AR061052A1 - Proceso industrial para la sintesis de 17(alfa)-acetoxi-11(beta)-[-4-n,n-dimetil-amino)- fenil]-19-norpregna-4,9-dieno- 3,20-diona y productos intermedios del proceso - Google Patents
Proceso industrial para la sintesis de 17(alfa)-acetoxi-11(beta)-[-4-n,n-dimetil-amino)- fenil]-19-norpregna-4,9-dieno- 3,20-diona y productos intermedios del procesoInfo
- Publication number
- AR061052A1 AR061052A1 ARP070102187A ARP070102187A AR061052A1 AR 061052 A1 AR061052 A1 AR 061052A1 AR P070102187 A ARP070102187 A AR P070102187A AR P070102187 A ARP070102187 A AR P070102187A AR 061052 A1 AR061052 A1 AR 061052A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- norpregna
- 17alpha
- ethylene
- dioxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 7
- 230000015572 biosynthetic process Effects 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 239000013067 intermediate product Substances 0.000 title 1
- -1 ethylene-dioxy Chemical group 0.000 abstract 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 239000012453 solvate Substances 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000007818 Grignard reagent Substances 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 230000021736 acetylation Effects 0.000 abstract 2
- 238000006640 acetylation reaction Methods 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000004795 grignard reagents Chemical class 0.000 abstract 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 abstract 1
- ONMSBNJJCUCYED-UHFFFAOYSA-N 2-bromo-n,n-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1Br ONMSBNJJCUCYED-UHFFFAOYSA-N 0.000 abstract 1
- XYZWMVYYUIMRIZ-UHFFFAOYSA-N 4-bromo-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(Br)C=C1 XYZWMVYYUIMRIZ-UHFFFAOYSA-N 0.000 abstract 1
- 241000790917 Dioxys <bee> Species 0.000 abstract 1
- DOJXGHGHTWFZHK-UHFFFAOYSA-N Hexachloroacetone Chemical compound ClC(Cl)(Cl)C(=O)C(Cl)(Cl)Cl DOJXGHGHTWFZHK-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- CIHXIRAAMAUYLZ-UHFFFAOYSA-N [K+].[K+].[C-]#[C-] Chemical compound [K+].[K+].[C-]#[C-] CIHXIRAAMAUYLZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 abstract 1
- 238000010511 deprotection reaction Methods 0.000 abstract 1
- 150000002118 epoxides Chemical group 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1
- JWUKZUIGOJBEPC-UHFFFAOYSA-N phenyl thiohypochlorite Chemical compound ClSC1=CC=CC=C1 JWUKZUIGOJBEPC-UHFFFAOYSA-N 0.000 abstract 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 abstract 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/005—Ketals
- C07J21/006—Ketals at position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
- A61P5/46—Drugs for disorders of the endocrine system of the suprarenal hormones for decreasing, blocking or antagonising the activity of glucocorticosteroids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0077—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom
- C07J41/0083—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom substituted in position 11-beta by an optionally substituted phenyl group not further condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/001—Oxiranes
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Reivindicacion 1: Un proceso industrial para la síntesis de 17alfa-acetoxi-11beta-[-4-N,N-dimetil-amino)-fenil]-19-norpregna-4,9-dieno-3,20-diona libre de solvato de la formula (1) vía formacion de cetal a partir de 3-(etileno-dioxi)-17alfa--hidroxi- 19-norpregna-5(10),9(11)-dieno-20-ona de la formula (6), formacion de epoxidos en posicion 5,10 del 3,3,20,20-bis(etiIeno-dioxi)-17alfa-hidroxi-19-norpregna-5(10),9 (11)-dieno de la formula (5), reaccion del 3,3,20,20-bis8etileno-dioxi)-17alfa- hidroxi-5,10-epoxi-9-norpregna-9(11)-eno de la formula (4) con el reactivo de Grignard obtenido de bromo-N,N-dimetil-anilina, desproteccion del así formado 3,3,20,20-bis(etileno-dioxi)-5alfa,17alfa-dihidroxi-11beta-[4-(N,N-dimetilamino)-fenil]-19- norpregna-9(11)-eno de la formula (3), acetilacion del 11beta-[4-(N,N- dimetilamino)-fenil]-17alfa-hidroxi-19-norpregna-4,9-dieno-3,20-diona obtenido de la formula (2) y la liberacion final del producto deseado, caracterizado porque, (i) 3-(etileno- dioxi)-estra-5(10),9(11)-dieno-17-ona de la formula (10) se hace reaccionar con acetilida potásica in situ en tetrahidrofurano seco por un método conocido; ii) 3-(etileno-dioxi)-17alfa-etinil-17beta-hidroxi-estra-5(10),9(11 )-dieno de la formula (9) obtenido se hace reaccionar con cloruro de fenilsulfenilo en diclorometano en la presencia de trietilamina y ácido acético; iii) la mezcla isomérica obtenida de 3-(etileno-dioxi)-21(fenil-sulfinil)-19-norpregna-5(10),9(11),17(20),20-tetraeno de la formula (8) se hace reaccionar primero con metoxido de sodio en metanol, luego con fosfito de trimetilo, iv) 3-(etileno-dioxi)-17alfa-hidroxi-20-metoxi-19-norpregna-5(1 0),(11),20-trieno obtenido la formula (7) se hace reaccionar con cloruro de hidrogeno en metanol, luego v) 3-(etileno-.dioxi)-17alfa-hidroxi-19-norpregna-5(10),9(11)-dieno-20-ona de la formula (6) obtenido se hace reaccionar con etilenglicol en diclorometano en la presencia de ortoformato de trimetilo y ácido p- toluenosulfonico por un método conocido; vi) 3,3,20,20-bis(etileno-dioxi)-17alfa-hidroxi-19-norpregna-5(10),9(11)-dieno de la formula (5) obtenido se hizo reaccionar con peroxido de hidrogeno en una mezcla de piridina y diclorometano en la presencia de hexacloroacetona por un método conocido; vii) 3,3,20,20-bis(etileno-dioxi)-17alfa-hidroxi-5,10-epoxi-19-norpregna-9(11)-eno de la formula (4) obtenido que contiene aproximadamente una mezcla 1:1 de 5alfa, 10alfa- y 5beta,10beta-epoxidos con un reactivo de Grignard obtenido a partir de 4-bromo-N,N-dimetil-anilina en tetrahidrofurano en la presencia de catalizador cloruro de cobre (1) sin la separacion de isomeros por un método conocido; viii) 3,3,20,20-bis(etileno-dioxi)-5alfa,17alfa- dihidroxi-11b-[4-(N,N-dimetilamino)-fenil]-9-norpregna-9(11)-eno obtenido de la formula (3) se reacciona con sulfato de hidrogeno potásico en agua por un método conocido; ix) acetilacion de 11beta-[4-(N,N-dimetilamino)-fenil]-17alfa-hidroxi-19- norpregna-4,9-dieno-3,10-diona de la formula (2) obtenido con anhídrido acético en la presencia de ácido perclorico por un método conocido, y, finalmente, x) liberacion del compuesto libre de solvato de la formula (1) a partir del solvato obtenido que contiene el compuesto de la formula (1) en una mezcla 1:1 de etanol y agua a 70°C.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU0600491A HU227112B1 (hu) | 2006-06-14 | 2006-06-14 | Ipari eljárás 17-alfa-acetoxi-11-béta-[4-(N,N-dimetil-amino)-fenil]-19-norpregna-4,9-dién-3,20-dion elõállítására és új intermedierek az eljáráshoz |
Publications (1)
Publication Number | Publication Date |
---|---|
AR061052A1 true AR061052A1 (es) | 2008-07-30 |
Family
ID=89986843
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ARP070102187A AR061052A1 (es) | 2006-06-14 | 2007-05-21 | Proceso industrial para la sintesis de 17(alfa)-acetoxi-11(beta)-[-4-n,n-dimetil-amino)- fenil]-19-norpregna-4,9-dieno- 3,20-diona y productos intermedios del proceso |
Country Status (22)
Country | Link |
---|---|
US (1) | US8110691B2 (es) |
EP (1) | EP2027140B1 (es) |
JP (1) | JP5274453B2 (es) |
CN (1) | CN101466723B (es) |
AR (1) | AR061052A1 (es) |
AU (1) | AU2007258955B2 (es) |
BR (1) | BRPI0713157A2 (es) |
CA (1) | CA2653552C (es) |
DK (1) | DK2027140T3 (es) |
EA (1) | EA015302B1 (es) |
ES (1) | ES2409841T3 (es) |
HU (1) | HU227112B1 (es) |
IL (1) | IL195253A (es) |
MX (1) | MX2008015972A (es) |
NO (1) | NO341620B1 (es) |
PL (1) | PL2027140T3 (es) |
PT (1) | PT2027140E (es) |
RS (1) | RS52758B (es) |
SI (1) | SI2027140T1 (es) |
UA (1) | UA94269C2 (es) |
WO (1) | WO2007144674A1 (es) |
ZA (1) | ZA200809799B (es) |
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JP6474722B2 (ja) | 2012-09-28 | 2019-02-27 | あすか製薬株式会社 | ウリプリスタール酢酸エステルの結晶多形 |
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CN108558982A (zh) * | 2018-05-21 | 2018-09-21 | 郑州泰丰制药有限公司 | 一种新型醋酸乌利司他以及其生产制造方法 |
CN109053846B (zh) * | 2018-08-14 | 2020-01-07 | 台州仙琚药业有限公司 | 制备醋酸优力司特双缩酮的方法 |
CN111349137A (zh) * | 2018-12-21 | 2020-06-30 | 北京启慧生物医药有限公司 | 一种绿色合成醋酸乌利司他中间体及醋酸乌利司他的方法 |
CN110256519B (zh) * | 2019-05-23 | 2021-06-08 | 江苏联环药业股份有限公司 | 一锅法制备醋酸乌利司他的方法 |
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US4041055A (en) * | 1975-11-17 | 1977-08-09 | The Upjohn Company | Process for the preparation of 17α-hydroxyprogesterones and corticoids from androstenes |
US4954490A (en) * | 1988-06-23 | 1990-09-04 | Research Triangle Institute | 11 β-substituted progesterone analogs |
US5929262A (en) * | 1995-03-30 | 1999-07-27 | The United States Of America As Represented By The Department Of Health And Human Services | Method for preparing 17α-acetoxy-11β-(4-N, N-dimethylaminophyl)-19-Norpregna-4,9-diene-3, 20-dione, intermediates useful in the method, and methods for the preparation of such intermediates |
US6768014B2 (en) * | 1999-12-29 | 2004-07-27 | The United States Of America As Represented By The Department Of Health And Human Services | PROCESS FOR PREPARING 17α-ACETOXY-11β-[4-N,N(DIMETHYLAMINO)PHENYL]-21-METHOXY-19-NORPREGNA-4,9-DIENE-3,20-DIONE, INTERMEDIATES USEFUL IN THE PROCESS , AND PROCESSES FOR PREPARING SUCH INTERMEDIATES |
US6512130B1 (en) * | 2000-09-05 | 2003-01-28 | Council Of Scientific And Industrial Research | Mifepristone analogue, process for the preparation thereof and use thereof |
AU2004217988C1 (en) * | 2003-02-28 | 2010-06-03 | Southwest Foundation For Biomedical Research | Method for preparing 17 alpha-acetoxy-11beta-(4-N,N-dimethylaminophenyl)-19-norpregna-4,9-diene-3,20-dione, intermediates thereof, and methods for the preparation of such intermediates |
FR2854403B1 (fr) * | 2003-04-29 | 2008-07-11 | Aventis Pharma Sa | Nouveau procede et intermediaires de preparation de composes 19-nor-steroides 17-halogenes |
HUP0301332A3 (en) * | 2003-05-14 | 2006-04-28 | Richter Gedeon Vegyeszet | New mono-and bismethylene steroid derivatives and process for their synthesis and pharmaceutical compositions containing them |
ITMI20042001A1 (it) * | 2004-10-21 | 2005-01-21 | Ind Chimica Srl | Processo per la preparazione di 21-idrossi steroidi con controllo della distribuzione epimerica nella posizione c-21 |
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NO341620B1 (no) | 2017-12-11 |
CN101466723B (zh) | 2011-11-02 |
CN101466723A (zh) | 2009-06-24 |
AU2007258955A1 (en) | 2007-12-21 |
HU0600491D0 (en) | 2006-08-28 |
JP5274453B2 (ja) | 2013-08-28 |
EP2027140A1 (en) | 2009-02-25 |
DK2027140T3 (da) | 2013-06-03 |
JP2009539964A (ja) | 2009-11-19 |
PT2027140E (pt) | 2013-06-04 |
UA94269C2 (en) | 2011-04-26 |
NO20090196L (no) | 2009-03-10 |
RS52758B (en) | 2013-08-30 |
CA2653552A1 (en) | 2007-12-21 |
EP2027140B1 (en) | 2013-03-13 |
IL195253A (en) | 2011-11-30 |
PL2027140T3 (pl) | 2013-09-30 |
IL195253A0 (en) | 2009-08-03 |
US8110691B2 (en) | 2012-02-07 |
EA015302B1 (ru) | 2011-06-30 |
CA2653552C (en) | 2013-04-23 |
AU2007258955B2 (en) | 2012-09-20 |
HUP0600491A2 (en) | 2008-02-28 |
WO2007144674A1 (en) | 2007-12-21 |
EA200900015A1 (ru) | 2009-04-28 |
ZA200809799B (en) | 2009-11-25 |
US20090187032A1 (en) | 2009-07-23 |
HU227112B1 (hu) | 2010-07-28 |
MX2008015972A (es) | 2009-01-12 |
ES2409841T3 (es) | 2013-06-28 |
BRPI0713157A2 (pt) | 2012-04-03 |
SI2027140T1 (sl) | 2013-07-31 |
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