HRP20090675T1 - Postupak dobivanja međuprodukata epoksibutanola - Google Patents
Postupak dobivanja međuprodukata epoksibutanola Download PDFInfo
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- HRP20090675T1 HRP20090675T1 HR20090675T HRP20090675T HRP20090675T1 HR P20090675 T1 HRP20090675 T1 HR P20090675T1 HR 20090675 T HR20090675 T HR 20090675T HR P20090675 T HRP20090675 T HR P20090675T HR P20090675 T1 HRP20090675 T1 HR P20090675T1
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- 238000000034 method Methods 0.000 title claims abstract 23
- 239000000543 intermediate Substances 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 27
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 7
- 239000011737 fluorine Substances 0.000 claims abstract 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000001257 hydrogen Substances 0.000 claims abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract 4
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract 4
- -1 alkali metal nitrite Chemical class 0.000 claims abstract 4
- 239000000460 chlorine Substances 0.000 claims abstract 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 4
- 150000002148 esters Chemical class 0.000 claims abstract 4
- 239000002904 solvent Substances 0.000 claims abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 3
- 239000002253 acid Substances 0.000 claims abstract 3
- 150000003983 crown ethers Chemical class 0.000 claims abstract 3
- 230000000269 nucleophilic effect Effects 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 235000010289 potassium nitrite Nutrition 0.000 claims 3
- 239000004304 potassium nitrite Substances 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Substances [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims 3
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 235000010288 sodium nitrite Nutrition 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- QUGUFLJIAFISSW-UHFFFAOYSA-N 1,4-difluorobenzene Chemical compound FC1=CC=C(F)C=C1 QUGUFLJIAFISSW-UHFFFAOYSA-N 0.000 claims 1
- VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 claims 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical group C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 claims 1
- LJANCPRIUMHGJE-UHFFFAOYSA-N 4-(2-bromoacetyl)benzonitrile Chemical compound BrCC(=O)C1=CC=C(C#N)C=C1 LJANCPRIUMHGJE-UHFFFAOYSA-N 0.000 claims 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 238000006202 Sharpless epoxidation reaction Methods 0.000 claims 1
- UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- IRDLUHRVLVEUHA-UHFFFAOYSA-N diethyl dithiophosphate Chemical compound CCOP(S)(=S)OCC IRDLUHRVLVEUHA-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/336—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having three-membered rings, e.g. oxirane, fumagillin
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrane Compounds (AREA)
Abstract
Postupak dobivanja spoja formule (I) ,u kojojHal predstavlja fluor ili klor, aR1 i R2, međusobno neovisno, predstavljaju vodik ili jedno od značenja Hal; naznačen time što u navedenom postupku spoj formule (II) se prevodi u odgovarajući ester alkil-, fluoralkil- ili arilsulfonske kiseline, koji zatim reagira s nitritom alkalnog metala, u prisutnosti pogodnog krunastog etera, u polarnom nenukleofilnom otapalu, na temperaturi od -10 °C do 50 °C, kako bi se dobilo spoj formule (I). Patent sadrži još 16 patentnih zahtjeva.
Claims (17)
1. Postupak dobivanja spoja formule (I)
[image]
,
u kojoj
Hal predstavlja fluor ili klor, a
R1 i R2, međusobno neovisno, predstavljaju vodik ili jedno od značenja Hal;
naznačen time što u navedenom postupku spoj formule (II)
[image]
se prevodi u odgovarajući ester alkil-, fluoralkil- ili arilsulfonske kiseline, koji zatim reagira s nitritom alkalnog metala, u prisutnosti pogodnog krunastog etera, u polarnom nenukleofilnom otapalu, na temperaturi od –10 °C do 50 °C, kako bi se dobilo spoj formule (I).
2. Postupak u skladu s patentnim zahtjevom 1, naznačen time što navedeni ester alkil- ili arilsulfonske kiseline je ester trifluormetilsulfonske kiseline.
3. Postupak u skladu s patentnim zahtjevom 1 ili 2, naznačen time što nitrit alkalnog metala je natrijev ili kalijev nitrit.
4. Postupak u skladu s bilo kojim patentnim zahtjevom od 1 do 3, naznačen time što krunasti eter je 18-kruna-6-eter u slučaju upotrebe kalijevog nitrita, a 15-kruna-5-eter u slučaju upotrebe natrijevog nitrita.
5. Postupak u skladu s patentnim zahtjevom 3 ili 4, naznačen time što nitrit alkalnog metala je kalijev nitrit.
6. Postupak u skladu s bilo kojim patentnim zahtjevom od 1 do 5, naznačen time što otapalo, koje se bira između dimetil-sulfoksida (DMSO), 1,3-dimetil-3,4,5,6-tetrahidro-2(1H)-pirimidinona (DMPU), tetrahidrfurana (TFU), dioksana, formamida i njihovih smjesa, se upotrebljava kao polarno nenukleofilno otapalo.
7. Postupak u skladu s bilo kojim patentnim zahtjevom od 1 do 6, naznačen time što Hal predstavlja fluor u formuli (I) i jedan od R1 i R2 predstavlja vodik, a drugi fluor.
8. Postupak u skladu s patentnim zahtjevom 7, naznačen time što R1 predstavlja fluor, a R2 predstavlja vodik.
9. Postupak u skladu s patentnim zahtjevom 8, naznačen time što spoj formule (II) se dobiva postupkom koji uključuje reakciju 1,4-difluorbenzena sa spojem formule (III)
[image]
,
gdje
PrG predstavlja zaštitnu skupinu za hidroksil,
R3 predstavlja metil ili etil, i
R4 predstavlja metil, etil ili metoksi, ili
R3 i R4, uzeti zajedno s atomom dušika na kojeg su vezani, predstavljaju 4- do 6- članu heterocikličku skupinu, koja bilo ne sadrži niti jedan ili sadrži jedan ili dva dodatna heteroatoma, koje se bira između dušika ili kisika;
u prisutnosti baze, kako bi se dobilo spoj formule (IV)
[image]
,
gdje PrG ima isto značenje kao u formuli (III).
10. Postupak u skladu s bilo kojim patentnim zahtjevom od 1 do 8, naznačen time što spoj formule (V)
[image]
,
gdje
Hal predstavlja fluor ili klor,
X predstavlja jod ili brom, a
R1 i R2, međusobno neovisno, predstavljaju vodik, fluor ili klor;
najprije reagira s magnezijem, a dobiveni produkt reagira sa spojem formule (III)
[image]
,
gdje
PrG predstavlja zaštitnu skupinu za hidroksil,
R3 predstavlja metil ili etil, a
R4 predstavlja metil, etil ili metoksi, ili
R3 i R4, uzeti zajedno s atomom dušika na kojeg su vezani, predstavljaju 4- do 6- članu heterocikličku skupinu, koja bilo ne sadrži niti jedan ili sadrži jedan ili dva dodatna heteroatoma, koje se bira između dušika ili kisika;
kako bi se dobilo spoj formule (VI)
[image]
,
gdje
PrG ima isto značenje kao u formuli (III), a
R1 i R2 imaju isto značenje kao u formuli (V).
11. Postupak u skladu s patentnim zahtjevom 9 ili 10, naznačen time što R3 i R4, uzeti zajedno s atomom dušika na kojeg su vezani, predstavljaju morfolin-4-ilni ostatak.
12. Postupak u skladu s bilo kojim patentnim zahtjevom od 1 do 11, naznačen time što spoj formule (VI)
[image]
,
gdje
Hal, R1 i R2 imaju isto značenje kao u formuli (VI), a
R6 predstavlja PrG ili vodik.
13. Postupak u skladu s patentnim zahtjevom 12, naznačen time što sa spoja formule (VII) se uklanja zaštita, gdje R6 predstavlja zaštitnu skupinu za hidroksil, i/ili ga se Sharplessovim epoksidiranjem prevodi u spoj formule (II):
[image]
,
gdje
Hal, R1 i R2 imaju isto značenje kao u formuli (VI).
14. Postupak u skladu s bilo kojim patentnim zahtjevom od 1 do 13, naznačen time što spoj formule (I), kao što je prikazan u patentnom zahtjevu 1, reagira s 1,2,4-triazolom, u prisutnosti baze, kako bi se dobilo spoj formule (VIII)
[image]
gdje Hal, R1 i R2 imaju isto značenje kao u formuli (I),
gdje se navedeni spoj zatim prevodi u spoj formule (IX):
[image]
gdje Hal, R1 i R2 imaju isto značenje kao u formuli (I).
15. Postupak u skladu s patentnim zahtjevom 14, naznačen time što spoj formule (IX) se prevodi u spoj formule (X)
[image]
gdje Hal, R1 i R2 imaju isto značenje kao u formuli (IX), gdje navedeni spoj formule (X) reagira s O,O-dietilnim esterom ditiofosforne kiseline ili amonijevim sulfidom kako bi se dobilo spoj formule (XI):
[image]
gdje Hal, R1 i R2 imaju isto značenje kao u formuli (X), a navedeni spoj formule (XI) dalje reagira s 2-brom-4'-cijanoacetofenonom kako bi se dobilo spoj formule (XII):
[image]
gdje Hal, R1 i R2 imaju isto značenje kao u formuli (XI).
16. Postupak u skladu s patentnim zahtjevom 15, naznačen time što je namijenjen dobivanju spoja formule (XII-a)
[image]
17. Upotreba postupka u skladu s bilo kojim patentnim zahtjevom od 1 do 16, naznačena time što je navedeni postupak namijenjen dobivanju spoja formule (XII-a)
[image]
njegove farmaceutski prihvatljive soli, hidrata ili solvata.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05026163 | 2005-12-01 | ||
| PCT/CH2006/000671 WO2007062542A2 (en) | 2005-12-01 | 2006-11-29 | Process for the manufacture of epoxybutanol intermediates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20090675T1 true HRP20090675T1 (hr) | 2010-01-31 |
Family
ID=36178579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20090675T HRP20090675T1 (hr) | 2005-12-01 | 2009-12-17 | Postupak dobivanja međuprodukata epoksibutanola |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US7816537B2 (hr) |
| EP (2) | EP1954264B1 (hr) |
| JP (1) | JP5329969B2 (hr) |
| KR (1) | KR101191682B1 (hr) |
| CN (1) | CN101321522B (hr) |
| AT (1) | ATE444747T1 (hr) |
| AU (2) | AU2006319657B2 (hr) |
| BR (1) | BRPI0619120B1 (hr) |
| CA (2) | CA2711852C (hr) |
| CY (1) | CY1110588T1 (hr) |
| DE (1) | DE602006009698D1 (hr) |
| DK (1) | DK1954264T3 (hr) |
| ES (1) | ES2333258T3 (hr) |
| HR (1) | HRP20090675T1 (hr) |
| PL (1) | PL1954264T3 (hr) |
| PT (1) | PT1954264E (hr) |
| SI (1) | SI1954264T1 (hr) |
| WO (1) | WO2007062542A2 (hr) |
| ZA (1) | ZA200804218B (hr) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT2480559E (pt) | 2009-09-21 | 2013-10-02 | Gilead Sciences Inc | Processos e intermediários para a preparação de análogos de 1'-ciano-carbanucleósido |
| UA111163C2 (uk) | 2010-07-22 | 2016-04-11 | Гайлід Сайєнсіз, Інк. | Способи й сполуки для лікування вірусних інфекцій paramyxoviridae |
| SI2882723T1 (sl) | 2012-08-07 | 2017-04-26 | Basilea Pharmaceutica Ag | Postopek izdelave izavukonazola ali ravukonazola |
| WO2015150947A1 (en) | 2014-03-29 | 2015-10-08 | Wockhardt Limited | A process for the preparation of isavuconazole and its intermediates |
| TWI740546B (zh) | 2014-10-29 | 2021-09-21 | 美商基利科學股份有限公司 | 製備核糖苷的方法 |
| EP3785717B1 (en) | 2015-09-16 | 2022-01-05 | Gilead Sciences, Inc. | Methods for treating coronaviridae infections |
| CN105367528A (zh) * | 2015-11-10 | 2016-03-02 | 南通诺泰生物医药技术有限公司 | 一种三唑类药物中间体(d)-1-(1-环烷仲胺基)-2-(2-四氢吡喃基)氧-1-丙酮类化合物及合成方法 |
| ES2961460T3 (es) | 2017-03-14 | 2024-03-12 | Gilead Sciences Inc | Métodos para tratar las infecciones por coronavirus felinas |
| WO2018204198A1 (en) | 2017-05-01 | 2018-11-08 | Gilead Sciences, Inc. | Crystalline forms of (s) 2 ethylbutyl 2 (((s) (((2r,3s,4r,5r) 5 (4 aminopyrrolo[2,1-f] [1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2 yl)methoxy)(phenoxy) phosphoryl)amino)propanoate |
| US10675296B2 (en) | 2017-07-11 | 2020-06-09 | Gilead Sciences, Inc. | Compositions comprising an RNA polymerase inhibitor and cyclodextrin for treating viral infections |
| ES2915582T3 (es) | 2017-08-10 | 2022-06-23 | Sumitomo Chemical Co | Método para producir un compuesto de alcohol epoxi |
| US11660307B2 (en) | 2020-01-27 | 2023-05-30 | Gilead Sciences, Inc. | Methods for treating SARS CoV-2 infections |
| WO2021183750A2 (en) | 2020-03-12 | 2021-09-16 | Gilead Sciences, Inc. | Methods of preparing 1'-cyano nucleosides |
| WO2021207049A1 (en) | 2020-04-06 | 2021-10-14 | Gilead Sciences, Inc. | Inhalation formulations of 1'-cyano substituted carbanucleoside analogs |
| EP4157272A1 (en) | 2020-05-29 | 2023-04-05 | Gilead Sciences, Inc. | Remdesivir treatment methods |
| MX2022016405A (es) | 2020-06-24 | 2023-01-30 | Gilead Sciences Inc | Análogos de nucleósido de 1¿-ciano y usos de estos. |
| JP2023540225A (ja) | 2020-08-27 | 2023-09-22 | ギリアード サイエンシーズ， インコーポレイテッド | ウイルス感染症の治療のための化合物及び方法 |
| TW202400185A (zh) | 2022-03-02 | 2024-01-01 | 美商基利科學股份有限公司 | 用於治療病毒感染的化合物及方法 |
| CN115536643A (zh) * | 2022-12-05 | 2022-12-30 | 南京桦冠生物技术有限公司 | 一种艾沙康唑类药物关键中间体的制备方法 |
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| JP3452213B2 (ja) * | 1994-07-05 | 2003-09-29 | エーザイ株式会社 | 抗真菌剤及びその製造方法 |
| WO1999045008A1 (en) * | 1998-03-06 | 1999-09-10 | F. Hoffmann-La Roche Ag | 3-[4-(4-cyanophenyl)thiazol-2-y)]-1-(1h-1,2,4-triazol-1-yl)-butan-2-ol derivatives having antifungal activity |
| US6133485A (en) | 1998-04-15 | 2000-10-17 | Synphar Laboratories, Inc. | Asymmetric synthesis of 2-(2,4-difluorophenyl)-1-heterocycl-1-yl butan-2,3-diols |
| US6391903B1 (en) | 1999-09-09 | 2002-05-21 | Sankyo Company, Limited | Triazole derivatives having antifungal activity |
| US6884892B2 (en) | 2002-06-20 | 2005-04-26 | Sumitomo Chemical Company, Limited | Production methods of epoxytriazole derivative and intermediate therefor |
| JP4627413B2 (ja) * | 2003-05-06 | 2011-02-09 | 三井化学株式会社 | １−アゾール−２−フェニル−２、３−プロパンジオール誘導体の製造法 |
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