KR890701571A - 4h-3, 1-벤즈옥사진-4-온 화합물 및 세린 프로테아제 억제를 위한 그의 약학 조성물 - Google Patents
4h-3, 1-벤즈옥사진-4-온 화합물 및 세린 프로테아제 억제를 위한 그의 약학 조성물Info
- Publication number
- KR890701571A KR890701571A KR1019890700225A KR890700225A KR890701571A KR 890701571 A KR890701571 A KR 890701571A KR 1019890700225 A KR1019890700225 A KR 1019890700225A KR 890700225 A KR890700225 A KR 890700225A KR 890701571 A KR890701571 A KR 890701571A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- compound
- general formula
- represented
- amino acid
- Prior art date
Links
- -1 4H-3, 1-benzoxazin-4-one compound Chemical class 0.000 title claims 10
- 108010022999 Serine Proteases Proteins 0.000 title claims 3
- 102000012479 Serine Proteases Human genes 0.000 title claims 3
- 239000008194 pharmaceutical composition Substances 0.000 title claims 2
- 230000005764 inhibitory process Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000000539 amino acid group Chemical group 0.000 claims 5
- 125000006239 protecting group Chemical group 0.000 claims 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 1
- 239000004471 Glycine Substances 0.000 claims 1
- 101000851058 Homo sapiens Neutrophil elastase Proteins 0.000 claims 1
- SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 claims 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 1
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 claims 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 1
- SNDPXSYFESPGGJ-UHFFFAOYSA-N L-norVal-OH Natural products CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 claims 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- 102100033174 Neutrophil elastase Human genes 0.000 claims 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 235000004279 alanine Nutrition 0.000 claims 1
- 235000003704 aspartic acid Nutrition 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 235000013922 glutamic acid Nutrition 0.000 claims 1
- 239000004220 glutamic acid Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 1
- 229960000310 isoleucine Drugs 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 1
- 102000004196 processed proteins & peptides Human genes 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 239000004474 valine Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/20—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 4
- C07D265/22—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
- C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 하기일반식(Ⅰ)의 4H-3,1-벤즈옥사진-4-온 화합물 및 그의염.식중, R은 수소원자 및 알킬기로 구성되는 군에서 선택된 것이고, A는 아미노산 잔기 및 2내지 3개의 아미노산 잔기를 갖는 팹티드로 구성되는 군에서 선택된 것이며, 이때 아미노산 잔기는 보호기에 의해 보호된 곁사슬을 가질수 있고, X는 알킬기, 플루오로알킬기, R1이 알킬기를 나타내는 OR1기 및 NHR1기로 구성되 는 군에서 선택된 것이며, Y는 아미노기를 위한 보호기이다.
- 제1항에 있어서, 일반식(Ⅰ)에서 A로 표시되는 아미노산 잔기 또는 펩티드에 함유된 아미노산 잔기가 알라닌, 글리신, 이소로이신, 로이신, 페닐알라닌, 프롤린, 발린, 노르발린, 노르로이신, 페닐글리신, 카르보벤즈옥시기로 보호된 ε-아미노기를 갖는 리신, 벤질 에스테르의 형태로 보호된 β-카르복실기를 갖는 아스파르트산, 벤질 에스테르의 형태로 보호된 γ-카르복실기를 갖는 글루탐산으로 구성되는 군에서 선택되는 화합물.
- 제1항에 있어서, 일반식(Ⅰ)에서 Y로 표시되는 아미노기의 보호기가 카르보벤즈옥시, t-부톡시카르보닐 및 아세틸기로 구성되는 군에서 선택되는 화합물.
- 제1항에 있어서, 일반식(Ⅰ)에서 R로 표시되는 알킬기가 메틸및 에틸기로 구성되는 군에서 선택된 화합물.
- 제1항에 있어서, 일반식(Ⅰ)에서 X로 표시되는 알킬기가 메틸, 에틸, 프로필, 이소프로필, 부틸 및 이소부틸기로 구성되는 군에서 선택되는 화합물.
- 제1항에 있어서, 일반식(Ⅰ)에서 X로 표시되는 플루오로알킬기가 트리플루오로메틸기인 화합물.
- 제1항에 있어서, 일반식(Ⅰ)에서 X로 표시되는 OR1기가 메톡시, 에톡시, 프로폭시, 이소프로폭시, 부톡시 및 이소부톡시기로 구성되는 군에서 선택되는 화합물.
- 제1항에 있어서, 일반식(Ⅰ)에서 X로 표시되는 NHR1기가 모노메틸아미노, 모노에틸아미노, 모노프로필아미노, 모노이소프로필아미노, 모노부틸아미노 및 모노이소부틸아미노기로 구성되는 군에서 선택되는 화합물.
- 제1항에 있어서, 언급된 일반식(Ⅰ)의 4H-3,1-벤즈옥사진-4-온 화합물 또는 그의 약학적으로 허용되는 비 유독성염의 약학적 유효량 및 그의 약학적으로 허용되는 담체의 혼합물로 이루어지는, 세린 프로테아제의 억제를 약학 조성물.
- 제9항에 있어서, 세린 프로테아제가 인간의 백혈구 엘라스타아제인 조성물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62-142364 | 1987-06-09 | ||
| JP14236487 | 1987-06-09 | ||
| JP63-102404 | 1988-04-27 | ||
| JP10240488 | 1988-04-27 | ||
| PCT/JP1988/000556 WO1988009790A1 (en) | 1987-06-09 | 1988-06-09 | 4h-3,1-benzoxazin-4-one compounds and serine protease-inhibiting medicinal composition containing same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR890701571A true KR890701571A (ko) | 1989-12-21 |
| KR910001131B1 KR910001131B1 (ko) | 1991-02-25 |
Family
ID=26443119
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019890700225A KR910001131B1 (ko) | 1987-06-09 | 1988-06-09 | 4h-3,1-벤즈옥사진-4-온 화합물 및 세린 프로테아제 억제를 위한 그의 약학 조성물 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4980287A (ko) |
| EP (1) | EP0317645B1 (ko) |
| KR (1) | KR910001131B1 (ko) |
| AU (1) | AU616420B2 (ko) |
| CA (1) | CA1309556C (ko) |
| DE (1) | DE3884145T2 (ko) |
| DK (1) | DK57489D0 (ko) |
| WO (1) | WO1988009790A1 (ko) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU635403B2 (en) * | 1990-02-15 | 1993-03-18 | Teijin Limited | 4h-3,1-benzoxazin-4-one compound and elastase inhibitor composition containing the same |
| CA2056453A1 (en) * | 1990-03-30 | 1991-10-01 | Koji Kobayashi | 4h-3, 1-benzoxazin-4-one derivative |
| EP0533951A4 (en) * | 1991-04-10 | 1993-09-01 | Japan Tobacco Inc. | Novel oxazinone derivative |
| US5428021A (en) * | 1994-01-27 | 1995-06-27 | Sri International | Human leukocyte elastase (HLE) inhibitors, and related pharmaceutical compositions and methods of use |
| US5849741A (en) * | 1994-08-09 | 1998-12-15 | Eisai Co., Ltd. | Fused pyridazine compounds |
| US5693515A (en) * | 1995-04-28 | 1997-12-02 | Arris Pharmaceutical Corporation | Metal complexed serine protease inhibitors |
| US5985872A (en) | 1995-05-24 | 1999-11-16 | G.D. Searle & Co. | 2-amino-benzoxazinones for the treatment of viral infections |
| KR100460932B1 (ko) * | 1995-05-24 | 2005-02-28 | 지.디. 썰 엘엘씨 | 바이러스감염치료용2-아미노-벤조옥사진온 |
| AR022204A1 (es) * | 1999-01-08 | 2002-09-04 | Norgine Bv | Compuesto, proceso para su preparacion, composicion farmaceutica y producto comestible que lo comprende. |
| US6989369B2 (en) * | 2003-02-07 | 2006-01-24 | Dyax Corp. | Kunitz domain peptides |
| CA3151626A1 (en) * | 2019-10-01 | 2021-04-08 | Molecular Skin Therapeutics, Inc. | Benzoxazinone compounds as klk5/7 dual inhibitors |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH464926A (de) * | 1961-09-13 | 1968-11-15 | Robapharm Ag | Verfahren zur Herstellung von neuen Derivaten des 6-Amino-dihydro-1,3-benzoxazin-2,4-dions |
| NZ210669A (en) * | 1983-12-27 | 1988-05-30 | Syntex Inc | Benzoxazin-4-one derivatives and pharmaceutical compositions |
| JPS60169469A (ja) * | 1983-12-27 | 1985-09-02 | シンテツクス（ユ−・エス・エイ）インコ−ポレイテツド | ４ｈ−１，３−ベンズオキサジン−４−オン化合物 |
| US4657893A (en) * | 1984-05-09 | 1987-04-14 | Syntex (U.S.A.) Inc. | 4H-3,1-benzoxazin-4-ones and related compounds and use as enzyme inhibitors |
| US4665070A (en) * | 1985-06-25 | 1987-05-12 | Syntex (U.S.A.) Inc. | 2-oxy-4H-3,1-benzoxazin-4-ones and pharmaceutical use |
| JP3458400B2 (ja) * | 1993-01-29 | 2003-10-20 | 松下電器産業株式会社 | 電子楽器用鍵盤装置 |
-
1988
- 1988-06-07 CA CA000568827A patent/CA1309556C/en not_active Expired - Lifetime
- 1988-06-09 KR KR1019890700225A patent/KR910001131B1/ko not_active IP Right Cessation
- 1988-06-09 EP EP88905224A patent/EP0317645B1/en not_active Expired - Lifetime
- 1988-06-09 WO PCT/JP1988/000556 patent/WO1988009790A1/ja active IP Right Grant
- 1988-06-09 DE DE88905224T patent/DE3884145T2/de not_active Expired - Fee Related
- 1988-06-09 AU AU19377/88A patent/AU616420B2/en not_active Ceased
- 1988-06-09 US US07/340,097 patent/US4980287A/en not_active Expired - Fee Related
-
1989
- 1989-02-08 DK DK057489A patent/DK57489D0/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0317645A4 (en) | 1989-10-04 |
| AU616420B2 (en) | 1991-10-31 |
| EP0317645A1 (en) | 1989-05-31 |
| DK57489A (da) | 1989-02-08 |
| WO1988009790A1 (en) | 1988-12-15 |
| DK57489D0 (da) | 1989-02-08 |
| US4980287A (en) | 1990-12-25 |
| DE3884145T2 (de) | 1994-01-13 |
| CA1309556C (en) | 1992-10-27 |
| KR910001131B1 (ko) | 1991-02-25 |
| AU1937788A (en) | 1989-01-04 |
| DE3884145D1 (de) | 1993-10-21 |
| EP0317645B1 (en) | 1993-09-15 |
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