HRP20131128T1 - Kristalni oblik (e) 4-[[4-[[4-(2-cijanoetenil)-2,6-dimetilfenil]amino]-2-pirimidinil]amino]benzonitrila - Google Patents
Kristalni oblik (e) 4-[[4-[[4-(2-cijanoetenil)-2,6-dimetilfenil]amino]-2-pirimidinil]amino]benzonitrila Download PDFInfo
- Publication number
- HRP20131128T1 HRP20131128T1 HRP20131128AT HRP20131128T HRP20131128T1 HR P20131128 T1 HRP20131128 T1 HR P20131128T1 HR P20131128A T HRP20131128A T HR P20131128AT HR P20131128 T HRP20131128 T HR P20131128T HR P20131128 T1 HRP20131128 T1 HR P20131128T1
- Authority
- HR
- Croatia
- Prior art keywords
- amino
- cyanoethenyl
- dimethylphenyl
- pyrimidinyl
- benzonitrile
- Prior art date
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- YIBOMRUWOWDFLG-ONEGZZNKSA-N rilpivirine Chemical compound CC1=CC(\C=C\C#N)=CC(C)=C1NC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 YIBOMRUWOWDFLG-ONEGZZNKSA-N 0.000 title claims 14
- 238000002360 preparation method Methods 0.000 claims 15
- 239000011859 microparticle Substances 0.000 claims 14
- 239000002105 nanoparticle Substances 0.000 claims 14
- 239000000825 pharmaceutical preparation Substances 0.000 claims 5
- 239000003607 modifier Substances 0.000 claims 4
- 239000007787 solid Substances 0.000 claims 4
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims 2
- YIBOMRUWOWDFLG-UHFFFAOYSA-N 4-[[4-[4-(2-cyanoethenyl)-2,6-dimethylanilino]pyrimidin-2-yl]amino]benzonitrile Chemical compound CC1=CC(C=CC#N)=CC(C)=C1NC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 YIBOMRUWOWDFLG-UHFFFAOYSA-N 0.000 claims 2
- 208000031886 HIV Infections Diseases 0.000 claims 2
- 208000037357 HIV infectious disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000002245 particle Substances 0.000 claims 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 230000005855 radiation Effects 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- 239000000080 wetting agent Substances 0.000 claims 2
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical group C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- 229920001214 Polysorbate 60 Polymers 0.000 claims 1
- 229930003427 Vitamin E Natural products 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 239000008365 aqueous carrier Substances 0.000 claims 1
- 239000006172 buffering agent Substances 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000007884 disintegrant Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229930195729 fatty acid Natural products 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- -1 fatty acid ester Chemical class 0.000 claims 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 238000010255 intramuscular injection Methods 0.000 claims 1
- 239000007927 intramuscular injection Substances 0.000 claims 1
- 239000007951 isotonicity adjuster Substances 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 239000000314 lubricant Substances 0.000 claims 1
- 230000000873 masking effect Effects 0.000 claims 1
- 238000005259 measurement Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 150000003904 phospholipids Chemical class 0.000 claims 1
- 210000002381 plasma Anatomy 0.000 claims 1
- 229960000502 poloxamer Drugs 0.000 claims 1
- 229920001983 poloxamer Polymers 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 239000003755 preservative agent Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 238000010254 subcutaneous injection Methods 0.000 claims 1
- 239000007929 subcutaneous injection Substances 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 1
- 229940046009 vitamin E Drugs 0.000 claims 1
- 235000019165 vitamin E Nutrition 0.000 claims 1
- 239000011709 vitamin E Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 239000008215 water for injection Substances 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Virology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Claims (23)
1. Polimorf I (E) 4-[[4-[[4-(2-cijanoetenil)-2,6-dimetilfenil]amino]2-pirimidinil]amino]benzonitrila, naznačen time da ima vrške difrakcije X-zraka na prahu na položajima dva-theta 9.0°± 0.2°, 14.3°± 0.2°, 17.1°± 0.2° i 24.2°± 0.2° mjereno na Philips X'PertPRO MPD difraktometru PW3050/60 sa generatorom PW3040 sa slijedećim parametrima instrumenta:
napon generatora: 45 kV
struja generatora: 40 mA
geometrija: Bragg-Brentano
nosač uzorka: rotator
uz slijedeće uvjete mjerenja:
način skeniranja: kontinuirano
raspon skeniranja: 3 do 50° 2θ
veličina koraka: 0.01675°/korak
vrijeme odbrojavanja: 60.59 sek/korak
vrijeme okreta: 1 sek
vrsta zračenja: CuKα
valna duljina zračenja: 1.54056 Å
Putanja upadne zrake Putanja difrakcijske zrake
program. divergentni otvor: 15 mm dugi štit protiv raspršenja: +
Sollerova pukotina: 0.04 rad Sollerova pukotina: 0.04 rad
maskiranje zrake: 15 mm Ni filter: +
pukotina protiv raspršenja: 1° detektor: X'Celerator
nož za usmjeravanje zrake +
2. Polimorf prema zahtjevu 1 koji je nadalje naznačen time da ima vrške difrakcije X-zraka na prahu na položajima dva-theta 11.3°± 0.2°, 19.1°± 0.2°, i 27.6°± 0.2°.
3. Postupak za dobivanje polimorfa prema zahtjevu 1 ili 2, naznačen time da se navedeni polimorf dobiva otapanjem (E) 4-[[4-[[4-(2-cijanoetenil)-2,6-dimetilfenil]-amino]-2-pirimidinil]amino]benzonitrila u ketonu i zagrijavanja otopine do temperature refluksa, te ostavljanja otopine da se ohladi.
4. Čvrsti farmaceutski pripravak naznačen time da kao aktivnu tvar sadrži polimorf I (E) 4-[[4-[[4-(2-cijanoetenil)-2,6-dimetilfenil]amino]-2-pirimidinil]amino]benzonitrila prema zahtjevu 1 ili 2 i farmaceutski prihvatljiv nosač.
5. Farmaceutski pripravak mikro- ili nanočestica za davanje putem intramuskularne ili potkožne injekcije, naznačen time da sadrži terapeutski učinkovitu količinu polimorfa I (E) 4-[[4-[[4-(2-cijanoetenil)-2,6-dimetilfenil]-amino]-2-pirimidinil]amino]benzonitrila prema zahtjevu 1 ili 2, koji sadrži navedeni polimorf I (E) 4-[[4-[[4-(2-cijanoetenil)-2,6-dimetilfenil]amino]-2-pirimidinil]amino]benzonitrila, u obliku mikro- ili nanočestica, sa modifikatorom površine adsorbiranim na njegovu površinu, koji je suspendiran u farmaceutski prihvatljivom vodenom nosaču.
6. Pripravak mikro- ili nano-čestica kako je definirano u zahtjevu 5 naznačen time da je modifikator površine odabran od poloksamera, α-tokoferil polietilen glikol sukcinata, estera polioksietilen sorbitan masne kiseline, te soli negativno nabijenih fosfolipida ili njihovog kiselog oblika.
7. Pripravak mikro- ili nano-čestica kako je definirano u zahtjevu 6 naznačen time da je modifikator površine odabran od Pluronic™ F108, Vitamin E TGPS, Tween™ 80, i Lipoid™ EPG.
8. Pripravak od mikro- ili nano-čestica kako je definirano u zahtjevu 7 naznačen time da je modifikator površine Pluronic™ F108.
9. Pripravak mikro- ili nano-čestica kako je definirano u bilo kojem zahtjevu od 5 do 8 naznačen time da je prosječna veličina čestica mikro- ili nano-čestica polimorfa I (E) 4-[[4-[[4-(2-cijanoetenil)-2,6-dimetilfenil] amino]-2-pirimidinil]amino]benzonitrila u rasponu od oko 50 nm do oko 500 nm.
10. Pripravak mikro- ili nano-čestica kako je definirano u zahtjevu 9 naznačen time da je prosječna veličina čestica mikro- ili nano-čestica polimorfa I (E) 4-[[4-[[4-(2-cijanoetenil)-2,6-dimetilfenil]amino]-2-pirimidinil]amino]benzonitrila u rasponu od oko 100 nm do oko 250 nm.
11. Pripravak mikro- ili nano-čestica kako je definirano u bilo kojem zahtjevu od 5 do 10 naznačen time da se terapeutski učinkovita količina polimorfa I (E) 4-[[4-[[4-(2-cijanoetenil)-2,6-dimetilfenil]amino]-2-pirimidinil]amino]benzonitrila računa na temelju doze (E) 4-[[4-[[4-(2-cijanoetenil)-2,6-dimetilfenil]amino]-2-pirimidinil]amino]benzonitrila u rasponu od 0.5 mg/dan do oko 50 mg/dan.
12. Pripravak mikro- ili nano-čestica kako je definirano u bilo kojem zahtjevu od 5 do 11 naznačen time da se terapeutski učinkovita količina polimorfa I (E) 4-[[4-[[4-(2-cijanoetenil)-2,6-dimetilfenil]amino]-2-pirimidinil]amino]benzonitrila is računa na temelju doze (E) 4-[[4-[[4-(2-cijanoetenil)-2,6-dimetilfenil]amino]-2-pirimidinil]amino]benzonitril u rasponu od oko 5 mg/dan do oko 50 mg/dan.
13. Pripravak mikro- ili nano-čestica kako je definirano u zahtjevu 5 naznačen time da sadrži težinske udjele, na temelju ukupnog volumena pripravka:
(a) od 3% do 50% (w/v), ili od 10% do 40% (w/v), ili od 10% do 30% (w/v), polimorfa I (E) 4-[[4-[[4-(2-cijanoetenil)-2,6-dimetilfenil]amino]-2-pirimidinil]amino]benzonitrila;
(b) od 0.5% do 10 %, ili od 0.5% do 2% (w/v) sredstva za vlaženje;
(c) od 0% do 10%, ili od 0% do 5%, ili od 0% do 2%, ili od 0% do 1% jednog ili više puferskih sredstava;
(d) od 0% do 10 %, ili od 0% do 6% (w/v) izotoničkog sredstva
(e) od 0% do 2% (w/v) konzervansa; i
(f) vodu za injekcije q.s. do 100%.
14. Upotreba pripravka mikro- ili nano-čestica kako je definirano u bilo kojem zahtjevu od 5 do 13 naznačena time da je za proizvodnju medikamenta za liječenje HIV infekcije.
15. Upotreba pripravka od mikro- ili nano-čestica kako je definirano u bilo kojem zahtjevu od 5 do 13, naznačena time da je za proizvodnju medikamenta za sprječavanje HIV infekcije kod subjekta koji ima rizik od zaraze sa HIV-om.
16. Upotreba prema zahtjevu 14 ili 15, naznačena time da se pripravak daje ili se treba primjenjivati povremeno u vremenskom intervalu koji je u rasponu od jednog tjedna do jedne godine, ili u rasponu od jednog tjedna do dvije godine.
17. Upotreba prema zahtjevu 14 ili 15, naznačena time da se pripravak daje ili se treba primjenjivati povremeno u vremenskom intervalu koji je u rasponu od jednog tjedna do jednog mjeseca, ili je u rasponu od jednog mjeseca do tri mjeseca, ili je u rasponu od tri mjeseca do šest mjeseci.
18. Upotreba prema zahtjevu 17 naznačena time da se pripravak daje ili se treba primjenjivati povremeno jednom mjesečno.
19. Upotreba prema zahtjevu 17 naznačena time da se pripravak daje ili se treba primjenjivati povremeno jednom svaka tri mjeseca.
20. Upotreba prema zahtjevu 14 ili 15 naznačena time da se učinkovita količina polimorfa I (E) 4-[[4-[[4-(2-cijanoetenil)-2,6-dimetilfenil]amino]-2-pirimidinil]amino]benzonitrila u pripravku odabire tako da se koncentracija (E) 4-[[4-[[4-(2-cijanoetenil)-2,6-dimetilfenil]amino]-2-pirimidinil]amino]benzonitrila u krvnoj plazmi održava na razini koja je u rasponu od oko 20 ng/ml do oko 90 ng/ml.
21. Čvrsti farmaceutski pripravak prema zahtjevu 4 naznačen time da je u obliku tablete ili kapsule.
22. Čvrsti farmaceutski pripravak prema zahtjevu 21 naznačen time da sadrži od oko 25 mg do oko 150 mg polimorfa I (E) 4-[[4-[[4-(2-cijanoetenil)-2,6-dimetilfenil] amino]-2-pirimidinil]amino]benzonitrila.
23. Čvrsti farmaceutski pripravak prema zahtjevu 4 naznačen time da sadrži:
(a) od 5 do 50% polimorfa I od (E) 4-[[4-[[4-(2-cijanoetenil)-2,6-dimetilfenil]amino]-2-pirimidinil]amino]benzonitril;
(b) od 0.01 do 5% sredstva za vlaženje;
(c) od 40 do 92% razrjeđivača;
(d) od 0 do 10% polimera;
(e) od 2 do 10% dezintegratora;
(f) od 0.1 do 5% glidanta;
(g) od 0.1 do 1.5% lubrikanta.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07112392 | 2007-07-12 | ||
| PCT/EP2008/059054 WO2009007441A2 (en) | 2007-07-12 | 2008-07-11 | Crystalline form of (e) 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2 pyrimidinyl]amino]benzonitrile |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20131128T1 true HRP20131128T1 (hr) | 2013-12-20 |
Family
ID=38706528
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20131128AT HRP20131128T1 (hr) | 2007-07-12 | 2013-11-26 | Kristalni oblik (e) 4-[[4-[[4-(2-cijanoetenil)-2,6-dimetilfenil]amino]-2-pirimidinil]amino]benzonitrila |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8426434B2 (hr) |
| EP (1) | EP2175857B1 (hr) |
| JP (1) | JP5701057B2 (hr) |
| CN (1) | CN101743006B (hr) |
| AU (1) | AU2008274185B2 (hr) |
| BR (1) | BRPI0814548A2 (hr) |
| CA (1) | CA2693044C (hr) |
| DK (1) | DK2175857T3 (hr) |
| ES (1) | ES2437331T3 (hr) |
| HK (1) | HK1144669A1 (hr) |
| HR (1) | HRP20131128T1 (hr) |
| IL (1) | IL202363A (hr) |
| RU (1) | RU2498979C2 (hr) |
| SI (1) | SI2175857T1 (hr) |
| WO (1) | WO2009007441A2 (hr) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY169670A (en) | 2003-09-03 | 2019-05-08 | Tibotec Pharm Ltd | Combinations of a pyrimidine containing nnrti with rt inhibitors |
| TWI494133B (zh) | 2007-03-14 | 2015-08-01 | Tibotec Pharm Ltd | 重組用粉末 |
| ES2530941T3 (es) * | 2009-09-22 | 2015-03-09 | Janssen Sciences Ireland Uc | Tratamiento y prevención de infección por el VIH |
| US20120295898A1 (en) * | 2010-01-27 | 2012-11-22 | Mark Richard Underwood | Antiviral Therapy |
| TWI577377B (zh) * | 2010-09-16 | 2017-04-11 | Ｖｉｉｖ醫療保健公司 | 醫藥組合物 |
| WO2012125993A1 (en) | 2011-03-17 | 2012-09-20 | Teva Pharmaceutical Industries Ltd. | Solid state forms of rilpivirine base, and rilipivirine salts |
| CN108210469A (zh) | 2011-04-15 | 2018-06-29 | 詹森药业有限公司 | 冻干药物纳米混悬剂 |
| EP2604593A1 (en) * | 2011-12-14 | 2013-06-19 | Sandoz AG | Polymorph of Rilpivirine hydrochloride and its use as antiviral |
| EP2628732A1 (en) * | 2012-02-20 | 2013-08-21 | Sandoz AG | Novel crystalline form of rilpivirine hydrochloride |
| WO2013087794A1 (en) * | 2011-12-14 | 2013-06-20 | Sandoz Ag | Polymorph of rilpivirine hydrochloride and its use as antiviral |
| EA201590862A1 (ru) * | 2012-12-14 | 2016-05-31 | ГЛАКСОСМИТКЛАЙН ЭлЭлСи | Фармацевтические композиции |
| CZ2015579A3 (cs) | 2015-08-27 | 2017-03-08 | Zentiva, K.S. | Krystalická forma A Rilpivirin Adipátu a způsob její přípravy |
| FI3597646T3 (fi) | 2016-08-19 | 2023-09-07 | Gilead Sciences Inc | Hi-virusinfektion profylaktiseen tai terapeuttiseen hoitoon käyttökelpoisia terapeuttisia yhdisteitä |
| CN115397422A (zh) | 2019-11-29 | 2022-11-25 | 西皮欧生命科学有限公司 | 包含利匹韦林的组合物和其用于治疗肿瘤或癌症的用途 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5145684A (en) | 1991-01-25 | 1992-09-08 | Sterling Drug Inc. | Surface modified drug nanoparticles |
| JO3429B1 (ar) * | 2001-08-13 | 2019-10-20 | Janssen Pharmaceutica Nv | مشتقات برميدينات مثبطة فيروس الايدز |
| CA2493794C (en) | 2002-08-09 | 2010-05-25 | Janssen Pharmaceutica N.V. | Processes for the preparation of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile |
| NZ540321A (en) | 2002-11-15 | 2007-09-28 | Tibotec Pharm Ltd | Substituted indolepyridinium as anti-infective compounds |
| AU2005279158C1 (en) | 2004-09-02 | 2010-12-16 | Janssen Pharmaceutica N.V. | Hydrochloride of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl] amino]benzonitrile |
| BRPI0609299A2 (pt) * | 2005-04-13 | 2010-03-23 | Pfizer Prod Inc | formulaÇÕes de depàsito injetÁveis e mÉtodos para proporcionar liberaÇço sustentada de composiÇÕes de nanopartÍculas |
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2008
- 2008-07-11 EP EP08786055.7A patent/EP2175857B1/en active Active
- 2008-07-11 WO PCT/EP2008/059054 patent/WO2009007441A2/en active Application Filing
- 2008-07-11 DK DK08786055.7T patent/DK2175857T3/da active
- 2008-07-11 SI SI200831105T patent/SI2175857T1/sl unknown
- 2008-07-11 AU AU2008274185A patent/AU2008274185B2/en active Active
- 2008-07-11 JP JP2010515519A patent/JP5701057B2/ja active Active
- 2008-07-11 ES ES08786055.7T patent/ES2437331T3/es active Active
- 2008-07-11 US US12/668,079 patent/US8426434B2/en active Active
- 2008-07-11 CA CA2693044A patent/CA2693044C/en active Active
- 2008-07-11 RU RU2010104848/04A patent/RU2498979C2/ru active
- 2008-07-11 BR BRPI0814548-2A2A patent/BRPI0814548A2/pt not_active Application Discontinuation
- 2008-07-11 CN CN2008800243222A patent/CN101743006B/zh active Active
-
2009
- 2009-11-26 IL IL202363A patent/IL202363A/en active IP Right Grant
-
2010
- 2010-12-08 HK HK10111404.5A patent/HK1144669A1/xx unknown
-
2013
- 2013-11-26 HR HRP20131128AT patent/HRP20131128T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HK1144669A1 (hr) | 2011-03-04 |
| IL202363A (en) | 2016-04-21 |
| DK2175857T3 (da) | 2013-12-02 |
| WO2009007441A3 (en) | 2009-04-30 |
| JP2010533148A (ja) | 2010-10-21 |
| BRPI0814548A2 (pt) | 2015-01-06 |
| SI2175857T1 (sl) | 2014-01-31 |
| WO2009007441A2 (en) | 2009-01-15 |
| CN101743006B (zh) | 2013-09-11 |
| CA2693044A1 (en) | 2009-01-15 |
| US20100189796A1 (en) | 2010-07-29 |
| AU2008274185B2 (en) | 2014-07-03 |
| JP5701057B2 (ja) | 2015-04-15 |
| IL202363A0 (en) | 2010-06-30 |
| CN101743006A (zh) | 2010-06-16 |
| AU2008274185A1 (en) | 2009-01-15 |
| CA2693044C (en) | 2017-03-14 |
| ES2437331T3 (es) | 2014-01-10 |
| EP2175857B1 (en) | 2013-09-11 |
| RU2498979C2 (ru) | 2013-11-20 |
| EP2175857A2 (en) | 2010-04-21 |
| US8426434B2 (en) | 2013-04-23 |
| RU2010104848A (ru) | 2011-08-20 |
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