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KR960007539A - 오르토-치환된 벤조산 유도체 - Google Patents

오르토-치환된 벤조산 유도체 Download PDF

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KR960007539A
KR960007539A KR1019950026798A KR19950026798A KR960007539A KR 960007539 A KR960007539 A KR 960007539A KR 1019950026798 A KR1019950026798 A KR 1019950026798A KR 19950026798 A KR19950026798 A KR 19950026798A KR 960007539 A KR960007539 A KR 960007539A
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methylsulfonylbenzamide
diaminomethylene
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게릭케 롤프
도르쉬 디터
바움가르쓰 만프레트
밍크 클라우스-오토
바이에르 노르베르트
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위르겐 호이만·라인하르트 쉬틀러
메르크 파텐트 게젤샤프트 미트 베슈랭크터 하프퉁
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    • C07C317/50—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
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Abstract

본 발명은 항부정맥 성질을 나타내고, 세포내 Na+/H 상호 수송기의 억제제로서 작용하는, 하기 일반식(I)의 오르토-치환된 벤조산 유도체와 이들의 생리학적으로 무해한 염을 제공한다.
(단, 상기 식에서, R1은 A, CF3, CH2F, CHF2, C2F5, CN, NO2, Hal, C≡C 또는 -X-R4이고, R2는 CF3, -SOn-R6또는 -SO2NR4R5이고, R3는 CN, Hal, COA, CHO, CSNR7R8, CONR7R8, 단 Q가 -N=C(NH3)2가 아니면 또는 A이고, Q는 구아니딜이다. 이 밖에도, 일반식(I)중, R1내지 R3및 Q가 상기에서 정의된 바와 같은 화합물은 약물, 특히 세포내 Na+/H+상호수송기의 억제제의 제조를 위한 가치있는 중간물질로서 사용하기에 적합하다.

Description

오르토-치환된 벤조산 유도체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (9)

  1. 하기 일반식(I)로 표시되는 오르토-치환된 벤조산 유도체 및 이의 생리학적으로 허용되는 염.
    (단, 상기 식에서, R1은 A, CF3, CH2F, CHF2, C2F5, CN, NO2, Hal, C≡C 또는 -X-R4이고, R2는 CF3, -SOn-R6또는 -SO2NR4R5이고, R3는 CN, Hal, COA, CHO, CSNR7R8, CONR7R8이거나, 또는 Q가 -N=C(NH3)2가 아니면 A이고, Q는 -N=C(NH2)2, Cl, Br, OA, O-CO-A, O-CO-Ph, OH 또는 다른 반응적으로 에스테르화된 OH기 또는 친핵적으로 용이하게 치환될 수 있는 이탈기이고, R4는 H, A, 탄소수 5 내지 7인 시클로알킬, 탄소수 6 내지 8인 시클로알킬메틸, CF3, CH2F, CHF2, CH2CF3, Ph 또는 -CH2-Ph이고, R5는 H 또는 A이거나, 또는 R4및 R5는 함께 결합하여 탄소수가 4 내지 5인 알킬렌이고, 여기에서 상기 알킬렌중의 하나의 CH2기는 O, S, NH, N-A 또는 N-CH2-Ph으로 대체될 수도 있으며, R6는 A 또는 Ph이고, R7및 R8은 각 경우, 서로 독립적으로 H, A 또는 Ac이고, A는 탄소수가 1 내지 인 알킬이며, X는 O, S 또는 NR5이고, Hal은 F, Cl, Br 또는 I이고, Ph는 A, OA, NR4R5, F, Cl, Br, I 또는 CF3로 1회, 2회 또는 3회 치환되거나 또는 비치환된 페닐이며, Ac는 탄소수 1 내지 10인 알카노일 또는 탄소수 7 내지 11인 아로일이고, n은 1 또는 2이다.).
  2. 제1항에 있어서, 상기한 일반식(I)의 화합물이 하기 (a) 내지 (g)인 것을 특징으로 하는 화합물 및 이들의 생리학적으로 허용되는 염: (a) N-디아미노메틸렌-2-메틸-4-브로모-5-메틸술포닐벤즈아미드; (b) N-디아미노메틸렌-2-메틸-4-클로로-5-메틸술포닐벤즈아미드; (c) N-디아미노메틸렌-2-메틸-4-시아노-5-메틸술포닐벤즈아미드; (d) N-디아미노메틸렌-2-에틸-4-브로모-5-메틸술포닐벤즈아미드; (e) N-디아미노메틸렌-2-에틸-4-클로로-5-메틸술포닐벤즈아미드; (f) N-디아미노메틸렌-2-메틸-4-플루오로-5-메틸술포닐벤즈아미드; (g) N-디아미노메틸렌-2-에틸-4-플루오로-5-메틸술포닐벤즈아미드.
  3. 제1항에 따른 일반식(I)의 오르토-치환된 벤조산 유도체 및 이의 염의 제조방법에 있어서, 하기 일반식(Ⅱ)로 표시되는 화합물을 산화시켜 일반식(I)로 표시되는 화합물로 전환시키거나, 또는 일반식(Ⅱ)중, L이 CN인 화합물을 가수분해하여 일반식(I)로 표시되는 화합물로 전환시키거나, 또는 일반식(Ⅱ)중, R2가 H이고 L이 CO2R5인 화합물은 클로로술폰화에 이어, 환원 및 알칼화하여 일반식(I)로 표시되는 화합물로 전환시키거나, 또는 일반식(I)로 표시되는 화합물을 작용성 유도체중 하나로부터 가용분해제 또는 가수소분해제로 처리하여 분리시키거나, 또는 일반식(I)에 상응하되, 라디칼 R1, R2또는 R3중 하나가 존재하지 않는 벤조산 유도체를 알킬화, 아실화, 할로겐화 또는 니트로화하여 일반식(I)로 표시되는 화합물로 전환시키거나, 또는 -일반식(I)로 표시되는 에스테르를 가수분해하거나, 또는 -일반식(I)의 카르복실산을 에스테르화하거나 또는 이 화합물을 산무수물 또는 산할라이드로 전환하거나 또는 아실구아니딘으로 전환시키거나, 또는 -CN기를 촉매적 수소화하거나, 또는 니트릴기를 촉매적 수소화하거나, 또는 -니트릴기를 가수분해하여 카르바모일기 또는 산기를 형성시키거나, 또는 -니트릴기를 티오카르바모일 기로 전환시켜 라디칼 R1, R2,R3및/또는 Q를 다른 라디칼 R1, R2,R3및 또는 Q로 전환시키거나, 또는 일반식(I)로 표시되는 화합물을 산 또는 염기로 처리하여 이의 염중의 하나로 전환시키는 것을 특징으로 하는 것을 특징으로 하는 제조방법.
    (단, 상기 식에서, R1, R2및 R3는 상기에서 정의된 바와 같고, L은 CH3, CH2OH, CHO 또는 페닐이다.).
  4. 제1항에 따른 일반식(I)중, Q가 -N=C(NH2)2인 화합물 및/또는 이의 생리학적으로 허용되는 염들중 하나를 1종 이상의 고체, 액체 또는 반고체 담체물질 또는 보조제와 함께 투여에 적합한 형태로 만드는 것을 특징으로 하는 약제학적 제형의 제조방법.
  5. 제1항에 따른 일반식(I)중, Q가 -N=C(NH2)2인, 화합물 1종 이상 및/또는 이의 생리학적으로 허용되는 염들중 하나를 함유하는 것을 특징으로 하는 약제학적 제형.
  6. 제1항에 따른 일반식(I)중, Q가 -N=C(NH2)2인 화합물 및/또는 이의 생리학적으로 허용되는 염들중 하나를 질병의 치료에 사용하는 용도.
  7. 제1항에 따른 일반식(I)중, Q가 -N=C(NH2)2인, 화합물 및/또는 이의 생리학적으로 허용되는 염들중 하나를 약물의 제조에 사용하는 용도.
  8. 제1항에 따른 일반식(I)중, Q가 -N=C(NH2)2인, 화합물을 부정맥, 협심증 및 경색증의 치료와 또한 상기한 질병의 예방적 치료에 위한 약물의 제조에 사용하는 용도.
  9. 제1항에 따른 일반식(I)의 벤조산 유도체를 세포내 Na+/H+상호수송기를 억제하는 활성화합물을 제조하기 위한 중간물질로서 사용하는 용도.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019950026798A 1994-08-28 1995-08-28 오르토-치환된벤조산유도체 KR100406686B1 (ko)

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ZA957161B (en) 1996-04-17
KR100406686B1 (ko) 2004-07-19
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BR9503817A (pt) 1996-04-16
NO953352D0 (no) 1995-08-25
CN1068587C (zh) 2001-07-18
US5849796A (en) 1998-12-15
NO305794B1 (no) 1999-07-26
SK105495A3 (en) 1996-03-06
TW406067B (en) 2000-09-21
AU3014595A (en) 1996-03-14
EP0704431A3 (de) 1997-01-29
DE4430212A1 (de) 1996-02-29
ATE193282T1 (de) 2000-06-15
CZ218195A3 (en) 1996-03-13
UA44238C2 (uk) 2002-02-15
ES2147810T3 (es) 2000-10-01
CN1125722A (zh) 1996-07-03
HU9502500D0 (en) 1995-10-30
DK0704431T3 (da) 2000-09-11
HUT74946A (en) 1997-03-28
EP0704431B1 (de) 2000-05-24
DE59508383D1 (de) 2000-06-29
GR3033989T3 (en) 2000-11-30
RU2125981C1 (ru) 1999-02-10
PT704431E (pt) 2000-10-31
NO953352L (no) 1996-02-29
PL310192A1 (en) 1996-03-04
JPH0859602A (ja) 1996-03-05
EP0704431A2 (de) 1996-04-03
CA2156959A1 (en) 1996-03-01
PL181183B1 (pl) 2001-06-29
SK282202B6 (sk) 2001-12-03
AU703633B2 (en) 1999-03-25

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