DD216460A5 - Verfahren zur herstellung von piroxicam und zu diesem fuehrende zwischenstufen - Google Patents
Verfahren zur herstellung von piroxicam und zu diesem fuehrende zwischenstufen Download PDFInfo
- Publication number
- DD216460A5 DD216460A5 DD82257459A DD25745982A DD216460A5 DD 216460 A5 DD216460 A5 DD 216460A5 DD 82257459 A DD82257459 A DD 82257459A DD 25745982 A DD25745982 A DD 25745982A DD 216460 A5 DD216460 A5 DD 216460A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- methyl
- hydroxy
- piroxicam
- och
- benzothiazine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 28
- 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 title abstract description 13
- 229960002702 piroxicam Drugs 0.000 title abstract description 13
- 229910052987 metal hydride Inorganic materials 0.000 claims abstract description 14
- 150000004681 metal hydrides Chemical class 0.000 claims abstract description 14
- -1 alkyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxides Chemical class 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 48
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 37
- 239000000460 chlorine Substances 0.000 claims description 26
- 239000012442 inert solvent Substances 0.000 claims description 13
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 13
- 239000012312 sodium hydride Substances 0.000 claims description 11
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 9
- 125000000217 alkyl group Chemical group 0.000 abstract description 7
- DDIIAJRLFATEEE-UHFFFAOYSA-N 2-methyl-1,1-dioxo-1,2-benzothiazol-3-one Chemical compound C1=CC=C2S(=O)(=O)N(C)C(=O)C2=C1 DDIIAJRLFATEEE-UHFFFAOYSA-N 0.000 abstract description 6
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract description 3
- 239000002260 anti-inflammatory agent Substances 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000000047 product Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- VJGMQUWZFATDFA-UHFFFAOYSA-N 2-methoxyethyl 4-hydroxy-2-methyl-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylate Chemical compound C1=CC=C2S(=O)(=O)N(C)C(C(=O)OCCOC)=C(O)C2=C1 VJGMQUWZFATDFA-UHFFFAOYSA-N 0.000 description 2
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 2
- 229910000105 potassium hydride Inorganic materials 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000004400 (C1-C12) alkyl group Chemical group 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
- CUIGSPBMMQWNLR-UHFFFAOYSA-N 2-isocyanatopyridine Chemical compound O=C=NC1=CC=CC=N1 CUIGSPBMMQWNLR-UHFFFAOYSA-N 0.000 description 1
- SVLBINWLZIVRJX-UHFFFAOYSA-N 2-methoxyethyl 2-chloroacetate Chemical compound COCCOC(=O)CCl SVLBINWLZIVRJX-UHFFFAOYSA-N 0.000 description 1
- PVNIYDCDHSFJTK-UHFFFAOYSA-N 2h-1,2-benzothiazin-4-ol Chemical group C1=CC=C2C(O)=CNSC2=C1 PVNIYDCDHSFJTK-UHFFFAOYSA-N 0.000 description 1
- RQRCJRUUPFZABV-UHFFFAOYSA-N 4-hydroxy-2-methyl-1,2-benzothiazine-3-carboxylic acid Chemical compound C1=CC=C2C(O)=C(C(O)=O)N(C)SC2=C1 RQRCJRUUPFZABV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
- 125000002587 enol group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 1
- NGHIOTWSWSQQNT-UHFFFAOYSA-N methyl 4-hydroxy-2-methyl-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylate Chemical compound C1=CC=C2S(=O)(=O)N(C)C(C(=O)OC)=C(O)C2=C1 NGHIOTWSWSQQNT-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- HWEXKRHYVOGVDA-UHFFFAOYSA-M sodium;3-trimethylsilylpropane-1-sulfonate Chemical compound [Na+].C[Si](C)(C)CCCS([O-])(=O)=O HWEXKRHYVOGVDA-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000007056 transamidation reaction Methods 0.000 description 1
- 238000005406 washing 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
- C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compounds Of Unknown Constitution (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/308,746 US4376204A (en) | 1981-10-05 | 1981-10-05 | 3-Hydroxy 2-methyl benzisothiazolines as intermediates in production of piroxicam |
| US41303682A | 1982-09-02 | 1982-09-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD216460A5 true DD216460A5 (de) | 1984-12-12 |
Family
ID=26976430
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD82243802A DD203051A5 (de) | 1981-10-05 | 1982-10-05 | Verfahren zur herstellung von piroxicam |
| DD82257459A DD216460A5 (de) | 1981-10-05 | 1982-10-05 | Verfahren zur herstellung von piroxicam und zu diesem fuehrende zwischenstufen |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD82243802A DD203051A5 (de) | 1981-10-05 | 1982-10-05 | Verfahren zur herstellung von piroxicam |
Country Status (27)
| Country | Link |
|---|---|
| EP (1) | EP0076643B1 (en, 2012) |
| KR (1) | KR850001223B1 (en, 2012) |
| AT (1) | ATE11916T1 (en, 2012) |
| AU (1) | AU534759B2 (en, 2012) |
| BG (2) | BG40812A3 (en, 2012) |
| CA (1) | CA1187873A (en, 2012) |
| DD (2) | DD203051A5 (en, 2012) |
| DE (1) | DE3262440D1 (en, 2012) |
| DK (2) | DK154646C (en, 2012) |
| EG (1) | EG15847A (en, 2012) |
| ES (2) | ES516208A0 (en, 2012) |
| FI (1) | FI75342C (en, 2012) |
| GR (1) | GR77345B (en, 2012) |
| HK (1) | HK52687A (en, 2012) |
| HU (1) | HU186977B (en, 2012) |
| IE (1) | IE53957B1 (en, 2012) |
| IL (1) | IL66921A0 (en, 2012) |
| IN (1) | IN159273B (en, 2012) |
| MY (1) | MY8700510A (en, 2012) |
| NO (1) | NO157140C (en, 2012) |
| NZ (1) | NZ202062A (en, 2012) |
| PH (2) | PH17991A (en, 2012) |
| PL (2) | PL136540B1 (en, 2012) |
| PT (1) | PT75642B (en, 2012) |
| RO (2) | RO84510B (en, 2012) |
| SG (1) | SG22987G (en, 2012) |
| YU (2) | YU42804B (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69824863T2 (de) * | 1997-09-05 | 2005-06-30 | Warner-Lambert Co. Llc | Benzothiazindioxid-endothelin antagonisten und verfahren zu ihrer herstellung |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3591584A (en) * | 1968-08-27 | 1971-07-06 | Pfizer | Benzothiazine dioxides |
| US3853862A (en) * | 1973-04-23 | 1974-12-10 | Pfizer | Production of 4-hydroxy-1,2-benzothiazine-3-carboxamides |
| US3891637A (en) * | 1974-10-01 | 1975-06-24 | Pfizer | Process for the production of carboxamides of oxo-1,2-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 |
| US3960856A (en) * | 1975-06-20 | 1976-06-01 | Warner-Lambert Company | Process for the preparation of 4-hydroxy-3-(5-methyl-3-isoxazolylcarbamoyl)-2-methyl-2H-1,2-benzothiazine 1,1-dioxide |
| SE421792B (sv) * | 1976-01-12 | 1982-02-01 | Pfizer | Forfarande for framstellning av n-(2-pyridyl)-4-hydroxi-2-metyl-2h-1,2-benso-tiazin-3-karboxamid-1,1-dioxid |
| US4074048A (en) * | 1976-05-10 | 1978-02-14 | Warner-Lambert Company | Process for the preparation of 4-hydroxy-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxides |
| US4100347A (en) * | 1976-06-10 | 1978-07-11 | Pfizer Inc. | 3,4-Dihydro-2-methyl-4-oxo-2H-1,2-benzothiazine-3-carboxylic acid-1,1-dioxide |
| US4289879A (en) * | 1980-09-29 | 1981-09-15 | Pfizer Inc. | Synthetic method and intermediate for piroxicam |
-
1982
- 1982-09-22 IN IN719/DEL/82A patent/IN159273B/en unknown
- 1982-09-29 AT AT82305174T patent/ATE11916T1/de not_active IP Right Cessation
- 1982-09-29 DE DE8282305174T patent/DE3262440D1/de not_active Expired
- 1982-09-29 EP EP82305174A patent/EP0076643B1/en not_active Expired
- 1982-09-30 AU AU88917/82A patent/AU534759B2/en not_active Ceased
- 1982-09-30 IL IL66921A patent/IL66921A0/xx not_active IP Right Cessation
- 1982-10-01 PT PT75642A patent/PT75642B/pt not_active IP Right Cessation
- 1982-10-01 GR GR69420A patent/GR77345B/el unknown
- 1982-10-01 NZ NZ202062A patent/NZ202062A/en unknown
- 1982-10-04 ES ES516208A patent/ES516208A0/es active Granted
- 1982-10-04 CA CA000412724A patent/CA1187873A/en not_active Expired
- 1982-10-04 RO RO108738A patent/RO84510B/ro unknown
- 1982-10-04 BG BG058162A patent/BG40812A3/xx unknown
- 1982-10-04 IE IE2393/82A patent/IE53957B1/en not_active IP Right Cessation
- 1982-10-04 FI FI823366A patent/FI75342C/fi not_active IP Right Cessation
- 1982-10-04 RO RO112350A patent/RO86733B/ro unknown
- 1982-10-04 PH PH27950A patent/PH17991A/en unknown
- 1982-10-04 BG BG061608A patent/BG40811A3/xx unknown
- 1982-10-04 YU YU2228/82A patent/YU42804B/xx unknown
- 1982-10-04 DK DK439482A patent/DK154646C/da not_active IP Right Cessation
- 1982-10-04 NO NO823330A patent/NO157140C/no unknown
- 1982-10-05 HU HU823194A patent/HU186977B/hu not_active IP Right Cessation
- 1982-10-05 PL PL1982244761A patent/PL136540B1/pl unknown
- 1982-10-05 PL PL1982238506A patent/PL136931B1/pl unknown
- 1982-10-05 DD DD82243802A patent/DD203051A5/de not_active IP Right Cessation
- 1982-10-05 EG EG594/82A patent/EG15847A/xx active
- 1982-10-05 KR KR8204482A patent/KR850001223B1/ko not_active Expired
- 1982-10-05 DD DD82257459A patent/DD216460A5/de not_active IP Right Cessation
-
1983
- 1983-05-27 ES ES522788A patent/ES8407034A1/es not_active Expired
-
1984
- 1984-06-07 PH PH30790-AA patent/PH19297A/en unknown
- 1984-09-10 YU YU1560/84A patent/YU42903B/xx unknown
-
1987
- 1987-03-09 SG SG229/87A patent/SG22987G/en unknown
- 1987-07-09 HK HK526/87A patent/HK52687A/xx unknown
- 1987-12-30 MY MY510/87A patent/MY8700510A/xx unknown
-
1988
- 1988-04-14 DK DK204888A patent/DK154139C/da not_active IP Right Cessation
Also Published As
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