CA1042903A - Benzoxazole derivatives - Google Patents
Benzoxazole derivativesInfo
- Publication number
- CA1042903A CA1042903A CA211,959A CA211959A CA1042903A CA 1042903 A CA1042903 A CA 1042903A CA 211959 A CA211959 A CA 211959A CA 1042903 A CA1042903 A CA 1042903A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- hydrogen
- hydroxy
- group
- acid
- 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
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 239000002253 acid Substances 0.000 claims abstract description 29
- -1 hydroxy, amino Chemical group 0.000 claims abstract description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 150000002148 esters Chemical group 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
- 150000003839 salts Chemical group 0.000 claims abstract description 10
- 150000002825 nitriles Chemical group 0.000 claims abstract description 9
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical group C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000001408 amides Chemical group 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000004755 (C2-C7) acylamino group Chemical group 0.000 claims abstract description 6
- 125000002252 acyl group Chemical group 0.000 claims abstract description 6
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims abstract description 5
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 4
- 125000005059 halophenyl group Chemical group 0.000 claims 2
- 239000000543 intermediate Substances 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 4
- 230000000202 analgesic effect Effects 0.000 abstract description 2
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
- 230000001754 anti-pyretic effect Effects 0.000 abstract description 2
- 239000002221 antipyretic Substances 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 230000000875 corresponding effect Effects 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 5
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
- MQBAVJCSIXDBPU-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)-1,3-benzoxazol-5-yl]acetic acid Chemical compound N=1C2=CC(CC(=O)O)=CC=C2OC=1C1=CC=C(Cl)C=C1 MQBAVJCSIXDBPU-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- MFNCUSZVVLNGEE-UHFFFAOYSA-N 2-[2-(2,4-dichlorophenyl)-1,3-benzoxazol-5-yl]acetic acid Chemical compound N=1C2=CC(CC(=O)O)=CC=C2OC=1C1=CC=C(Cl)C=C1Cl MFNCUSZVVLNGEE-UHFFFAOYSA-N 0.000 description 2
- HZSAXLGLIKSEBO-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)-1,3-benzoxazol-6-yl]acetic acid Chemical compound O1C2=CC(CC(=O)O)=CC=C2N=C1C1=CC=C(Cl)C=C1 HZSAXLGLIKSEBO-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- WZFXACQCFYCFGZ-UHFFFAOYSA-N ethyl 2-[2-(4-chlorophenyl)-1,3-benzoxazol-5-yl]acetate Chemical compound N=1C2=CC(CC(=O)OCC)=CC=C2OC=1C1=CC=C(Cl)C=C1 WZFXACQCFYCFGZ-UHFFFAOYSA-N 0.000 description 2
- XYEOXYQEFJJSAC-UHFFFAOYSA-N ethyl 2-bromo-2-[2-(4-chlorophenyl)-1,3-benzoxazol-5-yl]acetate Chemical compound N=1C2=CC(C(Br)C(=O)OCC)=CC=C2OC=1C1=CC=C(Cl)C=C1 XYEOXYQEFJJSAC-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000002560 nitrile group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000005968 oxazolinyl group Chemical group 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 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 description 2
- DKSZLDSPXIWGFO-BLOJGBSASA-N (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;phosphoric acid;hydrate Chemical compound O.OP(O)(O)=O.OP(O)(O)=O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC DKSZLDSPXIWGFO-BLOJGBSASA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QFHJRGYAPLZITA-UHFFFAOYSA-N 2-(2-phenyl-1,3-benzoxazol-5-yl)acetic acid Chemical compound N=1C2=CC(CC(=O)O)=CC=C2OC=1C1=CC=CC=C1 QFHJRGYAPLZITA-UHFFFAOYSA-N 0.000 description 1
- AOZKIUFHHMUPGU-UHFFFAOYSA-N 2-(3-amino-4-hydroxyphenyl)acetic acid Chemical compound NC1=CC(CC(O)=O)=CC=C1O AOZKIUFHHMUPGU-UHFFFAOYSA-N 0.000 description 1
- RDBAHYHARLPLHU-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-methyl-1,3-benzoxazole Chemical compound O1C2=CC(C)=CC=C2N=C1C1=CC=C(Cl)C=C1 RDBAHYHARLPLHU-UHFFFAOYSA-N 0.000 description 1
- YSOZVGOCUBDJII-UHFFFAOYSA-N 2-[2-(2,4-dichlorophenyl)-1,3-benzoxazol-5-yl]-2-hydroxypropanoic acid Chemical compound N=1C2=CC(C(O)(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1Cl YSOZVGOCUBDJII-UHFFFAOYSA-N 0.000 description 1
- ZBQNAZZAEXQGAC-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)-1,3-benzoxazol-5-yl]-2-(methylamino)propanoic acid Chemical compound N=1C2=CC(C(C)(C(O)=O)NC)=CC=C2OC=1C1=CC=C(Cl)C=C1 ZBQNAZZAEXQGAC-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- CHXXGSLEPPTWQN-UHFFFAOYSA-N 2-hydroxy-2-(2-phenyl-1,3-benzoxazol-5-yl)acetic acid Chemical compound N=1C2=CC(C(C(O)=O)O)=CC=C2OC=1C1=CC=CC=C1 CHXXGSLEPPTWQN-UHFFFAOYSA-N 0.000 description 1
- XELFGIQIGCCLOP-UHFFFAOYSA-N 2-hydroxy-2-(2-phenyl-1,3-benzoxazol-5-yl)propanoic acid Chemical compound N=1C2=CC(C(O)(C(O)=O)C)=CC=C2OC=1C1=CC=CC=C1 XELFGIQIGCCLOP-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- FIISKTXZUZBTRC-UHFFFAOYSA-N 2-phenyl-1,3-benzoxazole Chemical class C1=CC=CC=C1C1=NC2=CC=CC=C2O1 FIISKTXZUZBTRC-UHFFFAOYSA-N 0.000 description 1
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- KOXXDWYFLYJXTB-UHFFFAOYSA-N ethyl 2-bromo-2-[2-(4-methylphenyl)-1,3-benzoxazol-5-yl]acetate Chemical compound N=1C2=CC(C(Br)C(=O)OCC)=CC=C2OC=1C1=CC=C(C)C=C1 KOXXDWYFLYJXTB-UHFFFAOYSA-N 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229960004667 ethyl cellulose Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- LWAZINYSEHMDBE-UHFFFAOYSA-N methyl 2-[2-(4-chlorophenyl)-1,3-benzoxazol-5-yl]-2-methoxyacetate Chemical compound N=1C2=CC(C(C(=O)OC)OC)=CC=C2OC=1C1=CC=C(Cl)C=C1 LWAZINYSEHMDBE-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000012184 mineral wax Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000007017 scission Effects 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
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000012730 sustained-release form Substances 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
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 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
- 238000011200 topical administration Methods 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000012178 vegetable wax Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB49258/73A GB1490067A (en) | 1973-10-23 | 1973-10-23 | Benzoxazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1042903A true CA1042903A (en) | 1978-11-21 |
Family
ID=10451717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA211,959A Expired CA1042903A (en) | 1973-10-23 | 1974-10-22 | Benzoxazole derivatives |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS5070361A (cs) |
| AR (2) | AR215117A1 (cs) |
| AT (1) | AT339900B (cs) |
| BE (1) | BE821349A (cs) |
| BG (1) | BG25993A3 (cs) |
| CA (1) | CA1042903A (cs) |
| CH (1) | CH601273A5 (cs) |
| CS (1) | CS188929B2 (cs) |
| DD (1) | DD114816A5 (cs) |
| DE (1) | DE2449990A1 (cs) |
| DK (1) | DK552874A (cs) |
| ES (1) | ES431300A1 (cs) |
| FR (1) | FR2248040B1 (cs) |
| GB (1) | GB1490067A (cs) |
| HU (1) | HU169883B (cs) |
| IE (1) | IE40077B1 (cs) |
| IL (1) | IL45890A (cs) |
| NL (1) | NL7413787A (cs) |
| PL (1) | PL95927B1 (cs) |
| SE (1) | SE7413236L (cs) |
| SU (1) | SU581865A3 (cs) |
| ZA (1) | ZA746694B (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5890534A (ja) * | 1981-11-25 | 1983-05-30 | Ono Pharmaceut Co Ltd | ２−アミノフエノ−ル誘導体、その製造方法およびその誘導体を有効成分として含有する治療剤 |
-
1973
- 1973-10-23 GB GB49258/73A patent/GB1490067A/en not_active Expired
-
1974
- 1974-10-21 IL IL45890A patent/IL45890A/en unknown
- 1974-10-21 BG BG028006A patent/BG25993A3/xx unknown
- 1974-10-21 SE SE7413236A patent/SE7413236L/xx unknown
- 1974-10-22 CS CS747228A patent/CS188929B2/cs unknown
- 1974-10-22 SU SU7402074144A patent/SU581865A3/ru active
- 1974-10-22 CH CH1414474A patent/CH601273A5/xx not_active IP Right Cessation
- 1974-10-22 AT AT849474A patent/AT339900B/de not_active IP Right Cessation
- 1974-10-22 BE BE6044792A patent/BE821349A/xx unknown
- 1974-10-22 IE IE2166/74A patent/IE40077B1/xx unknown
- 1974-10-22 HU HULI264A patent/HU169883B/hu unknown
- 1974-10-22 PL PL1974175031A patent/PL95927B1/pl unknown
- 1974-10-22 DE DE19742449990 patent/DE2449990A1/de not_active Withdrawn
- 1974-10-22 FR FR7435408A patent/FR2248040B1/fr not_active Expired
- 1974-10-22 CA CA211,959A patent/CA1042903A/en not_active Expired
- 1974-10-22 DK DK552874A patent/DK552874A/da not_active Application Discontinuation
- 1974-10-22 ZA ZA00746694A patent/ZA746694B/xx unknown
- 1974-10-22 NL NL7413787A patent/NL7413787A/xx not_active Application Discontinuation
- 1974-10-23 ES ES431300A patent/ES431300A1/es not_active Expired
- 1974-10-23 JP JP49122353A patent/JPS5070361A/ja active Pending
- 1974-10-23 DD DD181867A patent/DD114816A5/xx unknown
- 1974-10-23 AR AR156196A patent/AR215117A1/es active
-
1975
- 1975-01-01 AR AR259615A patent/AR207595A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| FR2248040B1 (cs) | 1978-07-21 |
| AT339900B (de) | 1977-11-10 |
| HU169883B (cs) | 1977-02-28 |
| ATA849474A (de) | 1977-03-15 |
| AR215117A1 (es) | 1979-09-14 |
| AU7454474A (en) | 1976-04-29 |
| IL45890A (en) | 1977-12-30 |
| DK552874A (cs) | 1975-06-16 |
| ES431300A1 (es) | 1976-10-16 |
| DE2449990A1 (de) | 1975-04-30 |
| IE40077B1 (en) | 1979-03-14 |
| GB1490067A (en) | 1977-10-26 |
| FR2248040A1 (cs) | 1975-05-16 |
| ZA746694B (en) | 1976-06-30 |
| CS188929B2 (en) | 1979-03-30 |
| CH601273A5 (cs) | 1978-06-30 |
| AR207595A1 (es) | 1976-10-15 |
| IE40077L (en) | 1975-04-23 |
| BG25993A3 (bg) | 1979-01-12 |
| IL45890A0 (en) | 1974-12-31 |
| PL95927B1 (pl) | 1977-11-30 |
| NL7413787A (nl) | 1975-04-25 |
| BE821349A (fr) | 1975-04-22 |
| JPS5070361A (cs) | 1975-06-11 |
| SU581865A3 (ru) | 1977-11-25 |
| SE7413236L (cs) | 1975-04-24 |
| DD114816A5 (cs) | 1975-08-20 |
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