JPS6248672B2 - - Google Patents
Info
- Publication number
- JPS6248672B2 JPS6248672B2 JP54106438A JP10643879A JPS6248672B2 JP S6248672 B2 JPS6248672 B2 JP S6248672B2 JP 54106438 A JP54106438 A JP 54106438A JP 10643879 A JP10643879 A JP 10643879A JP S6248672 B2 JPS6248672 B2 JP S6248672B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- benzothiazole
- imidazo
- formula
- carboxy
- 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
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 29
- -1 2-imino-3-substituted-2,3-dihydrobenzothiazole Chemical class 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000004423 acyloxy group Chemical group 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000004442 acylamino group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 238000002844 melting Methods 0.000 description 44
- 230000008018 melting Effects 0.000 description 44
- 238000000921 elemental analysis Methods 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- 150000001875 compounds Chemical class 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 33
- 239000013078 crystal Substances 0.000 description 28
- 239000000243 solution Substances 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 229910052739 hydrogen Inorganic materials 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 229910052717 sulfur Inorganic materials 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- RBQGKSWYSQGVDV-UHFFFAOYSA-N imidazo[2,1-b][1,3]benzothiazole Chemical compound C1=CC=C2N3C=CN=C3SC2=C1 RBQGKSWYSQGVDV-UHFFFAOYSA-N 0.000 description 20
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 238000010992 reflux Methods 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000002994 raw material Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
- VEYHLDMLIAPPHS-UHFFFAOYSA-N 2-(3-chlorophenyl)imidazo[2,1-b][1,3]benzothiazole Chemical compound ClC1=CC=CC(C=2N=C3N(C4=CC=CC=C4S3)C=2)=C1 VEYHLDMLIAPPHS-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 206010020751 Hypersensitivity Diseases 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000043 antiallergic agent Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 150000003431 steroids Chemical class 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- HEQLGZFLSHFTNW-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)imidazo[2,1-b][1,3]benzothiazole Chemical compound ClC1=CC(Cl)=CC=C1C1=CN2C3=CC=CC=C3SC2=N1 HEQLGZFLSHFTNW-UHFFFAOYSA-N 0.000 description 5
- 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 description 5
- 230000007815 allergy Effects 0.000 description 5
- 239000003435 antirheumatic agent Substances 0.000 description 5
- 230000003111 delayed effect Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- SMDWSGDFYDQXPP-UHFFFAOYSA-N 1,2-diphenylimidazo[2,1-b][1,3]benzothiazole Chemical compound C1=CC=CC=C1C1=C(C=2C=CC=CC=2)N2C3=CC=CC=C3SC2=N1 SMDWSGDFYDQXPP-UHFFFAOYSA-N 0.000 description 4
- 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
- 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 description 4
- NVGWZZMLXUZQOQ-UHFFFAOYSA-N 2-naphthalen-2-ylimidazo[2,1-b][1,3]benzothiazole Chemical compound C1=CC=CC2=CC(C3=CN4C5=CC=CC=C5SC4=N3)=CC=C21 NVGWZZMLXUZQOQ-UHFFFAOYSA-N 0.000 description 4
- KMBLQOKKTHKUCJ-UHFFFAOYSA-N 3-(1-methylimidazo[2,1-b][1,3]benzothiazol-2-yl)phenol Chemical compound N1=C2SC3=CC=CC=C3N2C(C)=C1C1=CC=CC(O)=C1 KMBLQOKKTHKUCJ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 208000026935 allergic disease Diseases 0.000 description 4
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 4
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- UVNXNSUKKOLFBM-UHFFFAOYSA-N imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=CSC2=NC=CN21 UVNXNSUKKOLFBM-UHFFFAOYSA-N 0.000 description 4
- 230000006698 induction Effects 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 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
- KZEPILXRBJPAQW-UHFFFAOYSA-N 2-(4-iodophenyl)imidazo[2,1-b][1,3]benzothiazole Chemical compound C1=CC(I)=CC=C1C1=CN2C3=CC=CC=C3SC2=N1 KZEPILXRBJPAQW-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 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 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 230000007969 cellular immunity Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- 230000002519 immonomodulatory effect Effects 0.000 description 3
- 230000016784 immunoglobulin production Effects 0.000 description 3
- 230000001506 immunosuppresive effect Effects 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 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
- MJVJBAMSJWVOHE-UHFFFAOYSA-N 2-(2-chlorophenyl)imidazo[2,1-b][1,3]benzothiazole Chemical compound ClC1=CC=CC=C1C1=CN2C3=CC=CC=C3SC2=N1 MJVJBAMSJWVOHE-UHFFFAOYSA-N 0.000 description 2
- QHIPIZYEQJZFJN-UHFFFAOYSA-N 2-(2-methoxyphenyl)imidazo[2,1-b][1,3]benzothiazole Chemical compound COC1=CC=CC=C1C1=CN2C3=CC=CC=C3SC2=N1 QHIPIZYEQJZFJN-UHFFFAOYSA-N 0.000 description 2
- QFGAJWPGYQPRGF-UHFFFAOYSA-N 2-bromo-2,2-dichloro-1-phenylethanone Chemical compound ClC(Cl)(Br)C(=O)C1=CC=CC=C1 QFGAJWPGYQPRGF-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- YGCWPCVAVSIFLO-UHFFFAOYSA-N 2-phenyl-1,2-dihydroimidazo[2,1-b][1,3]benzothiazole Chemical compound N1=C2SC3=CC=CC=C3N2CC1C1=CC=CC=C1 YGCWPCVAVSIFLO-UHFFFAOYSA-N 0.000 description 2
- GNWRURVYHSXDSD-UHFFFAOYSA-N 2-phenylimidazo[2,1-b][1,3]benzothiazole Chemical compound N1=C2SC3=CC=CC=C3N2C=C1C1=CC=CC=C1 GNWRURVYHSXDSD-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 208000023275 Autoimmune disease Diseases 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 230000003266 anti-allergic effect Effects 0.000 description 2
- 230000003409 anti-rejection Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- IFVAVNPXTAWPRF-UHFFFAOYSA-N methyl 4-imidazo[2,1-b][1,3]benzothiazol-2-ylbenzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CN2C3=CC=CC=C3SC2=N1 IFVAVNPXTAWPRF-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 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 2
- 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 2
- 210000000056 organ Anatomy 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000002054 transplantation Methods 0.000 description 2
- 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 description 1
- UQYVXUYSPOIQIH-UHFFFAOYSA-N 1,3-benzothiazole dihydrochloride Chemical compound Cl.Cl.C1=CC=C2SC=NC2=C1 UQYVXUYSPOIQIH-UHFFFAOYSA-N 0.000 description 1
- SIHCWRGHADTIHW-UHFFFAOYSA-N 1-(3-chlorophenyl)-2-(2-imino-1,3-benzothiazol-3-yl)ethanone;hydrobromide Chemical compound Br.ClC1=CC=CC(C(=O)CN2C(SC3=CC=CC=C32)=N)=C1 SIHCWRGHADTIHW-UHFFFAOYSA-N 0.000 description 1
- FAYWKSQFWZAEHA-UHFFFAOYSA-N 1-nitro-2-(4-nitrophenyl)imidazo[2,1-b][1,3]benzothiazole Chemical compound N1=C2SC3=CC=CC=C3N2C([N+](=O)[O-])=C1C1=CC=C([N+]([O-])=O)C=C1 FAYWKSQFWZAEHA-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- NTJPIJOCTYDZGL-UHFFFAOYSA-N 2-(2-imino-1,3-benzothiazol-3-yl)-1-phenylethanol;hydrochloride Chemical compound Cl.C12=CC=CC=C2SC(=N)N1CC(O)C1=CC=CC=C1 NTJPIJOCTYDZGL-UHFFFAOYSA-N 0.000 description 1
- KDSFLBIFFQIOAP-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)imidazo[2,1-b][1,3]benzothiazole Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CN2C3=CC=CC=C3SC2=N1 KDSFLBIFFQIOAP-UHFFFAOYSA-N 0.000 description 1
- FIPPJMMBPCSCOV-UHFFFAOYSA-N 2-(3-methoxyphenyl)imidazo[2,1-b][1,3]benzothiazole Chemical compound COC1=CC=CC(C=2N=C3N(C4=CC=CC=C4S3)C=2)=C1 FIPPJMMBPCSCOV-UHFFFAOYSA-N 0.000 description 1
- TVRJGMHZQDLOPH-UHFFFAOYSA-N 2-(4-methoxyphenyl)imidazo[2,1-b][1,3]benzothiazole Chemical compound C1=CC(OC)=CC=C1C1=CN2C3=CC=CC=C3SC2=N1 TVRJGMHZQDLOPH-UHFFFAOYSA-N 0.000 description 1
- IHZHTMDQLGOMKV-UHFFFAOYSA-N 2-(4-nitrophenyl)imidazo[2,1-b][1,3]benzothiazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CN2C3=CC=CC=C3SC2=N1 IHZHTMDQLGOMKV-UHFFFAOYSA-N 0.000 description 1
- KNDAEDDIIQYRHY-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(piperazin-1-ylmethyl)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CN1CCNCC1 KNDAEDDIIQYRHY-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Immunology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10643879A JPS5630990A (en) | 1979-08-21 | 1979-08-21 | 2-phenylimidazo 2,1-b benzothiazole derivative and its preparation |
| FR8017896A FR2463774A1 (fr) | 1979-08-21 | 1980-08-13 | Derives du 2-phenylimidazo(2,1-b)benzothiazole |
| DE19803030982 DE3030982A1 (de) | 1979-08-21 | 1980-08-16 | 2-phenylimidazo(2,1-b)benzothiazolderivate |
| AT0425280A ATA425280A (de) | 1979-08-21 | 1980-08-20 | Verfahren zur herstellung von neuen 2-phenyl-imidazo(2.1-b)-benzothiazolderivaten |
| IT68303/80A IT1166483B (it) | 1979-08-21 | 1980-08-20 | Derivati del 2 fenilimidazo 2 1 b benzotiazolo aventi un effetto immunoregolatorio e procedimento per la loro preparazione |
| ES494397A ES8106535A1 (es) | 1979-08-21 | 1980-08-20 | Un procedimiento de produccion de un derivado de 2-fenilimi-dazo (2,1-b) benzotiazol |
| BE0/201803A BE884846A (fr) | 1979-08-21 | 1980-08-20 | Derives du 2-phenylimidazo (2,1-b)benzothiazole |
| GB8027243A GB2056982B (en) | 1979-08-21 | 1980-08-21 | 2 - phenylimidazo(2,1 - b)benzothiazole derivatives |
| CA000358790A CA1158246A (en) | 1979-08-21 | 1980-08-21 | Process of producing 2-phenylimidazo¬2,1-b| benzothiazole derivatives |
| US06/487,357 US4497817A (en) | 1979-08-21 | 1983-04-26 | 2-Phenylimidazo [2,1-b]benzothiazole derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10643879A JPS5630990A (en) | 1979-08-21 | 1979-08-21 | 2-phenylimidazo 2,1-b benzothiazole derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5630990A JPS5630990A (en) | 1981-03-28 |
| JPS6248672B2 true JPS6248672B2 (ko) | 1987-10-15 |
Family
ID=14433638
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10643879A Granted JPS5630990A (en) | 1979-08-21 | 1979-08-21 | 2-phenylimidazo 2,1-b benzothiazole derivative and its preparation |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5630990A (ko) |
| BE (1) | BE884846A (ko) |
-
1979
- 1979-08-21 JP JP10643879A patent/JPS5630990A/ja active Granted
-
1980
- 1980-08-20 BE BE0/201803A patent/BE884846A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5630990A (en) | 1981-03-28 |
| BE884846A (fr) | 1981-02-20 |
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