KR850008489A - 세팔로스포린 유도체의 제법 - Google Patents
세팔로스포린 유도체의 제법 Download PDFInfo
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- KR850008489A KR850008489A KR1019850003778A KR850003778A KR850008489A KR 850008489 A KR850008489 A KR 850008489A KR 1019850003778 A KR1019850003778 A KR 1019850003778A KR 850003778 A KR850003778 A KR 850003778A KR 850008489 A KR850008489 A KR 850008489A
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- alkyl
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- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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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- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having 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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- C07D277/587—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 aliphatic hydrocarbon radicals substituted by 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, said aliphatic radicals being substituted in the alpha-position to the ring by a hetero atom, e.g. with m >= 0, Z being a singly or a doubly bound hetero atom
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Abstract
내용 없음
Description
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Claims (21)
- (a) 일반식(53)의 화합물을 대체 가능한 기인 일반식 R5-R40화합물과 반응시키고, (b) 다음 일반식(54)의 화합물을 다음 일반식(55)의 산 또는 그의 활성화 유도체와 반응시키고, (c) 카복시를 형성하기 위해, 카복시의 산성수소원자 대신에 보호그룹을 가지는 상응하는 화합물을 탈 보호하고, (d) 1차 또는 2차아미노를 형성하기 위해, 아미노수소 대신 보호그룹을 가지는 상응하는 화합물을 탈보호하고, (e) x가 설피닐인 화합물을 위해, x가 황인 상용하는 화합물을 산화하고, (f) 일반식 (56)의 화합물을 일반식 R2-0-NH2의 화합물과 반응시키고, (g) R2가 수소가 아닌 다른것일 경우의 화합물을 위해서, 일반식(1)의 화합물(R2가 수소)을 일반식 R41-R40(R40은 대체가능한 기이고 R41은 수소를 제외한 하기하는 R2에 대한 값중의 하나이다)와 반응시키고, (h) 아미노페닐 그룹을 함유하는 화합물을 위해, 상응하는 니트로페닐 화합물을 환원시키고, (i) R40이 대체가능한 기인 일반식(58)이 화합물을 일반식 R4R5NH와 반응시키는 것으로 구성된, 다음 일반식(1)이 세팔로스포린 유도체이 제조방법.
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- 식중, X는 황, 산소, 메틸렌 또는 설피닐((R 또는 S배열), R1은 각각 임의적으로 5-위치에 불소, 염소 또는 브롬으로 치환된 2-아미노티아졸-4-일 또는 2-아미노옥사졸-4-일이거나, R1은 5-아미노이소티아졸-3-일, 5-아미노-1,2,4-티아디아졸-3-일, 3-아미노피라졸-5-일, 3-아미노피아라졸-4-일, 2-아미노피리미딘-5-일, 2-아미노피리드-6-일, 4-아미노피리미딘-2-일, 2-아미노-1,3,4-티아디아졸-5-일 또는 5-아미노-1-메틸-1,2,4-티아졸-3-일이다; R50은 클로로메틸렌 또는 일반식 N.O.R2(R2는 수소, C1-6알킬, C3-8싸이클로알킬, C1-3알킬, C3-6싸이클로알킬, C3-6싸클로알킬 C1-3알킬, C3-6알케닐(카복시로 임의로 치환된), C5-8싸이클로알케닐, C3-6알키닐, C2-5알킬카바모일, 페닐카바모일, 벤질카바모일, C1-4알킬카바모일 C1-4알킬, 디 C1-4알킬카바모일 C1-4알킬, C1-4할로알킬카바모일 C1-4알킬, 트리페닐메틸, C1-3할로알킬, C2-6하이드록시알킬, C1-4알콕시 C2-4알킬, C1-4알킬티오 C1-4알킬, C1-4알칸-설피닐 C1-4알킬, C1-4알칸-설피닐, C1-4알킬,C2-6아미노알킬, 알킬아미노 C1-6알킬, C2-8디 알킬아미노 C2-6알킬, C1-5시아노알킬, 3-아미노-3-카복시프로필, 2-아미디노티오)에틸, 2-(N-아미노아미디노티오)에틸, 테트라하이드로피란-2-일, 티에탄-3-일, 2-옥소피롤리디닐 또는 2-옥소테트라하이드로푸란-3-일 또는 -R2는 일반식-(CH2)n-R6(n은 1-4이고 R6는 피페리디노, 피롤리디노, 모르폴리노, 피페라지노 또는 N-메틸피페라지노이며 각 R6는 임의로 C1-4알킬, 페닐 또는 벤질로 치환될 수 있다).
- 또는 -R2는 일반식 -(CH2)m-W-R7(m은 0-3이고 W는 황 또는 직접 결합이고 R7은 페닐 또는 피리디니오 C1-4알킬렌 또는 R7은 피리딜, 이미다졸릴, 1,3,4-티아디아졸릴, 테트라졸릴, 1-C1-4알킬테트라졸릴, 티아졸릴, 이소티아졸릴 또는 이소옥사졸릴이며, 결합 W는 탄소 또는 비하전된 질소를 통해 연결되며 각 R7은 임의로(가능한 경우)C1-4알킬, 아미노, 하이드록시, 카복시, 카바모일, 니트로, C2-5알콕시카보닐, 시아노 또는 설포로부터 선택한 한 개 또는 두 개 그룹에 의해 치환된다).
- 또는 -R2는 일반식 -(CH2)n-CO-R8(n은 1-4이고, R8은 C1-4알킬, 페닐 또는 벤질). 또는 -R2는 일반식 -COR9또는 -(CH2)n-OCO-R9(n은 1-4이고, R9는 C1-4알킬, C1-4할로알킬, 페닐 또는 벤질). 또는 -R2는 일반식 -G-CH1-R10(G는 카보닐 또는 직접 결합이고 R10은 프탈이미도). 또는 -R2는 일반식 - 11R12R13(R11, R12, R13은 C1-4알킬이거나, R11은 C1-4알킬이고 R12와 R13이 결합하여 C3-6카보싸이클환을 형성하거나, R11, R12및 R13이 결합하여 1-아조니아-4-아자바이싸이클로 [2,2,2] 옥탄 또는 1-아조니아-3,5,7-트라아자트리싸이클로 [3,3,1,1,3,7] 메칸을 형성한다. 또는 -R2는 다음 일반식(2)
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- (P는 1 또는 2이고, R14및 R15는 수소 또는 C1-4알킬) 또는, -R12는 일반식 -P(0)R16RR17(R16은 하이드록시, C1-4알콕시, C2-8디알킬아미노, 페녹시, 페닐아미노 또는 상기 R6에 정의된 것중 하나이고 R17은 C1-4알킬, C1-4알콕시 C2-8디알킬아미노, 페녹시, 페닐아미노, 피페리디노, 피롤리디노, 모르폴리노, 피페라지노 또는 N-메틸피페라지노이다. 또는, -R2는 일반식 -CH2P(O)R18R19R18및 R19는 하이드록시 또는 C1-4알콕시이거나 -R2는 일반식 -CH(SR20)COOR21(R20은 C1-4알킬이고 R21은 수소 또는 C1-6알킬)이거나, -R2은 다음 일반식(3)
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- (m은 0-3, R22는 수소, C1-3알킬 또는 메틸티오, R25은 수소, C1-3알킬, C3-7싸이클로알킬, 시아노, 카복시, C2-5카복시알킬 또는 메탄설포닐아미노, 또는 임의로 아미노나 하이드록시로 치환된 페닐 또는 R22및 R23은 함께 결합하여 탄소와 연결된 C3-7카보싸이클환을 형성하고, R24는 하이드록시, 아미노, C1-4알콕시, C1-4알킬아미노, 페닐아미노 또는 상기한 일반식 R6의 정의된 것이거나 일반식 NHOR25, 여기시 R26은 수소, C1-4알킬, 페닐 또는 벤질인데(단 R2가 페닐을 함유하는 경우), 별다른 언급이 없는한 페닐은 할로겐, 하이드록시, 아미노, 카복시, 니트로, 카바모일, 시아노 및 아미노메틸로부터 선택한 1 또는 2개그룹으로 치환된다) ; R3는 수소 또는 메톡시 ; R4는 수소, C1-4알킬, 할로 C1-4알킬, 하이드록시 C1-4알킬, C1-4알콕시 C1-4알킬, 카복시 C1-4알킬, 아미노 C1-4알킬, 시아노 C1-4알킬, C1-4알카노일아미노 C1-4알킬, 알릴, 푸르푸릴, 벤질 또는 피리딜 C1-4알킬 : R5는 탄소원자에 연결된 방향족 헤테로싸이클 환시스템 및 다음 일반식(4)에서 일반식(51)까지중 어느 하나이다.
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- 이러한 각각의 환 시스템은 (가능하면)수소, C1-6알킬, 카복시, C2-6알콕시카보닐, C2-6알콕시카보닐 C1-4알킬, C1-6알콕시, C1-6알킬티오, 시아노, C2-4시아노알킬, 아미노, C1-6알킬아미노, C2-8디알킬아미노, 벤질아미노(임의적으로 벤젠환이 니트로로 치환된), 테닐아미노, 알릴아미노, C1-6아미노알킬아미노, C1-6알콕시 C1-6알킬아미노, 하이드록시알킬아미노, 하이드록시, 메르캅토, 카바모일, C2-6알킬카부모일, C3-6디알킬카바모일, 페닐티오 및 헤테로아릴티오(헤테로아릴은 산소, 질소 및 황으로부터 선택한 1,2 또는 3개의 헤테로원자를 함유하는 5-또는 6-원환)로부터 선택한 1,2 또는 3개의 치환체에 의해 탄소원자 또는 원자상에서 임의로 치환될 수 있다 ; Y는 산소, 황, 또는 NR27; Z는 질소 또는 CH; A, B, D 및 E의 하나는 +NR27이며 나머지는 질소이다 ; 일반식(4), (6) 또는 (17)의 환시스템은 임의적으로 5-내지 7-원포화 카보싸이클 환으로 탄소-탄소결합에 의해 융합될 수 있다.
- R27은 질소-결합된 것이며 C1-6알킬, C1-6알킬 C2-6알케닐, C2-6알케닐, C2-8알콕시알킬, 카복시 C1-6알킬, [C1-6알콕시] 카보닐 C1-6알킬, 카바모일 C1-6알킬, 카복시아미노-카보닐 C1-6알킬, [C1-6알콕시] 카보닐아미노-카보닐 C1-6알킬, [(C2-8알카노일] 메틸, 벤조일메틸, C1-6하이드록시알킬, C1-6알킬아미노 또는 페닐 C1-6알킬이나 페닐이며, 각각은 임의적으로 할로겐, 하이드록시, 아미노, 카복시, 니트로, 카바모일, 시아노, 트리플루오로메틸 및 아미노메틸로부터 선택된 1 또는 2개그룹에 의해 치환될 수 있다 ; R26은 수소, C1-6알킬, 페닐 또는 벤질 ; R28은 시아노 C3-6싸이클로알케닐, 또는 할로겐, 니트로, 아미노, C1-4알카노일, C1-4알카노일아미노, 하로C1-4알킬, 하이드록시, 카복시, C2-6알콕시카보닐, 카바모일, 모노-또는 디 C1-4알킬카바모일, 시아노, 메실, 비닐, 및 설포로부터 선택된 1 또는 그룹으로 치환된 페닐이다 ; 또는 R28은 C2-6알케닐(임의적으로 할로겐, 시아노, 카바모일, 모노-또는 디(C1-4알킬)카바모일, 피페리디노카보닐, 또는 모르폴리노카보닐, 시아노 C1-4알킬, 2-우레이도에닐, 2-(티오우레이도에틸, 2-(티오아세틸아미노)에틸, 설파모일, 2-아미노-2-카복시에틸, 아세틸아미노메틸, 프탈이미도메틸, 4,5-디하이드로이미다졸-2-일메틸, 3,4,5,6-테트라하이드로-피리미딘-2-일메틸, 2-(1,2,3,6-테트라하이드로-2,6 디옥소퓨린-7-일)에틸, 2-하이드록시 이미노프로필(함께 또는 대응하여)또는 2-[(C1-4알콕시이미노] 프로필(함께 또는 대응하여)에 의해 치환된 또는 R28은 일반식 -(CH2)2- 29R30R31(R29, R36및 R31은 C1-4알킬)이거나 R28은 일반식 -(CH2)q-R32(q는 0-2이고 R32는 피리딘, 피리다진, 피리미딘, 피라진, 1,2,5,6-디하이드로-5,6-디옥소-1,2,4-트리아진, 2-[C1-4알킬]-1,2,5,6-디하이드로-5,6-디옥소-1,2,4-트리아진, 1-[C1-4알킬] 테트라졸, 푸란, 티오펜, 피롤, 1-[C1-4알킬] 피롤, 옥사졸, 티아졸, 이미다졸, 1-[C1-4알킬] 이미다졸, 이소옥사졸, 이소티아졸, 피라졸, 2,3-티아디아졸, 1-[C1-4알킬] 피라졸, 벤즈푸란, 벤즈티오펜, 인돌, 옥스인돌, 1-[C1-4알킬] 인돌, 벤족사졸, 벤즈티아졸, 1-[C1-4알킬] 벤즈이미다졸, 3,4-디하이드로-4-옥소-2H 벤조 [e] 옥사진이며 각각의 이러한 환시스템은 탄소를 통해 (CH2)q와 연결되며 각 환은 할로겐, 아미노, C1-6알킬, C1-4할로알킬, C3-6싸이클로알킬, C2-6알케닐, 카복시, C2-6알콕시카보닐, C1-6알콕시, 시아노, C2-6시아노알케닐, 카바모일, 모노-또는 디 C1-4알킬카바모일, C1-4알카노일아미노, 구아니디노, 하이드록시, 니트로, 아미노이며 이러한 환 시스템이 질소를 함유할 경우 이의 N-옥사이드가 가능하다); 또는 R4가 수소일 경우, R5는 일반식(51)이다.
- (여기서 R28은 임의적으로 할로겐, C1-6알킬, 하이드록시, C1-4알콕시, 카복시, C2-6알콕시카보닐, 니트로 또는 카바모일로 치환되는 2-구아니디노-티아졸-4-일메틸, 하이드록시벤조일-메틸, 2-테닐, 2-이미다졸릴메틸 또는 신나밀이다) R4가 수소가 아닌 다른것일 경우, R6는 또한 일반식(52)이다.
-
- J는 피리딘, 피리미딘, 옥사졸, 티아졸, 이소옥사졸, 이소티아졸 또는 이미다졸이며, 각각은 가능한 경우, 임의 적으로 벤젠, 싸이클로펜탄 또는 싸이클로헥산 환과 융합될 수 있다; R3은 수소, 아미노, C1-6알킬, -C3-6싸이클로알킬, C3-6알케닐, C2-8알콕시알킬, -(CH2)t-COOR35, -(CH2)t-CONH2, -(CH2)t-NHCO-R36또는 -(CH2)tS(O)S-R36이며, t는 1-6이고, R35는 수소 또는 C1-6알킬이며, s는 0,1 또는 2이고, R36은 C1-6알킬 또는 C1-6알콕시이거나, R33은 C3-8알카노일메틸,겐조일메틸, C1-6프라이머리하이드록시알킬, C1-6프라이머리아미노알킬,C1-4알킬아미노 C1-6알킬, 디 C1-4알킬아미노 C1-6알킬,카바모일 C1-4알킬, 모노-또는 디 C1-4알킬카바모일 C1-4알킬, C1-4알콕시 C1-4알킬, C1-6알콕시, C1-4알콕시 C2-4알콕시 C1-4알킬, C1-6알킬아미노, 페닐 C1-6알킬 또는 페닐 C1-6알콕시 또는 일반식 (CH2)2N=CR37NR38R39또는 (CH2)nC(NR37)N R38R39또는 그의 토오토머이다.
- (R37, R38및 R39는 수소 또는 C1-4알킬); R34는 수소이거나 또는 할로겐, 아미노, 니트로, C1-6알킬, 카복시, C2-6알콕시카보닐, C1-6알콕시, 시아노, 카바모일, C1-6할로알킬, C1-6아지도알킬, C1-6아미노알킬, C2-4아미노알킬티오 C1-4알킬, C2-6알카노일아미노, C2-4알카노일아미노 C1-4알킬, C2-6알카노일옥시 C1-4알킬, 벤질, 벤질옥시 및]헤테로아릴티오로부터 선택한 한 개 또는 두 개의 치환체이다. R33이 페닐을 함유하는 경우, 페닐은 임의적으로 할로겐, 니트로, C1-6알킬, 하이드록시, C1-4알콕시, 카복시, C2-6알콕시카보닐, 카바모일, 설파모일, 설포, 모노-또는 디 C1-4알킬카바모일, 또는 모노-또는 디 C1-4알킬설파모일이며, R34가 테트로아릴티오인 경우 테트로알리환은 산소, 질소 및 황으로부터 선택한 1,2 또는 3 헤테로원자를 함유하는 5-또는 6-원환이다. R40은 대체 가능한 기, 예컨대 불소, 염소, 브롬, C1-6알콕시, C1-6알킬티오, C1-6알칸설피닐 또는 C1-6알칸설포닐이다.
- ※참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB84401116.3 | 1984-05-30 | ||
EP84401116 | 1984-05-30 | ||
EP84401116.3 | 1984-05-30 | ||
GB8513106 | 1985-05-23 | ||
GB858513106A GB8513106D0 (en) | 1984-05-30 | 1985-05-23 | Cephalosporin derivatives |
Publications (2)
Publication Number | Publication Date |
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KR850008489A true KR850008489A (ko) | 1985-12-18 |
KR930000032B1 KR930000032B1 (ko) | 1993-01-06 |
Family
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Application Number | Title | Priority Date | Filing Date |
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KR1019850003778A KR930000032B1 (ko) | 1984-05-30 | 1985-05-30 | 세팔로스포린 유도체의 제법 |
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Country | Link |
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US (1) | US5049558A (ko) |
EP (1) | EP0164944B1 (ko) |
JP (1) | JPH0764853B2 (ko) |
KR (1) | KR930000032B1 (ko) |
AT (1) | ATE54453T1 (ko) |
AU (1) | AU584898B2 (ko) |
DE (1) | DE3578605D1 (ko) |
DK (1) | DK234885A (ko) |
ES (5) | ES8700670A1 (ko) |
FI (1) | FI851934L (ko) |
GB (1) | GB8513106D0 (ko) |
GR (1) | GR851235B (ko) |
HU (1) | HU202542B (ko) |
IE (1) | IE58494B1 (ko) |
IL (1) | IL75273A (ko) |
NO (1) | NO852134L (ko) |
NZ (1) | NZ212231A (ko) |
PT (1) | PT80553B (ko) |
ZA (1) | ZA853794B (ko) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
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GB8413152D0 (en) * | 1983-06-03 | 1984-06-27 | Ici Pharma | Cephalosporin derivatives |
US5254679A (en) * | 1984-05-30 | 1993-10-19 | Imperial Chemical Industries Plc | Cephalosporin intermediates |
EP0182633A3 (en) * | 1984-11-20 | 1987-09-02 | Ici Pharma | Cephalosporin derivatives |
DE3541095A1 (de) * | 1985-11-21 | 1987-05-27 | Bayer Ag | Neue cephalosporine, verfahren zu deren herstellung sowie ihre verwendung als arzneimittel |
GB8626245D0 (en) * | 1985-11-27 | 1986-12-03 | Ici Pharma | Cephalosporin compounds |
US5225406A (en) * | 1986-04-14 | 1993-07-06 | Banyu Pharmaceutical Co., Ltd. | 1-carboxy-1-vinyloxyimino aminothiazole cephalosporin derivatives |
GB8611823D0 (en) * | 1986-05-15 | 1986-06-25 | Ici Plc | Process |
GB8816519D0 (en) * | 1987-07-23 | 1988-08-17 | Ici Plc | Antibiotic compounds |
PH25965A (en) * | 1988-06-06 | 1992-01-13 | Fujisawa Pharmaceutical Co | New cephem compounds which have antimicrobial activities |
US5281589A (en) * | 1991-06-15 | 1994-01-25 | Cheil Foods & Chemicals, Inc. | 3-fused pyridiniummethyl cephalosporins |
KR100194994B1 (ko) * | 1993-06-05 | 1999-06-15 | 손경식 | 새로운 세펨 화합물 |
RU2201933C2 (ru) * | 1997-04-01 | 2003-04-10 | Биохеми Гезельшафт Мбх | Антибактериальные замещенные 7-ациламино-3-(метилгидразоно)метилцефалоспорины, способ их получения, фармацевтические композиции на их основе, промежуточные соединения и способ лечения заболеваний, вызванных микроорганизмами |
AT406772B (de) | 1998-03-23 | 2000-08-25 | Biochemie Gmbh | Antibakterielle 7-acylamino-3-iminomethyl- cephalosporine und verfahren zu deren herstellung |
CA2366260A1 (en) * | 1999-03-05 | 2000-09-14 | Masahiro Imoto | Heterocyclic compounds having effect of activating .alpha.4.beta.2 nicotinic acetylcholine receptors |
JP5403205B2 (ja) * | 2007-10-29 | 2014-01-29 | 日産化学工業株式会社 | 2−アミノ−n−(2,2,2−トリフルオロエチル)アセトアミド化合物又はその塩の製造方法 |
JP6027611B2 (ja) | 2011-07-19 | 2016-11-16 | インフィニティー ファーマシューティカルズ, インコーポレイテッド | 複素環式化合物及びその使用 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
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FR1584713A (ko) * | 1967-01-18 | 1970-01-02 | ||
GB1399086A (en) * | 1971-05-14 | 1975-06-25 | Glaxo Lab Ltd | Cephalosporin compounds |
DE2714880A1 (de) * | 1977-04-02 | 1978-10-26 | Hoechst Ag | Cephemderivate und verfahren zu ihrer herstellung |
ZA792581B (en) * | 1978-05-26 | 1981-01-28 | Glaxo Group Ltd | Cephalosporin antibiotics |
GB1604724A (en) * | 1978-05-26 | 1981-12-16 | Glaxo Operations Ltd | 7-(2-aminothiazol-4-yl)-2-oxymino-acedamido)-cephem derivatives |
AR231986A1 (es) * | 1978-05-26 | 1985-04-30 | Glaxo Group Ltd | Procedimiento para preparar antibioticos de cefalosporina |
GB2036738B (en) * | 1978-11-17 | 1983-01-19 | Glaxo Group Ltd | Cephalosporin antibiotics |
GB2046261B (en) * | 1979-03-22 | 1983-07-20 | Glaxo Group Ltd | Cephalosporin antibiotics |
EP0018595B1 (en) * | 1979-04-27 | 1986-08-20 | Merck & Co. Inc. | 7-n-heterocyclyl cephalosporins, a process for preparing and a pharmaceutical composition comprising the same |
NZ198350A (en) * | 1980-09-25 | 1985-02-28 | Toyama Chemical Co Ltd | Cephalosporins and intermediates;pharmaceutical compositions |
GB2103205A (en) * | 1981-06-15 | 1983-02-16 | Fujisawa Pharmaceutical Co | New cephem compounds |
FR2516515A1 (fr) * | 1981-11-16 | 1983-05-20 | Sanofi Sa | Nouveaux derives de pyridinium thiomethyl cephalosporines, procede pour leur preparation et compositions pharmaceutiques les contenant |
US4500526A (en) * | 1982-06-28 | 1985-02-19 | Bristol-Myers Company | Cephalosporin derivatives |
GB8413152D0 (en) * | 1983-06-03 | 1984-06-27 | Ici Pharma | Cephalosporin derivatives |
DE3419012A1 (de) * | 1984-05-22 | 1985-11-28 | Bayer Ag, 5090 Leverkusen | Ss-lactamantibiotika, verfahren zu deren herstellung sowie ihre verwendung als arzneimittel oder wachstumsfoerderer in der tieraufzucht oder als antioxidantien |
-
1985
- 1985-05-15 FI FI851934A patent/FI851934L/fi not_active Application Discontinuation
- 1985-05-16 AU AU42545/85A patent/AU584898B2/en not_active Ceased
- 1985-05-17 IE IE124185A patent/IE58494B1/en not_active IP Right Cessation
- 1985-05-20 ZA ZA853794A patent/ZA853794B/xx unknown
- 1985-05-21 GR GR851235A patent/GR851235B/el unknown
- 1985-05-22 IL IL75273A patent/IL75273A/xx unknown
- 1985-05-23 AT AT85303662T patent/ATE54453T1/de not_active IP Right Cessation
- 1985-05-23 EP EP85303662A patent/EP0164944B1/en not_active Expired - Lifetime
- 1985-05-23 GB GB858513106A patent/GB8513106D0/en active Pending
- 1985-05-23 DE DE8585303662T patent/DE3578605D1/de not_active Expired - Fee Related
- 1985-05-24 DK DK234885A patent/DK234885A/da not_active Application Discontinuation
- 1985-05-27 HU HU851999A patent/HU202542B/hu not_active IP Right Cessation
- 1985-05-29 NZ NZ212231A patent/NZ212231A/xx unknown
- 1985-05-29 NO NO852134A patent/NO852134L/no unknown
- 1985-05-30 PT PT80553A patent/PT80553B/pt not_active IP Right Cessation
- 1985-05-30 JP JP60115546A patent/JPH0764853B2/ja not_active Expired - Lifetime
- 1985-05-30 KR KR1019850003778A patent/KR930000032B1/ko not_active IP Right Cessation
- 1985-05-30 ES ES543689A patent/ES8700670A1/es not_active Expired
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1986
- 1986-02-14 ES ES551990A patent/ES8706701A1/es not_active Expired
- 1986-02-14 ES ES551987A patent/ES8706698A1/es not_active Expired
- 1986-02-14 ES ES551989A patent/ES8706700A1/es not_active Expired
- 1986-02-14 ES ES551988A patent/ES8706699A1/es not_active Expired
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1989
- 1989-09-19 US US07/409,290 patent/US5049558A/en not_active Expired - Fee Related
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