JPH0138791B2 - - Google Patents
Info
- Publication number
- JPH0138791B2 JPH0138791B2 JP55115610A JP11561080A JPH0138791B2 JP H0138791 B2 JPH0138791 B2 JP H0138791B2 JP 55115610 A JP55115610 A JP 55115610A JP 11561080 A JP11561080 A JP 11561080A JP H0138791 B2 JPH0138791 B2 JP H0138791B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- lower alkoxy
- compound
- lower alkyl
- 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
- 125000003545 alkoxy group Chemical group 0.000 claims description 46
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 25
- 125000004423 acyloxy group Chemical group 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- 125000003277 amino group Chemical group 0.000 claims description 19
- 125000004442 acylamino group Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 7
- 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 description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000002560 nitrile group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 3
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 3
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 88
- 238000002844 melting Methods 0.000 description 32
- 230000008018 melting Effects 0.000 description 32
- 238000000921 elemental analysis Methods 0.000 description 31
- 239000000243 solution Substances 0.000 description 24
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- 238000007796 conventional method Methods 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- -1 4-methylbenzoyl group Chemical group 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- RBQGKSWYSQGVDV-UHFFFAOYSA-N imidazo[2,1-b][1,3]benzothiazole Chemical compound C1=CC=C2N3C=CN=C3SC2=C1 RBQGKSWYSQGVDV-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 206010020751 Hypersensitivity Diseases 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000002168 alkylating agent Substances 0.000 description 6
- 229940100198 alkylating agent Drugs 0.000 description 6
- 239000000043 antiallergic agent Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 230000003301 hydrolyzing effect Effects 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 150000003431 steroids Chemical class 0.000 description 6
- 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
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 150000001350 alkyl halides Chemical class 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 208000026935 allergic disease Diseases 0.000 description 4
- 230000007815 allergy Effects 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 230000006698 induction Effects 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 238000002054 transplantation Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000007969 cellular immunity Effects 0.000 description 3
- 229910052801 chlorine Inorganic materials 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
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- LEHDTGMFYAQDQS-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-methylsulfanylimidazo[2,1-b][1,3]benzothiazole Chemical compound N1=C2SC3=CC=CC=C3N2C(SC)=C1C1=CC=C(Cl)C=C1 LEHDTGMFYAQDQS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-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 compound 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
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical group NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- 230000002862 amidating effect Effects 0.000 description 2
- 230000009435 amidation Effects 0.000 description 2
- 238000007112 amidation reaction Methods 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 230000003266 anti-allergic effect Effects 0.000 description 2
- 239000000924 antiasthmatic agent Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- UVNXNSUKKOLFBM-UHFFFAOYSA-N imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=CSC2=NC=CN21 UVNXNSUKKOLFBM-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 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 description 2
- SPZZBCAAFJGASA-UHFFFAOYSA-N n-(2-phenylimidazo[2,1-b][1,3]benzothiazol-6-yl)acetamide;hydrate Chemical compound O.C=1C(NC(=O)C)=CC=C(N2C=3)C=1SC2=NC=3C1=CC=CC=C1 SPZZBCAAFJGASA-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 210000000056 organ Anatomy 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- AYSQHRZFQUQXLY-UHFFFAOYSA-N (3-imidazo[2,1-b][1,3]benzothiazol-2-ylphenyl)methanol Chemical compound OCC1=CC=CC(C=2N=C3N(C4=CC=CC=C4S3)C=2)=C1 AYSQHRZFQUQXLY-UHFFFAOYSA-N 0.000 description 1
- QBGZIZIGMVPSSD-UHFFFAOYSA-N (7-methoxy-2-phenylimidazo[2,1-b][1,3]benzothiazol-6-yl) thiocyanate Chemical compound C1=C(SC#N)C(OC)=CC(N2C=3)=C1SC2=NC=3C1=CC=CC=C1 QBGZIZIGMVPSSD-UHFFFAOYSA-N 0.000 description 1
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- JIQMOQSQAVBFLO-UHFFFAOYSA-N 1-[3,5-bis(phenylmethoxy)phenyl]-2-bromoethanone Chemical compound C=1C(OCC=2C=CC=CC=2)=CC(C(=O)CBr)=CC=1OCC1=CC=CC=C1 JIQMOQSQAVBFLO-UHFFFAOYSA-N 0.000 description 1
- ARFABQJWRHKUGZ-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)imidazo[2,1-b][1,3]benzothiazole Chemical compound N1=C2SC3=CC=CC=C3N2C=C1C1=CC=C2OCOC2=C1 ARFABQJWRHKUGZ-UHFFFAOYSA-N 0.000 description 1
- XBCIFTUTZYYYTD-UHFFFAOYSA-N 2-(3,4-dimethylthiophen-2-yl)imidazo[2,1-b][1,3]benzothiazole Chemical compound CC=1C(=C(SC1)C=1N=C2SC3=C(N2C1)C=CC=C3)C XBCIFTUTZYYYTD-UHFFFAOYSA-N 0.000 description 1
- HUGQCCUAHWOOLT-UHFFFAOYSA-N 2-(3-hydroxyphenyl)imidazo[2,1-b][1,3]benzothiazol-6-ol Chemical compound OC1=CC=CC(C=2N=C3N(C4=CC=C(O)C=C4S3)C=2)=C1 HUGQCCUAHWOOLT-UHFFFAOYSA-N 0.000 description 1
- MDXWQCQHAPOKQU-UHFFFAOYSA-N 2-(4-chlorophenyl)imidazo[2,1-b][1,3]benzothiazol-6-ol Chemical compound C=1C(O)=CC=C(N2C=3)C=1SC2=NC=3C1=CC=C(Cl)C=C1 MDXWQCQHAPOKQU-UHFFFAOYSA-N 0.000 description 1
- QRXHSCCXJWKDSK-UHFFFAOYSA-N 2-(4-chlorophenyl)imidazo[2,1-b][1,3]benzothiazole-1-carbaldehyde Chemical compound C1=CC(Cl)=CC=C1C1=C(C=O)N2C3=CC=CC=C3SC2=N1 QRXHSCCXJWKDSK-UHFFFAOYSA-N 0.000 description 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 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
- VDSOIZJVNHZGRI-UHFFFAOYSA-N 2-(4-methyl-3-methylsulfinylphenyl)imidazo[2,1-b][1,3]benzothiazole Chemical compound C1=C(S(C)=O)C(C)=CC=C1C1=CN2C3=CC=CC=C3SC2=N1 VDSOIZJVNHZGRI-UHFFFAOYSA-N 0.000 description 1
- ZPAFDYRUNMYZFP-UHFFFAOYSA-N 2-(4-methyl-3-methylsulfonylphenyl)imidazo[2,1-b][1,3]benzothiazole Chemical compound C1=C(S(C)(=O)=O)C(C)=CC=C1C1=CN2C3=CC=CC=C3SC2=N1 ZPAFDYRUNMYZFP-UHFFFAOYSA-N 0.000 description 1
- QYGWYVCXALMIPR-UHFFFAOYSA-N 2-[3,5-bis(phenylmethoxy)phenyl]imidazo[2,1-b][1,3]benzothiazole Chemical compound C=1C=CC=CC=1COC(C=C(C=1)C=2N=C3N(C4=CC=CC=C4S3)C=2)=CC=1OCC1=CC=CC=C1 QYGWYVCXALMIPR-UHFFFAOYSA-N 0.000 description 1
- VLNVTNUTGNBNBY-UHFFFAOYSA-N 2-amino-1,3-benzothiazol-6-ol Chemical compound C1=C(O)C=C2SC(N)=NC2=C1 VLNVTNUTGNBNBY-UHFFFAOYSA-N 0.000 description 1
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 1
- XQJAHBHCLXUGEP-UHFFFAOYSA-N 2-bromo-1-(4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(=O)CBr)C=C1 XQJAHBHCLXUGEP-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 description 1
- KUFDZIJSJAUKNL-UHFFFAOYSA-N 2-phenylimidazo[2,1-b][1,3]benzothiazol-6-amine Chemical compound C=1C(N)=CC=C(N2C=3)C=1SC2=NC=3C1=CC=CC=C1 KUFDZIJSJAUKNL-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- XPNAUISEOHPRPH-UHFFFAOYSA-N 3-imidazo[2,1-b][1,3]benzothiazol-2-ylbenzamide Chemical compound NC(=O)C1=CC=CC(C=2N=C3N(C4=CC=CC=C4S3)C=2)=C1 XPNAUISEOHPRPH-UHFFFAOYSA-N 0.000 description 1
- RXYDGVPYBWRQHD-UHFFFAOYSA-N 3-imidazo[2,1-b][1,3]benzothiazol-2-ylbenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(C=2N=C3N(C4=CC=CC=C4S3)C=2)=C1 RXYDGVPYBWRQHD-UHFFFAOYSA-N 0.000 description 1
- HLCZXUUEOYGLAR-UHFFFAOYSA-N 3-imidazo[2,1-b][1,3]benzothiazol-2-ylbenzonitrile Chemical compound N#CC1=CC=CC(C=2N=C3N(C4=CC=CC=C4S3)C=2)=C1 HLCZXUUEOYGLAR-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010008909 Chronic Hepatitis Diseases 0.000 description 1
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- 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
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- 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
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- 239000011591 potassium Substances 0.000 description 1
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- 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
- 238000007363 ring formation reaction 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
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
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- 238000012360 testing method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55115610A JPS5740492A (en) | 1980-08-22 | 1980-08-22 | Novel 2-phenylimidazo 2,1-b benzothiazole derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55115610A JPS5740492A (en) | 1980-08-22 | 1980-08-22 | Novel 2-phenylimidazo 2,1-b benzothiazole derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5740492A JPS5740492A (en) | 1982-03-06 |
| JPH0138791B2 true JPH0138791B2 (da) | 1989-08-16 |
Family
ID=14666900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55115610A Granted JPS5740492A (en) | 1980-08-22 | 1980-08-22 | Novel 2-phenylimidazo 2,1-b benzothiazole derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5740492A (da) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI91859C (fi) * | 1987-06-17 | 1994-08-25 | Eisai Co Ltd | Analogiamenetelmä antiallergisena aineena aktiivisen bentsotiatsolijohdannaisen valmistamiseksi |
| 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 |
| CA2215197A1 (en) * | 1995-03-13 | 1996-09-19 | Shigeyuki Tasaka | Imidazothiazole compound |
| AU3783497A (en) * | 1996-08-09 | 1998-03-06 | Yamanouchi Pharmaceutical Co., Ltd. | Metabotropic glutamate receptor agonists |
| KR101549364B1 (ko) | 2006-03-17 | 2015-09-01 | 암비트 바이오사이언시즈 코포레이션 | 질환 치료용 이미다졸로티아졸 화합물 |
| ES2573292T3 (es) | 2007-09-19 | 2016-06-07 | Ambit Biosciences Corporation | Formas sólidas que comprenden N-(5-terc-butil-isoxazol-3-il)-N'-{4-[7-(2-morfolin-4-il-etoxi)imidazo[2,1-b][1,3]benzotiazol-2-il]fenil}urea, composiciones de las mismas y usos de las mismas |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6248672A (ja) * | 1985-06-18 | 1987-03-03 | ビオガル ジヨジセルジヤ−ル | チアゾリジンカルボン酸誘導体 |
| JPS6320237A (ja) * | 1986-07-11 | 1988-01-27 | Kubota Ltd | 車輌の油圧ポンプ駆動装置 |
| JPS6320236A (ja) * | 1986-07-11 | 1988-01-27 | Daihatsu Motor Co Ltd | ２輪・４輪駆動切換機構の制御装置 |
-
1980
- 1980-08-22 JP JP55115610A patent/JPS5740492A/ja active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6248672A (ja) * | 1985-06-18 | 1987-03-03 | ビオガル ジヨジセルジヤ−ル | チアゾリジンカルボン酸誘導体 |
| JPS6320237A (ja) * | 1986-07-11 | 1988-01-27 | Kubota Ltd | 車輌の油圧ポンプ駆動装置 |
| JPS6320236A (ja) * | 1986-07-11 | 1988-01-27 | Daihatsu Motor Co Ltd | ２輪・４輪駆動切換機構の制御装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5740492A (en) | 1982-03-06 |
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| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |