CA2658843A1 - Crystalline antifungal compounds - Google Patents
Crystalline antifungal compounds Download PDFInfo
- Publication number
- CA2658843A1 CA2658843A1 CA002658843A CA2658843A CA2658843A1 CA 2658843 A1 CA2658843 A1 CA 2658843A1 CA 002658843 A CA002658843 A CA 002658843A CA 2658843 A CA2658843 A CA 2658843A CA 2658843 A1 CA2658843 A1 CA 2658843A1
- Authority
- CA
- Canada
- Prior art keywords
- chloro
- methyl
- hydroxy
- difluorophenyl
- triazol
- 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.)
- Abandoned
Links
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- 230000000843 anti-fungal effect Effects 0.000 title description 4
- 229940121375 antifungal agent Drugs 0.000 title description 4
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- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 claims description 352
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- 238000000634 powder X-ray diffraction Methods 0.000 claims description 189
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 183
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- -1 (1R,2R)-7-chloro-3-[2-(2,4-difluorophenyl)-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]quinazolin-4(3H)-one Chemical compound 0.000 claims description 20
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- 235000019366 oxytetracycline Nutrition 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
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- 239000001814 pectin Chemical class 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
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- 229920005862 polyol Polymers 0.000 description 1
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- 229920002223 polystyrene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- ZQDXEVWNBNDLPI-UHFFFAOYSA-N pyrido[3,4-e][1,2,4]triazine Chemical compound N1=CN=C2C=NC=CC2=N1 ZQDXEVWNBNDLPI-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 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 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
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- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
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- 229950005137 saperconazole Drugs 0.000 description 1
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- 238000013515 script Methods 0.000 description 1
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- 229940083542 sodium Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Chemical class 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- XNRNJIIJLOFJEK-UHFFFAOYSA-N sodium;1-oxidopyridine-2-thione Chemical compound [Na+].[O-]N1C=CC=CC1=S XNRNJIIJLOFJEK-UHFFFAOYSA-N 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
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- 229940075582 sorbic acid Drugs 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000003351 stiffener Substances 0.000 description 1
- 229960002607 sulconazole Drugs 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940111630 tea tree oil Drugs 0.000 description 1
- 239000010677 tea tree oil Substances 0.000 description 1
- 229960002722 terbinafine Drugs 0.000 description 1
- DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 description 1
- 229960000580 terconazole Drugs 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 201000003875 tinea corporis Diseases 0.000 description 1
- 201000004647 tinea pedis Diseases 0.000 description 1
- 229960004214 tioconazole Drugs 0.000 description 1
- 229960004880 tolnaftate Drugs 0.000 description 1
- FUSNMLFNXJSCDI-UHFFFAOYSA-N tolnaftate Chemical compound C=1C=C2C=CC=CC2=CC=1OC(=S)N(C)C1=CC=CC(C)=C1 FUSNMLFNXJSCDI-UHFFFAOYSA-N 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- GZXOHHPYODFEGO-UHFFFAOYSA-N triglycine sulfate Chemical class NCC(O)=O.NCC(O)=O.NCC(O)=O.OS(O)(=O)=O GZXOHHPYODFEGO-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 229940025707 vaginal product Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- BCEHBSKCWLPMDN-MGPLVRAMSA-N voriconazole Chemical compound C1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=NC=C1F BCEHBSKCWLPMDN-MGPLVRAMSA-N 0.000 description 1
- 229960004740 voriconazole Drugs 0.000 description 1
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- 230000036642 wellbeing Effects 0.000 description 1
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- 235000010493 xanthan gum Nutrition 0.000 description 1
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- 229940082509 xanthan gum Drugs 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/90—Oxygen atoms with acyclic radicals attached in position 2 or 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
- A61P31/10—Antimycotics
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83586306P | 2006-08-07 | 2006-08-07 | |
| EP06380225A EP1887004A1 (en) | 2006-08-07 | 2006-08-07 | Crystalline forms of (1R,2R)-7-Chloro-3-[2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]quinazolin-4(3H)-one |
| US60/835,863 | 2006-08-07 | ||
| EP06380225.0 | 2006-08-07 | ||
| US92940807P | 2007-06-26 | 2007-06-26 | |
| US60/929,408 | 2007-06-26 | ||
| EP07380186.2 | 2007-06-26 | ||
| EP07380186A EP2009009A1 (en) | 2007-06-26 | 2007-06-26 | Crystalline antifungal compounds |
| PCT/US2007/017476 WO2008021049A2 (en) | 2006-08-07 | 2007-08-06 | Crystalline antifungal compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2658843A1 true CA2658843A1 (en) | 2008-02-21 |
Family
ID=39082545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002658843A Abandoned CA2658843A1 (en) | 2006-08-07 | 2007-08-06 | Crystalline antifungal compounds |
Country Status (17)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006018853A2 (en) | 2004-08-19 | 2006-02-23 | Hetero Drugs Limited | Novel polymorphs of efavirenz |
| TWI363058B (en) * | 2006-04-05 | 2012-05-01 | Opko Health Inc | Hydrochloride salts of 8-[{1-(3,5-bis-(trifluoromethyl)phenyl)-ethoxy}-methyl]-8-phenyl-1,7-diaza-spiro[4.5]decan-2-one and preparation process therefor |
| ITMI20062449A1 (it) * | 2006-12-19 | 2008-06-20 | Dipharma Spa | Forma cristallina di rabeprazolo sodico |
| AU2010254064B2 (en) * | 2009-05-29 | 2015-01-22 | Palau Pharma, S.L.U | Azole antifungal compositions |
| KR20120079054A (ko) * | 2009-07-10 | 2012-07-11 | 에볼바 아게 | 디인 조성물 |
| EP2464230B1 (en) * | 2009-08-14 | 2016-10-05 | OPKO Health, Inc. | Intravenous formulations of rolapitant |
| US9435692B2 (en) | 2014-02-05 | 2016-09-06 | Lam Research Corporation | Calculating power input to an array of thermal control elements to achieve a two-dimensional temperature output |
| US11039620B2 (en) | 2014-02-19 | 2021-06-22 | Corning Incorporated | Antimicrobial glass compositions, glasses and polymeric articles incorporating the same |
| US11039621B2 (en) | 2014-02-19 | 2021-06-22 | Corning Incorporated | Antimicrobial glass compositions, glasses and polymeric articles incorporating the same |
| US9622483B2 (en) | 2014-02-19 | 2017-04-18 | Corning Incorporated | Antimicrobial glass compositions, glasses and polymeric articles incorporating the same |
| GB201410407D0 (en) * | 2014-06-11 | 2014-07-23 | Univ Dundee And Syngene Internat Ltd Plc And Consejo Superior De Investigaciones Cientificas And Med | Treatment of chagas disease |
| EA025187B1 (ru) * | 2015-04-17 | 2016-11-30 | Тагир Аббасели оглы Сулейманов | Производное дитиокарбамата 2-((4-(4-метилпиперазин-1-ил)фенил)амино)-2-оксоетил4-этилпиперазин-1-карбодитиоат, обладающее антифунгальной активностью |
| CN118695852A (zh) | 2021-12-22 | 2024-09-24 | 帕劳制药有限公司 | 多颗粒阿巴康唑组合物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0293500A1 (en) | 1987-06-01 | 1988-12-07 | American Cyanamid Company | 3-heteroalkyl-2,4.quinzaoline-diones |
| GB8819308D0 (en) | 1988-08-13 | 1988-09-14 | Pfizer Ltd | Triazole antifungal agents |
| TW218017B (cg-RX-API-DMAC10.html) | 1992-04-28 | 1993-12-21 | Takeda Pharm Industry Co Ltd | |
| TW297813B (cg-RX-API-DMAC10.html) * | 1993-09-24 | 1997-02-11 | Takeda Pharm Industry Co Ltd | |
| CA2134417A1 (en) * | 1993-12-22 | 1995-06-23 | Katsumi Itoh | Optically active azole derivatives, their production and use |
| MX9702382A (es) * | 1995-08-02 | 1998-02-28 | Uriach & Cia Sa J | Nuevos derivados de pirimidona con actividad antifungica. |
| WO1998039305A1 (en) * | 1997-03-05 | 1998-09-11 | Takeda Chemical Industries, Ltd. | Crystalline form of a bis 1,2,4-triazole compound |
| ES2159488B1 (es) * | 2000-03-07 | 2002-04-16 | Uriach & Cia Sa J | Procedimiento para la preparacion de derivados de pirimidona con actividad antifungica. |
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2007
- 2007-08-06 EP EP20070836538 patent/EP2049504A4/en not_active Withdrawn
- 2007-08-06 EP EP13167750.2A patent/EP2650291B1/en active Active
- 2007-08-06 AU AU2007284851A patent/AU2007284851B2/en not_active Ceased
- 2007-08-06 BR BRPI0716026-7A patent/BRPI0716026A2/pt not_active Application Discontinuation
- 2007-08-06 KR KR1020097004839A patent/KR20090053903A/ko not_active Ceased
- 2007-08-06 TW TW096128916A patent/TWI426073B/zh not_active IP Right Cessation
- 2007-08-06 DK DK13167750.2T patent/DK2650291T3/en active
- 2007-08-06 RU RU2009104959/04A patent/RU2500679C2/ru active
- 2007-08-06 CN CN201210396409.0A patent/CN103232442B/zh not_active Expired - Fee Related
- 2007-08-06 IN IN1560MUN2014 patent/IN2014MN01560A/en unknown
- 2007-08-06 JP JP2009523811A patent/JP2010513222A/ja active Pending
- 2007-08-06 US US11/882,892 patent/US7879867B2/en active Active
- 2007-08-06 MX MX2009001208A patent/MX2009001208A/es active IP Right Grant
- 2007-08-06 ES ES13167750.2T patent/ES2652670T3/es active Active
- 2007-08-06 WO PCT/US2007/017476 patent/WO2008021049A2/en not_active Ceased
- 2007-08-06 CA CA002658843A patent/CA2658843A1/en not_active Abandoned
- 2007-08-07 AR ARP070103473A patent/AR062232A1/es not_active Application Discontinuation
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2009
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2010
- 2010-12-16 US US12/970,297 patent/US8258296B2/en not_active Expired - Fee Related
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2013
- 2013-07-25 JP JP2013154163A patent/JP2014012673A/ja active Pending
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2015
- 2015-07-09 JP JP2015137404A patent/JP2015193642A/ja active Pending
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2016
- 2016-10-06 IL IL248216A patent/IL248216B/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| AU2007284851A1 (en) | 2008-02-21 |
| US7879867B2 (en) | 2011-02-01 |
| JP2010513222A (ja) | 2010-04-30 |
| TWI426073B (zh) | 2014-02-11 |
| US20110092702A1 (en) | 2011-04-21 |
| EP2650291A1 (en) | 2013-10-16 |
| RU2500679C2 (ru) | 2013-12-10 |
| IL196722A (en) | 2016-10-31 |
| WO2008021049A2 (en) | 2008-02-21 |
| EP2049504A4 (en) | 2010-09-22 |
| EP2650291B1 (en) | 2017-10-04 |
| AR062232A1 (es) | 2008-10-22 |
| JP2014012673A (ja) | 2014-01-23 |
| IL248216B (en) | 2018-03-29 |
| WO2008021049A9 (en) | 2008-10-30 |
| EP2049504A2 (en) | 2009-04-22 |
| TW200823197A (en) | 2008-06-01 |
| RU2009104959A (ru) | 2010-08-20 |
| IN2014MN01560A (cg-RX-API-DMAC10.html) | 2015-05-08 |
| WO2008021049A3 (en) | 2008-12-31 |
| IL196722A0 (en) | 2009-11-18 |
| ES2652670T3 (es) | 2018-02-05 |
| US8258296B2 (en) | 2012-09-04 |
| DK2650291T3 (en) | 2017-10-23 |
| MX2009001208A (es) | 2009-04-14 |
| KR20090053903A (ko) | 2009-05-28 |
| CN103232442A (zh) | 2013-08-07 |
| CN103232442B (zh) | 2015-01-21 |
| AU2007284851B2 (en) | 2013-05-09 |
| US20080076787A1 (en) | 2008-03-27 |
| BRPI0716026A2 (pt) | 2013-08-06 |
| JP2015193642A (ja) | 2015-11-05 |
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| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20170906 |