KR20100017780A - 17베타-시아노-18ａ-호모-19-노르-안드로스트-4-엔 유도체, 그의 용도, 및 상기 유도체를 함유하는 의약 - Google Patents
17베타-시아노-18ａ-호모-19-노르-안드로스트-4-엔 유도체, 그의 용도, 및 상기 유도체를 함유하는 의약 Download PDFInfo
- Publication number
- KR20100017780A KR20100017780A KR1020097025931A KR20097025931A KR20100017780A KR 20100017780 A KR20100017780 A KR 20100017780A KR 1020097025931 A KR1020097025931 A KR 1020097025931A KR 20097025931 A KR20097025931 A KR 20097025931A KR 20100017780 A KR20100017780 A KR 20100017780A
- Authority
- KR
- South Korea
- Prior art keywords
- homo
- cyano
- androst
- methylene
- methyl
- 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- Withdrawn
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 39
- 239000001257 hydrogen Substances 0.000 claims abstract description 39
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- 230000003152 gestagenic effect Effects 0.000 claims abstract description 14
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 14
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 238000006664 bond formation reaction Methods 0.000 claims abstract description 10
- -1 hydroxymethylene Chemical group 0.000 claims abstract description 9
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 150000004677 hydrates Chemical class 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 239000012453 solvate Substances 0.000 claims abstract description 6
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 5
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- 150000002367 halogens Chemical class 0.000 claims abstract description 5
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 4
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- 238000011282 treatment Methods 0.000 claims description 11
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- RKHQGWMMUURILY-UHRZLXHJSA-N cortivazol Chemical compound C([C@H]1[C@@H]2C[C@H]([C@]([C@@]2(C)C[C@H](O)[C@@H]1[C@@]1(C)C2)(O)C(=O)COC(C)=O)C)=C(C)C1=CC1=C2C=NN1C1=CC=CC=C1 RKHQGWMMUURILY-UHRZLXHJSA-N 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
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- RSEPBGGWRJCQGY-RBRWEJTLSA-N Estradiol valerate Chemical compound C1CC2=CC(O)=CC=C2[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CCCC)[C@@]1(C)CC2 RSEPBGGWRJCQGY-RBRWEJTLSA-N 0.000 claims description 2
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 238000004128 high performance liquid chromatography Methods 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 238000000926 separation method Methods 0.000 description 15
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- 238000006243 chemical reaction Methods 0.000 description 7
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- C—CHEMISTRY; METALLURGY
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- 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
- C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
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- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/12—Drugs for genital or sexual disorders; Contraceptives for climacteric disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
-
- 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
-
- 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
-
- 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
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/30—Oestrogens
-
- 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
- A61P5/34—Gestagens
-
- 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
- A61P5/42—Drugs for disorders of the endocrine system of the suprarenal hormones for decreasing, blocking or antagonising the activity of mineralocorticosteroids
-
- 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
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
- C07J53/004—3 membered carbocyclic rings
- C07J53/007—3 membered carbocyclic rings in position 6-7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
- C07J53/004—3 membered carbocyclic rings
- C07J53/008—3 membered carbocyclic rings in position 15/16
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Reproductive Health (AREA)
- Gynecology & Obstetrics (AREA)
- Toxicology (AREA)
- Pregnancy & Childbirth (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007027636A DE102007027636A1 (de) | 2007-06-12 | 2007-06-12 | 17ß-Cyano-18a-homo-19-nor-androst-4-en-Derivat, dessen Verwendung und das Derivat enthaltende Arzneimittel |
| DE102007027636.4 | 2007-06-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20100017780A true KR20100017780A (ko) | 2010-02-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020097025931A Withdrawn KR20100017780A (ko) | 2007-06-12 | 2008-06-04 | 17베타-시아노-18ａ-호모-19-노르-안드로스트-4-엔 유도체, 그의 용도, 및 상기 유도체를 함유하는 의약 |
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| EP (1) | EP2178899B1 (enExample) |
| JP (1) | JP2010529152A (enExample) |
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| CN (1) | CN101679477A (enExample) |
| AR (1) | AR066970A1 (enExample) |
| AU (1) | AU2008261277A1 (enExample) |
| BR (1) | BRPI0813455A2 (enExample) |
| CA (1) | CA2689563A1 (enExample) |
| CL (1) | CL2008001721A1 (enExample) |
| DE (1) | DE102007027636A1 (enExample) |
| ES (1) | ES2397879T3 (enExample) |
| IL (1) | IL202300A0 (enExample) |
| MX (1) | MX2009013626A (enExample) |
| PA (1) | PA8784201A1 (enExample) |
| PE (1) | PE20090312A1 (enExample) |
| RU (1) | RU2010100334A (enExample) |
| TW (1) | TW200906846A (enExample) |
| UY (1) | UY31145A1 (enExample) |
| WO (1) | WO2008151745A1 (enExample) |
| ZA (1) | ZA201000185B (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2010066354A1 (de) * | 2008-12-12 | 2010-06-17 | Bayer Schering Pharma Aktiengesellschaft | VERWENDUNG VON 17β-CYANO-18A-HOMO-19-NOR-ANDROST-4-EN-DERIVATEN ZUR HERSTELLUNG EINES ARZNEIMITTELS IN DEPOT-FORM ZUR PARENTERALEN ANWENDUNG SOWIE DEPOT-ARZNEIMITTEL ENTHALTEND 17β-CYANO-18A-HOMO-19-NOR-ANDROST-4-EN-DERIVATE ZUR PARENTERALEN ANWENDUNG |
| WO2012059594A1 (en) | 2010-11-04 | 2012-05-10 | Bayer Pharma Aktiengesellschaft | Mineralcorticoid receptor antagonists for the treatment of corticoid-induced obesity |
| US9388210B2 (en) | 2011-02-25 | 2016-07-12 | Washington University | Neuroactive 17(20)-Z-vinylcyano-substituted steroids, prodrugs thereof, and methods of treatment using same |
| CN104136452A (zh) | 2011-10-14 | 2014-11-05 | 萨奇治疗股份有限公司 | 3,3-二取代的19-去甲孕甾烷化合物、组合物、及其用途 |
| RS57390B1 (sr) | 2012-12-18 | 2018-09-28 | Univ Washington | Neuroaktivni 19-alkoksi-17-supstituisani steroidi, primenjivi u postupcima lečenja |
| US9512170B2 (en) | 2013-03-01 | 2016-12-06 | Washington University | Neuroactive 13, 17-substituted steroids as modulators for GABA type-A receptors |
| US9365502B2 (en) | 2013-03-11 | 2016-06-14 | Washington University | Neuroactive substituted cyclopenta[b]phenanthrenes as modulators for GABA type-A receptors |
| US9562026B2 (en) | 2013-03-14 | 2017-02-07 | Washington University | Neuroactive substituted cyclopent[a]anthracenes as modulators for GABA type-A receptors |
| US9725481B2 (en) | 2013-04-17 | 2017-08-08 | Sage Therapeutics, Inc. | 19-nor C3, 3-disubstituted C21-C-bound heteroaryl steroids and methods of use thereof |
| WO2014169836A1 (en) | 2013-04-17 | 2014-10-23 | Sage Therapeutics, Inc. | 19-nor neuroactive steroids and methods of use thereof |
| EP2986623B1 (en) | 2013-04-17 | 2018-11-07 | Sage Therapeutics, Inc. | 19-nor c3,3-disubstituted c21-n-pyrazolyl steroids and methods of use thereof |
| SI2986624T1 (sl) | 2013-04-17 | 2020-10-30 | Sage Therapeutics, Inc. | 19-nor nevroaktivni steroidi za metode zdravljenja |
| SI3021852T1 (sl) | 2013-07-19 | 2021-07-30 | Sage Therapeutics, Inc. | Nevroaktivni steroidi, sestavki in uporabe le-teh |
| JP6466942B2 (ja) | 2013-08-23 | 2019-02-06 | セージ セラピューティクス， インコーポレイテッド | 向神経活性ステロイド、組成物、及びその使用 |
| WO2015195962A1 (en) | 2014-06-18 | 2015-12-23 | Sage Therapeutics, Inc. | Neuroactive steroids, compositions, and uses thereof |
| RS60642B1 (sr) | 2014-10-16 | 2020-09-30 | Sage Therapeutics Inc | Kompozicije i postupci za lečenje poremećaja cns-a |
| EP4527461A3 (en) | 2014-10-16 | 2025-06-25 | Sage Therapeutics, Inc. | A compound, compositions thereof and this compound for use in methods of treating cns disorders |
| SMT202000276T1 (it) | 2014-11-27 | 2020-07-08 | Sage Therapeutics Inc | Composizioni e metodi per trattare disturbi del snc |
| SMT202100113T1 (it) | 2015-01-26 | 2021-05-07 | Sage Therapeutics Inc | Composizioni e metodi per trattare disturbi del snc |
| JP6875996B2 (ja) | 2015-02-20 | 2021-05-26 | セージ セラピューティクス， インコーポレイテッド | 神経刺激性ステロイド、組成物、およびその使用 |
| NZ790187A (en) | 2016-07-11 | 2025-08-29 | Sage Therapeutics Inc | C7, C12, and C16 substituted neuroactive steroids and their methods of use |
| IL264129B2 (en) | 2016-07-11 | 2024-05-01 | Sage Therapeutics Inc | C17, c20, and c21 substituted neuroactive steroids and their methods of use |
| SG11202112391UA (en) | 2019-05-31 | 2021-12-30 | Sage Therapeutics Inc | Neuroactive steroids and compositions thereof |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3043833A (en) * | 1961-07-14 | 1962-07-10 | Ormonoterapia Richter Spa | 17-cyanohydrin of 19-nor androstenedione and 3-derivatives thereof |
| DE1183500B (de) | 1962-10-12 | 1964-12-17 | Schering Ag | Verfahren zur Herstellung von alpha, beta-Methylenketonen der Steroidreihe |
| US3579509A (en) * | 1965-06-21 | 1971-05-18 | Smith Kline French Lab | Process and 6-beta-substituted ethyl intermediates for preparing 6,6-ethylene-3-keto-delta**4 steroids |
| GB1089945A (en) * | 1965-09-23 | 1967-11-08 | British Drug Houses Ltd | Steroidal-6-spirocyclopropyl-4-en-3-ones |
| IL32699A (en) * | 1968-07-30 | 1973-06-29 | American Home Prod | 6-substituted-13-polycarbonalkyl-18,19 dinorpregn-4-en-3-ones,their preparation and pharmaceutical compositions containing them |
| FR2081561B1 (enExample) * | 1970-03-03 | 1973-04-06 | Roussel Uclaf | |
| US3705179A (en) | 1971-03-15 | 1972-12-05 | American Home Prod | Antiandrogenic steroids |
| FR2139708B1 (enExample) | 1971-06-01 | 1974-08-23 | Roussel Uclaf | |
| US3994937A (en) * | 1972-02-11 | 1976-11-30 | Schering Aktiengesellschaft | 15α,16α-Methylene-4-estren-17β-ols |
| BE795241A (fr) | 1972-02-11 | 1973-08-09 | Schering Ag | 15alpha, 16alpha-methylene-4-oestren-17beta-ols-methylenz-4-oestren-17beta-ols et leur procede de preparation |
| NL7701384A (nl) | 1977-02-10 | 1978-08-14 | Akzo Nv | Werkwijze voor het bereiden van nieuwe steroiden van de oestraanreeks. |
| DE2922500A1 (de) | 1979-05-31 | 1980-12-04 | Schering Ag | 6 beta .7 beta |
| US4252800A (en) * | 1979-10-05 | 1981-02-24 | United States Of America | 7α-methylnorethindrone enanthate and its use in long term suppression of fertility in female mammals |
| US4544554A (en) * | 1983-09-26 | 1985-10-01 | Ortho Pharmaceutical Corporation | Triphasic oral contraceptive |
| DE3402329A1 (de) | 1984-01-20 | 1985-08-01 | Schering AG, 1000 Berlin und 4709 Bergkamen | 6,6-ethylen-15,16-methylen-3-oxo-17(alpha)-pregn-4-en-21,17-carbolactone, verfahren zu deren herstellung und diese enthaltende pharmazeutische praeparate |
| DE4344462C2 (de) * | 1993-12-22 | 1996-02-01 | Schering Ag | Zusammensetzung für die Empfängnisverhütung |
| EP0785211A1 (en) * | 1996-01-22 | 1997-07-23 | Laboratoire Theramex | New substituted 19-nor-pregnane derivatives |
| DE19651000A1 (de) | 1996-12-01 | 1998-06-04 | Schering Ag | Oxyiminopregnancarbolactone |
| DE102004063864A1 (de) | 2004-12-30 | 2006-07-13 | Schering Ag | 18-Methyl-19-nor-17-pregn-4-en21,17-carbolactone, sowie diese enthaltende pharmazeutische Präparate |
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2007
- 2007-06-12 DE DE102007027636A patent/DE102007027636A1/de not_active Withdrawn
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2008
- 2008-06-04 KR KR1020097025931A patent/KR20100017780A/ko not_active Withdrawn
- 2008-06-04 AU AU2008261277A patent/AU2008261277A1/en not_active Abandoned
- 2008-06-04 MX MX2009013626A patent/MX2009013626A/es not_active Application Discontinuation
- 2008-06-04 JP JP2010511525A patent/JP2010529152A/ja active Pending
- 2008-06-04 ES ES08758989T patent/ES2397879T3/es active Active
- 2008-06-04 BR BRPI0813455-3A2A patent/BRPI0813455A2/pt not_active Application Discontinuation
- 2008-06-04 EP EP08758989A patent/EP2178899B1/de not_active Not-in-force
- 2008-06-04 CN CN200880020040A patent/CN101679477A/zh active Pending
- 2008-06-04 WO PCT/EP2008/004428 patent/WO2008151745A1/de not_active Ceased
- 2008-06-04 CA CA002689563A patent/CA2689563A1/en not_active Abandoned
- 2008-06-04 RU RU2010100334/04A patent/RU2010100334A/ru not_active Application Discontinuation
- 2008-06-11 TW TW097121799A patent/TW200906846A/zh unknown
- 2008-06-11 US US12/137,122 patent/US20090048218A1/en not_active Abandoned
- 2008-06-11 PA PA20088784201A patent/PA8784201A1/es unknown
- 2008-06-11 UY UY31145A patent/UY31145A1/es not_active Application Discontinuation
- 2008-06-11 PE PE2008000992A patent/PE20090312A1/es not_active Application Discontinuation
- 2008-06-11 CL CL2008001721A patent/CL2008001721A1/es unknown
- 2008-06-12 AR ARP080102498A patent/AR066970A1/es unknown
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2009
- 2009-11-24 IL IL202300A patent/IL202300A0/en unknown
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2010
- 2010-01-11 ZA ZA2010/00185A patent/ZA201000185B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PE20090312A1 (es) | 2009-04-09 |
| PA8784201A1 (es) | 2009-01-23 |
| ES2397879T3 (es) | 2013-03-12 |
| CA2689563A1 (en) | 2008-12-18 |
| AU2008261277A1 (en) | 2008-12-18 |
| CL2008001721A1 (es) | 2008-12-19 |
| AR066970A1 (es) | 2009-09-23 |
| ZA201000185B (en) | 2011-03-30 |
| WO2008151745A1 (de) | 2008-12-18 |
| US20090048218A1 (en) | 2009-02-19 |
| EP2178899B1 (de) | 2012-10-24 |
| DE102007027636A1 (de) | 2008-12-18 |
| EP2178899A1 (de) | 2010-04-28 |
| UY31145A1 (es) | 2009-01-30 |
| TW200906846A (en) | 2009-02-16 |
| JP2010529152A (ja) | 2010-08-26 |
| RU2010100334A (ru) | 2011-07-20 |
| IL202300A0 (en) | 2010-06-30 |
| BRPI0813455A2 (pt) | 2014-12-23 |
| CN101679477A (zh) | 2010-03-24 |
| MX2009013626A (es) | 2010-01-20 |
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Patent event date: 20091211 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |