公开号/公开日

WO2013173905 A1 2013-11-28 [WO2013173905] / 2013-11-28

申请号/申请日

2013WO-CA00491 / 2013-05-16

发明人

LIU SONG;

申请人

UNIVERSITY OF MANITOBA;

主分类号

IPC分类号

A01N-043/50A01N-043/647A01P-001/00C07D-233/72C07D-233/82C07D-403/12

摘要

(WO2013173905) Biocidally active cationic analogs of N-halamine having two biocidally active groups covalently bonded together in a single molecule and having general Formula (I).  Compounds of Formula (I), and precursurs thereof, can be in solution form immobilized onto a substrate via physical coating or covalent chemical bonding to functionalize surfaces or added into materials as additives so as to render them biocidal.  The biocidal solutions and substrates comprising the compounds or precursors of the present invention can then be used to inactivate pathogenic microorganisms.  N-halamine-L-QUAT (I) wherein: the N-halamine may be a cyclic or acyclic N-halamine; L is C1-C6 alkyl, cyclic aromatic or non-aromatic ring, ether, ketone or any other organic linking structures, and QUAT has general formula ( II):

机翻摘要

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地址

代理人

代理机构

;

优先权号

2012US-61648167 2012-05-17 2013US-61772440 2013-03-04

主权利要求

(WO2013173905) THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS: 1. A biocidal compound having general formula (I): N-halamine-L-QUAT (I) wherein: the N-halamine may be a cyclic or acyclic N-halamine; L is CrC6alkyl, cyclic aromatic or non-aromatic ring,  ketone or any other organic linking structures, and QUAT has general formula (II):  wherein: 1 2 R and R are each independently Ci-C6alkyl;  L2 is absent, Ci-C6alkyl or A is R3, N-halamine or -N+R4R5R6; R3is C,-C18alkyl; R4and R5are each independently C C6alkyl; R6is d-C18alkyl or -(CH2)PB; B is N-halamine; n and m are each independently 1 -6, and p is 1-6, and wherein when A is R3, L2 is absent, and when A is N-halamine or -N+R4R5R6, L2 is C , -C6alkyl or  2. The compound according to claim 1, wherein the N-halamine is a cyclic N- halamine. 3. The compound according to claim 1 , wherein each N-halamine is independently a cyclic N-halamine having general formula (III) or general formula (IV):  wherein: Y is CH or N; Z is absent, CH2or NR23; R7is halo; R8and R9are each independently H, Ci-C4alkyl, or Cj-C4alkoxy, or R8and R9taken together form =0; R10and R11are each independently H, Ci-C4alkyl, or Ci-C4alkoxy, or R10and R11taken together form =0; and 12 13 12 R1and R" are each independently H, Ci-C4alkyl, or C1-C4alkoxy, or R and R13taken together form =0, and R23is H or halo, 8 9 1 13 wherein when Z is absent and R and R taken together form =0, R and R are each independently H, Q-C4alkyl, or CrC4alkoxy;  wherein: D is CH or N; R14is halo; R15and R16are each independently H, Ci-C4alkyl, or C1-C4alkoxy, or R15and R taken together form =0; R17and R18are each independently H, C1-C4alkyl, or C1-C4alkoxy, or R17and Q R taken together form =0; R19and R20are each independently H, C1-C4alkyl, or CpC4alkoxy, or R19and R taken together form =0, and R 211and R 22 are each independently H, Ci-C4alkyl, or CpC4alkoxy, or R 21 and 22 R taken together form =0, wherein when R and R taken together form =0, R and R are each independently H, C1-C4alkyl, or C1-C4alkoxy, and 21 22 19 20 wherein when R and R taken together form =0, R and R are each independently H, CrC4alkyl, or Cj-C4alkoxy. 4. The compound according to claim 3, wherein each N-halamine is a cyclic N- halamine having general formula (IV). 5. The compound according to claim 3, wherein each N-halamine is a cyclic N- halamine having general formula (III). 6. The compound according to claim 5, wherein: Y is N, and Z is absent or NR23 . 7. The compound according to claim 5, wherein: R1and R2are each -CH3, Y is N, and Z is absent or NR23 . 8. The compound according to claim 5, wherein each cyclic N-halamine has general formula (V):  wherein: R24and R25are each independently H, C]-C4alkyl, or Q-C4alkoxy, or R24and R25taken together form =0; R26and R27are each independently H, C)-C4alkyl, or C1-C4alkoxy, or R26and R taken together form =0; R and R are each independently H, Q-C4 alkyl, or Q-C4 alkoxy, or R and R29taken together form =0, and R30is halo, and wherein: when R24and R25taken together form =0, R26and R27are each independently H, C1-C4 alkyl, or C C4alkoxy. 9. The compound according to claim 8, wherein L is Ci-C6alkyl. 10. A compound having general formula (VI): wherein: L3 is C C6alkyl, cyclic aromatic or non-aromatic ring,5ether, ketone or any other organic linking structures,; R31and R32are each indepe alkyl; L4 is absent, C C6alkyl or E is R , N-halamine of general formula (V) or -N+R4iR4¾4J; R40is C1-C18 alkyl; R41and R42are each independently Ci-Ce alkyl; R43is C1-C18 alkyl or -(CH2)PM; M is N-halamine of general formula (V); n and m are each independently 1-6, and p is 1 -6, R33and R34are each independently H, Q-C4 alkyl, or Q-C4 alkoxy, or R33and R34taken together form =0; RJJand R are each independently H, C1-C4alkyl, or C1-C4alkoxy, or R and R36taken together form =0; R37and R38are each independently H, -C4 alkyl, or C1-C4alkoxy, or R37and R38taken together form =0, and R39is halo, wherein when E is R40, L4 is absent, and when E -halamine of general formula (V) or -N+R41R42R43, L4 is Ci-C6alkyl or  and wherein when R33and R34taken together form =0, R35and R36are each independently H, Ci-C4alkyl, or Q-C4alkoxy. 1 1. The compound according to any one of claims 1 to 10, wherein in any one of general formulae (II), (III), (IV), (V) or (VI), each halogen when present is -CI , or -Br, or -I. 12. The compound according to any one of claims 1 to 10, wherein in any one of general formulae (II), (III), (IV), (V) or (VI), n and m are each independently 1 -4. 13. The compound according to claim 10, wherein: R33and R34are each independently H or C C4alkyl, or R33and R34taken together form =0; R35and R36are each independently H or CrC4alkyl, or R35and R36taken together form =0, and R37and R38are each independently H or C1-C4 alkyl, or R37and R38taken together form =0. 14. The compound according to claim 10, wherein: R31and R32and R41and R42when present, are each -CH3 . 15. The compound according to claim 10, wherein: R31and R32and R41and R42when present, are each -CH3; R33and R34are each independently H or -CH3, or R33and R34taken together form =0; R35and R36are each independently H or -CH3, or R35and R36taken together form =0, and and RJ0are each independently H or -CH3, or R and R taken together form =0. 16. The compound according to claim 10, wherein: R33and R34taken together form =0; R35and R36are each independently H or C C4alkyl, and R37and R38taken together form =0. 17. The compound according to claim 10, wherein: R33and R34are each independently H or CpQ alkyl; R35and R36taken together form =0, and R37and R38taken together form =0. 18. The compound according to claim 10, wherein: R33and R34are each independently H or C C4alkyl; R35and R36taken together form =0, and R37and R38are each independently H or Q-C4 alkyl. 19. The compound according to claim 10, wherein: R33and R34taken together form =0; R35and R36are each independently H or Cj-C4alkyl, and R37and R38are each independently H or Ci-C4alkyl. 20. The compound according to claim 10, wherein: R33and R34are each independently H or Q-C4 alkyl; R35and R36are each independently H or Q-C4 alkyl, and R37and R38taken together form =0. 21. The compound according to any one of claims 10 to 20, wherein: R31and R32are each -CH3 . 22. The compound according to any one of claims 10 to 21, wherein each halo is - CI or -Br. 23. A precursor of the biocidal compound according to any one of claims 1 to 22, wherein each halo substituent in each N-halamine moiety is replaced with a hydrogen substituent, and wherein halogenation of said substituent results in the biocidally activity compound. 24. The precursor according to claim 23, having general formula (VII):  wherein: L5 is CrC6alkyl; R44and R45are each independently Ci-C6alkyl; L6 is absent, d-C6alkyl or  G is R , a N-halamine precursor of general formula (V) in which each halo substituent is replaced with a hydrogen substituent, or -N+R53R54R55; R52is C1-C18 alkyl; R53and R54are each independently C\-C alkyl; R55is C1-C18 alkyl or -(CH2)PJ; J is a N-halamine precursor of general formula (V) which comprises a hydrogen substituent in place of each halo substituent; n and m are each 0-6, and p is 1-6, R46and R47are each independently H, Q-C4 alkyl, or C C4alkoxy, or R46and R47taken together form =0; R48and R49are each independently H, Q-Q alkyl, or C C4alkoxy, or R48and R49taken together form =0; R50and R51are each independently H, C C alkyl, or Q-C4 alkoxy, or R50and R51taken together form =0, and wherein when G is R , L6 is absent, and -halamine precursor or -N+R53R54R55, L6 is Ci-C alkyl or  and wherein when R46and R47taken together form =0, R48and R49are each independently H, C1-C4 alkyl, or C1-C4 alkoxy. 25. The compound according to claim 1 , or the precursor according to claim 23, wherein the compound or precursor is selected from compounds having general formula (VIII), (IX) or (X):  wherein: X is H, CI or Br; n is 1 or 2; R' is CrCi2 alkyl, and R" is CrC6alkyl;  wherein: X is H, CI or Br, and R' is C1-C12 alkyl;  wherein: X is H, CI or Br; R' is C1-C12 alkyl, and R" is CrC6alkyl. The compound according to any one of claims 1 to 22 and 25, or the precursor according to any one of claims 23 to 25, wherein the compound or precursor is derivatized to allow attachment of the compound or precursor to another compound, surface, substrate or polymer. 27. The compound or precursor according to claim 26, wherein the compound or precursor is derivatized to include an azide moiety or an alkynyl group to allow for attachment to another compound, surface, substrate or polymer through "click" chemistry. 28. The compound or precursor according to claim 27, wherein one or more of the alkyl groups attached to the quaternary ammonium centre in any of general formulae (II), (III), (IV), (V), (VI) or (VII), is derivatized to include a terminal azide or alkynyl moiety. 29. The compound according to claim 25, the precursor according to claim 25, or a derivative thereof, wherein the compound, precursor, or derivative is selected from compounds 1 to 42: 1 X = 2 X = C I, R' = CH36 X = CI, R' = C6H1 ; 3 X— H, R'— CjHg 7 X=H, R'=C-12H2: 9 X = H 4 X = CI, R' = C4H98 X = CI, R' = C12H 10 X = CI  11 X = H 13 X, X' = H 12 X = CI 14 X, X' = CI  X = H X = CI  17 X = H 18 X = CI  9 X = H 0 X = CI  21 X = H, R' = C2H525 X = H, R' = C8H17 22 X = CI, R' = C2H526 X = CI, R' = C8H17 23 X = H, R' = C4H9 24 X = CI, R' = C4H9 37 X = H, R' = C6H1338 X = CI, R' = C6Hi3X, Χ' = H X, X' = CI  9 R' = CH3 0 R' = C12H25  R' = CH336 R' = C6H13R' = C2H535 R'=CgH-|7 R' = C4H936 R'=C12H25  41 42 30. A composition comprising the compound of any one of claims 1 to 22, 25 to 28, and 29, the precursor of any one of claims 23 to 25, 28, and 29, or the derivative of claim 29. 31. The composition according to claim 30, wherein the composition is a solution. 32. The composition according to claim 30, wherein the composition comprises a substrate comprising one or more of said compounds, precursors, or derivatives attached to the surface of the substrate. 33. The composition according to claim 30, wherein the composition comprises a substrate comprising one or more of said compounds, precursors, or derivatives incorporated within the substrate. 34. The composition according to claim 32 or claim 33, wherein the substrate is a woven, knit, or nonwoven substrate; 35. The composition according to claim 34, wherein the substrate is a semicrystalline thermoplastic polymeric substrate. 36. The composition according to claim 35, wherein the substrate is PET. 37. The composition according to claim 34, wherein the substrate is cotton. 38. Use of the compound of any one of claims 1 to 22, 25 to 28, and 29, the precursor of any one of claims 23 to 25, 28, and 29, or the derivative of claim 29 as a disinfectant.

法律状态

(WO2013173905) LEGAL DETAILS FOR WO2013173905  Actual or expected expiration date=2015-11-17    Legal state=DEAD    Status=LAPSED     Event publication date=2013-05-16  Event code=WO/APP  Event indicator=Pos  Event type=Examination events  Application details  Application country=WO WOCA2013000491  Application date=2013-05-16  Standardized application number=2013WO-CA00491     Event publication date=2013-11-28  Event code=WO/A1  Event type=Examination events  Published application with search report  Publication country=WO  Publication number=WO2013173905  Publication stage Code=A1  Publication date=2013-11-28  Standardized publication number=WO2013173905     Event publication date=2014-05-15  Event code=WO/DPE1  Event type=Examination events  Request for preliminary examination filed after expiration of 19th month from priority date (pct application filed from 20040101)    Event publication date=2015-11-17  Event code=WO/EETL  Event type=Event indicating Not In Force  PCT Application validity period expired. LEGAL DETAILS FOR DESIGNATED STATE AU2013265971  Actual or expected expiration date=2018-04-19    Legal state=DEAD    Status=LAPSED   Corresponding cc:  Designated or member state=AU Corresponding appl: AU2013265971  Application date in the designated or member state=2013-05-16   Application number in the designated or member state=2013AU-0265971 Corresponding cc:  Designated or member state=AU Corresponding pat: AU2013265971  Publication stage code in the designated or member state=A1  Publication date in the designated or member state=2014-12-18   Publication number in the designated or member state=AU2013265971    Event publication date=2014-12-18  Event code=WO/ENP  Event type=Entry into national phase  Entry into the national phase in: Corresponding cc:  Designated or member state=AU     Event publication date=2018-04-19  Event code=AU/STCHG  Patent Status changed by the national office Corresponding cc:  Designated or member state=AU  LEGAL DETAILS FOR DESIGNATED STATE CA2869634  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专利类型码

A1

国别省市代码

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