RU2012131164A - (метилсульфонил)этил-бензол-изоиндолиновые производные и их терапевтическое применение - Google Patents
(метилсульфонил)этил-бензол-изоиндолиновые производные и их терапевтическое применение Download PDFInfo
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- RU2012131164A RU2012131164A RU2012131164/04A RU2012131164A RU2012131164A RU 2012131164 A RU2012131164 A RU 2012131164A RU 2012131164/04 A RU2012131164/04 A RU 2012131164/04A RU 2012131164 A RU2012131164 A RU 2012131164A RU 2012131164 A RU2012131164 A RU 2012131164A
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- glucuronide
- stereoisomer
- solvate
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- -1 (Methylsulfonyl) Ethyl-Benzene-Isoindole Derivatives Chemical class 0.000 title claims abstract 3
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 14
- 239000001257 hydrogen Substances 0.000 claims abstract 14
- 208000035475 disorder Diseases 0.000 claims abstract 11
- 229930182480 glucuronide Chemical group 0.000 claims abstract 10
- 150000003839 salts Chemical class 0.000 claims abstract 10
- 239000012453 solvate Substances 0.000 claims abstract 10
- 150000008134 glucuronides Chemical group 0.000 claims abstract 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 6
- 201000010099 disease Diseases 0.000 claims abstract 4
- 238000011282 treatment Methods 0.000 claims abstract 4
- 206010028980 Neoplasm Diseases 0.000 claims abstract 2
- 201000011510 cancer Diseases 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 238000011321 prophylaxis Methods 0.000 claims abstract 2
- 150000002431 hydrogen Chemical class 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 208000030852 Parasitic disease Diseases 0.000 claims 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims 1
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 239000010425 asbestos Substances 0.000 claims 1
- 208000015114 central nervous system disease Diseases 0.000 claims 1
- 208000034737 hemoglobinopathy Diseases 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 208000002780 macular degeneration Diseases 0.000 claims 1
- 229910052895 riebeckite Inorganic materials 0.000 claims 1
- 208000017520 skin disease Diseases 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 7
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract 1
- 239000008103 glucose Substances 0.000 abstract 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
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- General Health & Medical Sciences (AREA)
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- Animal Behavior & Ethology (AREA)
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- Pharmacology & Pharmacy (AREA)
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- General Chemical & Material Sciences (AREA)
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- Neurosurgery (AREA)
- Neurology (AREA)
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- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
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- Heart & Thoracic Surgery (AREA)
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- Urology & Nephrology (AREA)
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- Tropical Medicine & Parasitology (AREA)
- Anesthesiology (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
1. Соединение формулы (I):или его фармацевтически приемлемая соль, сольват или стереоизомер, в котором:Rпредставляет собой водород, глюкуронид (“глюк”), или (циклопропил)-С(О)-, в котором циклопропил может быть замещен одной или более гидроксильными группами;Rпредставляет собой водород, метил или глюкуронид;Rпредставляет собой водород, этил или глюкуронид; иRпредставляет собой водород, гидроксил или -О-глюкуронид;при условии, что, когда Rпредставляет собой метил и Rпредставляет этил, тогда Rне может представлять замещенный (циклопропил)-О-.2. Соединение по п.1, в котором Rпредставляет водород.3. Соединение по п.1, в котором Rпредставляет (циклопропил)-С(О)-.4. Соединение по п.1, в котором Rпредставляет собой водород.5. Соединение по п.1, в котором Rпредставляет метил.6. Соединение по п.1, в котором Rпредставляет глюкуронид.7. Соединение по п.1, в котором Rпредставляет собой водород.8. Соединение по п.1, в котором Rпредставляет этил.9. Соединение по п.1, в котором Rпредставляет гидроксил.10. Соединение по п.1, в котором Rпредставляет -О- глюкуронид.11. Соединение по п.1, представляющее собой:или его фармацевтически приемлемая соль, сольват или стереоизомер.12. Соединение по п.1, которым являетсяили его фармацевтически приемлемая соль, сольват или стереоизомер.13. Фармацевтическая композиция, включающая соединение по п.1, или его фармацевтически приемлемую соль, сольват или стереоизомер.14. Способ терапии, профилактики или лечения заболевания или расстройства, включающий введение пациенту соединения по п.1, или его фармацевтически приемлемой соли, сольвата или стереоизомера, в котором заболеванием или расстройством является рак, расстройство, связ�
Claims (14)
1. Соединение формулы (I):
или его фармацевтически приемлемая соль, сольват или стереоизомер, в котором:
R1 представляет собой водород, глюкуронид (“глюк”), или (циклопропил)-С(О)-, в котором циклопропил может быть замещен одной или более гидроксильными группами;
R2 представляет собой водород, метил или глюкуронид;
R3 представляет собой водород, этил или глюкуронид; и
R4 представляет собой водород, гидроксил или -О-глюкуронид;
при условии, что, когда R2 представляет собой метил и R3 представляет этил, тогда R1 не может представлять замещенный (циклопропил)-О-.
2. Соединение по п.1, в котором R1 представляет водород.
3. Соединение по п.1, в котором R1 представляет (циклопропил)-С(О)-.
4. Соединение по п.1, в котором R2 представляет собой водород.
5. Соединение по п.1, в котором R2 представляет метил.
6. Соединение по п.1, в котором R2 представляет глюкуронид.
7. Соединение по п.1, в котором R3 представляет собой водород.
8. Соединение по п.1, в котором R3 представляет этил.
9. Соединение по п.1, в котором R4 представляет гидроксил.
10. Соединение по п.1, в котором R4 представляет -О- глюкуронид.
11. Соединение по п.1, представляющее собой:
или его фармацевтически приемлемая соль, сольват или стереоизомер.
12. Соединение по п.1, которым является
или его фармацевтически приемлемая соль, сольват или стереоизомер.
13. Фармацевтическая композиция, включающая соединение по п.1, или его фармацевтически приемлемую соль, сольват или стереоизомер.
14. Способ терапии, профилактики или лечения заболевания или расстройства, включающий введение пациенту соединения по п.1, или его фармацевтически приемлемой соли, сольвата или стереоизомера, в котором заболеванием или расстройством является рак, расстройство, связанное с ангиогенезом, боль, макулярная дегенерация или родственный синдром, заболевание кожи, легочная болезнь, связанное с асбестом расстройство, паразитарное заболевание, воспалительное расстройство, расстройство ЦНС, повреждение ЦНС, атеросклероз или родственное расстройство, дисфункциональный сон или родственное расстройство, гемоглобинопатия или родственное расстройство, или связанное с TNFα расстройство.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28935609P | 2009-12-22 | 2009-12-22 | |
| US61/289,356 | 2009-12-22 | ||
| PCT/US2010/061420 WO2011079091A1 (en) | 2009-12-22 | 2010-12-21 | (methylsulfonyl) ethyl benzene isoindoline derivatives and their therapeutical uses |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2012131164A true RU2012131164A (ru) | 2014-01-27 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012131164/04A RU2012131164A (ru) | 2009-12-22 | 2010-12-21 | (метилсульфонил)этил-бензол-изоиндолиновые производные и их терапевтическое применение |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US8716252B2 (ru) |
| EP (1) | EP2516395A1 (ru) |
| JP (1) | JP5760008B2 (ru) |
| KR (1) | KR20120113219A (ru) |
| CN (1) | CN102770412A (ru) |
| AU (1) | AU2010333767A1 (ru) |
| BR (1) | BR112012015129A2 (ru) |
| CA (1) | CA2783616A1 (ru) |
| CL (1) | CL2012001671A1 (ru) |
| CO (1) | CO6640204A2 (ru) |
| CR (1) | CR20120335A (ru) |
| EC (1) | ECSP12011987A (ru) |
| MX (1) | MX2012007217A (ru) |
| PH (1) | PH12012501237A1 (ru) |
| RU (1) | RU2012131164A (ru) |
| SG (1) | SG181891A1 (ru) |
| WO (1) | WO2011079091A1 (ru) |
| ZA (1) | ZA201203944B (ru) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012135299A1 (en) | 2011-03-28 | 2012-10-04 | Deuteria Pharmaceuticals Inc | 2',6'-dioxo-3'-deutero-piperdin-3-yl-isoindoline compounds |
| WO2014110558A1 (en) | 2013-01-14 | 2014-07-17 | Deuterx, Llc | 3-(5-substituted-4-oxoquinazolin-3(4h)-yl)-3-deutero-piperidine-2,6-dione derivatives |
| EP2968334A4 (en) | 2013-03-14 | 2016-08-03 | Deuterx Llc | 3- (SUBSTITIERTES-4-OXO-quinazolin-3 (4H) -yl) -3-deutero-PIPERIDINE-2,6-DIONE DERIVATIVES |
| US9809603B1 (en) | 2015-08-18 | 2017-11-07 | Deuterx, Llc | Deuterium-enriched isoindolinonyl-piperidinonyl conjugates and oxoquinazolin-3(4H)-yl-piperidinonyl conjugates and methods of treating medical disorders using same |
| SG10201913878YA (en) | 2016-03-17 | 2020-03-30 | Hoffmann La Roche | 5-ethyl-4-methyl-pyrazole-3-carboxamide derivative having activity as agonist of taar |
| US20190008837A1 (en) * | 2016-12-15 | 2019-01-10 | University Of Utah Research Foundation | Ophthalmic compositions and associated methods |
| US11976059B2 (en) | 2018-08-16 | 2024-05-07 | Korea Research Institute Of Chemical Technology | Isoindolin-1-on derivative, method for preparing same, and pharmaceutical composition comprising same as effective component for preventing or treating cancer |
| PE20220711A1 (es) * | 2019-09-27 | 2022-05-04 | Takeda Pharmaceuticals Co | Derivados de 2-isoindol-1,3,4-oxadiazol utiles como inhibidores de la histona desacetilasa 6 (hdac6) |
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| US3916899A (en) | 1973-04-25 | 1975-11-04 | Alza Corp | Osmotic dispensing device with maximum and minimum sizes for the passageway |
| US4008719A (en) | 1976-02-02 | 1977-02-22 | Alza Corporation | Osmotic system having laminar arrangement for programming delivery of active agent |
| IE58110B1 (en) | 1984-10-30 | 1993-07-14 | Elan Corp Plc | Controlled release powder and process for its preparation |
| US5073543A (en) | 1988-07-21 | 1991-12-17 | G. D. Searle & Co. | Controlled release formulations of trophic factors in ganglioside-lipsome vehicle |
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| US5580578A (en) | 1992-01-27 | 1996-12-03 | Euro-Celtique, S.A. | Controlled release formulations coated with aqueous dispersions of acrylic polymers |
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2010
- 2010-12-21 BR BR112012015129A patent/BR112012015129A2/pt not_active IP Right Cessation
- 2010-12-21 JP JP2012546129A patent/JP5760008B2/ja not_active Expired - Fee Related
- 2010-12-21 AU AU2010333767A patent/AU2010333767A1/en not_active Abandoned
- 2010-12-21 EP EP10801055A patent/EP2516395A1/en not_active Withdrawn
- 2010-12-21 KR KR1020127016076A patent/KR20120113219A/ko not_active Withdrawn
- 2010-12-21 US US13/518,843 patent/US8716252B2/en active Active
- 2010-12-21 PH PH1/2012/501237A patent/PH12012501237A1/en unknown
- 2010-12-21 RU RU2012131164/04A patent/RU2012131164A/ru not_active Application Discontinuation
- 2010-12-21 MX MX2012007217A patent/MX2012007217A/es active IP Right Grant
- 2010-12-21 CN CN2010800645105A patent/CN102770412A/zh active Pending
- 2010-12-21 WO PCT/US2010/061420 patent/WO2011079091A1/en active Application Filing
- 2010-12-21 CA CA2783616A patent/CA2783616A1/en not_active Abandoned
- 2010-12-21 SG SG2012046553A patent/SG181891A1/en unknown
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2012
- 2012-05-30 ZA ZA2012/03944A patent/ZA201203944B/en unknown
- 2012-06-20 CR CR20120335A patent/CR20120335A/es not_active Application Discontinuation
- 2012-06-20 CL CL2012001671A patent/CL2012001671A1/es unknown
- 2012-06-20 EC ECSP12011987 patent/ECSP12011987A/es unknown
- 2012-07-06 CO CO12113701A patent/CO6640204A2/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2783616A1 (en) | 2011-06-30 |
| JP5760008B2 (ja) | 2015-08-05 |
| ECSP12011987A (es) | 2012-09-28 |
| JP2013515073A (ja) | 2013-05-02 |
| KR20120113219A (ko) | 2012-10-12 |
| PH12012501237A1 (en) | 2012-11-26 |
| SG181891A1 (en) | 2012-07-30 |
| US8716252B2 (en) | 2014-05-06 |
| AU2010333767A1 (en) | 2012-07-05 |
| ZA201203944B (en) | 2013-08-28 |
| EP2516395A1 (en) | 2012-10-31 |
| CN102770412A (zh) | 2012-11-07 |
| CR20120335A (es) | 2012-10-31 |
| BR112012015129A2 (pt) | 2019-09-24 |
| CO6640204A2 (es) | 2013-03-22 |
| MX2012007217A (es) | 2012-07-10 |
| US20130116204A1 (en) | 2013-05-09 |
| CL2012001671A1 (es) | 2012-11-23 |
| WO2011079091A1 (en) | 2011-06-30 |
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