HRP20211154T1 - Postupak za pripravu derivata benzil-benzena supstituiranih glukopiranozilom - Google Patents
Postupak za pripravu derivata benzil-benzena supstituiranih glukopiranozilom Download PDFInfo
- Publication number
- HRP20211154T1 HRP20211154T1 HRP20211154TT HRP20211154T HRP20211154T1 HR P20211154 T1 HRP20211154 T1 HR P20211154T1 HR P20211154T T HRP20211154T T HR P20211154TT HR P20211154 T HRP20211154 T HR P20211154T HR P20211154 T1 HRP20211154 T1 HR P20211154T1
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- compound
- magnesium
- general formula
- subspecies
- Prior art date
Links
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 12
- 238000000034 method Methods 0.000 claims 12
- 229910052749 magnesium Inorganic materials 0.000 claims 7
- 239000011777 magnesium Substances 0.000 claims 7
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 5
- 239000000463 material Substances 0.000 claims 5
- 239000011541 reaction mixture Substances 0.000 claims 5
- -1 C1-4-alkyl magnesium chloride Chemical compound 0.000 claims 4
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 229910001448 ferrous ion Inorganic materials 0.000 claims 4
- 229910052742 iron Inorganic materials 0.000 claims 4
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 238000002386 leaching Methods 0.000 claims 2
- 229910001623 magnesium bromide Inorganic materials 0.000 claims 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims 2
- 229910001629 magnesium chloride Inorganic materials 0.000 claims 2
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 229910001092 metal group alloy Inorganic materials 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 150000002902 organometallic compounds Chemical class 0.000 claims 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/04—Carbocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (11)
1. Postupak za pripravljanje spoja opće formule III,
[image]
s time, da R1 označava (R)-tetrahidrofuran-3-il ili (S)-tetrahidrofuran-3-il; i
pritom R2 neovisno jedan od drugoga, označavaju vodik, (C18-alkil)karbonil, (C18-alkil)oksikarbonil, fenilkarbonil, fenil-(C1-3-alkil)-karbonil, fenil-C1-3-alkil, alil, RaRbRcSi, CRaRbORc, pri čemu dvije susjedne skupine R2 mogu biti povezane jedna s drugom da tvore premosnu skupinu SiRaRb, CRaRb ili CRaORb-CRaORb;
gdje Ra,Rb,Rc neovisno jedan od drugoga označavaju C1-4-alkil, fenil ili fenil-C1-3-alkil, dok alkilne skupine mogu biti mono- ili polisupstituirane s halogenom;
dok pritom fenilne skupine koje su spomenute u definiciji gore navedenih skupina, mogu biti mono- ili polisupstituirane s L1, pri čemu se L1 međusobno neovisno biraju od fluora, klora, broma, C1-3-alkila, C1-4-alkoksi i nitro; i
pritom R’ označava vodik, metil ili etil;
naznačen time, da obuhvaća korake (S1), (S2) i (S3):
(S1): reakciju spoja opće formule I
[image]
gdje je R1 definiran kao što je prethodno ovdje navedeno i X označava Br, I ili triflat;
s C1-4-alkil-magnezijevim kloridom ili bromidom,
pri čemu se litijev bromid i/ili litijev klorid koristi prema potrebi, i
(S2): reakciju organometalnog spoja koji se dobiva u koraku (S1) sa spojem opće formule II
[image]
gdje je R2 kao što je prethodno ovdje definiran; i
pritom se litijev bromid i/ili litijev klorid koriste prema potrebi, i
gdje se R2 koji nisu vodik, opcionalno cijepaju za vrijeme ili na kraju koraka (S2), i
(S3): reakciju privučenog proizvoda dobivenog u koraku (S2) sa spojem R'-OH ili mješavinom spojeva R'-OH, pri čemu je R' kao što je prethodno ovdje definiran, u prisutnosti jedne ili više kiselina,
naznačen time, da
molarni omjer željeznih iona u reakcijskim smjesama iz koraka (S1) i/ili (S2) prema spoju I koji je angažiran u koraku (S1), ne prelazi 40 ppm.
2. Postupak u skladu s patentnim zahtjevom 1, naznačen time, da X u koraku (S1) označava I.
3. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 ili 2, naznačen time, da se C3-4-alkil-magnezijev klorid ili bromid, poželjno izopropil magnezijev klorid angažira u koraku (S1) i dodatno se koristi litijev klorid u koraku (S1).
4. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačen time, da R2 označava trimetilsilil u spoju opće formule II koji se koristi u koraku (S2).
5. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačen time, da R’ u koraku (S3) označava metil.
6. Postupak za pripravljanje spoja opće formule IV
[image]
gdje je R1 kao što je prethodno ovdje definiran;
naznačen time, da obuhvaća postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 5 i nadalje obuhvaća korak (S4) i prema potrebi obuhvaća korak (S5):
(S4): reakciju spoja opće formule III s redukcijskim sredstvom; i opcionalno
(S5): cijepanje zaštitnih skupina R2 koje nisu vodik, u spoju stvorenom od spoja opće formule III u koraku (S4).
7. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 6, naznačen time, da reagens sadrži alkil-magnezijeve podvrste iskorištene u koraku (S1) i/ili u otopini koja sadrži takav reagens, gdje molarni omjer željeznih iona prema C1-4-alkil-magnezijevim podvrstama, ne prelazi 40 ppm.
8. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 7, naznačen time, da su materijali na površinama tehničke opreme koje mogu doći u doticaj s otopinom koja sadrži alkil-magnezijeve podvrste iskorištene u koraku (S1) i/ili s reakcijskim smjesama iz koraka (S1) i/ili (S2), otporni protiv oslobađanja ili ispiranja željeznih iona, tako da molarni omjer željeznih iona u reakcijskim smjesama iz koraka (S1) i/ili (S2) prema spoju I koji je angažiran u koraku (S1), ne prelazi 40 ppm.
9. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 8, naznačen time, da su materijali na površinama tehničke opreme koje mogu doći u doticaj s otopinom koja sadrži alkil-magnezijeve podvrste iskorištene u koraku (S1), otporni protiv oslobađanja ili ispiranja željeznih iona, tako da u navedenoj otopini, molarni omjer željeznih iona prema C1-4-alkil-magnezijevim podvrstama, ne prelazi 40 ppm.
10. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 9, naznačen time, da su materijali na površinama tehničke opreme koje mogu doći u doticaj s otopinom koja sadrži alkil-magnezijeve podvrste iskorištene u koraku (S1), i/ili s reakcijskim smjesama iz koraka (S1) i/ili (S2), odabrani iz skupine koja se sastoji od metalnih legura s masenim frakcijama željeza od ne više od 10%.
11. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 9, naznačen time, da su materijali na površinama tehničke opreme koje mogu doći u doticaj s otopinom koja sadrži alkil-magnezijeve podvrste iskorištene u koraku (S1), i/ili s reakcijskim smjesama iz koraka (S1) i/ili (S2), odabrani iz skupine koja se sastoji od materijala koji se obrađuju i/ili oblažu u svrhu sprečavanja oslobađanja ili ispiranja željeznih iona.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP16193735 | 2016-10-13 | ||
| EP17777935.2A EP3526229B1 (en) | 2016-10-13 | 2017-10-09 | Process for preparing glucopyranosyl-substituted benzyl-benzene derivatives |
| PCT/EP2017/075664 WO2018069243A1 (en) | 2016-10-13 | 2017-10-09 | Process for preparing glucopyranosyl-substituted benzyl-benzene derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20211154T1 true HRP20211154T1 (hr) | 2021-10-15 |
Family
ID=57136729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20211154TT HRP20211154T1 (hr) | 2016-10-13 | 2021-07-19 | Postupak za pripravu derivata benzil-benzena supstituiranih glukopiranozilom |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US20190309004A1 (hr) |
| EP (2) | EP3889144A1 (hr) |
| JP (1) | JP2019530722A (hr) |
| DK (1) | DK3526229T3 (hr) |
| ES (1) | ES2878583T3 (hr) |
| HR (1) | HRP20211154T1 (hr) |
| HU (1) | HUE055463T2 (hr) |
| PL (1) | PL3526229T3 (hr) |
| PT (1) | PT3526229T (hr) |
| SI (1) | SI3526229T1 (hr) |
| WO (1) | WO2018069243A1 (hr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UY32919A (es) | 2009-10-02 | 2011-04-29 | Boehringer Ingelheim Int | Composición farmacéutica, forma de dosificación farmacéutica, procedimiento para su preparación, mé todos para su tratamiento y sus usos |
| UY33937A (es) | 2011-03-07 | 2012-09-28 | Boehringer Ingelheim Int | Composiciones farmacéuticas que contienen inhibidores de dpp-4 y/o sglt-2 y metformina |
| US20140303098A1 (en) | 2013-04-05 | 2014-10-09 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| US20140303097A1 (en) | 2013-04-05 | 2014-10-09 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| US11813275B2 (en) | 2013-04-05 | 2023-11-14 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| CN105377266A (zh) | 2013-04-18 | 2016-03-02 | 勃林格殷格翰国际有限公司 | 药物组合物、治疗方法及其用途 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2557801C (en) | 2004-03-16 | 2013-06-25 | Boehringer Ingelheim International Gmbh | Glucopyranosyl-substituted benzol derivatives, drugs containing said compounds, the use thereof and method for the production thereof |
| UA91546C2 (uk) | 2005-05-03 | 2010-08-10 | Бьорінгер Інгельхайм Інтернаціональ Гмбх | КРИСТАЛІЧНА ФОРМА 1-ХЛОР-4-(β-D-ГЛЮКОПІРАНОЗ-1-ИЛ)-2-[4-((S)-ТЕТРАГІДРОФУРАН-3-ІЛОКСИ)-БЕНЗИЛ]-БЕНЗОЛУ, СПОСІБ ЇЇ ОДЕРЖАННЯ ТА ЇЇ ЗАСТОСУВАННЯ ПРИ ПРИГОТУВАННІ ЛІКАРСЬКИХ ЗАСОБІВ |
| US7772191B2 (en) * | 2005-05-10 | 2010-08-10 | Boehringer Ingelheim International Gmbh | Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives and intermediates therein |
| SI2486029T1 (sl) | 2009-09-30 | 2015-10-30 | Boehringer Ingelheim International Gmbh | Postopki za pripravo z glukopiranozilom substituiranih benzil-benzenskih derivatov |
-
2017
- 2017-10-09 WO PCT/EP2017/075664 patent/WO2018069243A1/en unknown
- 2017-10-09 EP EP21169098.7A patent/EP3889144A1/en not_active Withdrawn
- 2017-10-09 DK DK17777935.2T patent/DK3526229T3/da active
- 2017-10-09 PT PT177779352T patent/PT3526229T/pt unknown
- 2017-10-09 SI SI201730802T patent/SI3526229T1/sl unknown
- 2017-10-09 ES ES17777935T patent/ES2878583T3/es active Active
- 2017-10-09 EP EP17777935.2A patent/EP3526229B1/en active Active
- 2017-10-09 JP JP2019520146A patent/JP2019530722A/ja active Pending
- 2017-10-09 PL PL17777935T patent/PL3526229T3/pl unknown
- 2017-10-09 HU HUE17777935A patent/HUE055463T2/hu unknown
- 2017-10-09 US US16/340,163 patent/US20190309004A1/en not_active Abandoned
-
2021
- 2021-07-19 HR HRP20211154TT patent/HRP20211154T1/hr unknown
-
2022
- 2022-10-25 US US18/049,341 patent/US20230100086A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP3526229B1 (en) | 2021-04-28 |
| DK3526229T3 (da) | 2021-07-19 |
| US20190309004A1 (en) | 2019-10-10 |
| WO2018069243A1 (en) | 2018-04-19 |
| PT3526229T (pt) | 2021-07-06 |
| JP2019530722A (ja) | 2019-10-24 |
| EP3889144A1 (en) | 2021-10-06 |
| PL3526229T3 (pl) | 2021-11-02 |
| SI3526229T1 (sl) | 2021-08-31 |
| HUE055463T2 (hu) | 2021-11-29 |
| EP3526229A1 (en) | 2019-08-21 |
| ES2878583T3 (es) | 2021-11-19 |
| US20230100086A1 (en) | 2023-03-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HRP20211154T1 (hr) | Postupak za pripravu derivata benzil-benzena supstituiranih glukopiranozilom | |
| IL263543A (en) | Methods and devices for synthesizing imaging agents, and their intermediates | |
| PL1489136T3 (pl) | Zastosowanie interkalacyjnych związków grafitu dających się ekspandować termicznie do wytwarzania uszczelnień ognioochronnych i sposób ich wytwarzania | |
| HRP20161282T1 (hr) | Postupak za proizvodnju estetrola | |
| RS51210B (sr) | Dobijanje pregaballina i srodnih jedinjenja | |
| CA2635917C (en) | Method for producing fluorinated organic compounds | |
| PE131099A1 (es) | Compuestos terapeuticamente activos basados en el reemplazo bioisostero del catecol por el indazol en inhibidores de pde4 | |
| JP2017222882A5 (hr) | ||
| MY146368A (en) | Glucopyranosyl-substituted benzonitrile derivatives, pharmaceutical compositions containing such compounds, their use and process for their manufacture | |
| EA200500877A1 (ru) | Получение блоков галогенидов редкоземельных металлов | |
| IL180428A0 (en) | Novel flame-retardant polystyrenes | |
| WO2010015652A3 (en) | Thiazole compounds as medicaments for the treatment of (inter alia) cardiovascular diseases | |
| BG106203A (en) | Method for the preparation of pure citalopram | |
| CN106008411A (zh) | 手性4-取代基二氢呋喃-2(3h)-酮的制备方法 | |
| MX2009003739A (es) | Derivados de hidrobenzamida como inhibidores de hsp90. | |
| JP2008540414A5 (hr) | ||
| NO20076402L (no) | Imaging 18F or 11C-labelled alkylthiophenyl guanidines | |
| NO20080739L (no) | Fremgangsmater for behandling av Epileptogenese | |
| JP2013084680A (ja) | 透明導電性薄膜積層体のエッチング液 | |
| GB0327760D0 (en) | Compounds | |
| PL386741A1 (pl) | Sposób wytwarzania halogenków związków dihydroksytrialkiloamoniowych i zawierające je produkty | |
| Li et al. | Iodocyclization of trifluoromethylallenic phosphonates: an efficient approach to trifluoromethylated oxaphospholenes | |
| Mori et al. | Development of Boron-Cluster-Based Progesterone Receptor Antagonists Bearing a Pentafluorosulfanyl (SF5) Group | |
| WO2006028959A3 (en) | Apparatus and method to prepare a microsphere-forming composition | |
| WO2004029064A8 (en) | (+)-trans-isomers of (1-phosphonomethoxy-2-alkylcyclopropyl) methyl nucleoside derivatives, process for the preparation of stereoisomers thereof, and use of antiviral agents thereof |