KR860002490A - 2,3-디히드로벤조푸란-5-설폰아미드 유도체의 제조방법 - Google Patents
2,3-디히드로벤조푸란-5-설폰아미드 유도체의 제조방법 Download PDFInfo
- Publication number
- KR860002490A KR860002490A KR1019850006459A KR850006459A KR860002490A KR 860002490 A KR860002490 A KR 860002490A KR 1019850006459 A KR1019850006459 A KR 1019850006459A KR 850006459 A KR850006459 A KR 850006459A KR 860002490 A KR860002490 A KR 860002490A
- Authority
- KR
- South Korea
- Prior art keywords
- lower alkyl
- group
- general formula
- hydrogen
- different
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 3
- YSWWLKULIVOPEP-UHFFFAOYSA-N 2,3-dihydro-1-benzofuran-5-sulfonimidic acid Chemical class NS(=O)(=O)C1=CC=C2OCCC2=C1 YSWWLKULIVOPEP-UHFFFAOYSA-N 0.000 title claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 238000010511 deprotection reaction Methods 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 229940126062 Compound A Drugs 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- 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
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (3)
- 하기 일반식(Ⅱ), 필요하다면 보호시킨 유도체의, 5-위치를 클로로설폰화하여 하기 일반식(Ⅲ)의 5-클로로설포닐 화합물을 수득하고, 일반식(Ⅲ) 화합물을 일반식(Ⅳ)의 암모니아, 아민 또는 카르바민산 유도체와 반응시킨후 필요하다면 탈보호 및/또는 변형시킴을 특징으로 하는 하기 일반식(Ⅰ)의 2,3-디히드로벤조 푸란-5-설폰아미드의 제조방법.[상기식중, R1및 R2는 서로 같거나 다르고, 각각 수소, 저급알킬, 4-~7-원 시클로알킬, 치환된 또는 비치환 된 페닐, 페닐(저급 알킬), 저급 알콕시카르보닐 또는 모르폴리노(저급 알킬)이고; 또는 R1및 R2는 인접한 질소원자와 함께 고리를 형성하여 1개 또는 그 이상의 첨가된 이형원자를 갖는 치환된 또는 비치환된 5-또는 6-원 복소환을 형성할 수도 있으며, R3는 COR4또는 CH2R5기이고, R4는 히드록시 또는 OR6또는 NR7R8기이며, R5는 히드록시, 저급알콕시, 저급 지방족 아실옥시 또는 할로겐원자이고, R5는 저급 알킬, 아릴, 카르복시메틸 또는 그의 에스테르, 히드록시메틸 또는 그의 지방족 아실레이트, 또는 1-프탈리딜이며, R7및 R8은 서로 같거나 다르고, 각각 수소 또는 저급 알킬이고 및 X 및 X′는 서로 같거나 다르고, 각각 수소 또는 할로겐원자이다.]
- 제1항에 있어서, R3가 COR4기이고 R4가 OR6기이며, 및 R6가 저급 알킬기일 경우에 상기 탈보호가 에스테르의 가수분해인 방법.
- 제1항에 있어서, R3가 -COOH 기일 경우에는 상기 변형이 상기 탈보호의 뒤이은 에스테르화인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP186971/1984 | 1984-09-05 | ||
JP59186971A JPS6163671A (ja) | 1984-09-05 | 1984-09-05 | 2,3−ジヒドロベンゾフラン−5−スルホンアミド誘導体および降圧利尿剤 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR860002490A true KR860002490A (ko) | 1986-04-26 |
KR930002100B1 KR930002100B1 (ko) | 1993-03-26 |
Family
ID=16197928
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019850006459A KR930002100B1 (ko) | 1984-09-05 | 1985-09-04 | 2, 3-디히드로벤조푸란-5-설폰아미드 유도체의 제조방법 |
Country Status (15)
Country | Link |
---|---|
US (1) | US4659709A (ko) |
EP (1) | EP0173899B1 (ko) |
JP (1) | JPS6163671A (ko) |
KR (1) | KR930002100B1 (ko) |
AT (1) | ATE70534T1 (ko) |
AU (1) | AU592060B2 (ko) |
CA (1) | CA1265800A (ko) |
DE (1) | DE3584919D1 (ko) |
DK (1) | DK165954C (ko) |
GB (1) | GB2164039B (ko) |
IE (1) | IE58911B1 (ko) |
NO (1) | NO169487C (ko) |
NZ (1) | NZ213197A (ko) |
PT (1) | PT81033B (ko) |
ZA (1) | ZA856277B (ko) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5116874A (en) * | 1985-09-23 | 1992-05-26 | Eli Lilly And Company | Anti-tumor method and compounds |
JPH01100164A (ja) * | 1987-10-12 | 1989-04-18 | Shionogi & Co Ltd | スルファモイル−2−ベンゾフランカルボン酸誘導体 |
DE3861963D1 (de) * | 1987-12-24 | 1991-04-11 | Boehringer Mannheim Gmbh | Heterocyclisch substituierte alkylsulfonamide, verfahren zu ihrer herstellung sowie arzneimittel. |
GB9110636D0 (en) * | 1991-05-16 | 1991-07-03 | Glaxo Group Ltd | Chemical compounds |
US5254582A (en) * | 1992-02-05 | 1993-10-19 | Eli Lilly And Company | Antitumor compositions and methods |
US5387681A (en) * | 1992-08-19 | 1995-02-07 | Eli Lilly And Company | Synthesis of bicyclic aromatic sulfonic acids sulfonyl chlorides and sulfonamides |
US6150402A (en) * | 1994-08-15 | 2000-11-21 | Loma Linda University Medical Center | Natriuretic compounds |
DE10135499A1 (de) * | 2001-07-20 | 2003-01-30 | Merck Patent Gmbh | Indanverbindungen mit negativem Delta-epsilon |
US7795242B2 (en) * | 2003-10-15 | 2010-09-14 | The Brigham And Women's Hospital, Inc. | Methods and compositions for immunomodulation |
EP1805158B1 (en) | 2004-10-29 | 2018-06-27 | Kalypsys, Inc. | Sulfonyl-substituted bicyclic compounds as modulators of ppar |
WO2007051095A1 (en) | 2005-10-25 | 2007-05-03 | Kalypsys, Inc. | Salts of modulators of ppar and methods of treating metabolic disorders |
US20080176861A1 (en) | 2007-01-23 | 2008-07-24 | Kalypsys, Inc. | Sulfonyl-substituted bicyclic compounds as ppar modulators for the treatment of non-alcoholic steatohepatitis |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU6004073A (en) * | 1972-09-09 | 1975-03-06 | Basf Ag | Fluorescent benzofuran compounds |
US4401669A (en) * | 1978-01-27 | 1983-08-30 | Merck & Co., Inc. | 2,3-Dihydro-substituted-5-benzoyl benzofuran-2-carboxylic acids and their use in treating hypertension |
CA1145758A (en) * | 1979-05-16 | 1983-05-03 | Shell Canada Limited | 2,3-dihydro-2-benzofurancarboxamide derivatives |
US4237130A (en) * | 1979-06-21 | 1980-12-02 | Merck & Co., Inc. | 2,3-Dihydro-6,7-disubstituted-5-(substituted sulfonyl)benzofuran-2-carboxylic acids |
DE3317884A1 (de) * | 1983-05-17 | 1984-11-22 | Hoechst Ag, 6230 Frankfurt | 5-(4-chlor-3-sulfamoylbenzoyl)-2,3-dihydro-2-benzofurancarbonsaeuren und verfahren zu ihrer herstellung |
US4544667A (en) * | 1984-02-09 | 1985-10-01 | Merck & Co., Inc. | 2-Sulfamoylbenzo[b]furan derivatives for the treatment of elevated intraocular pressure |
-
1984
- 1984-09-05 JP JP59186971A patent/JPS6163671A/ja active Granted
-
1985
- 1985-08-12 US US06/764,785 patent/US4659709A/en not_active Expired - Lifetime
- 1985-08-13 CA CA000488588A patent/CA1265800A/en not_active Expired - Fee Related
- 1985-08-15 AU AU46215/85A patent/AU592060B2/en not_active Ceased
- 1985-08-16 DE DE8585110250T patent/DE3584919D1/de not_active Expired - Fee Related
- 1985-08-16 AT AT85110250T patent/ATE70534T1/de not_active IP Right Cessation
- 1985-08-16 EP EP85110250A patent/EP0173899B1/en not_active Expired - Lifetime
- 1985-08-19 ZA ZA856277A patent/ZA856277B/xx unknown
- 1985-08-22 NZ NZ213197A patent/NZ213197A/xx unknown
- 1985-08-27 PT PT81033A patent/PT81033B/pt not_active IP Right Cessation
- 1985-09-02 NO NO853441A patent/NO169487C/no unknown
- 1985-09-04 IE IE218885A patent/IE58911B1/en not_active IP Right Cessation
- 1985-09-04 GB GB08521967A patent/GB2164039B/en not_active Expired
- 1985-09-04 KR KR1019850006459A patent/KR930002100B1/ko not_active IP Right Cessation
- 1985-09-04 DK DK403185A patent/DK165954C/da not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
NO169487B (no) | 1992-03-23 |
PT81033A (en) | 1985-09-01 |
GB8521967D0 (en) | 1985-10-09 |
US4659709A (en) | 1987-04-21 |
AU592060B2 (en) | 1990-01-04 |
ZA856277B (en) | 1986-04-30 |
JPH0354945B2 (ko) | 1991-08-21 |
IE58911B1 (en) | 1993-12-01 |
AU4621585A (en) | 1986-03-13 |
DK165954B (da) | 1993-02-15 |
EP0173899A3 (en) | 1988-07-20 |
GB2164039B (en) | 1988-05-18 |
EP0173899B1 (en) | 1991-12-18 |
NZ213197A (en) | 1989-01-06 |
NO853441L (no) | 1986-03-06 |
DK403185A (da) | 1986-03-06 |
PT81033B (pt) | 1987-09-18 |
KR930002100B1 (ko) | 1993-03-26 |
CA1265800A (en) | 1990-02-13 |
DK165954C (da) | 1993-07-05 |
EP0173899A2 (en) | 1986-03-12 |
DK403185D0 (da) | 1985-09-04 |
NO169487C (no) | 1992-07-01 |
GB2164039A (en) | 1986-03-12 |
JPS6163671A (ja) | 1986-04-01 |
IE852188L (en) | 1986-03-05 |
DE3584919D1 (de) | 1992-01-30 |
ATE70534T1 (de) | 1992-01-15 |
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