WO2007101935A2 - Nouveaux derives heterocycliques cycloalkyles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent - Google Patents
Nouveaux derives heterocycliques cycloalkyles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent Download PDFInfo
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- WO2007101935A2 WO2007101935A2 PCT/FR2007/000384 FR2007000384W WO2007101935A2 WO 2007101935 A2 WO2007101935 A2 WO 2007101935A2 FR 2007000384 W FR2007000384 W FR 2007000384W WO 2007101935 A2 WO2007101935 A2 WO 2007101935A2
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- 0 *C(*(C=C1)C=CC(S2)=C1N(CCOc1ccc(C[C@@](C(O)=O)OCC(F)(F)F)cc1)C2=O)=* Chemical compound *C(*(C=C1)C=CC(S2)=C1N(CCOc1ccc(C[C@@](C(O)=O)OCC(F)(F)F)cc1)C2=O)=* 0.000 description 3
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
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- 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
- A61K31/41—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
- A61K31/428—Thiazoles condensed with carbocyclic rings
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- 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
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Definitions
- the present invention relates to novel heterocyclic cycloalkyl derivatives, process for their preparation and pharmaceutical compositions containing them.
- the compounds described in the present invention are new and have particularly advantageous pharmacological properties: they are excellent hypoglycemic and lipid-lowering agents.
- non-insulin-dependent type II diabetes remains unsatisfactory despite the placing on the market of numerous oral hypoglycemic agents intended to facilitate the secretion of insulin and to promote its action at the peripheral target tissues.
- thiazolidinedione Rosiglitazone induces the expression of genes specific for lipid metabolism such as aP2 and adipsin as well as the expression of glucose transporters GLUT1 and GLUT4, suggesting that the effect of thiazolidinediones observed in vivo can be mediated via adipose tissue.
- This specific effect is obtained by the stimulation of nuclear transcription factors: "peroxisome proliferator-activated receptor gamma" (PPAR i).
- PPAR i peroxisome proliferator-activated receptor gamma
- hypoglycemic agents have significant side effects (hepatic, cardiac, hematopoietic) that limit their long-term use in the treatment of non-insulin-dependent type II diabetes.
- side effects hepatic, cardiac, hematopoietic
- the development of new therapeutic agents that are less toxic and long-term active is absolutely necessary. necessary in this pathology.
- hyperlipidemia is often observed in diabetics (Diabetes Care, 1995, 18 (supplement 1), 86/8/93).
- diabetes Care, 1995, 18 (supplement 1) 86/8/93.
- hyperglycemia promotes the risk of cardiovascular disease in diabetics.
- Hyperglycemia, hyperlipidemia and obesity have become pathologies of the modern world marked by a large amount of food intake and a chronic lack of exercise.
- the compounds of the present invention in addition to their novelty, meet these pharmacological criteria and are excellent hypoglycemic and lipid-lowering agents.
- the present invention relates more particularly to the compounds of formula (I):
- R 1 represents a cycloalkyl (C 3 -C 8 ) group
- R 2 represents a group of formula (II):
- R represents a hydrogen atom or a linear or branched (C 1 -C 6 ) alkyl group
- X represents an oxygen atom, or an N-OR 'group in which R' represents a hydrogen atom, a linear or branched (C 1 -C 6 ) alkyl, aryl or aryl (C 1 -C 6) alkyl group; ) linear or branched,
- aryl means a phenyl or naphthyl group, these groups possibly being optionally substituted with 1 to 3 groups chosen from linear or branched (C 1 -C 6 ) alkyl, linear or branched (C 1 -C 6 ) polyhaloalkyl, alkoxy ( C 1 -C 6 ) linear or branched, hydroxy, carboxy, formyl, amino (optionally substituted by one or two linear or branched (C 1 -C 6 ) alkyl groups), ester, amido, nitro, cyano, or halogen atoms.
- hydrochloric hydrobromic, sulfuric, phosphonic, acetic, trifluoroacetic, lactic, pyruvic, malonic, succinic, glutaric, fumaric, tartaric, maleic, citric, ascorbic, methanesulphonic and camphoric acids. , oxalic, etc.
- the preferred compounds of the invention are the compounds of formula (I) for which R 1 represents a cyclopropyl group.
- R preferably represents a hydrogen atom or an ethyl group.
- the preferred R 2 group of the compounds of formula (I) according to the invention is the group -CH 2 -CH (OCH 2 CF 3 ) (COOH).
- the group R 2 is of R or S configuration.
- X preferably represents an oxygen atom.
- the compounds of formula (I) according to the invention for which R represents a hydrogen atom are advantageously converted into salts, and more particularly into sodium salts.
- the present invention also relates to the process for preparing the compounds of formula (I), characterized in that a compound of formula (III) is used as starting material:
- An advantageous variant relates to the process for preparing the compounds of formula (I / b), characterized in that a compound of formula (III) is used as starting material:
- the present invention also relates to the process for the preparation of the compounds of formula (I) for which the R 2 group is of R or S configuration, characterized in that the compound of formula (I / c) is used as starting material , a particular case of the compounds of formula (I):
- the compounds of the present invention possess very valuable pharmacological properties.
- They can be used as inhibitors of aldose reductase, to improve cognitive functions in dementia and complications of diabetes, inflammatory bowel diseases, myotonic dystrophies, pancreatitis, arteriosclerosis, xanthoma.
- the activity of these compounds is also recommended for the treatment and / or prophylaxis of other diseases including type I diabetes, hypertriglyceridemia, syndrome X, insulin resistance, dyslipidemia in diabetics, hyperlipidemia , hypercholesterolemia, high blood pressure, heart failure, cardiovascular diseases including atherosclerosis.
- diseases including type I diabetes, hypertriglyceridemia, syndrome X, insulin resistance, dyslipidemia in diabetics, hyperlipidemia , hypercholesterolemia, high blood pressure, heart failure, cardiovascular diseases including atherosclerosis.
- these compounds are indicated for use in the regulation of appetite, particularly in the regulation of food intake in subjects suffering from disorders such as obesity, anorexia, bulimia and anorexia nervosa.
- these compounds can be used in prevention or for the treatment of hypercholesterolemia, obesity with beneficial effects on hyperlipidemia, hyperglycemia, osteoporosis, glucose intolerance, resistance to insulin or diseases in which insulin resistance is a secondary pathophysiological mechanism.
- the use of these compounds reduces total cholesterol, body weight, leptin resistance, plasma glucose, triglycerides, LDL, VLDL and plasma free fatty acids.
- HMG CoA reductase inhibitors fibrates, nicotinic acid, cholestyramine, colestipol, probucol, GLP1, metformin, biguanides or glucose reabsorption inhibitors, and may be administered together or at different times to act synergistically in the treated patient.
- compositions according to the invention mention may be made more particularly of those which are suitable for oral, parenteral, nasal, percutaneous, rectal, perlingual, ocular or respiratory administration and in particular simple or coated tablets, sublingual tablets, sachets, packets, capsules, glossettes, tablets, suppositories, creams, ointments, dermal gels and oral or injectable ampoules.
- the dosage varies according to the sex, age and weight of the patient, the route of administration, the nature of the therapeutic indication, or possibly associated treatments and ranges between 0.1 mg and 1 g per 24 hours. in 1 or more takes.
- the present invention also relates to a novel combination of a heterocyclic derivative of formula (I) as defined above and an antioxidant agent for obtaining pharmaceutical compositions useful in the treatment and prevention of obesity and weight overload characterized by a body weight index greater than 25.
- the antioxidants of the combination according to the invention are more particularly free radical scavengers or scavengers of free radicals, antilipoperoxidizing agents, chelating agents or agents capable of regenerating endogenous antioxidants such as glutathione, vitamin C or vitamin E as well as their addition salts with a pharmaceutically acceptable acid or base.
- the antioxidant agent of the combination according to the invention is more preferably represented by quinone derivatives such as ubiquinone or coenzyme Q 10 , which acts as a scavenger of free radicals but which is also capable of regenerating vitamin E .
- the preferred combination according to the invention is 3- ⁇ 4- [2- (6- (cyclopropylcarbonyl) -2-oxo-1, 3-benzothiazol-3 (2H) -yl) ethoxy] phenyl ⁇ -2 - (2,2,2-trifluoroethoxy) propanoic acid, its enantiomers as well as its addition salts with a pharmaceutically acceptable base, and coenzyme Q 10 .
- the combination according to the invention has quite surprising pharmacological properties: the Applicant has in fact demonstrated the existence of a synergy between the two compounds of the combination which makes it possible to obtain a very significant reduction. body fat making it useful in the treatment and / or prevention of obesity and overweight characterized by a body weight index greater than 25.
- Obesity in the United States reaches 20% of men and 25% of women.
- Patients with body weight index (EVIC weight (kg) / height 2 (m 2 )) greater than or equal to 30 are considered obese (Int.JO Obes., 1998, 22, 39-47; Obesity Lancet , 1997, 350, 423-426).
- Obesity (DVIC> 30) and overweight (25 ⁇ EVIC ⁇ 30) can have several origins: they can occur as a result of deregulation of food intake, hormonal dysregulation or following administration of treatment: Type II anti-diabetic therapy with sulfonylureas results in weight gain in patients.
- the combination according to the invention thus finds its utility in the treatment and / or prevention of obesity and weight overload characterized by a body index greater than 25.
- the invention therefore relates to the use of the association between a compound of formula (I) and an antioxidant agent for obtaining pharmaceutical compositions intended for the treatment and / or prevention of obesity and weight overload characterized by a body index greater than 25 and less than 30.
- the combination according to the invention is useful in the treatment and / or prevention of obesity and overweight characterized by a body index greater than 25 and less than 30 induced by a therapeutic treatment, such as the treatment of Type I or IL diabetes
- the invention therefore relates to the use of the combination between a compound of formula (I) and an antioxidant agent for obtaining pharmaceutical compositions intended for the treatment and / or prevention of obesity and weight overload characterized by a body index greater than 25 and less than 30 induced by a therapeutic treatment, such as the treatment of type I or II diabetes.
- the invention also relates to pharmaceutical compositions containing the combination of a compound of formula (I) and an antioxidant as defined above in combination with one or more pharmaceutically acceptable excipients.
- compositions according to the invention mention may be made more particularly of those which are suitable for oral, parenteral, nasal administration, single or sugar-coated tablets, sublingual tablets, capsules, lozenges, suppositories, creams, ointments , dermal gels, etc.
- the invention relates to pharmaceutical compositions containing a compound of formula (I) as defined above and an antioxidant such as coenzyme Q 10 or vitamin E in combination with one or more pharmaceutically acceptable excipients.
- the dosage varies according to the sex, age and weight of the patient, the route of administration, the nature of the therapeutic indication or any associated treatments and ranges between 0.1 mg and 1 g of each component of the association by 24 hours in one or more catches.
- Example 2 The procedure is as in Example 2 starting from the compound obtained in Example 3.
- the title product is obtained in the form of a greenish powder. Melting point: 88-90 ° C
- Example 2 The procedure is as in Example 2 starting from the compound obtained in Example 5.
- the title product is obtained in the form of a yellow powder.
- Step A (2S) -3- ⁇ 4- [2- (6- (Cyclopropylcarbonyl) -2-oxo-1,3-benzothiazol-3 (2H) -yl) ethoxy] phenyl ⁇ -IV - [(1S) 2-hydroxy-1-phenylethyl] -2- (2,2,2-trifluoroethoxy) propanamide
- Example 2 The compound obtained in Example 2 (Ig) is dissolved in 90 ml of anhydrous dichloromethane, and 330 ⁇ l of triethylamine are added. The temperature is lowered to 0 ° C. and 320 mg of HOBt then 450 mg of EDCI are added. After stirring for 15 minutes, 290 mg of (S) -phenylglycinol are added. The mixture is stirred for 20 hours at room temperature. The medium is hydrolyzed and then extracted with dichloromethane. The organic phases are dried, evaporated and the residue purified on a semi-preparative column (eluent: petroleum ether / ethyl acetate 35/65), to yield the title product in the form of a white solid.
- a semi-preparative column eluent: petroleum ether / ethyl acetate 35/65
- Step A (2R) -3- ⁇ 4- [2- (6- (Cyclopropylcarbonyl) -2-oxo-1,3-benzothiazol-3 (2H) -yl) ethoxy] phenyl ⁇ -IV - [(1S) 2-hydroxy-1-phenylethyl] -2- (2,2,2-trifluoroethoxy) propanamide
- Example 9 The procedure is as in Example 9 from the compound obtained in Example 8 and replacing the soda with potassium hydroxide. Lyophilisate.
- Acute toxicity was assessed after oral administration to batches of 8 mice (26 ⁇ 2 g). The animals were observed at regular intervals during the first day and daily for two weeks following treatment. The LD 50 , resulting in the death of 50% of the animals, was evaluated and showed the low toxicity of the compounds of the invention.
- the 10-week old ob / ob male mouse (Harlan) is used for in vivo testing. These animals are kept under a 12-hour light-dark cycle at 25 ° C. This mouse has a basal hyperglycemia of 2 g / l. Animals are randomized to their blood glucose levels to form groups of eight. The orally tested compounds are dissolved in a mixture of hydroxyethyl cellulose (1% HEC) to be administered at 3 mg / kg in a volume of 10 ml / kg, once a day for four days. The control group receives the solvents under the same conditions as the treated groups.
- HEC hydroxyethyl cellulose
- the activity of the products is evaluated by measuring blood glucose, insulinemia and triglyceridemia 24 hours after the last administration and by daily measurement of body weight.
- the compounds of the invention show a very good ability to reduce blood glucose comparable to the effects obtained with Rosiglitazone, the reference substance.
- the compound of Example 2 administered at 3 mg / kg orally in ob / ob mice normalizes glycemia, insulinemia and triglyceride: respective reductions of 42%, 71% and 45% values observed in control mice.
- mice 8 to 12 weeks old Male C57 Black 6 ob / ob mice 8 to 12 weeks old were used. After quarantine for one week, they were weighed and randomized according to their weight, and 6 homogeneous groups (not significantly different starting weight) were formed. After having been weighed, the various combinations according to the invention between a compound of formula (I) and an antioxidant agent to be tested are injected intraperitoneally once. per day for 7 days. The molecules are injected into a 5% DMSO solution / 15% Solutol / Qsp H 2 O heated at 65 ° C. to ensure good dissolution. The solution is further preheated before injection. The mice are weighed daily and the weight obtained after 7 days of treatment is recorded. The results obtained clearly show:
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Abstract
Description
Claims
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002643694A CA2643694A1 (fr) | 2006-03-06 | 2007-03-05 | Nouveaux derives heterocycliques cycloalkyles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
EP07731083A EP1991537A2 (fr) | 2006-03-06 | 2007-03-05 | Nouveaux derives heterocycliques cycloalkyles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
MX2008011449A MX2008011449A (es) | 2006-03-06 | 2007-03-05 | Derivados de cicloalquilo heterociclicos novedosos, metodo para la preparacion de los mismos, y composiciones farmaceuticas que contienen los mismos. |
AU2007222292A AU2007222292A1 (en) | 2006-03-06 | 2007-03-05 | Novel heterocyclic cycloalkyl derivatives, method for the preparation thereof, and pharmaceutical compositions containing the same |
BRPI0708586-9A BRPI0708586A2 (pt) | 2006-03-06 | 2007-03-05 | derivados heterocìclicos cicloalquilas, respectivo processo de preparo e composições farmacêuticas que contêm |
JP2008557793A JP2009529026A (ja) | 2006-03-06 | 2007-03-05 | 新規な複素環シクロアルキル誘導体、その製造法およびそれを含有する薬学的組成物 |
US12/224,861 US20090239917A1 (en) | 2006-03-06 | 2007-03-05 | Heterocyclic Cycloalkyl Compounds, a Process for their Preparation and Pharmaceutical Compositions Containing Them |
EA200801910A EA200801910A1 (ru) | 2006-03-06 | 2007-03-05 | Новые гетероциклические циклоалкильные соединения, способ их получения и фармацевтические композиции, которые их содержат |
NO20083945A NO20083945L (no) | 2006-03-06 | 2008-09-16 | Nye heterosykliske sykloalkylforbindelser, en fremgangsmate for deres fremstilling og farmasoytiske sammensetninger inneholdende dem |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0601954A FR2898125B1 (fr) | 2006-03-06 | 2006-03-06 | Nouveaux derives heterocycliques cycloalkyles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
FR0601954 | 2006-03-06 |
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WO2007101935A2 true WO2007101935A2 (fr) | 2007-09-13 |
WO2007101935A3 WO2007101935A3 (fr) | 2008-02-21 |
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PCT/FR2007/000384 WO2007101935A2 (fr) | 2006-03-06 | 2007-03-05 | Nouveaux derives heterocycliques cycloalkyles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Country Status (16)
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US (1) | US20090239917A1 (fr) |
EP (1) | EP1991537A2 (fr) |
JP (1) | JP2009529026A (fr) |
KR (1) | KR20080099871A (fr) |
CN (1) | CN101395145A (fr) |
AR (1) | AR059749A1 (fr) |
AU (1) | AU2007222292A1 (fr) |
BR (1) | BRPI0708586A2 (fr) |
CA (1) | CA2643694A1 (fr) |
EA (1) | EA200801910A1 (fr) |
FR (1) | FR2898125B1 (fr) |
MA (1) | MA30295B1 (fr) |
MX (1) | MX2008011449A (fr) |
NO (1) | NO20083945L (fr) |
TW (1) | TW200745068A (fr) |
WO (1) | WO2007101935A2 (fr) |
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KR101216274B1 (ko) | 2011-06-17 | 2012-12-28 | 이화여자대학교 산학협력단 | 골다공증 완화, 예방 또는 치료효과의 신규한 화합물, 이의 제조방법 및 이를 포함하는 약학조성물 |
Citations (3)
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WO2001057002A1 (fr) * | 2000-02-02 | 2001-08-09 | Les Laboratoires Servier | Derives d'azoles condenses et leur utilisation comme agents hypoglycemiants |
EP1502590A1 (fr) * | 2003-07-28 | 2005-02-02 | Les Laboratoires Servier | Dérivés d'oximes hétérocycliques, leur procédé de préparation et leur utilisation dans le traitement du diabète de type II |
WO2005099694A1 (fr) * | 2004-03-31 | 2005-10-27 | Les Laboratoires Servier | Association entre un compose heterocyclique et un agent antioxydant et son utilisation pour le traitement de l’obesite |
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2006
- 2006-03-06 FR FR0601954A patent/FR2898125B1/fr not_active Expired - Fee Related
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2007
- 2007-03-05 AU AU2007222292A patent/AU2007222292A1/en not_active Abandoned
- 2007-03-05 TW TW096107525A patent/TW200745068A/zh unknown
- 2007-03-05 CA CA002643694A patent/CA2643694A1/fr not_active Abandoned
- 2007-03-05 EA EA200801910A patent/EA200801910A1/ru unknown
- 2007-03-05 WO PCT/FR2007/000384 patent/WO2007101935A2/fr active Application Filing
- 2007-03-05 KR KR1020087024383A patent/KR20080099871A/ko not_active Application Discontinuation
- 2007-03-05 US US12/224,861 patent/US20090239917A1/en not_active Abandoned
- 2007-03-05 EP EP07731083A patent/EP1991537A2/fr not_active Withdrawn
- 2007-03-05 MX MX2008011449A patent/MX2008011449A/es not_active Application Discontinuation
- 2007-03-05 CN CNA200780007648XA patent/CN101395145A/zh active Pending
- 2007-03-05 BR BRPI0708586-9A patent/BRPI0708586A2/pt not_active IP Right Cessation
- 2007-03-05 JP JP2008557793A patent/JP2009529026A/ja active Pending
- 2007-03-06 AR ARP070100912A patent/AR059749A1/es unknown
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2008
- 2008-09-16 NO NO20083945A patent/NO20083945L/no not_active Application Discontinuation
- 2008-09-29 MA MA31264A patent/MA30295B1/fr unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001057002A1 (fr) * | 2000-02-02 | 2001-08-09 | Les Laboratoires Servier | Derives d'azoles condenses et leur utilisation comme agents hypoglycemiants |
EP1502590A1 (fr) * | 2003-07-28 | 2005-02-02 | Les Laboratoires Servier | Dérivés d'oximes hétérocycliques, leur procédé de préparation et leur utilisation dans le traitement du diabète de type II |
WO2005099694A1 (fr) * | 2004-03-31 | 2005-10-27 | Les Laboratoires Servier | Association entre un compose heterocyclique et un agent antioxydant et son utilisation pour le traitement de l’obesite |
Also Published As
Publication number | Publication date |
---|---|
FR2898125B1 (fr) | 2008-06-13 |
WO2007101935A3 (fr) | 2008-02-21 |
KR20080099871A (ko) | 2008-11-13 |
AU2007222292A1 (en) | 2007-09-13 |
JP2009529026A (ja) | 2009-08-13 |
FR2898125A1 (fr) | 2007-09-07 |
BRPI0708586A2 (pt) | 2011-06-07 |
TW200745068A (en) | 2007-12-16 |
US20090239917A1 (en) | 2009-09-24 |
EP1991537A2 (fr) | 2008-11-19 |
MA30295B1 (fr) | 2009-03-02 |
CN101395145A (zh) | 2009-03-25 |
AR059749A1 (es) | 2008-04-23 |
NO20083945L (no) | 2008-09-16 |
MX2008011449A (es) | 2008-09-24 |
EA200801910A1 (ru) | 2009-02-27 |
CA2643694A1 (fr) | 2007-09-13 |
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