KR940006590A - 알쯔하이머 질환 치료용 및 혈당저하제로서 유용한 화합물 - Google Patents
알쯔하이머 질환 치료용 및 혈당저하제로서 유용한 화합물 Download PDFInfo
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- KR940006590A KR940006590A KR1019930018138A KR930018138A KR940006590A KR 940006590 A KR940006590 A KR 940006590A KR 1019930018138 A KR1019930018138 A KR 1019930018138A KR 930018138 A KR930018138 A KR 930018138A KR 940006590 A KR940006590 A KR 940006590A
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- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
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- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
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- C07D277/32—Heterocyclic 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
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- C07D277/32—Heterocyclic 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
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Abstract
특정 로다닌 유도체를 이용한 과혈당증 및 알쯔하이머 질환의 치료방법이 제공된다. 본 치료 방법에 사용되는 로다닌 유도체는 신규화합물이며, 이 화합물 그의 제조방법 및 그의 약학적 제제도 제공된다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 포유 동물의 혈중 글루코스 농도를 감소시키기에 유용한 약제의 제조를 위한 하기 일반식(Ⅰ)의 화합물 또는 그의 약학적으로 허용가능한 염의 용도:상기식에서, Ar은 (ⅰ)페닐, (ⅱ)C1-C8알킬,C1-C8알콕시, C1-C8알킬티오, 트리플루오로메틸, C1-C4알킬페닐, 페닐, NO2,F,CL, 하이드록시, 페녹시, C1-C4알킬옥시페닐, 티오페닐, C1-C4알킬티오페닐, COOR7,-N(R7)2또는 -N(R7)SO2R7(여기서, 각 R7은 독립적으로 수소 또는 C1-C6알킬이다)중에서 독립적으로 선택된 1내지 3의 치환체로 치환된 페닐, (iii)1-또는 2-나프틸, (iv)2-또는3-벤조푸라닐, (v)2-또는3-벤조티오페닐, (vi)2-또는3-티에닐, (vii)2-,3-또는 4-피리딜, (viii)2-또는3-푸라닐, (ix)1,3-벤조디옥사닐, (x)치환된1,3-벤조디옥사닐, (xi)퀴놀리닐, (xii)2-또는3-인돌릴 또는 (xiii)N-치환된 2-또는 3-인돌릴이고, R1은 C1-C6알킬, C1-C4알킬페닐, 수소, 페닐, 또는 Cl,Br,F,l, C1-C4알킬, C1-C4알콕시, 하이드록시, 트리플루오로메틸, -NH2, -NH(C1-C4알킬), -N(C1-C4알킬)2또는 C1-C4알킬티오중에서 독립적으로 선택된 1 또는 2의 치환체로 치환된 페닐이고, R2및 R3는 각각 수소이고 또는 함께 취해질 경우 결합을 형성하고, R4및 R5는 각각 수소이고 또는 함께 취해질 경우 =S이고, 또는 R4와 R5중의 하나가 수소일 경우 다른 하나는 -SCH3이고,R6은 수소, C1-C6알킬, C3-C8시클로알킬, C2-C6알케닐, -SO2CH3또는 -(CH2)p-Y[여기서, p는 0,1,2또는 3이고 Y는 시아노, -OR8,테트라졸릴, -NR10R11, -SH, C1-C4알킬티오 또는--O-C1-C4알킬(여기서, R8은 수소, C1-C4알킬 또는알킬이고, R9는 수소, C1-C4알킬, C1-C4알콕시, 하이드록시 또는 NH2이고, R10및 R11은 각각 독립적으로 수소, C1-C6알킬, C2-C6알케닐, C2-C6알키닐, 페닐, C1-C4알킬페닐, -(CH2)qN(C1-C4알킬)2또는 -(CH2)qS(C1-C4알킬)(여기서, q는 1내지 6이다)이고 또는 R10과 R11은 이들이 결합하는 질소원자와 함께 취해져 모르폴리닐, 피페리디닐, 피페라지닐 또는 N-메틸피페라지닐 고리를 형성한다)이다]이고, m은 0,1 또는 2이고, 단, Ar은 페닐 고리의 4-위치에 하나의 클로로 치환체만으로 치환된 페닐일수 없고,Ar은 페닐 고리의 2-위치에 COOH잔기로 치환된 페닐일 수 없고, Ar이 페닐 고리의 3- 및 4-위치에 2개의 에톡시 잔기로 치환된 페닐일 경우, R1은 수소이어야하고, Ar은 두개의 하이드록시 치환체만으로 치환된 페닐일 수 없고, R4와 R5가 각각 수소일 경우, R6은 C1-C6알킬일 수 없다.
- 제1항에 있어서, 사용된 화합물이 5-[(3-메톡시-4-펜톡시페닐)메틸렌]-2-티옥소-4-티아졸리디논 또는 그의 약학적으로 허용가능한 염인 용도.
- 하나 또는 그 이상의 약학적으로 허용가능한 담체, 희석제 또는 부형제와 함께 혼합된 제1항 또는 제2항에 기재된 화합물을 포함하는, 혈중 글루코스 농도를 감소시키기 위한 약학적 제제.
- 알쯔하이머 질환의 치료에 유용한 약제의 제조를 위한 하기 일반식(I)의 화합물 또는 그의 약학적으로 허용가능한 염의 농도:상기식에서, Ar은 (i)페닐, (ii)C1-C8알킬, C1-C8알콕시, C1-C8알킬티오, 트리플루오로메틸, C1-C4알킬티오페닐, 페닐, NO2,F,Cl, 하이드록시, 페녹시, C1-C4알킬옥시페닐, 티오페닐, C1-C4알킬티오페닐, -COOR7, -N(R7)2또는 -N(R7)SO2R7(여기서, 각 R7은 독립적으로 수소 또는 C1-C6알킬이다)중에서 독립적으로 선택된 1내지 3의 치환체로 치환된 페닐, 또는 (iii)1- 또는 2-나프틸이고, R1은 C1-C6알킬, C1-C4알킬페닐, 수소, 페닐, 또는 Cl,Br,F,l, C1-C4알킬, C1-C4알콕시, 하이드록시, 트리플루오로메틸, -NH2, -NH(C1-C4알킬), -N(C1-C4알킬)2또는 C1-C4알킬티오중에서 독립적으로 선택된 1 또는 2의 치환체로 치환된 페닐이고, R2및 R3는 각각 수소이고 또는 함께 취해질 경우 결합을 형성하고, R4및 R5는 각각 수소이고 또는 함께 취해질 경우 =S이고, 또는 R4와 R5중의 하나가 수소일 경우 다른 하나는 -SCH3이고,R6은 수소, C1-C6알킬, C3-C8시클로알킬, C2-C6알케닐, -SO2CH3또는 -(CH2)p-Y[여기서, p는 0,1,2또는 3이고 Y는 시아노, -OR8,테트라졸릴, -NR10R11, -SH, C1-C4알킬티오 또는--O-C1-C4알킬(여기서, R8은 수소, C1-C4알킬 또는알킬이고, R9는 수소, C1-C4알킬, C1-C4알콕시, 하이드록시 또는 NH2이고, R10및 R11은 각각 독립적으로 수소, C1-C6알킬, C2-C6알케닐, C2-C6알키닐, 페닐, C1-C4알킬페닐, -(CH2)qN(C1-C4알킬)2또는 -(CH2)qS(C1-C4알킬)(여기서, q는 1내지 6이다)이고 또는 R10과 R11은 이들이 결합하는 질소원자와 함께 취해져 모르폴리닐, 피페리디닐, 피페라지닐 또는 N-메틸피페라지닐 고리를 형성한다)이다]이고, m은 0,1 또는 2이다.
- 제4항에 있어서, 사용된 화합물이 5-[(3-(1,1-디메틸에틸)-4-하이드록시-5(메틸티오페닐)페닐]메티렌]-2-티옥소-4-티아졸리디논 또는 그의 약학적으로 허용가능한 염인 용도.
- 하나 또는 그 이상의 약학적으로 허용가능한 담체, 희석제 또는 부형제와 함께 혼합된 제5항 또는 제6항에 기재된 화합물을 포함하는, 알쯔하이머 질환의 치료를 위한 약학적 제제.
- 하기 일반식(Ⅰ)의 화합물 또는 그의 약학적으로 허용가능한 염:상기식에서, Ar은 (i)페닐, (ii)C1-C8알킬, C1-C8알콕시, C1-C8알킬티오, 트리플루오로메틸, NO2, F, Cl, 페녹시, C1페닐, 티오페닐, C1-C4알킬티오페닐, -COOR7, -N(R7)2또는 -N(R7)SO2R7(여기서, 각 R7은 독립적으로 수소 또는 함께 취해질 경우 결합을 형성하고, R4및 R5는 각각 수소이고 또는 C1-C6알킬이다)중에서 독립적으로 선택된 1 내지 3의 치환체로 치환된 페닐, 또는 (iii)1-또는 2-나프틸, (iv)2-또는3-벤조푸라닐, (v)2-또는3-벤조티오페닐, (vi)2-또는3-티에닐, (vii)2-,3-또는 4-피리딜, (viii)2-또는3-푸라닐, (ix)1,3-벤조디옥사닐, (x)치환된1,3-벤조디옥사닐, (xi)퀴놀리닐, (xii)2-또는3-인돌릴 또는 (xiii)N-치환된 2-또는 3-인돌릴이고, R1은 C1-C6알킬, C1-C4알킬페닐, 수소, 페닐, 또는 Cl,Br,F,l, C1-C4알킬, C1-C4알콕시, 하이드록시, 트리플루오로메틸, -NH2, -NH(C1-C4알킬), -N(C1-C4알킬)2또는 C1-C4알킬티오중에서 독립적으로 선택된 1 또는 2의 치환체로 치환된 페닐이고, R2및 R3는 각각 수소이고 또는 함께 취해질 경우 결합을 형성하고, R4및 R5는 각각 수소이고 또는 함께 취해질 경우 =S이고, 또는 R4와 R5중의 하나가 수소일 경우 다른 하나는 -SCH3이고,R6은 수소, C1-C6알킬, C3-C8시클로알킬, C2-C6알케닐, -SO2CH3또는 -(CH2)p-Y[여기서, p는 0,1,2또는 3이고 Y는 시아노, -OR8,테트라졸릴, -NR10R11, -SH, C1-C4알킬티오 또는--O-C1-C4알킬(여기서, R8은 수소, C1-C4알킬 또는알킬이고, R9는 수소, C1-C4알킬, C1-C4알콕시, 하이드록시 또는 NH2이고, R10및 R11은 각각 독립적으로 수소, C1-C6알킬, C2-C6알케닐, C2-C6알키닐, 페닐, C1-C4알킬페닐, -(CH2)qN(C1-C4알킬)2또는 -(CH2)qS(C1-C4알킬)(여기서, q는 1내지 6이다)이고 또는 R10과 R11은 이들이 결합하는 질소원자와 함께 취해져 모르폴리닐, 피페리디닐, 피페라지닐 또는 N-메틸피페라지닐 고리를 형성한다)이다]이고, m은 0,1 또는 2이고, (ⅰ)페닐, (ⅱ)C1-C8알킬,C1-C8알콕시, F,Cl, 트리플루오로메틸, 페녹시, C1-C4알킬옥시페닐, C1-C8알킬티오, NO2,-N(R7)2또는 -COOR7(여기서, 각 R7은 독립적으로 수소 또는 C1-C6알킬이다)중에서 독립적으로 선택된 1내지 3의 치환체로 치환된 페닐, (iii)1-또는 2-나프틸, (iv)2-또는3-벤조푸라닐, (v)2-또는3-벤조티오페닐, (vi)2-또는3-티에닐, (vii)2-또는 3-인돌릴, (viii)2-또는3-푸라닐, (ix)2-,3-또는 4-피리딜 또는 (x)퀴놀리닐이고, R1이 수소 또는 C1-C6알킬이고, R2및 R3가 함께 결합을 형성하고, m이 0이고, R4및 R5는 함께 취해져 =S일 경우, R6은 수소 또는 C1-C6알킬이 아닌 다른 것이여야 하고, Ar이 페닐 고리의 4-위치에 하나의 클로로 치환체만으로 치환된 페닐일수 없고, Ar이 페닐 고리의 3- 및 4-위치에 2개의 에톡시 잔기로 치환된 페닐일 경우, R1은 수소이어야 하고, Ar이 페닐고리의 2-위치에 COOH잔기로 치환된 페닐일 수 없고, R4및 R5가 각각 수소일 경우, R6은 C1-C6알킬일 수 없다.
- 화합물 5-[(3-메톡시-4-펜톡시페닐)메틸렌]-2-티옥소-4-티아졸리디논 또는 그의 약학적으로 허용가능한 염.
- 화합물 5-[(3-(1,1-디메틸에틸)-4-하이드록시75(메틸티오페닐)페닐]메티렌]-2-티옥소-4-티아졸리디논 또는 그의 약학적으로 허용가능한 염.
- 하나 또는 그 이상의 약학적으로 허용가능한 담체, 희석제 또는 부형제와 함께 혼합된 제7항 또는 제9항중의 어느 한 항의 화합물을 포함하는 약학적 제제.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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WO2016077793A1 (en) * | 2014-11-14 | 2016-05-19 | Children's Hospital Medical Center | Sos1 inhibitors for cancer treatment |
CN104557767B (zh) * | 2015-01-14 | 2016-06-29 | 成都中医药大学 | 罗丹宁手性环己烷螺环化合物及其制备方法与用途 |
CN106008494B (zh) * | 2016-05-31 | 2019-08-27 | 广东工业大学 | 一种含4-氧代-2-硫代噻唑烷基衍生物及其制备方法与应用 |
CN114945569A (zh) * | 2019-12-26 | 2022-08-26 | 延世大学校产学协力团 | 吡咯烷衍生物,以及包含其的用于预防或治疗β-淀粉样蛋白或Tau蛋白相关疾病的药物组合物 |
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-
1993
- 1993-09-02 CZ CZ931814A patent/CZ181493A3/cs unknown
- 1993-09-02 ZA ZA936492A patent/ZA936492B/xx unknown
- 1993-09-02 EP EP98201389A patent/EP0915090A1/en not_active Withdrawn
- 1993-09-02 EP EP19930306959 patent/EP0587377A3/en not_active Withdrawn
- 1993-09-02 NZ NZ248573A patent/NZ248573A/en unknown
- 1993-09-02 IL IL106877A patent/IL106877A/en not_active IP Right Cessation
- 1993-09-03 TW TW082107213A patent/TW274546B/zh active
- 1993-09-06 MX MX9305444A patent/MX9305444A/es unknown
- 1993-09-07 CA CA002105598A patent/CA2105598A1/en not_active Abandoned
- 1993-09-07 MY MYPI93001815A patent/MY131443A/en unknown
- 1993-09-08 NO NO933198A patent/NO933198L/no unknown
- 1993-09-08 HU HU9302551A patent/HUT70184A/hu unknown
- 1993-09-08 AU AU46218/93A patent/AU676843B2/en not_active Ceased
- 1993-09-08 RU RU93051176A patent/RU2131251C1/ru active
- 1993-09-09 PL PL93300335A patent/PL300335A1/xx unknown
- 1993-09-09 CN CN93119081A patent/CN1091006A/zh active Pending
- 1993-09-09 KR KR1019930018138A patent/KR940006590A/ko not_active Application Discontinuation
- 1993-09-09 FI FI933946A patent/FI933946A/fi unknown
- 1993-09-09 JP JP5224434A patent/JPH06192091A/ja not_active Withdrawn
- 1993-09-15 YU YU59593A patent/YU59593A/sh unknown
-
1994
- 1994-03-16 US US08/213,651 patent/US5523314A/en not_active Expired - Fee Related
-
1995
- 1995-06-06 US US08/470,822 patent/US5716975A/en not_active Expired - Fee Related
-
1996
- 1996-07-10 US US08/678,015 patent/US5661168A/en not_active Expired - Fee Related
-
1998
- 1998-04-28 NO NO981911A patent/NO981911D0/no unknown
Also Published As
Publication number | Publication date |
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NZ248573A (en) | 1996-02-27 |
ZA936492B (en) | 1995-03-02 |
US5523314A (en) | 1996-06-04 |
IL106877A0 (en) | 1993-12-28 |
FI933946A0 (fi) | 1993-09-09 |
MX9305444A (es) | 1994-05-31 |
IL106877A (en) | 1998-03-10 |
US5716975A (en) | 1998-02-10 |
NO981911L (no) | 1994-03-11 |
MY131443A (en) | 2007-08-30 |
NO933198L (no) | 1994-03-11 |
NO981911D0 (no) | 1998-04-28 |
JPH06192091A (ja) | 1994-07-12 |
CN1091006A (zh) | 1994-08-24 |
PL300335A1 (en) | 1994-03-21 |
NO933198D0 (no) | 1993-09-08 |
AU676843B2 (en) | 1997-03-27 |
EP0915090A1 (en) | 1999-05-12 |
EP0587377A2 (en) | 1994-03-16 |
YU59593A (sh) | 1997-01-08 |
HUT70184A (en) | 1995-09-28 |
EP0587377A3 (en) | 1994-09-21 |
FI933946A (fi) | 1994-03-11 |
RU2131251C1 (ru) | 1999-06-10 |
TW274546B (ko) | 1996-04-21 |
CA2105598A1 (en) | 1994-03-11 |
AU4621893A (en) | 1994-03-17 |
CZ181493A3 (en) | 1994-03-16 |
HU9302551D0 (en) | 1993-11-29 |
US5661168A (en) | 1997-08-26 |
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