BRPI0413667A - Processo para a preparação de 4-amino-3-carbonitrilas de quinolina - Google Patents
Processo para a preparação de 4-amino-3-carbonitrilas de quinolinaInfo
- Publication number
- BRPI0413667A BRPI0413667A BRPI0413667-5A BRPI0413667A BRPI0413667A BR PI0413667 A BRPI0413667 A BR PI0413667A BR PI0413667 A BRPI0413667 A BR PI0413667A BR PI0413667 A BRPI0413667 A BR PI0413667A
- Authority
- BR
- Brazil
- Prior art keywords
- amino
- quinoline
- carbonitrile
- cyanoacetamide
- combining
- Prior art date
Links
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title abstract 10
- 238000000034 method Methods 0.000 title abstract 5
- 238000002360 preparation method Methods 0.000 title abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 6
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 abstract 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 4
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 abstract 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 4
- FRBZBJHKHSVFNK-UHFFFAOYSA-N 3-amino-2-cyanoprop-2-enamide Chemical compound NC=C(C#N)C(N)=O FRBZBJHKHSVFNK-UHFFFAOYSA-N 0.000 abstract 3
- 230000001476 alcoholic effect Effects 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 2
- -1 amine compound Chemical class 0.000 abstract 2
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 239000000725 suspension Substances 0.000 abstract 2
- 239000008096 xylene Substances 0.000 abstract 2
- VBMNWPOIPHHUSC-UHFFFAOYSA-N 4-aminoquinoline-3-carbonitrile Chemical compound C1=CC=C2C(N)=C(C#N)C=NC2=C1 VBMNWPOIPHHUSC-UHFFFAOYSA-N 0.000 abstract 1
- DFVGZQAGEWKYEW-UHFFFAOYSA-N 7-aminothieno[3,2-b]pyridine-6-carbonitrile Chemical compound NC1=C(C#N)C=NC2=C1SC=C2 DFVGZQAGEWKYEW-UHFFFAOYSA-N 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000012026 peptide coupling reagents Substances 0.000 abstract 1
- DKGYESBFCGKOJC-UHFFFAOYSA-N thiophen-3-amine Chemical compound NC=1C=CSC=1 DKGYESBFCGKOJC-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61K31/275—Nitriles; Isonitriles
-
- 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
- A61K31/47—Quinolines; Isoquinolines
-
- 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4706—4-Aminoquinolines; 8-Aminoquinolines, e.g. chloroquine, primaquine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
-
- 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Materials Engineering (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
Abstract
"PROCESSO PARA A PREPARAçãO DE 4-AMINO-3-CARBONITRILAS DE QUINOLINA". A presente invenção refere-se a um processo para a preparação de uma 4-amino-3-carbonitrila de quinolina, que compreende combinar um composto amina com um ácido cianoacético e um catalisador ácido para obter uma cianoacetamida; condensar a cianoacetamida com uma anilina opcionalmente até tetrassubstituída em um solvente alcoólico e um ortoformiato de trialquila para produzir uma 2-amino-2-cianoacrilamida; combinar a 3-amino-2-cianoacrilamida com oxicloreto de fósforo em acetonitrila, butironitrila, tolueno ou xileno, opcionalmente em presença de um catalisador para produzir uma 4-amino-3-carbonitrila de quinolina e igualmente descreve um processo para a preparação de uma 7-amino-tieno¢3,2-b!piridina-6-carbonitrila compreendendo combinar um 3-amino tiofeno com uma cianoacetamida e ortoformiato de trialquila em um solvente alcoólico para obter uma 3-amino-2-cianoacrilamida; e combinar a 3-amino-2-cianoacrilamida com oxicloreto de fósforo e acetonitrila, butironitrila, tolueno ou xileno, opcionalmente em presença de um catalisador para produzir uma 7-aminotieno¢3,2-b!piridina-6-carbonitrila e igualmente descreve um processo para a preparação de uma 4 amino-3-carbonitrila de quinolina compreendendo combinar um composto amina com ácido cianoacético e um reagente de acoplamento peptídico para obter uma suspensão, filtrar a suspensão; para obter cianoacetamida; condensar a clanoacetamida com uma anilina opcionalmente até tetrassubstituída com um solvente alcoólico para obter uma 4-amino-3-carbonitrila de quinolina, e a invenção descreve um processo para obter uma cianoacetamida.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49619103P | 2003-08-19 | 2003-08-19 | |
| PCT/US2004/026329 WO2005019201A2 (en) | 2003-08-19 | 2004-08-13 | Process for the preparation of 4-amino-3-quinolinecarbonitriles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0413667A true BRPI0413667A (pt) | 2006-10-24 |
Family
ID=34215972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0413667-5A BRPI0413667A (pt) | 2003-08-19 | 2004-08-13 | Processo para a preparação de 4-amino-3-carbonitrilas de quinolina |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US7297795B2 (pt) |
| EP (1) | EP1660453A2 (pt) |
| JP (1) | JP2007502819A (pt) |
| KR (1) | KR20060066733A (pt) |
| CN (1) | CN1835923A (pt) |
| AR (1) | AR045277A1 (pt) |
| AU (1) | AU2004267061A1 (pt) |
| BR (1) | BRPI0413667A (pt) |
| CA (1) | CA2535385A1 (pt) |
| CO (1) | CO5670369A2 (pt) |
| CR (1) | CR8226A (pt) |
| EC (1) | ECSP066384A (pt) |
| GT (1) | GT200400165A (pt) |
| IL (1) | IL173456A0 (pt) |
| MX (1) | MXPA06001590A (pt) |
| MY (1) | MY140542A (pt) |
| NO (1) | NO20060539L (pt) |
| PA (1) | PA8609301A1 (pt) |
| PE (1) | PE20050344A1 (pt) |
| RU (1) | RU2345069C2 (pt) |
| SA (1) | SA04250258B1 (pt) |
| SG (1) | SG145744A1 (pt) |
| SV (1) | SV2005001855A (pt) |
| TW (1) | TW200517378A (pt) |
| WO (1) | WO2005019201A2 (pt) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7479561B2 (en) | 2004-08-16 | 2009-01-20 | Wyeth | 4-(2,4-dichloro-5-methoxyphenyl)amino-6-methoxy-7-{[5-substituted-amino)methyl]-3-furyl}-3-quinolinecarbonitriles as kinase inhibitors |
| CN108421044A (zh) | 2005-02-03 | 2018-08-21 | 综合医院公司 | 治疗吉非替尼耐药性癌症的方法 |
| EP1888529A2 (en) * | 2005-05-18 | 2008-02-20 | Wyeth | 3-cyanoquinoline inhibitors of tpl2 kinase and methods of making and using the same |
| CN101180269A (zh) * | 2005-05-25 | 2008-05-14 | 惠氏公司 | 制备3-氰基-喹啉的方法和由其制得的中间体 |
| BRPI0610147A2 (pt) * | 2005-05-25 | 2010-06-01 | Wyeth Corp | método para preparar e sintetizar 3-cianoquinolinas substituìdas e 4-amino-3-cianoquinolinas |
| RU2007140957A (ru) * | 2005-05-25 | 2009-06-27 | Вайет (Us) | Способы синтеза производных 6-алкиламинохинолинов |
| WO2007005462A1 (en) | 2005-07-01 | 2007-01-11 | Wyeth | Crystalline forms of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methyl-1-piperazinyl)propoxy]-3-quinolinecarb-onitrile and methods of preparing the same |
| BRPI0618042A2 (pt) | 2005-11-04 | 2011-08-16 | Wyeth Corp | usos de uma rapamicina e de uma herceptina, produto, pacote farmacêutico, e, composição farmacêutica |
| AU2007212756A1 (en) * | 2006-02-08 | 2007-08-16 | Wyeth | Preparation of 7-alkenyl-3 quinolinecarbonitriles via a palladium mediated coupling reaction |
| CN101195578B (zh) * | 2006-12-08 | 2012-04-25 | 上海睿智化学研究有限公司 | 1-(卤烷氧基)-2-烷氧基-5-硝基苯类化合物的合成方法 |
| US8022216B2 (en) | 2007-10-17 | 2011-09-20 | Wyeth Llc | Maleate salts of (E)-N-{4-[3-chloro-4-(2-pyridinylmethoxy)anilino]-3-cyano-7-ethoxy-6-quinolinyl}-4-(dimethylamino)-2-butenamide and crystalline forms thereof |
| CN102641270A (zh) | 2008-06-17 | 2012-08-22 | 惠氏有限责任公司 | 含有hki-272和长春瑞滨的抗肿瘤组合 |
| US8669273B2 (en) | 2008-08-04 | 2014-03-11 | Wyeth Llc | Antineoplastic combinations of 4-anilino-3-cyanoquinolines and capecitabine |
| WO2010030835A2 (en) * | 2008-09-11 | 2010-03-18 | Wyeth Llc | Pharmaceutical compositions of an src kinase inhibitor and an aromatase inhibitor |
| IL264349B2 (en) | 2009-04-06 | 2024-01-01 | Wyeth Llc | Regimen comprising neratinib for the treatment of cancer |
| RU2011152105A (ru) | 2009-07-02 | 2013-08-10 | УАЙТ ЭлЭлСи | Составы таблеток 3-цианохинолина и их применение |
| CN101792416B (zh) * | 2010-01-15 | 2011-10-05 | 南京医科大学 | 一种博舒替尼的制备工艺 |
| CA2803056C (en) * | 2010-06-23 | 2017-05-16 | Hanmi Science Co., Ltd. | Fused pyrimidine derivatives for inhibition of tyrosine kinase activity |
| WO2013187967A1 (en) | 2012-06-15 | 2013-12-19 | Institute For Cancer Research D/B/A The Research Institute Of Fox Case Cancer Center ("Fox Chase Cancer Center") | Sensitization of cancer cells to dna damage by inhibiting kinases essential for dna damage checkpoint control |
| CN102952037A (zh) * | 2012-11-18 | 2013-03-06 | 大连九信生物化工科技有限公司 | 一种2-氰基-n-(2,4-二氯-5-甲氧苯基)乙酰胺的合成方法 |
| WO2015123758A1 (en) * | 2014-02-20 | 2015-08-27 | Apotex Inc. | Bosutinib forms and preparation methods thereof |
| CN104876865A (zh) * | 2014-02-27 | 2015-09-02 | 南京正荣医药化学有限公司 | 一种博舒替尼的制备工艺 |
| KR20220129667A (ko) | 2015-07-06 | 2022-09-23 | 길리애드 사이언시즈, 인코포레이티드 | Cot 조정제 및 그의 사용 방법 |
| EP3319955B1 (en) * | 2015-07-06 | 2020-11-25 | Gilead Sciences, Inc. | 6-amino-quinoline-3-carbonitrils as cot modulators |
| CN105085398A (zh) * | 2015-09-06 | 2015-11-25 | 合肥华方医药科技有限公司 | 一种博舒替尼异构体杂质的制备方法 |
| CN105646345A (zh) * | 2016-03-16 | 2016-06-08 | 浙江海正药业股份有限公司 | 博舒替尼的新晶型及其制备方法 |
| ES2800339T3 (es) | 2016-06-30 | 2020-12-29 | Gilead Sciences Inc | 4,6-diaminoquinazolinas como moduladores de cuna y métodos de uso de los mismos |
| US11407734B2 (en) | 2017-10-18 | 2022-08-09 | Jiangsu Hengrui Medicine Co., Ltd. | Preparation method for tyrosine kinase inhibitor and intermediate thereof |
| CN108084085B (zh) * | 2017-12-28 | 2019-11-26 | 山东铂源药业有限公司 | 一种n-(3-氯-4-(2-吡啶甲氧基)苯基)-2-氰基乙酰胺的制备方法 |
| WO2019186429A1 (en) * | 2018-03-30 | 2019-10-03 | Sun Pharmaceutical Industries Limited | A process for the preparation of bosutinib |
| CN109180578B (zh) * | 2018-10-19 | 2020-06-26 | 山东创新药物研发有限公司 | 一种博舒替尼的制备方法 |
| CN111646955B (zh) * | 2019-03-04 | 2024-05-24 | 鲁南制药集团股份有限公司 | 一种制备博舒替尼中间体的方法 |
| CN111646939A (zh) * | 2019-03-04 | 2020-09-11 | 鲁南制药集团股份有限公司 | 一种博舒替尼的制备方法 |
| TWI915558B (zh) | 2019-06-14 | 2026-02-21 | 美商基利科學股份有限公司 | Cot 調節劑及其使用方法 |
| KR102924836B1 (ko) | 2020-03-30 | 2026-02-09 | 길리애드 사이언시즈, 인코포레이티드 | Cot 억제제 화합물, (S)-6-(((1-(바이사이클로[1.1.1]펜탄-1-일)-1H-1,2,3-트라이아졸-4-일)2-메틸-1-옥소-1,2-다이하이드로아이소퀴놀린-5-일)메틸)))아미노8-클로로-(네오펜틸아미노)퀴놀린-3-카르보니트릴의 고체 형태 |
| TWI778562B (zh) | 2020-04-02 | 2022-09-21 | 美商基利科學股份有限公司 | 製備cot抑制劑化合物的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA73073C2 (uk) * | 1997-04-03 | 2005-06-15 | Уайт Холдінгз Корпорейшн | Заміщені 3-ціанохіноліни, спосіб їх одержання та фармацевтична композиція |
-
2004
- 2004-08-13 CA CA002535385A patent/CA2535385A1/en not_active Abandoned
- 2004-08-13 EP EP04781074A patent/EP1660453A2/en not_active Withdrawn
- 2004-08-13 BR BRPI0413667-5A patent/BRPI0413667A/pt not_active IP Right Cessation
- 2004-08-13 SG SG200806052-7A patent/SG145744A1/en unknown
- 2004-08-13 JP JP2006523942A patent/JP2007502819A/ja not_active Withdrawn
- 2004-08-13 AU AU2004267061A patent/AU2004267061A1/en not_active Abandoned
- 2004-08-13 KR KR1020067003360A patent/KR20060066733A/ko not_active Ceased
- 2004-08-13 MX MXPA06001590A patent/MXPA06001590A/es active IP Right Grant
- 2004-08-13 CN CNA2004800236697A patent/CN1835923A/zh active Pending
- 2004-08-13 WO PCT/US2004/026329 patent/WO2005019201A2/en not_active Ceased
- 2004-08-13 RU RU2006108524/04A patent/RU2345069C2/ru not_active IP Right Cessation
- 2004-08-16 US US10/918,947 patent/US7297795B2/en not_active Expired - Fee Related
- 2004-08-17 PE PE2004000794A patent/PE20050344A1/es not_active Application Discontinuation
- 2004-08-17 TW TW093124649A patent/TW200517378A/zh unknown
- 2004-08-18 AR ARP040102964A patent/AR045277A1/es unknown
- 2004-08-18 MY MYPI20043356A patent/MY140542A/en unknown
- 2004-08-19 PA PA20048609301A patent/PA8609301A1/es unknown
- 2004-08-19 SV SV2004001855A patent/SV2005001855A/es not_active Application Discontinuation
- 2004-08-19 GT GT200400165A patent/GT200400165A/es unknown
- 2004-08-21 SA SA04250258A patent/SA04250258B1/ar unknown
-
2006
- 2006-01-31 IL IL173456A patent/IL173456A0/en unknown
- 2006-02-02 NO NO20060539A patent/NO20060539L/no not_active Application Discontinuation
- 2006-02-02 CR CR8226A patent/CR8226A/es not_active Application Discontinuation
- 2006-02-15 CO CO06015094A patent/CO5670369A2/es unknown
- 2006-02-17 EC EC2006006384A patent/ECSP066384A/es unknown
-
2007
- 2007-10-05 US US11/973,259 patent/US20080033175A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| SG145744A1 (en) | 2008-09-29 |
| SV2005001855A (es) | 2005-11-04 |
| NO20060539L (no) | 2006-02-13 |
| KR20060066733A (ko) | 2006-06-16 |
| GT200400165A (es) | 2005-04-12 |
| RU2006108524A (ru) | 2007-09-27 |
| WO2005019201A3 (en) | 2005-08-04 |
| CA2535385A1 (en) | 2005-03-03 |
| CO5670369A2 (es) | 2006-08-31 |
| SA04250258B1 (ar) | 2009-01-07 |
| AU2004267061A1 (en) | 2005-03-03 |
| JP2007502819A (ja) | 2007-02-15 |
| AR045277A1 (es) | 2005-10-19 |
| RU2345069C2 (ru) | 2009-01-27 |
| MXPA06001590A (es) | 2006-05-19 |
| CR8226A (es) | 2008-08-21 |
| MY140542A (en) | 2009-12-31 |
| CN1835923A (zh) | 2006-09-20 |
| EP1660453A2 (en) | 2006-05-31 |
| ECSP066384A (es) | 2006-08-30 |
| PA8609301A1 (es) | 2005-03-03 |
| IL173456A0 (en) | 2006-06-11 |
| PE20050344A1 (es) | 2005-06-19 |
| TW200517378A (en) | 2005-06-01 |
| US20050043537A1 (en) | 2005-02-24 |
| US20080033175A1 (en) | 2008-02-07 |
| WO2005019201A2 (en) | 2005-03-03 |
| US7297795B2 (en) | 2007-11-20 |
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