NO136712B - - Google Patents
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- Publication number
- NO136712B NO136712B NO3355/71A NO335571A NO136712B NO 136712 B NO136712 B NO 136712B NO 3355/71 A NO3355/71 A NO 3355/71A NO 335571 A NO335571 A NO 335571A NO 136712 B NO136712 B NO 136712B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- benzoxazol
- benzoxazole
- hydrogen
- mixture
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 28
- 150000001408 amides Chemical class 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 231100000252 nontoxic Toxicity 0.000 claims description 6
- 230000003000 nontoxic effect Effects 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- FRFQGGRLXTVFBG-UHFFFAOYSA-N 2-[4-(1,3-benzoxazol-2-yl)phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C1=NC2=CC=CC=C2O1 FRFQGGRLXTVFBG-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 239000002253 acid Substances 0.000 description 37
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
- 239000000203 mixture Substances 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- -1 ion salt Chemical class 0.000 description 20
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 14
- 238000003776 cleavage reaction Methods 0.000 description 13
- 230000007017 scission Effects 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000010828 elution Methods 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 235000019400 benzoyl peroxide Nutrition 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- AWCMNCDJXFWKTO-UHFFFAOYSA-N 2-(3-fluoro-4-methylphenyl)-1,3-benzoxazole Chemical compound C1=C(F)C(C)=CC=C1C1=NC2=CC=CC=C2O1 AWCMNCDJXFWKTO-UHFFFAOYSA-N 0.000 description 4
- ZAXLJGNKZIOEJN-UHFFFAOYSA-N 2-[4-(bromomethyl)-3-fluorophenyl]-1,3-benzoxazole Chemical compound C1=C(CBr)C(F)=CC(C=2OC3=CC=CC=C3N=2)=C1 ZAXLJGNKZIOEJN-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 230000001754 anti-pyretic effect Effects 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 description 4
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 3
- QEHVZLYSEMNBIJ-UHFFFAOYSA-N 2-(2-fluoro-4-methylphenyl)-1,3-benzoxazole Chemical compound FC1=CC(C)=CC=C1C1=NC2=CC=CC=C2O1 QEHVZLYSEMNBIJ-UHFFFAOYSA-N 0.000 description 3
- ADDCUSIRCGNNII-UHFFFAOYSA-N 2-[4-(1,3-benzoxazol-2-yl)-2-fluorophenyl]acetic acid Chemical compound C1=C(F)C(CC(=O)O)=CC=C1C1=NC2=CC=CC=C2O1 ADDCUSIRCGNNII-UHFFFAOYSA-N 0.000 description 3
- GGCPYCRPEWHCQT-UHFFFAOYSA-N 2-[4-(1,3-benzoxazol-2-yl)-2-fluorophenyl]acetonitrile Chemical compound C1=C(CC#N)C(F)=CC(C=2OC3=CC=CC=C3N=2)=C1 GGCPYCRPEWHCQT-UHFFFAOYSA-N 0.000 description 3
- RWXRIVQREANWBZ-UHFFFAOYSA-N 2-[4-(1,3-benzoxazol-2-yl)-3-fluorophenyl]acetic acid Chemical compound FC1=CC(CC(=O)O)=CC=C1C1=NC2=CC=CC=C2O1 RWXRIVQREANWBZ-UHFFFAOYSA-N 0.000 description 3
- SVSVOPWCUHQFAM-UHFFFAOYSA-N 2-fluoro-4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C(F)=C1 SVSVOPWCUHQFAM-UHFFFAOYSA-N 0.000 description 3
- HGYACDWHRDFSTI-UHFFFAOYSA-N 3-fluoro-n-(2-hydroxyphenyl)-4-methylbenzamide Chemical compound C1=C(F)C(C)=CC=C1C(=O)NC1=CC=CC=C1O HGYACDWHRDFSTI-UHFFFAOYSA-N 0.000 description 3
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
- 206010061218 Inflammation Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 description 3
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- UJUJTJBCXVEAGQ-UHFFFAOYSA-N ethyl 2-amino-4-ethylbenzoate Chemical compound CCOC(=O)C1=CC=C(CC)C=C1N UJUJTJBCXVEAGQ-UHFFFAOYSA-N 0.000 description 3
- XOTHHWKTZXUUGF-UHFFFAOYSA-N ethyl 4-ethyl-2-fluorobenzoate Chemical compound CCOC(=O)C1=CC=C(CC)C=C1F XOTHHWKTZXUUGF-UHFFFAOYSA-N 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- MLAJZRMDXUNKBQ-UHFFFAOYSA-N 1,3-benzoxazole;2-phenylacetic acid Chemical compound C1=CC=C2OC=NC2=C1.OC(=O)CC1=CC=CC=C1 MLAJZRMDXUNKBQ-UHFFFAOYSA-N 0.000 description 2
- 150000000183 1,3-benzoxazoles Chemical class 0.000 description 2
- ULLVHIYNHNLLTD-UHFFFAOYSA-N 2-(2-bicyclo[4.2.0]octa-1(6),2,4-trienyl)-1,3-benzoxazole Chemical compound O1C(=NC2=C1C=CC=C2)C2=C1C(CC1)=CC=C2 ULLVHIYNHNLLTD-UHFFFAOYSA-N 0.000 description 2
- PWDRABLQVUHYAE-UHFFFAOYSA-N 2-(4-ethylphenyl)-1,3-benzoxazole Chemical compound C1=CC(CC)=CC=C1C1=NC2=CC=CC=C2O1 PWDRABLQVUHYAE-UHFFFAOYSA-N 0.000 description 2
- HGVAGPYGRASSIW-UHFFFAOYSA-N 2-(8-bromo-2-bicyclo[4.2.0]octa-1(6),2,4-trienyl)-1,3-benzoxazole Chemical compound C1=CC=C2OC(C=3C=CC=C4CC(C=34)Br)=NC2=C1 HGVAGPYGRASSIW-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- FXLLPFZHBJEAAF-UHFFFAOYSA-N 2-[4-(1,3-benzoxazol-2-yl)-3-fluorophenyl]acetonitrile Chemical compound FC1=CC(CC#N)=CC=C1C1=NC2=CC=CC=C2O1 FXLLPFZHBJEAAF-UHFFFAOYSA-N 0.000 description 2
- SSNLLVDAIDMADK-UHFFFAOYSA-N 2-[4-(1,3-benzoxazol-2-yl)-3-fluorophenyl]propanenitrile Chemical compound FC1=CC(C(C#N)C)=CC=C1C1=NC2=CC=CC=C2O1 SSNLLVDAIDMADK-UHFFFAOYSA-N 0.000 description 2
- AOHYZOQLEUTIOK-UHFFFAOYSA-N 2-[4-(1,3-benzoxazol-2-yl)-3-fluorophenyl]propanoic acid Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=NC2=CC=CC=C2O1 AOHYZOQLEUTIOK-UHFFFAOYSA-N 0.000 description 2
- NIJFGSNJAWEWNU-UHFFFAOYSA-N 2-[4-(1,3-benzoxazol-2-yl)phenyl]acetic acid Chemical class C1=CC(CC(=O)O)=CC=C1C1=NC2=CC=CC=C2O1 NIJFGSNJAWEWNU-UHFFFAOYSA-N 0.000 description 2
- DIEPGNPDXOEPMF-UHFFFAOYSA-N 2-[4-(bromomethyl)phenyl]-5,7-dichloro-1,3-benzoxazole Chemical compound N=1C2=CC(Cl)=CC(Cl)=C2OC=1C1=CC=C(CBr)C=C1 DIEPGNPDXOEPMF-UHFFFAOYSA-N 0.000 description 2
- YPMOSFLHSWFWMO-UHFFFAOYSA-N 2-[4-(bromomethyl)phenyl]-7-chloro-1,3-benzoxazole Chemical compound O1C=2C(Cl)=CC=CC=2N=C1C1=CC=C(CBr)C=C1 YPMOSFLHSWFWMO-UHFFFAOYSA-N 0.000 description 2
- YNEXPZBQRZDROJ-UHFFFAOYSA-N 2-fluoro-n-(2-hydroxyphenyl)-4-methylbenzamide Chemical compound FC1=CC(C)=CC=C1C(=O)NC1=CC=CC=C1O YNEXPZBQRZDROJ-UHFFFAOYSA-N 0.000 description 2
- GGSNKPVLVSSJRR-UHFFFAOYSA-N 7-chloro-2-(4-methylphenyl)-1,3-benzoxazole Chemical compound C1=CC(C)=CC=C1C1=NC2=CC=CC(Cl)=C2O1 GGSNKPVLVSSJRR-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 238000011914 asymmetric synthesis Methods 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- VPYIUNFTBVAXHC-UHFFFAOYSA-N methyl 2-[4-(1,3-benzoxazol-2-yl)phenyl]acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1C1=NC2=CC=CC=C2O1 VPYIUNFTBVAXHC-UHFFFAOYSA-N 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- YFRMSGJWNBWYLR-UHFFFAOYSA-N n-(2-hydroxyphenyl)bicyclo[4.2.0]octa-1(6),2,4,7-tetraene-4-carboxamide Chemical compound OC1=CC=CC=C1NC(=O)C1=CC=C(C=C2)C2=C1 YFRMSGJWNBWYLR-UHFFFAOYSA-N 0.000 description 2
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 150000002905 orthoesters Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- 229910000634 wood's metal Inorganic materials 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- LIUSHSVUMMYGRB-UHFFFAOYSA-N 1-naphthalen-1-yl-n-phenoxymethanamine Chemical compound C=1C=CC2=CC=CC=C2C=1CNOC1=CC=CC=C1 LIUSHSVUMMYGRB-UHFFFAOYSA-N 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- DCTFLNVNPBQXCA-UHFFFAOYSA-N 2-(4-ethyl-2-fluorophenyl)-1,3-benzoxazole Chemical compound FC1=CC(CC)=CC=C1C1=NC2=CC=CC=C2O1 DCTFLNVNPBQXCA-UHFFFAOYSA-N 0.000 description 1
- KZTWONRVIPPDKH-UHFFFAOYSA-N 2-(piperidin-1-yl)ethanol Chemical compound OCCN1CCCCC1 KZTWONRVIPPDKH-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/39—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups
- C07C205/42—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/43—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7122770A | 1970-09-10 | 1970-09-10 | |
| US16538971A | 1971-07-22 | 1971-07-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO136712B true NO136712B (enrdf_load_stackoverflow) | 1977-07-18 |
| NO136712C NO136712C (no) | 1977-10-26 |
Family
ID=26751978
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3355/71A NO136712C (no) | 1970-09-10 | 1971-09-09 | Analogifremgangsm}te ved fremstilling av terapeutisk aktive benzoxazolforbindelser. |
Country Status (23)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3816443A (en) * | 1972-02-17 | 1974-06-11 | Merck & Co Inc | 4-(benzothiazol-2-yl)fluoro phenyl-acetic acids |
| GB1435721A (en) * | 1972-05-18 | 1976-05-12 | Lilly Industries Ltd | Benzoxazole derivatives |
| GB1495488A (en) * | 1976-06-23 | 1977-12-21 | Ippco Int Pharma Patents Co Es | Optically active 2-(2-phenyl-5-benzoxazolyl)propionic acids |
| IT1099589B (it) * | 1978-08-04 | 1985-09-18 | Ravizza Spa | Processo per la preparazione di derivati dell'acido benzoxazolil propionico |
| IT1157295B (it) * | 1982-07-19 | 1987-02-11 | Ravizza Spa | Processo perfezionato per la preparazione di derivati dell'acido benzoxazolil propionico |
| DE19808261A1 (de) * | 1998-02-27 | 1999-10-28 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
| WO2008035359A2 (en) * | 2006-06-12 | 2008-03-27 | Cadila Healthcare Limited | Oximinophenoxyalkanoic acid and phenylalkanoic acid derivatives |
| JP2008232573A (ja) * | 2007-03-22 | 2008-10-02 | Osaka Gas Co Ltd | 吸収冷凍機 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD70880A (enrdf_load_stackoverflow) * | ||||
| CH483276A (de) * | 1959-09-23 | 1969-12-31 | Ciba Geigy | Verwendung von 2-Phenyl-benzazolen als Schutzmittel vor ultravioletter Strahlung ausserhalb der Textilindustrie |
| US3401120A (en) * | 1965-10-23 | 1968-09-10 | Gaf Corp | Corrosion inhibitors |
| CH514616A (de) * | 1968-10-07 | 1971-10-31 | Ciba Geigy Ag | Verfahren zur Herstellung von Arylenoxazolen |
-
1971
- 1971-09-01 IL IL37633A patent/IL37633A/xx unknown
- 1971-09-02 OA OA54349A patent/OA03911A/xx unknown
- 1971-09-02 AU AU33024/71A patent/AU461109B2/en not_active Expired
- 1971-09-03 CH CH1295571A patent/CH572916A5/xx not_active IP Right Cessation
- 1971-09-06 GB GB4149971A patent/GB1352723A/en not_active Expired
- 1971-09-06 PH PH12818A patent/PH11935A/en unknown
- 1971-09-06 AT AT773871A patent/AT311964B/de not_active IP Right Cessation
- 1971-09-07 IE IE1136/71A patent/IE35599B1/xx unknown
- 1971-09-07 YU YU2279/71A patent/YU34689B/xx unknown
- 1971-09-08 EG EG396/71*UA patent/EG10421A/xx active
- 1971-09-08 PL PL1971150397A patent/PL81813B1/pl unknown
- 1971-09-09 LU LU63887D patent/LU63887A1/xx unknown
- 1971-09-09 NO NO3355/71A patent/NO136712C/no unknown
- 1971-09-09 SE SE11441/71A patent/SE367203B/xx unknown
- 1971-09-09 DE DE2145203A patent/DE2145203C2/de not_active Expired
- 1971-09-09 NL NLAANVRAGE7112437,A patent/NL174043C/xx not_active IP Right Cessation
- 1971-09-09 SU SU1696052A patent/SU455542A3/ru active
- 1971-09-09 DD DD157648A patent/DD94814A5/xx unknown
- 1971-09-09 FI FI2524/71A patent/FI55196C/fi active
- 1971-09-09 BE BE772395A patent/BE772395A/xx not_active IP Right Cessation
- 1971-09-10 JP JP6981371A patent/JPS544953B1/ja active Pending
- 1971-09-10 RO RO68180A patent/RO61539A/ro unknown
- 1971-09-10 FR FR7132748A patent/FR2106434B1/fr not_active Expired
-
1977
- 1977-11-02 JP JP52130931A patent/JPS6044304B2/ja not_active Expired
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