Novel antibacterial agents 机翻标题: 暂无翻译,请尝试点击翻译按钮。

公开号/公开日
EP1005356 A1 2000-06-07 [EP1005356]EP1005356 A4 2001-08-22 [EP1005356]EP1005356 B1 2006-04-12 [EP1005356] / 2000-06-072001-08-222006-04-12
申请号/申请日
1999EP-0928455 / 1999-06-07
发明人
GRIFFIN JOHN H;MORAN EDMUND J;CHRISTENSEN BURTON G;JUDICE J KEVIN;MU YONGQI;PACE JOHN;
申请人
THERAVANCE;
主分类号
IPC分类号
A01N-057/34A61K-031/00A61K-031/357A61K-031/397A61K-031/407A61K-031/421A61K-031/424A61K-031/431A61K-031/439A61K-031/444A61K-031/4545A61K-031/496A61K-031/522A61K-031/536A61K-031/5377A61K-031/546A61K-031/551A61K-031/65A61K-031/7028A61K-031/7034A61K-031/7036A61K-031/7042A61K-031/7048A61K-031/7052A61K-031/7056A61K-031/7064A61K-031/7068A61K-031/7072A61K-038/00A61K-038/14A61K-039/00A61K-039/395A61K-039/44A61K-047/48A61K-051/00A61P-031/04A61P-031/18A61P-043/00C07B-061/00C07C-233/36C07C-233/78C07C-237/24C07C-237/26C07C-271/20C07C-275/42C07C-321/04C07C-323/12C07C-335/08C07C-335/32C07D-207/32C07D-207/333C07D-211/58C07D-215/56C07D-233/90C07D-235/30C07D-263/28C07D-265/18C07D-401/06C07D-401/12C07D-401/14C07D-405/04C07D-413/14C07D-453/02C07D-471/04C07D-471/14C07D-473/00C07D-473/34C07D-475/04C07D-475/08C07D-477/00C07D-487/04C07D-487/06C07D-493/04C07D-493/06C07D-495/04C07D-498/04C07D-498/18C07D-499/00C07D-499/44C07D-501/00C07D-501/20C07D-519/00C07H-015/236C07H-015/238C07H-015/26C07H-017/08C07H-019/06C07H-019/20C07K-002/00C07K-004/00C07K-009/00C12N-009/99C12P-019/38C12Q-001/26C12Q-001/44C12Q-001/48C12Q-001/533C40B-030/04C40B-040/04G01N-033/15G01N-033/50G01N-033/53G01N-033/543G01N-033/566G01N-033/573G01N-033/68G01N-033/92G01N-037/00
摘要
(EP1005356) This invention relates to novel multibinding compounds (agents) that are antibacterial agents.  The multibinding compounds of the invention comprise from 2-10 ligands covalently connected by a linker or linkers, wherein each of said ligands in their monovalent (i.e., unlinked) state have the ability to bind to an enzyme involved in cell wall biosynthesis and metabolism.  A precursor used in the synthesis of the bacterial cell wall and/or the bacterial cell surface thereby interfere with the synthesis and/or metabolism of the cell wall.  In particular the multibinding compounds of the invention comprise from 2-10 ligands covalently connected by a linker or linkers, wherein each of said ligands has a ligand domain capable of binding to penicillin binding proteins, a transpeptidase enzyme, a substrate of a transpeptidase enzyme, a beta-lactamase enzyme, penicillinase enzyme, cephalosporinase enzyme, a transglycosylase enzyme, or a transglycosylase enzyme substrate.  Preferably, the ligands are selected from the beta-lactam or glycopeptide class of antibacterial agents.
机翻摘要
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地址
代理人
代理机构
;
优先权号
1998US-60088448 1998-06-08 1998US-60093072 1998-07-16 1999WO-US12776 1999-06-07
主权利要求
(EP1005356)  1. A compound of Formula (I):            (L) p(X) q     (I)    or a pharmaceutically acceptable salt thereof, wherein: p is 2;  q is 1;  one ligand, L, is a beta lactam antibiotic, and the other ligand, L, is an optionally substituted glycopeptide antibiotic, or an aglycone derivative of an optionally substituted glycopeptide antibiotic;  and X is a linker;  provided that when one of the ligands is vancomycin attached via the carboxy terminus, then the other ligand cannot be cefalexin attached to the linker via acylation of its alpha amino group. 2. The compound of Claim 1 wherein: the ligand that is a beta lactam antibiotic is selected from penems, penams, cephems, carbapenems, oxacephems, carbacephems, and monobactam ring systems;  and the ligand that is a glycopeptide antibiotic is selected from Chloroeremomycin, Chloroorienticin, Vancomycin and aglycone derivatives thereof. 3. The compound of Claim 2 wherein the ligand that is a beta lactam antibiotic is selected from: (i) a ligand of formula (a): (see diagramm) wherein: R is substituted alkyl, aryl, aralkyl, or heteroaryl wherein each of said substituent optionally links (a) to the linker via a covalent bond or R is a covalent bond that links (a) to the linker;  and R **1 and R **2 are, independently of each other, alkyl or one of R **1 and R **2 is a covalent bond linking (a) to the linker;(ii) a ligand of formula (b): (see diagramm) wherein: one of P and Q is O, S, or -CH 2- and the other is -CH 2-;  R **3 is substituted alkyl, heteroarylalkyl, aralkyl, heterocyclylalkyl, or -C(R **6)=NOR **7 (where R **6 is aryl, heteroaryl, or substituted alkyl;  and R **7 is alkyl or substituted alkyl) wherein each of said substituents optionally links (b) to a linker or R **3 is a covalent bond that links (b) to the linker;  and R **4 is hydrogen, alkyl, alkenyl, substituted alkenyl, substituted alkyl, halo, heteroarylalkyl, heterocyclylalkyl, -SR **a (where R **a is aryl, heteroaryl, heterocyclyl, or cycloalkyl) or -CH 2SR **a (where R **a is aryl, heteroaryl, heterocyclyl, or cycloalkyl) wherein each of said substituents optionally links (b) to a linker or R **4 is a covalent bond that links (b) to the linker;  R **5 is hydrogen, hydroxy, or alkoxy;(iii) a ligand of formula (c): (see diagramm) wherein: T is S or CH 2;  R **8a is alkyl;  W is O, S, -OCH 2-, or CH 2;  and R **8 is -(alkylene)-NHC(R **b)=NH where R **b is a covalent bond linking (c) to a linker;  or -W-R **8 is a covalent bond that links (c) to the linker;(iv) a ligand of formula (d): (see diagramm) wherein: R **9 and R **9a are alkyl;  R' deg. is selected from the group consisting of hydrogen, alkyl, substituted alkyl, halo, aryl, heteroaryl, heterocyclyl, aralkyl, heteroaralkyl, heterocyclylalkyl or -CH 2SR **a (where R **a is aryl, heteroaryl, heterocyclyl, or cycloalkyl) wherein each of said substituents optionally links (d) to the linker or one of R **9 and R **10 is a covalent bond that links (d) to the linker;  or R **9 and R **10 together with the carbon atoms to which they are attached form an aryl, heteroaryl, cycloalkyl, substituted cycloalkyl, or heterocyclyl ring of 4 to 7 ring atoms wherein one of the ring atoms optionally links (d) to the linker;  or(v) a ligand of formula (e): (see diagramm) wherein: R **11 is -SO 3H or -(alkylene)-COOH;  R **12 is alkyl, substituted alkyl, haloalkyl, alkoxy, aryl, aralkyl, heteroaryl, heteroaralkyl, cycloalkyl, substituted cycloalkyl, or heterocyclyl wherein each of said substituents optionally binds (e) to the linker or R **12 is a covalent bond that links (e) to the linker;  and R **13 is alkyl, acyl, or -COC(R **14)=N-OR **15 wherein R **14 is aryl, heteroaryl which optionally links (e) to the linker, and R **15 is -(alkylene)-COOR **16 wherein R **16 is hydrogen or a covalent bond which optionally links (e) to the linker or R **13 is a covalent bond that links (e) to the linker;  and the ligand that is a glycopeptide antibiotic is an optionally substituted vancomycin which is linked to the linker via any hydroxyl group, carboxyl group or amino group. 4. The compound of Claim 3 wherein the ligand that is a beta lactam antibiotic is selected from: (i) a ligand of formula (a): (see diagramm) wherein: R is: (see diagramm)(see diagramm)(see diagramm)(see diagramm) where: R **17 is a covalent bond that links the (a) group to the linker;  one of R **18 and R **19 is hydrogen and the other is a covalent bond that links the (a) group to the linker;  and R **1 and R **2 are methyl;(ii) a ligand of formula (b): (see diagramm) where: R **3 and R **4 are: (see diagramm) (see diagramm) wherein: R is alkyl;  R **16 is a covalent bond that links the (b) group to the linker;  one of R **18 and R **19 is hydrogen or alkyl and the other is a covalent bond that links the (b) group to the linker;(iii) a ligand of formula (c): (see diagramm) wherein R **b is a covalent bond linking (c) to the linker;  (iv) a ligand of formula (d): (see diagramm) where R **a is: (see diagramm)(see diagramm)(see diagramm) where: R **23 is a covalent bond that links (d) to the linker;  one of R **24 and R **25 is alkyl, substituted alkyl, or aralkyl, and other is a covalent bond that links (d) to the linker;  or(v) a ligand of formula (e): (see diagramm) wherein one of R **21 and R **22 is hydrogen and the other links (d) to the linker. 5. The multibinding compound of Claim 4 wherein the linker is selected from a compound of formula:            -X **a-Z-(Y **a-Z) m-X **a-    wherein m is an integer of from 0 to 20;  X **a at each separate occurrence is selected from -O-, -S-, -NR-, -C(O)-, -C(O)O-, -OC(O)-, -C(O)NR-, -NRC(O)-, C(S), -C(S)O-, -C(S)NR-, -NRC(S)-, or a covalent bond where R is as defined below;  Z at each separate occurrence is selected from alkylene, substituted alkylene, cycloalkylene, substituted cylcoalkylene, alkenylene, substituted alkenylene, alkynylene, substituted alkynylene, cycloalkenylene, substituted cycloalkenylene, arylene, heteroarylene, heterocyclene, or a covalent bond;  each Y **a at each separate occurrence is selected from -O-, -C(O)-, -OC(O)-, -C(O)O-, -NR-, -S(O)n-, -C(O)NR'-, -NR'C(O)-, -NR'C(O)NR'-, -NR'C(S)NR'-, -C(=NR')-NR'-, -NR'-C(=NR')-, -OC(O)-NR'-, -NR'-C(O)-O-, -P(O)(OR')-O-, -O-P(O)(OR')-, -S(O) nCR'R"-, -S(O) n-NR'-, -NR'-S(O) n-, -S-S-, and a covalent bond;  where n is 0, 1 or 2;  and R, R' and R" at each separate occurrence are selected from hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkenyl, substituted alkenyl, cycloalkenyl, substituted cycloalkenyl, alkynyl, substituted alkynyl, aryl, heteroaryl and heterocyclic. 6. A compound as claimed in claim 1, which is Vancomycin-Amoxicillin heterodimer of structure 19;  Vancomycin-Imipenem heterodimer of structure 30;  or Vancomycin-Imipenem heterodimer of structure 33: (see diagramm)(see diagramm)(see diagramm) 7.  A pharmaceutical composition comprising a pharmaceutically acceptable carrier and an effective amount of a compound of any of claims 1 to 6. 8. A compound as claimed in any one of claims 1 to 6, or a pharmaceutical composition as claimed in claim 7 for use as a medicament. 9. A compound as claimed in claim 8 for use as a medicament for treating a bacterial disease in a mammal. 10. Use of a compound as claimed in any one of claims 1 to 6, or a pharmaceutical composition as claimed in claim 7, for the manufacture of a medicament for treating a bacterial disease in a mammal.
法律状态
(EP1005356) LEGAL DETAILS FOR EP1005356  Actual or expected expiration date=2019-06-07    Legal state=ALIVE    Status=GRANTED     Event publication date=1999-06-07  Event code=EP/APP  Event indicator=Pos  Event type=Examination events  Application details  Application country=EP EP99928455  Application date=1999-06-07  Standardized application number=1999EP-0928455     Event publication date=2000-06-07  Event code=EP/A1  Event type=Examination events  Application published with search report  Publication country=EP  Publication number=EP1005356  Publication stage Code=A1  Publication date=2000-06-07  Standardized publication number=EP1005356     Event publication date=2000-06-07  Event code=EP/AK  Event indicator=Pos  Event type=Designated states  Designated contracting states: Benannte vertragsstaaten AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE    Event publication date=2000-07-12  Event code=EP/RAP1  Event type=Change of name or address  Event type=Reassignment  Transfer of rights of an application Anmelder uebertragung (korr.) Owner: ADVANCED MEDICINE, INC.    Event publication date=2000-08-16  Event code=EP/17P  Event indicator=Pos  Event type=Examination events  Request for examination filed Pruefungsantrag gestellt  Effective date of the event=2000-06-16     Event publication date=2000-09-06  Event code=EP/RIC1  Event type=Classification modifications  Event type=Corrections  Classification (correction) 7A 61K  38/00   A, 7A 61K  39/00   B, 7A 61K  39/44   B, 7A 61K  39/395  B, 7A 61K  51/00   B, 7C 07K   2/00   B, 7C 07K   4/00   B, 7G 01N  33/53   B, 7G 01N  33/543  B, 7G 01N  33/566  B, 7C 07B  61/00   B     Event publication date=2000-10-25  Event code=EP/RIN1  Event type=Change of name or address  Event type=Administrative notifications  Inventor (correction) Inventor changed before grant Inventor: GRIFFIN, JOHN, H.    Event publication date=2000-10-25  Event code=EP/RIN1  Event type=Change of name or address  Event type=Administrative notifications  Inventor (correction) Inventor changed before grant Inventor: MORAN, EDMUND, J.    Event publication date=2000-10-25  Event code=EP/RIN1  Event type=Change of name or address  Event type=Administrative notifications  Inventor (correction) Inventor changed before grant Inventor: CHRISTENSEN, BURTON, G.    Event publication date=2001-08-08  Event code=EP/RIC1  Event type=Classification modifications  Event type=Corrections  Classification (correction) 7A 61K  38/00   A, 7A 61K  39/00   B, 7A 61K  39/44   B, 7A 61K  39/395  B, 7A 61K  51/00   B, 7C 07K   2/00   B, 7C 07K   4/00   B, 7G 01N  33/53   B, 7G 01N  33/543  B, 7G 01N  33/566  B, 7C 07B  61/00   B, 7C 07D 501/00   B, 7C 07D 499/00   B, 7C 07K   9/00   B     Event publication date=2001-08-22  Event code=EP/A4  Event indicator=Pos  Event type=Examination events  Supplementary search report Ergaenzender recherchenbericht  Publication country=EP  Publication number=EP1005356  Publication stage Code=A4  Publication date=2001-08-22  Standardized publication number=EP1005356     Event publication date=2001-08-22  Event code=EP/A4  Event indicator=Pos  Event type=Administrative notifications  Supplementary search report Despatch of supplementary search report  Effective date of the event=2001-07-10     Event publication date=2001-08-22  Event code=EP/AK  Event indicator=Pos  Event type=Designated states  Designated contracting states: Benannte vertragsstaaten AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE    Event publication date=2002-04-24  Event code=EP/RIN1  Event type=Change of name or address  Event type=Administrative notifications  Inventor (correction) Inventor changed before grant Inventor: GRIFFIN, JOHN, H.    Event publication date=2002-04-24  Event code=EP/RIN1  Event type=Change of name or address  Event type=Administrative notifications  Inventor (correction) Inventor changed before grant Inventor: MORAN, EDMUND, J.    Event publication date=2002-04-24  Event code=EP/RIN1  Event type=Change of name or address  Event type=Administrative notifications  Inventor (correction) Inventor changed before grant Inventor: CHRISTENSEN, BURTON, G.    Event publication date=2002-04-24  Event code=EP/RIN1  Event type=Change of name or address  Event type=Administrative notifications  Inventor (correction) Inventor changed before grant Inventor: JUDICE, J. KEVIN    Event publication date=2002-04-24  Event code=EP/RIN1  Event type=Change of name or address  Event type=Administrative notifications  Inventor (correction) Inventor changed before grant Inventor: MU, YONGQI    Event publication date=2002-04-24  Event code=EP/RIN1  Event type=Change of name or address  Event type=Administrative notifications  Inventor (correction) Inventor changed before grant Inventor: PACE, JOHN    Event publication date=2002-07-24  Event code=EP/RAP1  Event type=Change of name or address  Event type=Reassignment  Transfer of rights of an application Anmelder uebertragung (korr.) Owner: THERAVANCE, INC.    Event publication date=2004-11-17  Event code=EP/17Q  Event indicator=Pos  Event type=Examination events  First examination report Erster pruefungsbescheid  Effective date of the event=2004-10-04     Event publication date=2005-06-29  Event code=EP/RIC1  Event type=Classification modifications  Event type=Corrections  Classification (correction) IPC: 7A 61K  39/44   A    Event publication date=2005-06-29  Event code=EP/RIC1  Event type=Classification modifications  Event type=Corrections  Classification (correction) IPC: 7A 61K  39/395  B    Event publication date=2005-06-29  Event code=EP/RIC1  Event type=Classification modifications  Event type=Corrections  Classification (correction) IPC: 7A 61K  51/00   B    Event publication date=2005-06-29  Event code=EP/RIC1  Event type=Classification modifications  Event type=Corrections  Classification (correction) IPC: 7C 07K   2/00   B    Event publication date=2005-06-29  Event code=EP/RIC1  Event type=Classification modifications  Event type=Corrections  Classification (correction) IPC: 7C 07K   4/00   B    Event publication date=2005-06-29  Event code=EP/RIC1  Event type=Classification modifications  Event type=Corrections  Classification (correction) IPC: 7C 07B  61/00   B    Event publication date=2005-06-29  Event code=EP/RIC1  Event type=Classification modifications  Event type=Corrections  Classification (correction) IPC: 7C 07D 501/00   B    Event publication date=2005-06-29  Event code=EP/RIC1  Event type=Classification modifications  Event type=Corrections  Classification (correction) IPC: 7C 07D 499/00   B    Event publication date=2005-06-29  Event code=EP/RIC1  Event type=Classification modifications  Event type=Corrections  Classification (correction) IPC: 7C 07K   9/00   B    Event publication date=2005-06-29  Event code=EP/RIC1  Event type=Classification modifications  Event type=Corrections  Classification (correction) IPC: 7A 61P  31/04   B    Event publication date=2005-06-29  Event code=EP/RIC1  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publication date=2005-08-03  Event code=EP/RIC1  Event type=Classification modifications  Event type=Corrections  Classification (correction) IPC: 7C 07B  61/00   B    Event publication date=2005-08-03  Event code=EP/RIC1  Event type=Classification modifications  Event type=Corrections  Classification (correction) IPC: 7C 07D 501/00   B    Event publication date=2005-08-03  Event code=EP/RIC1  Event type=Classification modifications  Event type=Corrections  Classification (correction) IPC: 7C 07D 499/00   B    Event publication date=2005-08-03  Event code=EP/RIC1  Event type=Classification modifications  Event type=Corrections  Classification (correction) IPC: 7C 07K   9/00   B    Event publication date=2005-08-03  Event code=EP/RIC1  Event type=Classification modifications  Event type=Corrections  Classification (correction) IPC: 7A 61P  31/04   B    Event publication date=2005-08-03  Event code=EP/RIC1  Event type=Classification modifications  Event type=Corrections  Classification (correction) IPC: 7A 61K  38/14   B    Event publication date=2006-04-12  Event code=EP/B1  Event indicator=Pos  Event type=Event indicating In Force  Patent specification  Publication country=EP  Publication number=EP1005356  Publication stage Code=B1  Publication date=2006-04-12  Standardized publication number=EP1005356     Event publication date=2006-04-12  Event code=EP/AK  Event indicator=Pos  Event type=Designated states  Designated contracting states: Benannte vertragsstaaten AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE    Event publication date=2006-04-12  Event code=EP/DAX  Event indicator=Neg  Event type=Designated states  Request for extension of the european patent (to any country) deleted    Event publication date=2007-05-02  Event code=EP/26N  Event indicator=Pos  Event type=No opposition filed  Event type=Event indicating In Force  No opposition filed Kein einspruch eingelegt  Effective date of the event=2007-01-15  MEMBER STATE LEGAL DETAILS FOR AT322910  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THERAVANCE, INC.#901 GATEWAY BOULEVARD#SOUTH SAN FRANCISCO, CA 94080 (US) -TRANSFER TO- THERAVANCE, INC.#901 GATEWAY BOULEVARD#SOUTH SAN FRANCISCO, CA 94080 (US)     Event publication date=2014-07-15  Event code=EP/REG  Event code=CH/PCAR  Event type=Change of name or address  Reference to a national code Change of the address of the representative Adressaenderung vertreter Corresponding cc:  Designated or member state=CH  NEW ADDRESS: HOLBEINSTRASSE 36-38, 4051 BASEL (CH)     Event publication date=2015-08-28  Event code=EP/REG  Event code=CH/PUE  Event type=Change of name or address  Event type=Reassignment  Reference to a national code Assignment Uebertragung Corresponding cc:  Designated or member state=CH  Owner: THERAVANCE BIOPHARMA ANTIBIOTICS IP, LLC, US FORMER OWNER: THERAVANCE, INC., US     Event publication date=2017-06-27  Event code=EP/PGFP  Event indicator=Pos  Event type=Event indicating In Force  Event type=Payment or non-payment notifications  Postgrant: annual fees 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