NO831517L - Fremgangsmaate for fremstilling av benzotiazolforbindelser - Google Patents
Fremgangsmaate for fremstilling av benzotiazolforbindelserInfo
- Publication number
- NO831517L NO831517L NO831517A NO831517A NO831517L NO 831517 L NO831517 L NO 831517L NO 831517 A NO831517 A NO 831517A NO 831517 A NO831517 A NO 831517A NO 831517 L NO831517 L NO 831517L
- Authority
- NO
- Norway
- Prior art keywords
- triazino
- benzothiazole
- amino
- compound
- formula
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 113
- 238000000034 method Methods 0.000 title claims abstract description 29
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 6
- 125000002071 phenylalkoxy group Chemical group 0.000 claims abstract description 6
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- -1 benzyloxyphenyl Chemical group 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 230000010933 acylation Effects 0.000 claims description 4
- 238000005917 acylation reaction Methods 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- PCMWWWOZYVQEOJ-UHFFFAOYSA-N 8-methoxy-2-phenylimino-[1,3,5]triazino[2,1-b][1,3]benzothiazol-4-amine Chemical compound C=1C(OC)=CC=C(N2C(=N)N=3)C=1SC2=NC=3NC1=CC=CC=C1 PCMWWWOZYVQEOJ-UHFFFAOYSA-N 0.000 claims description 3
- MGSUAUVCDPKWRX-UHFFFAOYSA-N 8-methoxy-4-methylimino-[1,3,5]triazino[2,1-b][1,3]benzothiazol-2-amine Chemical compound NC1=NC(=NC)N2C3=CC=C(OC)C=C3SC2=N1 MGSUAUVCDPKWRX-UHFFFAOYSA-N 0.000 claims description 3
- XNTOZBMKBYPUBH-UHFFFAOYSA-N 8-methoxy-4-phenylimino-[1,3,5]triazino[2,1-b][1,3]benzothiazol-2-amine Chemical compound C=1C(OC)=CC=C(N23)C=1SC3=NC(N)=NC2=NC1=CC=CC=C1 XNTOZBMKBYPUBH-UHFFFAOYSA-N 0.000 claims description 3
- IMMDAZOIWSLUOK-UHFFFAOYSA-N 8-methoxy-n-phenyl-4-phenylimino-[1,3,5]triazino[2,1-b][1,3]benzothiazol-2-amine Chemical compound C=1C(OC)=CC=C(N2C(=NC=3C=CC=CC=3)N=3)C=1SC2=NC=3NC1=CC=CC=C1 IMMDAZOIWSLUOK-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000003776 cleavage reaction Methods 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 230000007017 scission Effects 0.000 claims description 3
- VQEMLZKWBBKWBW-UHFFFAOYSA-N 4-cyclohexylimino-8-methoxy-[1,3,5]triazino[2,1-b][1,3]benzothiazol-2-amine Chemical compound C=1C(OC)=CC=C(N23)C=1SC3=NC(N)=NC2=NC1CCCCC1 VQEMLZKWBBKWBW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
- VUVIHJNCAJWTSA-UHFFFAOYSA-N n-(4-anilino-8-methoxy-[1,3,5]triazino[2,1-b][1,3]benzothiazol-2-ylidene)acetamide Chemical compound C=1C(OC)=CC=C(N23)C=1SC3=NC(NC(C)=O)=NC2=NC1=CC=CC=C1 VUVIHJNCAJWTSA-UHFFFAOYSA-N 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- SHIBOJMAXWSODF-UHFFFAOYSA-N 10-imino-8-methoxy-4-(4-methoxyphenyl)-4H-[1,3,5]triazino[2,1-b][1,3]benzothiazol-2-amine Chemical compound NC=1N=C2S(C3=C(N2C(N=1)C1=CC=C(C=C1)OC)C=CC(=C3)OC)=N SHIBOJMAXWSODF-UHFFFAOYSA-N 0.000 claims 1
- MLJNEGPZYMTAEB-UHFFFAOYSA-N 2-amino-4-phenylimino-[1,3,5]triazino[2,1-b][1,3]benzothiazol-8-ol Chemical compound N1=C(N)N=C2SC3=CC(O)=CC=C3N2C1=NC1=CC=CC=C1 MLJNEGPZYMTAEB-UHFFFAOYSA-N 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- UJOVFVWADYJIOX-UHFFFAOYSA-N 4-(2,6-dichlorophenyl)imino-8-methoxy-[1,3,5]triazino[2,1-b][1,3]benzothiazol-2-amine Chemical compound C=1C(OC)=CC=C(N23)C=1SC3=NC(N)=NC2=NC1=C(Cl)C=CC=C1Cl UJOVFVWADYJIOX-UHFFFAOYSA-N 0.000 claims 1
- BSOZFZTXLYBNBD-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)imino-8-methoxy-[1,3,5]triazino[2,1-b][1,3]benzothiazol-2-amine Chemical compound C=1C(OC)=CC=C(N23)C=1SC3=NC(N)=NC2=NC1=CC=C(Cl)C(Cl)=C1 BSOZFZTXLYBNBD-UHFFFAOYSA-N 0.000 claims 1
- PHZANCAEUMFALN-UHFFFAOYSA-N 4-(4-chlorophenyl)imino-8-methoxy-[1,3,5]triazino[2,1-b][1,3]benzothiazol-2-amine Chemical compound C=1C(OC)=CC=C(N23)C=1SC3=NC(N)=NC2=NC1=CC=C(Cl)C=C1 PHZANCAEUMFALN-UHFFFAOYSA-N 0.000 claims 1
- LVQYCPNUXDAELN-UHFFFAOYSA-N 4-[(2-amino-8-methoxy-[1,3,5]triazino[2,1-b][1,3]benzothiazol-4-ylidene)amino]benzoic acid Chemical compound COC1=CC=C2N3C(SC2=C1)=NC(N)=NC3=NC1=CC=C(C=C1)C(O)=O LVQYCPNUXDAELN-UHFFFAOYSA-N 0.000 claims 1
- XJMVAHITRKWIPJ-UHFFFAOYSA-N 4-[4-(dimethylamino)phenyl]imino-8-methoxy-[1,3,5]triazino[2,1-b][1,3]benzothiazol-2-amine Chemical compound C=1C(OC)=CC=C(N23)C=1SC3=NC(N)=NC2=NC1=CC=C(N(C)C)C=C1 XJMVAHITRKWIPJ-UHFFFAOYSA-N 0.000 claims 1
- GRMMOVVXSZWFOJ-UHFFFAOYSA-N 4-[4-[2-(diethylamino)ethoxy]phenyl]imino-8-methoxy-[1,3,5]triazino[2,1-b][1,3]benzothiazol-2-amine Chemical compound C1=CC(OCCN(CC)CC)=CC=C1N=C1N2C3=CC=C(OC)C=C3SC2=NC(N)=N1 GRMMOVVXSZWFOJ-UHFFFAOYSA-N 0.000 claims 1
- YHVUNKRIJNUUQQ-UHFFFAOYSA-N 4-benzylimino-8-methoxy-[1,3,5]triazino[2,1-b][1,3]benzothiazol-2-amine Chemical compound C=1C(OC)=CC=C(N23)C=1SC3=NC(N)=NC2=NCC1=CC=CC=C1 YHVUNKRIJNUUQQ-UHFFFAOYSA-N 0.000 claims 1
- MDGACZNIUWOYJT-UHFFFAOYSA-N 4-n-phenyl-[1,3,5]triazino[1,2-a]benzimidazole-2,4-diamine Chemical compound N1=C(N)N=C2NC3=CC=CC=C3N2C1=NC1=CC=CC=C1 MDGACZNIUWOYJT-UHFFFAOYSA-N 0.000 claims 1
- OBVZZSMBEUGPCC-UHFFFAOYSA-N 4-phenylimino-8-propan-2-yloxy-[1,3,5]triazino[2,1-b][1,3]benzothiazol-2-amine Chemical compound C=1C(OC(C)C)=CC=C(N23)C=1SC3=NC(N)=NC2=NC1=CC=CC=C1 OBVZZSMBEUGPCC-UHFFFAOYSA-N 0.000 claims 1
- RNMGGUBWJPTGAZ-UHFFFAOYSA-N 4-phenylimino-[1,3,5]triazino[2,1-b][1,3]benzothiazol-2-amine Chemical compound N1=C(N)N=C2SC3=CC=CC=C3N2C1=NC1=CC=CC=C1 RNMGGUBWJPTGAZ-UHFFFAOYSA-N 0.000 claims 1
- BTFDZWOPAJDRNO-UHFFFAOYSA-N 4-phenylimino-[1,3,5]triazino[2,1-b][1,3]benzoxazol-2-amine Chemical compound N1=C(N)N=C2OC3=CC=CC=C3N2C1=NC1=CC=CC=C1 BTFDZWOPAJDRNO-UHFFFAOYSA-N 0.000 claims 1
- ZJBLQYMELNPSLF-UHFFFAOYSA-N 4-tert-butylimino-8-methoxy-[1,3,5]triazino[2,1-b][1,3]benzothiazol-2-amine Chemical compound NC1=NC(=NC(C)(C)C)N2C3=CC=C(OC)C=C3SC2=N1 ZJBLQYMELNPSLF-UHFFFAOYSA-N 0.000 claims 1
- OVZUUBCZWWJMHJ-UHFFFAOYSA-N 7,8-dimethyl-4-phenylimino-[1,3,5]triazino[2,1-b][1,3]benzothiazol-2-amine Chemical compound N12C=3C=C(C)C(C)=CC=3SC2=NC(N)=NC1=NC1=CC=CC=C1 OVZUUBCZWWJMHJ-UHFFFAOYSA-N 0.000 claims 1
- GYVUAEFCULMFNP-UHFFFAOYSA-N 8-chloro-4-phenylimino-[1,3,5]triazino[2,1-b][1,3]benzothiazol-2-amine Chemical compound N1=C(N)N=C2SC3=CC(Cl)=CC=C3N2C1=NC1=CC=CC=C1 GYVUAEFCULMFNP-UHFFFAOYSA-N 0.000 claims 1
- CYBMXOKNQXRQQG-UHFFFAOYSA-N 8-methoxy-4-(2-phenylmethoxyphenyl)imino-[1,3,5]triazino[2,1-b][1,3]benzothiazol-2-amine Chemical compound C=1C(OC)=CC=C(N23)C=1SC3=NC(N)=NC2=NC1=CC=CC=C1OCC1=CC=CC=C1 CYBMXOKNQXRQQG-UHFFFAOYSA-N 0.000 claims 1
- HGCGBIGIDLUCRI-UHFFFAOYSA-N 8-methoxy-4-(4-methylphenyl)imino-[1,3,5]triazino[2,1-b][1,3]benzothiazol-2-amine Chemical compound C=1C(OC)=CC=C(N23)C=1SC3=NC(N)=NC2=NC1=CC=C(C)C=C1 HGCGBIGIDLUCRI-UHFFFAOYSA-N 0.000 claims 1
- PPMILQMAHHIIMD-UHFFFAOYSA-N 8-methoxy-4-(4-nitrophenyl)imino-[1,3,5]triazino[2,1-b][1,3]benzothiazol-2-amine Chemical compound C=1C(OC)=CC=C(N23)C=1SC3=NC(N)=NC2=NC1=CC=C([N+]([O-])=O)C=C1 PPMILQMAHHIIMD-UHFFFAOYSA-N 0.000 claims 1
- FCDJBCLKLOVCFE-UHFFFAOYSA-N 8-methyl-4-phenylimino-[1,3,5]triazino[2,1-b][1,3]benzothiazol-2-amine Chemical compound C=1C(C)=CC=C(N23)C=1SC3=NC(N)=NC2=NC1=CC=CC=C1 FCDJBCLKLOVCFE-UHFFFAOYSA-N 0.000 claims 1
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- PRXAKGDDRKQSAF-UHFFFAOYSA-N ethyl 4-[(2-amino-8-methoxy-[1,3,5]triazino[2,1-b][1,3]benzothiazol-4-ylidene)amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N=C1N2C3=CC=C(OC)C=C3SC2=NC(N)=N1 PRXAKGDDRKQSAF-UHFFFAOYSA-N 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 29
- 239000003814 drug Substances 0.000 abstract 1
- 238000009472 formulation Methods 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 30
- 239000000047 product Substances 0.000 description 28
- 239000007787 solid Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- 238000001819 mass spectrum Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 239000013078 crystal Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 238000001953 recrystallisation Methods 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 159000000000 sodium salts Chemical class 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
- 229960002523 mercuric chloride Drugs 0.000 description 6
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 241000700198 Cavia Species 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000002674 ointment Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
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- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000000699 topical effect Effects 0.000 description 4
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- KZHGPDSVHSDCMX-UHFFFAOYSA-N 6-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=C2N=C(N)SC2=C1 KZHGPDSVHSDCMX-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
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical compound NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 description 3
- 239000000427 antigen Substances 0.000 description 3
- 102000036639 antigens Human genes 0.000 description 3
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- YQZXJDJUNGXIPX-UHFFFAOYSA-N 1-cyano-3-phenylthiourea Chemical compound N#CNC(=S)NC1=CC=CC=C1 YQZXJDJUNGXIPX-UHFFFAOYSA-N 0.000 description 2
- JQHGAVRMSKHICJ-UHFFFAOYSA-N 2-(6-methoxy-1,3-benzothiazol-2-yl)guanidine Chemical compound COC1=CC=C2N=C(NC(N)=N)SC2=C1 JQHGAVRMSKHICJ-UHFFFAOYSA-N 0.000 description 2
- HPLHJODTTNDXBP-UHFFFAOYSA-N 4-n-phenyl-[1,3,5]triazino[1,2-a]benzimidazole-2,4-diamine;hydrochloride Chemical compound Cl.N1=C(N)N=C2NC3=CC=CC=C3N2C1=NC1=CC=CC=C1 HPLHJODTTNDXBP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 206010070834 Sensitisation Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 238000011316 allogeneic transplantation Methods 0.000 description 2
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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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Transplantation (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Sorting Of Articles (AREA)
- Body Structure For Vehicles (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8212654 | 1982-04-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO831517L true NO831517L (no) | 1983-10-31 |
Family
ID=10530109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO831517A NO831517L (no) | 1982-04-30 | 1983-04-29 | Fremgangsmaate for fremstilling av benzotiazolforbindelser |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4499269A (de) |
| EP (1) | EP0093515B1 (de) |
| JP (1) | JPS58194889A (de) |
| AT (1) | ATE25087T1 (de) |
| AU (1) | AU552775B2 (de) |
| DE (1) | DE3369322D1 (de) |
| DK (1) | DK182183A (de) |
| FI (1) | FI831289L (de) |
| NO (1) | NO831517L (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003037346A1 (en) * | 2001-10-31 | 2003-05-08 | Cell Therapeutics, Inc. | 6-phenyl-n-phenyl-(1,3,5) -triazine-2,4-diamine derivatives and related compounds with lysophphosphatidic acid acyltransferase beta (lpaat-beta) inhibitory activity for use in the treatment of cancer |
| US7419984B2 (en) * | 2002-10-17 | 2008-09-02 | Cell Therapeutics, Inc. | Pyrimidines and uses thereof |
| US6875781B2 (en) * | 2003-04-04 | 2005-04-05 | Cell Therapeutics, Inc. | Pyridines and uses thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3309366A (en) * | 1963-04-05 | 1967-03-14 | Geigy Ag J R | Imidazole(1, 2)-s-triazines |
-
1983
- 1983-04-08 AT AT83301978T patent/ATE25087T1/de not_active IP Right Cessation
- 1983-04-08 EP EP83301978A patent/EP0093515B1/de not_active Expired
- 1983-04-08 DE DE8383301978T patent/DE3369322D1/de not_active Expired
- 1983-04-18 FI FI831289A patent/FI831289L/fi not_active Application Discontinuation
- 1983-04-20 US US06/486,795 patent/US4499269A/en not_active Expired - Fee Related
- 1983-04-25 DK DK182183A patent/DK182183A/da not_active Application Discontinuation
- 1983-04-26 AU AU13938/83A patent/AU552775B2/en not_active Ceased
- 1983-04-26 JP JP58072329A patent/JPS58194889A/ja active Pending
- 1983-04-29 NO NO831517A patent/NO831517L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0093515B1 (de) | 1987-01-21 |
| FI831289A0 (fi) | 1983-04-18 |
| JPS58194889A (ja) | 1983-11-12 |
| EP0093515A1 (de) | 1983-11-09 |
| DK182183A (da) | 1983-10-31 |
| AU552775B2 (en) | 1986-06-19 |
| US4499269A (en) | 1985-02-12 |
| DK182183D0 (da) | 1983-04-25 |
| DE3369322D1 (en) | 1987-02-26 |
| ATE25087T1 (de) | 1987-02-15 |
| FI831289L (fi) | 1983-10-31 |
| AU1393883A (en) | 1983-11-03 |
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