Isoxazoline derivatives as antiparasitic agents 机翻标题: 暂无翻译,请尝试点击翻译按钮。

公开号/公开日
US2014011758 A1 2014-01-09 [US20140011758]US9061013 B2 2015-06-23 [US9061013] / 2014-01-092015-06-23
申请号/申请日
2012US-14005943 / 2012-03-08
发明人
VAILLANCOURT VALERIE A;WENDT JOHN A;KYNE GRAHAM M;MENON SANJAY;
申请人
AH USA 42;ZOETIS SERVICES;
主分类号
IPC分类号
A01N-043/80A01N-055/00A61K-031/42A61K-031/422A61K-045/06C07D-261/04C07D-413/10
摘要
(US9061013) This invention recites isoxazoline substituted derivatives of Formula (1) stereoisomers thereof, geometric isomers thereof, veterinarily acceptable salts 5 thereof, compositions thereof, and their use as a parasiticide in animals.  The variables A, W, R 1a, R 1b, R 1c, R 2, R 3, R 5, and n are as described herein.
机翻摘要
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地址
代理人
代理机构
;
优先权号
2011US-61466072 2011-03-22 2012US-14005943 2012-03-08 2012WO-IB51086 2012-03-08
主权利要求
(US9061013) We claim: 1.  A compound of Formula (1)   wherein A is phenyl, naphthyl, or heteroaryl where said heteroaryl contains 1 to 4 heteroatoms each independently selected from N, O and S;   W is N or CRc;   R1a, R1b, and R1c are each independently hydrogen, halo, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C0-C3alkylC3-C6 cycloalkyl, C1-C6haloalkoxy,  -- C(O)NH2,  -- SF5, or  -- S(O)pR;   R2 is halo, cyano, C1-C6alkyl, nitro, hydroxyl,  -- C(O)NH2, C2-C6alkenyl, C2-C6alkynyl, or  -- OR;   R3 is  -- C(X)NRaR4 or  -- NRaC(X)R4, where X is O, S, or NR6;   R4 is hydrogen, C1-C6alkyl, C0-C3alkylC3-C6cycloalkyl, C0-C3alkylphenyl, C0-C3alkylheteroaryl, or C0-C3alkylheterocycle; wherein said phenyl, heteroaryl, and heterocycle moieties are optionally substituted with one or more substituents selected from cyano, halo, hydroxyl, C1-C6alkoxy, C1-C6alkyl, and C1-C6haloalkoxy;    R5 is cyano, C1-C6alkyl, C1-C6haloalkyl,  -- C(O)NH2, C2-C6alkenyl, C2-C6alkynyl, C2-C6haloalkenyl, or C2-C6haloalkynyl; R6 is hydrogen, C1-C6alkyl, hydroxyl, cyano, nitro, S(O)pR, or C1-C6alkoxy;   R and R' are each independently C1-C6alkyl or C3-C6cycloalkyl;   Ra is hydrogen, C1-C6alkyl, C0-C3alkylC3-C6cycloalkyl, C(O)R4, or C(O)OR; wherein the alkyl and alkylcycloalkyl moiety is optionally substituted by cyano or at least one halo substituent;   Rb is hydrogen, C1-C6alkyl, C3-C6cycloalkyl, C0-C3alkylphenyl, C0-C3alkylheteroaryl, or C0-C3alkylheterocycle, each of which may be optionally substituted with at least one halo;   Rc is halo, hydroxyl, cyano, C1-C5alkyl, or C1-C5 haloalkyl;   each of R, R2, R3, and R4 C1-C6alkyl or C0-C3alkylC3-C6cycloalkyl can be optionally and independently substituted by one or more substituents selected from cyano, halo, hydroxyl, oxo, C1-C6alkoxy, C1-C6alkyl, hydroxyC1-C6alkyl-, and C1-C6haloalkoxy, and wherein R4 C1-C6alkyl and C0-C3alkylC3-C6cycloalkyl can be further optionally substituted by  -- S(O)pRb,  -- NRaRb,  -- NRaC(O)Rb,  -- SC(O)R', or  -- C(O)NRaRb;   n is the integer 0, 1, or 2, and when n is 2, each R2 may be identical or different from each other; and   p is the integer 0, 1, or 2;    stereoisomers thereof, geometric isomers thereof, and veterinarily acceptable salts thereof. 2. The compound of claim 1 having Formula (2) or (6)   wherein Y and Z are each independently C or N, and Y and Z are not both N;    stereoisomers thereof, and veterinarily acceptable salts thereof. 3. The compound of claim 2 wherein R1a, R1b, and R1c are each independently hydrogen, halo, cyano, C1-C6alkyl, or C1-C6haloalkyl;   R2 is halo, cyano, C1-C6alkyl, or hydroxyl;   R5 is trifluoromethyl; and   Ra is hydrogen or C1-C6alkyl optionally substituted by cyano or at least one halo substituent;    stereoisomers thereof, and veterinarily acceptable salts thereof. 4. The compound of claim 3 wherein R1a, R1b, and R1c are each independently hydrogen, chloro, fluoro, bromo, cyano, or trifluoromethyl;   R2 is halo, cyano, methyl, or hydroxyl;   Ra is hydrogen, methyl, or ethyl; and   R4 is C1-C6alkyl, C0-C3alkylC3-C6cycloalkyl, C0-C3alkylphenyl, C0-C3alkylheteroaryl, or C0-C3alkylheterocycle; wherein said phenyl, heteroaryl, and heterocycle moieties are optionally substituted with one or more substituents selected from cyano, halo, hydroxyl, or C1-C6alkyl; and wherein the R4 C1-C6alkyl or C0-C3alkylC3-C6cycloalkyl can be optionally and independently substituted by one or more substituents selected from cyano, halo, hydroxyl, C1-C6alkoxy, C1-C6alkyl,  -- S(O)pRb,  -- C(O)NRaRb,  -- NRaC(O)Rb, and hydroxyC1-C6alkyl-;    stereoisomers thereof, and veterinarily acceptable salts thereof. 5. The compound of claim 4 wherein Y and Z are both carbon;   R1a, R1b, and R1c are each independently hydrogen, chloro, fluoro, bromo, or trifluoromethyl;   Ra is hydrogen or methyl;   R4 is C1-C6alkyl or C0-C3alkylC3-C6cycloalkyl, each optionally substituted by one or more substituents selected from halo, hydroxyl, C1-C6alkyl, hydroxyC1-C6alkyl-,  -- C(O)NRaRb,  -- NRaC(O)Rb, and  -- S(O)pRb; and   n is the integer 0;    stereoisomers thereof, and veterinarily acceptable salts thereof. 6. The compound of claim 1 having Formula (7) or (11)   wherein Y and Z are each independently C or N, and Y and Z are not both N,    stereoisomers thereof, geometric isomers thereof, and veterinarily acceptable salts thereof. 7. The compound of claim 6 wherein R1a, R1b, and R1c are each independently hydrogen, halo, cyano, C1-C6alkyl, or C1-C6haloalkyl;   R2 is halo, cyano, C1-C6alkyl, or hydroxyl;   R5 is trifluoromethyl;   Ra is hydrogen or C1-C6alkyl optionally substituted by cyano or at least one halo substituent; and   Rc is halo, hydroxyl, cyano, or C1-C5 haloalkyl;    stereoisomers thereof, geometric isomers thereof, and veterinarily acceptable salts thereof. 8. The compound of claim 7 wherein R1a, R1b, and R1c are each independently hydrogen, chloro, fluoro, bromo, cyano, or trifluoromethyl;   R2 is halo, cyano, methyl, or hydroxyl;   Ra is hydrogen, methyl, or ethyl;   Rc is halo, hydroxyl, or trifluoromethyl; and   R4 is C1-C6alkyl, C0-C3alkylC3-C6cycloalkyl, C0-C3alkylphenyl, C0-C3alkylheteroaryl, or C0-C3alkylheterocycle; wherein said phenyl, heteroaryl, and heterocycle moieties are optionally substituted with one or more substituents selected from cyano, halo, hydroxyl, or C1-C6alkyl; and wherein the R4 C1-C6alkyl or C0-C3alkylC3-C6cycloalkyl can be optionally and independently substituted by one or more substituents selected from cyano, halo, hydroxyl, C1-C6alkoxy, C1-C6alkyl,  -- S(O)pRb,  -- C(O)NRaRb,  -- NRaC(O)Rb, and hydroxyC1-C6alkyl-;    stereoisomers thereof, geometric isomers thereof, and veterinarily acceptable salts thereof. 9. The compound of claim 8 wherein Y and Z are both carbon;    R1a, R1b, and R1c are each independently hydrogen, chloro, fluoro, bromo, or trifluoromethyl; Ra is hydrogen or methyl;   Rc is fluoro, chloro, hydroxyl, or trifluoromethyl;   R4 is C1-C6alkyl or C0-C3alkylC3-C6cycloalkyl, each optionally substituted by one or more substituents selected from halo, hydroxyl, C1-C6alkyl, hydroxyC1-C6alkyl-,  -- C(O)NRaRb,  -- NRaC(O)Rb, and  -- S(O)pRb; and   n is the integer 0;    stereoisomers thereof, geometric isomers thereof, and veterinarily acceptable salts thereof. 10. A compound selected from the group consisting of 3-hydroxy-3-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-cyclobutanecarboxylic acid (2,2,2-trifluoro-ethyl)-amide;   3-hydroxy-3-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-cyclobutanecarboxylic acid cyclopropylamide;   3-hydroxy-3-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-cyclobutanecarboxylic acid methylamide;   3-hydroxy-3-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-cyclobutanecarboxylic acid dimethylamide;   3-fluoro-3-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-cyclobutanecarboxylic acid cyclopropylamide;   3-fluoro-3-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-cyclobutanecarboxylic acid cyclopropylamide;   3-fluoro-3-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-cyclobutanecarboxylic acid (2,2,2-trifluoro-ethyl)-amide;   3-fluoro-3-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-cyclobutanecarboxylic acid (2,2,2-trifluoro-ethyl)-amide;   3-fluoro-3-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-cyclobutanecarboxylic acid methylamide;   3-fluoro-3-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-cyclobutanecarboxylic acid methylamide;   3-fluoro-3-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-cyclobutanecarboxylic acid dimethylamide;   3-fluoro-3-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-cyclobutanecarboxylic acid dimethylamide;   3-fluoro-3-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-cyclobutanecarboxylic acid;   3-fluoro-3-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-cyclobutanecarboxylic acid ethylamide;   3-fluoro-N-(2-oxo-2-((2,2,2-trifluoroethyl)amino)ethyl)-3-(4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)cyclobutanecarboxamide;   1-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-azetidine-3-carboxylic acid cyclopropylamide;   1-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-azetidine-3-carboxylic acid methylamide;   1-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-azetidine-3-carboxylic acid (2,2,2-trifluoro-ethyl)amide;   1-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}azetidine-3-carboxylic acid dimethylamide;   1-{2-chloro-4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-azetidine-3-carboxylic acid methylamide;   1-{2-chloro-4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-azetidine-3-carboxylic acid (2,2,2-trifluoro-ethyl)-amide;   1-{2-chloro-4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-azetidine-3-carboxylic acid cyclopropylamide;   1-{2-chloro-4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-azetidine-3-carboxylic acid dimethylamide;   N-(3-fluoro-3-(4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)cyclobutyl)cyclopropanecarboxamide; and   N-(3-fluoro-3-(4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)cyclobutyl)-2-(methylsulfonyl)acetamide;   stereoisomers thereof, geometric isomers thereof, and veterinarily acceptable salts thereof. 11. A pharmaceutical or veterinary composition comprising a therapeutic amount of a compound of Formula (1)   wherein A is phenyl, naphthyl, or heteroaryl where said heteroaryl contains 1 to 4 heteroatoms each independently selected from N, O and S;   W is N or CRc;   R1a, R1b, and R1c are each independently hydrogen, halo, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C0-C3alkylC3-C6 cycloalkyl, C1-C6haloalkoxy,  -- C(O)NH2,  -- SF5, or  -- S(O)pR;   R2 is halo, cyano, C1-C6alkyl, nitro, hydroxyl,  -- C(O)NH2, C2-C6alkenyl, C2-C6alkynyl, or  -- OR;   R3 is  -- C(X)NRaR4 or  -- NRaC(X)R4, where X is O, S, or NR6;   R4 is hydrogen, C1-C6alkyl, C0-C3alkylC3-C6cycloalkyl, C0-C3alkylphenyl, C0-C3alkylheteroaryl, or C0-C3alkylheterocycle; wherein said phenyl, heteroaryl, and heterocycle moieties are optionally substituted with one or more substituents selected from cyano, halo, hydroxyl, C1-C6alkoxy, C1-C6alkyl, and C1-C6haloalkoxy;   R5 is cyano, C1-C6alkyl, C1-C6haloalkyl,  -- C(O)NH2, C2-C6alkenyl, C2-C6alkynyl, C2-C6haloalkenyl, or C2-C6haloalkynyl;   R6 is hydrogen, C1-C6alkyl, hydroxyl, cyano, nitro, S(O)pR, or C1-C6alkoxy;   R and R' are each independently C1-C6alkyl or C3-C6cycloalkyl;   Ra is hydrogen, C1-C6alkyl, C0-C3alkylC3-C6cycloalkyl, C(O)R4, or C(O)OR; wherein the alkyl and alkylcycloalkyl moiety is optionally substituted by cyano or at least one halo substituent;   Rb is hydrogen, C1-C6alkyl, C3-C6cycloalkyl, C0-C3alkylphenyl, C0-C3alkylheteroaryl, or C0-C3alkylheterocycle, each of which may be optionally substituted with at least one halo;   Rc is halo, hydroxyl, cyano, C1-C5alkyl, or C1-C5 haloalkyl;   each of R, R2, R3, and R4 C1-C6alkyl or C0-C3alkylC3-C6cycloalkyl can be optionally and independently substituted by one or more substituents selected from cyano, halo, hydroxyl, oxo, C1-C6alkoxy, C1-C6alkyl, hydroxyC1-C6alkyl-, and C1-C6haloalkoxy, and wherein R4 C1-C6alkyl and C0-C3alkylC3-C6cycloalkyl can be further optionally substituted by  -- S(O)pRb,  -- NRaRb,  -- NRaC(O)Rb,  -- SC(O)R', or  -- C(O)NRaRb;   n is the integer 0, 1, or 2, and when n is 2, each R2 may be identical or different from each other; and   p is the integer 0, 1, or 2;    stereoisomers thereof, geometric isomers thereof, and veterinarily acceptable salts thereof. 12. The pharmaceutical or veterinary composition of claim 11 further comprising a veterinarily acceptable excipient, diluent, or carrier. 13. The pharmaceutical or veterinary composition of claim 12 further comprising at least one additional veterinary agent, wherein said additional veterinary agent is selected from the group consisting of avermectin, selamectin, doramectin, moxidectin, eprinomectin, milbemycin, milbemycin oxime, pyriproxyfen, DEET, demiditraz, amitraz, fipronil, methoprene, hydroprene, metaflumizone, permethrin, pyrethrin, and spinosad, or mixtures thereof. 14. A method for the treatment of an animal with a parasitic infection or infestation comprising administering to said animal in need thereof an effective amount of a compound of Formula (1)   wherein A is phenyl, naphthyl, or heteroaryl where said heteroaryl contains 1 to 4 heteroatoms each independently selected from N, O and S;   W is N or CRc;   R1a, R1b, and R1c are each independently hydrogen, halo, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C0-C3alkylC3-C6 cycloalkyl, C1-C6haloalkoxy,  -- C(O)NH2,  -- SF5, or  -- S(O)pR;   R2 is halo, cyano, C1-C6alkyl, nitro, hydroxyl,  -- C(O)NH2, C2-C6alkenyl, C2-C6alkynyl, or  -- OR;   R3 is  -- C(X)NRaR4 or  -- NRaC(X)R4, where X is O, S, or NR6;   R4 is hydrogen, C1-C6alkyl, C0-C3alkylC3-C6cycloalkyl, C0-C3alkylphenyl, C0-C3alkylheteroaryl, or C0-C3alkylheterocycle; wherein said phenyl, heteroaryl, and heterocycle moieties are optionally substituted with one or more substituents selected from cyano, halo, hydroxyl, C1-C6alkoxy, C1-C6alkyl, and C1-C6haloalkoxy;   R5 is cyano, C1-C6alkyl, C1-C6haloalkyl,  -- C(O)NH2, C2-C6alkenyl, C2-C6alkynyl, C2-C6haloalkenyl, or C2-C6haloalkynyl;   R6 is hydrogen, C1-C6alkyl, hydroxyl, cyano, nitro, S(O)pR, or C1-C6alkoxy;   R and R' are each independently C1-C6alkyl or C3-C6cycloalkyl;   Ra is hydrogen, C1-C6alkyl, C0-C3alkylC3-C6cycloalkyl, C(O)R4, or C(O)OR; wherein the alkyl and alkylcycloalkyl moiety is optionally substituted by cyano or at least one halo substituent;   Rb is hydrogen, C1-C6alkyl, C3-C6cycloalkyl, C0-C3alkylphenyl, C0-C3alkylheteroaryl, or C0-C3alkylheterocycle, each of which may be optionally substituted with at least one halo;   Rc is halo, hydroxyl, cyano, C1-C5alkyl, or C1-C5 haloalkyl;   each of R, R2, R3, and R4 C1-C6alkyl or C0-C3alkylC3-C6cycloalkyl can be optionally and independently substituted by one or more substituents selected from cyano, halo, hydroxyl, oxo, C1-C6alkoxy, C1-C6alkyl, hydroxyC1-C6alkyl-, and C1-C6haloalkoxy, and wherein R4 C1-C6alkyl and C0-C3alkylC3-C6cycloalkyl can be further optionally substituted by  -- S(O)pRb,  -- NRaRb,  -- NRaC(O)Rb,  -- SC(O)R', or  -- C(O)NRaRb;   n is the integer 0, 1, or 2, and when n is 2, each R2 may be identical or different from each other; and   p is the integer 0, 1, or 2;    stereoisomers thereof, geometric isomers thereof, and veterinarily acceptable salts thereof. 15. The method of claim 14 wherein the compound is administered topically, orally, or subcutaneously and wherein said animal is a companion animal or livestock.
法律状态
(US9061013) LEGAL DETAILS FOR US2014011758  Actual or expected expiration date=2032-06-07    Legal state=ALIVE    Status=GRANTED     Event publication date=2012-03-08  Event code=US/APP  Event indicator=Pos  Event type=Examination events  Application details  Application country=US US14005943  Application date=2012-03-08  Standardized application number=2012US-14005943     Event publication date=2012-03-08  Event code=US/EXMR  Event type=Administrative notifications  USPTO Examiner Name Primary Examiner: SAEED, KAMAL A    Event publication date=2012-03-08  Event code=US/ART  Event type=Administrative notifications  USPTO Art Group  ART=1626     Event publication date=2012-03-08  Event code=US/ENT  Event type=Administrative notifications  Entity Status Set to Undiscounted Business Entity Status: UNDISCOUNTED    Event publication date=2012-03-08  Event code=US/AIA  Event type=Administrative notifications  First Inventor File Indicated:  AIA=No     Event publication date=2012-03-08  Event code=US/DK  Event type=Examination events  Attorney Docket Number Docket Nbr: PC71753A    Event publication date=2012-03-08  Event code=US/CUST  Event type=Examination events  Attorney/Agent Customer Number Customer Nbr: 110408    Event publication date=2012-07-16  Event code=US/AS  Event type=Change of name or address  Event type=Reassignment  Assignment  Effective date of the event=2012-07-16  ASSIGNMENT OF ASSIGNORS INTEREST ASSIGNORS:KYNE, GRAHAM M. 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