HRP20120183T1 - N-(2-aminofenil)-4-[n-(piridin-3-il)-metoksikarbonilaminometil]-benzamid (ms-275)polimorf b - Google Patents
N-(2-aminofenil)-4-[n-(piridin-3-il)-metoksikarbonilaminometil]-benzamid (ms-275)polimorf b Download PDFInfo
- Publication number
- HRP20120183T1 HRP20120183T1 HR20120183T HRP20120183T HRP20120183T1 HR P20120183 T1 HRP20120183 T1 HR P20120183T1 HR 20120183 T HR20120183 T HR 20120183T HR P20120183 T HRP20120183 T HR P20120183T HR P20120183 T1 HRP20120183 T1 HR P20120183T1
- Authority
- HR
- Croatia
- Prior art keywords
- aminophenyl
- benzamide
- pyridin
- methoxycarbonylaminomethyl
- polymorph
- Prior art date
Links
- INVTYAOGFAGBOE-UHFFFAOYSA-N entinostat Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1CNC(=O)OCC1=CC=CN=C1 INVTYAOGFAGBOE-UHFFFAOYSA-N 0.000 title claims abstract 11
- 238000001228 spectrum Methods 0.000 claims abstract 4
- 238000001237 Raman spectrum Methods 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 5
- 239000011541 reaction mixture Substances 0.000 claims 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 230000001461 cytolytic effect Effects 0.000 claims 2
- 231100000433 cytotoxic Toxicity 0.000 claims 2
- 230000001472 cytotoxic effect Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000002244 precipitate Substances 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 208000037896 autoimmune cutaneous disease Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000003610 charcoal Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 claims 1
- 230000024241 parasitism Effects 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
Classifications
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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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4406—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 3, e.g. zimeldine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
-
- 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
- A61P17/06—Antipsoriatics
-
- 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
- A61P17/10—Anti-acne 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
-
- 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
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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
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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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
- A61P37/08—Antiallergic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Abstract
Kristalni N-(2-aminofenil)-4-[N-(piridin-3-il)metoksikarbonilaminometil]-benzamid, polimorf B, formule I naznačen time da njegov difraktogram X-zraka ima refleksiju kod 2 theta = 21.1°, 20.4° i 27.4° i Ramanov spektar ima pojaseve na 902 cm-1, 3063 cm-1, 1639 cm-1 i 916cm-1, a IR (ATR) spektar ima pojaseve na 3309 cm-1, 1702 cm-1, 1638 cm-1, 1260 cm-1 i 749 cm-1, dok IR (KBr) spektar ima pojaseve na 3311 cm-1, 1705 cm-1, 1641 cm-1, 1262 cm-1 i 751 cm-1.Patent sadrži još 6 patentnih zahtjeva.
Claims (7)
1. Kristalni N-(2-aminofenil)-4-[N-(piridin-3-il)metoksikarbonilaminometil]-benzamid, polimorf B, formule I
[image]
naznačen time da njegov difraktogram X-zraka ima refleksiju kod 2 theta = 21.1°, 20.4° i 27.4° i Ramanov spektar ima pojaseve na 902 cm-1, 3063 cm-1, 1639 cm-1 i 916cm-1, a IR (ATR) spektar ima pojaseve na 3309 cm-1, 1702 cm-1, 1638 cm-1, 1260 cm-1 i 749 cm-1, dok IR (KBr) spektar ima pojaseve na 3311 cm-1, 1705 cm-1, 1641 cm-1, 1262 cm-1 i 751 cm-1.
2. Postupak proizvodnje kristalnog N-(2-aminofenil)-4-[N-(piridin-3-il)metoksikarbonilaminometil]-benzamida, polimorfa B spoja formule I
[image]
naznačen time da sadrži korake:
a) sirovi N-(2-aminofenil)-4-[N-(piridin-3-il)metoksikarbonilaminometil]-benzamid je suspendiran u vodi i razrijeđena klorovodična kiselina je dodana u reakcijsku smjesu, kod konstantne unutarnje temperature posude od ispod 5°C, i
b) u navedenu reakcijsku smjesu dodaje se ugljen i reakcijska smjesa se zatim miješa tijekom 1 do 20 sati na temperaturi ispod 5°C, i
c) filtrira se da se iz otopine ukloni ugljen, te se ispire vodom, i
d) uz održavanje unutarnje temperature posude ispod 5°C pH reakcijske smjese se podešava na ≥ 8 sa razrijeđenom otopinom natrijevog hidroksida, i
e) dobiveni istaloženi N-(2-aminofenil)-4-[N-(piridin-3-il)metoksikarbonilaminometil]-benzamid ispire se sa vodom i etanolom, i
f) talog se suspendira u smjesi etanola i vode te se zagrijava do temperature od 40 - 90°C tijekom 1 do 10 sati, te
g) nakon hlađenja smjese, dobiveni talog se ispire sa vodom i etanolom da se dobije čisti N-(2-aminofenil)-4-[N-(piridin-3-il)metoksikarbonilaminometil]-benzamid polimorf B koji se nakon toga suši na temperaturi između 30-60 °C.
3. Postupak prema zahtjevu 2, naznačen time da se korak b) i korak c) ponavljaju ako nakon koraka c) nije dovoljno visoka čistoća N-(2-aminofenil)-4-[N-(piridin-3-il)metoksikarbonilaminometil]-benzamida.
4. Uporaba N-(2-aminofenil)-4-[N-(piridin-3-il)metoksikarbonilaminometil]benzamid polimorfa B, naznačena time da se odnosi na proizvodnju lijeka za liječenje malignih tumora, autoimunih bolesti, kožnih bolesti i parazitizama.
5. Pripravak naznačen time da sadrži N-(2-aminofenil)-4-[N-(piridin-3-il)metoksikarbonilaminometil]-benzamid polimorf B samostalno ili u kombinaciji s farmaceutski prihvatljivim razrjeđivačem i/ili nosačem.
6. Kombinacija naznačena time da sadrži N-(2-aminofenil)-4-[N-(piridin-3-il)metoksikarbonilaminometil]-benzamid polimorf B zajedno s jednim ili više citotoksičnih ili citolitičkih sredstava.
7. Kombinacija prema zahtjevu 6, naznačena time da je N-(2-aminofenil)-4-[N-(piridin-3-il)metoksi-karbonilaminometil]-benzamid polimorf B namijenjen za istovremeno, odvojeno ili sekvencijalno davanje zajedno sa citotoksičnim ili citolitičkim sredstvima.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9304608P | 2008-08-29 | 2008-08-29 | |
| EP08163274 | 2008-08-29 | ||
| PCT/EP2009/006381 WO2010022988A1 (en) | 2008-08-29 | 2009-08-27 | N-(2-aminophenyl)-4-[n-(pyridine-3-yl)-methoxycarbonyl-aminomethyl]-benzamide (ms-275)polymorph b |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HRP20120183T1 true HRP20120183T1 (hr) | 2012-03-31 |
| HRP20120183T8 HRP20120183T8 (en) | 2012-11-30 |
Family
ID=41133825
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20120183AT HRP20120183T8 (en) | 2008-08-29 | 2012-02-24 | N-(2-aminophenyl)-4-[n-(pyridine-3-yl)-methoxycarbonyl-aminomethyl]-benzamide (ms-275)polymorph b |
Country Status (36)
| Country | Link |
|---|---|
| US (2) | US7973166B2 (hr) |
| EP (1) | EP2350005B1 (hr) |
| JP (1) | JP4921616B2 (hr) |
| KR (1) | KR101073760B1 (hr) |
| CN (1) | CN102137846B (hr) |
| AR (1) | AR073226A1 (hr) |
| AT (1) | ATE538094T1 (hr) |
| AU (1) | AU2009286982C1 (hr) |
| BR (1) | BRPI0918580B8 (hr) |
| CA (1) | CA2735294C (hr) |
| CO (1) | CO6351736A2 (hr) |
| CR (2) | CR20110107A (hr) |
| CY (1) | CY1112645T1 (hr) |
| DK (1) | DK2350005T3 (hr) |
| DO (1) | DOP2011000064A (hr) |
| EA (1) | EA016811B1 (hr) |
| EC (1) | ECSP11010849A (hr) |
| ES (1) | ES2378640T3 (hr) |
| HK (1) | HK1160107A1 (hr) |
| HN (1) | HN2011000609A (hr) |
| HR (1) | HRP20120183T8 (hr) |
| IL (1) | IL211276A (hr) |
| MA (1) | MA32610B1 (hr) |
| MX (1) | MX2011002248A (hr) |
| MY (1) | MY149058A (hr) |
| NZ (1) | NZ591387A (hr) |
| PE (2) | PE20141062A1 (hr) |
| PL (1) | PL2350005T3 (hr) |
| PT (1) | PT2350005E (hr) |
| RS (1) | RS52164B (hr) |
| SI (1) | SI2350005T1 (hr) |
| SM (1) | SMT201200026B (hr) |
| SV (1) | SV2011003846A (hr) |
| TW (1) | TWI427062B (hr) |
| WO (1) | WO2010022988A1 (hr) |
| ZA (1) | ZA201102285B (hr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK2350005T3 (da) | 2008-08-29 | 2012-03-19 | Bayer Pharma AG | N-(2-aminophenyl)-4-[N-(pyridin-3-yl)-methoxy-carbonyl-aminomehtyl]benzamid(MS-275)-polymorf B |
| US8221753B2 (en) | 2009-09-30 | 2012-07-17 | Tracon Pharmaceuticals, Inc. | Endoglin antibodies |
| FR2977492B1 (fr) * | 2011-07-04 | 2013-07-05 | Servier Lab | Nouvelle association entre le n-hydroxy-4-{2-[3-(n,n-dimethylaminomethyl) benzofuran-2-ylcarbonylamino]ethoxy}benzamide et le folfox |
| UA115789C2 (uk) | 2012-09-05 | 2017-12-26 | Трейкон Фармасутікалз, Інк. | Композиція антитіла до cd105 та її застосування |
| JP2017537084A (ja) | 2014-11-12 | 2017-12-14 | トラコン ファーマシューティカルズ、インコーポレイテッド | 抗エンドグリン抗体及びその用途 |
| US9926375B2 (en) | 2014-11-12 | 2018-03-27 | Tracon Pharmaceuticals, Inc. | Anti-endoglin antibodies and uses thereof |
| EP3168210A1 (en) | 2015-11-13 | 2017-05-17 | Sandoz Ag | Crystalline forms of entinostat |
| WO2017216761A1 (en) * | 2016-06-17 | 2017-12-21 | Dr. Reddy's Laboratories Limited | Solid forms of entinostat |
| WO2019019130A1 (zh) * | 2017-07-28 | 2019-01-31 | 杭州领业医药科技有限公司 | 含恩替诺特的化合物，其化合物晶型及其制备方法和药物组合物 |
| KR20240019100A (ko) | 2021-05-10 | 2024-02-14 | 맥파란 스미스 리미티드 | 엔티노스타트의 신규 형태 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6174905B1 (en) * | 1996-09-30 | 2001-01-16 | Mitsui Chemicals, Inc. | Cell differentiation inducer |
| JP3354090B2 (ja) * | 1996-09-30 | 2002-12-09 | シエーリング アクチエンゲゼルシャフト | 分化誘導剤 |
| JP4030683B2 (ja) * | 1998-07-24 | 2008-01-09 | 三井化学株式会社 | ベンズアミド誘導体の合成法 |
| US6320078B1 (en) * | 1998-07-24 | 2001-11-20 | Mitsui Chemicals, Inc. | Method of producing benzamide derivatives |
| JP2001064177A (ja) * | 1999-08-16 | 2001-03-13 | Schering Ag | ベンズアミド誘導体を有効成分とする製剤 |
| JP4360660B2 (ja) * | 1999-11-09 | 2009-11-11 | 三井化学株式会社 | モノアシルフェニレンジアミン誘導体の精製法 |
| PE20050206A1 (es) * | 2003-05-26 | 2005-03-26 | Schering Ag | Composicion farmaceutica que contiene un inhibidor de histona deacetilasa |
| DK2350005T3 (da) | 2008-08-29 | 2012-03-19 | Bayer Pharma AG | N-(2-aminophenyl)-4-[N-(pyridin-3-yl)-methoxy-carbonyl-aminomehtyl]benzamid(MS-275)-polymorf B |
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2009
- 2009-08-27 DK DK09778301T patent/DK2350005T3/da active
- 2009-08-27 CN CN200980134057.8A patent/CN102137846B/zh active Active
- 2009-08-27 MY MYPI2011000789A patent/MY149058A/en unknown
- 2009-08-27 PL PL09778301T patent/PL2350005T3/pl unknown
- 2009-08-27 KR KR1020117007131A patent/KR101073760B1/ko active IP Right Review Request
- 2009-08-27 PE PE2014000099A patent/PE20141062A1/es not_active Application Discontinuation
- 2009-08-27 ES ES09778301T patent/ES2378640T3/es active Active
- 2009-08-27 AT AT09778301T patent/ATE538094T1/de active
- 2009-08-27 SI SI200930182T patent/SI2350005T1/sl unknown
- 2009-08-27 AU AU2009286982A patent/AU2009286982C1/en active Active
- 2009-08-27 EA EA201100354A patent/EA016811B1/ru active IP Right Grant
- 2009-08-27 WO PCT/EP2009/006381 patent/WO2010022988A1/en active Application Filing
- 2009-08-27 JP JP2011524272A patent/JP4921616B2/ja active Active
- 2009-08-27 PE PE2011000218A patent/PE20110677A1/es not_active Application Discontinuation
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- 2009-08-27 BR BRPI0918580A patent/BRPI0918580B8/pt active IP Right Grant
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- 2009-08-27 EP EP20090778301 patent/EP2350005B1/en active Active
- 2009-08-28 AR ARP090103317 patent/AR073226A1/es unknown
- 2009-08-28 TW TW098129170A patent/TWI427062B/zh active
- 2009-08-28 US US12/549,458 patent/US7973166B2/en not_active Ceased
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- 2011-02-17 IL IL211276A patent/IL211276A/en active IP Right Grant
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- 2011-02-28 DO DO2011000064A patent/DOP2011000064A/es unknown
- 2011-02-28 EC ECSP11010849 patent/ECSP11010849A/es unknown
- 2011-02-28 CO CO11024240A patent/CO6351736A2/es unknown
- 2011-02-28 HN HN2011000609A patent/HN2011000609A/es unknown
- 2011-03-04 MA MA33670A patent/MA32610B1/fr unknown
- 2011-03-28 ZA ZA2011/02285A patent/ZA201102285B/en unknown
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2012
- 2012-01-11 HK HK12100290.3A patent/HK1160107A1/xx unknown
- 2012-02-24 HR HRP20120183AT patent/HRP20120183T8/hr unknown
- 2012-03-20 CY CY20121100293T patent/CY1112645T1/el unknown
- 2012-06-01 SM SM201200026T patent/SMT201200026B/it unknown
-
2014
- 2014-03-07 US US14/201,684 patent/USRE45499E1/en active Active
-
2016
- 2016-08-27 CR CR20160465A patent/CR20160465A/es unknown
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