EP2018387A1 - Thiazolyl-dihydro-indazole - Google Patents
Thiazolyl-dihydro-indazoleInfo
- Publication number
- EP2018387A1 EP2018387A1 EP07727389A EP07727389A EP2018387A1 EP 2018387 A1 EP2018387 A1 EP 2018387A1 EP 07727389 A EP07727389 A EP 07727389A EP 07727389 A EP07727389 A EP 07727389A EP 2018387 A1 EP2018387 A1 EP 2018387A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- cycloalkyl
- alkenyl
- alkynyl
- group
- 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.)
- Withdrawn
Links
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
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- 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
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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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
-
- 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
- A61P17/04—Antipruritics
-
- 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
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
-
- 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
- A61P27/14—Decongestants or antiallergics
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- 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
Definitions
- radicals R 1 , R 2 and R 3 have the meanings mentioned in the claims and the description, their tautomers, racemates, enantiomers, diastereomers and their mixtures, and optionally their pharmacologically acceptable acid addition salts, solvates and hydrates, and processes for the preparation of these Thiazolyl-dihydro-indazoles and their use as medicaments.
- R 8 and R 9 together form a saturated or unsaturated 4 to 7-membered alkyl bridge which optionally contains an O atom or an S (O) P group, where p, q independently of one another are 0.1 or 2; or
- R 13 is F, Cl, Br, OH, CN, CF 3, CHF 2, or Ci -4 alkyl-O-,
- R 13 and R 14 together form a saturated or unsaturated 4 to 7-membered alkyl bridge, which optionally contains an O atom or an S (O) P group,
- R 1 and R 3 to R 14 may have the meanings indicated, and R 2 is a radical selected from the group consisting of Cs- ⁇ -cycloalkyl, d-6 alkyl
- NR -> 8rR-> 9 an optionally substituted radical selected from the group consisting of the general formula (B1) to (B8)
- Another object of the invention are compounds of formula (I) for use as medicaments.
- Another object of the invention is the use of the compounds of formula (I) for the manufacture of a medicament for the treatment of a disease selected from the group consisting of allergic rhinitis, allergic sinusitis and nasal polyps.
- Another object of the invention is the use of the compounds of formula (I), for the manufacture of a medicament for the treatment of inflammatory or allergic disease states, in which autoimmune reactions are involved.
- Another object of the invention is the use of the compounds of formula (I) for the manufacture of a medicament for the treatment of a disease selected from the group consisting of Crohn's disease, ulcerative colitis, systemic lupus erythematosus, chronic hepatitis, multiple sclerosis, rheumatoid Arthritis, psoriatic arthritis, osteoarthritis, rheumatoid spondylitis.
- a disease selected from the group consisting of Crohn's disease, ulcerative colitis, systemic lupus erythematosus, chronic hepatitis, multiple sclerosis, rheumatoid Arthritis, psoriatic arthritis, osteoarthritis, rheumatoid spondylitis.
- a heterocyclic ring may be provided with a keto group. As an example for this are called.
- heterocyclic spiro rings is understood to mean 5-10-membered, spirocyclic rings which may optionally contain one, two or three heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen, in which case the ring can be attached via a carbon atom or if present, be linked to the molecule via a nitrogen atom. Unless otherwise stated, a spirocyclic ring may be provided with a keto group. As examples are mentioned:
- Aromatic or non-aromatic ring systems consisting of carbon atoms and optionally heteroatoms, which in turn may be substituted with functional groups.
- the substituent R 1 may be a radical selected from the group consisting of hydrogen, CO-CH 3 , CO-CH 2 -R 4 , CO-CHMe-R 4 , CO-OR 4 , CO-SR 4 , CO-NH 2 and CO-NHR 4 is preferably CO-CH 3 and CO-CH 2 -R 4 . Most preferably, the substituent R 1 is CO-CH 3 .
- alkenyl C 3- i 2 alkynyl, ds-e-cycloalkyl-Ci. ⁇ - alkyl, C 6 -C 4 aryl, di 2 -alkyl aryl C 6 -C 4, C 2 - i 2 alkenyl C 6 -C 4 aryl, C 2 -i 2 alkynyl C 6 -C 4 aryl, C 3-8 cycloalkyl, C 3-8 cycloalkenyl and NR 11 R 12 C 3-8 -cycloalkyl-, or an optionally substituted radical selected from the group consisting of the general formulas (A1) to (A12)
- the substituents R 11, R 12 may be the same or different, are hydrogen or an optionally substituted radical selected from the group consisting of Ci- io alkyl, C ß -io-alkenyl, and C ß -io-alkynyl, Cs-e cycloalkyl-d ⁇ alkyl and C 3 _ 6 cycloalkyl, preferably of Ci.io-alkyl, C 3- io-alkenyl, Cs- ⁇ -cycloalkyl-d ⁇ -alkyl and C 5-6 -cycloalkyl, mean , or
- skin diseases e.g. Psoriasis, contact dermatitis, atopic dermatitis, alopecia areaa (circular hair loss), erythema multiforme (Stevens-Johnson syndrome), dermatitis herpetiformis, scleroderma, vitiligo, hives (urticaria), lupus erythemat
- W represents an anticholinergic agent combined with an active agent selected from the group consisting of betamimetics, corticosteroids, PDE4 inhibitors, EGFR inhibitors and LTD4 antagonists
- W represents a corticosteroid combined with a drug selected from the group consisting of a PDE4 inhibitor, EGFR inhibitor and LTD4 antagonist
- Preferred betamimetics for this purpose are compounds selected from the group consisting of albuterol, arformoterol, bambuterol, bitolertrol, broxaterol, carbuterol, clenbuterol, fenoterol, formoterol, hexoprenaline, ibuterol, isoetharines, isoprenaline, levosalbutamol, mabuterol, meluadrine , Metaproterenol, orciprenaline, pirbuterol, procaterol, reproterol, rimiterol, ritodrine, salmefamol, salmetrol, soterenol, sulphoneterol, terbutaline, tiaramide, toluubuterol, zinterol, CHF-1035, HOKU-81, KUL-1248 and (4- ⁇ 6- [2-Hydroxy-2- (4-hydroxy-3-hydroxymethyl-phenyl) -e
- the acid addition salts of the betamimetics are selected from the group consisting of hydrochloride, hydrobromide, hydroiodide, hydrosulfate, hydrophosphate, hydromethanesulfonate, hydronitrate, hydromaleate, hydroacetate, hydrocitrate, hydrofumarate, hydrotartrate, hydroxalate, hydros
- Preferred corticosteroids are compounds which are selected from the group consisting of prednisolone, prednisone, butixocortepionate, flunisolide, beclomethasone, triamcinolone, budesonide, fluticasone, mometasone, cronoside, rofleponide, dexamethasone, betamethasone, deflazacort, RPR -106541, NS-126, ST-26 and
- Etiprednol-dichloroacetate optionally in the form of their racemates, enantiomers or diastereomers and optionally in the form of their salts and derivatives, their solvates and / or hydrates.
- Any reference to steroids includes reference to their optional salts or derivatives, hydrates or solvates.
- Examples of possible salts and derivatives of the steroids may be: alkali metal salts, such as, for example, sodium or potassium salts, suberobenzoates, phosphates, isonicotinates, acetates, propionates, dihydrogen phosphates, palmates, pivalates or even furoates.
- Preferred PDE4 inhibitors here are compounds selected from the group consisting of enprofylline, theophylline, roflumilast, A-riflo (cilomilast), tofimilast, pumafentrin, lirimilast, arofylline, atizoram, D-4418, bay 198004, BY343, CP-325,366, D-4396 (Sch-351591), AWD-12-281 (GW-842470), NCS-613, CDP-840, D-4418, PD-168787, T-440, T-2585, V-1 1294A, CI-1018, CDC-801, CDC-3052, D-22888, YM-58997, Z-15370 and
- Preferred EGFR inhibitors are compounds selected from the group consisting of cetuximab, trastuzumab, ABX-EGF, Mab ICR-62 and
- H1 -Antihistaminika here are preferably compounds used, which are selected from the group consisting of epinastine, cetirizine, azelastine, Fexofena- din, levocabastine, loratadine, mizolastine, ketotifen, emedastine, dimetinden, clemastine, bamipine, cexchlorpheniramine, pheniramine, doxylamine, chlorphenoxamine, dimenhydrinate, diphenhydramine, promethazine, ebastine, desloratidine and meclocine, optionally in the form of their racemates, enantiomers, diastereomers and optionally in Form of their pharmacologically acceptable acid addition salts, solvates or hydrates.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Ophthalmology & Optometry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Otolaryngology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07727389A EP2018387A1 (de) | 2006-04-06 | 2007-03-27 | Thiazolyl-dihydro-indazole |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06112297 | 2006-04-06 | ||
| PCT/EP2007/052916 WO2007115933A1 (de) | 2006-04-06 | 2007-03-27 | Thiazolyl-dihydro-indazole |
| EP07727389A EP2018387A1 (de) | 2006-04-06 | 2007-03-27 | Thiazolyl-dihydro-indazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP2018387A1 true EP2018387A1 (de) | 2009-01-28 |
Family
ID=36763499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP07727389A Withdrawn EP2018387A1 (de) | 2006-04-06 | 2007-03-27 | Thiazolyl-dihydro-indazole |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US20070238718A1 (enExample) |
| EP (1) | EP2018387A1 (enExample) |
| JP (1) | JP2009532417A (enExample) |
| KR (1) | KR20090026129A (enExample) |
| CN (1) | CN101466717A (enExample) |
| AR (1) | AR060266A1 (enExample) |
| AU (1) | AU2007236047A1 (enExample) |
| BR (1) | BRPI0709743A2 (enExample) |
| CA (1) | CA2647295A1 (enExample) |
| IL (1) | IL194496A0 (enExample) |
| MX (1) | MX2008012539A (enExample) |
| RU (1) | RU2008143557A (enExample) |
| TW (1) | TW200806680A (enExample) |
| WO (1) | WO2007115933A1 (enExample) |
| ZA (1) | ZA200807821B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2007227681A1 (en) | 2006-03-15 | 2007-09-27 | Wyeth | N-substituted-azacyclylamines as histamine-3 antagonists |
| US20070238746A1 (en) * | 2006-04-06 | 2007-10-11 | Trixi Brandl | Thiazolyl-dihydro-chinazoline |
| US7691868B2 (en) * | 2006-04-06 | 2010-04-06 | Boehringer Ingelheim International Gmbh | Thiazolyl-dihydro-quinazoline |
| US20070259855A1 (en) * | 2006-04-06 | 2007-11-08 | Udo Maier | Thiazolyl-dihydro-indazole |
| PE20080371A1 (es) | 2006-05-19 | 2008-04-09 | Wyeth Corp | N-benzoil-y-n-bencilpirrolidin-3-ilaminas como antagonistas de histamina-3 |
| PE20081152A1 (es) | 2006-10-06 | 2008-08-10 | Wyeth Corp | Azaciclilaminas n-sustituidas como antagonistas de histamina-3 |
| US20080293771A1 (en) * | 2007-05-24 | 2008-11-27 | Wyeth | Azacyclylbenzamide derivatives as histamine-3 antagonists |
| CA2693138A1 (en) | 2007-07-16 | 2009-01-22 | Wyeth Llc | Aminoalkylazole derivatives as histamine-3 antagonists |
| PE20091617A1 (es) * | 2008-03-13 | 2009-11-12 | Boehringer Ingelheim Int | Tiazolil-dihidro-indazoles |
| US20110230472A1 (en) * | 2008-08-29 | 2011-09-22 | Shionogi & Co., Ltd. | Ring-fused azole derivative having pi3k-inhibiting activity |
| EP2421872B1 (en) * | 2009-04-22 | 2015-06-10 | Boehringer Ingelheim International GmbH | Thia-triaza-as-indacenes as pi3-kinases inhibitors for the treatment of cancer |
| EP2845592A1 (en) * | 2009-09-28 | 2015-03-11 | F. Hoffmann-La Roche AG | Benzoxazepin PI3K inhibitor compounds and methods of use |
| ES2646489T3 (es) | 2013-03-15 | 2017-12-14 | Idorsia Pharmaceuticals Ltd | Novedosos derivados de acrilamida como agentes contra la malaria |
| EP3886854A4 (en) | 2018-11-30 | 2022-07-06 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| US11633399B2 (en) | 2018-12-25 | 2023-04-25 | Sol-Gel Technologies Ltd. | Treatment of skin disorders with compositions comprising an EGFR inhibitor |
| WO2022092141A1 (ja) * | 2020-10-28 | 2022-05-05 | 塩野義製薬株式会社 | 抗ウイルス活性を有するアミド誘導体 |
| JP7454729B2 (ja) * | 2022-04-27 | 2024-03-22 | 塩野義製薬株式会社 | 抗ウイルス活性を有するアミド誘導体を含有する医薬組成物 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5547975A (en) * | 1994-09-20 | 1996-08-20 | Talley; John J. | Benzopyranopyrazolyl derivatives for the treatment of inflammation |
| US7091227B2 (en) * | 2000-02-07 | 2006-08-15 | Abbott Gmbh & Co. Kg | Benzothiazole derivatives |
| DE10344223A1 (de) * | 2003-09-24 | 2005-04-21 | Merck Patent Gmbh | 1,3-Benzoxazolylderivate als Kinase-Inhibitoren |
| AU2005293607A1 (en) * | 2004-10-07 | 2006-04-20 | Boehringer Ingelheim International Gmbh | PI3 kinases |
| UY29149A1 (es) * | 2004-10-07 | 2006-05-31 | Boehringer Ingelheim Int | Tiazolil-dihidro-indazoles |
-
2007
- 2007-03-23 US US11/690,351 patent/US20070238718A1/en not_active Abandoned
- 2007-03-27 BR BRPI0709743-3A patent/BRPI0709743A2/pt not_active IP Right Cessation
- 2007-03-27 EP EP07727389A patent/EP2018387A1/de not_active Withdrawn
- 2007-03-27 KR KR1020087027299A patent/KR20090026129A/ko not_active Withdrawn
- 2007-03-27 CN CNA200780021166XA patent/CN101466717A/zh active Pending
- 2007-03-27 RU RU2008143557/04A patent/RU2008143557A/ru not_active Application Discontinuation
- 2007-03-27 AU AU2007236047A patent/AU2007236047A1/en not_active Abandoned
- 2007-03-27 CA CA002647295A patent/CA2647295A1/en not_active Abandoned
- 2007-03-27 JP JP2009503536A patent/JP2009532417A/ja active Pending
- 2007-03-27 WO PCT/EP2007/052916 patent/WO2007115933A1/de not_active Ceased
- 2007-03-27 MX MX2008012539A patent/MX2008012539A/es not_active Application Discontinuation
- 2007-04-03 AR ARP070101384A patent/AR060266A1/es unknown
- 2007-04-04 TW TW096111948A patent/TW200806680A/zh unknown
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2008
- 2008-09-11 ZA ZA200807821A patent/ZA200807821B/xx unknown
- 2008-10-02 IL IL194496A patent/IL194496A0/en unknown
- 2008-11-25 US US12/277,543 patent/US20090093474A1/en not_active Abandoned
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2007115933A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20090026129A (ko) | 2009-03-11 |
| JP2009532417A (ja) | 2009-09-10 |
| WO2007115933A1 (de) | 2007-10-18 |
| BRPI0709743A2 (pt) | 2011-07-26 |
| AR060266A1 (es) | 2008-06-04 |
| RU2008143557A (ru) | 2010-06-20 |
| IL194496A0 (en) | 2009-08-03 |
| MX2008012539A (es) | 2008-10-10 |
| AU2007236047A1 (en) | 2007-10-18 |
| US20090093474A1 (en) | 2009-04-09 |
| CN101466717A (zh) | 2009-06-24 |
| CA2647295A1 (en) | 2007-10-18 |
| TW200806680A (en) | 2008-02-01 |
| US20070238718A1 (en) | 2007-10-11 |
| ZA200807821B (en) | 2009-08-26 |
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