CA2529761C - Compounds, compositions and methods for treatment and prevention of orthopoxvirus infections and associated diseases - Google Patents
Compounds, compositions and methods for treatment and prevention of orthopoxvirus infections and associated diseases Download PDFInfo
- Publication number
- CA2529761C CA2529761C CA2529761A CA2529761A CA2529761C CA 2529761 C CA2529761 C CA 2529761C CA 2529761 A CA2529761 A CA 2529761A CA 2529761 A CA2529761 A CA 2529761A CA 2529761 C CA2529761 C CA 2529761C
- Authority
- CA
- Canada
- Prior art keywords
- dioxo
- isoindol
- group
- benzamide
- octahydro
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 31
- 201000010099 disease Diseases 0.000 title claims abstract description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 24
- 238000011282 treatment Methods 0.000 title claims abstract description 23
- 150000001875 compounds Chemical class 0.000 title claims description 147
- 239000000203 mixture Substances 0.000 title claims description 30
- 206010069586 Orthopox virus infection Diseases 0.000 title claims description 16
- 230000002265 prevention Effects 0.000 title description 5
- 241000700629 Orthopoxvirus Species 0.000 claims abstract description 37
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 117
- 150000003254 radicals Chemical class 0.000 claims description 104
- -1 carboxy, cyano, amino Chemical group 0.000 claims description 62
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 52
- 239000001257 hydrogen Substances 0.000 claims description 52
- 208000015181 infectious disease Diseases 0.000 claims description 48
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 42
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims description 42
- 125000003368 amide group Chemical group 0.000 claims description 41
- 229910052736 halogen Inorganic materials 0.000 claims description 41
- 150000002367 halogens Chemical class 0.000 claims description 41
- 229940124530 sulfonamide Drugs 0.000 claims description 41
- 150000003456 sulfonamides Chemical class 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 40
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 40
- 125000004414 alkyl thio group Chemical group 0.000 claims description 38
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 38
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 37
- 241000700605 Viruses Species 0.000 claims description 35
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 34
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 34
- SANSPEXFDMFMEB-UHFFFAOYSA-N 2-amino-2-iminoacetamide Chemical compound NC(=N)C(N)=O SANSPEXFDMFMEB-UHFFFAOYSA-N 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- 241000700647 Variola virus Species 0.000 claims description 31
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 28
- QKDLQFSLLCQTOH-UHFFFAOYSA-N Trichodonin Natural products C1C(O)C2C3(COC(=O)C)C(C=O)C(C)(C)CCC3OC(=O)C22C(=O)C(=C)C1C2 QKDLQFSLLCQTOH-UHFFFAOYSA-N 0.000 claims description 27
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 27
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 24
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- 125000002883 imidazolyl group Chemical group 0.000 claims description 21
- 125000002971 oxazolyl group Chemical group 0.000 claims description 21
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 21
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 21
- 125000004076 pyridyl group Chemical group 0.000 claims description 21
- 125000000335 thiazolyl group Chemical group 0.000 claims description 21
- 125000001544 thienyl group Chemical group 0.000 claims description 21
- 229930192474 thiophene Natural products 0.000 claims description 21
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 20
- 241000700618 Vaccinia virus Species 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 20
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 19
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 19
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 19
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 18
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 18
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 18
- 125000002541 furyl group Chemical group 0.000 claims description 18
- 125000004122 cyclic group Chemical group 0.000 claims description 16
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 13
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- 125000001424 substituent group Chemical group 0.000 claims description 12
- 241000700626 Cowpox virus Species 0.000 claims description 10
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- 241000700627 Monkeypox virus Species 0.000 claims description 9
- 239000003443 antiviral agent Substances 0.000 claims description 9
- 229910052786 argon Inorganic materials 0.000 claims description 9
- 229940125904 compound 1 Drugs 0.000 claims description 9
- 241000282414 Homo sapiens Species 0.000 claims description 8
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- 241001137864 Camelpox virus Species 0.000 claims description 6
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- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- 150000003738 xylenes Chemical class 0.000 claims description 5
- 108060003951 Immunoglobulin Proteins 0.000 claims description 4
- 229940121357 antivirals Drugs 0.000 claims description 4
- 239000002552 dosage form Substances 0.000 claims description 4
- 102000018358 immunoglobulin Human genes 0.000 claims description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 4
- 229960003966 nicotinamide Drugs 0.000 claims description 4
- 239000011570 nicotinamide Substances 0.000 claims description 4
- 230000001681 protective effect Effects 0.000 claims description 4
- 241000725630 Ectromelia virus Species 0.000 claims description 3
- 230000002238 attenuated effect Effects 0.000 claims description 3
- 230000036039 immunity Effects 0.000 claims description 3
- 241000957224 BeAn 58058 virus Species 0.000 claims description 2
- 241001455646 Buffalopox virus Species 0.000 claims description 2
- 241000562578 Cantagalo virus Species 0.000 claims description 2
- 241000321599 Elephantpox virus Species 0.000 claims description 2
- 102000014150 Interferons Human genes 0.000 claims description 2
- 108010050904 Interferons Proteins 0.000 claims description 2
- 241001455645 Rabbitpox virus Species 0.000 claims description 2
- 241000700638 Raccoonpox virus Species 0.000 claims description 2
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 2
- 241000321597 Skunkpox virus Species 0.000 claims description 2
- 241001137863 Taterapox virus Species 0.000 claims description 2
- 241001137865 Volepox virus Species 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- 230000002924 anti-infective effect Effects 0.000 claims description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 2
- 229940088710 antibiotic agent Drugs 0.000 claims description 2
- 230000037396 body weight Effects 0.000 claims description 2
- CHVJITGCYZJHLR-UHFFFAOYSA-N cyclohepta-1,3,5-triene Chemical compound C1C=CC=CC=C1 CHVJITGCYZJHLR-UHFFFAOYSA-N 0.000 claims description 2
- 229940072221 immunoglobulins Drugs 0.000 claims description 2
- 239000002955 immunomodulating agent Substances 0.000 claims description 2
- 229940121354 immunomodulator Drugs 0.000 claims description 2
- 239000012678 infectious agent Substances 0.000 claims description 2
- 229940047124 interferons Drugs 0.000 claims description 2
- 229960000329 ribavirin Drugs 0.000 claims description 2
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 2
- CSKDFZIMJXRJGH-VWLPUNTISA-N tecovirimat Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)NN1C(=O)[C@@H]([C@@H]2[C@H]3C[C@H]3[C@H]3C=C2)[C@@H]3C1=O CSKDFZIMJXRJGH-VWLPUNTISA-N 0.000 claims 15
- QRWZSMGXNJSJBA-UHFFFAOYSA-N stk023504 Chemical compound C1=CC(Br)=CC=C1C(=O)NN1C(=O)C(C2C3CC3C3C=C2)C3C1=O QRWZSMGXNJSJBA-UHFFFAOYSA-N 0.000 claims 5
- KJDNIXCMYMBSNO-UHFFFAOYSA-N 4-bromo-n-(1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-2-yl)benzamide Chemical compound C1=CC(Br)=CC=C1C(=O)NN1C(=O)C2CCCCC2C1=O KJDNIXCMYMBSNO-UHFFFAOYSA-N 0.000 claims 4
- IVYPVGFVVJXQCM-UHFFFAOYSA-N N-(3,5-dioxo-4-azatetracyclo[5.3.2.02,6.08,10]dodec-11-en-4-yl)-3-fluorobenzamide Chemical compound FC1=CC=CC(C(=O)NN2C(C3C(C4C=CC3C3CC34)C2=O)=O)=C1 IVYPVGFVVJXQCM-UHFFFAOYSA-N 0.000 claims 4
- YIRDWOBUQUNSNY-UHFFFAOYSA-N N-(3,5-dioxo-4-azatetracyclo[5.3.2.02,6.08,10]dodec-11-en-4-yl)-4-fluorobenzamide Chemical compound C1=CC(F)=CC=C1C(=O)NN1C(=O)C(C2C3CC3C3C=C2)C3C1=O YIRDWOBUQUNSNY-UHFFFAOYSA-N 0.000 claims 4
- OLFJAAPWKAVFKS-UHFFFAOYSA-N 2-bromo-N-(3,5-dioxo-4-azatetracyclo[5.3.2.02,6.08,10]dodec-11-en-4-yl)benzamide Chemical compound BrC1=CC=CC=C1C(=O)NN1C(=O)C(C2C3CC3C3C=C2)C3C1=O OLFJAAPWKAVFKS-UHFFFAOYSA-N 0.000 claims 3
- NHMSINHXUXEFJT-UHFFFAOYSA-N 4-bromo-N-(3,5-dioxo-4-azatetracyclo[5.3.2.02,6.08,10]dodecan-4-yl)benzamide Chemical compound C1=CC(Br)=CC=C1C(=O)NN1C(=O)C(C2C3CC3C3CC2)C3C1=O NHMSINHXUXEFJT-UHFFFAOYSA-N 0.000 claims 3
- XIDCFAYBJPWRRW-UHFFFAOYSA-N 4-cyano-N-(3,5-dioxo-4-azatetracyclo[5.3.2.02,6.08,10]dodec-11-en-4-yl)benzamide Chemical compound O=C1C(C2C=CC3C4CC42)C3C(=O)N1NC(=O)C1=CC=C(C#N)C=C1 XIDCFAYBJPWRRW-UHFFFAOYSA-N 0.000 claims 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- 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
- A61P31/20—Antivirals for DNA viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48018203P | 2003-06-20 | 2003-06-20 | |
| US60/480,182 | 2003-06-20 | ||
| PCT/US2004/019552 WO2004112718A2 (en) | 2003-06-20 | 2004-06-18 | Compounds, compositions and methods for treatment and prevention of orthopoxvirus infections and associated diseases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2529761A1 CA2529761A1 (en) | 2004-12-29 |
| CA2529761C true CA2529761C (en) | 2013-08-13 |
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|---|---|---|---|
| CA2529761A Expired - Lifetime CA2529761C (en) | 2003-06-20 | 2004-06-18 | Compounds, compositions and methods for treatment and prevention of orthopoxvirus infections and associated diseases |
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| Country | Link |
|---|---|
| EP (1) | EP1638938B1 (enExample) |
| JP (2) | JP4884216B2 (enExample) |
| AU (1) | AU2004249250C1 (enExample) |
| BE (1) | BE2022C521I2 (enExample) |
| CA (1) | CA2529761C (enExample) |
| DK (1) | DK1638938T3 (enExample) |
| ES (1) | ES2632313T3 (enExample) |
| FR (1) | FR22C1022I1 (enExample) |
| NL (1) | NL301177I2 (enExample) |
| PL (1) | PL1638938T3 (enExample) |
| WO (1) | WO2004112718A2 (enExample) |
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| US8530509B2 (en) | 2003-06-20 | 2013-09-10 | Siga Technologies, Inc. | Compounds, compositions and methods for treatment and prevention of orthopoxvirus infections and associated diseases |
| AU2012268859B2 (en) * | 2003-06-20 | 2016-05-05 | Siga Technologies, Inc. | Chemicals, compositions, and methods for treatment and prevention of orthopoxvirus infections and associated diseases |
| US7737168B2 (en) | 2003-06-20 | 2010-06-15 | Siga Technologies, Inc. | Compounds, compositions, and methods for treatment and prevention of orthopoxvirus infections and associated diseases |
| PL1638938T3 (pl) * | 2003-06-20 | 2017-10-31 | Siga Tech Inc | Związki, kompozycje i sposoby do leczenia i zapobiegania infekcjom ortopokswirusami i powiązanym chorobom |
| AU2007351866C1 (en) * | 2003-06-20 | 2013-07-25 | Siga Technologies, Inc. | Chemicals, compositions, and methods for treatment and prevention of orthopoxvirus infections and associated diseases |
| MY141198A (en) * | 2004-08-30 | 2010-03-31 | Janssen Pharmaceutica Nv | Tricyclic adamantylamide derivatives as 11-beta hydroxysteroid dehydrogenase inhibitors |
| US8410149B2 (en) | 2004-12-06 | 2013-04-02 | Siga Technologies Inc. | Sulfonyl semicarbazides, semicarbazides and ureas, pharmaceutical compositions thereof, and methods for treating hemorrhagic fever viruses, including infections associated with arenaviruses |
| US7994221B2 (en) | 2004-12-06 | 2011-08-09 | Siga Technologies, Inc. | Sulfonyl semicarbazides, carbonyl semicarbazides, semicarbazides and ureas, pharmaceutical compositions thereof, and methods for treating hemorrhagic fever viruses, including infections associated with arenaviruses |
| WO2006062898A2 (en) | 2004-12-06 | 2006-06-15 | Siga Technologies, Inc. | Compounds and methods for treating hemorrhagic fever viruses |
| JP2008538354A (ja) * | 2005-04-08 | 2008-10-23 | キメリクス，インコーポレイテッド | ウイルス感染症およびその他の内科疾患を治療するための化合物、組成物および方法 |
| WO2006110655A2 (en) * | 2005-04-08 | 2006-10-19 | Chimerix, Inc. | Compounds, compositions and methods for the treatment of poxvirus infections |
| CN105055432A (zh) | 2008-01-25 | 2015-11-18 | 奇默里克斯公司 | 治疗病毒感染的方法 |
| US8614200B2 (en) | 2009-07-21 | 2013-12-24 | Chimerix, Inc. | Compounds, compositions and methods for treating ocular conditions |
| RU2412167C1 (ru) * | 2009-12-02 | 2011-02-20 | Федеральное государственное учреждение науки "Государственный научный центр вирусологии и биотехнологии "Вектор" Федеральной службы по надзору в сфере защиты прав потребителей и благополучия человека (ФГУН ГНЦ ВБ "Вектор" Роспотребнадзора) | {3,5-диоксо-4-азатетрацикло[5.3.2.02,6.08,10]додец-11-ен-4-ил}тиомочевина, обладающая противовирусной активностью в отношении ортопоксвирусов |
| RU2412168C1 (ru) * | 2009-12-02 | 2011-02-20 | Федеральное государственное учреждение науки "Государственный научный центр вирусологии и биотехнологии "Вектор" Федеральной службы по надзору в сфере защиты прав потребителей и благополучия человека (ФГУН ГНЦ ВБ "Вектор" Роспотребнадзора) | Гидрат n-{3,5-диоксо-4-азатетрацикло[5.3.2.02,6.08,10]додец-11-ен-4-ил}-2-гидроксибензамида, обладающий противовирусной активностью в отношении ортопоксвирусов |
| CA2789443C (en) | 2010-02-12 | 2016-09-13 | Chimerix, Inc. | Nucleoside phosphonate salts |
| PE20170944A1 (es) | 2010-03-23 | 2017-07-13 | Siga Tech Inc | Formas polimorficas de st-246 y metodos de preparacion |
| EP2563367A4 (en) | 2010-04-26 | 2013-12-04 | Chimerix Inc | Methods of treating retroviral infections and related dosage regimes |
| CN106074370A (zh) * | 2010-08-05 | 2016-11-09 | 西佳科技股份有限公司 | St‑246液体配制物以及方法 |
| CN101906064A (zh) * | 2010-08-09 | 2010-12-08 | 中国人民解放军军事医学科学院微生物流行病研究所 | St-246的立体异构体的制备方法 |
| RU2440983C1 (ru) * | 2010-09-28 | 2012-01-27 | Новосибирский институт органической химии им. Н.Н. Ворожцова Сибирского отделения Российской академии наук (НИОХ СО РАН) | Метил, хлор и нитропроизводные n-{3, 5-диоксо-4-азатетрацикло[5.3.2.02,6.08,10]додец-11-ен-4-ил}-2-гидроксибензамида-противовирусные препараты, ингибирующие репликацию различных видов ортопоксвирусов |
| CA3183432A1 (en) | 2012-08-16 | 2014-02-20 | Siga Technologies, Inc. | Methods of preparing tecovirimat |
| CN105307636A (zh) | 2013-07-19 | 2016-02-03 | 西佳技术公司 | 非晶形特考韦瑞制备 |
| WO2023192782A2 (en) * | 2022-03-27 | 2023-10-05 | Board Of Regents, The University Of Texas System | Small molecule inhibitors of lanosterol synthase |
| CN116730995B (zh) * | 2022-08-12 | 2024-06-25 | 深圳微芯生物科技股份有限公司 | 一类酰肼类化合物、其制备方法及其应用 |
| CN116003309B (zh) * | 2022-08-12 | 2025-03-04 | 深圳微芯生物科技股份有限公司 | 一类酰肼类化合物、其制备方法及其应用 |
| CN116836173B (zh) * | 2023-08-31 | 2023-12-12 | 甫康（上海）健康科技有限责任公司 | 亚胺酰基酰肼类化合物、含其的组合物和其应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2906755A (en) * | 1956-11-16 | 1959-09-29 | Schenley Ind Inc | N-acyl derivatives of alpha-pyridine carboxylic acid hydrazide |
| US4061763A (en) * | 1975-05-09 | 1977-12-06 | Merck & Co., Inc. | Tricyclicdicarboximides |
| JPS5247844A (en) * | 1975-10-15 | 1977-04-16 | Ube Ind Ltd | Elastomer compositions |
| JPS6483065A (en) * | 1987-09-25 | 1989-03-28 | Hitachi Chemical Co Ltd | Endo-cis-3,6-cyclopropylene-tetra(or hexa)hydrophthalic acid imide derivative and antiarhythmic agent |
| US5068356A (en) * | 1990-02-20 | 1991-11-26 | Atochem North America, Inc. | Hindered phenolic n-(amido)imides |
| US6596771B2 (en) | 2001-01-12 | 2003-07-22 | Schering Corporation | Drugs for treating viral infections |
| US6433016B1 (en) * | 2001-01-12 | 2002-08-13 | Vassil Stefanov Georgiev | Drugs for treating viral infections |
| US20040087548A1 (en) * | 2001-02-27 | 2004-05-06 | Salvati Mark E. | Fused cyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function |
| PL1638938T3 (pl) * | 2003-06-20 | 2017-10-31 | Siga Tech Inc | Związki, kompozycje i sposoby do leczenia i zapobiegania infekcjom ortopokswirusami i powiązanym chorobom |
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- 2004-06-18 PL PL04776765T patent/PL1638938T3/pl unknown
- 2004-06-18 WO PCT/US2004/019552 patent/WO2004112718A2/en not_active Ceased
- 2004-06-18 JP JP2006517409A patent/JP4884216B2/ja not_active Expired - Lifetime
- 2004-06-18 CA CA2529761A patent/CA2529761C/en not_active Expired - Lifetime
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- 2004-06-18 EP EP04776765.2A patent/EP1638938B1/en not_active Expired - Lifetime
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- 2004-06-18 AU AU2004249250A patent/AU2004249250C1/en not_active Expired
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2011
- 2011-08-18 JP JP2011179109A patent/JP5657489B2/ja not_active Expired - Lifetime
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2022
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- 2022-06-02 NL NL301177C patent/NL301177I2/nl unknown
- 2022-06-02 FR FR22C1022C patent/FR22C1022I1/fr active Active
Also Published As
| Publication number | Publication date |
|---|---|
| AU2004249250B2 (en) | 2011-09-01 |
| PL1638938T3 (pl) | 2017-10-31 |
| NL301177I1 (nl) | 2022-06-08 |
| BE2022C521I2 (enExample) | 2024-04-23 |
| FR22C1022I1 (fr) | 2022-07-22 |
| EP1638938B1 (en) | 2017-04-12 |
| NL301177I2 (nl) | 2022-08-23 |
| WO2004112718A3 (en) | 2005-04-07 |
| JP4884216B2 (ja) | 2012-02-29 |
| JP2007521273A (ja) | 2007-08-02 |
| CA2529761A1 (en) | 2004-12-29 |
| WO2004112718A2 (en) | 2004-12-29 |
| JP2011252019A (ja) | 2011-12-15 |
| EP1638938A2 (en) | 2006-03-29 |
| JP5657489B2 (ja) | 2015-01-21 |
| DK1638938T3 (en) | 2017-07-31 |
| AU2004249250A1 (en) | 2004-12-29 |
| AU2004249250C1 (en) | 2012-04-12 |
| ES2632313T3 (es) | 2017-09-12 |
| EP1638938A4 (en) | 2008-09-17 |
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