IL42155A - 16alpha,17alpha-alkylidenedioxy-11beta,21-dihydroxy-pregna-1,4-diene-3,20-diones their manufacture and preparations containing same - Google Patents
16alpha,17alpha-alkylidenedioxy-11beta,21-dihydroxy-pregna-1,4-diene-3,20-diones their manufacture and preparations containing sameInfo
- Publication number
- IL42155A IL42155A IL42155A IL4215573A IL42155A IL 42155 A IL42155 A IL 42155A IL 42155 A IL42155 A IL 42155A IL 4215573 A IL4215573 A IL 4215573A IL 42155 A IL42155 A IL 42155A
- Authority
- IL
- Israel
- Prior art keywords
- acid
- fluorine
- steroids
- hydroxyl
- formula
- Prior art date
Links
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- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000003431 steroids Chemical class 0.000 claims abstract description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 229910052731 fluorine Chemical group 0.000 claims description 10
- 239000011737 fluorine Chemical group 0.000 claims description 10
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims description 6
- CILPHQCEVYJUDN-UHFFFAOYSA-N 2-(5-methyl-2-propan-2-ylcyclohexyl)oxyacetic acid Chemical compound CC(C)C1CCC(C)CC1OCC(O)=O CILPHQCEVYJUDN-UHFFFAOYSA-N 0.000 claims description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
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- 150000004665 fatty acids Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 4
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- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid group Chemical group C(CCCCC)(=O)O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 3
- 235000001968 nicotinic acid Nutrition 0.000 claims description 3
- 239000011664 nicotinic acid Substances 0.000 claims description 3
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 claims description 2
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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 claims description 2
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- 229920000136 polysorbate Polymers 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 1
- RVQZKNOMKUSGCI-UHFFFAOYSA-N pyridine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=NC=C1 RVQZKNOMKUSGCI-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- 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
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229960005294 triamcinolone Drugs 0.000 description 1
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
- 238000005303 weighing Methods 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
- 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
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7206644A SE378109B (en, 2012) | 1972-05-19 | 1972-05-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL42155A0 IL42155A0 (en) | 1973-07-30 |
| IL42155A true IL42155A (en) | 1977-06-30 |
Family
ID=20269234
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42155A IL42155A (en) | 1972-05-19 | 1973-05-01 | 16alpha,17alpha-alkylidenedioxy-11beta,21-dihydroxy-pregna-1,4-diene-3,20-diones their manufacture and preparations containing same |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US3929768A (en, 2012) |
| JP (1) | JPS5521760B2 (en, 2012) |
| AT (1) | AT328630B (en, 2012) |
| BE (1) | BE799727A (en, 2012) |
| CA (1) | CA1002938A (en, 2012) |
| CH (1) | CH595400A5 (en, 2012) |
| CS (1) | CS178129B2 (en, 2012) |
| CY (1) | CY1013A (en, 2012) |
| DD (1) | DD104295A5 (en, 2012) |
| DE (1) | DE2323215C3 (en, 2012) |
| DK (1) | DK134783B (en, 2012) |
| ES (1) | ES414673A1 (en, 2012) |
| FI (1) | FI50631C (en, 2012) |
| FR (1) | FR2185405B1 (en, 2012) |
| GB (1) | GB1429922A (en, 2012) |
| HK (1) | HK49179A (en, 2012) |
| HU (1) | HU166680B (en, 2012) |
| IL (1) | IL42155A (en, 2012) |
| KE (1) | KE2970A (en, 2012) |
| NL (2) | NL177493C (en, 2012) |
| NO (2) | NO139640C (en, 2012) |
| PL (1) | PL87765B1 (en, 2012) |
| SE (1) | SE378109B (en, 2012) |
| SU (1) | SU470954A3 (en, 2012) |
| YU (1) | YU35896B (en, 2012) |
| ZA (1) | ZA732955B (en, 2012) |
Families Citing this family (144)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8004580L (sv) * | 1980-06-19 | 1981-12-20 | Draco Ab | Farmaceutisk beredning |
| 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 |
| SE8403905D0 (sv) * | 1984-07-30 | 1984-07-30 | Draco Ab | Liposomes and steroid esters |
| SE8501693D0 (sv) * | 1985-04-04 | 1985-04-04 | Draco Ab | Novel 16,17-acetalsubstituted androstane-17beta-carboxylic acid esters |
| US5215979A (en) * | 1985-12-19 | 1993-06-01 | Aktiebolaget Draco | 16,17-acetalsubstituted pregnane 21-oic acid derivatives |
| SE8506015D0 (sv) * | 1985-12-19 | 1985-12-19 | Draco Ab | Novel 16,17-acetalsubstituted pregnane 21-oic acid derivatives |
| 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 |
| LV5274A3 (lv) * | 1988-02-29 | 1993-10-10 | Richter Gedeon Vegyeszet | 22(R,S)-11 beta,21-dihidroksi-16 alpha,17-butilidenbisoksipregna-1,4-dien-3,20-diona iegusanas panemiens |
| HU203769B (en) * | 1989-03-09 | 1991-09-30 | Richter Gedeon Vegyeszet | Process for producing new steroide derivatives and pharmaceutical compositions containing them |
| SE8903219D0 (sv) * | 1989-10-02 | 1989-10-02 | Astra Ab | Process for the manufacture of budesonide |
| US5643602A (en) * | 1989-11-22 | 1997-07-01 | Astra Aktiebolag | Oral composition for the treatment of inflammatory bowel disease |
| SE8903914D0 (sv) | 1989-11-22 | 1989-11-22 | Draco Ab | Oral composition for the treatment of inflammatory bowel diseases |
| 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 |
| SE9100342D0 (sv) * | 1991-02-04 | 1991-02-04 | Astra Ab | Novel steroid esters |
| US5888995A (en) * | 1991-02-04 | 1999-03-30 | Astra Aktiebolag | Steroid esters |
| IE67345B1 (en) * | 1991-03-12 | 1996-03-20 | Akzo Nv | Low dose dry pharmaceutical preparations |
| FR2675146A1 (fr) * | 1991-04-10 | 1992-10-16 | Roussel Uclaf | Nouveaux derives sterouides de la pregna-1,4-diene-3,20-dione, leur preparation, leur application a la preparation de derives 16,17-methylene dioxy substitues et nouveaux intermediaires. |
| MD24B1 (ro) * | 1991-07-09 | 1994-05-31 | Parfumerii Si Cosmetice Vioric | Compozitie de substante odorante |
| LT3695B (en) | 1991-11-18 | 1996-02-26 | Dineika Raimundas Arnas | Folded roof |
| CA2356145A1 (en) * | 1991-12-18 | 1993-06-24 | Aktiebolaget Astra | New combination of formoterol and budesonide |
| HUT72442A (en) * | 1992-12-24 | 1996-04-29 | Rhone Poulenc Rorer Ltd | Steroids condensed with heteroring containing oxygene, pharmaceutical compositions containing them and processes for their production |
| SK87295A3 (en) * | 1993-01-08 | 1996-04-03 | Astra Ab | Novel colon or ileum-specific steroid derivatives |
| EP0701565B1 (de) | 1993-04-02 | 1998-10-28 | Byk Gulden Lomberg Chemische Fabrik GmbH | Neue prednisolonderivate |
| GB9423919D0 (en) * | 1994-11-26 | 1995-01-11 | Rhone Poulenc Rorer Ltd | Chemical process |
| US6166024A (en) | 1995-03-30 | 2000-12-26 | Mayo Foundation For Medical Education And Research | Use of topical azathioprine and thioguanine to treat colorectal adenomas |
| FR2756739B1 (fr) * | 1996-12-05 | 2000-04-28 | Astra Ab | Nouvelle formulation de budesonide |
| 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. |
| DE29717252U1 (de) * | 1997-09-26 | 1998-02-19 | Dr. Falk Pharma GmbH, 79108 Freiburg | Arzneimittelkit aus einem Budesonid-haltigen und einem Ursodesoxycholsäure-haltigen Arzneimittel zur Behandlung von cholestatischen Lebererkrankungen |
| 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 |
| US6667299B1 (en) * | 2000-03-16 | 2003-12-23 | Hollis-Eden Pharmaceuticals, Inc. | Pharmaceutical compositions and treatment methods |
| CZ20013912A3 (cs) | 1999-05-04 | 2002-05-15 | Strakan Limited | Androgen glykosid, sloučenina, testosteron-ß-D-glukosid, 5 alfa-Dihydrotestosteron- 17ß-D-glukosid, farmaceutický prostředek a pouľití sloučeniny |
| GB0009613D0 (en) * | 2000-04-18 | 2000-06-07 | Glaxo Group Ltd | Pharmaceutical compositions |
| GB0009584D0 (en) * | 2000-04-18 | 2000-06-07 | Glaxo Group Ltd | Pharmaceutical compositions |
| GB0009583D0 (en) * | 2000-04-18 | 2000-06-07 | Glaxo Group Ltd | Respiratory formulations |
| AR028948A1 (es) * | 2000-06-20 | 2003-05-28 | Astrazeneca Ab | Compuestos novedosos |
| US6667344B2 (en) | 2001-04-17 | 2003-12-23 | Dey, L.P. | Bronchodilating compositions and methods |
| US20030055026A1 (en) * | 2001-04-17 | 2003-03-20 | Dey L.P. | Formoterol/steroid bronchodilating compositions and methods of use thereof |
| 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 |
| US20040235811A1 (en) * | 2002-10-08 | 2004-11-25 | Sepracor Inc. | Fatty acid modified forms of glucocorticoids |
| EP1620083A2 (en) * | 2003-04-18 | 2006-02-01 | Pharmacia & Upjohn Company LLC | Combination therapies |
| TWI359675B (en) | 2003-07-10 | 2012-03-11 | Dey L P | Bronchodilating β-agonist compositions |
| WO2005021515A2 (en) * | 2003-08-29 | 2005-03-10 | Ranbaxy Laboratories Limited | Inhibitors of phosphodiesterase type-iv |
| WO2005051931A2 (en) * | 2003-11-26 | 2005-06-09 | Ranbaxy Laboratories Limited | Phosphodiesterase inhibitors |
| EP1737861A4 (en) | 2004-04-09 | 2010-04-28 | Merck Sharp & Dohme | HEMMER OF ACT ACTIVITY |
| US8362075B2 (en) | 2005-05-17 | 2013-01-29 | Merck Sharp & Dohme Corp. | Cyclohexyl sulphones for treatment of cancer |
| ES2265276B1 (es) | 2005-05-20 | 2008-02-01 | Laboratorios Almirall S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor beta2 adrenergico. |
| TW200738634A (en) | 2005-08-02 | 2007-10-16 | Astrazeneca Ab | New salt |
| TW200744612A (en) * | 2005-08-26 | 2007-12-16 | Astrazeneca Ab | New combination |
| EP1934219A1 (en) | 2005-09-16 | 2008-06-25 | Ranbaxy Laboratories Limited | Substituted pyrazolo [3,4-b] pyridines as phosphodiesterase inhibitors |
| WO2007045979A1 (en) | 2005-10-19 | 2007-04-26 | Ranbaxy Laboratories Limited | Pharmaceutical compositions of muscarinic receptor antagonists |
| US20090054382A1 (en) * | 2005-10-19 | 2009-02-26 | Abhijit Ray | Compositions of phosphodiesterase type iv inhibitors |
| WO2007056181A2 (en) * | 2005-11-02 | 2007-05-18 | Sicor, Inc. | Process for the preparation of ciclesonide |
| AR059216A1 (es) | 2006-01-27 | 2008-03-19 | Sun Pharmaceutical Ind Ltd | 11b-hidroxiandrosta-4-eno-3-onas |
| US20070232578A1 (en) * | 2006-02-15 | 2007-10-04 | Pierluigi Rossetto | Crystalline forms of ciclesonide |
| ES2296516B1 (es) * | 2006-04-27 | 2009-04-01 | Laboratorios Almirall S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor beta2 adrenergico. |
| CL2007002427A1 (es) * | 2006-08-22 | 2008-03-14 | Ranbaxy Lab Ltd | Compuestos derivados heterociclicos, inhibidores de metaloproteinasa de matriz; proceso de preparacion; composicion farmaceutica, util para el tratamiento o profilaxis de enfermedades inflamatorias o desordenes autoinmunes. |
| EP2066661A2 (en) * | 2006-09-22 | 2009-06-10 | Ranbaxy Laboratories Limited | Phosphodiesterase inhibitors |
| EA200900472A1 (ru) * | 2006-09-22 | 2009-10-30 | Ранбакси Лабораторис Лимитед | Ингибиторы фосфодиэстеразы iv типа |
| ES2302447B1 (es) * | 2006-10-20 | 2009-06-12 | Laboratorios Almirall S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor beta2 adrenergico. |
| 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 |
| AU2008204380B2 (en) | 2007-01-10 | 2013-08-15 | Msd Italia S.R.L. | Amide substituted indazoles as poly(ADP-ribose)polymerase (PARP) inhibitors |
| GB0702456D0 (en) | 2007-02-08 | 2007-03-21 | Astrazeneca Ab | New combination |
| ES2306595B1 (es) * | 2007-02-09 | 2009-09-11 | Laboratorios Almirall S.A. | Sal de napadisilato de 5-(2-((6-(2,2-difluoro-2-feniletoxi)hexil)amino)-1-hidroxietil)-8-hidroxiquinolin-2(1h)-ona como agonista del receptor adrenergico beta2. |
| EP1958639A1 (en) | 2007-02-14 | 2008-08-20 | Polichem S.A. | Use of chitosans for the treatment of nail inflammatory diseases |
| US10201490B2 (en) | 2007-02-14 | 2019-02-12 | Polichem Sa | Use of chitosans for the treatment of nail inflammatory diseases |
| EP1958947A1 (en) | 2007-02-15 | 2008-08-20 | Ranbaxy Laboratories Limited | Inhibitors of phosphodiesterase type 4 |
| WO2008111010A1 (en) * | 2007-03-14 | 2008-09-18 | Ranbaxy Laboratories Limited | 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 |
| WO2009002495A1 (en) | 2007-06-27 | 2008-12-31 | Merck & Co., Inc. | 4-carboxybenzylamino derivatives as histone deacetylase inhibitors |
| US20090082319A1 (en) * | 2007-09-25 | 2009-03-26 | Protia, Llc | Deuterium-enriched budesonide |
| WO2009045539A2 (en) * | 2007-10-05 | 2009-04-09 | Nektar Therapeutics Al, Corporation | Oligomer-corticosteroid conjugates |
| ES2320961B1 (es) * | 2007-11-28 | 2010-03-17 | Laboratorios Almirall, S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor adrenergico beta2. |
| EP2096105A1 (en) * | 2008-02-28 | 2009-09-02 | Laboratorios Almirall, S.A. | Derivatives of 4-(2-amino-1-hydroxyethyl)phenol as agonists of the b2 adrenergic receptor |
| WO2009112557A2 (en) * | 2008-03-13 | 2009-09-17 | Farmabios S.P.A. | Process for the preparation of pregnane derivatives |
| 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 |
| CN101279997B (zh) * | 2008-05-29 | 2011-08-24 | 鲁南制药集团股份有限公司 | 布地奈德的一种制备方法 |
| UY32297A (es) | 2008-12-22 | 2010-05-31 | Almirall Sa | Sal mesilato de 5-(2-{[6-(2,2-difluoro-2-fenilitoxi) hexil]amino}-1-hidroxietil)-8-hidroxiquinolin-2( 1h)-ona como agonista del receptor b(beta)2 acrenérgico |
| GB0900484D0 (en) | 2009-01-13 | 2009-02-11 | Angeletti P Ist Richerche Bio | Therapeutic agent |
| EP2228368A1 (en) | 2009-03-12 | 2010-09-15 | Almirall, S.A. | Process for manufacturing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy) hexyl]amino}-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one |
| 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 |
| US8815258B2 (en) | 2009-05-29 | 2014-08-26 | Pearl Therapeutics, Inc. | Compositions, methods and systems for respiratory delivery of two or more active agents |
| JP5873013B2 (ja) | 2009-05-29 | 2016-03-01 | パール セラピューティクス，インコーポレイテッド | ２つ以上の活性剤を呼吸器送達するための組成物、方法および系 |
| GB0916608D0 (en) | 2009-09-22 | 2009-11-04 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| LT3403654T (lt) | 2009-10-01 | 2019-09-10 | Adare Development I, L.P. | Geriamosios kortikosteroido kompozicijos |
| AU2010307198C9 (en) | 2009-10-14 | 2014-02-13 | Merck Sharp & Dohme Corp. | Substituted piperidines that increase p53 activity and the uses thereof |
| WO2011073662A1 (en) | 2009-12-17 | 2011-06-23 | Astrazeneca Ab | Combination of a benzoxazinone and a further agent for treating respiratory diseases |
| WO2011093812A2 (en) | 2010-01-28 | 2011-08-04 | Mahmut Bilgic | Pharmaceutical formulation comprising tiotropium and budesonide in dry powder form |
| 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 |
| CN101863952B (zh) * | 2010-04-30 | 2013-04-17 | 湖北葛店人福药业有限责任公司 | 布地奈德的制备方法 |
| US8999957B2 (en) | 2010-06-24 | 2015-04-07 | Merck Sharp & Dohme Corp. | Heterocyclic compounds as ERK inhibitors |
| CA2805265A1 (en) | 2010-08-02 | 2012-02-09 | Merck Sharp & Dohme Corp. | Rna interference mediated inhibition of catenin (cadherin-associated protein), beta 1 (ctnnb1) gene expression using short interfering nucleic acid (sina) |
| CN103282497B (zh) | 2010-08-17 | 2018-07-10 | 瑟纳治疗公司 | 使用短干扰核酸(siNA)的乙型肝炎病毒(HBV)基因表达的RNA干扰介导的抑制 |
| US8883801B2 (en) | 2010-08-23 | 2014-11-11 | Merck Sharp & Dohme Corp. | Substituted pyrazolo[1,5-a]pyrimidines as mTOR inhibitors |
| US8946216B2 (en) | 2010-09-01 | 2015-02-03 | Merck Sharp & Dohme Corp. | Indazole derivatives useful as ERK inhibitors |
| WO2012036997A1 (en) | 2010-09-16 | 2012-03-22 | Schering Corporation | Fused pyrazole derivatives as novel erk inhibitors |
| EP2632472B1 (en) | 2010-10-29 | 2017-12-13 | Sirna Therapeutics, Inc. | Rna interference mediated inhibition of gene expression using short interfering nucleic acids (sina) |
| EP2654748B1 (en) | 2010-12-21 | 2016-07-27 | Merck Sharp & Dohme Corp. | Indazole derivatives useful as erk inhibitors |
| JP2014514321A (ja) | 2011-04-21 | 2014-06-19 | メルク・シャープ・アンド・ドーム・コーポレーション | インスリン様増殖因子１受容体阻害剤 |
| SG2014014419A (en) | 2011-09-13 | 2014-07-30 | Pharmacyclics Inc | Formulations of histone deacetylase inhibitor in combination with bendamustine and uses thereof |
| EP2578570A1 (en) | 2011-10-07 | 2013-04-10 | Almirall, S.A. | Novel process for preparing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1(r)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one via novel intermediates of synthesis. |
| EP2770987B1 (en) | 2011-10-27 | 2018-04-04 | Merck Sharp & Dohme Corp. | Novel compounds that are erk inhibitors |
| WO2013109214A1 (en) | 2012-01-16 | 2013-07-25 | Mahmut Bilgic | Process for the preparation of dry powder formulations |
| EP2641900A1 (en) | 2012-03-20 | 2013-09-25 | Almirall, S.A. | Novel polymorphic Crystal forms of 5-(2-{[6-(2,2-difluoro-2-phenylethoxy) hexyl]amino}-1-(R)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one, heminapadisylate as agonist of the ß2 adrenergic receptor. |
| US20150299696A1 (en) | 2012-05-02 | 2015-10-22 | Sirna Therapeutics, Inc. | SHORT INTERFERING NUCLEIC ACID (siNA) COMPOSITIONS |
| CN103421075B (zh) * | 2012-05-16 | 2017-07-28 | 上海特化医药科技有限公司 | 孕烷衍生物16,17‑缩醛(酮)的制备方法 |
| US10111957B2 (en) | 2012-07-05 | 2018-10-30 | Arven Ilac Snayi ve Ticaret A.S. | Inhalation compositions comprising glucose anhydrous |
| US20150165037A1 (en) | 2012-07-05 | 2015-06-18 | Arven llac Sanayi Ve Ticaret A.S. | Inhalation compositions comprising corticosteroid and sorbitol |
| US10105316B2 (en) | 2012-07-05 | 2018-10-23 | Arven llac Sanayi Ve Ticaret A.S. | Inhalation compositions comprising muscarinic receptor antagonist |
| WO2014007781A2 (en) | 2012-07-05 | 2014-01-09 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Inhalation compositions |
| EP2888255B1 (en) | 2012-08-24 | 2018-07-18 | Board of Regents, The University of Texas System | Heterocyclic modulators of hif activity for treatment of disease |
| KR20150060724A (ko) | 2012-09-28 | 2015-06-03 | 머크 샤프 앤드 돔 코포레이션 | Erk 억제제인 신규 화합물 |
| SMT201700595T1 (it) | 2012-11-28 | 2018-03-08 | Merck Sharp & Dohme | Composizioni e metodi per trattare il cancro |
| AR094116A1 (es) | 2012-12-20 | 2015-07-08 | Merck Sharp & Dohme | Imidazopiridinas sustituidas como inhibidores de hdm2 |
| US9540377B2 (en) | 2013-01-30 | 2017-01-10 | Merck Sharp & Dohme Corp. | 2,6,7,8 substituted purines as HDM2 inhibitors |
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| CA2936741C (en) | 2014-10-31 | 2018-11-06 | Purdue Pharma | Methods and compositions particularly for treatment of attention deficit disorder |
| EP3250211B1 (en) | 2015-01-30 | 2021-12-22 | Coral Drugs Pvt. Ltd. | Novel process for preparation of glucocorticoid steroids |
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| CA3063871A1 (en) | 2017-05-18 | 2018-11-22 | Regeneron Pharmaceuticals, Inc. | Cyclodextrin protein drug conjugates |
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| EP3706747A4 (en) | 2017-11-08 | 2021-08-04 | Merck Sharp & Dohme Corp. | PRMT5 INHIBITORS |
| MA54673A1 (fr) | 2018-01-08 | 2022-08-31 | Regeneron Pharma | Stéroïdes et leurs conjugués-anticorps |
| EP3790899A1 (en) | 2018-05-09 | 2021-03-17 | Regeneron Pharmaceuticals, Inc. | Anti-msr1 antibodies and methods of use thereof |
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| WO2020033284A1 (en) | 2018-08-07 | 2020-02-13 | Merck Sharp & Dohme Corp. | Prmt5 inhibitors |
| CN112805006B (zh) | 2018-08-07 | 2024-09-24 | 默沙东有限责任公司 | Prmt5抑制剂 |
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| CA3160153A1 (en) | 2019-12-17 | 2021-06-24 | Michelle Machacek | Prmt5 inhibitors |
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| JP2024545816A (ja) | 2021-12-20 | 2024-12-12 | アストラゼネカ・アクチエボラーグ | エアロゾル薬物送達のための組成物、方法及びシステム |
| PE20251401A1 (es) | 2022-09-02 | 2025-05-22 | Merck Sharp And Dohme Llc | Inhibidores de topoisomerasa-1 derivados de exatecan composiciones farmaceuticas y sus usos |
| KR20250079227A (ko) | 2022-10-25 | 2025-06-04 | 머크 샤프 앤드 돔 엘엘씨 | 엑사테칸-유래 adc 링커-페이로드, 제약 조성물, 및 그의 용도 |
| US20240207425A1 (en) | 2022-12-14 | 2024-06-27 | Merck Sharp & Dohme Llc | Auristatin linker-payloads, pharmaceutical compositions, and uses thereof |
Family Cites Families (7)
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|---|---|---|---|---|
| US3126375A (en) * | 1964-03-24 | Chioacyl | ||
| 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 |
| US2990401A (en) * | 1958-06-18 | 1961-06-27 | American Cyanamid Co | 11-substituted 16alpha, 17alpha-substituted methylenedioxy 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 |
| JPS4843910A (en, 2012) * | 1971-10-08 | 1973-06-25 |
-
1972
- 1972-05-19 SE SE7206644A patent/SE378109B/xx unknown
-
1973
- 1973-05-01 ZA ZA732955A patent/ZA732955B/xx unknown
- 1973-05-01 IL IL42155A patent/IL42155A/en unknown
- 1973-05-09 CY CY1013A patent/CY1013A/xx unknown
- 1973-05-09 GB GB2219473A patent/GB1429922A/en not_active Expired
- 1973-05-09 DE DE2323215A patent/DE2323215C3/de not_active Expired
- 1973-05-11 ES ES414673A patent/ES414673A1/es not_active Expired
- 1973-05-14 US US360051A patent/US3929768A/en not_active Expired - Lifetime
- 1973-05-14 FI FI731542A patent/FI50631C/fi active Protection Beyond IP Right Term
- 1973-05-16 YU YU1291/73A patent/YU35896B/xx unknown
- 1973-05-16 CH CH699973A patent/CH595400A5/xx not_active IP Right Cessation
- 1973-05-17 DK DK277273AA patent/DK134783B/da active Protection Beyond IP Right Term
- 1973-05-17 DD DD170888A patent/DD104295A5/xx unknown
- 1973-05-18 NO NO2059/73A patent/NO139640C/no unknown
- 1973-05-18 AT AT436573A patent/AT328630B/de not_active IP Right Cessation
- 1973-05-18 CA CA171,785A patent/CA1002938A/en not_active Expired
- 1973-05-18 BE BE131270A patent/BE799727A/xx active Protection Beyond IP Right Term
- 1973-05-18 NL NLAANVRAGE7306978,A patent/NL177493C/xx active Protection Beyond IP Right Term
- 1973-05-18 FR FR7318125A patent/FR2185405B1/fr not_active Expired
- 1973-05-18 CS CS3590A patent/CS178129B2/cs unknown
- 1973-05-18 SU SU1923451A patent/SU470954A3/ru active
- 1973-05-18 HU HUBO1438A patent/HU166680B/hu unknown
- 1973-05-18 PL PL1973162650A patent/PL87765B1/pl unknown
- 1973-05-19 JP JP5623373A patent/JPS5521760B2/ja not_active Expired
-
1975
- 1975-11-06 US US05/629,389 patent/US3983233A/en not_active Expired - Lifetime
-
1979
- 1979-06-20 KE KE2970A patent/KE2970A/xx unknown
- 1979-07-19 HK HK491/79A patent/HK49179A/xx unknown
-
1993
- 1993-04-13 NL NL930025C patent/NL930025I1/nl unknown
-
1994
- 1994-08-31 NO NO1994013C patent/NO1994013I1/no unknown
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