NO850725L - Fremgangsmaate for fremstilling av terapeutisk aktive oksikam-derivater. - Google Patents
Fremgangsmaate for fremstilling av terapeutisk aktive oksikam-derivater.Info
- Publication number
- NO850725L NO850725L NO850725A NO850725A NO850725L NO 850725 L NO850725 L NO 850725L NO 850725 A NO850725 A NO 850725A NO 850725 A NO850725 A NO 850725A NO 850725 L NO850725 L NO 850725L
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- formula
- dioxide
- carboxamide
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 6
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 25
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- -1 5-methylisoxazol-3-yl Chemical group 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 7
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 150000003461 sulfonyl halides Chemical class 0.000 claims description 4
- 125000005425 toluyl group Chemical group 0.000 claims description 4
- SYRJEZZQHMIQCS-UHFFFAOYSA-N CN1C(C(=O)NC2=NC(Cl)=CC=C2)=C(OS(=O)(=O)C2=CC=CC=C2)C2=C(C=CC=C2)S1(=O)=O Chemical compound CN1C(C(=O)NC2=NC(Cl)=CC=C2)=C(OS(=O)(=O)C2=CC=CC=C2)C2=C(C=CC=C2)S1(=O)=O SYRJEZZQHMIQCS-UHFFFAOYSA-N 0.000 claims description 3
- WBJQLGCAGQMLOZ-UHFFFAOYSA-N [2-methyl-3-[(5-methyl-1,2-oxazol-3-yl)carbamoyl]-1,1-dioxo-1lambda6,2-benzothiazin-4-yl] benzoate Chemical compound CC1=CC(=NO1)NC(=O)C=1N(S(C2=C(C1OC(C1=CC=CC=C1)=O)C=CC=C2)(=O)=O)C WBJQLGCAGQMLOZ-UHFFFAOYSA-N 0.000 claims description 3
- MROTXUNEFMXPDV-UHFFFAOYSA-N [3-[(6-chloropyridin-2-yl)carbamoyl]-2-methyl-1,1-dioxo-1lambda6,2-benzothiazin-4-yl] hexanoate Chemical compound ClC1=CC=CC(=N1)NC(=O)C=1N(S(C2=C(C1OC(CCCCC)=O)C=CC=C2)(=O)=O)C MROTXUNEFMXPDV-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- JBBZSYXYWVWGHR-UHFFFAOYSA-N [2-methyl-3-[(5-methyl-1,2-oxazol-3-yl)carbamoyl]-1,1-dioxo-1lambda6,2-benzothiazin-4-yl] hexanoate Chemical compound CC1=CC(=NO1)NC(=O)C=1N(S(C2=C(C=1OC(CCCCC)=O)C=CC=C2)(=O)=O)C JBBZSYXYWVWGHR-UHFFFAOYSA-N 0.000 claims description 2
- BHZBGNAAOTWHLF-UHFFFAOYSA-N [3-[(6-chloropyridin-2-yl)carbamoyl]-2-methyl-1,1-dioxo-1lambda6,2-benzothiazin-4-yl] benzoate Chemical compound ClC1=CC=CC(=N1)NC(=O)C=1N(S(C2=C(C1OC(C1=CC=CC=C1)=O)C=CC=C2)(=O)=O)C BHZBGNAAOTWHLF-UHFFFAOYSA-N 0.000 claims description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000011630 iodine Chemical group 0.000 claims description 2
- 229910052740 iodine Chemical group 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 229940111133 antiinflammatory and antirheumatic drug oxicams Drugs 0.000 description 14
- 239000007787 solid Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- 230000003110 anti-inflammatory effect Effects 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 239000000651 prodrug Substances 0.000 description 5
- 229940002612 prodrug Drugs 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000002260 anti-inflammatory agent Substances 0.000 description 3
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 208000009386 Experimental Arthritis Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 206010030124 Oedema peripheral Diseases 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- PFDBGXHVSBXDHS-UHFFFAOYSA-N n-(6-chloropyridin-2-yl)-4-hydroxy-2-methyl-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxamide Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC(Cl)=N1 PFDBGXHVSBXDHS-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003180 prostaglandins Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- NUBKYCCXDNYHLQ-UHFFFAOYSA-N 2,2-dimethylpentanoyl chloride Chemical compound CCCC(C)(C)C(Cl)=O NUBKYCCXDNYHLQ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 208000016557 Acute basophilic leukemia Diseases 0.000 description 1
- NYEXFUDGXRXJJN-UHFFFAOYSA-N CC1=CC(=NO1)NC(=O)C2=C(C3=CC=CC=C3S(=O)(=O)N2C)OS(=O)(=O)C4=CC=CC=C4 Chemical compound CC1=CC(=NO1)NC(=O)C2=C(C3=CC=CC=C3S(=O)(=O)N2C)OS(=O)(=O)C4=CC=CC=C4 NYEXFUDGXRXJJN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 206010053155 Epigastric discomfort Diseases 0.000 description 1
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- GYVWVGAURDLIMY-UHFFFAOYSA-N [2-methyl-1,1-dioxo-3-(phenylcarbamoyl)-1$l^{6},2-benzothiazin-4-yl] acetate Chemical compound CC(=O)OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=C1 GYVWVGAURDLIMY-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- YYUAYBYLJSNDCX-UHFFFAOYSA-N isoxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC=1C=C(C)ON=1 YYUAYBYLJSNDCX-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000006241 metabolic reaction Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000002437 synoviocyte Anatomy 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58268484A | 1984-02-23 | 1984-02-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO850725L true NO850725L (no) | 1985-08-26 |
Family
ID=24330094
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO850725A NO850725L (no) | 1984-02-23 | 1985-02-22 | Fremgangsmaate for fremstilling av terapeutisk aktive oksikam-derivater. |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS60184077A (fr) |
| KR (1) | KR850006198A (fr) |
| AU (1) | AU552478B2 (fr) |
| BE (1) | BE901783A (fr) |
| DD (1) | DD232045A5 (fr) |
| DE (1) | DE3505576A1 (fr) |
| DK (1) | DK81185A (fr) |
| ES (1) | ES8606312A1 (fr) |
| FI (1) | FI850742L (fr) |
| FR (1) | FR2565980A1 (fr) |
| GB (1) | GB2154585A (fr) |
| GR (1) | GR850442B (fr) |
| HU (1) | HUT37616A (fr) |
| IL (1) | IL74407A0 (fr) |
| IT (1) | IT1185514B (fr) |
| LU (1) | LU85780A1 (fr) |
| NL (1) | NL8500485A (fr) |
| NO (1) | NO850725L (fr) |
| PL (1) | PL252023A1 (fr) |
| PT (1) | PT79988B (fr) |
| SE (1) | SE8500889L (fr) |
| ZA (1) | ZA851317B (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4623486A (en) * | 1985-05-29 | 1986-11-18 | Pfizer Inc. | [4-substituted benzoyloxy]-N-substituted-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxides having anti-arthritic activity |
| US4610982A (en) * | 1985-06-03 | 1986-09-09 | Pfizer Inc. | Anti-inflammatory benzo- and thieno-1,2-thiazine-3-carboxamide 1,1-dioxide derivatives, compositions, and method of use therefor |
| US20090221703A1 (en) | 2006-07-09 | 2009-09-03 | Chongxi Yu | High penetration composition and uses thereof |
| US20090238763A1 (en) | 2006-07-09 | 2009-09-24 | Chongxi Yu | High penetration compositions and uses thereof |
| JP5378221B2 (ja) * | 2006-10-11 | 2013-12-25 | テックフィールズ バイオケム カンパニー リミテッド | 非常に高い皮膚浸透率を有するオキシカム及び関連化合物の正荷電水溶性プロドラッグ |
| CN101687792B (zh) | 2007-06-04 | 2016-03-02 | 于崇曦 | 具有快速皮肤和生物膜穿透速度的非甾体抗炎药的前药及其医药用途 |
| KR101946297B1 (ko) | 2008-12-04 | 2019-02-11 | 충시 위 | 고투과력을 가진 조성물 및 이의 적용 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3591574A (en) * | 1968-05-29 | 1971-07-06 | American Home Prod | Tri-n-phenylglycyl derivatives of insulin |
| US3787324A (en) * | 1971-03-01 | 1974-01-22 | Warner Lambert Co | 4-hydroxy-3-(3-isoxazolocarbamyl)-2h-1,2-benzothiazine 1,dioxides and process for their production |
| US3704298A (en) * | 1971-06-22 | 1972-11-28 | Warner Lambert Co | 4-acyloxy-3-(2-isoxazolocarbamyl)-2h-1,2-benzothiazine 1,1-dioxides |
| AU518216B2 (en) * | 1977-09-06 | 1981-09-17 | Hafslund Nycomed Pharma Aktiengesellschaft | Thienothiazine derivatives |
| JPS5714589A (en) * | 1980-06-27 | 1982-01-25 | Mitsui Toatsu Chem Inc | Benzothiazine derivative, its preparation and drug composition |
| US4309427A (en) * | 1981-01-15 | 1982-01-05 | Pfizer Inc. | Benzothiazine dioxide derivatives |
| IT8219486A0 (it) * | 1982-02-05 | 1982-02-05 | Chiesi Farma Spa | Nuovi composti ad attivita'antiinfiammatoria, procedimento per la loro preparazione e relative composizioni farmaceutiche. |
| IT1206525B (it) * | 1982-12-10 | 1989-04-27 | Zionale S R L A Roma | Preparato anti-infiammatorio nonsteroideo, per il trattamento delle affezioni artroreumatiche e metodo per la sua preparazione |
-
1985
- 1985-01-23 JP JP60010722A patent/JPS60184077A/ja active Pending
- 1985-02-18 DE DE19853505576 patent/DE3505576A1/de not_active Ceased
- 1985-02-19 PL PL25202385A patent/PL252023A1/xx unknown
- 1985-02-20 GB GB08504355A patent/GB2154585A/en not_active Withdrawn
- 1985-02-20 PT PT79988A patent/PT79988B/pt unknown
- 1985-02-20 LU LU85780A patent/LU85780A1/fr unknown
- 1985-02-20 GR GR850442A patent/GR850442B/el unknown
- 1985-02-21 DD DD85273451A patent/DD232045A5/de unknown
- 1985-02-21 ES ES540590A patent/ES8606312A1/es not_active Expired
- 1985-02-21 IL IL74407A patent/IL74407A0/xx unknown
- 1985-02-21 NL NL8500485A patent/NL8500485A/nl not_active Application Discontinuation
- 1985-02-21 BE BE0/214544A patent/BE901783A/fr not_active IP Right Cessation
- 1985-02-21 ZA ZA851317A patent/ZA851317B/xx unknown
- 1985-02-21 IT IT8519585A patent/IT1185514B/it active
- 1985-02-22 SE SE8500889A patent/SE8500889L/xx not_active Application Discontinuation
- 1985-02-22 FI FI850742A patent/FI850742L/fi not_active Application Discontinuation
- 1985-02-22 FR FR8502586A patent/FR2565980A1/fr active Pending
- 1985-02-22 DK DK81185A patent/DK81185A/da not_active Application Discontinuation
- 1985-02-22 KR KR1019850001106A patent/KR850006198A/ko not_active Application Discontinuation
- 1985-02-22 NO NO850725A patent/NO850725L/no unknown
- 1985-02-22 HU HU85678A patent/HUT37616A/hu unknown
- 1985-02-22 AU AU39066/85A patent/AU552478B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| SE8500889L (sv) | 1985-08-24 |
| LU85780A1 (fr) | 1985-12-11 |
| FI850742A0 (fi) | 1985-02-22 |
| BE901783A (fr) | 1985-08-21 |
| PT79988B (en) | 1987-02-02 |
| GB2154585A (en) | 1985-09-11 |
| DD232045A5 (de) | 1986-01-15 |
| IT8519585A0 (it) | 1985-02-21 |
| ES540590A0 (es) | 1986-04-16 |
| ES8606312A1 (es) | 1986-04-16 |
| DE3505576A1 (de) | 1985-09-05 |
| AU552478B2 (en) | 1986-06-05 |
| GR850442B (fr) | 1985-06-19 |
| FI850742L (fi) | 1985-08-24 |
| KR850006198A (ko) | 1985-10-02 |
| ZA851317B (en) | 1986-10-29 |
| PL252023A1 (en) | 1985-11-05 |
| IT1185514B (it) | 1987-11-12 |
| AU3906685A (en) | 1985-09-05 |
| NL8500485A (nl) | 1985-09-16 |
| SE8500889D0 (sv) | 1985-02-22 |
| IL74407A0 (en) | 1985-05-31 |
| HUT37616A (en) | 1986-01-23 |
| GB8504355D0 (en) | 1985-03-20 |
| DK81185D0 (da) | 1985-02-22 |
| JPS60184077A (ja) | 1985-09-19 |
| PT79988A (en) | 1985-03-01 |
| FR2565980A1 (fr) | 1985-12-20 |
| DK81185A (da) | 1985-09-10 |
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