CO6210749A2 - Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor adrenergico beta2 - Google Patents
Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor adrenergico beta2Info
- Publication number
- CO6210749A2 CO6210749A2 CO10063946A CO10063946A CO6210749A2 CO 6210749 A2 CO6210749 A2 CO 6210749A2 CO 10063946 A CO10063946 A CO 10063946A CO 10063946 A CO10063946 A CO 10063946A CO 6210749 A2 CO6210749 A2 CO 6210749A2
- Authority
- CO
- Colombia
- Prior art keywords
- attached
- group
- atom
- carbon atom
- phenyl ring
- Prior art date
Links
- 230000001800 adrenalinergic effect Effects 0.000 title 1
- 239000000556 agonist Substances 0.000 title 1
- QHGUCRYDKWKLMG-UHFFFAOYSA-N octopamine Chemical class NCC(O)C1=CC=C(O)C=C1 QHGUCRYDKWKLMG-UHFFFAOYSA-N 0.000 title 1
- 229910052799 carbon Inorganic materials 0.000 abstract 9
- 125000004432 carbon atom Chemical group C* 0.000 abstract 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- 229910052757 nitrogen Inorganic materials 0.000 abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- -1 1-adamantyl Chemical group 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
Classifications
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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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
-
- 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
- A61P15/06—Antiabortive agents; Labour repressants
-
- 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
-
- 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
- A61P27/06—Antiglaucoma agents or miotics
-
- 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
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/60—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/42—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/43—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Ophthalmology & Optometry (AREA)
- Epidemiology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Emergency Medicine (AREA)
- Pregnancy & Childbirth (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Gynecology & Obstetrics (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
Abstract
1.- Un compuesto de fórmula (I):en donde: ° R1 es un grupo seleccionado de -CH2OH, -NH(CO)H y ° R2 es un átomo de hidrógeno; o ° R1 junto con R2 forman el grupo -NH-C(O)-CH=CH-, en donde el átomo de nitrógeno está unido al átomo de carbono del anillo de fenilo al que está unido R1 y el átomo de carbono está unido al átomo de carbono del anillo de fenilo al que está unido R2 ° R3a y R3b se seleccionan independientemente del grupo que consiste en átomos de hidrógeno y grupos alquilo C1-4, ° n representa un número entero de 1 a 3; ° Ad representa un grupo 1-adamantilo o 2-adamantilo, o una de sus sales o solvatos o éstereoisómeros farmacéuticamente aceptables. 2.- Un compuesto de acuerdo con la reivindicación 1, en donde R1 representa un grupo -NH(CO)H y R2 es un átomo de hidrógeno; o R1 junto con R2 forman el grupo -NH-C(O)-CH=CH, en donde el átomo de nitrógeno está unido al átomo de carbono del anillo de fenilo al que está unido R1 y el átomo de carbono está unido al átomo de carbono del anillo de fenilo al que está unido R2. 3.- Un compuesto de acuerdo con la reivindicación 2, en donde R1 junto con R2 forman el grupo -NH-C(O)-CH=CH-, en donde el átomo de nitrógeno está unido al átomo de carbono del anillo de fenilo al que está unido R1 y el átomo de carbono está unido al átomo de carbono del anillo de fenilo al que está unido R2. 4.- Un compuesto de acuerdo con cualquiera de las reivindicaciones precedentes, en donde R3a y R3b se seleccionan independientemente del grupo que consiste en átomos de hidrógeno y grupos metilo. 5.- Un compuesto de acuerdo con la reivindicación 4, en donde R3a representa un átomo de hidrógeno y R3b se selecciona del grupo que consiste en átomos de hidrógeno y grupos metilo.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES200703157A ES2320961B1 (es) | 2007-11-28 | 2007-11-28 | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor adrenergico beta2. |
Publications (1)
Publication Number | Publication Date |
---|---|
CO6210749A2 true CO6210749A2 (es) | 2010-10-20 |
Family
ID=40451169
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CO10063946A CO6210749A2 (es) | 2007-11-28 | 2010-05-27 | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor adrenergico beta2 |
Country Status (20)
Country | Link |
---|---|
US (1) | US8178679B2 (es) |
EP (1) | EP2212276A1 (es) |
JP (1) | JP2011505343A (es) |
KR (1) | KR20100090248A (es) |
CN (1) | CN101815700A (es) |
AR (1) | AR069735A1 (es) |
AU (1) | AU2008329193A1 (es) |
BR (1) | BRPI0816597A2 (es) |
CA (1) | CA2706333A1 (es) |
CL (1) | CL2008003494A1 (es) |
CO (1) | CO6210749A2 (es) |
ES (1) | ES2320961B1 (es) |
MX (1) | MX2010005623A (es) |
NZ (1) | NZ583993A (es) |
PE (1) | PE20091070A1 (es) |
RU (1) | RU2010126063A (es) |
TW (1) | TW200927111A (es) |
UY (1) | UY31439A1 (es) |
WO (1) | WO2009068177A1 (es) |
ZA (1) | ZA201001818B (es) |
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2265276B1 (es) | 2005-05-20 | 2008-02-01 | Laboratorios Almirall S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor beta2 adrenergico. |
ES2296516B1 (es) * | 2006-04-27 | 2009-04-01 | Laboratorios Almirall S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor beta2 adrenergico. |
ES2306595B1 (es) * | 2007-02-09 | 2009-09-11 | Laboratorios Almirall S.A. | Sal de napadisilato de 5-(2-((6-(2,2-difluoro-2-feniletoxi)hexil)amino)-1-hidroxietil)-8-hidroxiquinolin-2(1h)-ona como agonista del receptor adrenergico beta2. |
UY32297A (es) | 2008-12-22 | 2010-05-31 | Almirall Sa | Sal mesilato de 5-(2-{[6-(2,2-difluoro-2-fenilitoxi) hexil]amino}-1-hidroxietil)-8-hidroxiquinolin-2( 1h)-ona como agonista del receptor b(beta)2 acrenérgico |
EP2228368A1 (en) | 2009-03-12 | 2010-09-15 | Almirall, S.A. | Process for manufacturing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy) hexyl]amino}-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one |
EP2457900A1 (en) | 2010-11-25 | 2012-05-30 | Almirall, S.A. | New pyrazole derivatives having CRTh2 antagonistic behaviour |
EP2463289A1 (en) | 2010-11-26 | 2012-06-13 | Almirall, S.A. | Imidazo[1,2-b]pyridazine derivatives as JAK inhibitors |
EP2518070A1 (en) | 2011-04-29 | 2012-10-31 | Almirall, S.A. | Pyrrolotriazinone derivatives as PI3K inhibitors |
EP2518071A1 (en) | 2011-04-29 | 2012-10-31 | Almirall, S.A. | Imidazopyridine derivatives as PI3K inhibitors |
EP2527344A1 (en) | 2011-05-25 | 2012-11-28 | Almirall, S.A. | Pyridin-2(1H)-one derivatives useful as medicaments for the treatment of myeloproliferative disorders, transplant rejection, immune-mediated and inflammatory diseases |
EP2526945A1 (en) | 2011-05-25 | 2012-11-28 | Almirall, S.A. | New CRTH2 Antagonists |
EP2548876A1 (en) | 2011-07-18 | 2013-01-23 | Almirall, S.A. | New CRTh2 antagonists |
EP2548863A1 (en) | 2011-07-18 | 2013-01-23 | Almirall, S.A. | New CRTh2 antagonists. |
EP2554544A1 (en) | 2011-08-01 | 2013-02-06 | Almirall, S.A. | Pyridin-2(1h)-one derivatives as jak inhibitors |
EP2578570A1 (en) | 2011-10-07 | 2013-04-10 | Almirall, S.A. | Novel process for preparing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1(r)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one via novel intermediates of synthesis. |
EP2641900A1 (en) | 2012-03-20 | 2013-09-25 | Almirall, S.A. | Novel polymorphic Crystal forms of 5-(2-{[6-(2,2-difluoro-2-phenylethoxy) hexyl]amino}-1-(R)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one, heminapadisylate as agonist of the ß2 adrenergic receptor. |
WO2014060431A1 (en) | 2012-10-16 | 2014-04-24 | Almirall, S.A. | Pyrrolotriazinone derivatives as pi3k inhibitors |
EP2738172A1 (en) | 2012-11-28 | 2014-06-04 | Almirall, S.A. | New bicyclic compounds as crac channel modulators |
CN105142673B8 (zh) | 2012-12-18 | 2018-02-16 | 阿尔米雷尔有限公司 | 具有β2肾上腺素能激动剂及M3毒蕈碱拮抗剂活性的新型环己基和奎宁环基氨基甲酸酯衍生物 |
UY35332A (es) | 2013-02-15 | 2014-11-28 | Almirall Sa | Derivados de pirrolotriazina como inhibidores de pi3k |
EP2848615A1 (en) | 2013-07-03 | 2015-03-18 | Almirall, S.A. | New pyrazole derivatives as CRAC channel modulators |
AU2016279330B2 (en) | 2015-06-16 | 2020-05-14 | Jiangsu Hengrui Medicine Co., Ltd. | Piperidine derivative and preparation method and pharmaceutical use thereof |
WO2018011090A1 (en) * | 2016-07-13 | 2018-01-18 | Chiesi Farmaceutici S.P.A. | Hydroxyquinolinone compounds having muscarinic receptor antagonist and beta2 adrenergic receptor agonist activity |
CN106631717B (zh) * | 2016-11-17 | 2019-11-22 | 上海再启生物技术有限公司 | 一种3-(2-氨基丙基)苯酚的制备方法 |
AU2017444990B2 (en) * | 2017-12-27 | 2022-12-01 | Carlos Batthyány | Nitroalkene non steroidal anti-inflammatory drugs (NA-NSAIDs) and methods of treating inflammation related conditions |
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-
2007
- 2007-11-28 ES ES200703157A patent/ES2320961B1/es not_active Withdrawn - After Issue
-
2008
- 2008-10-28 UY UY31439A patent/UY31439A1/es unknown
- 2008-11-10 JP JP2010535263A patent/JP2011505343A/ja active Pending
- 2008-11-10 AU AU2008329193A patent/AU2008329193A1/en not_active Abandoned
- 2008-11-10 US US12/745,195 patent/US8178679B2/en not_active Expired - Fee Related
- 2008-11-10 CN CN200880110363A patent/CN101815700A/zh active Pending
- 2008-11-10 MX MX2010005623A patent/MX2010005623A/es active IP Right Grant
- 2008-11-10 WO PCT/EP2008/009469 patent/WO2009068177A1/en active Application Filing
- 2008-11-10 NZ NZ583993A patent/NZ583993A/en not_active IP Right Cessation
- 2008-11-10 TW TW097143392A patent/TW200927111A/zh unknown
- 2008-11-10 CA CA2706333A patent/CA2706333A1/en not_active Abandoned
- 2008-11-10 EP EP08853662A patent/EP2212276A1/en not_active Withdrawn
- 2008-11-10 KR KR1020107010118A patent/KR20100090248A/ko not_active Application Discontinuation
- 2008-11-10 RU RU2010126063/04A patent/RU2010126063A/ru not_active Application Discontinuation
- 2008-11-10 BR BRPI0816597-1A2A patent/BRPI0816597A2/pt not_active IP Right Cessation
- 2008-11-24 CL CL2008003494A patent/CL2008003494A1/es unknown
- 2008-11-26 PE PE2008001979A patent/PE20091070A1/es not_active Application Discontinuation
- 2008-11-26 AR ARP080105121A patent/AR069735A1/es unknown
-
2010
- 2010-03-15 ZA ZA2010/01818A patent/ZA201001818B/en unknown
- 2010-05-27 CO CO10063946A patent/CO6210749A2/es not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
NZ583993A (en) | 2011-11-25 |
ZA201001818B (en) | 2010-12-29 |
CN101815700A (zh) | 2010-08-25 |
RU2010126063A (ru) | 2012-01-10 |
CL2008003494A1 (es) | 2010-01-04 |
AR069735A1 (es) | 2010-02-17 |
UY31439A1 (es) | 2009-04-30 |
US8178679B2 (en) | 2012-05-15 |
ES2320961B1 (es) | 2010-03-17 |
TW200927111A (en) | 2009-07-01 |
CA2706333A1 (en) | 2009-06-04 |
PE20091070A1 (es) | 2009-07-23 |
US20100324000A1 (en) | 2010-12-23 |
BRPI0816597A2 (pt) | 2015-03-03 |
KR20100090248A (ko) | 2010-08-13 |
AU2008329193A1 (en) | 2009-06-04 |
WO2009068177A1 (en) | 2009-06-04 |
ES2320961A1 (es) | 2009-05-29 |
JP2011505343A (ja) | 2011-02-24 |
MX2010005623A (es) | 2010-06-01 |
EP2212276A1 (en) | 2010-08-04 |
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