IL187812A - Imidazo-and triazolopyridines as inhibitors of 11-beta hydroxysteroid dehydrogenase type 1 - Google Patents
Imidazo-and triazolopyridines as inhibitors of 11-beta hydroxysteroid dehydrogenase type 1Info
- Publication number
- IL187812A IL187812A IL187812A IL18781207A IL187812A IL 187812 A IL187812 A IL 187812A IL 187812 A IL187812 A IL 187812A IL 18781207 A IL18781207 A IL 18781207A IL 187812 A IL187812 A IL 187812A
- Authority
- IL
- Israel
- Prior art keywords
- aryl
- heteroaryl
- alkyl
- heterocyclyl
- optionally substituted
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title claims description 42
- 150000008523 triazolopyridines Chemical class 0.000 title description 3
- 102000008645 11-beta-Hydroxysteroid Dehydrogenase Type 1 Human genes 0.000 title 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
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- LMJSLTNSBFUCMU-UHFFFAOYSA-N trichlormethiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC(C(Cl)Cl)NS2(=O)=O LMJSLTNSBFUCMU-UHFFFAOYSA-N 0.000 description 1
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- 229960001641 troglitazone Drugs 0.000 description 1
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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- Pyridine Compounds (AREA)
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| US11/448,947 US7579360B2 (en) | 2005-06-09 | 2006-06-07 | Triazolopyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| PCT/US2006/022576 WO2006135795A1 (en) | 2005-06-09 | 2006-06-08 | Imidazo- and triazolopyridines as inhibitors of 11-beta hydroxysteroid dehydrogenase type i |
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| IL187812A0 IL187812A0 (en) | 2008-08-07 |
| IL187812A true IL187812A (en) | 2012-02-29 |
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| AR059898A1 (es) | 2006-03-15 | 2008-05-07 | Janssen Pharmaceutica Nv | Derivados de 3-ciano-piridona 1,4-disustituida y su uso como moduladores alostericos de los receptores mglur2 |
| PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
| AU2007283113A1 (en) | 2006-08-08 | 2008-02-14 | Sanofi-Aventis | Arylaminoaryl-alkyl-substituted imidazolidine-2,4-diones, processes for preparing them, medicaments comprising these compounds, and their use |
| TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
| TW200845978A (en) | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US8722894B2 (en) | 2007-09-14 | 2014-05-13 | Janssen Pharmaceuticals, Inc. | 1,3-disubstituted-4-phenyl-1H-pyridin-2-ones |
| MX2010002536A (es) | 2007-09-14 | 2010-08-10 | Ortho Mcneil Janssen Pharm | 4-fenil-3,4,5,6-tetrahidro-2h, 1'h-[1,4]bipiridinil-2'-onas 1',3'-disubstituidas. |
| CA2697399C (en) | 2007-09-14 | 2016-01-19 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | 1,3-disubstituted 4-(aryl-x-phenyl)-1h-pyridin-2-ones |
| US8119658B2 (en) * | 2007-10-01 | 2012-02-21 | Bristol-Myers Squibb Company | Triazolopyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| MX2010005110A (es) | 2007-11-14 | 2010-09-09 | Ortho Mcneil Janssen Pharm | Derivados de imidazo[1,2-a]piridina y su uso como moduladores alostericos positivos de los receptores de glutamato metabotropico 2. |
| US8470841B2 (en) | 2008-07-09 | 2013-06-25 | Sanofi | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
| BRPI0918055A2 (pt) | 2008-09-02 | 2015-12-01 | Addex Pharmaceuticals Sa | derivados de 3-azabiciclo[3,1,0]hexila como moduladores de receptores metabotrópicos de glutamato. |
| JP5656848B2 (ja) | 2008-10-16 | 2015-01-21 | ジャンセン ファーマシューティカルズ， インコーポレイテッド． | 代謝型グルタミン酸受容体モジュレーターとしてのインドールおよびベンゾモルホリンの誘導体 |
| CA2744138C (en) | 2008-11-28 | 2015-08-11 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | Indole and benzoxazine derivatives as modulators of metabotropic glutamate receptors |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| US8685967B2 (en) | 2009-04-07 | 2014-04-01 | Merck Sharp & Dohme Corp. | Substituted triazolopyridines and analogs thereof |
| ES2409006T3 (es) | 2009-05-12 | 2013-06-24 | Janssen Pharmaceuticals Inc. | Derivados de 1,2,4-triazolo[4,3-a]piridina y su uso como moduladores alostéricos positivos de los receptores mGluR2 |
| MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| SG176021A1 (en) | 2009-05-12 | 2011-12-29 | Janssen Pharmaceuticals Inc | 1,2,4-triazolo [4,3-a] pyridine derivatives and their use for the treatment or prevention of neurological and psychiatric disorders |
| ES2350077B1 (es) | 2009-06-04 | 2011-11-04 | Laboratorios Salvat, S.A. | Compuestos inhibidores de 11beta-hidroxiesteroide deshidrogenasa de tipo 1. |
| JP2013503135A (ja) | 2009-08-26 | 2013-01-31 | サノフイ | 新規な結晶性複素芳香族フルオログリコシド水和物、その化合物を含んでなる医薬及びその使用 |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| US9012448B2 (en) | 2010-11-08 | 2015-04-21 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of MGLUR2 receptors |
| WO2012062759A1 (en) | 2010-11-08 | 2012-05-18 | Janssen Pharmaceuticals, Inc. | 1,2,4-TRIAZOLO[4,3-a]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS |
| PL2649069T3 (pl) | 2010-11-08 | 2016-01-29 | Janssen Pharmaceuticals Inc | Pochodne 1,2,4-triazolo[4,3-a]pirydyny i ich zastosowanie jako dodatnich allosterycznych modulatorów receptorów mGluR2 |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120054A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
| JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
| WO2015061272A1 (en) | 2013-10-22 | 2015-04-30 | Bristol-Myers Squibb Company | Isotopically labeled triazolopyridine 11-beta hydroxysteroid dehydrogenase type i inhibitors |
| GB201321742D0 (en) * | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
| EP3087069B1 (en) | 2013-12-23 | 2019-01-30 | Norgine B.V. | Compounds useful as ccr9 modulators |
| PT3096790T (pt) | 2014-01-21 | 2019-10-15 | Janssen Pharmaceutica Nv | Combinações compreendendo moduladores alostéricos positivos ou agonistas ortostéricos do recetor glutamatérgico metabotrópico do subtipo 2 e seu uso |
| EA202192105A3 (ru) | 2014-02-04 | 2022-02-28 | Янссен Фармацевтика Нв | Комбинации, содержащие положительные аллостерические модуляторы или ортостерические агонисты метаботропного глутаматергического рецептора 2 подтипа, и их применение |
| WO2015123408A1 (en) | 2014-02-13 | 2015-08-20 | Incyte Corporation | Cyclopropylamines as lsd1 inhibitors |
| WO2015123437A1 (en) | 2014-02-13 | 2015-08-20 | Incyte Corporation | Cyclopropylamines as lsd1 inhibitors |
| PE20161573A1 (es) | 2014-02-13 | 2017-01-19 | Incyte Corp | Ciclopropilamina como inhibidor de la lsd1 |
| TWI664164B (zh) | 2014-02-13 | 2019-07-01 | 美商英塞特控股公司 | 作為ｌｓｄ１抑制劑之環丙胺 |
| US9758523B2 (en) | 2014-07-10 | 2017-09-12 | Incyte Corporation | Triazolopyridines and triazolopyrazines as LSD1 inhibitors |
| US9695180B2 (en) | 2014-07-10 | 2017-07-04 | Incyte Corporation | Substituted imidazo[1,2-a]pyrazines as LSD1 inhibitors |
| US9695168B2 (en) | 2014-07-10 | 2017-07-04 | Incyte Corporation | Substituted imidazo[1,5-α]pyridines and imidazo[1,5-α]pyrazines as LSD1 inhibitors |
| WO2016007722A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| US9580420B2 (en) | 2014-08-06 | 2017-02-28 | Bristol-Meyers Squibb Company | Process for the preparation of 4-(8-(2-chlorophenoxy)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)bicyclo[2.2.1]heptan-1-ol and novel intermediates therefor |
| MY191796A (en) | 2015-04-03 | 2022-07-15 | Incyte Corp | Heterocyclic compounds as lsd1 inhibitors |
| KR102710120B1 (ko) | 2015-08-12 | 2024-09-27 | 인사이트 홀딩스 코포레이션 | Lsd1 저해제의 염 |
| PE20190377A1 (es) | 2016-04-22 | 2019-03-08 | Incyte Corp | Formulaciones de un inhibidor de lsd 1 |
| US10689378B2 (en) * | 2016-06-20 | 2020-06-23 | Novartis Ag | Triazolopyridine compounds and uses thereof |
| US10968200B2 (en) | 2018-08-31 | 2021-04-06 | Incyte Corporation | Salts of an LSD1 inhibitor and processes for preparing the same |
Family Cites Families (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3597423A (en) * | 1966-08-31 | 1971-08-03 | Boehringer Mannheim Gmbh | 5-nitrofuryl-2-s-triazolo-(4,3-a)-pyridine derivatives |
| US4358453A (en) * | 1982-01-08 | 1982-11-09 | Schering Corporation | 1,2,4-Triazolo[4,3-a]pyridines |
| US5236917A (en) * | 1989-05-04 | 1993-08-17 | Sterling Winthrop Inc. | Saccharin derivatives useful as proteolytic enzyme inhibitors and compositions and method of use thereof |
| IL96432A0 (en) | 1989-11-30 | 1991-08-16 | Schering Ag | Pesticidal compositions containing pyridine derivatives and novel pyridine derivatives |
| WO1997047601A1 (en) | 1996-06-11 | 1997-12-18 | Yoshitomi Pharmaceutical Industries, Ltd. | Fused heterocyclic compounds and medicinal uses thereof |
| BR0010139A (pt) | 1999-04-28 | 2004-03-02 | Reddy Research Foundation | Heterociclos bicìclicos substituìdos, processo para seu preparo e seu uso como agentes anti-obesidade e hipocolesterolêmico |
| JP2000319277A (ja) | 1999-05-11 | 2000-11-21 | Ono Pharmaceut Co Ltd | 縮合ピラジン化合物およびその化合物を有効成分とする薬剤 |
| JP4747396B2 (ja) | 2000-05-17 | 2011-08-17 | 日立化成工業株式会社 | 接着剤組成物、それを用いた回路端子の接続方法及び回路端子の接続構造 |
| CN1496366A (zh) * | 2001-03-09 | 2004-05-12 | �Ʒ� | 作为抗炎剂的三唑并吡啶 |
| US20050113283A1 (en) * | 2002-01-18 | 2005-05-26 | David Solow-Cordero | Methods of treating conditions associated with an EDG-4 receptor |
| EP1474139B1 (en) | 2002-02-01 | 2007-11-21 | Merck & Co., Inc. | 11-beta-hydroxysteroid dehydrogenase 1 inhibitors useful for the treatment of diabetes, obesity and dyslipidemia |
| AR040241A1 (es) | 2002-06-10 | 2005-03-23 | Merck & Co Inc | Inhibidores de la 11-beta-hidroxiesteroide deshidrogrenasa 1 para el tratamiento de la diabetes obesidad y dislipidemia |
| BR0313961A (pt) * | 2002-08-30 | 2005-07-19 | Pfizer Prod Inc | Processos e intermediários para preparar triazolo-piridinas |
| MY139563A (en) * | 2002-09-04 | 2009-10-30 | Bristol Myers Squibb Co | Heterocyclic aromatic compounds useful as growth hormone secretagogues |
| JO2397B1 (en) | 2002-12-20 | 2007-06-17 | ميرك شارب اند دوم كوربوريشن | Terazol derivatives as beta-hydroxy steroid dihydrogenase-1 inhibitors |
| WO2004056744A1 (en) | 2002-12-23 | 2004-07-08 | Janssen Pharmaceutica N.V. | Adamantyl acetamides as hydroxysteroid dehydrogenase inhibitors |
| TW200503994A (en) | 2003-01-24 | 2005-02-01 | Novartis Ag | Organic compounds |
| ATE334131T1 (de) * | 2003-02-14 | 2006-08-15 | Pfizer Prod Inc | Triazolopyridine als entzündungshemmende verbindungen |
| ATE455547T1 (de) | 2003-04-11 | 2010-02-15 | High Point Pharmaceuticals Llc | Pharmazeutische verwendungen von kondensierten 1, 2,4-triazolen |
| EP1619948A4 (en) * | 2003-05-05 | 2007-02-14 | Neurogen Corp | SUBSTITUTED IMIDAZOLOPYRAZINE AND TRIAZOLOPYRAZINE DERIVATIVES: GABAA RECEPTOR LIGANDS |
| WO2004106294A2 (en) | 2003-05-29 | 2004-12-09 | Merck & Co., Inc. | Triazole derivatives as inhibitors of 11-beta hydroxysteroid dehydrogenase-1 |
| US20050049276A1 (en) * | 2003-07-23 | 2005-03-03 | Warner-Lambert Company, Llc | Imidazopyridines and triazolopyridines |
| US7144907B2 (en) * | 2003-09-03 | 2006-12-05 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
| US7538120B2 (en) * | 2003-09-03 | 2009-05-26 | Array Biopharma Inc. | Method of treating inflammatory diseases |
| GB0325745D0 (en) | 2003-11-05 | 2003-12-10 | Astrazeneca Ab | Chemical compounds |
| GB0326029D0 (en) | 2003-11-07 | 2003-12-10 | Astrazeneca Ab | Chemical compounds |
| IN2012DN03023A (enExample) | 2004-01-26 | 2015-07-31 | Merck Sharp & Dohme | |
| US7306631B2 (en) * | 2004-03-30 | 2007-12-11 | The Procter & Gamble Company | Keratin dyeing compounds, keratin dyeing compositions containing them, and use thereof |
| EP1778685B1 (de) | 2004-08-02 | 2008-03-26 | Schwarz Pharma Ag | Carboxamide des indolizins und seiner aza- und diazaderivate |
| WO2006018718A2 (en) * | 2004-08-12 | 2006-02-23 | Pfizer Limited | Triazolopyridinylsulfanyl derivatives as p38 map kinase inhibitors |
| BRPI0514391A (pt) | 2004-08-18 | 2008-06-10 | Pharmacia & Upjohn Co Llc | compostos de triazolopiridina para o tratamento de inflamação |
| BRPI0514327A (pt) | 2004-08-18 | 2008-06-10 | Pharmacia & Upjohn Co Llc | compostos triazolopiridina |
| US7605168B2 (en) | 2004-09-03 | 2009-10-20 | Plexxikon, Inc. | PDE4B inhibitors |
| WO2006030805A1 (ja) | 2004-09-16 | 2006-03-23 | Astellas Pharma Inc. | トリアゾール誘導体またはその塩 |
| US20080171740A1 (en) | 2004-09-24 | 2008-07-17 | Smithkline Beecham Corporation | Chemical Compounds |
| CN101039942A (zh) | 2004-09-27 | 2007-09-19 | 伊利舍医药品公司 | 磺酰胺类及其用途 |
| BRPI0515931A (pt) | 2004-09-29 | 2008-08-12 | Hoffmann La Roche | compostos, processo para a sua preparação, composições farmacêuticas que os compreendem, método para o tratamento e/ou profilaxia de enfermidades e utilização desses compostos |
| JP2008515874A (ja) | 2004-10-07 | 2008-05-15 | ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー | 抗菌薬 |
| WO2006038738A1 (ja) | 2004-10-08 | 2006-04-13 | Takeda Pharmaceutical Company Limited | 受容体機能調節剤 |
| ATE512146T1 (de) | 2004-10-13 | 2011-06-15 | Merck Patent Gmbh | Phenylharnstoffderivate als hemmstoffe von tyrosinkinasen zur behandlung von tumorerkrankungen |
| WO2006040039A1 (de) | 2004-10-13 | 2006-04-20 | Merck Patent Gmbh | Als kinaseinhibitoren geeignete derivate des n, n ´ -diphenylharnstoffs |
| ATE479687T1 (de) | 2004-10-15 | 2010-09-15 | Takeda Pharmaceutical | Kinaseinhibitoren |
| US7652035B2 (en) | 2004-10-19 | 2010-01-26 | Neurocrine Bioscience, Inc. | CRF receptor antagonists and methods relating thereto |
| GB0519957D0 (en) | 2005-09-30 | 2005-11-09 | Sb Pharmco Inc | Chemical compound |
| US7151176B2 (en) | 2004-10-21 | 2006-12-19 | Bristol-Myers Squibb Company | Pyrrolotriazine compounds |
| WO2006047631A2 (en) | 2004-10-25 | 2006-05-04 | University Of Medicine And Dentistry Of New Jersey | Anti-mitotic anti-proliferative compounds |
| EP1807072B1 (en) | 2004-10-29 | 2009-01-07 | Eli Lilly And Company | Cycloalkyl lactam derivatives as inhibitors of 11-beta-hydroxysteroid dehydrogenase 1 |
| EP1655283A1 (en) | 2004-11-08 | 2006-05-10 | Evotec OAI AG | 11beta-HSD1 Inhibitors |
| EP1666467A1 (en) | 2004-11-08 | 2006-06-07 | Evotec AG | 11Beta-HSD1 Inhibitors |
| AU2005311451A1 (en) | 2004-12-01 | 2006-06-08 | Merck Serono Sa | [1,2,4]triazolo[4,3-a]pyridine derivatives for the treatment of hyperproliferative diseases |
| JPWO2006080533A1 (ja) | 2005-01-31 | 2008-06-19 | 持田製薬株式会社 | ３−アミノ−１，２，４−トリアゾール誘導体 |
| WO2007007688A1 (ja) | 2005-07-08 | 2007-01-18 | Mochida Pharmaceutical Co., Ltd. | ３,５－ジアミノ－１,２,４－トリアゾール誘導体 |
| AU2007233709A1 (en) | 2006-03-31 | 2007-10-11 | Novartis Ag | Organic compounds |
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