DD211560A5 - Verfahren zur herstellung kristalliner benzothiazindioxid-salze - Google Patents
Verfahren zur herstellung kristalliner benzothiazindioxid-salze Download PDFInfo
- Publication number
- DD211560A5 DD211560A5 DD82240299A DD24029982A DD211560A5 DD 211560 A5 DD211560 A5 DD 211560A5 DD 82240299 A DD82240299 A DD 82240299A DD 24029982 A DD24029982 A DD 24029982A DD 211560 A5 DD211560 A5 DD 211560A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- benzothiazine
- dioxide
- pyridyl
- hydroxy
- carboxamide
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- MJNPHLBKHKJDEF-UHFFFAOYSA-N 2h-1$l^{4},2-benzothiazine 1-oxide Chemical class C1=CC=C2S(=O)NC=CC2=C1 MJNPHLBKHKJDEF-UHFFFAOYSA-N 0.000 title 1
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical class OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 13
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims abstract description 12
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims abstract description 11
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims abstract description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 150000002169 ethanolamines Chemical class 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 239000003586 protic polar solvent Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 abstract description 23
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
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- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 4
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- 229940124597 therapeutic agent Drugs 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
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- 244000215068 Acacia senegal Species 0.000 description 1
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- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
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- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
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- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
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- 150000004760 silicates Chemical class 0.000 description 1
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26898081A | 1981-06-01 | 1981-06-01 | |
| US06/367,067 US4434164A (en) | 1981-06-01 | 1982-04-13 | Crystalline benzothiazine dioxide salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD211560A5 true DD211560A5 (de) | 1984-07-18 |
Family
ID=26953436
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD82240299A DD211560A5 (de) | 1981-06-01 | 1982-05-28 | Verfahren zur herstellung kristalliner benzothiazindioxid-salze |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4434164A (enExample) |
| EP (1) | EP0066459B1 (enExample) |
| KR (1) | KR850001883B1 (enExample) |
| AU (1) | AU529386B2 (enExample) |
| BG (1) | BG37377A3 (enExample) |
| CA (1) | CA1209571A (enExample) |
| DD (1) | DD211560A5 (enExample) |
| DE (1) | DE3260718D1 (enExample) |
| DK (1) | DK149024C (enExample) |
| EG (1) | EG15811A (enExample) |
| ES (1) | ES512723A0 (enExample) |
| FI (1) | FI74705C (enExample) |
| GB (1) | GB2101589A (enExample) |
| GR (1) | GR75476B (enExample) |
| HK (1) | HK65386A (enExample) |
| HU (1) | HU189586B (enExample) |
| IE (1) | IE53160B1 (enExample) |
| IL (1) | IL65917A (enExample) |
| MX (1) | MX6984E (enExample) |
| MY (1) | MY8700126A (enExample) |
| NO (1) | NO157979C (enExample) |
| NZ (1) | NZ200801A (enExample) |
| OA (1) | OA07114A (enExample) |
| PH (1) | PH17906A (enExample) |
| PT (1) | PT74977B (enExample) |
| RO (1) | RO84698B (enExample) |
| YU (1) | YU42767B (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5913714A (ja) * | 1982-07-13 | 1984-01-24 | Taito Pfizer Kk | 外用消炎鎮痛剤 |
| RO88420A (ro) * | 1983-04-25 | 1986-01-30 | Pfizer Inc,Us | Procedeu pentru prepararea unor saruri bazice de piroxican depuse pe suporturi farmaceutice |
| DE3431588A1 (de) * | 1983-09-12 | 1985-04-04 | Pfizer, Inc., New York, N.Y. | Kristalline benzothiazindioxid-salze und diese enthaltende pharmazeutische zusammensetzungen |
| DE3346526C2 (de) * | 1983-12-22 | 1986-12-11 | A. Nattermann & Cie GmbH, 5000 Köln | Pharmazeutisches Präparat zur therapeutischen Behandlung von rheumatischen Erkrankungen |
| IT1196307B (it) * | 1984-10-22 | 1988-11-16 | Chiesi Farma Spa | Formulazioni farmaceutiche acquose di piroxicam monoidrato |
| US4582831A (en) | 1984-11-16 | 1986-04-15 | Pfizer Inc. | Anti-inflammatory polymorphic monoethanolamine salt of N-(2-pyridyl)-2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide compound, composition, and method of use therefor |
| US4559326A (en) * | 1985-01-31 | 1985-12-17 | Pfizer Inc. | Antiinflammatory compositions and methods |
| 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 |
| KR890001236B1 (ko) * | 1985-10-02 | 1989-04-28 | 화이자 인코포레이티드 | 소염제 조성물의 제조방법 |
| HU200926B (en) * | 1988-10-28 | 1990-09-28 | Egyt Gyogyszervegyeszeti Gyar | Pharmaceutical composition comprising piroxicam and lactose for use in making tablets or capsules |
| IT1247492B (it) * | 1991-04-18 | 1994-12-17 | Francia Farma | Sali ad attivita' antiinfiammatoria, antisettica, detergente e composizioni farmaceutiche |
| IT1283252B1 (it) * | 1996-03-15 | 1998-04-16 | Pulitzer Italiana | Soluzioni di piroxicam iniettabili per via parenterale |
| GB0031107D0 (en) * | 2000-12-20 | 2001-01-31 | Glaxo Group Ltd | Chemical compounds |
| FR2818641B1 (fr) * | 2000-12-21 | 2004-03-05 | Servier Lab | Nouveaux derives de 1,1-dioxo-2h-1,2-benzothiazine 3-carboxamides, leur procede de preparation et les compositions pharmaceutiques que les contiennent |
| KR100446829B1 (ko) * | 2002-02-20 | 2004-09-04 | 한국유나이티드제약 주식회사 | 가용화된 피록시캄을 함유한 확산형 정제의 조성물 및그의 제조방법 |
| ES2622471T5 (es) | 2003-05-22 | 2020-07-23 | United Therapeutics Corp | Compuestos y procedimientos para la administración de análogos de prostaciclina |
| US20050176809A1 (en) * | 2004-02-05 | 2005-08-11 | Rodlen Laboratories, Inc. | Method and compositions for treatment of painful disorders |
| EP1893190A4 (en) * | 2005-04-28 | 2010-07-28 | Theraquest Biosciences Llc | METHODS AND COMPOSITIONS FOR TREATING PAIN |
| US8747897B2 (en) | 2006-04-27 | 2014-06-10 | Supernus Pharmaceuticals, Inc. | Osmotic drug delivery system |
| JP5851691B2 (ja) | 2007-12-17 | 2016-02-03 | ユナイテッド セラピューティクス コーポレーション | リモジュリンの活性成分であるトレプロスチニルを製造する改良方法 |
| US9593061B2 (en) | 2014-10-20 | 2017-03-14 | United Therapeutics Corporation | Synthesis of intermediates for producing prostacyclin derivatives |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3591584A (en) | 1968-08-27 | 1971-07-06 | Pfizer | Benzothiazine dioxides |
| 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 |
| DE2756113A1 (de) | 1977-12-16 | 1979-06-21 | Thomae Gmbh Dr K | Neue 4-hydroxy-2h-1,2-benzothiazin- 3-carboxamid-1,1-dioxide, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
| US4289879A (en) | 1980-09-29 | 1981-09-15 | Pfizer Inc. | Synthetic method and intermediate for piroxicam |
-
1982
- 1982-04-13 US US06/367,067 patent/US4434164A/en not_active Expired - Lifetime
- 1982-05-26 BG BG056786A patent/BG37377A3/xx unknown
- 1982-05-27 NO NO821767A patent/NO157979C/no not_active IP Right Cessation
- 1982-05-27 HU HU821721A patent/HU189586B/hu unknown
- 1982-05-27 EP EP82302729A patent/EP0066459B1/en not_active Expired
- 1982-05-27 RO RO107688A patent/RO84698B/ro unknown
- 1982-05-27 DE DE8282302729T patent/DE3260718D1/de not_active Expired
- 1982-05-28 IE IE1286/82A patent/IE53160B1/en not_active IP Right Cessation
- 1982-05-28 YU YU1137/82A patent/YU42767B/xx unknown
- 1982-05-28 DK DK241682A patent/DK149024C/da not_active IP Right Cessation
- 1982-05-28 CA CA000403957A patent/CA1209571A/en not_active Expired
- 1982-05-28 OA OA57703A patent/OA07114A/xx unknown
- 1982-05-28 DD DD82240299A patent/DD211560A5/de not_active IP Right Cessation
- 1982-05-30 EG EG304/82A patent/EG15811A/xx active
- 1982-05-31 MX MX8210098U patent/MX6984E/es unknown
- 1982-05-31 AU AU84322/82A patent/AU529386B2/en not_active Expired
- 1982-05-31 KR KR8202425A patent/KR850001883B1/ko not_active Expired
- 1982-05-31 NZ NZ200801A patent/NZ200801A/en unknown
- 1982-05-31 ES ES512723A patent/ES512723A0/es active Granted
- 1982-05-31 PT PT74977A patent/PT74977B/pt unknown
- 1982-05-31 IL IL65917A patent/IL65917A/xx unknown
- 1982-05-31 GR GR68300A patent/GR75476B/el unknown
- 1982-05-31 FI FI821918A patent/FI74705C/fi not_active IP Right Cessation
- 1982-06-01 GB GB08215966A patent/GB2101589A/en not_active Withdrawn
- 1982-06-01 PH PH27387A patent/PH17906A/en unknown
-
1986
- 1986-09-04 HK HK653/86A patent/HK65386A/en not_active IP Right Cessation
-
1987
- 1987-12-30 MY MY126/87A patent/MY8700126A/xx unknown
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