AR069652A1 - Derivados de bencimidazol antagonistas de la ruta de hedgehog, composiciones farmaceuticas que los contienen y usos de los mismos para prevenir y/o tratar osteoporosis o cancer. - Google Patents
Derivados de bencimidazol antagonistas de la ruta de hedgehog, composiciones farmaceuticas que los contienen y usos de los mismos para prevenir y/o tratar osteoporosis o cancer.Info
- Publication number
- AR069652A1 AR069652A1 ARP080105382A ARP080105382A AR069652A1 AR 069652 A1 AR069652 A1 AR 069652A1 AR P080105382 A ARP080105382 A AR P080105382A AR P080105382 A ARP080105382 A AR P080105382A AR 069652 A1 AR069652 A1 AR 069652A1
- Authority
- AR
- Argentina
- Prior art keywords
- branched
- linear
- group
- cyclic
- alkyl
- Prior art date
Links
- 241000027355 Ferocactus setispinus Species 0.000 title 1
- 206010028980 Neoplasm Diseases 0.000 title 1
- 208000001132 Osteoporosis Diseases 0.000 title 1
- 239000005557 antagonist Substances 0.000 title 1
- 201000011510 cancer Diseases 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- -1 oxaalkyl Chemical group 0.000 abstract 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 6
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 abstract 5
- 125000004122 cyclic group Chemical group 0.000 abstract 5
- 125000001153 fluoro group Chemical group F* 0.000 abstract 5
- 229910052736 halogen Inorganic materials 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 125000005090 alkenylcarbonyl group Chemical group 0.000 abstract 3
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 abstract 3
- 125000003282 alkyl amino group Chemical group 0.000 abstract 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 abstract 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000005089 alkenylaminocarbonyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 125000004982 dihaloalkyl group Chemical group 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 abstract 1
- MTCZGPPSHVGCKQ-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1C1=CC=C(C=2NC3=CC=CC=C3N=2)C=C1 MTCZGPPSHVGCKQ-UHFFFAOYSA-N 0.000 abstract 1
- ODUDNWRZTRJXGE-UHFFFAOYSA-N 2-[4-(4-pyridin-2-ylpiperazin-1-yl)phenyl]-1h-benzimidazole Chemical compound C1CN(C=2C=CC(=CC=2)C=2NC3=CC=CC=C3N=2)CCN1C1=CC=CC=N1 ODUDNWRZTRJXGE-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000001118 alkylidene group Chemical group 0.000 abstract 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 230000007717 exclusion Effects 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 230000004927 fusion Effects 0.000 abstract 1
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 150000002466 imines Chemical class 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000003003 spiro group Chemical group 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 1
- 125000003396 thiol group Chemical class [H]S* 0.000 abstract 1
- 125000004951 trihalomethoxy group Chemical group 0.000 abstract 1
- 125000004953 trihalomethyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D403/12—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 chain containing hetero atoms as chain links
-
- 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
- C07D405/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Reivindicacion 1: Compuestos de formula (1) y sus sales aceptables para uso farmacéutico en donde, en tanto lo permitan la valencia y la estabilidad, R1 es H; un grupo alquilo C1-4 lineal, ramificado o cíclico, sustituido en forma opcional con uno o más halogeno, un grupo alcoxi C1-4 ramificado o lineal o un grupo mono- o di- alquilamino C1-6 lineal, ramificado o cíclico; r es igual a cero, 1, 2 o 3; R1' representan, de manera independiente uno del otro cuando r >1, halogeno; un grupo alcoxi C1-4 lineal, ramificado o cíclico; un grupo alquilo C1-4 lineal, ramificado o cíclico sustituido en forma opcional con un grupo alcoxi, alquilamino, o dialquilamino C1-4 lineal o ramificado; R2 puede ser H, CI, F o Br; X puede ser o N o CH; i y j pueden ser 1, 2 o 3, la suma i+j no puede exceder 5, y cuando X es N, entonces i y j no pueden ser 1; R3 puede ser H; un grupo alquilo, oxaalquilo, alquilcarbonilo, alquilsulfonilo, oxaalquilcarbonilo, alcoxicarbonilo, alquilaminocarbonilo, oxaalquenilo, alquenilcarbonilo, oxaalquenilcarbonilo, alqueniloxicarbonilo, alquenilaminocarbonilo, alquilideno, alquiloxiimino, hidroxi, alcoxi, alqueniloxi C1-6 lineal, ramificado o cíclico, sustituido en forma opcional con carbamoilo o uno o más átomos de fluor; Ar; Ar-aminocarbonilo; un grupo alquilo, alquilamino, azaalquilo, oxaalquilo, alquilcarbonilo, alcoxicarbonilo o alquilaminocarbonilo C1-4 lineal o ramificado, sustituido con uno o dos Ar y sustituido en forma opcional con uno o más átomos de fluor; o formulas (2); Q es tal que no se forma ningun enlace directo entre dos átomos de nitrogeno o entre un átomo de nitrogeno y un átomo de oxígeno y puede ser carbonilo; aminocarbonilo; carbonilamino, imina; SO2 alquilo C1-6 lineal o ramificado sustituido en forma opcional con uno o más átomos de fluor en donde un grupo metileno puede ser reemplazado por O, NRx, carbonilo o SO2 o en donde dos grupos metileno consecutivos pueden estar reemplazados con un grupo carbonilamino, aminocarbonilo, sulfonilamino, aminosulfonilo; Ar es un anillo aromático o heteroaromático de 5 a 10 miembros sustituido en forma opcional con uno o más grupos seleccionados independientemente entre halogeno, hidroxi, mercapto, amino, ciano, nitro, carbamoilo, sulfamoilo, trihalometilo, trihalometoxi, alquilo C1-4 lineal, ramificado o cíclico, hidroxialquilo, mono- o di-alquilamino, alcoxi, alquilcarbonilo, alcoxicarbonilo, alquilcarbonilamino, oxaalquilo, azaalquilo, y de tal modo que dos de estos sustituyentes pueden formar un anillo de 5 a 8 miembros con una union fusionada a Ar. Rx puede ser H o un alquilo, dihaloalquilo o triahaloalquilo C1-4 lineal, ramificado o cíclico; q puede ser cero o 1, k puede ser 1, 2, 3 o 4, l, m, n, p, p' y s pueden ser independientemente 1, 2, o 3; t puede ser cero, 1 o 2 las sumas l+m, n+p o p'+s+t no pueden exceder 5; T y T' representan, de manera independiente uno del otro, hidrogeno; una cadena alquilo, azaalquilo, oxaalquilo, alquenilo, azaalquenilo, oxaalquenilo C1-6 lineal, ramificada o cíclica, sustituida en forma opcional con halogeno, amino, ciano, hidroxi, oxo; alquilcarbonilo, alcoxicarbonilo, alquilcarbonilamino, alquilaminocarbonilo, carbamoilo, guanidino, alquenilcarbonilo, oxaalquenilcarbonilo, alqueniloxicarbonilo, alquenilaminocarbonilo C1-3 lineal, ramificado o cíclico, Z puede ser O, S, SO2, SO, o NRy'; Ry y Ry' representan de manera independiente H; un grupo alquilo, alquilcarbonilo, alcoxicarbonilo o alquilaminocarbonilo C1-6 lineal, ramificado o cíclico, sustituido en forma opcional con uno o más átomos de fluor y e y' pueden ser independientemente cero, 1, 2 o 3; Y1 e Y2 representan de manera independiente halogeno; hidroxi; amino; ciano; nitro; oxo; grupo alquilo, dihaloalquilo, azaalquilo, oxaalquilo, alquilcarbonilo, oxaalquilcarbonilo, alcoxicarbonilo, alquilaminocarbonilo, alquilcarbonilamino, alquenilo, oxaalquenilo, azaalquenilo, alquenilcarbonilo, oxaalquenilcarbonilo, alqueniloxicarbonilo, alquenilaminocarbonilo, alquilamino, mercaptoalquilo, alcoxi, alquiltio C1-6 lineal, o ramificado, sustituido en forma opcional con uno o más átomos de fluor; en donde dos grupos Y2 pueden formar un anillo de 5 a 8 miembros con union espiro o fusionada; y con la exclusion de 2-[4-(4-metil-piperazin-1-il)-fenil]-1H-benzoimidazol; 2-[4-(4-piridin-2-il-piperazin-1-il)-fenil]-1H-benzoimidazol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07024218 | 2007-12-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR069652A1 true AR069652A1 (es) | 2010-02-10 |
Family
ID=39432963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP080105382A AR069652A1 (es) | 2007-12-13 | 2008-12-11 | Derivados de bencimidazol antagonistas de la ruta de hedgehog, composiciones farmaceuticas que los contienen y usos de los mismos para prevenir y/o tratar osteoporosis o cancer. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8592463B2 (es) |
| EP (1) | EP2227456A2 (es) |
| JP (1) | JP5620821B2 (es) |
| CN (1) | CN101896472A (es) |
| AR (1) | AR069652A1 (es) |
| AU (1) | AU2008335880B2 (es) |
| BR (1) | BRPI0820856A2 (es) |
| CA (1) | CA2709203A1 (es) |
| CO (1) | CO6210735A2 (es) |
| CR (1) | CR11481A (es) |
| EA (1) | EA017918B1 (es) |
| IL (1) | IL206298A0 (es) |
| NZ (1) | NZ586121A (es) |
| TW (1) | TW200930370A (es) |
| WO (1) | WO2009074300A2 (es) |
| ZA (1) | ZA201004185B (es) |
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| TWI433674B (zh) | 2006-12-28 | 2014-04-11 | Infinity Discovery Inc | 環杷明（ｃｙｃｌｏｐａｍｉｎｅ）類似物類 |
| AU2008345151A1 (en) * | 2007-12-27 | 2009-07-09 | Infinity Pharmaceuticals, Inc. | Therapeutic cancer treatments |
| US20100297118A1 (en) * | 2007-12-27 | 2010-11-25 | Macdougall John | Therapeutic Cancer Treatments |
| CA2710858A1 (en) | 2007-12-27 | 2009-07-09 | Infinity Pharmaceuticals, Inc. | Methods for stereoselective reduction |
| US8193182B2 (en) | 2008-01-04 | 2012-06-05 | Intellikine, Inc. | Substituted isoquinolin-1(2H)-ones, and methods of use thereof |
| EP2424840B1 (en) * | 2009-04-27 | 2014-08-06 | Boehringer Ingelheim International GmbH | Cxcr3 receptor antagonists |
| KR20120026534A (ko) * | 2009-06-11 | 2012-03-19 | 시에나 바이오테크 에스.피.에이. | 헤지호그 경로 길항제 및 그의 치료적 적용 |
| AR077014A1 (es) * | 2009-06-19 | 2011-07-27 | Lilly Co Eli | Compuesto derivado de ftalazina 1,4-disustituida, composicion farmaceutica que lo comprende y uso para preparar un medicamento util para el tratamiento de cancer |
| ES2567134T3 (es) | 2009-08-05 | 2016-04-20 | Infinity Pharmaceuticals, Inc. | Transaminación enzimática de análogos de ciclopamina |
| WO2011084985A1 (en) | 2010-01-07 | 2011-07-14 | Boehringer Ingelheim International Gmbh | Cxcr3 receptor antagonists |
| US20110183948A1 (en) * | 2010-01-15 | 2011-07-28 | Infinity Pharmaceuticals, Inc. | Treatment of fibrotic conditions using hedgehog inhibitors |
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| US20160024051A1 (en) | 2013-03-15 | 2016-01-28 | Infinity Pharmaceuticals, Inc. | Salts and solid forms of isoquinolinones and composition comprising and methods of using the same |
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| MX373584B (es) | 2013-05-30 | 2020-05-05 | Infinity Pharmaceuticals Inc | Tratamiento de cánceres utilizando moduladores de la isoforma pi3 cinasa. |
| DK3003038T3 (da) | 2013-06-07 | 2019-11-11 | Scripps Research Inst | 2h-1,2,3-triazolderivater som inhibitorer af fibrose |
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| FR3017867A1 (fr) * | 2014-02-21 | 2015-08-28 | Inventiva | Nouveaux composes de type phenylazetidine carboxylate ou carboxamide |
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| WO2015168079A1 (en) | 2014-04-29 | 2015-11-05 | Infinity Pharmaceuticals, Inc. | Pyrimidine or pyridine derivatives useful as pi3k inhibitors |
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| KR102548066B1 (ko) | 2014-12-10 | 2023-06-26 | 더 스크립스 리서치 인스티튜트 | 섬유증의 소분자 억제제 |
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| CN109232533A (zh) * | 2017-09-28 | 2019-01-18 | 北京越之康泰生物医药科技有限公司 | 氮杂环类衍生物、其制备方法及其医药用途 |
| CN110494431B (zh) * | 2017-09-30 | 2022-11-04 | 苏州浦合医药科技有限公司 | 氮杂环类衍生物、其制备方法及其医药用途 |
| CN110016054B (zh) * | 2019-03-15 | 2021-10-22 | 四川大学 | 含磷氮苯并杂环结构的离子单体、用其阻燃的共聚酯型离聚物及它们的制备方法和应用 |
| CN114790177B (zh) * | 2021-01-26 | 2024-03-26 | 首都医科大学附属北京天坛医院 | 新型Hedgehog信号通路抑制剂 |
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| JP2002528531A (ja) | 1998-11-03 | 2002-09-03 | ビーエーエスエフ アクチェンゲゼルシャフト | 置換２−フェニルベンズイミダゾール、その製造法および使用 |
| ES2292812T3 (es) * | 2001-10-19 | 2008-03-16 | Ortho-Mcneil Pharmaceutical, Inc. | 2-fenil benzimidazol e imidazo-(4,5)-piridinas como inhibidores de cds1/chk2 y coadyuvantes para quimioterapia o radioterapia en el tratamiento del cancer. |
| CA2476594C (en) * | 2002-03-05 | 2012-10-09 | Transtech Pharma, Inc. | Mono-and bicyclic azole derivatives that inhibit the interaction of ligands with rage |
| KR20120026534A (ko) * | 2009-06-11 | 2012-03-19 | 시에나 바이오테크 에스.피.에이. | 헤지호그 경로 길항제 및 그의 치료적 적용 |
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2008
- 2008-12-10 BR BRPI0820856-5A patent/BRPI0820856A2/pt not_active IP Right Cessation
- 2008-12-10 JP JP2010537305A patent/JP5620821B2/ja not_active Expired - Fee Related
- 2008-12-10 EA EA201000784A patent/EA017918B1/ru not_active IP Right Cessation
- 2008-12-10 US US12/747,562 patent/US8592463B2/en not_active Expired - Fee Related
- 2008-12-10 CA CA2709203A patent/CA2709203A1/en not_active Abandoned
- 2008-12-10 CN CN2008801207308A patent/CN101896472A/zh active Pending
- 2008-12-10 EP EP08860550A patent/EP2227456A2/en not_active Withdrawn
- 2008-12-10 NZ NZ586121A patent/NZ586121A/en not_active IP Right Cessation
- 2008-12-10 WO PCT/EP2008/010470 patent/WO2009074300A2/en not_active Ceased
- 2008-12-10 AU AU2008335880A patent/AU2008335880B2/en not_active Ceased
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2010
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- 2010-06-10 IL IL206298A patent/IL206298A0/en unknown
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| EA201000784A1 (ru) | 2010-12-30 |
| WO2009074300A8 (en) | 2009-11-19 |
| US8592463B2 (en) | 2013-11-26 |
| IL206298A0 (en) | 2010-12-30 |
| EA017918B1 (ru) | 2013-04-30 |
| WO2009074300A2 (en) | 2009-06-18 |
| CN101896472A (zh) | 2010-11-24 |
| AU2008335880B2 (en) | 2014-03-13 |
| NZ586121A (en) | 2012-03-30 |
| US20100286114A1 (en) | 2010-11-11 |
| ZA201004185B (en) | 2011-10-26 |
| CR11481A (es) | 2010-10-15 |
| AU2008335880A1 (en) | 2009-06-18 |
| WO2009074300A3 (en) | 2009-10-01 |
| CO6210735A2 (es) | 2010-10-20 |
| EP2227456A2 (en) | 2010-09-15 |
| BRPI0820856A2 (pt) | 2019-05-14 |
| JP2011506366A (ja) | 2011-03-03 |
| CA2709203A1 (en) | 2009-06-18 |
| JP5620821B2 (ja) | 2014-11-05 |
| TW200930370A (en) | 2009-07-16 |
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