KR890017246A - 크로만 유도체 - Google Patents

크로만 유도체 Download PDF

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KR890017246A
KR890017246A KR1019890006017A KR890006017A KR890017246A KR 890017246 A KR890017246 A KR 890017246A KR 1019890006017 A KR1019890006017 A KR 1019890006017A KR 890006017 A KR890006017 A KR 890006017A KR 890017246 A KR890017246 A KR 890017246A
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oxy
formula
chroman
cyano
trimethyl
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KR1019890006017A
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KR0150781B1 (ko
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케리케 랄프
바움가르드 맨프레트
루에스 인게보르그
베르그만 랄프
드 페이어 자퀴스
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나우만, 호이만
메르크 파텐트 게젤샤프트 미트 베슈랭크터 하프둥
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Priority claimed from DE3835011A external-priority patent/DE3835011A1/de
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    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07ORGANIC CHEMISTRY
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    • C07D407/00Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/04Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00Drugs for disorders of the muscular or neuromuscular system
    • A61P21/02Muscle relaxants, e.g. for tetanus or cramps
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/12Antihypertensives
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    • C07D311/02Heterocyclic 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
    • C07D311/04Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
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    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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Abstract

내용 없음

Description

크로만 유도체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 일반식(I)의 크로만 유도체 및 그의 염.
    상기식에서 R1과 R8는 각각 A이고, R2는 H 또는 A이고, R1과 R2는 모두 3-6 탄소원자를 지닌 알킬렌이고, R3는 OH 또는 OAc이고, R4는 수소이고, R3와 R4는 각각 결합이고, R5는 A, F, Cl, Br, J, OH, OA, OAc, NO2, NH2, AcNH, HOOC 및/또는 AOOC가 하나 또는 둘 치환되어 있거나 치환되지 않은 피리딜-옥시, 피리다진일-옥시, 피리미딘일-옥시, 피라진일-옥시, 옥시-디히드로-피리닐-옥시, 옥소-디히드로-피라다진일-옥시, 옥소-디히드로-피리미딘일-옥시, 옥소-디히드로-피라진일-옥시, 1H-2-피리돈-1-일, 1H-6-피리다진온-1-일, 1H-2-피리미딘온-1-일, 1H-6-피리미딘온-1-일, 1H-2-피라진온-1-일, 3H- 또는 5H-2-피롤린온-1-일 또는 1H-2-티오피리돈-1-일 등의 치환기를 말하면 이들은 전체적 또는 부분적으로 수소화 되어 있다. R6와 R7은 각각 H, A, HO, AO, CHO, ACO, ACS, HOOC, AOOC, AO-CS, ACOO, A-CS-O, 1-6탄소원자를 지닌 히드록시알킬, 1-6 탄소원자를 지닌 머르캅토알킬, NO2,NH2,NHA,NA2,CN,F,Cl,Br,I,CF3,ASO,ASO2AOSO,AOSO2,AcNH,AOCONH,H2NSO,HANSO,A2NSO,H2NSO2,HANSO2,A2NSO2,H2NCO,HANCO,A2NCO,H2NCS,HANCS,A2NCS,ASONH,ASO2NH,AOSONH,AOSO2NH,ACO-알킬, 니트로알킬, 시아노일킬, A-C(=NOH) 또는 A-C(=NNH2)이고, A는 1-6 탄소원자를 지닌 알킬이고, 알킬은 1-6 탄소원자를 지닌 알킬렌이고, Ac는 1-8 탄소원자를 지닌 알칸오일 또는 7-11 탄소원자를 지닌 아로일이다.
  2. a) 2,2,3-트리메틸-4-(1H-2-피리돈-1-일)-6-시아노-크로만-3-올. b) 2,2,3-트리메틸-4-(1H-2-피리돈-1-일)-6-시아노-2H-크로만. c) 2,2,3-트리메틸-4-(2-히드록시-피라딜-옥시)-6-시아노-크로만-3-올. d) 2,2,3-트리메틸-4-(6-히드록시-3-피리다진일-옥시)-6-시아노-크로만-3-올. e) 2,2,3-트리메틸-4-(1,5-디히드로-1메틸-6-옥소-3-피리다진일-옥시)-6-시아노-크로만-3-올. f) 2,2,3-트리메틸-4-(1,6-디히드로-1-에틸-6-옥소-3-피리다진일-옥시)-6-시아노-크로만-3-올. g) 2,2,3-트리메틸-4-(2-피롤리돈-1-일)-6-옥소-3-피리다진일-옥시)-6-시아노-크로만-3-올. h) 2,2,3-트리메틸-4-(2-피롤리돈-1일)-6-옥소-3-피리다진-일-옥시)-6-시아노-2H-크로만.
  3. 일반식(Ⅱ)의 3,4-에폭시크로만을 일반식(Ⅱ)의 화합물 또는 이의 반응성 유도체중 하나와 반응시키고/시키거나 R3가 OH이고 R4가 수소인 일반식(I)의 화합물을 탈수하고/하거나, 일반식(I)에 있어서 R3,R5,R6및/또는 R7의 치환기중 하나 이상을 다른 R3,R5,R6및/또는 R7의 치환기로 전환 시키고/시키거나, 일반식(I)의 염기성 화합물을 산으로 처리하여 그의 산부가염증 하나로 전환시킴을 특징으로 하는 일반식(I)의 크로만 유도체의 제조방법.
    상기식에서 R5,R6,R7및 R8은 제1항의 주어진 의미와 같다.
  4. 일반식(I)의 화합물 및/또는 그의 생리학적으로 허용될 수 있는 염을 투여에 적합하도록 적어도 하나 이상의 고형, 액체형 또는 반고형의 부형제 또는 보호제와 혼합하거나 하나 이상의 다른 활성 화합물과 혼합물을 특징으로 하는 약제학적 제제의 제조방법.
  5. 적어도 하나 이상의 일반식(I)의 화합물 및/또는 그의 생리학적으로 허용될 수 있는 염을 포함하는 약제학적 제제.
  6. 질병 치료용으로서의 일반식(I)의 화합물.
  7. 일반식(I)의 화합물의 의약제조용으로의 용도.
  8. 일반식(I)의 화합물의 질병치료 용도.
  9. 일반식(Ⅳ)의 화합물.
    상기식에서, -X,Y-은 (a) -CO-CH2-, (b) -CO-CR10, (c) -CHOH-CHR8-, (d) -CH=CR8- (e)이고, R9는 CHO,ACO,AOOC,NO2,CN,Br,H2NCO 또는 NSS이고 R10은 탄소수 1-6의 알킬디엔이고, R1과 R2는 제1항의 주어진 바와 같다.
  10. a) 2,2-디메틸-6-시아노-크로만-4-온. b) 2,2,3-트리메틸-3,4-에폭시-시아노-크로만.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019890006017A 1988-05-06 1989-05-04 크로만 유도체 KR0150781B1 (ko)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE3815504A DE3815504A1 (de) 1988-05-06 1988-05-06 4-n-heterocyclyl-chromanderivate, verfahren sowie zwischenprodukte zu ihrer herstellung und ihre verwendung in arzneimitteln
DEP3815504.4 1988-05-06
DE3835011A DE3835011A1 (de) 1988-10-14 1988-10-14 Chromanderivate
DEP3835011.4 1988-10-14

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KR890017246A true KR890017246A (ko) 1989-12-15
KR0150781B1 KR0150781B1 (ko) 1998-10-15

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US (1) US5013853A (ko)
EP (1) EP0340718B1 (ko)
JP (1) JPH01319481A (ko)
KR (1) KR0150781B1 (ko)
AR (1) AR246966A1 (ko)
AT (1) ATE108786T1 (ko)
AU (1) AU628331B2 (ko)
DE (1) DE58908062D1 (ko)
DK (1) DK223289A (ko)
ES (1) ES2057010T3 (ko)
FI (1) FI93358C (ko)
HU (1) HU207311B (ko)
IE (1) IE63794B1 (ko)
IL (1) IL90198A (ko)
NO (1) NO174467C (ko)
NZ (1) NZ228991A (ko)
PT (1) PT90471B (ko)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5387587A (en) * 1986-12-23 1995-02-07 Merck Patent Gesellschaft Mit Beschrankter Haftung Chroman derivatives
DE3835011A1 (de) * 1988-10-14 1990-04-19 Merck Patent Gmbh Chromanderivate
US5284838A (en) * 1987-06-23 1994-02-08 Elf Sanofi Use of 2,2-dimethylchroman-3-ol derivatives in the treatment of asthma
JPH03500542A (ja) * 1988-05-09 1991-02-07 ビーチャム グループ ピーエルシー 新規な化合物及び治療法
EP0346724A1 (de) * 1988-06-16 1989-12-20 MERCK PATENT GmbH Chromanderivate
DE3918041A1 (de) * 1989-06-02 1990-12-06 Merck Patent Gmbh Chromanderivate
DE3923839A1 (de) * 1989-07-19 1991-01-31 Beiersdorf Ag Benzopyran-derivate, verfahren zu ihrer herstellung und ihre verwendung sowie die verbindungen enthaltende zubereitungen
US5223629A (en) * 1989-07-21 1993-06-29 Alkaloida Vegyeszeti Gyar Process for the preparation of anti-hypertensive benzopyran
DE3924417A1 (de) * 1989-07-24 1991-01-31 Merck Patent Gmbh Chromanderivate
DE3936616A1 (de) * 1989-11-03 1991-05-08 Merck Patent Gmbh Verfahren zur enantiomerentrennung von benzopyranderivaten
DE4038752A1 (de) * 1990-12-05 1992-06-11 Merck Patent Gmbh Chromanderivate
NZ240933A (en) * 1990-12-21 1993-05-26 Ortho Pharma Corp Preparing enantiomerically pure thienopyran derivatives
US5332168A (en) * 1991-04-01 1994-07-26 Fuji Photo Film Co., Ltd. Photographic film cassette with improved separator claw
JP3442815B2 (ja) * 1992-05-13 2003-09-02 第一製薬株式会社 ジアザビシクロアルケン誘導体
WO1994008536A1 (en) * 1992-10-21 1994-04-28 Gynetech Laboratories, Inc. Vaginal sponge delivery system
GB9316111D0 (en) * 1993-08-04 1993-09-22 Pfizer Ltd Benzopyrans
US5837702A (en) * 1993-10-07 1998-11-17 Bristol-Myers Squibb Co. 4-arylamino-benzopyran and related compounds
EP0677519A4 (en) * 1993-11-10 1996-04-03 Japan Tobacco Inc CHROMAN DERIVATIVE AND THERAPEUTIC USE THEREOF.
US5869478A (en) * 1995-06-07 1999-02-09 Bristol-Myers Squibb Company Sulfonamido substituted benzopyran derivatives
US5612323A (en) * 1995-06-07 1997-03-18 Bristol-Myers Squibb Company Phosphinic ester substituted benzopyran derivatives
US5612370A (en) * 1995-06-07 1997-03-18 Bristol-Myers Squibb Company Phenylglycine and phenylalaninen amido benzopyran derivatives
US5629429A (en) * 1995-06-07 1997-05-13 Bristol-Myers Squibb Company Process for preparing 4-arylamino-benzopyran and related compounds
EP1218367A1 (en) * 1999-10-05 2002-07-03 Nissan Chemical Industries, Ltd. 4-oxybenzopyran derivative
FR2820974B1 (fr) * 2001-02-21 2004-02-13 Pharmascience Lab Composition topique comprenant une solution vraie contenant un derive de chromane ou de chromene, son procede de preparation et son utilisation cosmetique et therapeutique
JP2008523145A (ja) * 2004-12-13 2008-07-03 イーライ リリー アンド カンパニー リポキシゲナーゼ阻害剤としてのスピロ誘導体
US10981951B2 (en) 2014-01-31 2021-04-20 Mayo Foundation For Medical Education And Research Therapeutics for the treatment of glaucoma

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1077066A (en) * 1963-09-10 1967-07-26 Benger Lab Ltd Improvements in or relating to the synthesis of chromanones
US3467676A (en) * 1967-04-05 1969-09-16 American Home Prod 5-hydroxy-2,2,7-trialkylchroman-4-ones and derivatives
CH619701A5 (ko) * 1975-08-07 1980-10-15 Bayer Ag
DE2745305A1 (de) * 1977-10-07 1979-04-19 Bayer Ag Insektizide und akarizide mittel
DE2814983A1 (de) * 1978-04-07 1979-10-18 Bayer Ag Neue chromanon-derivate
JPS6047269B2 (ja) * 1978-04-14 1985-10-21 日産化学工業株式会社 クロマノ−ル類化合物およびその製造方法
US4241069A (en) * 1979-09-04 1980-12-23 Miles Laboratories, Inc. 3-Methylene flavanones and 3-methylene chromanones
GB2107706A (en) * 1981-09-25 1983-05-05 Beecham Group Plc Benzopyrans
US4486428A (en) * 1982-03-16 1984-12-04 Pfizer Inc. Bicyclic benzo fused compounds
EP0093535B1 (en) * 1982-04-28 1986-12-30 Beecham Group Plc Novel chromenes and chromans
DE3364734D1 (en) * 1982-10-19 1986-08-28 Beecham Group Plc Novel chromans and chromenes
JPS6016983A (ja) * 1983-07-08 1985-01-28 Daicel Chem Ind Ltd 3−メチレン−4−クロマノン誘導体
HU194855B (en) * 1983-02-16 1988-03-28 Alkaloida Vegyeszeti Gyar Process for producing chromene derivatives, insecticide and nematocide compositions containing chromene derivatives as active components
GB8308064D0 (en) * 1983-03-24 1983-05-05 Beecham Group Plc Active compounds
DE3475786D1 (de) * 1983-09-01 1989-02-02 Beecham Group Plc Chromanol derivatives
US4777168A (en) * 1984-10-23 1988-10-11 Rorer Pharmaceutical Corporation Bicyclic benzo-oxy heterocyclic ethers and thioethers, pharmaceutical compositions and use
ZA873745B (en) * 1986-06-04 1988-10-26 Daiichi Seiyaku Co Benzopyran derivatives
DE3726261A1 (de) * 1986-12-23 1988-07-07 Merck Patent Gmbh Chromanderivate
DE3835011A1 (de) * 1988-10-14 1990-04-19 Merck Patent Gmbh Chromanderivate
CH674984A5 (ko) * 1987-05-16 1990-08-15 Sandoz Ag
US4971982A (en) * 1987-07-06 1990-11-20 Hoffmann-La Roche Inc. Benzopyran derivatives
EP0346724A1 (de) * 1988-06-16 1989-12-20 MERCK PATENT GmbH Chromanderivate

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NO891866D0 (no) 1989-05-05
NO174467B (no) 1994-01-31
AU628331B2 (en) 1992-09-17
AU3390189A (en) 1989-11-09
EP0340718B1 (de) 1994-07-20
NZ228991A (en) 1990-12-21
JPH01319481A (ja) 1989-12-25
US5013853A (en) 1991-05-07
KR0150781B1 (ko) 1998-10-15
NO174467C (no) 1994-05-11
EP0340718A1 (de) 1989-11-08
FI892182A0 (fi) 1989-05-05
AR246966A1 (es) 1994-10-31
IL90198A0 (en) 1989-12-15
ATE108786T1 (de) 1994-08-15
DK223289A (da) 1989-11-07
PT90471B (pt) 1994-09-30
IE891474L (en) 1989-11-06
FI93358B (fi) 1994-12-15
FI892182A (fi) 1989-11-07
IE63794B1 (en) 1995-06-14
DK223289D0 (da) 1989-05-05
ES2057010T3 (es) 1994-10-16
NO891866L (no) 1989-11-07
IL90198A (en) 1994-01-25
PT90471A (pt) 1989-11-30
HU207311B (en) 1993-03-29
DE58908062D1 (de) 1994-08-25
HUT56094A (en) 1991-07-29
FI93358C (fi) 1995-03-27

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