SU1192623A3 - Способ получени сложных эфиров - Google Patents
Способ получени сложных эфиров Download PDFInfo
- Publication number
- SU1192623A3 SU1192623A3 SU823503158A SU3503158A SU1192623A3 SU 1192623 A3 SU1192623 A3 SU 1192623A3 SU 823503158 A SU823503158 A SU 823503158A SU 3503158 A SU3503158 A SU 3503158A SU 1192623 A3 SU1192623 A3 SU 1192623A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- methyl
- mol
- dioxide
- potassium
- product
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 6
- 150000002148 esters Chemical class 0.000 title description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 5
- 239000012312 sodium hydride Substances 0.000 claims description 5
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 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 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- FYRTWNBAZWPLOW-UHFFFAOYSA-N potassium;n-propan-2-ylpropan-2-amine Chemical compound [K].CC(C)NC(C)C FYRTWNBAZWPLOW-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 2
- BTNAZHHYONIOIV-UHFFFAOYSA-N 1,2-benzothiazole 1,1-dioxide Chemical compound C1=CC=C2S(=O)(=O)N=CC2=C1 BTNAZHHYONIOIV-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- MLEWYKHZOHYBHH-UHFFFAOYSA-N CC1(C(C(N=[SiH][SiH2]1)(C)C)(C)C)C.[K] Chemical compound CC1(C(C(N=[SiH][SiH2]1)(C)C)(C)C)C.[K] MLEWYKHZOHYBHH-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical class C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims 1
- 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 8
- -1 alkyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxides Chemical class 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 2
- 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 abstract 4
- 229960002702 piroxicam Drugs 0.000 abstract 4
- 239000000543 intermediate Substances 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229910052987 metal hydride Inorganic materials 0.000 abstract 2
- 150000004681 metal hydrides Chemical class 0.000 abstract 2
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 239000000047 product Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 10
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- SVLBINWLZIVRJX-UHFFFAOYSA-N 2-methoxyethyl 2-chloroacetate Chemical compound COCCOC(=O)CCl SVLBINWLZIVRJX-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 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
- 238000006243 chemical reaction Methods 0.000 description 3
- 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 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- YDCHQCZKVZFJEL-UHFFFAOYSA-N 2-methoxyethyl 2-bromoacetate Chemical compound COCCOC(=O)CBr YDCHQCZKVZFJEL-UHFFFAOYSA-N 0.000 description 1
- GUCFCUMIFFYPLN-UHFFFAOYSA-N CN1C(=C(C2=CC=CC=C2S1)O)CCOC Chemical compound CN1C(=C(C2=CC=CC=C2S1)O)CCOC GUCFCUMIFFYPLN-UHFFFAOYSA-N 0.000 description 1
- CMSZXEPIXKLTMQ-UHFFFAOYSA-N COCCC1=CC=CC2=C1C(=C(N(S2(=O)=O)C)C(=O)O)O Chemical compound COCCC1=CC=CC2=C1C(=C(N(S2(=O)=O)C)C(=O)O)O CMSZXEPIXKLTMQ-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-N 0.000 description 1
Classifications
-
- 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)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1192623A3 true SU1192623A3 (ru) | 1985-11-15 |
Family
ID=23195219
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU823503158A SU1192623A3 (ru) | 1981-10-05 | 1982-10-04 | Способ получени сложных эфиров |
| SU833649766A SU1240357A3 (ru) | 1981-10-05 | 1983-10-04 | Способ получени сложных эфиров 2-метил-4-гидрокси-2 @ -1,2-бензотиазин-3-карбоновой кислоты |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU833649766A SU1240357A3 (ru) | 1981-10-05 | 1983-10-04 | Способ получени сложных эфиров 2-метил-4-гидрокси-2 @ -1,2-бензотиазин-3-карбоновой кислоты |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4376204A (enExample) |
| JP (3) | JPS5872574A (enExample) |
| CS (1) | CS233736B2 (enExample) |
| PL (2) | PL136942B1 (enExample) |
| SU (2) | SU1192623A3 (enExample) |
| ZA (1) | ZA827258B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4483982A (en) * | 1982-09-02 | 1984-11-20 | Pfizer Inc. | Processes for preparing piroxicam and intermediates leading thereto |
| ES2002646A6 (es) * | 1987-03-27 | 1988-09-01 | Induspol Sa | Procedimiento para la obtencion de 4-hidroxi-2-metil-n-(2-piri-dil)-2h-1,2-benzotiacina-3-carboxamida 1,1-dioxido |
| US5120334A (en) * | 1991-05-23 | 1992-06-09 | Ford Motor Company | Air cleaner for internal combustion engine |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3987038A (en) * | 1975-05-21 | 1976-10-19 | Warner-Lambert Company | Process for the preparation of {1-[5-(4-hydroxy-2H-1,2-benzothiazin-3-yl)-1,2,4-oxadiazol-3-yl]methyl}ethanone S,S-dioxide |
| 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 |
| US4213980A (en) * | 1978-01-30 | 1980-07-22 | Ciba-Geigy Corporation | Azathianaphthalenes |
| 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 |
-
1981
- 1981-10-05 US US06/308,746 patent/US4376204A/en not_active Expired - Fee Related
-
1982
- 1982-10-04 ZA ZA827258A patent/ZA827258B/xx unknown
- 1982-10-04 SU SU823503158A patent/SU1192623A3/ru active
- 1982-10-05 PL PL1982244763A patent/PL136942B1/pl unknown
- 1982-10-05 PL PL1982244762A patent/PL135663B1/pl unknown
- 1982-10-05 CS CS827096A patent/CS233736B2/cs unknown
- 1982-10-05 JP JP57175249A patent/JPS5872574A/ja active Granted
-
1983
- 1983-10-04 SU SU833649766A patent/SU1240357A3/ru active
-
1987
- 1987-09-16 JP JP62231984A patent/JPS6372684A/ja active Granted
- 1987-09-16 JP JP62231985A patent/JPS6372685A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| Патент US № 3591584, кл, 260243, опублик. М971. * |
Also Published As
| Publication number | Publication date |
|---|---|
| PL244763A1 (en) | 1984-07-16 |
| JPS6372684A (ja) | 1988-04-02 |
| JPS5872574A (ja) | 1983-04-30 |
| PL135663B1 (en) | 1985-11-30 |
| CS233736B2 (en) | 1985-03-14 |
| PL136942B1 (en) | 1986-04-30 |
| ZA827258B (en) | 1983-08-31 |
| CS709682A2 (en) | 1984-06-18 |
| JPS6316384B2 (enExample) | 1988-04-08 |
| JPH0316353B2 (enExample) | 1991-03-05 |
| SU1240357A3 (ru) | 1986-06-23 |
| US4376204A (en) | 1983-03-08 |
| PL244762A1 (en) | 1984-07-16 |
| JPH0316352B2 (enExample) | 1991-03-05 |
| JPS6372685A (ja) | 1988-04-02 |
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