KR840006634A - 4-히드록시-2h-1,2-벤조티아진-3-카복사미드-1,1-디옥사이드의 제조방법 - Google Patents
4-히드록시-2h-1,2-벤조티아진-3-카복사미드-1,1-디옥사이드의 제조방법 Download PDFInfo
- Publication number
- KR840006634A KR840006634A KR1019830004772A KR830004772A KR840006634A KR 840006634 A KR840006634 A KR 840006634A KR 1019830004772 A KR1019830004772 A KR 1019830004772A KR 830004772 A KR830004772 A KR 830004772A KR 840006634 A KR840006634 A KR 840006634A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- formula
- hydroxy
- carbon atoms
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 5
- KIRHSGGIMMTVPT-UHFFFAOYSA-N 4-hydroxy-1,1-dioxo-2h-1$l^{6},2-benzothiazine-3-carboxamide Chemical compound C1=CC=C2S(=O)(=O)NC(C(=O)N)=C(O)C2=C1 KIRHSGGIMMTVPT-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 239000003513 alkali Substances 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 2
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical class OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 125000002071 phenylalkoxy group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- JTPXVCKCLBROOJ-UHFFFAOYSA-N 2-amino-6-chloropyrazine Chemical compound NC1=CN=CC(Cl)=N1 JTPXVCKCLBROOJ-UHFFFAOYSA-N 0.000 claims 1
- MDGONKGLMIHIIR-UHFFFAOYSA-N 4-hydroxy-2h-1,2-benzothiazine-3-carboxamide Chemical compound C1=CC=C2SNC(C(=O)N)=C(O)C2=C1 MDGONKGLMIHIIR-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 238000010533 azeotropic distillation Methods 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- -1 phenyloxy group Chemical group 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 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
- C07D279/02—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Hematology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (5)
- a) 하기 일반식(Ⅱ)의 4-히드록시-2H-1,2-벤조티아진-1,1-디옥사이드-3-카복실산 유도체와 하기 일반식(Ⅲ)의 2-아미노-6-클로로-피라진을 불활성 유기용매 또는 과량의 일반식(Ⅲ) 피라진 존재하에 20 내지 200℃의 온도에서반응시켜 하기 일반식(Ⅰ)의 화합물을 제조하거나,b) 하기 일반식(Ⅳ)의 4-히드록시-2H-1,2-벤조티아진-3-카복사미드를 0 내지 80℃C의 온도에서 염기존재하에 하기 일반식(Ⅴ)의 알킬할라이드로 처리하여 R1이 후술할 바와 같고, R2가 메틸, 에틸이나 n-프로필그룹인 일반식(Ⅰ)의 화합물을 제조하며, 임의로 상기 반응들을 실시하기 전에, 일반식(Ⅱ) 또는 (Ⅳ) 화합물에 있는 4-히드록시그룹을 보호하여 반응을 실시한 다음반응이 완결된후 다시 이 보호그룹을 제거하고, 필요에 따라 상기 방법들에 의하여 제조된 일반식(Ⅰ)의 화합물을 무기 또는 유기염기를 이용하여 이들의 염으로전환시킴을 특징으로 하여 하기 일반식(Ⅰ)의 4-히드록시-2H-1,2-벤조티아진-3-카복사미드-1,1-디옥사이드 및 생리적으로 허용되는 이들의 염을 제조하는 방법.상기 일반식에서,R1은 수소원자, 메틸그룹, 메톡시그룹, 불소원자 또는 염소원자이고,R2는 수소원자, 메틸그룹, 에틸그룹 또는 n-프로필그룹이며,X는 친핵적으로 치환 가능한 그룹, 특히 탄소수 1 내지 8의 알콕시그룹, 총탄소수7 내지 10의 페닐알콕시그룹, 페닐옥시그룹; 할로겐원자, 우리아미노그룹, 탄소수 1 내지 8의 알킬아미노그룹, 탄소수 3 내지 10의 시클로알킬아미노그룹 ,총탄소수 7 내지 10의 페닐알킬아미노그룹 또는 아닐리노그룹이고, Hal은 할로겐원자이며, R11은 메틸그룹, 에틸그룹 또는 n-프로필그룹이다.
- 제1a항에 있어서, 일반식(Ⅱ)에서 X가 알콕시그룹일 경우, 형성된 상응알코올을 공비증류시켜 제거함을 특징으로 하는 방법.
- 제1b항에 있어서, 사용한 염기가 수성, 알코올성 또는 수-알코올성 매질내에 있는 알칼리금속이나 알칼리토금속 수산화물, 탄산염 또는 알콕사이드 또는 3급아민이거나 비양자성 유기용매내에 있는 알칼리나 알칼리토금속 수소화물이며, 만일 알칼리나 알칼리토금속 탄염염을 사용한다면 용매로서 지방족케톤을 사용할 수도 있음을 특징으로 한 방법.
- 제1항에 있어서, 일반식(Ⅱ)에서 X가 아미노그룹, 알킬아미노그룹, 시클로알킬아미노그룹, 페닐알킬아미노그룹 또는 아닐리노그룹일 경우, 반응을 비등점에서 크실렌존재하에 실시하며, 촉매량의 p-톨루엔술폰산을 첨가함을 특징으로 하는 방법.
- 제1a와 1b항에 있어서, 일반식(Ⅱ)나 (Ⅳ) 화합물에 있는 유리 4-히드록시 그룹을 반응시키기 전에 에테르화시켜 아콕시나 페닐알콕시 그룹으로 전환시켜 반응시킨후 이러한 류의 보호그룹을 0 내지 100℃에서 무기산을 사용하거나 또는 -80 내지 +80℃에서 보론트리할라이드를 사용하여 다시 제거함을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3237473.9 | 1982-10-09 | ||
| DE19823237473 DE3237473A1 (de) | 1982-10-09 | 1982-10-09 | Neue 4-hydroxy-2h-1,2-benzothiazin-3-carboxamid-1,1-dioxide, verfahren zu ihrer herstellung, ihre verwendung und diese verbindungen enthaltende arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR840006634A true KR840006634A (ko) | 1984-12-01 |
Family
ID=6175330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830004772A KR840006634A (ko) | 1982-10-09 | 1983-10-08 | 4-히드록시-2h-1,2-벤조티아진-3-카복사미드-1,1-디옥사이드의 제조방법 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4533664A (ko) |
| EP (1) | EP0106214B1 (ko) |
| JP (1) | JPS5988482A (ko) |
| KR (1) | KR840006634A (ko) |
| AT (1) | ATE16807T1 (ko) |
| AU (1) | AU1998683A (ko) |
| CA (1) | CA1207767A (ko) |
| CS (1) | CS236896B2 (ko) |
| DD (1) | DD215549A5 (ko) |
| DE (2) | DE3237473A1 (ko) |
| DK (1) | DK460783A (ko) |
| ES (2) | ES526332A0 (ko) |
| FI (1) | FI833566A (ko) |
| GB (1) | GB2128190B (ko) |
| GR (1) | GR79010B (ko) |
| HU (1) | HU190169B (ko) |
| IL (1) | IL69931A (ko) |
| NO (1) | NO833665L (ko) |
| NZ (1) | NZ205891A (ko) |
| PH (1) | PH20402A (ko) |
| PL (1) | PL139147B1 (ko) |
| PT (1) | PT77466B (ko) |
| SU (1) | SU1148565A3 (ko) |
| ZA (1) | ZA837500B (ko) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3435843A1 (de) * | 1984-09-29 | 1986-04-03 | Gödecke AG, 1000 Berlin | Antirheumatisch wirksame suppositorien |
| US5599811A (en) * | 1995-02-21 | 1997-02-04 | Warner-Lambert Company | Benzothiazine dioxides as endothelin antagonists |
| WO2023154412A1 (en) * | 2022-02-12 | 2023-08-17 | Miralogx Llc | Anti-inflammatory compounds, pharmaceutical compositions, and treatment methods |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3591584A (en) * | 1968-08-27 | 1971-07-06 | Pfizer | Benzothiazine dioxides |
| US3891637A (en) * | 1974-10-01 | 1975-06-24 | Pfizer | Process for the production of carboxamides of oxo-1,2-benzothiazine-1,1-dioxides |
| 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 |
-
1982
- 1982-10-09 DE DE19823237473 patent/DE3237473A1/de not_active Withdrawn
-
1983
- 1983-09-24 EP EP83109512A patent/EP0106214B1/de not_active Expired
- 1983-09-24 AT AT83109512T patent/ATE16807T1/de not_active IP Right Cessation
- 1983-09-24 DE DE8383109512T patent/DE3361437D1/de not_active Expired
- 1983-09-30 US US06/537,592 patent/US4533664A/en not_active Expired - Fee Related
- 1983-10-03 FI FI833566A patent/FI833566A/fi not_active Application Discontinuation
- 1983-10-04 PH PH29650A patent/PH20402A/en unknown
- 1983-10-05 SU SU833654490A patent/SU1148565A3/ru active
- 1983-10-05 GR GR72624A patent/GR79010B/el unknown
- 1983-10-06 DK DK460783A patent/DK460783A/da not_active Application Discontinuation
- 1983-10-06 DD DD83255478A patent/DD215549A5/de unknown
- 1983-10-07 JP JP58188284A patent/JPS5988482A/ja active Pending
- 1983-10-07 AU AU19986/83A patent/AU1998683A/en not_active Abandoned
- 1983-10-07 ZA ZA837500A patent/ZA837500B/xx unknown
- 1983-10-07 CA CA000438617A patent/CA1207767A/en not_active Expired
- 1983-10-07 ES ES526332A patent/ES526332A0/es active Granted
- 1983-10-07 NO NO833665A patent/NO833665L/no unknown
- 1983-10-07 PL PL1983244080A patent/PL139147B1/pl unknown
- 1983-10-07 PT PT77466A patent/PT77466B/pt unknown
- 1983-10-07 CS CS837378A patent/CS236896B2/cs unknown
- 1983-10-07 HU HU833482A patent/HU190169B/hu unknown
- 1983-10-07 GB GB08326876A patent/GB2128190B/en not_active Expired
- 1983-10-07 NZ NZ205891A patent/NZ205891A/en unknown
- 1983-10-07 IL IL69931A patent/IL69931A/xx unknown
- 1983-10-08 KR KR1019830004772A patent/KR840006634A/ko not_active Application Discontinuation
-
1984
- 1984-04-09 ES ES531402A patent/ES531402A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| PT77466A (de) | 1983-11-01 |
| CA1207767A (en) | 1986-07-15 |
| NO833665L (no) | 1984-04-10 |
| DE3361437D1 (en) | 1986-01-16 |
| GB2128190A (en) | 1984-04-26 |
| DE3237473A1 (de) | 1984-04-12 |
| PL139147B1 (en) | 1986-12-31 |
| ES8502115A1 (es) | 1984-12-16 |
| JPS5988482A (ja) | 1984-05-22 |
| ES531402A0 (es) | 1984-12-16 |
| DK460783A (da) | 1984-04-10 |
| US4533664A (en) | 1985-08-06 |
| FI833566A (fi) | 1984-04-10 |
| GB8326876D0 (en) | 1983-11-09 |
| CS236896B2 (en) | 1985-05-15 |
| EP0106214A1 (de) | 1984-04-25 |
| HU190169B (en) | 1986-08-28 |
| ATE16807T1 (de) | 1985-12-15 |
| FI833566A0 (fi) | 1983-10-03 |
| PT77466B (de) | 1986-05-07 |
| DK460783D0 (da) | 1983-10-06 |
| HUT34472A (en) | 1985-03-28 |
| IL69931A (en) | 1987-03-31 |
| GR79010B (ko) | 1984-10-02 |
| PL244080A1 (en) | 1985-01-16 |
| GB2128190B (en) | 1986-07-02 |
| ES8501393A1 (es) | 1984-11-16 |
| PH20402A (en) | 1986-12-12 |
| SU1148565A3 (ru) | 1985-03-30 |
| IL69931A0 (en) | 1984-01-31 |
| ZA837500B (en) | 1985-06-26 |
| NZ205891A (en) | 1986-02-21 |
| ES526332A0 (es) | 1984-11-16 |
| AU1998683A (en) | 1984-04-12 |
| DD215549A5 (de) | 1984-11-14 |
| EP0106214B1 (de) | 1985-12-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR840001952A (ko) | N-(4-(3-아미노프로필) 아미노부틸)-2-(ω)-과니디노-지방산-아미도)-2-치환된-에탄아미드 이들의 염 및 이들의 제조방법 | |
| CA2137523C (en) | One-pot process for the preparation of 3-quinolonecarboxylic acid derivatives | |
| KR840001167A (ko) | 티아졸리딘알킬렌 피페라진 유도체의 제조방법 | |
| KR840000508A (ko) | 4-아닐리노피리미딘 유도체의 제조방법 | |
| US4760182A (en) | Process for preparing substituted phenol ethers via oxazolidine-structure intermediates | |
| KR880000398A (ko) | (r)-2-[4-(5-클로로-3-플루오로피리딘-2-일옥시)-페녹시]-프로피온산 프로피닐 에스테르의 제조방법 | |
| KR840006634A (ko) | 4-히드록시-2h-1,2-벤조티아진-3-카복사미드-1,1-디옥사이드의 제조방법 | |
| KR870002086A (ko) | 인돌리논 유도체의 제조 방법 | |
| KR870009989A (ko) | 스퍼구알린 (Spergualin) 관련 유도체의 제조방법 | |
| EP0061149A1 (en) | Alkylenedioxybenzene derivatives and acid addition salts thereof and a process for their preparation | |
| KR860008135A (ko) | 아미노케톤 유도체의 제조방법 | |
| KR900011751A (ko) | 선택적 에테르화 반응 | |
| KR840001974A (ko) | 1-[3-(6-플루오로-1,2-벤즈이속사졸-3-일)프로필]-4-(치환된)-피페라진 및-피레리딘의 제조방법 | |
| KR840001166A (ko) | 스피로티아졸리딘일 피페라진 유도체 제조방법 | |
| EP0391415A3 (en) | Naphthalocyanine compounds and production thereof | |
| EP1294694A2 (en) | Process for the preparation of quinoline derivatives | |
| KR850004753A (ko) | 인돌 유도체의 제조방법 | |
| US4994618A (en) | Bevantolol preparation | |
| KR910007890A (ko) | 아미노피리미딘의 제조방법 | |
| KR840006235A (ko) | 치환된 1-피리딜옥시-3-인돌일알킬아미노-2-프로판올의 제조방법 | |
| EP1007517B1 (en) | Process for the preparation of 5-hydroxymethylthiazoles | |
| IE830667L (en) | Preparation of benzothiazine derivatives | |
| KR860004004A (ko) | 4-아실옥시-3-옥소- 부티르산 에스테르의 제조방법 | |
| KR920012048A (ko) | 퀴녹살리닐옥시페녹시프로피온산의 광학적 활성 에스테르의 제조방법 | |
| US4673749A (en) | Process for producing an indoline |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |