KR850006426A - 피리도-벤조티아진 유도체의 제조방법 - Google Patents
피리도-벤조티아진 유도체의 제조방법 Download PDFInfo
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- KR850006426A KR850006426A KR1019850001180A KR850001180A KR850006426A KR 850006426 A KR850006426 A KR 850006426A KR 1019850001180 A KR1019850001180 A KR 1019850001180A KR 850001180 A KR850001180 A KR 850001180A KR 850006426 A KR850006426 A KR 850006426A
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- South Korea
- Prior art keywords
- formula
- compound
- treated
- benzothiazine
- reaction
- Prior art date
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- 238000000034 method Methods 0.000 title claims 10
- SQMFHXCAROIIPN-UHFFFAOYSA-N 2h-pyrido[2,3-h][1,2]benzothiazine Chemical class C1=CC2=NC=CC=C2C2=C1C=CNS2 SQMFHXCAROIIPN-UHFFFAOYSA-N 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 9
- 238000006243 chemical reaction Methods 0.000 claims 8
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- YSEMCVGMNUUNRK-UHFFFAOYSA-N 3-chloro-4-fluoroaniline Chemical compound NC1=CC=C(F)C(Cl)=C1 YSEMCVGMNUUNRK-UHFFFAOYSA-N 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- ARCACZWMYGILNI-UHFFFAOYSA-N 1,2,3-trifluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C(F)=C1F ARCACZWMYGILNI-UHFFFAOYSA-N 0.000 claims 2
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 claims 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- 229910010082 LiAlH Inorganic materials 0.000 claims 2
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 claims 2
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 claims 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 229920000137 polyphosphoric acid Polymers 0.000 claims 2
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 claims 2
- 229940116357 potassium thiocyanate Drugs 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 claims 2
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 claims 1
- UJVBZCCNLAAMOV-UHFFFAOYSA-N 2h-1,2-benzothiazine Chemical compound C1=CC=C2C=CNSC2=C1 UJVBZCCNLAAMOV-UHFFFAOYSA-N 0.000 claims 1
- JPJSPWJOQBDACX-UHFFFAOYSA-N 2h-1,4-benzothiazine-6-carboxylic acid Chemical compound S1CC=NC2=CC(C(=O)O)=CC=C21 JPJSPWJOQBDACX-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- BUBTTZWDGJLTSK-UHFFFAOYSA-N CC1C(SC2=CC=CC=C2N1)F Chemical compound CC1C(SC2=CC=CC=C2N1)F BUBTTZWDGJLTSK-UHFFFAOYSA-N 0.000 claims 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 150000003216 pyrazines Chemical class 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 150000003462 sulfoxides Chemical class 0.000 claims 1
- 150000003568 thioethers Chemical class 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/06—Peri-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms
-
- 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
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/16—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Luminescent Compositions (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
- Dental Preparations (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 제1단계 반응에 의해 일반식(Ⅱ)의 7-플루오로-8-할로게노-3,4-디하이드로-2H-1,4-벤조티아진을 제조한 다음, 이를 에틸에톡시메틸렌말로네이트로 처리하고 다가인산을 사용하여 폐환시켜 일반식(Ⅲ)의 에틸 9-플루오로-10-할로-3-메틸-7-옥소-2,3-디하이드로-7H-피리도[1,2,3de][1,4]-벤조티아진-6-카복실레이트를 수득하고, 수득된 일반식(Ⅲ) 화합물을 가수분해하여 상응하는 일반식(Ⅳ)의 산을 생성시킨 다음 산화시켜 일반식(V)의 설폭사이드를 얻고, 일반식(V)의 화합물에 대해 피폐라진 형태의 아민을 사용하여 친핵성치환반응을 수행하여 일반식(Ⅵ)의 생성물을 수득한 다음, 치환된 생성물을 환원시켜 상응하여 일반식(Ⅶ)의 티오에테르를 수득함을 특징으로 하여, 일반식(I)의 피리도-벤조티아진 유도체를 제조하는 방법.상기 식에서, R은 H 또는 CH3이고; n은 0,1 또는 2이며; Y는 Cl 또는 F, (여기세서 R1은 C1-C6알킬, C2-C6알케닐, 아릴알킬, 아릴알킬카보닐, 알킬카보닐 또는 알킬옥시카보닐이고, 이들은 할로겐 또는 할로드록시로 치환될 수 있다)이다.
- 제1항에 있어서, 제1단계 반응이, 3-클로로-4-플루오로아닐린을 칼륨 티오시아네이트와 브롬으로 처리하여 구조식(XII)의 생성물을 얻고, 수득된 화합물(XⅡ)을 NaOH로 처리하여 구조식(XⅢ)의 디설파이드를 생성시킨 다음, 이를 모노클로로아세톤 및 KOH로 처리하고, 계속해서 EtOH 중에서 NaBH4로 처리하여 일반식(Ⅱ)의 7-플루오로-8-클로로-3,4-디하이드로-3-메틸-2H-1,4-벤조티아진을 수득하고 단계로 이루어진 방법.상기 식에서, Y는 Cl이고, R은 CH3이다.
- 제1항에 있어서, 제1단계 반응이, 3-클로로-4-플루오로아닐린을 칼륨 티오시아네이트와 브롬으로 처리하여 수득된 구조식(XII)의 생성물을 NaOH로 처리하여 구조식(XIII)의 디설파이드를 얻은 다음, 이를나트륨 모노클로로아세테이드로 처리하고, 계속해서 THF 중의 LiAlH4로 처리하여 일반식(II)의 7-플루오로-8-클로로-3,4-디하이드로-2H-1,4-벤조티아진을 수득하는 단계로 이루어지는 방법.상기 식에서, Y는 Cl이고, R는 H이다.
- 제1항에 있어서, 제1단게 반응이 3-클로로-4-플루오로아닐린을 칼륨 설포시아네이트와 브롬으로 처리하여 구조식(Ⅶ)의 화합물을 수득한 다음, 수득된 구조식(XII)의 화합물을 NaOH로 처리하여 구조식(XⅢ)의 디설파이드를 수득하고, 이를 1-브로모-2-클로로에탄 또는 1,2-디클로로프로판으로 처리하여 일반식(Ⅱ)의 7-플루오로-8-클로로-3,4-디하이드로-2H-1,4-벤조티아진을 수득하는 단계로 이루어지는 방법.상기 식에서, Y는 Cl이고, R은 H 또는 CH3이다.
- 제1항에 있어서, 제1단계의 반응이 2,3,4-트리플루오로니트로벤젠을 Na2S로 처리하여 구조식(Ⅸ)의 디설파이드를 생성한 다음, 생성한 화합물을 철 분말 및 아세트산으로 처리하고, 계속해서 HCl로 처리하여 구조식(X)의 화합물을 수득한 후, 이를 모노클로로아세톤 및 KOH 로 처리하고, 이어서, EtOH 중에서 NaBH4로 처리하여 일반식(Ⅱ)의 7,8-디플루오로-3,4-디하이드로-3-메틸-2H-1,4-벤조티아진을 수득하는 단계로 이루어진 방법.상기 식에서, Y는 F이고, R은 CH3이다.
- 제1항에 있어서, 제1단계 반응이 2,3,4-트리플루오로니트로 벤젠을 Na2S로 처리하여 구조식(Ⅸ)의 디설파이드를 생성한 후, 이를 철분말 및 아세트산으로 처리하고, 계속해서 HCl로 처리하여 구조식(X)의 화합물을 수득한 다음, 수득된 화합물을 나트륨 모노클로로아세테이드로 처리하고, 이어서, THF 중에서 LiAlH4로 처리하여 일반식(Ⅱ)의 7,8-디플루오로-3,4-디하이드로-2H-1,4-벤조티아진을 수득하는 단게로 이루어진 방법.상기 식에서, Y는 F이고, R은 H이다.
- 제1항에 있어서, 일반식(Ⅱ) 화합물과 에틸에톡시메틸렌말로네이트와의 반응을 용매의 존재 또는 부재하에, 80 내지 160℃의 온도에서 수행하는 방법.
- 제1항에 있어서, 일반식(Ⅳ) 화합물의 산화반응을 아세트산 매질중, 조정된 온도에서 테트라아세트산 납 또는 과산화수소를 사용하여 수행하는 방법.
- 제1항에 있어서, 친핵성 치환반응을 비극성, 비양자성 유기용매중 또는 극성, 비양자성 유기용매중, 70° 내지 160℃의 온도에서 수행하는 방법.
- 제1항에 있어서, 일반식(Ⅵ) 화합물의 환원반응을 디메틸포름아미드중, 5℃ 이하의 온도에서 삼브롬화인으로 처리하여 수행하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT19790/84A IT1173374B (it) | 1984-02-24 | 1984-02-24 | Derivati pirido-benzotiazinici ad elevata attivita' antimicrobica |
| IT19790A/84 | 1984-02-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR850006426A true KR850006426A (ko) | 1985-10-05 |
| KR880000024B1 KR880000024B1 (en) | 1988-02-15 |
Family
ID=11161233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8501180A KR880000024B1 (en) | 1984-02-24 | 1985-02-23 | Process for preparing pyrido-benzothiazine derivatives |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US4668784A (ko) |
| EP (1) | EP0165375B1 (ko) |
| JP (2) | JPS60208987A (ko) |
| KR (1) | KR880000024B1 (ko) |
| AT (1) | ATE57532T1 (ko) |
| AU (1) | AU573780B2 (ko) |
| CA (1) | CA1340554C (ko) |
| DE (1) | DE3580124D1 (ko) |
| DK (1) | DK81885A (ko) |
| EG (1) | EG17585A (ko) |
| ES (3) | ES8801923A1 (ko) |
| FI (1) | FI83327C (ko) |
| GR (1) | GR850482B (ko) |
| IE (1) | IE57974B1 (ko) |
| IT (1) | IT1173374B (ko) |
| MX (5) | MX172473B (ko) |
| NO (1) | NO171163C (ko) |
| NZ (1) | NZ211224A (ko) |
| PH (2) | PH22239A (ko) |
| PT (1) | PT80003B (ko) |
| YU (1) | YU43401B (ko) |
| ZA (1) | ZA851379B (ko) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2358580A1 (fr) * | 1976-07-16 | 1978-02-10 | Comet | Perfectionnements aux cages pour ecrous prisonniers et aux appareils et procedes pour fabriquer de telles cages |
| IT1196429B (it) * | 1986-07-01 | 1988-11-16 | Mediolanum Farmaceutici Srl | Processo per la preparazione di pirido benzotiazine ad attivita' antibatterica e loro sali con acidi solfonici |
| IT1197841B (it) * | 1986-10-14 | 1988-12-06 | Mediolanum Farmaceutici Srl | Derivati pirido-benzotiazinici ad attivita' antibatterica ed a lunga durata di azione |
| IT1222833B (it) * | 1987-10-06 | 1990-09-12 | Mediolanum Farmaceutici Srl | Derivati pirido benzotiazinici dotati di elevata attivita' antibatterica e di elevata biodisponibilita' tissutale |
| US4840525A (en) * | 1987-12-09 | 1989-06-20 | Unistrut International Corp. | Fastener restrainer for framing system |
| DE3906365A1 (de) * | 1988-07-15 | 1990-01-18 | Bayer Ag | 7-(1-pyrrolidinyl)-3-chinolon- und -naphthyridoncarbonsaeure-derivate, verfahren sowie substituierte (oxa)diazabicyclooctane und -nonane als zwischenprodukte zu ihrer herstellung, und sie enthaltende antibakterielle mittel und futterzusatzstoffe |
| US5308843A (en) * | 1990-09-11 | 1994-05-03 | Sterling Drug Inc. | Method of inhibiting mammalian topoisomerase II and malignant cell growth in mammals, with substituted (S)-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4 ]-benzoxazine(and-benzothiazine)-6-carboxylic acids |
| IT1248011B (it) * | 1991-06-07 | 1995-01-05 | Mediolanum Farmaceutici Spa | Procedimento per la preparazione dell'acido 9-fluoro-10- (4-metil-1-piperazinil)-7-oxo-2,3-diidro-7h-pirido (1,2,3-de) (1,4)benzotiadin-6-carbossilico cloridrato. |
| US5532239A (en) * | 1993-08-02 | 1996-07-02 | Assistance Publique - Hopitaux De Paris | Therapeutic application of fluoroquinolone derivatives |
| IT1270834B (it) * | 1993-10-27 | 1997-05-13 | Archimica Spa | Disolfuro chinolico |
| JP2003527308A (ja) | 1998-12-04 | 2003-09-16 | インフラックス，インコーポレイテッド | 多剤輸送体の阻害剤 |
| US6262072B1 (en) | 1999-10-12 | 2001-07-17 | Yung Shin Pharmaceutical Industrial Co. Ltd. | Orally administered antimicrobial pharmaceutical formulations of ciprofloxacin |
| SE9904108D0 (sv) | 1999-11-15 | 1999-11-15 | New Pharma Research Ab | Nya föreningar |
| KR100440192B1 (ko) * | 2001-11-22 | 2004-07-12 | 이수화학 주식회사 | 광학 활성 퀴놀론카르복실산 유도체의 제조방법 |
| US6957105B2 (en) * | 2002-03-26 | 2005-10-18 | Cardiac Pacemakers, Inc. | Method and apparatus for detecting oscillations in cardiac rhythm with electrogram signals |
| US7973022B2 (en) * | 2006-02-17 | 2011-07-05 | Idexx Laboratories, Inc. | Fluoroquinolone carboxylic acid salt compositions |
| US20070196398A1 (en) * | 2006-02-17 | 2007-08-23 | Murthy Yerramilli V S | Fluoroquinolone fatty acid salt compositions |
| US20070197548A1 (en) * | 2006-02-17 | 2007-08-23 | Murthy Yerramilli V S | Fluoroquinolone compositions |
| WO2013076590A1 (en) * | 2011-11-23 | 2013-05-30 | Oxygen Healthcare Research Pvt. Ltd | Benzothiazine compounds as h3 receptor ligands |
| DE102013101756A1 (de) | 2012-11-30 | 2014-06-05 | Hamberger Industriewerke Gmbh | Verbindung und Verriegelungselement |
| DE102013108539A1 (de) | 2013-08-07 | 2015-02-12 | Hamberger Industriewerke Gmbh | Verbindung und Verriegelungselement |
| DE102013108538A1 (de) | 2013-08-07 | 2015-02-12 | Hamberger Industriewerke Gmbh | Verbindung und Verriegelungselement |
| DE102015106035A1 (de) | 2014-07-31 | 2016-02-04 | Hamberger Industriewerke Gmbh | Verbindung für plattenförmige Bauelemente und Feder |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57203085A (en) * | 1981-06-09 | 1982-12-13 | Dai Ichi Seiyaku Co Ltd | 1,8-cyclic substituted quinoline derivative |
| JPS5976091A (ja) * | 1982-10-22 | 1984-04-28 | Otsuka Pharmaceut Co Ltd | ピリド〔１，２，３−ｄｅ〕〔１，４〕ベンゾチアジン誘導体 |
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1984
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1985
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