SU468408A3 - Способ разделени стереоизомерных смесей - Google Patents
Способ разделени стереоизомерных смесейInfo
- Publication number
- SU468408A3 SU468408A3 SU1918554A SU1918554A SU468408A3 SU 468408 A3 SU468408 A3 SU 468408A3 SU 1918554 A SU1918554 A SU 1918554A SU 1918554 A SU1918554 A SU 1918554A SU 468408 A3 SU468408 A3 SU 468408A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- gel
- separation
- fluorine
- filtration
- carried out
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 18
- 238000000926 separation method Methods 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 10
- 230000014759 maintenance of location Effects 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 229910052731 fluorine Chemical group 0.000 claims description 6
- 239000011737 fluorine Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000003431 steroids Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 101100421503 Arabidopsis thaliana SIGA gene Proteins 0.000 claims 1
- 101100042610 Arabidopsis thaliana SIGB gene Proteins 0.000 claims 1
- 229920002307 Dextran Polymers 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 241000218657 Picea Species 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- 239000000499 gel Substances 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 229920005654 Sephadex Polymers 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- -1 heterocyclic carboxylic acid Chemical class 0.000 description 6
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 6
- 239000012507 Sephadex™ Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 101100476979 Rhodobacter capsulatus sdsA gene Proteins 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical group C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 description 1
- OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 1
- 101100476983 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) SDT1 gene Proteins 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 1
- 229960003868 paraldehyde Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/0026—Oxygen-containing hetero ring cyclic ketals
- C07J71/0031—Oxygen-containing hetero ring cyclic ketals at positions 16, 17
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7206645A SE378110B (enExample) | 1972-05-19 | 1972-05-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU468408A3 true SU468408A3 (ru) | 1975-04-25 |
Family
ID=20269238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1918554A SU468408A3 (ru) | 1972-05-19 | 1973-05-18 | Способ разделени стереоизомерных смесей |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3928326A (enExample) |
| JP (1) | JPS547794B2 (enExample) |
| BE (1) | BE799728A (enExample) |
| CA (1) | CA1003402A (enExample) |
| CY (1) | CY1012A (enExample) |
| DE (1) | DE2323216C3 (enExample) |
| DK (1) | DK133249C (enExample) |
| FI (1) | FI50711C (enExample) |
| FR (1) | FR2185406B1 (enExample) |
| GB (1) | GB1428416A (enExample) |
| HK (1) | HK49079A (enExample) |
| IL (1) | IL42154A (enExample) |
| KE (1) | KE2969A (enExample) |
| NL (1) | NL175917C (enExample) |
| SE (1) | SE378110B (enExample) |
| SU (1) | SU468408A3 (enExample) |
| ZA (1) | ZA732956B (enExample) |
Families Citing this family (74)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL188581C (nl) * | 1974-07-15 | 1992-08-03 | Akzo Nv | Werkwijze voor het bereiden van 11beta-hydroxy-18-alkylestraanverbindingen. |
| ZA763131B (en) * | 1975-05-27 | 1978-01-25 | Syntex Inc | Use of flunisolide to treat respiratory diseases |
| SE8008524L (sv) * | 1980-12-04 | 1982-06-05 | Draco Ab | 4-pregnen-derivat, ett forfarande for deras framstellning, beredning och metod for behandling av inflammatoriska tillstand |
| IT1196142B (it) * | 1984-06-11 | 1988-11-10 | Sicor Spa | Procedimento per la preparazione di 16,17-acetali di derivati pregnanici e nuovi composti ottenuti |
| SE8604059D0 (sv) * | 1986-09-25 | 1986-09-25 | Astra Pharma Prod | A method of controlling the epimeric distribution in the preparation of 16,17-acetals of pregnane derivatives |
| GR1001529B (el) * | 1990-09-07 | 1994-03-31 | Elmuquimica Farm Sl | Μέ?οδος για την λήψη νέων 21-εστέρων της 16-17-ακετάλης της πρ να-1,4-διενο-3,20-διόνης. |
| SE9100341D0 (sv) * | 1991-02-04 | 1991-02-04 | Astra Ab | Novel steroids |
| RU95115547A (ru) * | 1993-01-08 | 1997-06-10 | Астра Актиеболаг (SE) | Стероидные соединения, способы их получения и фармацевтический препарат |
| DE19635498A1 (de) * | 1996-09-03 | 1998-03-26 | Byk Gulden Lomberg Chem Fab | Verfahren zur Epimerenanreicherung |
| IT1291288B1 (it) | 1997-04-30 | 1999-01-07 | Farmabios Srl | Processo per la preparazione di 16,17 acetali di derivati pregnanici con controllo della distribuzione epimerica al c-22. |
| US6266556B1 (en) | 1998-04-27 | 2001-07-24 | Beth Israel Deaconess Medical Center, Inc. | Method and apparatus for recording an electroencephalogram during transcranial magnetic stimulation |
| IL144900A (en) | 2001-08-14 | 2013-12-31 | Neurim Pharma 1991 | Melatonin and medicaments comprising it for use in treating primary insomnia and in the manufacture of such medicaments |
| AR045536A1 (es) * | 2003-08-29 | 2005-11-02 | Ranbaxy Lab Ltd | Inhibidores de la fosfodiesterasa tipo -iv |
| US20070259874A1 (en) * | 2003-11-26 | 2007-11-08 | Palle Venkata P | Phosphodiesterase Inhibitors |
| WO2005100356A1 (en) | 2004-04-09 | 2005-10-27 | Merck & Co., Inc. | Inhibitors of akt activity |
| EP1888050B1 (en) | 2005-05-17 | 2012-03-21 | Merck Sharp & Dohme Ltd. | cis-4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)cyclohexanepropanoic acid for the treatment of cancer |
| US7915286B2 (en) | 2005-09-16 | 2011-03-29 | Ranbaxy Laboratories Limited | Substituted pyrazolo [3,4-b] pyridines as phosphodiesterase inhibitors |
| EP1948167A1 (en) * | 2005-10-19 | 2008-07-30 | Ranbaxy Laboratories, Ltd. | Compositions of phosphodiesterase type iv inhibitors |
| RU2008119323A (ru) | 2005-10-19 | 2009-11-27 | Рэнбакси Лабораториз Лимитед (In) | Фармацевтические композиции мускаринового рецептора |
| EP2066661A2 (en) * | 2006-09-22 | 2009-06-10 | Ranbaxy Laboratories Limited | Phosphodiesterase inhibitors |
| JP2010504323A (ja) * | 2006-09-22 | 2010-02-12 | ランバクシー ラボラトリーズ リミテッド | Ｉｖ型ホスホジエステラーゼの阻害物質 |
| US20110218176A1 (en) | 2006-11-01 | 2011-09-08 | Barbara Brooke Jennings-Spring | Compounds, methods, and treatments for abnormal signaling pathways for prenatal and postnatal development |
| CA2674084C (en) | 2006-12-26 | 2013-05-14 | Pharmacyclics, Inc. | Method of using histone deacetylase inhibitors and monitoring biomarkers in combination therapy |
| EP2805945B1 (en) | 2007-01-10 | 2019-04-03 | MSD Italia S.r.l. | Amide substituted indazoles as poly(ADP-ribose)polymerase (PARP) inhibitors |
| US20080207659A1 (en) * | 2007-02-15 | 2008-08-28 | Asit Kumar Chakraborti | Inhibitors of phosphodiesterase type 4 |
| US20110130403A1 (en) * | 2007-03-14 | 2011-06-02 | Ranbaxy Laboratories Limited | Pyrazolo [3, 4-b] pyridine derivatives as phosphodiesterase inhibitors |
| SI2124944T1 (sl) * | 2007-03-14 | 2012-05-31 | Ranbaxy Lab Ltd | Derivati pirazolo b piridina kot inhibitorji fosfodiesteraze |
| US8389553B2 (en) | 2007-06-27 | 2013-03-05 | Merck Sharp & Dohme Corp. | 4-carboxybenzylamino derivatives as histone deacetylase inhibitors |
| ITMI20080645A1 (it) | 2008-04-11 | 2009-10-12 | Ind Chimica Srl | Procedimento per la preparazione di budesonide |
| EP2111861A1 (en) | 2008-04-21 | 2009-10-28 | Ranbaxy Laboratories Limited | Compositions of phosphodiesterase type IV inhibitors |
| GB0900484D0 (en) | 2009-01-13 | 2009-02-11 | Angeletti P Ist Richerche Bio | Therapeutic agent |
| US8691825B2 (en) | 2009-04-01 | 2014-04-08 | Merck Sharp & Dohme Corp. | Inhibitors of AKT activity |
| US8603521B2 (en) | 2009-04-17 | 2013-12-10 | Pharmacyclics, Inc. | Formulations of histone deacetylase inhibitor and uses thereof |
| BR112012005503B1 (pt) * | 2009-09-11 | 2021-10-13 | Chiesi Farmaceutici S.P.A. | Derivados de isoxazolidina |
| GB0916608D0 (en) | 2009-09-22 | 2009-11-04 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| EP2488028B1 (en) | 2009-10-14 | 2020-08-19 | Merck Sharp & Dohme Corp. | Substituted piperidines that increase p53 activity and the uses thereof |
| JP2013518909A (ja) | 2010-02-08 | 2013-05-23 | キナゲン，インク． | アロステリックキナーゼ阻害が関係する治療方法および組成物 |
| WO2011163330A1 (en) | 2010-06-24 | 2011-12-29 | Merck Sharp & Dohme Corp. | Novel heterocyclic compounds as erk inhibitors |
| CN107090456B (zh) | 2010-08-02 | 2022-01-18 | 瑟纳治疗公司 | 使用短干扰核酸的RNA干扰介导的联蛋白（钙粘蛋白关联蛋白质），β1基因表达的抑制 |
| JP2013537423A (ja) | 2010-08-17 | 2013-10-03 | メルク・シャープ・エンド・ドーム・コーポレイション | 低分子干渉核酸（ｓｉＮＡ）を用いたＢ型肝炎ウイルス（ＨＢＶ）遺伝子発現のＲＮＡ干渉媒介性阻害 |
| US8883801B2 (en) | 2010-08-23 | 2014-11-11 | Merck Sharp & Dohme Corp. | Substituted pyrazolo[1,5-a]pyrimidines as mTOR inhibitors |
| WO2012030685A2 (en) | 2010-09-01 | 2012-03-08 | Schering Corporation | Indazole derivatives useful as erk inhibitors |
| EP2615916B1 (en) | 2010-09-16 | 2017-01-04 | Merck Sharp & Dohme Corp. | Fused pyrazole derivatives as novel erk inhibitors |
| DK2632472T3 (en) | 2010-10-29 | 2018-03-19 | Sirna Therapeutics Inc | RNA INTERFERENCE-MEDIATED INHIBITION OF GENE EXPRESSION USING SHORT INTERFERRING NUCLEIC ACIDS (SINA) |
| WO2012087772A1 (en) | 2010-12-21 | 2012-06-28 | Schering Corporation | Indazole derivatives useful as erk inhibitors |
| EP2699568A1 (en) | 2011-04-21 | 2014-02-26 | Piramal Enterprises Limited | A crystalline form of a salt of a morpholino sulfonyl indole derivative and a process for its preparation |
| RU2609833C2 (ru) | 2011-09-13 | 2017-02-06 | Фармасайкликс Элэлси | Лекарственные формы ингибитора гистондиацетилазы в комбинации с бендамутином и их применение |
| WO2013063214A1 (en) | 2011-10-27 | 2013-05-02 | Merck Sharp & Dohme Corp. | Novel compounds that are erk inhibitors |
| EP2844261B1 (en) | 2012-05-02 | 2018-10-17 | Sirna Therapeutics, Inc. | SHORT INTERFERING NUCLEIC ACID (siNA) COMPOSITIONS |
| JP6453218B2 (ja) | 2012-08-24 | 2019-01-16 | ボード・オブ・リージエンツ，ザ・ユニバーシテイ・オブ・テキサス・システム | 疾患を治療するためのｈｉｆ活性の複素環式修飾物質 |
| US9155747B2 (en) * | 2012-09-13 | 2015-10-13 | Chiesi Farmaceutici S.P.A. | Isoxazolidine derivatives |
| CN105050598B (zh) | 2012-09-28 | 2018-04-27 | 默沙东公司 | 作为erk抑制剂的新型化合物 |
| RS56680B1 (sr) | 2012-11-28 | 2018-03-30 | Merck Sharp & Dohme | Kompozicije i postupci za lečenje kancera |
| US8846657B2 (en) | 2012-12-20 | 2014-09-30 | Merck Sharp & Dohme Corp. | Substituted imidazopyridines as HDM2 inhibitors |
| WO2014120748A1 (en) | 2013-01-30 | 2014-08-07 | Merck Sharp & Dohme Corp. | 2,6,7,8 substituted purines as hdm2 inhibitors |
| EP3041938A1 (en) | 2013-09-03 | 2016-07-13 | Moderna Therapeutics, Inc. | Circular polynucleotides |
| US11066396B2 (en) | 2016-06-23 | 2021-07-20 | Merck Sharp & Dohme Corp. | 3-aryl- heteroaryl substituted 5-trifluoromethyl oxadiazoles as histonedeacetylase 6 (HDAC6) inhibitors |
| US10975084B2 (en) | 2016-10-12 | 2021-04-13 | Merck Sharp & Dohme Corp. | KDM5 inhibitors |
| KR20190074310A (ko) | 2016-11-08 | 2019-06-27 | 리제너론 파마슈티칼스 인코포레이티드 | 스테로이드 및 이의 단백질-접합체 |
| CA3063871A1 (en) | 2017-05-18 | 2018-11-22 | Regeneron Pharmaceuticals, Inc. | Cyclodextrin protein drug conjugates |
| JP7426931B2 (ja) | 2017-11-07 | 2024-02-02 | レゲネロン ファーマシューティカルス，インコーポレーテッド | 抗体薬物コンジュゲートのための親水性リンカー |
| US11098059B2 (en) | 2017-11-08 | 2021-08-24 | Merck Sharp & Dohme Corp. | PRMT5 inhibitors |
| BR112020013492A2 (pt) | 2018-01-08 | 2020-12-08 | Regeneron Pharmaceuticals, Inc. | Esteroides e conjugados de anticorpo dos mesmos |
| KR20210008008A (ko) | 2018-05-09 | 2021-01-20 | 리제너론 파마슈티칼스 인코포레이티드 | 항-msr1 항체 및 이의 사용 방법 |
| CA3108388A1 (en) | 2018-08-07 | 2020-02-13 | Merck Sharp & Dohme Corp. | Prmt5 inhibitors |
| EP3833668B1 (en) | 2018-08-07 | 2025-03-19 | Merck Sharp & Dohme LLC | Prmt5 inhibitors |
| EP3833667B1 (en) | 2018-08-07 | 2024-03-13 | Merck Sharp & Dohme LLC | Prmt5 inhibitors |
| WO2020033285A1 (en) | 2018-08-07 | 2020-02-13 | Merck Sharp & Dohme Corp. | Prmt5 inhibitors |
| EP4076460B1 (en) | 2019-12-17 | 2026-01-21 | Merck Sharp & Dohme LLC | 1,4-dihydro-2h-spiro[isoquinoline-3,4'-piperidine derivatives as prmt5 inhibitors for the treatment of cancer |
| JP7589247B2 (ja) | 2019-12-17 | 2024-11-25 | メルク・シャープ・アンド・ドーム・エルエルシー | Ｐｒｍｔ５阻害剤 |
| WO2021126728A1 (en) | 2019-12-17 | 2021-06-24 | Merck Sharp & Dohme Corp. | Prmt5 inhibitors |
| GEAP202516720A (en) | 2022-09-02 | 2025-07-10 | Merck Sharp & Dohme Llc | Exatecan-derived topoisomerase-1 inhibitors pharmaceutical compositions, and uses thereof |
| IL320396A (en) | 2022-10-25 | 2025-06-01 | Merck Sharp & Dohme Llc | Charge-linkers of anti-drug conjugates derived from extacan, pharmaceutical compositions, and uses thereof |
| US20240207425A1 (en) | 2022-12-14 | 2024-06-27 | Merck Sharp & Dohme Llc | Auristatin linker-payloads, pharmaceutical compositions, and uses thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3133940A (en) * | 1956-04-10 | 1964-05-19 | Glaxo Group Ltd | Process for the separation of delta-1, 4-3-keto steroid compounds from mixtures thereof with other 3-keto steroids |
| US3197469A (en) * | 1958-08-06 | 1965-07-27 | Pharmaceutical Res Products In | 16, 17-acetals and ketals of 6-halo-16, 17-dihydroxy steroids of the pregnane seriesand intermediates therefor |
| US3048581A (en) * | 1960-04-25 | 1962-08-07 | Olin Mathieson | Acetals and ketals of 16, 17-dihydroxy steroids |
| US3128238A (en) * | 1962-09-14 | 1964-04-07 | Lilly Co Eli | delta1-dehydrogenation of steroids by fermentation with actinoplanaceae |
-
1972
- 1972-05-19 SE SE7206645A patent/SE378110B/xx unknown
-
1973
- 1973-05-01 ZA ZA732956A patent/ZA732956B/xx unknown
- 1973-05-01 IL IL42154A patent/IL42154A/en unknown
- 1973-05-09 CY CY1012A patent/CY1012A/xx unknown
- 1973-05-09 GB GB2219573A patent/GB1428416A/en not_active Expired
- 1973-05-09 DE DE2323216A patent/DE2323216C3/de not_active Expired
- 1973-05-14 US US359913A patent/US3928326A/en not_active Expired - Lifetime
- 1973-05-14 FI FI731543A patent/FI50711C/fi active
- 1973-05-17 DK DK277073A patent/DK133249C/da not_active IP Right Cessation
- 1973-05-18 CA CA171,781A patent/CA1003402A/en not_active Expired
- 1973-05-18 NL NLAANVRAGE7306979,A patent/NL175917C/xx not_active IP Right Cessation
- 1973-05-18 BE BE131271A patent/BE799728A/xx not_active IP Right Cessation
- 1973-05-18 FR FR7318126A patent/FR2185406B1/fr not_active Expired
- 1973-05-18 SU SU1918554A patent/SU468408A3/ru active
- 1973-05-19 JP JP5623473A patent/JPS547794B2/ja not_active Expired
-
1979
- 1979-06-20 KE KE2969A patent/KE2969A/xx unknown
- 1979-07-19 HK HK490/79A patent/HK49079A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL42154A0 (en) | 1973-07-30 |
| ZA732956B (en) | 1974-04-24 |
| JPS4941379A (enExample) | 1974-04-18 |
| FI50711B (enExample) | 1976-03-01 |
| KE2969A (en) | 1979-07-20 |
| US3928326A (en) | 1975-12-23 |
| CY1012A (en) | 1979-11-23 |
| BE799728A (fr) | 1973-09-17 |
| NL175917C (nl) | 1985-01-16 |
| GB1428416A (en) | 1976-03-17 |
| AU5525273A (en) | 1974-11-07 |
| DE2323216A1 (de) | 1973-11-29 |
| DE2323216B2 (de) | 1977-11-03 |
| DK133249B (da) | 1976-04-12 |
| CA1003402A (en) | 1977-01-11 |
| DK133249C (da) | 1976-09-13 |
| HK49079A (en) | 1979-07-27 |
| NL7306979A (enExample) | 1973-11-21 |
| JPS547794B2 (enExample) | 1979-04-10 |
| DE2323216C3 (de) | 1978-06-22 |
| NL175917B (nl) | 1984-08-16 |
| FR2185406B1 (enExample) | 1976-12-31 |
| IL42154A (en) | 1976-12-31 |
| SE378110B (enExample) | 1975-08-18 |
| FI50711C (fi) | 1976-06-10 |
| FR2185406A1 (enExample) | 1974-01-04 |
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