JP2013515746A - フラビウイルス感染症の治療又は予防のための類似体 - Google Patents
フラビウイルス感染症の治療又は予防のための類似体 Download PDFInfo
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- JP2013515746A JP2013515746A JP2012546254A JP2012546254A JP2013515746A JP 2013515746 A JP2013515746 A JP 2013515746A JP 2012546254 A JP2012546254 A JP 2012546254A JP 2012546254 A JP2012546254 A JP 2012546254A JP 2013515746 A JP2013515746 A JP 2013515746A
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- 206010054261 Flavivirus infection Diseases 0.000 title description 18
- 230000002265 prevention Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 501
- 229910052796 boron Inorganic materials 0.000 claims abstract description 89
- 150000003839 salts Chemical class 0.000 claims abstract description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 309
- -1 di-fluoromethyl Chemical group 0.000 claims description 215
- 125000000623 heterocyclic group Chemical group 0.000 claims description 208
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 155
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 151
- 125000003342 alkenyl group Chemical group 0.000 claims description 149
- 229910052799 carbon Inorganic materials 0.000 claims description 148
- 125000003118 aryl group Chemical group 0.000 claims description 147
- 125000001072 heteroaryl group Chemical group 0.000 claims description 141
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 137
- 229910052736 halogen Inorganic materials 0.000 claims description 133
- 150000002367 halogens Chemical class 0.000 claims description 133
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 131
- 125000000304 alkynyl group Chemical group 0.000 claims description 128
- 229910052739 hydrogen Inorganic materials 0.000 claims description 127
- 238000000034 method Methods 0.000 claims description 114
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 112
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 100
- 239000000203 mixture Substances 0.000 claims description 97
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 90
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 90
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 76
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 68
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 63
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 61
- 238000006243 chemical reaction Methods 0.000 claims description 58
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 55
- 125000004429 atom Chemical group 0.000 claims description 52
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 51
- 239000003795 chemical substances by application Substances 0.000 claims description 50
- DYMRYCZRMAHYKE-UHFFFAOYSA-N n-diazonitramide Chemical compound [O-][N+](=O)N=[N+]=[N-] DYMRYCZRMAHYKE-UHFFFAOYSA-N 0.000 claims description 46
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 43
- 230000003612 virological effect Effects 0.000 claims description 43
- 125000003545 alkoxy group Chemical group 0.000 claims description 40
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 38
- 229910052757 nitrogen Inorganic materials 0.000 claims description 36
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 35
- 239000003112 inhibitor Substances 0.000 claims description 29
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 230000008569 process Effects 0.000 claims description 26
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
- 230000008878 coupling Effects 0.000 claims description 25
- 238000010168 coupling process Methods 0.000 claims description 25
- 238000005859 coupling reaction Methods 0.000 claims description 25
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 24
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 23
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 20
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 19
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 239000003001 serine protease inhibitor Substances 0.000 claims description 16
- 239000007821 HATU Substances 0.000 claims description 15
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 15
- 125000002346 iodo group Chemical group I* 0.000 claims description 15
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
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- 101710102218 Serine protease inhibitor Proteins 0.000 claims description 14
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
- 229940123066 Polymerase inhibitor Drugs 0.000 claims description 13
- 229940121759 Helicase inhibitor Drugs 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical group 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 12
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 claims description 12
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 12
- 239000002955 immunomodulating agent Substances 0.000 claims description 12
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- 229960000329 ribavirin Drugs 0.000 claims description 12
- 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 12
- 238000010898 silica gel chromatography Methods 0.000 claims description 12
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 12
- 102000035195 Peptidases Human genes 0.000 claims description 11
- 108091005804 Peptidases Proteins 0.000 claims description 11
- 239000004365 Protease Substances 0.000 claims description 11
- 230000000692 anti-sense effect Effects 0.000 claims description 11
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
- 239000003937 drug carrier Substances 0.000 claims description 11
- CEFVHPDFGLDQKU-YFKPBYRVSA-N (2s)-2-(methoxycarbonylamino)-3-methylbutanoic acid Chemical compound COC(=O)N[C@@H](C(C)C)C(O)=O CEFVHPDFGLDQKU-YFKPBYRVSA-N 0.000 claims description 10
- 239000003242 anti bacterial agent Substances 0.000 claims description 10
- 239000003963 antioxidant agent Substances 0.000 claims description 10
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 229940021747 therapeutic vaccine Drugs 0.000 claims description 10
- 229930192474 thiophene Natural products 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 230000003078 antioxidant effect Effects 0.000 claims description 9
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 claims description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- 230000002584 immunomodulator Effects 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- 125000004193 piperazinyl group Chemical group 0.000 claims description 9
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 108010047761 Interferon-alpha Proteins 0.000 claims description 8
- 102000006992 Interferon-alpha Human genes 0.000 claims description 8
- 150000001350 alkyl halides Chemical class 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- 125000004587 thienothienyl group Chemical group S1C(=CC2=C1C=CS2)* 0.000 claims description 8
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 7
- 208000010710 hepatitis C virus infection Diseases 0.000 claims description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- 238000010511 deprotection reaction Methods 0.000 claims description 6
- 230000002140 halogenating effect Effects 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 6
- 230000001590 oxidative effect Effects 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
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- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 5
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 229910000085 borane Inorganic materials 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
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- 239000002445 liver protective agent Substances 0.000 claims description 5
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
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- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
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- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
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- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 claims description 4
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- CAOPPQCRTPFFGU-UHFFFAOYSA-N trimethyl-[2-[6-(2-trimethylsilylethynyl)naphthalen-2-yl]ethynyl]silane Chemical compound C1=C(C#C[Si](C)(C)C)C=CC2=CC(C#C[Si](C)(C)C)=CC=C21 CAOPPQCRTPFFGU-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
-
- 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
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- 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
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- 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
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
-
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Molecular Biology (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (5)
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| US61/316,998 | 2010-03-24 | ||
| PCT/US2010/062168 WO2011079327A1 (en) | 2009-12-24 | 2010-12-27 | Analogues for the treatment or prevention of flavivirus infections |
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| JP2013515746A true JP2013515746A (ja) | 2013-05-09 |
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| EP (1) | EP2515902A1 (enExample) |
| JP (1) | JP2013515746A (enExample) |
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| AU (1) | AU2010336355A1 (enExample) |
| CA (1) | CA2784036A1 (enExample) |
| IL (1) | IL220215A0 (enExample) |
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| SG (1) | SG181614A1 (enExample) |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017521484A (ja) * | 2014-06-06 | 2017-08-03 | 愛博新薬研発（上海）有限公司 | Ｃ型肝炎を抑制する化合物、医薬組成物及びそれらの応用 |
| JP2020529414A (ja) * | 2017-08-02 | 2020-10-08 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | ピロリジン化合物を調製するためのプロセス |
| WO2022270628A1 (ja) * | 2021-06-25 | 2022-12-29 | 国立大学法人 大分大学 | Ｒｓウイルス感染症の処置および／または予防用医薬としてのヘテロシクロアルキル置換ポリヘテロアゾール誘導体 |
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| CN102264737A (zh) | 2008-12-23 | 2011-11-30 | 雅培制药有限公司 | 抗病毒化合物 |
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| WO2010120935A1 (en) | 2009-04-15 | 2010-10-21 | Abbott Laboratories | Anti-viral compounds |
| SG176015A1 (en) | 2009-05-13 | 2011-12-29 | Gilead Sciences Inc | Antiviral compounds |
| US8211928B2 (en) | 2009-05-29 | 2012-07-03 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8138215B2 (en) | 2009-05-29 | 2012-03-20 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US9394279B2 (en) | 2009-06-11 | 2016-07-19 | Abbvie Inc. | Anti-viral compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2017521484A (ja) * | 2014-06-06 | 2017-08-03 | 愛博新薬研発（上海）有限公司 | Ｃ型肝炎を抑制する化合物、医薬組成物及びそれらの応用 |
| JP2020529414A (ja) * | 2017-08-02 | 2020-10-08 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | ピロリジン化合物を調製するためのプロセス |
| JP7121794B2 (ja) | 2017-08-02 | 2022-08-18 | バーテックス ファーマシューティカルズ インコーポレイテッド | ピロリジン化合物を調製するためのプロセス |
| WO2022270628A1 (ja) * | 2021-06-25 | 2022-12-29 | 国立大学法人 大分大学 | Ｒｓウイルス感染症の処置および／または予防用医薬としてのヘテロシクロアルキル置換ポリヘテロアゾール誘導体 |
| CN117730079A (zh) * | 2021-06-25 | 2024-03-19 | 亚博思生物科技(第一)有限公司 | 作为rsv感染症的治疗及/或预防用医药的经杂环烷基取代的聚杂唑衍生物 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102883718A (zh) | 2013-01-16 |
| CA2784036A1 (en) | 2011-06-30 |
| SG181614A1 (en) | 2012-07-30 |
| EP2515902A1 (en) | 2012-10-31 |
| US20130072523A1 (en) | 2013-03-21 |
| MX2012007420A (es) | 2012-07-23 |
| IL220215A0 (en) | 2012-07-31 |
| AU2010336355A1 (en) | 2012-07-05 |
| ZA201204625B (en) | 2014-06-25 |
| KR20120130173A (ko) | 2012-11-29 |
| WO2011079327A1 (en) | 2011-06-30 |
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