JP5634510B2 - イミノ糖ならびにブニヤウイルスおよびトガウイルス疾患を治療する方法 - Google Patents
イミノ糖ならびにブニヤウイルスおよびトガウイルス疾患を治療する方法 Download PDFInfo
- Publication number
- JP5634510B2 JP5634510B2 JP2012515167A JP2012515167A JP5634510B2 JP 5634510 B2 JP5634510 B2 JP 5634510B2 JP 2012515167 A JP2012515167 A JP 2012515167A JP 2012515167 A JP2012515167 A JP 2012515167A JP 5634510 B2 JP5634510 B2 JP 5634510B2
- Authority
- JP
- Japan
- Prior art keywords
- virus
- pharmaceutical composition
- composition according
- fever
- alkyl group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 32
- 201000010099 disease Diseases 0.000 title claims description 27
- 238000000034 method Methods 0.000 title description 60
- 241000713112 Orthobunyavirus Species 0.000 title description 8
- 241000700605 Viruses Species 0.000 claims description 94
- 150000001875 compounds Chemical class 0.000 claims description 40
- 239000008194 pharmaceutical composition Substances 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 241000713124 Rift Valley fever virus Species 0.000 claims description 17
- 241000710959 Venezuelan equine encephalitis virus Species 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- -1 N- {4'- azido-2'-nitrophenyl} -6-aminohexyl Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- FTSCEGKYKXESFF-LXTVHRRPSA-N N-nonyldeoxynojirimycin Chemical compound CCCCCCCCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO FTSCEGKYKXESFF-LXTVHRRPSA-N 0.000 claims description 12
- 241000150350 Peribunyaviridae Species 0.000 claims description 12
- 241000710924 Togaviridae Species 0.000 claims description 12
- LXBIFEVIBLOUGU-JGWLITMVSA-N duvoglustat Chemical compound OC[C@H]1NC[C@H](O)[C@@H](O)[C@@H]1O LXBIFEVIBLOUGU-JGWLITMVSA-N 0.000 claims description 11
- 230000009385 viral infection Effects 0.000 claims description 10
- 241001502567 Chikungunya virus Species 0.000 claims description 8
- LXBIFEVIBLOUGU-UHFFFAOYSA-N Deoxymannojirimycin Natural products OCC1NCC(O)C(O)C1O LXBIFEVIBLOUGU-UHFFFAOYSA-N 0.000 claims description 8
- 206010037660 Pyrexia Diseases 0.000 claims description 8
- 241000150452 Orthohantavirus Species 0.000 claims description 7
- 201000009182 Chikungunya Diseases 0.000 claims description 6
- 206010066919 Epidemic polyarthritis Diseases 0.000 claims description 6
- 206010061192 Haemorrhagic fever Diseases 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 201000003075 Crimean-Congo hemorrhagic fever Diseases 0.000 claims description 5
- 206010014611 Encephalitis venezuelan equine Diseases 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 5
- 208000000705 Rift Valley Fever Diseases 0.000 claims description 5
- 241000150278 Seoul orthohantavirus Species 0.000 claims description 5
- 208000002687 Venezuelan Equine Encephalomyelitis Diseases 0.000 claims description 5
- 201000009145 Venezuelan equine encephalitis Diseases 0.000 claims description 5
- 241000710929 Alphavirus Species 0.000 claims description 4
- 241000150489 Andes orthohantavirus Species 0.000 claims description 4
- 206010014599 encephalitis Diseases 0.000 claims description 4
- 125000006755 (C2-C20) alkyl group Chemical group 0.000 claims description 3
- 208000006825 Eastern Equine Encephalomyelitis Diseases 0.000 claims description 3
- 201000005804 Eastern equine encephalitis Diseases 0.000 claims description 3
- 241000710945 Eastern equine encephalitis virus Species 0.000 claims description 3
- 206010014587 Encephalitis eastern equine Diseases 0.000 claims description 3
- 208000035751 Epidemic nephropathy Diseases 0.000 claims description 3
- 241000608292 Mayaro virus Species 0.000 claims description 3
- 241000710942 Ross River virus Species 0.000 claims description 3
- 201000007009 Ross river fever Diseases 0.000 claims description 3
- 241000710799 Rubella virus Species 0.000 claims description 3
- 241000710961 Semliki Forest virus Species 0.000 claims description 3
- 241000150288 Sin Nombre orthohantavirus Species 0.000 claims description 3
- 241000710960 Sindbis virus Species 0.000 claims description 3
- 241000710951 Western equine encephalitis virus Species 0.000 claims description 3
- 230000002612 cardiopulmonary effect Effects 0.000 claims description 3
- 230000002988 nephrogenic effect Effects 0.000 claims description 3
- 201000005404 rubella Diseases 0.000 claims description 3
- 230000035900 sweating Effects 0.000 claims description 3
- 208000011580 syndromic disease Diseases 0.000 claims description 3
- 206010014614 Encephalitis western equine Diseases 0.000 claims description 2
- 208000000832 Equine Encephalomyelitis Diseases 0.000 claims description 2
- 201000000239 Phlebotomus fever Diseases 0.000 claims description 2
- 208000005466 Western Equine Encephalomyelitis Diseases 0.000 claims description 2
- 201000005806 Western equine encephalitis Diseases 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 23
- 238000004809 thin layer chromatography Methods 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000012043 crude product Substances 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 10
- 235000000346 sugar Nutrition 0.000 description 10
- 230000003612 virological effect Effects 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- UQRORFVVSGFNRO-UTINFBMNSA-N miglustat Chemical compound CCCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO UQRORFVVSGFNRO-UTINFBMNSA-N 0.000 description 8
- 238000003556 assay Methods 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 125000001841 imino group Chemical group [H]N=* 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 208000036142 Viral infection Diseases 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 231100000673 dose–response relationship Toxicity 0.000 description 6
- 208000015181 infectious disease Diseases 0.000 description 6
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 5
- 125000003435 aroyl group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 125000001188 haloalkyl group Chemical group 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- CXOHZQDMLUIQEE-UHFFFAOYSA-N 6-propoxyhexan-1-ol Chemical compound CCCOCCCCCCO CXOHZQDMLUIQEE-UHFFFAOYSA-N 0.000 description 4
- GTFGSFASQILIGG-UHFFFAOYSA-N 6-propoxyhexanal Chemical compound CCCOCCCCCC=O GTFGSFASQILIGG-UHFFFAOYSA-N 0.000 description 4
- NMPAUWFFDKJTNR-UHFFFAOYSA-N 9-methoxynonan-1-ol Chemical compound COCCCCCCCCCO NMPAUWFFDKJTNR-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
- MXBRUXICXRNFPC-UHFFFAOYSA-N 9-methoxynonanal Chemical compound COCCCCCCCCC=O MXBRUXICXRNFPC-UHFFFAOYSA-N 0.000 description 3
- 241000150488 Bayou orthohantavirus Species 0.000 description 3
- 241000150523 Black Creek Canal orthohantavirus Species 0.000 description 3
- 241000150528 Dobrava-Belgrade orthohantavirus Species 0.000 description 3
- 241000168432 New York hantavirus Species 0.000 description 3
- 241000223960 Plasmodium falciparum Species 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000012894 fetal calf serum Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000002458 infectious effect Effects 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 244000052769 pathogen Species 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- 210000003501 vero cell Anatomy 0.000 description 3
- 241001493160 California encephalitis virus Species 0.000 description 2
- 241000430977 Choclo virus Species 0.000 description 2
- 241000283086 Equidae Species 0.000 description 2
- 241000283073 Equus caballus Species 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 241000142710 Isla Vista hantavirus Species 0.000 description 2
- 241001494444 Jamestown Canyon virus Species 0.000 description 2
- 241000150551 Khabarovsk orthohantavirus Species 0.000 description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
- 229930182816 L-glutamine Natural products 0.000 description 2
- 241000150547 Laguna Negra orthohantavirus Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000216220 Muleshoe hantavirus Species 0.000 description 2
- 241000150218 Orthonairovirus Species 0.000 description 2
- 241000712894 Orthotospovirus Species 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- 241000150258 Prospect Hill orthohantavirus Species 0.000 description 2
- 241001503177 Rio Segundo hantavirus Species 0.000 description 2
- 241000710801 Rubivirus Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 241000150287 Thailand orthohantavirus Species 0.000 description 2
- 241000150289 Tula orthohantavirus Species 0.000 description 2
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 2
- 230000019552 anatomical structure morphogenesis Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
- 239000012091 fetal bovine serum Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000002502 liposome Substances 0.000 description 2
- 230000035800 maturation Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- 239000000651 prodrug Substances 0.000 description 2
- 229940002612 prodrug Drugs 0.000 description 2
- 239000012925 reference material Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229960005322 streptomycin Drugs 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical compound CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
- OLYHECNPMKMYII-LXTVHRRPSA-N (2r,3r,4r,5s)-2-(hydroxymethyl)-1-(6-propoxyhexyl)piperidine-3,4,5-triol Chemical compound CCCOCCCCCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO OLYHECNPMKMYII-LXTVHRRPSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- 229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920000936 Agarose Polymers 0.000 description 1
- 241000832207 Alenquer virus Species 0.000 description 1
- 241000238421 Arthropoda Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 208000008889 California Encephalitis Diseases 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 241000832208 Chagres virus Species 0.000 description 1
- 241000832206 Chandiru virus Species 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000149824 Dugbe orthonairovirus Species 0.000 description 1
- 206010014584 Encephalitis california Diseases 0.000 description 1
- 241000283074 Equus asinus Species 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 208000008913 Hantavirus Infections Diseases 0.000 description 1
- 208000021727 Hantavirus hemorrhagic fever with renal syndrome Diseases 0.000 description 1
- 208000032982 Hemorrhagic Fever with Renal Syndrome Diseases 0.000 description 1
- 241000149826 Hughes orthonairovirus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- 201000009908 La Crosse encephalitis Diseases 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 208000032420 Latent Infection Diseases 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 229920002230 Pectic acid Polymers 0.000 description 1
- 241000255129 Phlebotominae Species 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 241000149820 Sakhalin orthonairovirus Species 0.000 description 1
- 241000724318 Tenuivirus Species 0.000 description 1
- 241000149831 Thiafora orthonairovirus Species 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 241000713154 Toscana virus Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- AEMOLEFTQBMNLQ-BKBMJHBISA-N alpha-D-galacturonic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-BKBMJHBISA-N 0.000 description 1
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940050390 benzoate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 230000003915 cell function Effects 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 208000037771 disease arising from reactivation of latent virus Diseases 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 208000029629 hantavirus infectious disease Diseases 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 230000002934 lysing effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229960001512 miglustat Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- PGSADBUBUOPOJS-UHFFFAOYSA-N neutral red Chemical compound Cl.C1=C(C)C(N)=CC2=NC3=CC(N(C)C)=CC=C3N=C21 PGSADBUBUOPOJS-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 229950010765 pivalate Drugs 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013595 supernatant sample Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- RSJKGSCJYJTIGS-BJUDXGSMSA-N undecane Chemical class CCCCCCCCCC[11CH3] RSJKGSCJYJTIGS-BJUDXGSMSA-N 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18661409P | 2009-06-12 | 2009-06-12 | |
| US61/186,614 | 2009-06-12 | ||
| PCT/US2010/038247 WO2010144759A1 (en) | 2009-06-12 | 2010-06-11 | Iminosugars and methods of treating bunyaviral and togaviral diseases |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012530061A JP2012530061A (ja) | 2012-11-29 |
| JP2012530061A5 JP2012530061A5 (https=) | 2014-04-10 |
| JP5634510B2 true JP5634510B2 (ja) | 2014-12-03 |
Family
ID=43306958
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012515167A Expired - Fee Related JP5634510B2 (ja) | 2009-06-12 | 2010-06-11 | イミノ糖ならびにブニヤウイルスおよびトガウイルス疾患を治療する方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US8426445B2 (https=) |
| EP (1) | EP2440205B1 (https=) |
| JP (1) | JP5634510B2 (https=) |
| KR (1) | KR101463661B1 (https=) |
| CN (1) | CN102639133B (https=) |
| CA (1) | CA2765086C (https=) |
| ES (1) | ES2524361T3 (https=) |
| WO (1) | WO2010144759A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2398321B1 (en) | 2009-02-23 | 2015-11-25 | United Therapeutics Corporation | Iminosugars and methods of treating viral diseases |
| ES2524361T3 (es) * | 2009-06-12 | 2014-12-05 | United Therapeutics Corporation | Iminoazúcares para su uso en el tratamiento de enfermedades por bunyavirus y togavirus |
| KR20150035767A (ko) | 2012-06-06 | 2015-04-07 | 유니터 바이롤로지, 엘엘씨 | 신규 이미노당 및 그의 용도 |
| CN102875450B (zh) * | 2012-10-25 | 2015-04-08 | 上海丝绸集团股份有限公司 | 一种从桑叶中提取制备1-脱氧野尻霉素的工艺方法 |
| JP2016513729A (ja) * | 2013-03-15 | 2016-05-16 | ユニザー ヴィロロジー，エルエルシー | 抗菌化合物 |
| JP6456393B2 (ja) | 2013-09-16 | 2019-01-23 | エマージェント バイロロジー エルエルシー | デオキシノジリマイシン誘導体およびその使用方法 |
| CN104357583B (zh) * | 2014-10-31 | 2016-11-09 | 中国检验检疫科学研究院 | 巴马哈森林病毒的实时荧光rt-pcr检测试剂盒和方法 |
| BR112017008898B1 (pt) * | 2014-11-05 | 2022-11-29 | Emergent Virology Llc | Compostos de iminoaçúcares, suas composições farmacêuticas e usos dos mesmos para tratar doenças virais |
| CN114681472B (zh) * | 2019-03-13 | 2023-06-30 | 中国人民解放军军事科学院军事医学研究院 | 氨基葡萄糖及其衍生物作为抗病毒药物的应用 |
Family Cites Families (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1555654A (en) | 1977-06-25 | 1979-11-14 | Exxon Research Engineering Co | Agricultural burner apparatus |
| NO154918C (no) | 1977-08-27 | 1987-01-14 | Bayer Ag | Analogifremgangsmaate til fremstilling av terapeutisk aktive derivater av 3,4,5-trihydroksypiperidin. |
| DE2834122A1 (de) | 1978-08-03 | 1980-02-14 | Bayer Ag | Verfahren zur herstellung von 6-amino-6-desoxy-l-sorbose |
| DE2839309A1 (de) | 1978-09-09 | 1980-03-27 | Bayer Ag | 3,4,5-trihydroxypiperidin-derivate |
| DE2853573A1 (de) | 1978-12-12 | 1980-07-03 | Bayer Ag | Herstellung von n-substituierten derivaten des l-desoxynojirimycins |
| DE3038901A1 (de) | 1980-10-15 | 1982-05-06 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von n-substituierten derivaten des 1-desoxynojirimycins |
| DE3611841A1 (de) | 1986-04-09 | 1987-10-15 | Bayer Ag | Verfahren zur herstellung von 1-desoxynojirimycin und dessen n-derivaten |
| US5103008A (en) | 1989-08-17 | 1992-04-07 | Monsanto Company | Compound, N-butyl-deoxynojirimycin-6-phosphate |
| US5043273A (en) | 1989-08-17 | 1991-08-27 | Monsanto Company | Phosphorylated glycosidase inhibitor prodrugs |
| US4994572A (en) | 1989-10-12 | 1991-02-19 | Monsanto Company | Synthesis of nojirimycin derivatives |
| US5030638A (en) | 1990-02-26 | 1991-07-09 | G. D. Searle & Co. | Method of antiviral enhancement |
| US5200523A (en) | 1990-10-10 | 1993-04-06 | Monsanto Company | Synthesis of nojirimycin derivatives |
| US5206251A (en) | 1992-04-01 | 1993-04-27 | G. D. Searle & Co. | 2- and 3- amino and azido derivatives of 1,5-iminosugars |
| US5399567A (en) | 1993-05-13 | 1995-03-21 | Monsanto Company | Method of treating cholera |
| AU1876095A (en) | 1994-02-25 | 1995-09-11 | G.D. Searle & Co. | Use of 1-deoxynojirimycin and its derivatives for treating mammals infected with respiratory syncytial virus |
| KR20010033028A (ko) | 1997-12-11 | 2001-04-25 | 더 챈슬러 마스터즈 앤드 스칼라스 오브 더 유니버시티 오브 옥스포드 | 막-관련 바이러스 복제의 억제 |
| DE69932154T2 (de) | 1998-02-12 | 2007-05-31 | G.D. Searle Llc, Chicago | Verwendung von n-substituirten-1,5-dideoxy-1,5-imino-d-glucitolen zur behandlung von hepatitis infektionen |
| US6689759B1 (en) | 1998-02-12 | 2004-02-10 | G. D. Searle & Co. | Methods of Treating hepatitis virus infections with N-substituted-1,5-dideoxy-1,5-imino-d-glucitol compounds in combination therapy |
| EP1714676A3 (en) | 1998-02-12 | 2006-11-15 | G.D. Searle LLC. | Use of N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compounds for treating hepatitis virus infections |
| US6610703B1 (en) | 1998-12-10 | 2003-08-26 | G.D. Searle & Co. | Method for treatment of glycolipid storage diseases |
| GB9828474D0 (en) | 1998-12-24 | 1999-02-17 | British Aerospace | Surface topology inspection |
| ATE402701T1 (de) | 1999-02-12 | 2008-08-15 | United Therapeutics Corp | N-(8,8,8-trifluorooctyl)-1,5-dideoxy-1,5-imino- - glucitol zur behandlung von hepatitis-virus- infektionen |
| GB0100889D0 (en) | 2001-01-12 | 2001-02-21 | Oxford Glycosciences Uk Ltd | Compounds |
| EP1196190B1 (en) | 1999-07-26 | 2003-03-19 | G.D. SEARLE & CO. | Use of long-chain n-alkyl derivatives of deoxynojirimycin and a glucocerebrosidase enzyme for the manufacture of a medicament for the treatment of glycolipid storage diseases |
| US7256005B2 (en) | 1999-08-10 | 2007-08-14 | The Chancellor, Masters And Scholars Of The University Of Oxford | Methods for identifying iminosugar derivatives that inhibit HCV p7 ion channel activity |
| EP2857036B1 (en) | 2003-01-31 | 2016-12-21 | Mount Sinai School of Medicine of New York University | Combination therapy for treating protein deficiency disorders |
| US7446098B2 (en) | 2003-02-18 | 2008-11-04 | Mount Sinai School Of Medicine Of New York University | Combination therapy for treating protein deficiencies |
| US7135575B2 (en) * | 2003-03-03 | 2006-11-14 | Array Biopharma, Inc. | P38 inhibitors and methods of use thereof |
| US20060211752A1 (en) | 2004-03-16 | 2006-09-21 | Kohn Leonard D | Use of phenylmethimazoles, methimazole derivatives, and tautomeric cyclic thiones for the treatment of autoimmune/inflammatory diseases associated with toll-like receptor overexpression |
| US20050256168A1 (en) | 2004-04-28 | 2005-11-17 | Block Timothy M | Compositions for oral administration for the treatment of interferon-responsive disorders |
| US7524829B2 (en) | 2004-11-01 | 2009-04-28 | Avi Biopharma, Inc. | Antisense antiviral compounds and methods for treating a filovirus infection |
| GB0501352D0 (en) * | 2005-01-21 | 2005-03-02 | Slingsby Jason H | Use of glycosylation modulators in combination with membrane fusion inhibitors for treatment of infections caused by viruses bearing glycosylated envelope |
| CA2601797A1 (en) | 2005-03-16 | 2006-09-21 | University Of Oxford | Mannose immunogens for hiv-1 |
| EP3782655A1 (en) | 2005-05-17 | 2021-02-24 | Amicus Therapeutics, Inc. | A method for the treatment of pompe disease using 1-deoxynojirimycin and derivatives |
| KR20080031474A (ko) | 2005-07-27 | 2008-04-08 | 유니버시티 오브 플로리다 리서치 파운데이션, 아이엔씨. | 안구 질환의 치료를 위한 열충격의 사용 |
| US20100004156A1 (en) | 2005-07-27 | 2010-01-07 | Shalesh Kaushal | Small Compounds That Correct Protein Misfolding and Uses Thereof |
| US20070244184A1 (en) | 2006-01-09 | 2007-10-18 | Simon Fraser University | Glycosidase inhibitors and methods of synthesizing same |
| DE602007008870D1 (de) | 2006-04-24 | 2010-10-14 | Amc Amsterdam | Verbessertes verfahren zur behandlung von cystischer fibrose |
| CN104876855A (zh) * | 2006-05-24 | 2015-09-02 | 联合治疗公司 | 脱氧吉瑞霉素和d-阿拉伯胶素醇类似物及使用方法 |
| JP2009545621A (ja) | 2006-08-02 | 2009-12-24 | ユナイテッド セラピューティクス コーポレーション | ウィルス感染症のリポソーム処置 |
| KR20090057035A (ko) | 2006-08-21 | 2009-06-03 | 유나이티드 세러퓨틱스 코오포레이션 | 바이러스 감염의 치료를 위한 병용 요법 |
| WO2008068548A1 (en) | 2006-12-08 | 2008-06-12 | Institut Necker | Use of inhibitors of the glycosylation process for the prevention and treatment of genetic diseases |
| KR20100127842A (ko) | 2008-03-26 | 2010-12-06 | 유니버시티 오브 옥스퍼드 | 소포체 표적화 리포좀 |
| WO2010027996A1 (en) * | 2008-09-02 | 2010-03-11 | Institute For Hepatitis And Virus Research | Novel imino sugar derivatives demonstrate potent antiviral activity and reduced toxicity |
| US8703744B2 (en) * | 2009-03-27 | 2014-04-22 | The Chancellor, Masters And Scholars Of The University Of Oxford | Cholesterol level lowering liposomes |
| ES2524361T3 (es) * | 2009-06-12 | 2014-12-05 | United Therapeutics Corporation | Iminoazúcares para su uso en el tratamiento de enfermedades por bunyavirus y togavirus |
-
2010
- 2010-06-11 ES ES10786885.3T patent/ES2524361T3/es active Active
- 2010-06-11 KR KR1020127000433A patent/KR101463661B1/ko not_active Expired - Fee Related
- 2010-06-11 US US12/813,882 patent/US8426445B2/en not_active Expired - Fee Related
- 2010-06-11 JP JP2012515167A patent/JP5634510B2/ja not_active Expired - Fee Related
- 2010-06-11 CN CN201080033499.6A patent/CN102639133B/zh not_active Expired - Fee Related
- 2010-06-11 EP EP10786885.3A patent/EP2440205B1/en not_active Not-in-force
- 2010-06-11 WO PCT/US2010/038247 patent/WO2010144759A1/en not_active Ceased
- 2010-06-11 CA CA2765086A patent/CA2765086C/en not_active Expired - Fee Related
-
2013
- 2013-02-07 US US13/761,583 patent/US8748460B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN102639133B (zh) | 2015-03-11 |
| US8426445B2 (en) | 2013-04-23 |
| EP2440205B1 (en) | 2014-08-27 |
| US20130150405A1 (en) | 2013-06-13 |
| US8748460B2 (en) | 2014-06-10 |
| CA2765086A1 (en) | 2010-12-16 |
| KR20120038960A (ko) | 2012-04-24 |
| US20100317696A1 (en) | 2010-12-16 |
| EP2440205A4 (en) | 2013-04-24 |
| CA2765086C (en) | 2015-12-15 |
| ES2524361T3 (es) | 2014-12-05 |
| JP2012530061A (ja) | 2012-11-29 |
| EP2440205A1 (en) | 2012-04-18 |
| KR101463661B1 (ko) | 2014-11-19 |
| CN102639133A (zh) | 2012-08-15 |
| WO2010144759A1 (en) | 2010-12-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5634510B2 (ja) | イミノ糖ならびにブニヤウイルスおよびトガウイルス疾患を治療する方法 | |
| US9943532B2 (en) | Iminosugars and methods of treating viral diseases | |
| JP5752689B2 (ja) | フィロウイルス疾患を治療するイミノ糖および方法 | |
| JP5951996B2 (ja) | イミノ糖及びアレナウイルス感染症を治療する方法 | |
| HK1165675B (en) | Iminosugars and methods of treating arenaviral infections | |
| HK1172270A (en) | Iminosugars and methods of treating bunyaviral and togaviral diseases |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130410 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20130410 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140221 |
|
| A871 | Explanation of circumstances concerning accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A871 Effective date: 20140221 |
|
| A975 | Report on accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A971005 Effective date: 20140305 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140311 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20140610 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20140617 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140910 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20141007 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20141014 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |