |
| JP145077/1979 | 1979-11-09 | ||
| JP14507779A JPS5668685A (en) | 1979-11-09 | 1979-11-09 | 2-phenylimidazo 2,1-b benzothiazole derivative and its preparation |
| JP148441/1979 | 1979-11-16 | ||
| JP14844179A JPS5671096A (en) | 1979-11-16 | 1979-11-16 | 2-phenylimidazo 2,1-b- benzothiazole derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1158246A true CA1158246A (en) | 1983-12-06 |
Family
ID=27310731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000358790A Expired CA1158246A (en) | 1979-08-21 | 1980-08-21 | Process of producing 2-phenylimidazo¬2,1-b| benzothiazole derivatives |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4497817A (enExample) |
| AT (1) | ATA425280A (enExample) |
| CA (1) | CA1158246A (enExample) |
| DE (1) | DE3030982A1 (enExample) |
| ES (1) | ES8106535A1 (enExample) |
| FR (1) | FR2463774A1 (enExample) |
| GB (1) | GB2056982B (enExample) |
| IT (1) | IT1166483B (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4464384A (en) * | 1981-12-23 | 1984-08-07 | Yamanouchi Pharmaceutical Co., Ltd. | 2-Phenylimidazo[2,1-b]benzothiazole compounds, salts thereof, process of producing them, and pharmaceutical compositions containing them |
| JP2726999B2 (ja) * | 1988-06-22 | 1998-03-11 | 日研化学株式会社 | イミダゾ［２，１−ｂ］ベンゾチアゾール誘導体及び該化合物を有効成分とする抗潰瘍剤 |
| IT1243362B (it) * | 1990-07-25 | 1994-06-10 | Pietro Monforte | Sintesi di attivita' anti-hiv di 1h, 3h-tiazolo 3,4-a benzimidazoli 1-sostituiti |
| WO1996028454A1 (en) * | 1995-03-13 | 1996-09-19 | Nikken Chemicals Co., Ltd. | Imidazothiazole compounds |
| WO1998006724A1 (en) * | 1996-08-09 | 1998-02-19 | Yamanouchi Pharmaceutical Co., Ltd. | Metabotropic glutamate receptor agonists |
| US6127387A (en) * | 1996-12-10 | 2000-10-03 | Thomas Jefferson University | Use of CD4-binding small molecules to inhibit immune responses |
| WO2000044364A2 (en) * | 1999-01-29 | 2000-08-03 | The Board Of Trustees Of The University Of Illinois | P53 inhibitors and their use for the treatment of cancer, hyperthermia, hypoxia, a burn, trauma to the central nervous system, a seizure, acute inflammation, tissue ageing, preservation of organs for transplant and preparation of a host for bone marrow transplant |
| DE19948434A1 (de) * | 1999-10-08 | 2001-06-07 | Gruenenthal Gmbh | Substanzbibliothek enthaltend bicyclische Imidazo-5-amine und/oder bicyclische Imidazo-3-amine |
| DE19948436B4 (de) * | 1999-10-08 | 2006-11-16 | Grünenthal GmbH | Bicyclische Imidazo-5-aminderivate |
| US6867299B2 (en) | 2000-02-24 | 2005-03-15 | Hoffmann-La Roche Inc. | Oxamide IMPDH inhibitors |
| US7601846B2 (en) * | 2001-06-26 | 2009-10-13 | The Regents Of The University Of California | Compounds having activity as inhibitors of apoptosis |
| DE10150172A1 (de) * | 2001-10-11 | 2003-04-30 | Morphochem Ag | Neue Verbindungen, die Protein Tyrosin Phosphatase 1B (PTP-1B) inhibieren |
| JP4991547B2 (ja) * | 2004-09-28 | 2012-08-01 | クアーク・ファーマスーティカルス、インコーポレイテッド | 脱毛症、急性腎不全および他の疾患の治療のためのオリゴリボヌクレオチドおよびその使用の方法 |
| US7825099B2 (en) * | 2006-01-20 | 2010-11-02 | Quark Pharmaceuticals, Inc. | Treatment or prevention of oto-pathologies by inhibition of pro-apoptotic genes |
| US7910566B2 (en) * | 2006-03-09 | 2011-03-22 | Quark Pharmaceuticals Inc. | Prevention and treatment of acute renal failure and other kidney diseases by inhibition of p53 by siRNA |
| TWI409267B (zh) * | 2006-03-17 | 2013-09-21 | Ambit Biosciences Corp | 治療疾病用之咪唑并噻唑化合物 |
| WO2009001359A2 (en) * | 2007-06-27 | 2008-12-31 | Quark Pharmaceuticals, Inc. | Compositions and methods for inhibiting expression of pro-apoptotic genes |
| KR101572701B1 (ko) * | 2007-09-19 | 2015-11-27 | 암비트 바이오사이언시즈 코포레이션 | Ｎ-(5-ｔｅｒｔ-부틸-이속사졸-3-일)-Ｎ'-[4-[7-(2-모르폴린-4-일-에톡시)이미다조[2,1-Ｂ][1,3]벤조티아졸-2-일]페닐]우레아를 포함하는 고체 형태, 그의 조성물 및 그의 용도 |
| EP2218464A1 (en) * | 2009-02-11 | 2010-08-18 | Technische Universität München | Compounds for non-invasive measurement of aggregates of amyloid peptides |
| CN107417705B (zh) * | 2017-07-24 | 2019-07-02 | 湘潭大学 | 咪唑并[2,1-b]苯并噻唑类化合物及其合成方法 |
| IL279972A (en) * | 2021-01-05 | 2022-08-01 | Anima Biotech Inc | Substances that function as modulators of cmyc-mrna translation and their uses in cancer treatment |
| EP4547671A1 (en) * | 2022-07-03 | 2025-05-07 | Anima Biotech Inc. | C-myc mrna translation modulators and uses thereof in the treatment of cancer |
| US12404283B2 (en) | 2022-07-03 | 2025-09-02 | Anima Biotech Inc. | c-MYC mRNA translation modulators and uses thereof in the treatment of cancer |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL129432C (enExample) * | 1964-02-29 | |||
| US4080339A (en) * | 1973-09-20 | 1978-03-21 | Pfizer Inc. | Imidazo[2,1-b]thiazole and thiazolo[3,2-a]benzimidazole quaternary salts as hypoglycemic agents and growth promotants |
| GB1541321A (en) * | 1976-03-10 | 1979-02-28 | Metabio | 2,3-dihydroimidazo(2,1-b)thiazole derivatives and process for their preparation |
| US4262004A (en) * | 1979-06-21 | 1981-04-14 | Janssen Pharmaceutica, N.V. | 2,3-Dihydro-imidazo[2,1-b]benzothiazole compositions to treat depressions |
-
1980
- 1980-08-13 FR FR8017896A patent/FR2463774A1/fr active Granted
- 1980-08-16 DE DE19803030982 patent/DE3030982A1/de not_active Withdrawn
- 1980-08-20 AT AT0425280A patent/ATA425280A/de not_active Application Discontinuation
- 1980-08-20 IT IT68303/80A patent/IT1166483B/it active
- 1980-08-20 ES ES494397A patent/ES8106535A1/es not_active Expired
- 1980-08-21 CA CA000358790A patent/CA1158246A/en not_active Expired
- 1980-08-21 GB GB8027243A patent/GB2056982B/en not_active Expired
-
1983
- 1983-04-26 US US06/487,357 patent/US4497817A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US4497817A (en) | 1985-02-05 |
| DE3030982A1 (de) | 1981-03-12 |
| IT8068303A0 (it) | 1980-08-20 |
| FR2463774B1 (enExample) | 1983-10-21 |
| GB2056982B (en) | 1983-11-16 |
| ATA425280A (de) | 1986-01-15 |
| IT1166483B (it) | 1987-05-06 |
| FR2463774A1 (fr) | 1981-02-27 |
| GB2056982A (en) | 1981-03-25 |
| ES494397A0 (es) | 1981-08-01 |
| ES8106535A1 (es) | 1981-08-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |