KR930019630A - 셀폰아미도- 및 셀폰아미도카보닐피리딘-2-카복스아미드 및 이의 피리딘-n-옥사이드, 이의 제조방법 및 약제로서 이의용도 - Google Patents
셀폰아미도- 및 셀폰아미도카보닐피리딘-2-카복스아미드 및 이의 피리딘-n-옥사이드, 이의 제조방법 및 약제로서 이의용도 Download PDFInfo
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Abstract
본 발명은 하기 일반식(Ⅰ)의 설폰아미도- 및 설폰아미도카보닐피리딘-2카복스아미드 및 특히 섬유성 질환에 대한 이의 약제로서의 용도에 관한 것이다.
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Claims (2)
- 하기 일반식(I)의 설폰아미도―또는 설폰아미도카보닐 피리딘―2―카복스아미드 또는 이의 피리딘―N―옥사이드.상기식에서, A는 R3이고 B는 X―NR6R7이거나, B는R3이고 A는 X―NR6R7이며, X는 단일결합 또는 ―CO―이고,R1, R2및R3은 동일하거나 상이하며 수소, 비치환 또는 치환된(C1-C6)―알킬, (C1-C6) ―알콕시, 할로겐, 특히 불소, 염소 또는 브롬, 니트릴, 하이드록실 또는 아미노이며,R6은 수소, (C1-C6)―알킬 또는 N―보호그룹, 예를 들면,(C1-C8)―알카노일, (C1-C8)―알킬바모일, (C1-C6)―알콕시카보닐, 벤질옥시카보닐, (C1-C10)―아실옥시―(C1-C6)알킬, 바람직하게는 (C1-C10)―알카노일옥시―(C1-C6)―알킬, 벤조일옥시―(C1-C6)―알킬, 벤질옥시카보닐옥시―(C1-C6)―알킬 또는 (C1-C6)―알콕시카보닐옥시―알킬, 또는 (C1-C8)―알킬, (C1-C8)―하이드록시알킬, (C1-C4)―알콕시―(C1-C8)―알킬, 페닐, 벤질, 또는 하이드록실 또는 (C1-C4)―알콕시에 의해 1 내지 3회 치환될 수 있는 (C1-C)알킬에 의해 1 내지 3회 임의로 치환된 1―, 2―, 3―, 4가 생리학적으로 유용한 양이온, 특히 Na, K, Mg, Ca, Al, 또는 암모늄이온, 또는 염기성 아미노산 유도체의 양이온이고,R7은 ―SO2H를 제외한, 하기 일반식(Ⅱ)의 라디칼이며,―Y―〔C―U〕r―D―W (Ⅱ)〔상기식에서, Y는 ―SO2― 또는 ―CO―이고, C는 결합, 또는 직쇄 또는 축쇄 지방족(C1-C16) ―알칸디일 또는 지환족(C2-C16) ―알칸디일 라디칼 또는 직쇄 또는 측쇄(C2-C16) ―알칸디일 또는 사이클로알켄디일 라디칼, 또는(C2-C16) ―알칸디일 라디칼 또는(C2-C16) ―알케닌디일 라디칼이며, 이들은 각각 하나 이상의 C―C다중 결합을 함유할 수 있고, U는 결합 또는 수소, 또는 다음 일련의 헤테로원자 그룹 ―CO―, ―O(CO)―, ―(CO)―O―, ―(CO)NR―, NR(CO)―, ―O―, ―SO―, ―SO2―, ―NR(여기에서, R은 (C1-C3)―알킬 또는 수소이다)중의 라디칼이며, r은 1, 2, 3 또는 4이고, C는 결합 또는 수소, 또는 직쇄 또는 측쇄 지방족 (C1-C10)―알켄디일 라디칼, (C2-C10)―알킨디일 라디칼 또는 (C2-C10)―알케닌디일 라디칼이며, 이들은 각각 하나 이상의 C―C다중 결합을 함유할 수 있고, W는 결합 또는 수소, 또는 (C8-C10) ―지환족 알킬, 알케닐, 알키닐 또는 알케니닐 라디칼 또는 (C6-C10)―아릴 라디칼 또는 5― 또는 6원 헤테로아릴 라디칼이며, 여기에서 가변성분 C 또는 D 또는 W중 하나 이상은 결합이 아니고, C가 결합이 아니거나 D 및/또는 W가 결합이 아닐 경우, U는 헤테로원자 그룹일 뿐이고; C및/또는 W는, 결합 또는 수소가 아닐 경우, 바람직하게는 이들의 부분에서 치환된다.〕 R4및R5는 서로 독립적으로 수소 또는 A) 비치환 또는 치환된 (C1-C12)―알콕시 라디칼, (C3-C8)―사이클로알콕시 라디칼, (C6-C12)―아릴옥시 라디칼 또는 (C7-C11)―아르알킬옥시 라디칼이며, 이들은 할로겐, 트리플루오로메틸,(C1-C6) ―알콕시, 하이드록실, (C1-C6)―하이드록시알킬, NR′R″ 또는 시아노에 의해 일― 또는 다치환, 바람직하게는 일― 또는 이치환되고, B) 비치환 또는 치환된, 직쇄 또는 측쇄의 지방족 또는 지환족 (C1-C12)―알킬 라디칼, (C1-C12)―알케닐 라디칼 또는 (C1-C12)―알키닐 라디칼이거나 또는 C) 비치환 또는 치환된 (C1-C12)―아릴 라디칼, (C7-C11)―아르알킬 라디칼 또는 헤트아릴 라디칼이며, R′ 및 R″는 동일하거나 상이하며 수소, (C6-C12)―아릴, (C1-C8)―알킬, (C1-C8)―알킬카보닐, (C7-C11)―아르알킬 카보닐 또는 (C6-C12)―아릴카보닐이거나, 질소원자와 함께 포화된 헤테로사이클릭 환, 바람직하게는 5― 또는 6원환을 형성하며, n은 0 또는 1이다.
- 제1항에 있어서, A는 R3이고 B는 X―NR6R7이거나, B는 R3이고 A는 X―NR6R7이며, X는 단일결합 또는 ―CO―이고, R1, R2및R3은 동일하거나 상이하며 수소, 비치환 또는 치환된 (C1-C6)―알킬, (C1-C6)―알콕시, 할로겐, 특히 불소, 염소 또는 브롬, 니티릴, 하이드록실 또는 아미노이며, R6은 수소, (C1-C6)―알킬 또는 N―보호 그룹, 예를 들면, (C1-C8)―알카노일, (C1-C6)―알킬바모일, (C1-C6)―알콕시카보닐, 벤질옥시카보닐, (C1-C10)―아실옥시―(C1-C6)―알킬, 바람직하게는 (C1-C10)―알카노일옥시―(C1-C6)―알킬, 벤조일옥시―(C1-C6)―알킬, 벤질옥시카보닐옥시―(C1-C6)―알킬 또는 (C1-C6)―알콕시카보닐옥시―알킬, (C1-C8)―알킬, (C1-C8) ―하이드록시알킬, (C1-C4)―알콕시―(C1-C8) ―알킬, 페닐, 벤질, 또는 하이드록실 또는 ―(C1-C4)-알콕시에 의해 1 내지 3회 치환될 수 있는 (C1-C8)-알킬에 의해 1 내지 3회 임의로 치환된 1-, 2-, 3-, 4가 생리학적으로 유용한 양이온, 특히 Na, K, Mg2 ,Ca2 , Al3 , 또는 암모늄 이온, 또는 염기성 아미노산 유도체의 양이온이며, R7은 -SO2H를 제외한, 하기 일반식 [Ⅱ]의 라디칼이며,―Y―〔C―U〕r―D―W (Ⅱ)[상기식에서, Y는 ―SO2― 또는 ―CO―이고, C는 결합, 또는 직쇄 또는 축쇄 지방족(C1-C16) ―알칸디일 또는 지환족(C3-C10) ―알칸디일 라디칼 또는 직쇄 또는 측쇄(C2-C16) ―알칸디일 또는 사이클로알켄디일 라디칼, 또는(C2-C16) ―알칸디일 라디칼 또는(C2-C16) ―알케닌디일 라디칼이며, 이들은 각각 하나 이상의 C―C다중 결합을 함유할 수 있고, U는 결합 또는 수소, 또는 다음 일련의 헤테로원자 그룹 ―CO―, ―O(CO)―, ―(CO)―O―, ―(CO)NR―, NR(CO)―, ―O―, ―SO―, ―SO2―, ―NR(여기에서, R은 (C1-C3)―알킬, (C1-C8)-알카노일, ((C7-C16)-아르알카노일, (C6-C12)-아로일 또는 수소이다)중의 라디칼이며, r은 1, 2, 3 또는 4이고, C는 결합 또는 수소, 또는 직쇄 또는 측쇄 지방족 (C1-C10)―알켄디일 라디칼, (C2-C10)―알킨디일 라디칼 또는 (C2-C10)―알케닌디일 라디칼이며, 이들은 각각 하나 이상의 C―C다중 결합을 함유할 수 있고, W는 결합 또는 수소, 또는 (C3-C10) ―지환족 알킬, 알케닐, 알키닐 또는 알케니닐 라디칼 또는 (C8-C10)―아릴 라디칼 또는 5― 또는 6원 헤테로아릴 라디칼이며, 여기에서 가변성분 C 또는 D 또는 W중 하나 이상은 결합이 아니고, C가 결합이 아니거나 D 및/또는 W가 결합이 아닐 경우, U는 헤테로원자 그룹일 뿐이고 ; C 및/또는 W는 , 결합 또는 수소가 아닐경우, 다음을 포함하는 시리즈중의 동일하거나 상이한 5개 이하의 치환체의 조합에 의해 이들이 바람직하게 치환되며 ; 하이드록실, 할로겐, 시아노, 트리플루오로메틸, 니트로, 카복실, (C1-C12) ―알킬, (C3-C8)―사이클로알킬, (C8-C12)―아릴, (C7-C16) ―아르알킬, (C3-C12) ―알케닐, (C3-C12) ―알키닐, (C1-C12)―알콕시, (C1-C12)―알콕시― (C1-C12)―알킬, (C1-C12)―알콕시― (C1-C12) ―알콕시, (C6-C12) ―아릴옥시, (C7-C16)―아르알킬옥시, (C1-C8)―하이드록실알킬, ―O-〔CH2〕CfH(2f+1-g)Fg, -OCF2Cl, -OCF2-CHFCl, (C1-C12)―알킬카보닐, (C3-C8)―사이클로알킬카보닐, (C8-C12)―아릴카보닐, (C7-C16)―아르알킬카보닐, 신나모일, (C3-C12)―알케닐카보닐, (C3-C12)―알키닐카보닐, (C1-C12)―알콕시카보닐, (C1-C12)―알콕시― (C1-C12)―알콕시카보닐, (C6-C12)―아릴옥시카보닐, (C7-C16)―아르알콕시 카보닐, (C3-C8)―사이클로알콕시카보닐, (C8-C12)―알케닐옥시카보닐, (C3-C12)―알키닐옥카보닐, (C3-C8)―알키닐옥시카보닐, (C1-C12)―알킬카보닐옥시, (C3-C8)―사이클로알킬카보닐옥시, (C8-C12)―아릴카보닐옥시, (C6-C12)―아르알킬카보닐옥시, 신나모일옥시 (C3-C12)―알케닐카보닐옥시, (C8-C12)―알키닐카보닐옥시, (C1-C12)―알콕시카보닐옥시, (C1-C12)―알콕시― (C6-C12)―알콕시카보닐옥시, (C7-C18)―아릴옥시카보닐옥시, (C3-C8)―아르알킬옥시카보닐옥시, (C3-C8)―사이클로알콕시카보닐옥시, (C3-C12)―알케닐옥시카보닐옥시, (C3-C12)―알키닐옥시카보닐옥시, 카바모일, N―(C1-C12) ―알킬카바모일, N,N―디―(C1-C12) ―알킬카바모일, N―(C3-C8)―사이클로알킬카바모일, N―(C6-C16) ―아릴카바모일, N―(C7-C16)―아르알킬카바모일, N―(C1-C10) ―알킬―N―(C6-C16)아릴카바모일, N―(C1-C10)―알킬―N―(C7-C16)―아르알킬카바모일, N―((C1-C10)―알콕시―(C1-C10)알킬)카바모일, N―(C6-C16) ―아릴옥시―(C1-C10)―알킬)카바모일, N―((C7-C16)―아르알킬옥시―(C1-C10)―알킬)카바모일, N―알킬―N(―아릴옥시―(C1-C10) ―알킬)카바모일, N―(C1-C10)―알킬―N―((C7-C16)―아르알킬옥시―(C1-C10)―알킬)카바모일, 카바모일옥시, N―(C1-C12)―알킬카바모일옥시,N,N―디―(C1-C12)―알킬카바모일옥시, N―(C3-C8)―사이클로알킬카바모일옥시, N―(C6-C16)―아릴카바모일옥시, N―(C7-C16)―아르알킬카바모일옥시, N―(C1-C10)―알킬―N―(C6-C12)―아릴 카바모일옥시, N―(C1-C10)―알킬―N―(C7-C16)―아르알킬카바모일옥시, N―((C1-C10)―알콕시―(C1-C10)―알킬)카바모일옥시, N―((C6-C16)―아릴옥시―(C1-C10) ―알킬)카바모일옥시, N―((C7-C16)―아르알킬옥시―(C1-C10)―알킬)카바모일옥시, N―(C1-C10) ―알킬―N―((C1-C10)―알콕시―(C1-C10)―알킬)카바모일옥시,N―(C1-C10)-알킬―N―((C6-C16)―아릴옥시―((C1-C10) ―알킬) 카바모일옥시, N―(C1-C10)―알킬―N―((C7-C16)―아르알킬옥시―(C1-C10) ―알킬)카바모일옥시, 아미노, (C1-C12)―알킬아미노, 디―(C1-C12) ―알킬아미노, (C3-C8)―사이클로알킬아미노, (C3-C12)―알케닐아미노, (C3-C12)―알키닐아미노, N―(C6-C12) ―아릴아미노, N―(C7-C11) ―아르알킬아미노, N―(C1-C10)―알킬―(C7-C10)―아르알킬아미노, N―(C1-C10)―알킬―N―(C6-C12)―알킬아미노, (C1-C12)―알콕시아미노, (C1-C12)―알콕시―N―(C1-C10)―알킬아미노, (C1-C12)―알카노일아미노, (C3-C8)―사이클로알카노일아미노, (C6-C12)―아로일아미노, (C7-C16) ―아르알카노일아미노, (C1-C12)―알카노일―N―(C1-C10)―알킬아미노, (C3-C8) ―사이클로알칸노일―N―(C1-C10)-알킬아미노, (C6-C12)―아로일―N―(C1-C10) ―알킬아미노, (C7-C11)―아르알카노일―N―(C1-C10)―알킬아미노, (C1-C12)―알카노일아미노―(C1-C8)―알킬, (C3-C8)―사이클로알카노일아미노―(C1-C8) ―알킬, (C6-C16)―아로일아미노―(C1-C8)―알킬,(C7-C16)―아르알카노일아미노―(C1-C8)―알킬, 아미노―(C1-C10) ―알킬, N―(C1-C10)―알킬아미노―(C1-C10)―알킬, N,N―디―(C1-C10)―알킬아미노―(C1-C10) ―알킬아미노―(C1-C10)―알킬, (C3-C8)―사이클로알킬아미노―(C1-C10)―알킬, (C1-C12)―알킬머캅토, (C1-C12)―알킬설피닐, (C1-C12)―알킬설포닐, (C6-C16)―아릴머캅토, (C6-C16)―아릴설피닐, (C6-C16)―아릴설포닐, (C7-C16)―아르알필머캅토, (C7-C16)―아르알킬설피닐, (C7-C16)―아르알킬설포닐, 설파모일, N―(C1-C10)―알킬설파모일, N,N―디―(C1-C10)―알킬설파모일, (C3-C8)―사이클로알킬설파모일, N―(C6-C16)―아릴설파모일, N―(C7-C16)―아르알킬설파모일, ―(C1-C10)―아킬―N―(C6-C16)―아릴설파모일, N―(C1-C10) ―알킬―N―(C7-C16)아르알킬설파모일, (C1-C10)―알킬설폰아미도, N―((C1-C10)―알킬―(C1-C10)알킬설폰아미도, (C7-C16)알킬설폰아미도, N―((C1-C10알킬-((C7-C16)아르알킬설폰아미도, 여기에서, 아릴 라디칼을 함유하는 라디칼은 이의 아릴 부위상에서 다음을 포함하는 시리즈중의 동일하거나 상이한 치환체 1 내지 5개에 의해 일부가 치환될 수 있으며 : 하이드록실, 할로겐, 시아노, 트리플루오로메틸, 니트로, 카복실, (C1-C12)―알킬, (C3-C8)―사이클로알킬, (C6-C12)―아릴, (C7-C16)―아르알킬, (C3-C12)―알케닐, (C3-C12)―알키닐, (C1-C12)―알콕시, (C1-C12)―알콕시―(C1-C12)―알킬, (C1-C12)―알콕시― (C1-C12) ―알콕시, (C6-C12)―아릴옥시, (C7-C16)―아르알킬옥시, (C1-C8)―하이드록시알킬, ―O―[CH2]xCfH(2f+1=g)-OCF2Cl, -OCF2-CHFCl, (C1-C12)―알킬카보닐, (C3-C8)―사이클로알킬카보닐, (C6-C12)―아릴카보닐, (C7-C16)―아르알킬카보닐, 신나모일, (C3-C12)―알케닐카보닐, (C3-C12)―알키닐카보닐, (C1-C12)―알콕시카보닐, (C1-C12)―알콕시―(C1-C12)―알콕시카보닐, (C1-C12)―알콕시카보닐, (C1-C12)―알콕시―(C1-C12)―알콕시카보닐, (C6-C10)―아릴옥시카보닐, (C7-C16)―아르알콕시카보닐; (C3-C8)―사이클로알콕시카보닐, (C3-C12)―알케닐옥시카보닐, (C3-C12)―사이클로알콕시카보닐, (C1-C12)―알킬카보닐옥시, (C3-C8)―사이클로알킬카보닐옥시, (C6-C12)―아릴카보닐옥시, (C7-C16)―아르알킬카보닐옥시, 신나모일옥시, (C3-C12)―알키닐카보닐옥시, (C1-C12)―알콕시카보닐옥시, (C1-C12)―알콕시―(C1-C12)―알콕시카보닐옥시, (C6-C12)―아릴옥시카보닐옥시, (C7-C16)―아르알킬옥시카보닐옥시, (C3-C8)―사이클로알콕시카보닐옥시, (C3-C12)―알케닐옥시카보닐옥시, (C3-C12)―알키닐옥시카보닐옥시, 카바모일, N―(C1-C12)―알킬카바모일, N,N―디―(C1-C12)―알킬카바모일, N―(C3-C8)―사이클로알킬카바모일, N―(C6-C16)아릴카바모일, N―(C7-C16)아르알킬카바모일, N―(C1-C10)―알킬―N―(C6-C16)―아릴카바모일, N―(C1-C10)―알킬―N―(C7-C16)―아르알킬카바모일, N―((C1-C10)―알콕시―(C1-C10)―알킬)카바모일,N-((C6-C16)-아릴옥시-(C1-C10))-알킬)카바모일), N-((C7-C16)-아르알킬옥시-(C1-C10)-알킬)카바모일, N-((C1-C12)-알킬-N((C1-C10)-아릴옥시-(C1-C10)-알킬)카바모일, N-((C1-C10)-알킬-N(-아릴옥시-(C1-C10)-알킬)카바모일, N-((C6-C16)-아릴옥시-(C1-C10)-알킬)카바모일, N―(C1-C10-)알킬)카바모일,N-((C7-C16)-아르알킬옥시-(C1-C10)-알킬)카바모일,카바모일옥시,N-(C1-C12)―알킬카바모일옥시,N,N-디-(C1-C12)-알킬카바모일옥시, N-(C3-C8)-사이클로알킬카바모일옥시, N-(C6-C16)-아릴카바모일옥시, N-(C7-C16)- 아르알킬카바모일옥시, N―(C1-C10)―알킬-N-(C6-C12)-아릴카바모일옥시, N―(C1-C10)―알킬-N-(C6-C12)-아르알킬카바모일옥시, N―(C1-C10)―알콕시-(C1-C10)-알킬)카바모일옥시, N―(C6-C16)-아릴옥시-(C1-C10)-알킬)카바모일옥시, N-((C7-C16)-아르알킬옥시-(C1-C10)-알킬)카바모일옥시, N―(C1-C10)-알킬-N-((C1-C10)-알콕시-(C1-C10)-알킬)카바모일옥시, N―(C1-C10)-알킬-N-((C6-C16)-아릴옥시-(C1-C10)-알킬)카바모일옥시, N―(C1-C10)-알킬-N-((C7-C16)-아르알킬옥시-(C1-C10)-알킬)카바모일옥시, 아미노, (C1-C12)-알킬아미노, 디-(C1-C12)-알킬아미노, (C3-C8)-사이클로알킬아미노, (C3-C12)-알케닐아미노, (C3-C12)-알키닐아미노, N-(C6-C12)-아릴아미노, N-(C7-C11)-아르알킬아미노, N―(C1-C10)-알킬-(C7-C16)-아르알킬아미노, N―(C1-C10)-알킬-(C6-C12)-알킬아미노, (C1-C12)-알콕시아미노, (C1-C12)-알콕시-N-(C1-C10)-알킬아미노, (C1-C12)-알카노일아미노, (C3-C8)-사이클로알킬아미노, (C6-C12)-아로일아미노, (C7-C16)-아르알카노일아미노, (C1-C12)-알카노일-N-(C1-C10)-알킬아미노, (C3-C8)-사이클로알킬아미노-N-(C1-C10)-알킬아미노, (C6-C12)-아로일-N-(C1-C10)-알킬아미노, (C7-C11)-아르알카노일-N-(C1-C10)-알킬아미노, (C1-C12)-알카노일아미노-(C1-C8)-알킬, (C3-C8)-사이클로알킬아미노-(C1-C8)-알킬, (C6-C16)-아로일아미노-(C1-C8)-알킬, (C7-C16)-아르알카노일아미노-(C1-C8)-알킬, 아미노-(C1-C10)-알킬, N-(C1-C10)-알킬아미노-(C1-C10)-알킬, N,N-디-(C1-C10)-알킬아미노-(C1-C10)-알킬아미노-(C1-C10)-알킬, (C3-C8)-사이클로알킬아미노-(C1-C10)-알킬, (C1-C12)-알킬커갑토, (C1-C12)-알킬설피닐, (C1-C12)-알킬설포닐, (C1-C16)-아릴머갑토, (C6-C16)-아릴설피닐, (C6-C16)-아릴설포닐, (C7-C16)-아르알킬머갑토, (C7-C16)-아르알킬설피닐, (C7-C16)-아르알킬설포닐, 설포마일, N-(C1-C10)-알킬설파모일, N,N-디-(C1-C10)-알킬설파모일, (C3-C8)-사이클로알킬설파모일, N-(C6-C16)-아릴설파모일, N-(C7-C16)-아르알킬설파모일, N-(C1-C10)-아킬-N-(C6-C16)-아릴설파모일,N-(C1-C10)-알킬-N-(C7-C16)아르알킬설파모일, (C1-C10)-알킬설폰아미도, N-((C1-C10)-알킬)-(C1-C10)-알킬설폰아미도, (C7-C16)-아르알킬설폰아미도, N-((C1-C10)-알킬)-(N-((C1-C10)-알킬)-아르알킬설폰아미도, 여기에서, 아릴 라디칼을 함유하는 라디칼은 이의 아릴 부위상에서 다음을 포함하는 시리즈중의 동일하거나 상이한 치환체 1 내지 5개에 의해 일부가 치환될 수 있으며 : 하이드록실, 할로겐, 시아노, 트리플루오로메틸, 니트로, 카복실, (C1-C12)-알킬, (C3-C8)―사이클로알킬, (C6-C12)-아릴, (C7-C16)-아르알킬, (C3-C12)-알케닐, (C3-C12)-알키닐, (C1-C12)-알콕시, (C1-C12)-알콕시-(C1-C12)-알킬, (C1-C12)-알콕시-(C1-C12)-알콕시, (C6-C12)-아릴옥시, (C7-C16)-아르알킬옥시, (C1-C8)-하이드록시알킬, -O-〔CH2〕CfH(2f+1-g)Fg-OCF2Cl,-OCF2-CHFCl, (C1-C12)―알킬카보닐, (C3-C8)-사이클로알킬카보닐, (C6-C12)-아릴카보닐, (C7-C16)-아르알킬카보닐, 신나모일, (C3-C12)-알키닐카보닐, (C3-C12)-알콕시카보닐, (C1-C12)-알콕시-(C1-C12)-알콕시카보닐, (C1-C12)-알콕시카보닐, (C1-C12)-알콕시-(C1-C12)-알콕시카보닐, (C6-C10)-아릴옥시카보닐, (C7-C16)-아르알콕시카보닐, (C3-C8)-사이클로알코시카보닐, (C3-C12)-알케닐오시카보닐, (C3-C12)-사이클로알콕시카보닐, (C1-C12)-알킬카보닐옥시, (C3-C8)-사이클로알킬카보닐옥시, (C6-C12)-아릴카보닐옥시, (C7-C16)-아르알킬카보닐 옥시, 신나모일옥시, (C3-C12)-알키닐카보닐옥시, (C1-C12)-알콕시카보닐옥시, (C1-C12)-알콕시-(C1-C12)-알콕시카보닐옥시, (C6-C12)-아릴옥시카보닐옥시, (C7-C16)-아르알킬옥시카보닐옥시, (C3-C8)-사이클로알콕시카보닐옥시, (C3-C12)-알케닐옥시카보닐옥시, (C3-C12)-알키닐옥시카보닐옥시, 카바모일, N-(C1-C12)-알킬카바모일, N.N-디-(C1-C12)-알킬카바모일, N-(C3-C8)-사이클로알킬카바모일, N-(C6-C16)-아릴카바모일, N-(C7-C16)-아르알킬카바모일, N―(C1-C10)―알킬-N-(C6-C16)-아릴카바모일, N―(C1-C10)―알킬-N-(C7-C16)-아르알킬카바모일, N-((C1-C10)-알콕시-(C1-C10)-알킬)카바모일, N―((C6-C16)-아릴옥시-(C1-C10)-알킬)카바모일, N-((C7-C16)-아르알킬옥시-(C1-C10)-알킬)카바모일, 카바모일옥시, N―(C1-C12)―알킬카바모일옥시,N,N-디-(C1-C12)-알킬카바모일옥시, N-(C3-C8)-사이클로알킬카바모일옥시, N-(C6-C16)-아릴카바모일옥시, N-(C1-C10)-알킬-N(C6-C12)-알칼카바모일옥시 N―(C1-C10)―알킬-N-(C6-C12)-아릴카바모일옥시, N―(C1-C10)―알킬-N-(C7-C16)-아르알킬카바모일옥시,N-((C1-C10)-알콕시-(C1-C10)-알킬)카바모일옥시, N―(C6-C16)-아릴옥시-(C1-C10)-알킬)카바모일옥시, (C7-C16)-아르알킬옥시-(C1-C10)-알킬)카바모일옥시, N―(C1-C10)-알킬-N-((C1-C10)-알콕시-(C1-C10)-알킬)카바모일옥시, N―(C1-C10)-알킬-N-((C6-C16)-아릴옥시-(C1-C10)-알킬)카바모일옥시, N―(C1-C10)-알킬-N-((C7-C16)-아르알킬옥시-(C1-C10)-알킬)카바모일옥시, 아미노, (C1-C12)-알킬아미노, 디-(C1-C12)-알킬아미노, (C3-C8)-사이클로알킬아미노, (C3-C12)-알케닐아미노, (C3-C12)-알키닐아미노, N-(C6-C12)-아릴아미노, N-(C7-C11)-아르알킬아미노, N―(C1-C10)-알킬-(C7-C16)-아르알킬아미노, N―(C1-C10)-알킬-N-(C6-C12)-아릴아미노, (C1-C12)-알콕시아미노, (C1-C12)-알콕시-N-(C1-C10)-알킬아미노, (C1-C12)-알카노일아미노, (C3-C8)-사이클로알카노일아미노, (C6-C12)-아로일아미노, (C7-C18)-아르알카노일아미노, (C1-C12)-알카노일-N-(C1-C10)-알킬아미노, (C3-C8)-사이클로카노일-N-(C1-C10)-알킬아미노, (C6-C12)-아로일-N-(C1-C10)-알킬아미노, (C7-C11)-아르알카노일-N-(C1-C10)-알킬아미노, (C1-C12)-알카노일아미노-(C1-C8)-알킬, (C3-C8)-사이클로알킬카노일아미노-(C1-C8)-알킬, (C6-C16)-아로일아미노-(C1-C8)-알킬, (C7-C16)-아르알카노일아미노-(C1-C8)-알킬, 아미노-(C1-C10)-알킬, N-(C1-C10)-알킬아미노-(C1-C10)-알킬, N,N-디-(C1-C10)-알킬아미노-(C1-C10)-알킬아미노-(C1-C10)-알킬, (C3-C8)-사이클로알킬아미노-(C1-C10)-알킬, (C1-C12)-알킬머갑토, (C1-C12)-알킬설피닐, (C1-C12)-알킬설포닐, (C1-C16)-아릴머갑토, (C6-C16)-아릴설포닐, (C7-C16)-아르알킬머갑토, (C7-C16)-아르알킬설피닐, (C7-C16)-아르알킬설포닐, 설파모일, N-(C1-C10)-알킬설파모일, N,N-디-(C1-C10)-알킬설파모일, (C3-C8)-사이클로알킬설파모일, N-(C6-C16)-아릴설파모일, N-(C7-C16)-아르알킬설파모일, N-(C1-C10)-알킬-N-(C6-C16)-아릴설파모일,N-(C1-C10)-알킬-N-(C7-C16)-아르알킬설파모일, (C1-C10)-알킬설폰아미도, N-((C1-C10)-알킬)-(C1-C10)-알킬설폰아미도, (C7-C16C7-C16)-아르알킬설폰아미도, R4및 R5는 서로 독립적으로 수소 또는 A) 비치환 또는 치환된 (C1-C12)-알콕시 라디칼, (C3-C8)-사이클로알콕시 라디칼, (C6-C12)-아릴옥시 라디칼 또는( C7-C11)-아르알킬옥시 라디칼이며, 이들은 할로겐, 트리플루오로메틸,
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4209424 | 1992-03-24 | ||
DE?P4209424.0? | 1992-03-24 | ||
DE?P4238506.7? | 1992-11-14 | ||
DE4238506 | 1992-11-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
KR930019630A true KR930019630A (ko) | 1993-10-18 |
Family
ID=25913130
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019930004589A KR930019630A (ko) | 1992-03-24 | 1993-03-24 | 셀폰아미도- 및 셀폰아미도카보닐피리딘-2-카복스아미드 및 이의 피리딘-n-옥사이드, 이의 제조방법 및 약제로서 이의용도 |
Country Status (24)
Country | Link |
---|---|
US (1) | US5607954A (ko) |
EP (1) | EP0562512B1 (ko) |
JP (1) | JPH0649030A (ko) |
KR (1) | KR930019630A (ko) |
CN (1) | CN1076691A (ko) |
AT (1) | ATE199250T1 (ko) |
AU (1) | AU657608B2 (ko) |
CA (1) | CA2092276A1 (ko) |
CZ (1) | CZ46393A3 (ko) |
DE (1) | DE59310146D1 (ko) |
DK (1) | DK0562512T3 (ko) |
ES (1) | ES2154266T3 (ko) |
FI (1) | FI102895B1 (ko) |
GR (1) | GR3035479T3 (ko) |
HK (1) | HK1011987A1 (ko) |
HU (2) | HU219224B (ko) |
MY (1) | MY109143A (ko) |
NO (1) | NO179867C (ko) |
NZ (1) | NZ247201A (ko) |
PL (1) | PL173677B1 (ko) |
PT (1) | PT562512E (ko) |
RU (1) | RU2129545C1 (ko) |
SK (1) | SK280884B6 (ko) |
TW (1) | TW352384B (ko) |
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EP0650960B1 (de) * | 1993-11-02 | 1997-03-05 | Hoechst Aktiengesellschaft | Substituierte heterocyclische Carbonsäureamidester, ihre Herstellung und ihre Verwendung als Arzneimittel |
ATE149486T1 (de) * | 1993-11-02 | 1997-03-15 | Hoechst Ag | Substituierte heterocyclische carbonsäureamide, ihre herstellung und ihre verwendung als arzneimittel |
NZ270267A (en) * | 1993-12-30 | 1997-03-24 | Hoechst Ag | 3-hydroxypyridin-2yl (and -quinolin-2-yl) carboxamide derivatives and pharmaceutical compositions |
DE4410480A1 (de) * | 1994-03-25 | 1995-09-28 | Hoechst Ag | Sulfonamidocarbonylpyridin-2-carbonsäureesteramide sowie ihre Pyridin-N-oxide, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
DE4410423A1 (de) * | 1994-03-25 | 1995-09-28 | Hoechst Ag | Sulfonamidocarbonylpyridin-2-carbonsäureamide sowie ihre Pyridin-N-oxide, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
DE4410454A1 (de) * | 1994-03-25 | 1995-09-28 | Hoechst Ag | Substituierte heterocyclische Carbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel |
DE4410453A1 (de) * | 1994-03-25 | 1995-09-28 | Hoechst Ag | Substituierte heterocyclische Carbonsäureamidester, ihre Herstellung und ihre Verwendung als Arzneimittel |
IL135495A (en) * | 1995-09-28 | 2002-12-01 | Hoechst Ag | Intermediate compounds for the preparation of quinoline-converted amines - 2 - carboxylic acid |
DE19742951A1 (de) | 1997-09-29 | 1999-04-15 | Hoechst Schering Agrevo Gmbh | Acylsulfamoylbenzoesäureamide, diese enthaltende nutzpflanzenschützende Mittel und Verfahren zu ihrer Herstellung |
DE19746287A1 (de) * | 1997-10-20 | 1999-04-22 | Hoechst Marion Roussel De Gmbh | Substituierte Isochinolin-2-Carbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel |
AR015733A1 (es) * | 1998-03-25 | 2001-05-16 | Otsuka Pharma Co Ltd | DERIVADO DE PIRIDINA, EL PRODUCTO Y LA COMPOSICIoN FARMACEUTICA QUE CONTIENE DICHO DERIVADO. |
US6583318B2 (en) | 2001-05-17 | 2003-06-24 | Advanced Syntech, Llc | Method for synthesis of α-sulfonamido amide, carboxylic acid and hydroxamic acid derivatives |
EP2295060B1 (en) | 2001-12-06 | 2018-10-31 | Fibrogen, Inc. | Treatment or prevention of ischemic or hypoxic conditions |
ES2414706T3 (es) | 2001-12-06 | 2013-07-22 | Fibrogen, Inc. | Métodos para aumentar la eritropoyetina endógena |
US8124582B2 (en) | 2002-12-06 | 2012-02-28 | Fibrogen, Inc. | Treatment of diabetes |
US7618940B2 (en) | 2002-12-06 | 2009-11-17 | Fibrogen, Inc. | Fat regulation |
US8614204B2 (en) * | 2003-06-06 | 2013-12-24 | Fibrogen, Inc. | Enhanced erythropoiesis and iron metabolism |
WO2006138511A2 (en) | 2005-06-15 | 2006-12-28 | Fibrogen, Inc. | Use of hif 1alfa modulators for treatment of cancer |
KR100934674B1 (ko) * | 2006-03-30 | 2009-12-31 | 엘지전자 주식회사 | 비디오 신호를 디코딩/인코딩하기 위한 방법 및 장치 |
EP3026044B8 (en) | 2006-06-26 | 2018-12-19 | Akebia Therapeutics, Inc. | Prolyl hydroxylase inhibitors and methods of use |
WO2008147797A2 (en) * | 2007-05-25 | 2008-12-04 | Vertex Pharmaceuticals Incorporated | Ion channel modulators and methods of use |
WO2009002533A1 (en) * | 2007-06-27 | 2008-12-31 | The Brigham And Women's Hospital, Inc. | Inflammatory bowel disease therapies |
NO2686520T3 (ko) | 2011-06-06 | 2018-03-17 | ||
RU2627701C2 (ru) | 2012-02-22 | 2017-08-10 | Сэнфорд-Бёрнхэм Медикал Рисёрч Инститьют | Сульфонамидные соединения и их применение в качестве ингибиторов tnap |
TW201512171A (zh) | 2013-04-19 | 2015-04-01 | Pfizer Ltd | 化學化合物 |
CN114404414A (zh) | 2013-06-13 | 2022-04-29 | 阿克比治疗有限公司 | 用于治疗贫血症的组合物和方法 |
TWI665190B (zh) | 2013-11-15 | 2019-07-11 | 阿克比治療有限公司 | {[5-(3-氯苯基)-3-羥基吡啶-2-羰基]胺基}乙酸之固體型式,其組合物及用途 |
US10150734B2 (en) | 2015-01-23 | 2018-12-11 | Akebia Therapeutics, Inc. | Solid forms of 2-(5-(3-fluorophenyl)-3-hydroxypicolinamido)acetic acid, compositions, and uses thereof |
CN106146395B (zh) * | 2015-03-27 | 2019-01-01 | 沈阳三生制药有限责任公司 | 3-羟基吡啶化合物、其制备方法及其制药用途 |
BR112017021097B1 (pt) | 2015-04-01 | 2024-01-02 | Akebia Therapeutics, Inc | Formulação de dosagem oral e seu uso |
TW202406895A (zh) | 2018-05-09 | 2024-02-16 | 美商阿克比治療有限公司 | 用於製備2-[[5-(3-氯苯基)-3-羥基吡啶-2-羰基]胺基]乙酸之方法 |
US11524939B2 (en) | 2019-11-13 | 2022-12-13 | Akebia Therapeutics, Inc. | Solid forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino} acetic acid |
CN111972405A (zh) * | 2020-07-27 | 2020-11-24 | 南京太化化工有限公司 | 一种悬浮剂用助剂及异恶唑草酮悬浮剂 |
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Publication number | Priority date | Publication date | Assignee | Title |
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DE3432094A1 (de) * | 1984-08-31 | 1986-03-06 | Hoechst Ag, 6230 Frankfurt | Ester der pyridin-2,4- und -2,5- dicarbonsaeure als arzneimittel zur inhibierung der prolin- und lysinhydroxylase |
DE3703959A1 (de) * | 1987-02-10 | 1988-08-18 | Hoechst Ag | Pyridin-2,4- und 2,5-dicarbonsaeureamide, verfahren zu ihrer herstellung, verwendung derselben sowie arzneimittel auf basis dieser verbindungen |
US5153208A (en) * | 1987-02-10 | 1992-10-06 | Hoechst Aktiengesellschaft | Pyridine-2,4- and -2,5-dicarboxylic acid amides and their medicinal compositions and methods of use |
DE3703962A1 (de) * | 1987-02-10 | 1988-08-18 | Hoechst Ag | Pyridin-2,4- und 2,5-dicarbonsaeure-derivate, verfahren zu ihrer herstellung, verwendung derselben sowie arzneimittel auf basis dieser verbindungen |
DE3928144A1 (de) * | 1989-08-25 | 1991-02-28 | Hoechst Ag | Zyklische pyridin-2,4- und -2,5-dicarbonsaeurediamide, verfahren zu deren herstellung sowie deren verwendung |
DE4020570A1 (de) * | 1990-06-28 | 1992-01-02 | Hoechst Ag | 2,4- und 2,5-substituierte pyridin-n-oxide, verfahren zu deren herstellung sowie deren verwendung |
-
1993
- 1993-03-09 TW TW082101698A patent/TW352384B/zh active
- 1993-03-19 NZ NZ247201A patent/NZ247201A/xx unknown
- 1993-03-22 CZ CZ93463A patent/CZ46393A3/cs unknown
- 1993-03-22 ES ES93104658T patent/ES2154266T3/es not_active Expired - Lifetime
- 1993-03-22 DK DK93104658T patent/DK0562512T3/da active
- 1993-03-22 SK SK223-93A patent/SK280884B6/sk unknown
- 1993-03-22 AT AT93104658T patent/ATE199250T1/de not_active IP Right Cessation
- 1993-03-22 MY MYPI93000506A patent/MY109143A/en unknown
- 1993-03-22 PT PT93104658T patent/PT562512E/pt unknown
- 1993-03-22 DE DE59310146T patent/DE59310146D1/de not_active Expired - Fee Related
- 1993-03-22 EP EP93104658A patent/EP0562512B1/de not_active Expired - Lifetime
- 1993-03-22 FI FI931250A patent/FI102895B1/fi active
- 1993-03-23 RU RU93004764A patent/RU2129545C1/ru active
- 1993-03-23 NO NO931056A patent/NO179867C/no not_active IP Right Cessation
- 1993-03-23 AU AU35369/93A patent/AU657608B2/en not_active Ceased
- 1993-03-23 PL PL93298195A patent/PL173677B1/pl unknown
- 1993-03-23 JP JP5063723A patent/JPH0649030A/ja active Pending
- 1993-03-23 CA CA002092276A patent/CA2092276A1/en not_active Abandoned
- 1993-03-23 CN CN93103349A patent/CN1076691A/zh active Pending
- 1993-03-24 HU HU9300850A patent/HU219224B/hu not_active IP Right Cessation
- 1993-03-24 KR KR1019930004589A patent/KR930019630A/ko not_active Application Discontinuation
-
1994
- 1994-12-13 US US08/355,419 patent/US5607954A/en not_active Expired - Fee Related
-
1995
- 1995-01-17 HU HU95P/P00068P patent/HU210714A9/hu unknown
-
1998
- 1998-12-11 HK HK98113239A patent/HK1011987A1/xx not_active IP Right Cessation
-
2001
- 2001-02-28 GR GR20010400321T patent/GR3035479T3/el not_active IP Right Cessation
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