KR20110120878A - 치환된 퀴나졸린 화합물 - Google Patents
치환된 퀴나졸린 화합물 Download PDFInfo
- Publication number
- KR20110120878A KR20110120878A KR1020117017495A KR20117017495A KR20110120878A KR 20110120878 A KR20110120878 A KR 20110120878A KR 1020117017495 A KR1020117017495 A KR 1020117017495A KR 20117017495 A KR20117017495 A KR 20117017495A KR 20110120878 A KR20110120878 A KR 20110120878A
- Authority
- KR
- South Korea
- Prior art keywords
- phenyl
- quinazolin
- ylamino
- chloro
- compound
- 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- Withdrawn
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- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical class N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 143
- 238000000034 method Methods 0.000 claims abstract description 64
- -1 2-Chloro-5-hydroxy-phenyl Chemical group 0.000 claims description 20
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 239000012453 solvate Substances 0.000 claims description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 150000004677 hydrates Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- UWWLIQXOZPIZNJ-HHHXNRCGSA-N (2r)-1-[2-[3-[4-[[6-(2-chloro-5-hydroxyphenyl)-8-methylquinazolin-2-yl]amino]phenyl]-2-oxoimidazolidin-1-yl]ethyl]pyrrolidine-2-carboxylic acid Chemical compound N1=C2C(C)=CC(C=3C(=CC=C(O)C=3)Cl)=CC2=CN=C1NC(C=C1)=CC=C1N(C1=O)CCN1CCN1CCC[C@@H]1C(O)=O UWWLIQXOZPIZNJ-HHHXNRCGSA-N 0.000 claims description 2
- SIACCBGVOWSQAC-AREMUKBSSA-N (2r)-1-[2-[4-[[6-(2,6-dimethylphenyl)quinazolin-2-yl]amino]phenoxy]ethyl]pyrrolidine-2-carboxylic acid Chemical compound CC1=CC=CC(C)=C1C1=CC=C(N=C(NC=2C=CC(OCCN3[C@H](CCC3)C(O)=O)=CC=2)N=C2)C2=C1 SIACCBGVOWSQAC-AREMUKBSSA-N 0.000 claims description 2
- VTCLJEBTUYBWMX-RUZDIDTESA-N (2r)-1-[2-[4-[[6-(2-chloro-5-hydroxyphenyl)-8-methylquinazolin-2-yl]amino]phenoxy]ethyl]pyrrolidine-2-carboxylic acid Chemical compound N1=C2C(C)=CC(C=3C(=CC=C(O)C=3)Cl)=CC2=CN=C1NC(C=C1)=CC=C1OCCN1CCC[C@@H]1C(O)=O VTCLJEBTUYBWMX-RUZDIDTESA-N 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- MHCMBFVCAZAHNM-RUZDIDTESA-N 1-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]-2-[4-[[6-(2,6-dimethylphenyl)quinazolin-2-yl]amino]phenoxy]ethanone Chemical compound C1[C@H](N(C)C)CCN1C(=O)COC(C=C1)=CC=C1NC1=NC=C(C=C(C=C2)C=3C(=CC=CC=3C)C)C2=N1 MHCMBFVCAZAHNM-RUZDIDTESA-N 0.000 claims description 2
- DCUDFYSDQVJVAX-UHFFFAOYSA-N 1-[4-[4-[[6-(2,6-dimethylphenyl)quinazolin-2-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=C(C=C2)C=3C(=CC=CC=3C)C)C2=N1 DCUDFYSDQVJVAX-UHFFFAOYSA-N 0.000 claims description 2
- AMMREYAIIGJNRT-UHFFFAOYSA-N 1-[4-[4-[[6-(2-chloro-5-hydroxyphenyl)-8-methylquinazolin-2-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=C(C=C2C)C=3C(=CC=C(O)C=3)Cl)C2=N1 AMMREYAIIGJNRT-UHFFFAOYSA-N 0.000 claims description 2
- TYRDPAITJGOXCX-UHFFFAOYSA-N 1-[4-[[6-(2,6-dimethylphenyl)quinazolin-2-yl]amino]phenyl]-3-(2-pyrrolidin-1-ylethyl)imidazolidin-2-one Chemical compound CC1=CC=CC(C)=C1C1=CC=C(N=C(NC=2C=CC(=CC=2)N2C(N(CCN3CCCC3)CC2)=O)N=C2)C2=C1 TYRDPAITJGOXCX-UHFFFAOYSA-N 0.000 claims description 2
- MCWXXILNYUKEIR-UHFFFAOYSA-N 1-[4-[[6-(2-chloro-5-hydroxyphenyl)-8-methylquinazolin-2-yl]amino]phenyl]-3-(2-pyrrolidin-1-ylethyl)imidazolidin-2-one Chemical compound N1=C2C(C)=CC(C=3C(=CC=C(O)C=3)Cl)=CC2=CN=C1NC(C=C1)=CC=C1N(C1=O)CCN1CCN1CCCC1 MCWXXILNYUKEIR-UHFFFAOYSA-N 0.000 claims description 2
- SDNJFGWENJJGAI-AREMUKBSSA-N 1-[4-[[6-(2-chloro-5-hydroxyphenyl)-8-methylquinazolin-2-yl]amino]phenyl]-3-[2-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]ethyl]imidazolidin-2-one Chemical compound C1[C@H](N(C)C)CCN1CCN1C(=O)N(C=2C=CC(NC=3N=C4C(C)=CC(=CC4=CN=3)C=3C(=CC=C(O)C=3)Cl)=CC=2)CC1 SDNJFGWENJJGAI-AREMUKBSSA-N 0.000 claims description 2
- DYMFCCVAGSKVST-UHFFFAOYSA-N 1-[4-[[6-(2-chloro-5-hydroxyphenyl)quinazolin-2-yl]amino]phenyl]-3-(2-methoxyethyl)imidazolidin-2-one Chemical compound O=C1N(CCOC)CCN1C(C=C1)=CC=C1NC1=NC=C(C=C(C=C2)C=3C(=CC=C(O)C=3)Cl)C2=N1 DYMFCCVAGSKVST-UHFFFAOYSA-N 0.000 claims description 2
- DKDSOJOOGBYVHM-JOCHJYFZSA-N 2-[4-[[6-(2-chloro-5-hydroxyphenyl)-8-methylquinazolin-2-yl]amino]phenoxy]-1-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]ethanone Chemical compound C1[C@H](N(C)C)CCN1C(=O)COC(C=C1)=CC=C1NC1=NC=C(C=C(C=C2C)C=3C(=CC=C(O)C=3)Cl)C2=N1 DKDSOJOOGBYVHM-JOCHJYFZSA-N 0.000 claims description 2
- BERSKKCARFLVRV-UHFFFAOYSA-N 3-[2-[4-[2-(azepan-1-yl)ethoxy]anilino]quinazolin-6-yl]-4-chlorophenol Chemical compound OC1=CC=C(Cl)C(C=2C=C3C=NC(NC=4C=CC(OCCN5CCCCCC5)=CC=4)=NC3=CC=2)=C1 BERSKKCARFLVRV-UHFFFAOYSA-N 0.000 claims description 2
- SUSIZIGAKZXBKA-UHFFFAOYSA-N 4-chloro-3-[2-[3-(hydroxymethyl)anilino]-8-methylquinazolin-6-yl]phenol Chemical compound N1=C2C(C)=CC(C=3C(=CC=C(O)C=3)Cl)=CC2=CN=C1NC1=CC=CC(CO)=C1 SUSIZIGAKZXBKA-UHFFFAOYSA-N 0.000 claims description 2
- LPMCVZGZXTUCIL-UHFFFAOYSA-N 4-chloro-3-[2-[4-(2-pyrrolidin-1-ylethoxy)anilino]quinazolin-6-yl]phenol Chemical compound OC1=CC=C(Cl)C(C=2C=C3C=NC(NC=4C=CC(OCCN5CCCC5)=CC=4)=NC3=CC=2)=C1 LPMCVZGZXTUCIL-UHFFFAOYSA-N 0.000 claims description 2
- VGTYSWHJDXCEDB-UHFFFAOYSA-N 4-chloro-3-[8-methyl-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]quinazolin-6-yl]phenol Chemical compound N1=C2C(C)=CC(C=3C(=CC=C(O)C=3)Cl)=CC2=CN=C1NC(C=C1)=CC=C1OCCN1CCCC1 VGTYSWHJDXCEDB-UHFFFAOYSA-N 0.000 claims description 2
- XNURRHDXCWKBOG-UHFFFAOYSA-N 6-(2,6-dimethylphenyl)-n-(4-piperazin-1-ylphenyl)quinazolin-2-amine Chemical compound CC1=CC=CC(C)=C1C1=CC=C(N=C(NC=2C=CC(=CC=2)N2CCNCC2)N=C2)C2=C1 XNURRHDXCWKBOG-UHFFFAOYSA-N 0.000 claims description 2
- XMEMWQHGCLIHOM-UHFFFAOYSA-N 6-(2,6-dimethylphenyl)-n-[4-(2-pyrrolidin-1-ylethoxy)phenyl]quinazolin-2-amine Chemical compound CC1=CC=CC(C)=C1C1=CC=C(N=C(NC=2C=CC(OCCN3CCCC3)=CC=2)N=C2)C2=C1 XMEMWQHGCLIHOM-UHFFFAOYSA-N 0.000 claims description 2
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- DPMRCMKQVYZSIO-UHFFFAOYSA-N [4-[4-[[6-(2,6-dimethylphenyl)quinazolin-2-yl]amino]phenyl]piperazin-1-yl]-pyridin-4-ylmethanone Chemical compound CC1=CC=CC(C)=C1C1=CC=C(N=C(NC=2C=CC(=CC=2)N2CCN(CC2)C(=O)C=2C=CN=CC=2)N=C2)C2=C1 DPMRCMKQVYZSIO-UHFFFAOYSA-N 0.000 claims description 2
- MPNPFEPBTPBOAQ-UHFFFAOYSA-N [4-[4-[[6-(2-chloro-5-hydroxyphenyl)-8-methylquinazolin-2-yl]amino]phenyl]piperazin-1-yl]-pyridin-2-ylmethanone Chemical compound N1=C2C(C)=CC(C=3C(=CC=C(O)C=3)Cl)=CC2=CN=C1NC(C=C1)=CC=C1N(CC1)CCN1C(=O)C1=CC=CC=N1 MPNPFEPBTPBOAQ-UHFFFAOYSA-N 0.000 claims description 2
- UKZPNRGUTKWSFX-UHFFFAOYSA-N [4-[4-[[6-(2-chloro-5-hydroxyphenyl)-8-methylquinazolin-2-yl]amino]phenyl]piperazin-1-yl]-pyridin-3-ylmethanone Chemical compound N1=C2C(C)=CC(C=3C(=CC=C(O)C=3)Cl)=CC2=CN=C1NC(C=C1)=CC=C1N(CC1)CCN1C(=O)C1=CC=CN=C1 UKZPNRGUTKWSFX-UHFFFAOYSA-N 0.000 claims description 2
- MBVYOVSHWHBDPI-UHFFFAOYSA-N [4-[4-[[6-(2-chloro-5-hydroxyphenyl)-8-methylquinazolin-2-yl]amino]phenyl]piperazin-1-yl]-pyridin-4-ylmethanone Chemical compound N1=C2C(C)=CC(C=3C(=CC=C(O)C=3)Cl)=CC2=CN=C1NC(C=C1)=CC=C1N(CC1)CCN1C(=O)C1=CC=NC=C1 MBVYOVSHWHBDPI-UHFFFAOYSA-N 0.000 claims description 2
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Emergency Medicine (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Ophthalmology & Optometry (AREA)
- Epidemiology (AREA)
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- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08360043.7 | 2008-12-29 | ||
| EP08360043 | 2008-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20110120878A true KR20110120878A (ko) | 2011-11-04 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020117017495A Withdrawn KR20110120878A (ko) | 2008-12-29 | 2009-12-18 | 치환된 퀴나졸린 화합물 |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US8389530B2 (https=) |
| EP (1) | EP2381943A1 (https=) |
| JP (1) | JP2012514020A (https=) |
| KR (1) | KR20110120878A (https=) |
| CN (1) | CN102333533A (https=) |
| AU (1) | AU2009334869A1 (https=) |
| BR (1) | BRPI0924067A2 (https=) |
| CA (1) | CA2748319A1 (https=) |
| CO (1) | CO6390105A2 (https=) |
| CR (1) | CR20110368A (https=) |
| DO (1) | DOP2011000209A (https=) |
| EA (1) | EA019110B1 (https=) |
| EC (1) | ECSP11011204A (https=) |
| IL (1) | IL213742A0 (https=) |
| MA (1) | MA32968B1 (https=) |
| MX (1) | MX2011007064A (https=) |
| NI (1) | NI201100134A (https=) |
| NZ (1) | NZ593949A (https=) |
| PE (1) | PE20120424A1 (https=) |
| SG (1) | SG172415A1 (https=) |
| TN (1) | TN2011000319A1 (https=) |
| WO (1) | WO2010076238A1 (https=) |
| ZA (1) | ZA201104777B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160009750A (ko) * | 2014-07-16 | 2016-01-27 | 주식회사 큐리언트 | 염증성 질환 치료용 화합물 |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR081960A1 (es) | 2010-06-22 | 2012-10-31 | Fovea Pharmaceuticals Sa | Compuestos heterociclicos, su preparacion y su aplicacion terapeutica |
| SMT202100451T1 (it) | 2012-07-11 | 2021-09-14 | Blueprint Medicines Corp | Inibitori del recettore di crescita dei fibroblasti |
| CA2928042C (en) | 2013-10-25 | 2022-05-10 | Blueprint Medicines Corporation | Inhibitors of the fibroblast growth factor receptor |
| WO2015108992A1 (en) | 2014-01-15 | 2015-07-23 | Blueprint Medicines Corporation | Heterobicyclic compounds and their use as fgfr4 receptor inhibitors |
| TWI699355B (zh) | 2014-12-24 | 2020-07-21 | 美商基利科學股份有限公司 | 喹唑啉化合物 |
| BR112017013440A2 (pt) | 2014-12-24 | 2018-01-09 | Gilead Sciences, Inc. | compostos de isoquinolina para o tratamento de hiv |
| ES2735087T3 (es) | 2014-12-24 | 2019-12-16 | Gilead Sciences Inc | Compuestos de pirimidina fusionados para el tratamiento de VIH |
| CN112239459B (zh) * | 2019-07-19 | 2021-11-26 | 中国科学院上海药物研究所 | 稠环嘧啶氨基化合物、其制备方法、药物组合物及应用 |
| CN115916759B (zh) * | 2020-06-19 | 2025-07-15 | 泰州红云制药有限公司 | 取代喹唑啉类化合物、其制备方法、药物组合及应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2386955A1 (en) * | 1999-11-22 | 2001-05-31 | Warner-Lambert Company | Quinazolines and their use for inhibiting cyclin-dependent kinase enzymes |
| EP1590341B1 (en) | 2003-01-17 | 2009-06-17 | Warner-Lambert Company LLC | 2-aminopyridine substituted heterocycles as inhibitors of cellular proliferation |
| CN1882345A (zh) | 2003-10-16 | 2006-12-20 | 希龙公司 | 作为raf激酶抑制剂以治疗癌症的2,6－二取代的喹唑啉、喹喔啉、喹啉和异喹啉 |
| KR20070011458A (ko) | 2004-04-08 | 2007-01-24 | 탈자진 인코포레이티드 | 키나제의 벤조트리아진 억제제 |
| PL382308A1 (pl) | 2004-08-25 | 2007-08-20 | Targegen, Inc. | Związki heterocykliczne i sposoby stosowania |
| US20070054916A1 (en) | 2004-10-01 | 2007-03-08 | Amgen Inc. | Aryl nitrogen-containing bicyclic compounds and methods of use |
| US20060247250A1 (en) | 2005-03-16 | 2006-11-02 | Targegen, Inc. | Pyrimidine inhibitors of kinases |
| JP5079500B2 (ja) * | 2005-04-28 | 2012-11-21 | 協和発酵キリン株式会社 | ２−アミノキナゾリン誘導体 |
| NZ563984A (en) | 2005-06-08 | 2011-11-25 | Targegen Inc | Methods and compositions for the treatment of ocular disorders |
| TW200808739A (en) * | 2006-04-06 | 2008-02-16 | Novartis Vaccines & Diagnostic | Quinazolines for PDK1 inhibition |
| CA2673003A1 (en) * | 2006-12-22 | 2008-07-03 | Novartis Ag | Quinazolines for pdk1 inhibition |
-
2009
- 2009-12-18 AU AU2009334869A patent/AU2009334869A1/en not_active Abandoned
- 2009-12-18 CN CN2009801575427A patent/CN102333533A/zh active Pending
- 2009-12-18 CA CA2748319A patent/CA2748319A1/en not_active Abandoned
- 2009-12-18 EA EA201101012A patent/EA019110B1/ru not_active IP Right Cessation
- 2009-12-18 PE PE2011001296A patent/PE20120424A1/es not_active Application Discontinuation
- 2009-12-18 WO PCT/EP2009/067494 patent/WO2010076238A1/en not_active Ceased
- 2009-12-18 JP JP2011544017A patent/JP2012514020A/ja active Pending
- 2009-12-18 EP EP09799340A patent/EP2381943A1/en not_active Withdrawn
- 2009-12-18 SG SG2011047339A patent/SG172415A1/en unknown
- 2009-12-18 BR BRPI0924067A patent/BRPI0924067A2/pt not_active IP Right Cessation
- 2009-12-18 MA MA34018A patent/MA32968B1/fr unknown
- 2009-12-18 NZ NZ593949A patent/NZ593949A/xx not_active IP Right Cessation
- 2009-12-18 MX MX2011007064A patent/MX2011007064A/es active IP Right Grant
- 2009-12-18 KR KR1020117017495A patent/KR20110120878A/ko not_active Withdrawn
- 2009-12-18 US US13/142,333 patent/US8389530B2/en not_active Expired - Fee Related
-
2011
- 2011-06-23 IL IL213742A patent/IL213742A0/en unknown
- 2011-06-27 TN TN2011000319A patent/TN2011000319A1/fr unknown
- 2011-06-27 CR CR20110368A patent/CR20110368A/es not_active Application Discontinuation
- 2011-06-28 ZA ZA2011/04777A patent/ZA201104777B/en unknown
- 2011-06-29 DO DO2011000209A patent/DOP2011000209A/es unknown
- 2011-06-29 NI NI201100134A patent/NI201100134A/es unknown
- 2011-06-29 CO CO11081323A patent/CO6390105A2/es not_active Application Discontinuation
- 2011-07-14 EC EC2011011204A patent/ECSP11011204A/es unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160009750A (ko) * | 2014-07-16 | 2016-01-27 | 주식회사 큐리언트 | 염증성 질환 치료용 화합물 |
Also Published As
| Publication number | Publication date |
|---|---|
| NZ593949A (en) | 2013-08-30 |
| TN2011000319A1 (en) | 2012-12-17 |
| ZA201104777B (en) | 2012-03-28 |
| US20120004210A1 (en) | 2012-01-05 |
| BRPI0924067A2 (pt) | 2016-01-26 |
| CA2748319A1 (en) | 2010-07-08 |
| AU2009334869A2 (en) | 2011-09-29 |
| IL213742A0 (en) | 2011-07-31 |
| SG172415A1 (en) | 2011-07-28 |
| EA019110B1 (ru) | 2014-01-30 |
| CO6390105A2 (es) | 2012-02-29 |
| WO2010076238A1 (en) | 2010-07-08 |
| JP2012514020A (ja) | 2012-06-21 |
| MX2011007064A (es) | 2012-01-20 |
| CR20110368A (es) | 2011-12-02 |
| AU2009334869A1 (en) | 2011-07-14 |
| PE20120424A1 (es) | 2012-05-04 |
| ECSP11011204A (es) | 2011-10-31 |
| EA201101012A1 (ru) | 2012-01-30 |
| US8389530B2 (en) | 2013-03-05 |
| MA32968B1 (fr) | 2012-01-02 |
| DOP2011000209A (es) | 2011-09-30 |
| CN102333533A (zh) | 2012-01-25 |
| NI201100134A (es) | 2012-03-06 |
| EP2381943A1 (en) | 2011-11-02 |
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Legal Events
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| PA0105 | International application |
Patent event date: 20110725 Patent event code: PA01051R01D Comment text: International Patent Application |
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| 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 |