KR910009686A - 키랄 3,4-에폭시 벤조피란의 신규 제조 방법 - Google Patents
키랄 3,4-에폭시 벤조피란의 신규 제조 방법 Download PDFInfo
- Publication number
- KR910009686A KR910009686A KR1019900019429A KR900019429A KR910009686A KR 910009686 A KR910009686 A KR 910009686A KR 1019900019429 A KR1019900019429 A KR 1019900019429A KR 900019429 A KR900019429 A KR 900019429A KR 910009686 A KR910009686 A KR 910009686A
- Authority
- KR
- South Korea
- Prior art keywords
- benzopyran
- epoxy
- dihydro
- cyano
- dimethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 238000002360 preparation method Methods 0.000 title claims 3
- NGJMKTTXRCVYCG-UHFFFAOYSA-N 2h-oxireno[2,3-c]chromene Chemical compound C1=CC=C2C(O3)=C3COC2=C1 NGJMKTTXRCVYCG-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- HCYIWPLDKSWKGY-GHMZBOCLSA-N (1ar,7br)-2,2-dimethyl-1a,7b-dihydrooxireno[2,3-c]chromene-6-carbonitrile Chemical compound CC1(C)OC2=CC=C(C#N)C=C2[C@@H]2[C@H]1O2 HCYIWPLDKSWKGY-GHMZBOCLSA-N 0.000 claims 1
- HCYIWPLDKSWKGY-QWRGUYRKSA-N (1as,7bs)-2,2-dimethyl-1a,7b-dihydrooxireno[2,3-c]chromene-6-carbonitrile Chemical compound CC1(C)OC2=CC=C(C#N)C=C2[C@H]2[C@@H]1O2 HCYIWPLDKSWKGY-QWRGUYRKSA-N 0.000 claims 1
- KRZJRNZICWNMOA-GXSJLCMTSA-N (3s,4r)-4,8-dihydroxy-3-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2[C@@H](O)[C@@H](OC)CC(=O)C2=C1O KRZJRNZICWNMOA-GXSJLCMTSA-N 0.000 claims 1
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- -1 nitro, cyano, acetyl Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000004036 potassium channel stimulating agent Substances 0.000 claims 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (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)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Epoxy Compounds (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (10)
- 하기 일반식(D) 화합물:(상기식에서, NH2및 OH 부분은 트랜스이고, 각각(R,S) 또는 (S,R)이다.)의 사차 암모늄염의 염기 처리로 구성되는, 하기 일반식(A)′또는 (A)″화합물의 제조방법:
- 제1항에 있어서, Z이 산소인 방법.
- 제1항 또는 제2항에 있어서, R1이 치환체이고, R2가 수소인 방법.
- 제1항, 제2항 또는 제3항에 있어서, R3및 R4가 모두 메틸기인 방법.
- 제1항 내지 제4항중 어느 한 항에 있어서, R1이 니트로, 시아노, 아세틸, CF3,C2F5,OCF3,에틸,이소프로필 또는 시클로펜틸인 방법.
- 제1항 내지 제5항중 어느 한 항에 있어서, 일반식(A′)의 화합물 즉, (S,S)-이성체의 제조방법.
- 제1항에 있어서, (3S,4S)-6-시아노-3,4-디히드로-3,4-에폭시-2,2-디메틸-2H-1-벤조피란, (3R,4R)-6-시아노-3,4-디히드로-3,4-에폭시-2,2-디메틸-2H-1-벤조피란, 또는 (3S, 4S)-6-에틸-3,4-디히드로-3,4-에폭시-2,2-디메틸-2H-1-벤조피란의 제조방법.
- 제1항에 있어서, 사차 암모늄 염이 RL(이때, R은 C1-4알킬이고, L은 수소이다)로 형성된 것인 방법.
- 제8항에 있어서, RL이 CH3I인 방법.
- 제1항에 따라 제조된 것과 같이, 각각 일반식(A′)또는(A″)의 (3S,4S) 또는 (3R,4R) 에폭시드로부터 제조되는 (3S,4R) 또는 (4R,4S) 칼륨 통로 활성제 벤조피란.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB89269930 | 1989-11-29 | ||
GB898926993A GB8926993D0 (en) | 1989-11-29 | 1989-11-29 | Process |
GB909023300A GB9023300D0 (en) | 1990-10-25 | 1990-10-25 | Process |
GB90233008 | 1990-10-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
KR910009686A true KR910009686A (ko) | 1991-06-28 |
Family
ID=26296278
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019900019429A Ceased KR910009686A (ko) | 1989-11-29 | 1990-11-28 | 키랄 3,4-에폭시 벤조피란의 신규 제조 방법 |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP0430621A3 (ko) |
JP (1) | JPH03190878A (ko) |
KR (1) | KR910009686A (ko) |
AU (1) | AU633383B2 (ko) |
CA (1) | CA2030969A1 (ko) |
IE (1) | IE904278A1 (ko) |
NZ (1) | NZ236228A (ko) |
PT (1) | PT96023B (ko) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3936616A1 (de) * | 1989-11-03 | 1991-05-08 | Merck Patent Gmbh | Verfahren zur enantiomerentrennung von benzopyranderivaten |
US5573758A (en) * | 1995-04-28 | 1996-11-12 | Allergan | Method for reducing intraocular pressure in the mammalian eye by administration of potassium channel blockers |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0076075B1 (en) * | 1981-09-25 | 1986-11-20 | Beecham Group Plc | Pharmaceutically active benzopyran compounds |
DE3811017A1 (de) * | 1988-03-31 | 1989-10-19 | Hoechst Ag | Ungesaettigte n-benzopyranyllactame |
EP0346724A1 (de) * | 1988-06-16 | 1989-12-20 | MERCK PATENT GmbH | Chromanderivate |
GB8924373D0 (en) * | 1989-10-30 | 1989-12-20 | Beecham Group Plc | Novel compounds |
DE3936616A1 (de) * | 1989-11-03 | 1991-05-08 | Merck Patent Gmbh | Verfahren zur enantiomerentrennung von benzopyranderivaten |
-
1990
- 1990-11-26 EP EP19900312831 patent/EP0430621A3/en not_active Withdrawn
- 1990-11-27 NZ NZ236228A patent/NZ236228A/en unknown
- 1990-11-27 IE IE427890A patent/IE904278A1/en unknown
- 1990-11-27 CA CA002030969A patent/CA2030969A1/en not_active Abandoned
- 1990-11-27 AU AU66978/90A patent/AU633383B2/en not_active Ceased
- 1990-11-28 KR KR1019900019429A patent/KR910009686A/ko not_active Ceased
- 1990-11-28 PT PT96023A patent/PT96023B/pt not_active IP Right Cessation
- 1990-11-29 JP JP2333437A patent/JPH03190878A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
PT96023A (pt) | 1991-09-13 |
JPH03190878A (ja) | 1991-08-20 |
EP0430621A2 (en) | 1991-06-05 |
AU6697890A (en) | 1991-06-06 |
NZ236228A (en) | 1992-07-28 |
PT96023B (pt) | 1997-08-29 |
CA2030969A1 (en) | 1991-05-30 |
AU633383B2 (en) | 1993-01-28 |
IE904278A1 (en) | 1991-06-05 |
EP0430621A3 (en) | 1992-03-04 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19901128 |
|
PG1501 | Laying open of application | ||
A201 | Request for examination | ||
PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 19951128 Comment text: Request for Examination of Application Patent event code: PA02011R01I Patent event date: 19901128 Comment text: Patent Application |
|
E902 | Notification of reason for refusal | ||
PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 19980421 Patent event code: PE09021S01D |
|
E601 | Decision to refuse application | ||
PE0601 | Decision on rejection of patent |
Patent event date: 19980626 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 19980421 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |