GB1428416A - Process for the separation of stereoisomeric mixtures of steroid acetals into their components and components obtained thereby - Google Patents
Process for the separation of stereoisomeric mixtures of steroid acetals into their components and components obtained therebyInfo
- Publication number
- GB1428416A GB1428416A GB2219573A GB2219573A GB1428416A GB 1428416 A GB1428416 A GB 1428416A GB 2219573 A GB2219573 A GB 2219573A GB 2219573 A GB2219573 A GB 2219573A GB 1428416 A GB1428416 A GB 1428416A
- Authority
- GB
- United Kingdom
- Prior art keywords
- mixtures
- components
- acetals
- steroid
- gel
- 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
- 239000000203 mixture Substances 0.000 title abstract 6
- 238000000926 separation method Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title 1
- -1 steroid acetals Chemical class 0.000 title 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 238000002523 gelfiltration Methods 0.000 abstract 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- 229920005654 Sephadex Polymers 0.000 abstract 1
- 238000006359 acetalization reaction Methods 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 239000003480 eluent Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 238000011200 topical administration Methods 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 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 (https=) | 1972-05-19 | 1972-05-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1428416A true GB1428416A (en) | 1976-03-17 |
Family
ID=20269238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2219573A Expired GB1428416A (en) | 1972-05-19 | 1973-05-09 | Process for the separation of stereoisomeric mixtures of steroid acetals into their components and components obtained thereby |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3928326A (https=) |
| JP (1) | JPS547794B2 (https=) |
| BE (1) | BE799728A (https=) |
| CA (1) | CA1003402A (https=) |
| CY (1) | CY1012A (https=) |
| DE (1) | DE2323216C3 (https=) |
| DK (1) | DK133249C (https=) |
| FI (1) | FI50711C (https=) |
| FR (1) | FR2185406B1 (https=) |
| GB (1) | GB1428416A (https=) |
| HK (1) | HK49079A (https=) |
| IL (1) | IL42154A (https=) |
| KE (1) | KE2969A (https=) |
| NL (1) | NL175917C (https=) |
| SE (1) | SE378110B (https=) |
| SU (1) | SU468408A3 (https=) |
| ZA (1) | ZA732956B (https=) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2108653A1 (en) | 2008-04-11 | 2009-10-14 | INDUSTRIALE CHIMICA S.r.l. | Process for preparing budesonide |
| US10711032B2 (en) | 2016-11-08 | 2020-07-14 | Regeneron Pharmaceuticals, Inc. | Steroids and protein-conjugates thereof |
| US11377502B2 (en) | 2018-05-09 | 2022-07-05 | Regeneron Pharmaceuticals, Inc. | Anti-MSR1 antibodies and methods of use thereof |
| US11491237B2 (en) | 2017-05-18 | 2022-11-08 | Regeneron Pharmaceuticals, Inc. | Cyclodextrin protein drug conjugates |
| US12070506B2 (en) | 2018-01-08 | 2024-08-27 | Regeneron Pharmaceuticals, Inc. | Steroids and antibody-conjugates thereof |
| US12134631B2 (en) | 2017-11-07 | 2024-11-05 | Regeneron Pharmaceuticals, Inc. | Hydrophilic linkers for antibody drug conjugates |
Families Citing this family (69)
| 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 |
| CA2152374A1 (en) * | 1993-01-08 | 1994-07-21 | Ralph Lennart Brattsand | Novel colon- or ileum-specific steroid derivatives |
| 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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| WO2007031838A1 (en) | 2005-09-16 | 2007-03-22 | Ranbaxy Laboratories Limited | Substituted pyrazolo [3,4-b] pyridines as phosphodiesterase inhibitors |
| WO2007045980A1 (en) * | 2005-10-19 | 2007-04-26 | Ranbaxy Laboratories Limited | Compositions of phosphodiesterase type iv inhibitors |
| RU2008119323A (ru) | 2005-10-19 | 2009-11-27 | Рэнбакси Лабораториз Лимитед (In) | Фармацевтические композиции мускаринового рецептора |
| EA200900472A1 (ru) * | 2006-09-22 | 2009-10-30 | Ранбакси Лабораторис Лимитед | Ингибиторы фосфодиэстеразы iv типа |
| US20100029728A1 (en) * | 2006-09-22 | 2010-02-04 | 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 |
| RU2446796C2 (ru) | 2006-12-26 | 2012-04-10 | Фармасайкликс, Инк. | Способ использования ингибиторов гистондеацетилазы и мониторинга биомаркеров в комбинированной терапии |
| AR064777A1 (es) | 2007-01-10 | 2009-04-22 | Inst Di Reserche D Biolog Mole | Indazoles sustituidos con amida como inhibidores de poli (adp- ribosa) polimerasa (parp) |
| EP1958947A1 (en) | 2007-02-15 | 2008-08-20 | Ranbaxy Laboratories Limited | Inhibitors of phosphodiesterase type 4 |
| WO2008111009A1 (en) * | 2007-03-14 | 2008-09-18 | Ranbaxy Laboratories Limited | Pyrazolo [3, 4-b] pyridine derivatives as phosphodiesterase inhibitors |
| DK2124944T3 (da) | 2007-03-14 | 2012-04-23 | Ranbaxy Lab Ltd | Pyrazolo[3,4-b]pyridinderivater som phosphodiesteraseinhibitorer |
| EP3103791B1 (en) | 2007-06-27 | 2018-01-31 | Merck Sharp & Dohme Corp. | 4-carboxybenzylamino derivatives as histone deacetylase inhibitors |
| 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 |
| WO2010114780A1 (en) | 2009-04-01 | 2010-10-07 | 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 |
| WO2011029547A2 (en) * | 2009-09-11 | 2011-03-17 | Chiesi Farmaceutici S.P.A. | Pregnane derivatives condensed in the 16, 17 position with an n-substituted isoxazolidine ring as anti-inflammatory agents |
| GB0916608D0 (en) | 2009-09-22 | 2009-11-04 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| US8859776B2 (en) | 2009-10-14 | 2014-10-14 | Merck Sharp & Dohme Corp. | Substituted piperidines that increase p53 activity and the uses thereof |
| WO2011097594A2 (en) | 2010-02-08 | 2011-08-11 | Kinagen, Inc. | Therapeutic methods and compositions involving allosteric kinase inhibition |
| 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) |
| 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) |
| 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 |
| US9242981B2 (en) | 2010-09-16 | 2016-01-26 | Merck Sharp & Dohme Corp. | Fused pyrazole derivatives as novel ERK inhibitors |
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| EP2654748B1 (en) | 2010-12-21 | 2016-07-27 | Merck Sharp & Dohme Corp. | Indazole derivatives useful as erk inhibitors |
| WO2012143879A1 (en) | 2011-04-21 | 2012-10-26 | Piramal Healthcare Limited | A crystalline form of a salt of a morpholino sulfonyl indole derivative and a process for its preparation |
| AU2011376953B2 (en) | 2011-09-13 | 2017-08-24 | Pharmacyclics Llc | Formulations of histone deacetylase inhibitor in combination with bendamustine and uses thereof |
| EP2770987B1 (en) | 2011-10-27 | 2018-04-04 | Merck Sharp & Dohme Corp. | Novel compounds that are erk inhibitors |
| WO2013165816A2 (en) | 2012-05-02 | 2013-11-07 | Merck Sharp & Dohme Corp. | SHORT INTERFERING NUCLEIC ACID (siNA) COMPOSITIONS |
| ES2691643T3 (es) | 2012-08-24 | 2018-11-28 | Board Of Regents, The University Of Texas System | Moduladores heterocíclicos de la actividad de HIF para el tratamiento de enfermedades |
| US9155747B2 (en) * | 2012-09-13 | 2015-10-13 | Chiesi Farmaceutici S.P.A. | Isoxazolidine derivatives |
| WO2014052563A2 (en) | 2012-09-28 | 2014-04-03 | Merck Sharp & Dohme Corp. | Novel compounds that are erk inhibitors |
| ME02925B (me) | 2012-11-28 | 2018-04-20 | Merck Sharp & Dohme | Kompozicije i postupci za liječenje kancera |
| TW201429969A (zh) | 2012-12-20 | 2014-08-01 | Merck Sharp & Dohme | 作爲ｈｄｍ２抑制劑之經取代咪唑吡啶 |
| 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 |
| US10975084B2 (en) | 2016-10-12 | 2021-04-13 | Merck Sharp & Dohme Corp. | KDM5 inhibitors |
| EP3706747B1 (en) | 2017-11-08 | 2025-09-03 | Merck Sharp & Dohme LLC | Prmt5 inhibitors |
| US11981701B2 (en) | 2018-08-07 | 2024-05-14 | Merck Sharp & Dohme Llc | PRMT5 inhibitors |
| EP3833669A4 (en) | 2018-08-07 | 2022-05-11 | Merck Sharp & Dohme Corp. | PRMT5 INHIBITORS |
| WO2020033288A1 (en) | 2018-08-07 | 2020-02-13 | Merck Sharp & Dohme Corp. | Prmt5 inhibitors |
| WO2020033282A1 (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 |
| CN115003303B (zh) | 2019-12-17 | 2024-03-08 | 默沙东公司 | Prmt5抑制剂 |
| US12595248B2 (en) | 2019-12-17 | 2026-04-07 | Merck Sharp & Dohme Llc | PRMT5 inhibitors |
| JP2025511436A (ja) | 2022-09-02 | 2025-04-16 | メルク・シャープ・アンド・ドーム・エルエルシー | エキサテカン由来トポイソメラーゼ－１阻害薬医薬組成物及びその使用 |
| CN120417935A (zh) | 2022-10-25 | 2025-08-01 | 默沙东有限责任公司 | 依喜替康衍生的adc接头-载荷及其药物组合物和用途 |
| 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 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 SU SU1918554A patent/SU468408A3/ru active
- 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 CA CA171,781A patent/CA1003402A/en not_active Expired
- 1973-05-18 FR FR7318126A patent/FR2185406B1/fr not_active Expired
- 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
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2108653A1 (en) | 2008-04-11 | 2009-10-14 | INDUSTRIALE CHIMICA S.r.l. | Process for preparing budesonide |
| US10711032B2 (en) | 2016-11-08 | 2020-07-14 | Regeneron Pharmaceuticals, Inc. | Steroids and protein-conjugates thereof |
| US11760775B2 (en) | 2016-11-08 | 2023-09-19 | Regeneron Pharmaceuticals, Inc. | Steroids and protein-conjugates thereof |
| US12377159B2 (en) | 2016-11-08 | 2025-08-05 | Regeneron Pharmaceuticals, Inc. | Steroids and protein-conjugates thereof |
| US11491237B2 (en) | 2017-05-18 | 2022-11-08 | Regeneron Pharmaceuticals, Inc. | Cyclodextrin protein drug conjugates |
| US12589101B2 (en) | 2017-05-18 | 2026-03-31 | Regeneron Pharmaceuticals, Inc. | Cyclodextrin protein drug conjugates |
| US12134631B2 (en) | 2017-11-07 | 2024-11-05 | Regeneron Pharmaceuticals, Inc. | Hydrophilic linkers for antibody drug conjugates |
| US12070506B2 (en) | 2018-01-08 | 2024-08-27 | Regeneron Pharmaceuticals, Inc. | Steroids and antibody-conjugates thereof |
| US11377502B2 (en) | 2018-05-09 | 2022-07-05 | Regeneron Pharmaceuticals, Inc. | Anti-MSR1 antibodies and methods of use thereof |
| US12497460B2 (en) | 2018-05-09 | 2025-12-16 | Regeneron Pharmaceuticals, Inc. | Anti-MSR1 antibodies and methods of use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| HK49079A (en) | 1979-07-27 |
| JPS547794B2 (https=) | 1979-04-10 |
| FR2185406A1 (https=) | 1974-01-04 |
| DK133249C (da) | 1976-09-13 |
| DE2323216B2 (de) | 1977-11-03 |
| CY1012A (en) | 1979-11-23 |
| CA1003402A (en) | 1977-01-11 |
| DE2323216C3 (de) | 1978-06-22 |
| KE2969A (en) | 1979-07-20 |
| FR2185406B1 (https=) | 1976-12-31 |
| NL7306979A (https=) | 1973-11-21 |
| ZA732956B (en) | 1974-04-24 |
| DK133249B (da) | 1976-04-12 |
| SE378110B (https=) | 1975-08-18 |
| AU5525273A (en) | 1974-11-07 |
| NL175917C (nl) | 1985-01-16 |
| FI50711B (https=) | 1976-03-01 |
| JPS4941379A (https=) | 1974-04-18 |
| US3928326A (en) | 1975-12-23 |
| IL42154A (en) | 1976-12-31 |
| BE799728A (fr) | 1973-09-17 |
| IL42154A0 (en) | 1973-07-30 |
| NL175917B (nl) | 1984-08-16 |
| SU468408A3 (ru) | 1975-04-25 |
| FI50711C (fi) | 1976-06-10 |
| DE2323216A1 (de) | 1973-11-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19930508 |