TW201609752A - 抗病毒化合物之晶形 - Google Patents
抗病毒化合物之晶形 Download PDFInfo
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- TW201609752A TW201609752A TW103144805A TW103144805A TW201609752A TW 201609752 A TW201609752 A TW 201609752A TW 103144805 A TW103144805 A TW 103144805A TW 103144805 A TW103144805 A TW 103144805A TW 201609752 A TW201609752 A TW 201609752A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 815
- 230000000840 anti-viral effect Effects 0.000 title description 2
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 120
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- VNXBKJFUJUWOCW-UHFFFAOYSA-N methylcyclopropane Chemical compound CC1CC1 VNXBKJFUJUWOCW-UHFFFAOYSA-N 0.000 claims description 112
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 106
- 230000005855 radiation Effects 0.000 claims description 95
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 82
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- 238000001179 sorption measurement Methods 0.000 claims description 80
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- 238000001757 thermogravimetry curve Methods 0.000 claims description 63
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- 238000005481 NMR spectroscopy Methods 0.000 claims description 52
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 48
- 239000012453 solvate Substances 0.000 claims description 47
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 44
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 32
- 241000711549 Hepacivirus C Species 0.000 claims description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 19
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- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
- CCZHABWIXLIPJP-UHFFFAOYSA-N 3h-dioxadiazole Chemical compound N1OOC=N1 CCZHABWIXLIPJP-UHFFFAOYSA-N 0.000 claims 1
- 229940125904 compound 1 Drugs 0.000 claims 1
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- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract description 22
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 100
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- 125000000392 cycloalkenyl group Chemical group 0.000 description 16
- FYZZJDABXBPMOG-UHFFFAOYSA-N ethanol;n-methylmethanamine Chemical compound CCO.CNC FYZZJDABXBPMOG-UHFFFAOYSA-N 0.000 description 16
- 239000000725 suspension Substances 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
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- 108010050904 Interferons Proteins 0.000 description 12
- 102000014150 Interferons Human genes 0.000 description 12
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 12
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 12
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- 150000003248 quinolines Chemical group 0.000 description 11
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- FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 description 10
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
- RMIAZGFKBPOZLX-NLRFIBDTSA-N 4-methylbenzenesulfonic acid methyl (2S,3S,4R)-3-ethyl-4-hydroxypyrrolidine-2-carboxylate Chemical compound Cc1ccc(cc1)S(O)(=O)=O.CC[C@@H]1[C@@H](O)CN[C@@H]1C(=O)OC RMIAZGFKBPOZLX-NLRFIBDTSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 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 description 9
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- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 7
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- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000011991 zhan catalyst Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/16—Peri-condensed systems
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0808—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Gastroenterology & Hepatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361920427P | 2013-12-23 | 2013-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW201609752A true TW201609752A (zh) | 2016-03-16 |
Family
ID=52282995
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW103144805A TW201609752A (zh) | 2013-12-23 | 2014-12-22 | 抗病毒化合物之晶形 |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US9562058B2 (enExample) |
| EP (1) | EP3087086B1 (enExample) |
| JP (2) | JP6568541B2 (enExample) |
| AR (1) | AR098958A1 (enExample) |
| AU (1) | AU2014370124A1 (enExample) |
| CA (1) | CA2934049A1 (enExample) |
| ES (1) | ES2708993T3 (enExample) |
| NZ (1) | NZ720887A (enExample) |
| PT (1) | PT3087086T (enExample) |
| TW (1) | TW201609752A (enExample) |
| UY (1) | UY35918A (enExample) |
| WO (1) | WO2015100144A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9440991B2 (en) | 2013-12-23 | 2016-09-13 | Gilead Sciences, Inc. | Synthesis of an antiviral compound |
| CN118286245A (zh) | 2014-12-26 | 2024-07-05 | 埃莫里大学 | N4-羟基胞苷和衍生物及与其相关的抗病毒用途 |
| BR102017011025A2 (pt) | 2016-06-02 | 2017-12-19 | Gilead Pharmasset Llc | Formulation of combination of three antiviral compounds |
| RS66222B1 (sr) | 2017-12-07 | 2024-12-31 | Univ Emory | N4-hidroksicitidin i derivati i antivirusne upotrebe povezane sa njim |
| CN115417803B (zh) * | 2022-08-30 | 2023-10-03 | 四川同晟生物医药有限公司 | 乌帕替尼中间体(3r,4s)-1-苄氧羰基-4-乙基吡咯烷-3-羧酸的合成方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5023252A (en) | 1985-12-04 | 1991-06-11 | Conrex Pharmaceutical Corporation | Transdermal and trans-membrane delivery of drugs |
| US4992445A (en) | 1987-06-12 | 1991-02-12 | American Cyanamid Co. | Transdermal delivery of pharmaceuticals |
| US5001139A (en) | 1987-06-12 | 1991-03-19 | American Cyanamid Company | Enchancers for the transdermal flux of nivadipine |
| CL2008003384A1 (es) * | 2007-11-14 | 2009-12-11 | Enanta Pharm Inc | Compuestos derivados de quinoxalina macrocíclica, inhibidores de serina proteasa; composicion farmaceutica que los comprende; y su uso en el tratamiento de la hepatitis c. |
| SI2310095T1 (sl) * | 2008-07-22 | 2013-01-31 | Merck Sharp & Dohme Corp. | Makrocikliäśne kuinoksalinske spojine kot hcv ns3 proteazni inhibitorji |
| DK2618831T3 (en) * | 2010-09-21 | 2016-04-04 | Enanta Pharm Inc | Macrocyclic prolinafledte HCV serine protease inhibitors |
| US20130178413A1 (en) * | 2010-09-21 | 2013-07-11 | John A. McCauley | Hcv ns3 protease inhibitors |
| UA110354C2 (uk) | 2011-11-16 | 2015-12-25 | Гайлід Фармассет Елелсі | Противірусні сполуки |
| UA119315C2 (uk) | 2012-07-03 | 2019-06-10 | Гіліад Фармассет Елелсі | Інгібітори вірусу гепатиту с |
-
2014
- 2014-12-18 WO PCT/US2014/071310 patent/WO2015100144A1/en not_active Ceased
- 2014-12-18 ES ES14824322T patent/ES2708993T3/es active Active
- 2014-12-18 US US14/575,966 patent/US9562058B2/en active Active
- 2014-12-18 EP EP14824322.3A patent/EP3087086B1/en active Active
- 2014-12-18 CA CA2934049A patent/CA2934049A1/en not_active Abandoned
- 2014-12-18 PT PT14824322T patent/PT3087086T/pt unknown
- 2014-12-18 JP JP2016560857A patent/JP6568541B2/ja not_active Expired - Fee Related
- 2014-12-18 AU AU2014370124A patent/AU2014370124A1/en not_active Abandoned
- 2014-12-18 NZ NZ720887A patent/NZ720887A/en not_active IP Right Cessation
- 2014-12-22 TW TW103144805A patent/TW201609752A/zh unknown
- 2014-12-23 UY UY0001035918A patent/UY35918A/es not_active Application Discontinuation
- 2014-12-23 AR ARP140104909A patent/AR098958A1/es unknown
-
2016
- 2016-12-21 US US15/387,318 patent/US9862728B2/en active Active
-
2019
- 2019-02-07 JP JP2019020540A patent/JP2019089819A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU2014370124A1 (en) | 2016-06-23 |
| NZ720887A (en) | 2018-01-26 |
| EP3087086B1 (en) | 2018-11-07 |
| ES2708993T3 (es) | 2019-04-12 |
| JP2017503016A (ja) | 2017-01-26 |
| WO2015100144A1 (en) | 2015-07-02 |
| CA2934049A1 (en) | 2015-07-02 |
| AR098958A1 (es) | 2016-06-22 |
| EP3087086A1 (en) | 2016-11-02 |
| JP2019089819A (ja) | 2019-06-13 |
| PT3087086T (pt) | 2019-02-06 |
| US20150175625A1 (en) | 2015-06-25 |
| US20170267694A1 (en) | 2017-09-21 |
| UY35918A (es) | 2015-05-29 |
| US9562058B2 (en) | 2017-02-07 |
| JP6568541B2 (ja) | 2019-08-28 |
| US9862728B2 (en) | 2018-01-09 |
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