NO880167L - Fremgangsmaate for fremstilling av benzotiazindioksyd-derivater. - Google Patents
Fremgangsmaate for fremstilling av benzotiazindioksyd-derivater.Info
- Publication number
- NO880167L NO880167L NO88880167A NO880167A NO880167L NO 880167 L NO880167 L NO 880167L NO 88880167 A NO88880167 A NO 88880167A NO 880167 A NO880167 A NO 880167A NO 880167 L NO880167 L NO 880167L
- Authority
- NO
- Norway
- Prior art keywords
- compound
- set forth
- methyl
- pyridyl
- carbon atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 36
- -1 6-methyl-2-pyridyl Chemical group 0.000 claims description 25
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 230000004968 inflammatory condition Effects 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 238000010992 reflux Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 238000001914 filtration Methods 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 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 12
- 239000000047 product Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000002274 desiccant Substances 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- 239000012299 nitrogen atmosphere Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 229940111133 antiinflammatory and antirheumatic drug oxicams Drugs 0.000 description 9
- 239000012267 brine Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 235000009518 sodium iodide Nutrition 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000000862 absorption spectrum Methods 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 229940002612 prodrug Drugs 0.000 description 7
- 239000000651 prodrug Substances 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 235000010418 carrageenan Nutrition 0.000 description 6
- 229920001525 carrageenan Polymers 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000004949 mass spectrometry Methods 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 description 4
- HAGTVFOITQBIHW-UHFFFAOYSA-N 3-bromopropyl methyl carbonate Chemical compound COC(=O)OCCCBr HAGTVFOITQBIHW-UHFFFAOYSA-N 0.000 description 4
- RSWQKVAOUINGEF-UHFFFAOYSA-N CC(CCCBr)OC(=O)O Chemical compound CC(CCCBr)OC(=O)O RSWQKVAOUINGEF-UHFFFAOYSA-N 0.000 description 4
- RPVZYKQUQDZYSX-UHFFFAOYSA-N CCCCCCCC(CCCBr)OC(=O)O Chemical compound CCCCCCCC(CCCBr)OC(=O)O RPVZYKQUQDZYSX-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000012263 liquid product Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 230000003637 steroidlike Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 229940124597 therapeutic agent Drugs 0.000 description 4
- 230000000699 topical effect Effects 0.000 description 4
- NMYQDCMIAVBQOF-UHFFFAOYSA-N 4-(3-hydroxypropoxy)-2-methyl-1,1-dioxo-n-pyridin-2-yl-1$l^{6},2-benzothiazine-3-carboxamide Chemical compound OCCCOC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 NMYQDCMIAVBQOF-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 208000025865 Ulcer Diseases 0.000 description 3
- 230000001760 anti-analgesic effect Effects 0.000 description 3
- 239000002260 anti-inflammatory agent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- GQWALAJLRYQAQY-UHFFFAOYSA-N 4-(5-hydroxypentoxy)-2-methyl-1,1-dioxo-n-pyridin-2-yl-1$l^{6},2-benzothiazine-3-carboxamide Chemical compound OCCCCCOC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 GQWALAJLRYQAQY-UHFFFAOYSA-N 0.000 description 2
- NIGKHKLDZOHYMT-UHFFFAOYSA-N 4-hydroxy-2-methyl-n-(6-methylpyridin-2-yl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxamide Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC(C)=N1 NIGKHKLDZOHYMT-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- 206010030124 Oedema peripheral Diseases 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 239000000679 carrageenan Substances 0.000 description 2
- 229940113118 carrageenan Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- RAOUTGWFHDBIAQ-UHFFFAOYSA-N ethyl 3-[[2-methyl-1,1-dioxo-3-(pyridin-2-ylcarbamoyl)-1$l^{6},2-benzothiazin-4-yl]oxy]propyl carbonate Chemical compound CN1S(=O)(=O)C2=CC=CC=C2C(OCCCOC(=O)OCC)=C1C(=O)NC1=CC=CC=N1 RAOUTGWFHDBIAQ-UHFFFAOYSA-N 0.000 description 2
- VQCOVZBGVOGWOD-UHFFFAOYSA-N ethyl 4-[[2-methyl-1,1-dioxo-3-(pyridin-2-ylcarbamoyl)-1$l^{6},2-benzothiazin-4-yl]oxy]butyl carbonate Chemical compound CN1S(=O)(=O)C2=CC=CC=C2C(OCCCCOC(=O)OCC)=C1C(=O)NC1=CC=CC=N1 VQCOVZBGVOGWOD-UHFFFAOYSA-N 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 229960002895 phenylbutazone Drugs 0.000 description 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 2
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- GHNLJDPNIAIWOQ-UHFFFAOYSA-N 2h-1$l^{6},2-benzothiazine 1,1-dioxide Chemical class C1=CC=C2S(=O)(=O)NC=CC2=C1 GHNLJDPNIAIWOQ-UHFFFAOYSA-N 0.000 description 1
- SIJLYRDVTMMSIP-UHFFFAOYSA-N 4-Bromo-1-butanol Chemical compound OCCCCBr SIJLYRDVTMMSIP-UHFFFAOYSA-N 0.000 description 1
- VRURUAOIZXDXFC-UHFFFAOYSA-N 4-bromobutyl ethyl carbonate Chemical compound CCOC(=O)OCCCCBr VRURUAOIZXDXFC-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- SYCHUQUJURZQMO-UHFFFAOYSA-N 4-hydroxy-2-methyl-1,1-dioxo-n-(1,3-thiazol-2-yl)-1$l^{6},2-benzothiazine-3-carboxamide Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=CS1 SYCHUQUJURZQMO-UHFFFAOYSA-N 0.000 description 1
- DCBJCKDOZLTTDW-UHFFFAOYSA-N 5-chloropentan-1-ol Chemical compound OCCCCCCl DCBJCKDOZLTTDW-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 229940124346 antiarthritic agent Drugs 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 210000002683 foot Anatomy 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- VYVIEPGVTQJORL-UHFFFAOYSA-N methyl 3-[[2-methyl-1,1-dioxo-3-(pyridin-2-ylcarbamoyl)-1$l^{6},2-benzothiazin-4-yl]oxy]propyl carbonate Chemical compound CN1S(=O)(=O)C2=CC=CC=C2C(OCCCOC(=O)OC)=C1C(=O)NC1=CC=CC=N1 VYVIEPGVTQJORL-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- VFXVAXFIFHSGNR-UHFFFAOYSA-N octyl carbonochloridate Chemical compound CCCCCCCCOC(Cl)=O VFXVAXFIFHSGNR-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229960002702 piroxicam Drugs 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
- C07D279/08—1,3-Thiazines; Hydrogenated 1,3-thiazines condensed with carbocyclic rings or ring systems
-
- 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
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/02—1,2-Thiazines; Hydrogenated 1,2-thiazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1986/001048 WO1987006933A1 (en) | 1986-05-16 | 1986-05-16 | Benzothiazine dioxide derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO880167D0 NO880167D0 (no) | 1988-01-15 |
| NO880167L true NO880167L (no) | 1988-03-15 |
Family
ID=22195499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO88880167A NO880167L (no) | 1986-05-16 | 1988-01-15 | Fremgangsmaate for fremstilling av benzotiazindioksyd-derivater. |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4829062A (de) |
| EP (1) | EP0246045A3 (de) |
| JP (1) | JPS62277384A (de) |
| KR (1) | KR890005204B1 (de) |
| CN (1) | CN87103608A (de) |
| AT (1) | AT388732B (de) |
| AU (1) | AU567429B1 (de) |
| CA (1) | CA1277662C (de) |
| DD (1) | DD260700A5 (de) |
| DK (1) | DK245687A (de) |
| EG (1) | EG18318A (de) |
| FI (1) | FI880177A7 (de) |
| HU (1) | HU199833B (de) |
| IL (1) | IL82482A0 (de) |
| MX (1) | MX6506A (de) |
| MY (1) | MY101557A (de) |
| NO (1) | NO880167L (de) |
| NZ (1) | NZ220328A (de) |
| PH (1) | PH22947A (de) |
| PL (1) | PL149608B1 (de) |
| PT (1) | PT84868B (de) |
| WO (1) | WO1987006933A1 (de) |
| YU (1) | YU46203B (de) |
| ZA (1) | ZA873459B (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5081118A (en) * | 1987-10-26 | 1992-01-14 | Pfizer Inc. | Benzothiazine dioxide derivatives |
| GB0724625D0 (en) * | 2007-12-18 | 2008-01-30 | Glaxo Group Ltd | Novel compounds |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3591584A (en) * | 1968-08-27 | 1971-07-06 | Pfizer | Benzothiazine dioxides |
| 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 |
| AU473890B2 (en) * | 1971-06-22 | 1976-07-08 | Warner-Lambert Company | 4-ACYLOXY-3-(3-ISOXAZOLOCARBAMHL)-2H-l, 2 BENZOTHIAZINE 1, 1-DIOXIDES |
| US3925371A (en) * | 1974-09-23 | 1975-12-09 | Mcneilab Inc | Benzothiazine-1,1-dioxides |
| US3892740A (en) * | 1974-10-15 | 1975-07-01 | Pfizer | Process for the production of carboxamides of oxo-1,2-benzothiazine-1,1-dioxides |
| US4289879A (en) * | 1980-09-29 | 1981-09-15 | Pfizer Inc. | Synthetic method and intermediate for piroxicam |
| US4309427A (en) * | 1981-01-15 | 1982-01-05 | Pfizer Inc. | Benzothiazine dioxide derivatives |
| IN156884B (de) * | 1981-08-21 | 1985-11-30 | Pfizer | |
| JPS59193879A (ja) * | 1983-03-31 | 1984-11-02 | Fujisawa Pharmaceut Co Ltd | トロポン誘導体 |
| IN162323B (de) * | 1983-12-21 | 1988-04-30 | Pfizer | |
| US4551452A (en) * | 1983-12-21 | 1985-11-05 | Pfizer Inc. | Anti-inflammatory 2-methyl-2H-1,2-benzo-(or -thieno-)thiazine-3-carboxamide 1,1-dioxide derivatives, compositions, and method of use therefor |
-
1986
- 1986-05-16 FI FI880177A patent/FI880177A7/fi not_active Application Discontinuation
- 1986-05-16 HU HU863402A patent/HU199833B/hu not_active IP Right Cessation
- 1986-05-16 MX MX650687A patent/MX6506A/es unknown
- 1986-05-16 US US07/154,245 patent/US4829062A/en not_active Expired - Fee Related
- 1986-05-16 WO PCT/US1986/001048 patent/WO1987006933A1/en not_active Ceased
-
1987
- 1987-05-08 EP EP87304139A patent/EP0246045A3/de not_active Withdrawn
- 1987-05-11 IL IL82482A patent/IL82482A0/xx not_active IP Right Cessation
- 1987-05-11 EG EG271/87A patent/EG18318A/xx active
- 1987-05-14 DD DD87302783A patent/DD260700A5/de not_active IP Right Cessation
- 1987-05-14 DK DK245687A patent/DK245687A/da not_active Application Discontinuation
- 1987-05-14 PL PL1987265698A patent/PL149608B1/pl unknown
- 1987-05-14 CA CA000537123A patent/CA1277662C/en not_active Expired - Lifetime
- 1987-05-14 PT PT84868A patent/PT84868B/pt not_active IP Right Cessation
- 1987-05-14 PH PH35257A patent/PH22947A/en unknown
- 1987-05-14 ZA ZA873459A patent/ZA873459B/xx unknown
- 1987-05-15 NZ NZ220328A patent/NZ220328A/xx unknown
- 1987-05-15 KR KR1019870004795A patent/KR890005204B1/ko not_active Expired
- 1987-05-15 MY MYPI87000657A patent/MY101557A/en unknown
- 1987-05-15 CN CN198787103608A patent/CN87103608A/zh active Pending
- 1987-05-15 AU AU72976/87A patent/AU567429B1/en not_active Ceased
- 1987-05-15 YU YU87487A patent/YU46203B/sh unknown
- 1987-05-16 JP JP62119974A patent/JPS62277384A/ja active Pending
- 1987-10-08 AT AT0262987A patent/AT388732B/de not_active IP Right Cessation
-
1988
- 1988-01-15 NO NO88880167A patent/NO880167L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0246045A3 (de) | 1989-04-26 |
| DD260700A5 (de) | 1988-10-05 |
| FI880177A0 (fi) | 1988-01-15 |
| MX6506A (es) | 1993-10-01 |
| ZA873459B (en) | 1988-01-27 |
| PL265698A1 (en) | 1988-04-28 |
| JPS62277384A (ja) | 1987-12-02 |
| HU199833B (en) | 1990-03-28 |
| AT388732B (de) | 1989-08-25 |
| DK245687A (da) | 1987-11-17 |
| CA1277662C (en) | 1990-12-11 |
| FI880177L (fi) | 1988-01-15 |
| IL82482A0 (en) | 1987-11-30 |
| DK245687D0 (da) | 1987-05-14 |
| FI880177A7 (fi) | 1988-01-15 |
| PH22947A (en) | 1989-02-03 |
| PT84868A (en) | 1987-06-01 |
| ATA262987A (de) | 1989-01-15 |
| CN87103608A (zh) | 1987-12-30 |
| NO880167D0 (no) | 1988-01-15 |
| WO1987006933A1 (en) | 1987-11-19 |
| EP0246045A2 (de) | 1987-11-19 |
| PL149608B1 (en) | 1990-02-28 |
| EG18318A (en) | 1993-02-28 |
| NZ220328A (en) | 1989-08-29 |
| PT84868B (pt) | 1990-02-08 |
| US4829062A (en) | 1989-05-09 |
| AU567429B1 (en) | 1987-11-19 |
| YU87487A (en) | 1988-10-31 |
| KR890005204B1 (ko) | 1989-12-18 |
| MY101557A (en) | 1991-12-17 |
| YU46203B (sh) | 1993-05-28 |
| HUT48238A (en) | 1989-05-29 |
| KR870011118A (ko) | 1987-12-21 |
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