NO852062L - Fremgangsmaate til fremstilling av ny resorcineter. - Google Patents
Fremgangsmaate til fremstilling av ny resorcineter.Info
- Publication number
- NO852062L NO852062L NO852062A NO852062A NO852062L NO 852062 L NO852062 L NO 852062L NO 852062 A NO852062 A NO 852062A NO 852062 A NO852062 A NO 852062A NO 852062 L NO852062 L NO 852062L
- Authority
- NO
- Norway
- Prior art keywords
- hydroxy
- phenoxy
- propyloxy
- propyl
- atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 30
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- -1 5-tetrazolyl Chemical group 0.000 claims abstract description 175
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 133
- 150000003839 salts Chemical class 0.000 claims abstract description 112
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 90
- 239000001257 hydrogen Substances 0.000 claims abstract description 90
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 90
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 64
- 150000002367 halogens Chemical class 0.000 claims abstract description 63
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 52
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 36
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 15
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
- 125000001589 carboacyl group Chemical group 0.000 claims abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 111
- 150000001875 compounds Chemical class 0.000 claims description 105
- 239000002253 acid Substances 0.000 claims description 56
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 claims description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
- 125000002947 alkylene group Chemical group 0.000 claims description 33
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 26
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 23
- 241000534944 Thia Species 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 12
- 150000007513 acids Chemical class 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 9
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- GXWJRCAZEOWQEF-UHFFFAOYSA-N 2-[5-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-methylanilino]-2-oxoacetic acid Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC=C(C)C(NC(=O)C(O)=O)=C1 GXWJRCAZEOWQEF-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 159000000000 sodium salts Chemical class 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000003111 oxaloamino group Chemical group C(=O)(C(=O)O)N* 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- JHLVGBARNAMROS-UHFFFAOYSA-N 2-[5-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-4-bromo-2-methylanilino]-2-oxoacetic acid Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC(NC(=O)C(O)=O)=C(C)C=C1Br JHLVGBARNAMROS-UHFFFAOYSA-N 0.000 claims description 5
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- UMODZFBVNIPJGW-UHFFFAOYSA-N 2-[4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3-methoxyanilino]-2-oxoacetic acid Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC=C(NC(=O)C(O)=O)C=C1OC UMODZFBVNIPJGW-UHFFFAOYSA-N 0.000 claims description 3
- HUQNNRLFBAVIDF-UHFFFAOYSA-N 2-[5-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-chloro-4-methylanilino]-2-oxoacetic acid Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC(NC(=O)C(O)=O)=C(Cl)C=C1C HUQNNRLFBAVIDF-UHFFFAOYSA-N 0.000 claims description 3
- XPIXHYMFCDMETN-UHFFFAOYSA-N methyl 2-[3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]anilino]-2-oxoacetate Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC=CC(NC(=O)C(=O)OC)=C1 XPIXHYMFCDMETN-UHFFFAOYSA-N 0.000 claims description 3
- RMUOYVMKOKUKDX-UHFFFAOYSA-N methyl 2-[5-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-4-bromo-2-methylanilino]-2-oxoacetate Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC(NC(=O)C(=O)OC)=C(C)C=C1Br RMUOYVMKOKUKDX-UHFFFAOYSA-N 0.000 claims description 3
- WZDKNZRDLDMCAQ-UHFFFAOYSA-N 2-[4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-methylanilino]-2-oxoacetic acid Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC=C(NC(=O)C(O)=O)C(C)=C1 WZDKNZRDLDMCAQ-UHFFFAOYSA-N 0.000 claims description 2
- VAPOYESKELANAI-UHFFFAOYSA-N 2-[4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]anilino]-2-oxoacetic acid Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC=C(NC(=O)C(O)=O)C=C1 VAPOYESKELANAI-UHFFFAOYSA-N 0.000 claims description 2
- FEHQKQTXLKNMGF-UHFFFAOYSA-N 2-[5-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-4-chloro-2-methylanilino]-2-oxoacetic acid Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC(NC(=O)C(O)=O)=C(C)C=C1Cl FEHQKQTXLKNMGF-UHFFFAOYSA-N 0.000 claims description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Natural products OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 2
- JRIRWNTZPMPSBH-UHFFFAOYSA-N methyl 2-[5-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2,4-dimethylanilino]-2-oxoacetate Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC(NC(=O)C(=O)OC)=C(C)C=C1C JRIRWNTZPMPSBH-UHFFFAOYSA-N 0.000 claims description 2
- WBFJWRGDLOILEF-UHFFFAOYSA-N methyl 2-[5-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-4-chloro-2-methylanilino]-2-oxoacetate Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC(NC(=O)C(=O)OC)=C(C)C=C1Cl WBFJWRGDLOILEF-UHFFFAOYSA-N 0.000 claims description 2
- LHWIZFRBNIQQKC-UHFFFAOYSA-N n-[3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]phenyl]-2h-tetrazole-5-carboxamide Chemical compound C1=CC(C(C)=O)=C(O)C(CCC)=C1OCCCOC1=CC=CC(NC(=O)C=2NN=NN=2)=C1 LHWIZFRBNIQQKC-UHFFFAOYSA-N 0.000 claims description 2
- BWXNROFODQKHRS-UHFFFAOYSA-N 2-[3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-cyanoanilino]-2-oxoacetic acid Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC=CC(NC(=O)C(O)=O)=C1C#N BWXNROFODQKHRS-UHFFFAOYSA-N 0.000 claims 1
- RUOIWSOWFWSPQM-UHFFFAOYSA-N 2-[3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-methylanilino]-2-oxoacetic acid Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC=CC(NC(=O)C(O)=O)=C1C RUOIWSOWFWSPQM-UHFFFAOYSA-N 0.000 claims 1
- NPQDXGDCAUIDPY-UHFFFAOYSA-N 2-[3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-4-methoxycarbonylanilino]-2-oxoacetic acid Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC(NC(=O)C(O)=O)=CC=C1C(=O)OC NPQDXGDCAUIDPY-UHFFFAOYSA-N 0.000 claims 1
- OVWRFOGMGMTIAB-UHFFFAOYSA-N 2-[5-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-bromo-4-methylanilino]-2-oxoacetic acid Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC(NC(=O)C(O)=O)=C(Br)C=C1C OVWRFOGMGMTIAB-UHFFFAOYSA-N 0.000 claims 1
- 125000003943 azolyl group Chemical group 0.000 claims 1
- CQKXLIZRLWZSES-UHFFFAOYSA-N ethyl 2-[5-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-4-bromo-2-methylanilino]-2-oxoacetate Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC(NC(=O)C(=O)OCC)=C(C)C=C1Br CQKXLIZRLWZSES-UHFFFAOYSA-N 0.000 claims 1
- BXAZZURSMJRVSW-UHFFFAOYSA-N methyl 2-[3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2,4,6-trichloroanilino]-2-oxoacetate Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=C(Cl)C=C(Cl)C(NC(=O)C(=O)OC)=C1Cl BXAZZURSMJRVSW-UHFFFAOYSA-N 0.000 claims 1
- UOUXVNCAIRIDSZ-UHFFFAOYSA-N methyl 2-[5-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-chloro-4-methylanilino]-2-oxoacetate Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC(NC(=O)C(=O)OC)=C(Cl)C=C1C UOUXVNCAIRIDSZ-UHFFFAOYSA-N 0.000 claims 1
- NCVYMVDWZRKZPV-UHFFFAOYSA-N methyl 2-[5-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-4-chloro-2-(trifluoromethyl)anilino]-2-oxoacetate Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC(NC(=O)C(=O)OC)=C(C(F)(F)F)C=C1Cl NCVYMVDWZRKZPV-UHFFFAOYSA-N 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- HREMVEDROKCDGX-UHFFFAOYSA-N n-[5-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-bromo-4-methylphenyl]-1h-1,2,4-triazole-5-carboxamide Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC(NC(=O)C=2NN=CN=2)=C(Br)C=C1C HREMVEDROKCDGX-UHFFFAOYSA-N 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 abstract description 8
- 150000002170 ethers Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 169
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 159
- 238000002844 melting Methods 0.000 description 96
- 230000008018 melting Effects 0.000 description 96
- 239000000243 solution Substances 0.000 description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 37
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 230000002829 reductive effect Effects 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000003208 petroleum Substances 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 27
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 25
- 239000000460 chlorine Substances 0.000 description 25
- 229910052801 chlorine Inorganic materials 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 239000002585 base Substances 0.000 description 24
- 239000000725 suspension Substances 0.000 description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- 239000003795 chemical substances by application Substances 0.000 description 21
- 238000002425 crystallisation Methods 0.000 description 21
- 230000008025 crystallization Effects 0.000 description 21
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 21
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 20
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 20
- 229910052794 bromium Inorganic materials 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000007858 starting material Substances 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
- 239000004480 active ingredient Substances 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 17
- 239000013543 active substance Substances 0.000 description 16
- 229910052938 sodium sulfate Inorganic materials 0.000 description 16
- 235000011152 sodium sulphate Nutrition 0.000 description 16
- 235000019439 ethyl acetate Nutrition 0.000 description 15
- 230000005764 inhibitory process Effects 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- 125000002252 acyl group Chemical group 0.000 description 14
- 125000003431 oxalo group Chemical group 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 239000003826 tablet Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 11
- 229910052500 inorganic mineral Inorganic materials 0.000 description 11
- 235000010755 mineral Nutrition 0.000 description 11
- 239000011707 mineral Substances 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 10
- 239000000825 pharmaceutical preparation Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- 239000007868 Raney catalyst Substances 0.000 description 9
- 229910000564 Raney nickel Inorganic materials 0.000 description 9
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 9
- 239000000443 aerosol Substances 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- 239000012442 inert solvent Substances 0.000 description 9
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 229920002472 Starch Polymers 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 235000019698 starch Nutrition 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- RUAGNSOWWKWPHG-UHFFFAOYSA-N 1-[4-[3-(5-amino-2-bromo-4-methylphenoxy)propoxy]-2-hydroxy-3-propylphenyl]ethanone Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC(N)=C(C)C=C1Br RUAGNSOWWKWPHG-UHFFFAOYSA-N 0.000 description 7
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 239000008101 lactose Substances 0.000 description 7
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000008107 starch Substances 0.000 description 7
- JDLOGDFKWPWQMR-UHFFFAOYSA-N 1-[4-[3-(5-amino-4-chloro-2-methylphenoxy)propoxy]-2-hydroxy-3-propylphenyl]ethanone Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC(N)=C(Cl)C=C1C JDLOGDFKWPWQMR-UHFFFAOYSA-N 0.000 description 6
- ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 description 6
- 108010010803 Gelatin Proteins 0.000 description 6
- 102000015439 Phospholipases Human genes 0.000 description 6
- 108010064785 Phospholipases Proteins 0.000 description 6
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- UOXSZCIHGDNBMK-UHFFFAOYSA-N n-[5-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-bromo-4-methylphenyl]-1-[(4-methoxyphenyl)methyl]tetrazole-5-carboxamide Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC(NC(=O)C=2N(N=NN=2)CC=2C=CC(OC)=CC=2)=C(Br)C=C1C UOXSZCIHGDNBMK-UHFFFAOYSA-N 0.000 description 1
- LNLKJSBRVVIJKJ-UHFFFAOYSA-N n-[5-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-chloro-4-methylphenyl]-2h-tetrazole-5-carboxamide Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC(NC(=O)C2=NNN=N2)=C(Cl)C=C1C LNLKJSBRVVIJKJ-UHFFFAOYSA-N 0.000 description 1
- CGSLMRKGISKBDG-UHFFFAOYSA-N n-[5-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-4-bromo-2-methylphenyl]-2h-tetrazole-5-carboxamide Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC(NC(=O)C2=NNN=N2)=C(C)C=C1Br CGSLMRKGISKBDG-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000007923 nasal drop Substances 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 230000003448 neutrophilic effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- UWBHMRBRLOJJAA-UHFFFAOYSA-N oxaluric acid Chemical group NC(=O)NC(=O)C(O)=O UWBHMRBRLOJJAA-UHFFFAOYSA-N 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- UMPKMCDVBZFQOK-UHFFFAOYSA-N potassium;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[K+].[Fe+3] UMPKMCDVBZFQOK-UHFFFAOYSA-N 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 229940116317 potato starch Drugs 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 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
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000006965 reversible inhibition Effects 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 229940100890 silver compound Drugs 0.000 description 1
- 150000003379 silver compounds Chemical class 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910001494 silver tetrafluoroborate Inorganic materials 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 239000007974 sodium acetate buffer Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000011697 sodium iodate Substances 0.000 description 1
- 235000015281 sodium iodate Nutrition 0.000 description 1
- 229940032753 sodium iodate Drugs 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- FAGLEPBREOXSAC-UHFFFAOYSA-N tert-butyl isocyanide Chemical compound CC(C)(C)[N+]#[C-] FAGLEPBREOXSAC-UHFFFAOYSA-N 0.000 description 1
- AWDBHOZBRXWRKS-UHFFFAOYSA-N tetrapotassium;iron(6+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+6].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] AWDBHOZBRXWRKS-UHFFFAOYSA-N 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- SYRHIZPPCHMRIT-UHFFFAOYSA-N tin(4+) Chemical compound [Sn+4] SYRHIZPPCHMRIT-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- DRDCQJADRSJFFD-UHFFFAOYSA-N tris-hydroxymethyl-methyl-ammonium Chemical class OC[N+](C)(CO)CO DRDCQJADRSJFFD-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000005199 ultracentrifugation Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified 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
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified 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 the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Air Bags (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
- Ultra Sonic Daignosis Equipment (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Physical Deposition Of Substances That Are Components Of Semiconductor Devices (AREA)
- Detergent Compositions (AREA)
- Cephalosporin Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Investigation Of Foundation Soil And Reinforcement Of Foundation Soil By Compacting Or Drainage (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH255884 | 1984-05-24 | ||
| CH70285 | 1985-02-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO852062L true NO852062L (no) | 1985-11-25 |
Family
ID=25685423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO852062A NO852062L (no) | 1984-05-24 | 1985-05-23 | Fremgangsmaate til fremstilling av ny resorcineter. |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4863942A (fi) |
| EP (1) | EP0165897B1 (fi) |
| KR (1) | KR910003336B1 (fi) |
| AT (1) | ATE41415T1 (fi) |
| AU (1) | AU585226B2 (fi) |
| CA (1) | CA1247628A (fi) |
| DE (1) | DE3568773D1 (fi) |
| DK (1) | DK229785A (fi) |
| ES (3) | ES8701708A1 (fi) |
| FI (1) | FI852036L (fi) |
| GR (1) | GR851262B (fi) |
| HU (1) | HU198443B (fi) |
| IL (1) | IL75285A (fi) |
| NO (1) | NO852062L (fi) |
| NZ (1) | NZ212171A (fi) |
| PH (1) | PH22620A (fi) |
| PT (1) | PT80509B (fi) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT81492B (pt) * | 1985-09-17 | 1988-03-03 | Ciba Geigy Ag | Processo para a preparacao de novos eteres de resorcina fluorados |
| US5261353A (en) * | 1990-11-05 | 1993-11-16 | Stevenson Dale V | Udder care plus indicator |
| DE4323409A1 (de) * | 1993-07-13 | 1995-01-19 | Boehringer Mannheim Gmbh | Verwendung von Cumarinen und Carbostyrilen als PLA¶2¶-Inhibitoren, neue Cumarine und Carbostyrile, Verfahren zu ihrer Herstellung und Arzneimittel |
| DE60233812D1 (de) * | 2001-10-12 | 2009-11-05 | Lasser Family Partnership L P | Konzentriertes x-ray kontrastmittel effektiv als universal antigen und zur verhütung oder vermeidung von allergischen reaktionen |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3966965A (en) * | 1973-03-23 | 1976-06-29 | American Home Products Corporation | Oxamic acid derivatives for the prevention of immediate type hypersensitivity reactions |
| NL7810634A (nl) * | 1977-10-28 | 1979-05-02 | May & Baker Ltd | Tetrazool-derivaten. |
| AU543739B2 (en) * | 1979-09-05 | 1985-05-02 | Glaxo Group Limited | Phenol derivatives |
| US4448729A (en) * | 1982-08-25 | 1984-05-15 | American Home Products Corporation | Leucotriene antagonists |
| GB8333665D0 (en) * | 1983-12-16 | 1984-01-25 | Lilly Industries Ltd | Organic compounds |
| AU4987185A (en) * | 1985-11-13 | 1987-05-21 | Ciba-Geigy Ag | Fluorinated resorcinols and ethers thereof |
-
1985
- 1985-05-17 AT AT85810237T patent/ATE41415T1/de not_active IP Right Cessation
- 1985-05-17 DE DE8585810237T patent/DE3568773D1/de not_active Expired
- 1985-05-17 EP EP85810237A patent/EP0165897B1/de not_active Expired
- 1985-05-22 CA CA000482023A patent/CA1247628A/en not_active Expired
- 1985-05-22 GR GR851262A patent/GR851262B/el unknown
- 1985-05-22 FI FI852036A patent/FI852036L/fi not_active Application Discontinuation
- 1985-05-22 ES ES543390A patent/ES8701708A1/es not_active Expired
- 1985-05-22 IL IL75285A patent/IL75285A/xx unknown
- 1985-05-22 PT PT80509A patent/PT80509B/pt not_active IP Right Cessation
- 1985-05-23 NZ NZ212171A patent/NZ212171A/en unknown
- 1985-05-23 AU AU42814/85A patent/AU585226B2/en not_active Ceased
- 1985-05-23 DK DK229785A patent/DK229785A/da not_active Application Discontinuation
- 1985-05-23 HU HU851963A patent/HU198443B/hu not_active IP Right Cessation
- 1985-05-23 NO NO852062A patent/NO852062L/no unknown
- 1985-05-24 KR KR1019850003591A patent/KR910003336B1/ko active IP Right Grant
- 1985-05-24 PH PH32312A patent/PH22620A/en unknown
-
1986
- 1986-06-02 ES ES555598A patent/ES8800886A1/es not_active Expired
- 1986-06-02 ES ES555597A patent/ES8801781A1/es not_active Expired
- 1986-09-25 US US06/911,553 patent/US4863942A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DK229785A (da) | 1985-11-25 |
| CA1247628A (en) | 1988-12-28 |
| AU585226B2 (en) | 1989-06-15 |
| PH22620A (en) | 1988-10-28 |
| ES555597A0 (es) | 1988-02-16 |
| HU198443B (en) | 1989-10-30 |
| GR851262B (fi) | 1985-11-25 |
| NZ212171A (en) | 1988-01-08 |
| KR910003336B1 (ko) | 1991-05-27 |
| DE3568773D1 (en) | 1989-04-20 |
| US4863942A (en) | 1989-09-05 |
| PT80509A (de) | 1985-06-01 |
| ATE41415T1 (de) | 1989-04-15 |
| AU4281485A (en) | 1985-11-28 |
| DK229785D0 (da) | 1985-05-23 |
| ES8800886A1 (es) | 1987-12-01 |
| HUT38295A (en) | 1986-05-28 |
| EP0165897A2 (de) | 1985-12-27 |
| IL75285A0 (en) | 1985-09-29 |
| ES555598A0 (es) | 1987-12-01 |
| ES8801781A1 (es) | 1988-02-16 |
| EP0165897B1 (de) | 1989-03-15 |
| ES8701708A1 (es) | 1986-12-01 |
| KR850008333A (ko) | 1985-12-16 |
| ES543390A0 (es) | 1986-12-01 |
| FI852036A0 (fi) | 1985-05-22 |
| PT80509B (de) | 1987-04-21 |
| FI852036L (fi) | 1985-11-25 |
| EP0165897A3 (en) | 1986-03-26 |
| IL75285A (en) | 1989-03-31 |
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