KR940014368A - 신규한 나프탈렌 유도체 - Google Patents

신규한 나프탈렌 유도체 Download PDF

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KR940014368A
KR940014368A KR1019930029869A KR930029869A KR940014368A KR 940014368 A KR940014368 A KR 940014368A KR 1019930029869 A KR1019930029869 A KR 1019930029869A KR 930029869 A KR930029869 A KR 930029869A KR 940014368 A KR940014368 A KR 940014368A
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alkyl
hydrogen atom
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aryl
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KR100293891B1 (ko
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히로아끼 우에노
다까유끼 오오에
이찌로오 스에히로
후미꼬 나까무라
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미야베 요시가즈
미쓰비시 가세이 가부시기가이샤
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/24Radicals substituted by oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D257/00Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04Five-membered rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/06Antihyperlipidemics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
    • C07D277/34Oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
    • C07D277/36Sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Abstract

[구성] 아래의 일반식(Ⅰ)으로 나타내어지는 나프탈렌 유도체 또는 약학상 허용되는 그염.
-X- : -0- 또는 -S-
=Y- : =N- 또는 =CR5-
R1, R2, R3, R4, R5: H, 할로겐원자, 알킬기 등
R6: H, 알킬기, 아릴기등의 정수
n : 0~3의 정수
‥ : 단일 결합 또는 이중 결합
[효과] 혈당 저하 작용 및 혈중 지질 저하 작용이 우수한 신규의 나프탈렌 유도체를 제공한다.

Description

신규한 나프탈렌 유도체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (7)

  1. 아래의 일반식(Ⅰ)으로 나타내는 나프탈렌 유도체 또는 약학상 허용되는 그 염.
    을 나타내고 -X-는 -O- 또는 -S-을 나타내며, =Y-는 =N- 또는 =CR5을 나타내고, R1, R2, R3R4및 R5및 는 각각 독립하여 수소 원자, 할로겐 원자, 알킬기, 아릴기, 알콕시기, 알콕시알콕시기, 아릴옥시기, 알카노일옥시기, 아릴 카르보닐옥시기, 카르복실기, 알콕시카르보닐기, 아릴옥시카르보닐기, 카르바모일기, 알킬아미노카르보닐기, 아릴아미노카르보닐기, 아미노기, 아킬아미노기, 알카노일아미노기, 아릴카르보닐아미노기, 에틸렌디옥시메틸기, 포르밀기, 시아노기, 니트로기, 또는 트리할로메틸기를 나타내며 R6는 수소원자, 치환되어도 좋은 알킬기 또는 치환되어도 좋은 아릴기를 나타내고, n은 0~3의 정수를 나타내며, 점선을 해당 부위의 결합이 이중 결합이어도 좋은 것을 나타낸다.
  2. 제 1 항에 있어서, R1, R2, R3,R4및 R5및 는 각각 독립하여 수소 원자, 할로겐 원자, C1~C8의 알킬기, C6~C12의 아릴기, C1~C8의 알콕시기, C2~C6의 알콕시알콕시기, C6~C12의 아릴옥시기, C2~C9의 알카노일 옥시기, C7~C13의 아릴카르보닐옥시기, 카르복시기, C2~C9의 알콕시카르보닐기, C7~C13의 아릴옥시카르보닐기, 카르바모일기, C2~C9의 알킬아미노카르보닐기, C7~C13의 아릴아미노카르보닐기, 아미노기, C1~C8의 알킬아미노기, C2~C9알카노일아미노기, C7~C13의 아릴카르보닐아미노기, 에틸렌디옥시메틸기, 포르밀기, 시아노기, 니트로기, 또는 트리할로메틸기를 나타내고, R6는 수소 원자 ; 페닐기, 할로겐 원자, 니트로기 및 시아노기로 부터 선택되는 하나 이상의 치환기를 가지고 있어도 좋은 C1~C8의 알킬기 ; 또는 C1~C8의 알킬기, 할로겐 원자, 니트로기 및 시아노기로 부터 선택되는 하나 이상의 치환기를 가지고 있어도 좋은 C6~C12의 아릴기를 나타내는 것을 특징으로 하는 화합물.
  3. 제 1 항에 있어서, R1, R2, R3, R4및 R5및 는 각각 독립하여 수소 원자, 할로겐 원자, C1~C8의 알킬기, C1~C8의 알콕시기, C2~C6의 알콕시 알콕시기, C2~C9의 알카노일 옥시기, C7~C13의 아릴카르보닐옥시기, 카르복실기, C2~C9의 알콕시카르보닐기, 카르바모일기, C1~C9의 알킬 아미노카르보닐기, C7~C13의 아릴아미노카르보닐기, 아미노기, C1~C8의 알킬아미노기, C2~C9의 알카노일 아미노기, C7~C13의 아릴카르보닐아미노기, 에틸렌디옥시메틸기, 포르밀기, 시아노기, 니트로기, 또는 트리할로메틸기를 나타내고, R6가 수소 원자 ; C1~C8의 알킬기 ; 또는 할로겐 원자로 치환되어 있어도 좋은 C6~C12의 아릴기를 나타내는 것을 특징으로 하는 화합물.
  4. 제 1 항에 있어서, X가 -O-을 나타내고 Y가 =CR5-를 나타내며, R1, R2, R3, R4및 R5및 는 각각 독립하여 수소 원자, 할로겐 원자, C1~C8의 알킬기, C1~C8의 알콕시기, C2~C6의 알콕시알콕시기, C2~C6의 알카노일옥시기, 카르복시기, C2~C6의 알콕시카르보닐기, C7~C13의 아릴 아미노카르보닐기, 아미노기, C2~C6의 알카노일 아미노기, 에틸렌디옥시메틸기, 포르밀기, 시아노기, 니트로기, 또는 트리할로메틸기를 나타내고, R6가 수소 원자 ; C1~C8의 알킬기 ; 또는 할로겐 원자로 치환되어 있어도 좋은 C6~C12의 알킬기를 나타내는 것을 특징으로 하는 화합물.
  5. 제 1 항에 있어서,을 나타내고, -X가 -O-을 나타내며, =Y-가 =CR5을 나타내고, R1, R2, R3및 R5및 는 각각 독립하여 수소 원자 또는 할로겐 원자를 나타내며, R5가 수소 원자를 나타내며, R6가 수소 원자를 나타내며, n가 1을 나타내고, 점선의 해당 부위의 결합이 단일 결합인 것을 특징으로 하는 화합물.
  6. 제 1 항 기재의 화합물과 약학적으로 허용되는 담체를 함유하여 됨을 특징으로 하는 의약 조성물.
  7. 제 1 항 기재의 화합물과 약학적으로 허용되는 담체를 함유하여 됨을 특징으로 하는 당뇨병을 위한 의약 조성물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019930029869A 1992-12-28 1993-12-27 신규한나프탈렌유도체 KR100293891B1 (ko)

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JP92-349172 1992-12-28
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JP (1) JP2845743B2 (ko)
KR (1) KR100293891B1 (ko)
AT (1) ATE145400T1 (ko)
CA (1) CA2112331C (ko)
DE (1) DE69306094T2 (ko)
DK (1) DK0604983T3 (ko)
ES (1) ES2097431T3 (ko)
GR (1) GR3021746T3 (ko)
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Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0783496B9 (en) * 1994-08-10 2003-09-03 Takeda Chemical Industries, Ltd. Thiazolidinedione derivatives, their production and use
CA2171702A1 (en) * 1995-03-14 1996-09-15 Takashi Sohda Benzofuran compounds and their use
NZ314406A (en) * 1996-03-18 2000-12-22 Sankyo Co Treatment or prophylaxis of pancreatitis with a medicament containing an insulin sensitiser including oxazoles and thiazoles
US5919782A (en) * 1996-05-06 1999-07-06 Dr. Reddy's Research Foundation Heterocyclic compounds having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them
ZA973848B (en) * 1996-05-06 1997-12-02 Reddy Research Foundation Novel heterocyclic compounds having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them.
ZA973850B (en) * 1996-05-06 1997-12-02 Reddy Research Foundation Novel antidiabetic compounds having hypolipidaemic, anti-hypertensive properties, process for their preparation and pharmaceutical compositions containing them.
CA2257284C (en) * 1996-05-31 2005-10-04 Sankyo Company Limited Remedy for autoimmune diseases
US6372750B2 (en) 1996-07-01 2002-04-16 Dr. Reddy's Research Foundation Heterocyclic compounds, process for their preparation and pharmaceutical compounds containing them and their use in the treatment of diabetes and related diseases
CA2259431A1 (en) * 1996-07-01 1998-01-08 Eli Lilly And Company Hypoglycemic and hypolipidemic compounds
US5885997A (en) * 1996-07-01 1999-03-23 Dr. Reddy's Research Foundation Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases
USRE39266E1 (en) * 1996-07-01 2006-09-05 Dr. Reddy's Laboratories, Limited Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases
US5985884A (en) * 1996-07-01 1999-11-16 Dr. Reddy's Research Foundation Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases
US6114526A (en) * 1996-07-01 2000-09-05 Dr. Reddy's Research Foundation Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases
US6011036A (en) * 1997-04-15 2000-01-04 Dr. Reddy's Research Foundation Heterocyclic compounds having antidiabetic hypolipidemic antihypertensive properties process for their preparation and pharmaceutical compositions containing them
US6011031A (en) * 1997-05-30 2000-01-04 Dr. Reddy's Research Foundation Azolidinediones useful for the treatment of diabetes, dyslipidemia and hypertension: process for their preparation and pharmaceutical compositions containing them
HUP9902721A2 (hu) 1997-11-25 1999-12-28 The Procter & Gamble Co. Tömény textillágyító készítmény és ehhez alkalmazható magas telítetlenségű textillágyító vegyület
AU1507799A (en) * 1997-12-16 1999-07-05 Sankyo Company Limited Leukemia remedy
AU6330999A (en) * 1998-09-30 2000-04-17 Roche Diagnostics Gmbh Rhodanine derivatives for the treatment and prevention of metabolic bone disorders
ATE315552T1 (de) 1998-11-20 2006-02-15 Mitsubishi Chem Corp 5-((6-(2-fluorbenzyl)oxy-2-naphtyl)methyl)- thiazolid in-2,4-dion kristallen
DE60043152D1 (de) 1999-05-27 2009-11-26 Cmic Co Ltd Heilmittel für nierenkrankheiten und verfahren zum screenen selbiger
US6878749B2 (en) 1999-09-17 2005-04-12 Novartis Ag Method of treating metabolic disorders, especially diabetes, or a disease or condition associated with diabetes
US6559188B1 (en) 1999-09-17 2003-05-06 Novartis Ag Method of treating metabolic disorders especially diabetes, or a disease or condition associated with diabetes
AR028299A1 (es) 1999-09-17 2003-05-07 Novartis Ag Una composicion farmaceutica que comprende nateglinida, un proceso para su preparacion y el uso de dicha composicion para la preparacion de un medicamento para el tratamiento de desordenes metabolicos, especialmente diabetes, o de una enfermedad o condicion asociada con diabetes.
IL149593A0 (en) * 1999-11-19 2002-11-10 Ortho Mcneil Pharm Inc Solid state forms of 5-[[6-[(2-fluorophenyl)methoxy]-2-naphthalenyl] methyl]-2,4-thiazolidinedione
JP2003520226A (ja) 2000-01-21 2003-07-02 ノバルティス アクチエンゲゼルシャフト ジペプチジルペプチダーゼ−iv阻害剤および抗糖尿病薬剤を含む組合せ物
US20040198774A1 (en) * 2001-08-23 2004-10-07 Shinichi Ishii Preventive and/or remedial agent for disease attributable to arteriosclerotic activity
MX2009002282A (es) 2006-09-07 2009-03-20 Nycomed Gmbh Tratamiento de combinacion para diabetes mellitius.
CA2963857A1 (en) 2007-06-04 2008-12-11 Ben-Gurion University Of The Negev Research And Development Authority Tri-aryl compounds and compositions comprising the same
WO2010095227A1 (ja) * 2009-02-19 2010-08-26 富士通株式会社 新規化合物、並びに、結合阻害剤、抗アレルギー剤、抗喘息剤、及び抗炎症剤
JP5370472B2 (ja) * 2009-02-19 2013-12-18 富士通株式会社 新規化合物、並びに、結合阻害剤、抗アレルギー剤、抗喘息剤、及び抗炎症剤
JP6657101B2 (ja) 2013-11-05 2020-03-04 ベン グリオン ユニバーシティ オブ ザ ネガフ リサーチ アンド ディベロップメント オーソリティ 糖尿病及びそれから生じる疾患合併症の治療のための化合物

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4582839A (en) * 1984-03-21 1986-04-15 Takeda Chemical Industries, Ltd. 2,4-thiazolidinediones
AR240698A1 (es) * 1985-01-19 1990-09-28 Takeda Chemical Industries Ltd Procedimiento para preparar compuestos de 5-(4-(2-(5-etil-2-piridil)-etoxi)benzil)-2,4-tiazolidindiona y sus sales
DK173350B1 (da) * 1985-02-26 2000-08-07 Sankyo Co Thiazolidinderivater, deres fremstilling og farmaceutisk paæparat indeholdende dem
HU210339B (en) * 1985-05-21 1995-03-28 Pfizer Process for preparing thiazolidinediones and their pharmaceutical compositions haring hypoglycemic effect
FI91869C (fi) * 1987-03-18 1994-08-25 Tanabe Seiyaku Co Menetelmä antidiabeettisena aineena käytettävien bensoksatsolijohdannaisten valmistamiseksi
JPS6456675A (en) * 1987-03-18 1989-03-03 Tanabe Seiyaku Co Benzoxazole derivative

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JP2845743B2 (ja) 1999-01-13
TW324718B (en) 1998-01-11
EP0604983A1 (en) 1994-07-06
KR100293891B1 (ko) 2001-09-17
DE69306094D1 (de) 1997-01-02
EP0604983B1 (en) 1996-11-20
CA2112331C (en) 2004-12-07
ES2097431T3 (es) 1997-04-01
CA2112331A1 (en) 1994-06-29
DE69306094T2 (de) 1997-04-03
DK0604983T3 (da) 1996-12-09
GR3021746T3 (en) 1997-02-28
ATE145400T1 (de) 1996-12-15
JPH06247945A (ja) 1994-09-06

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