DE2323216C3 - Verfahren zur Auftrennung von Stereoisomerengemischen von Pregna-1,4dien-11 -ol-33-dionen - Google Patents
Verfahren zur Auftrennung von Stereoisomerengemischen von Pregna-1,4dien-11 -ol-33-dionenInfo
- Publication number
- DE2323216C3 DE2323216C3 DE2323216A DE2323216A DE2323216C3 DE 2323216 C3 DE2323216 C3 DE 2323216C3 DE 2323216 A DE2323216 A DE 2323216A DE 2323216 A DE2323216 A DE 2323216A DE 2323216 C3 DE2323216 C3 DE 2323216C3
- Authority
- DE
- Germany
- Prior art keywords
- stereoisomeric
- separation
- component
- pregna
- isomer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
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- 238000000926 separation method Methods 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 11
- QQCBOIWDENXRLP-BYZMTCBYSA-N (8s,9s,10r,13r,14s,17s)-17-ethyl-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydro-3h-cyclopenta[a]phenanthrene Chemical compound C1CC2=CCC=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 QQCBOIWDENXRLP-BYZMTCBYSA-N 0.000 claims 1
- 230000001766 physiological effect Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 230000000694 effects Effects 0.000 description 12
- 238000002523 gelfiltration Methods 0.000 description 12
- 150000003431 steroids Chemical class 0.000 description 12
- 230000014759 maintenance of location Effects 0.000 description 10
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- 239000002904 solvent Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 210000001541 thymus gland Anatomy 0.000 description 9
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- FEBLZLNTKCEFIT-VSXGLTOVSA-N fluocinolone acetonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O FEBLZLNTKCEFIT-VSXGLTOVSA-N 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
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- 238000005481 NMR spectroscopy Methods 0.000 description 5
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- 239000012043 crude product Substances 0.000 description 5
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
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- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
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- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
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- 125000000217 alkyl group Chemical group 0.000 description 3
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- WBGKWQHBNHJJPZ-LECWWXJVSA-N desonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O WBGKWQHBNHJJPZ-LECWWXJVSA-N 0.000 description 3
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
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- OFFSPAZVIVZPHU-UHFFFAOYSA-N 1-benzofuran-2-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)=CC2=C1 OFFSPAZVIVZPHU-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 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
- 229960001347 fluocinolone acetonide Drugs 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
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- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 2
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- 238000003786 synthesis reaction Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 2
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- XYVVSFGOAQGVRE-AYHYENMDSA-N (8s,9s,10r,13s,14s,17s)-17-acetyl-11-hydroxy-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical class C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2O XYVVSFGOAQGVRE-AYHYENMDSA-N 0.000 description 1
- ZJDRDTZQVOCKPI-UHFFFAOYSA-N 1-benzofuran-2-carbonyl chloride Chemical compound C1=CC=C2OC(C(=O)Cl)=CC2=C1 ZJDRDTZQVOCKPI-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
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- IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 210000002268 wool Anatomy 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)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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 (cg-RX-API-DMAC10.html) | 1972-05-19 | 1972-05-19 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2323216A1 DE2323216A1 (de) | 1973-11-29 |
| DE2323216B2 DE2323216B2 (de) | 1977-11-03 |
| DE2323216C3 true DE2323216C3 (de) | 1978-06-22 |
Family
ID=20269238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2323216A Expired DE2323216C3 (de) | 1972-05-19 | 1973-05-09 | Verfahren zur Auftrennung von Stereoisomerengemischen von Pregna-1,4dien-11 -ol-33-dionen |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3928326A (cg-RX-API-DMAC10.html) |
| JP (1) | JPS547794B2 (cg-RX-API-DMAC10.html) |
| BE (1) | BE799728A (cg-RX-API-DMAC10.html) |
| CA (1) | CA1003402A (cg-RX-API-DMAC10.html) |
| CY (1) | CY1012A (cg-RX-API-DMAC10.html) |
| DE (1) | DE2323216C3 (cg-RX-API-DMAC10.html) |
| DK (1) | DK133249C (cg-RX-API-DMAC10.html) |
| FI (1) | FI50711C (cg-RX-API-DMAC10.html) |
| FR (1) | FR2185406B1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1428416A (cg-RX-API-DMAC10.html) |
| HK (1) | HK49079A (cg-RX-API-DMAC10.html) |
| IL (1) | IL42154A (cg-RX-API-DMAC10.html) |
| KE (1) | KE2969A (cg-RX-API-DMAC10.html) |
| NL (1) | NL175917C (cg-RX-API-DMAC10.html) |
| SE (1) | SE378110B (cg-RX-API-DMAC10.html) |
| SU (1) | SU468408A3 (cg-RX-API-DMAC10.html) |
| ZA (1) | ZA732956B (cg-RX-API-DMAC10.html) |
Families Citing this family (73)
| 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 |
| DK0678097T3 (da) * | 1993-01-08 | 2000-02-07 | Astra Ab | Hidtil ukendte colon- eller ileumspecifikke steroidderivater |
| 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 drugs containing it for use in the treatment of primary insomnia, and the manufacture of those drugs |
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| US20090054382A1 (en) * | 2005-10-19 | 2009-02-26 | Abhijit Ray | Compositions of phosphodiesterase type iv inhibitors |
| BRPI0717058A2 (pt) * | 2006-09-22 | 2013-10-15 | Ranbaxy Lab Ltd | Composto, composição farmacêutica, método para tratar, prevenir, inibir ou suprimir uma condição inflamatória ou doença ou doenças do sistema nervoso central e método para a preparação de um composto |
| EP2066661A2 (en) * | 2006-09-22 | 2009-06-10 | Ranbaxy Laboratories Limited | Phosphodiesterase inhibitors |
| 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 |
| KR20120090100A (ko) | 2006-12-26 | 2012-08-16 | 파마시클릭스, 인코포레이티드 | 병용 치료에 있어서 히스톤 디아세틸라제 억제제 이용 및 생체표지 감시 방법 |
| 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 |
| NZ579645A (en) | 2007-03-14 | 2012-01-12 | Ranbaxy Lab Ltd | Pyrazolo (3, 4-b) pyridine derivatives as phosphodiesterase inhibitors |
| EP2124943A1 (en) * | 2007-03-14 | 2009-12-02 | Ranbaxy Laboratories Limited | Pyrazolo [3, 4-b]pyridine derivatives as phosphodiesterase inhibitors |
| AU2008269154B2 (en) | 2007-06-27 | 2014-06-12 | Merck Sharp & Dohme Llc | 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 |
| PE20120894A1 (es) * | 2009-09-11 | 2012-08-13 | Chiesi Farma Spa | Derivados de isoxazolidina |
| GB0916608D0 (en) | 2009-09-22 | 2009-11-04 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| CN102638981B (zh) | 2009-10-14 | 2015-07-22 | 默沙东公司 | 提高p53活性的取代的哌啶和其用途 |
| EP2534145A4 (en) | 2010-02-08 | 2013-09-11 | Kinagen Inc | THERAPEUTIC METHODS AND COMPOSITIONS INVOLVING THE INHIBITION OF ALLOSTERIC KINASE |
| US8999957B2 (en) | 2010-06-24 | 2015-04-07 | Merck Sharp & Dohme Corp. | Heterocyclic compounds as ERK inhibitors |
| EP2601293B1 (en) | 2010-08-02 | 2017-12-06 | Sirna Therapeutics, Inc. | RNA INTERFERENCE MEDIATED INHIBITION OF CATENIN (CADHERIN-ASSOCIATED PROTEIN), BETA 1 (CTNNB1) GENE EXPRESSION USING SHORT INTERFERING NUCLEIC ACID (siNA) |
| WO2012024170A2 (en) | 2010-08-17 | 2012-02-23 | Merck Sharp & Dohme Corp. | RNA INTERFERENCE MEDIATED INHIBITION OF HEPATITIS B VIRUS (HBV) GENE EXPRESSION USING SHORT INTERFERING NUCLEIC ACID (siNA) |
| EP2608669B1 (en) | 2010-08-23 | 2016-06-22 | Merck Sharp & Dohme Corp. | NOVEL PYRAZOLO[1,5-a]PYRIMIDINE DERIVATIVES AS mTOR INHIBITORS |
| WO2012030685A2 (en) | 2010-09-01 | 2012-03-08 | Schering Corporation | Indazole derivatives useful as erk inhibitors |
| US9242981B2 (en) | 2010-09-16 | 2016-01-26 | Merck Sharp & Dohme Corp. | Fused pyrazole derivatives as novel ERK inhibitors |
| EP3766975A1 (en) | 2010-10-29 | 2021-01-20 | Sirna Therapeutics, Inc. | Rna interference mediated inhibition of gene expression using short interfering nucleic acid (sina) |
| WO2012087772A1 (en) | 2010-12-21 | 2012-06-28 | Schering Corporation | Indazole derivatives useful as erk inhibitors |
| IN2013MN02170A (cg-RX-API-DMAC10.html) | 2011-04-21 | 2015-06-12 | Piramal Entpr Ltd | |
| CN103917231B (zh) | 2011-09-13 | 2016-09-28 | 药品循环有限责任公司 | 组蛋白脱乙酰酶抑制剂与苯达莫司汀的联合制剂及其用途 |
| US9023865B2 (en) | 2011-10-27 | 2015-05-05 | Merck Sharp & Dohme Corp. | Compounds that are ERK inhibitors |
| EP3919620A1 (en) | 2012-05-02 | 2021-12-08 | Sirna Therapeutics, Inc. | Short interfering nucleic acid (sina) compositions |
| BR112015003729A2 (pt) | 2012-08-24 | 2018-06-05 | Univ Texas | composto de fórmula estrutural i; composição farmacêutica; método de tratamento de uma doença mediada por caminho do hif; método de tratamento de uma doença causada por proliferação anormal de células; e método para alcançar um efeito em um paciente |
| US9155747B2 (en) * | 2012-09-13 | 2015-10-13 | Chiesi Farmaceutici S.P.A. | Isoxazolidine derivatives |
| RU2660429C2 (ru) | 2012-09-28 | 2018-07-06 | Мерк Шарп И Доум Корп. | Новые соединения, которые являются ингибиторами erk |
| PL2925888T3 (pl) | 2012-11-28 | 2018-03-30 | Merck Sharp & Dohme Corp. | Kompozycje i sposoby do stosowania w leczeniu nowotworów |
| KR102196882B1 (ko) | 2012-12-20 | 2020-12-30 | 머크 샤프 앤드 돔 코포레이션 | Hdm2 억제제로서의 치환된 이미다조피리딘 |
| WO2014120748A1 (en) | 2013-01-30 | 2014-08-07 | Merck Sharp & Dohme Corp. | 2,6,7,8 substituted purines as hdm2 inhibitors |
| US20160194368A1 (en) | 2013-09-03 | 2016-07-07 | 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 |
| EP3525785B1 (en) | 2016-10-12 | 2025-08-27 | Merck Sharp & Dohme LLC | Kdm5 inhibitors |
| ES3046537T3 (en) | 2016-11-08 | 2025-12-02 | Regeneron Pharma | Steroids and protein-conjugates thereof |
| IL270594B2 (en) | 2017-05-18 | 2024-06-01 | Regeneron Pharma | Cyclodextrin protein drug conjugates |
| SG11202004151YA (en) | 2017-11-07 | 2020-06-29 | Regeneron Pharma | Hydrophilic linkers for antibody drug conjugates |
| EP3706747B1 (en) | 2017-11-08 | 2025-09-03 | Merck Sharp & Dohme LLC | Prmt5 inhibitors |
| IL319417A (en) | 2018-01-08 | 2025-05-01 | Regeneron Pharma | Steroids and their anti-inflammatory properties |
| CN112533951A (zh) | 2018-05-09 | 2021-03-19 | 里珍纳龙药品有限公司 | 抗msr1抗体及其使用方法 |
| WO2020033284A1 (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 |
| MA53287A (fr) | 2018-08-07 | 2022-05-11 | Merck Sharp & Dohme | Inhibiteurs de prmt5 |
| CA3160153A1 (en) | 2019-12-17 | 2021-06-24 | Michelle Machacek | Prmt5 inhibitors |
| US12441730B2 (en) | 2019-12-17 | 2025-10-14 | Merck Sharp & Dohme Llc | PRMT5 inhibitors |
| US20230108114A1 (en) | 2019-12-17 | 2023-04-06 | Merck Sharp & Dohme Llc | Prmt5 inhibitors |
| CA3265870A1 (en) | 2022-09-02 | 2024-03-07 | Merck Sharp & Dohme Llc | Pharmaceutical compositions based on topoisomerase-1 inhibitors derived from Exatecan, and their uses |
| EP4608453A1 (en) | 2022-10-25 | 2025-09-03 | Merck Sharp & Dohme LLC | Exatecan-derived adc linker-payloads, pharmaceutical compositions, and uses thereof |
| IL321395A (en) | 2022-12-14 | 2025-08-01 | Merck Sharp & Dohme Llc | Auristatin cargo-linkers, pharmaceutical compounds, and their uses |
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 IL IL42154A patent/IL42154A/en unknown
- 1973-05-01 ZA ZA732956A patent/ZA732956B/xx unknown
- 1973-05-09 DE DE2323216A patent/DE2323216C3/de not_active Expired
- 1973-05-09 CY CY1012A patent/CY1012A/xx unknown
- 1973-05-09 GB GB2219573A patent/GB1428416A/en not_active Expired
- 1973-05-14 FI FI731543A patent/FI50711C/fi active
- 1973-05-14 US US359913A patent/US3928326A/en not_active Expired - Lifetime
- 1973-05-17 DK DK277073A patent/DK133249C/da 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 NL NLAANVRAGE7306979,A patent/NL175917C/xx not_active IP Right Cessation
- 1973-05-18 CA CA171,781A patent/CA1003402A/en 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 |
|---|---|
| DE2323216B2 (de) | 1977-11-03 |
| AU5525273A (en) | 1974-11-07 |
| FR2185406B1 (cg-RX-API-DMAC10.html) | 1976-12-31 |
| CA1003402A (en) | 1977-01-11 |
| GB1428416A (en) | 1976-03-17 |
| DK133249C (da) | 1976-09-13 |
| IL42154A0 (en) | 1973-07-30 |
| BE799728A (fr) | 1973-09-17 |
| NL7306979A (cg-RX-API-DMAC10.html) | 1973-11-21 |
| HK49079A (en) | 1979-07-27 |
| FI50711C (fi) | 1976-06-10 |
| IL42154A (en) | 1976-12-31 |
| DK133249B (da) | 1976-04-12 |
| DE2323216A1 (de) | 1973-11-29 |
| NL175917C (nl) | 1985-01-16 |
| FR2185406A1 (cg-RX-API-DMAC10.html) | 1974-01-04 |
| JPS4941379A (cg-RX-API-DMAC10.html) | 1974-04-18 |
| NL175917B (nl) | 1984-08-16 |
| JPS547794B2 (cg-RX-API-DMAC10.html) | 1979-04-10 |
| KE2969A (en) | 1979-07-20 |
| US3928326A (en) | 1975-12-23 |
| FI50711B (cg-RX-API-DMAC10.html) | 1976-03-01 |
| SE378110B (cg-RX-API-DMAC10.html) | 1975-08-18 |
| ZA732956B (en) | 1974-04-24 |
| CY1012A (en) | 1979-11-23 |
| SU468408A3 (ru) | 1975-04-25 |
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