CN101665472A - 2-甲基－3.4-二氢-4-氧代-2h-1.2-苯并噻嗪-3-羧酸乙酯-1,1-二氧化物的制备方法 - Google Patents
2-甲基－3.4-二氢-4-氧代-2h-1.2-苯并噻嗪-3-羧酸乙酯-1,1-二氧化物的制备方法 Download PDFInfo
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- CN101665472A CN101665472A CN200910015885A CN200910015885A CN101665472A CN 101665472 A CN101665472 A CN 101665472A CN 200910015885 A CN200910015885 A CN 200910015885A CN 200910015885 A CN200910015885 A CN 200910015885A CN 101665472 A CN101665472 A CN 101665472A
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- reaction
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- methyl
- benzothiazine
- dioxide
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- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 230000032050 esterification Effects 0.000 claims abstract description 15
- 238000005886 esterification reaction Methods 0.000 claims abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000007069 methylation reaction Methods 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 238000006462 rearrangement reaction Methods 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 13
- FIPBGFYKXKDTFW-UHFFFAOYSA-N 2-methyl-4-oxo-3h-1,2-benzothiazine-3-carboxylic acid Chemical compound C1=CC=C2C(=O)C(C(O)=O)N(C)SC2=C1 FIPBGFYKXKDTFW-UHFFFAOYSA-N 0.000 claims description 11
- PQLFROTZSIMBKR-UHFFFAOYSA-N ethenyl carbonochloridate Chemical compound ClC(=O)OC=C PQLFROTZSIMBKR-UHFFFAOYSA-N 0.000 claims description 5
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 230000001105 regulatory effect Effects 0.000 claims description 5
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 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
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 abstract description 5
- 239000000047 product Substances 0.000 abstract description 4
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 239000002351 wastewater Substances 0.000 abstract description 3
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 230000008707 rearrangement Effects 0.000 abstract 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 4
- 229960002702 piroxicam Drugs 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000010025 steaming Methods 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YBRHODCMROOROS-UHFFFAOYSA-N 2h-1,2-benzothiazine-3-carboxylic acid Chemical compound C1=CC=C2SNC(C(=O)O)=CC2=C1 YBRHODCMROOROS-UHFFFAOYSA-N 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
Claims (7)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009100158851A CN101665472B (zh) | 2009-06-15 | 2009-06-15 | 2-甲基-3，4-二氢-4-氧代-2h-1，2-苯并噻嗪-3-羧酸乙酯-1,1-二氧化物的制备方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009100158851A CN101665472B (zh) | 2009-06-15 | 2009-06-15 | 2-甲基-3，4-二氢-4-氧代-2h-1，2-苯并噻嗪-3-羧酸乙酯-1,1-二氧化物的制备方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101665472A true CN101665472A (zh) | 2010-03-10 |
| CN101665472B CN101665472B (zh) | 2011-08-24 |
Family
ID=41802275
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2009100158851A Active CN101665472B (zh) | 2009-06-15 | 2009-06-15 | 2-甲基-3，4-二氢-4-氧代-2h-1，2-苯并噻嗪-3-羧酸乙酯-1,1-二氧化物的制备方法 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101665472B (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108623579A (zh) * | 2018-07-11 | 2018-10-09 | 郑州明泽医药科技有限公司 | 一种吡罗昔康的合成方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3591584A (en) * | 1968-08-27 | 1971-07-06 | Pfizer | Benzothiazine dioxides |
| 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 |
| CN101210013A (zh) * | 2006-12-25 | 2008-07-02 | 林广德 | 一种Lewis酸催化氨解合成吡罗昔康的方法 |
-
2009
- 2009-06-15 CN CN2009100158851A patent/CN101665472B/zh active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108623579A (zh) * | 2018-07-11 | 2018-10-09 | 郑州明泽医药科技有限公司 | 一种吡罗昔康的合成方法 |
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| Publication number | Publication date |
|---|---|
| CN101665472B (zh) | 2011-08-24 |
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Owner name: DISHA PHARMACEUTICAL GROUP SHANDONG DISHA PHARMACE |
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Free format text: CORRECT: ADDRESS; FROM: 264205 NO. 196, KEJI ROAD, WEIHAI TORCH HIGH-TECH. INDUSTRIAL DEVELOPMENT ZONE, WEIHAI CITY, SHANDONG PROVINCE TO: 264209 NO. 196, KEJI ROAD, WEIHAI TORCH HIGH-TECH. INDUSTRIAL DEVELOPMENT ZONE, WEIHAI CITY, SHANDONG PROVINCE |
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Effective date of registration: 20110615 Address after: 264209 No. 196, science and technology road, torch hi tech Industrial Development Zone, Weihai, Shandong, Weihai Applicant after: WEIHAI DISU PHARMACEUTICAL Co.,Ltd. Co-applicant after: Shandong Disha Pharmaceutical Co.,Ltd., Disha Phamaceutical Group Co-applicant after: DISHA PHARMACEUTICAL GROUP Co.,Ltd. Address before: 264205 No. 196, science and technology road, torch hi tech Industrial Development Zone, Weihai, Shandong, Weihai Applicant before: WEIHAI DISU PHARMACEUTICAL Co.,Ltd. |
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Owner name: WEIHAI DIJIA PHARMACEUTICAL CO., LTD. Free format text: FORMER OWNER: WEIHAI DISU PHARMACEUTICAL CO., LTD. Effective date: 20140613 Owner name: WEIHAI DISU PHARMACEUTICAL CO., LTD. DISHA PHARMAC Free format text: FORMER OWNER: DISHA PHARMACEUTICAL GROUP SHANDONG DISHA PHARMACEUTICAL CO., LTD. DISHA PHARMACEUTICAL INDUSTRY GROUP CORP., LTD. Effective date: 20140613 |
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Effective date of registration: 20140613 Address after: 264400 No. 46, Guangzhou Road, Wendeng Economic Development Zone, Shandong, Weihai Patentee after: WEIHAI DIJIA PHARMACEUTICAL Co.,Ltd. Patentee after: WEIHAI DISU PHARMACEUTICAL Co.,Ltd. Patentee after: Shandong Disha Pharmaceutical Co.,Ltd., Disha Phamaceutical Group Address before: 264209 No. 196, science and technology road, torch hi tech Industrial Development Zone, Weihai, Shandong, Weihai Patentee before: WEIHAI DISU PHARMACEUTICAL Co.,Ltd. Patentee before: Shandong Disha Pharmaceutical Co.,Ltd., Disha Phamaceutical Group Patentee before: DISHA PHARMACEUTICAL GROUP Co.,Ltd. |
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Effective date of registration: 20160708 Address after: Economic and Technological Development Zone of Shandong Province, Weihai City, Gushan Town, 264209 No. 18 South Road, No. 19 North Road, No. 3 East Road, the west five Patentee after: WEIHAI DISU PHARMACEUTICAL Co.,Ltd. Address before: 264400 No. 46, Guangzhou Road, Wendeng Economic Development Zone, Shandong, Weihai Patentee before: WEIHAI DIJIA PHARMACEUTICAL Co.,Ltd. Patentee before: WEIHAI DISU PHARMACEUTICAL Co.,Ltd. Patentee before: Shandong Disha Pharmaceutical Co.,Ltd., Disha Phamaceutical Group |
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Effective date of registration: 20200513 Address after: 264205 Guangzhou East Road South and an East Road East, Wendeng economic and Technological Development Zone, Weihai City, Shandong Province Patentee after: Dijia Pharmaceutical Group Co.,Ltd. Address before: Economic and Technological Development Zone of Shandong Province, Weihai City, Gushan Town, 264209 No. 18 South Road, No. 19 North Road, No. 3 East Road, the west five Patentee before: WEIHAI DISU PHARMACEUTICAL Co.,Ltd. |
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Address after: 264205 268 Tianrun Road, Wendeng economic and Technological Development Zone, Weihai, Shandong Patentee after: Dijia Pharmaceutical Group Co.,Ltd. Address before: 264205 Wendeng economic and Technological Development Zone, Weihai City, Shandong Province Patentee before: Dijia Pharmaceutical Group Co.,Ltd. |
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Address after: No. 268, Tianrun Road, Wendeng Economic and Technological Development Zone, Weihai City, Shandong Province, 264200 Patentee after: Dijia Pharmaceutical Group Co.,Ltd. Address before: 264205 268 Tianrun Road, Wendeng economic and Technological Development Zone, Weihai, Shandong Patentee before: Dijia Pharmaceutical Group Co.,Ltd. |
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