CA2743483C - Tetrasubstituted pyridazine hedgehog pathway antagonists - Google Patents
Tetrasubstituted pyridazine hedgehog pathway antagonists Download PDFInfo
- Publication number
- CA2743483C CA2743483C CA2743483A CA2743483A CA2743483C CA 2743483 C CA2743483 C CA 2743483C CA 2743483 A CA2743483 A CA 2743483A CA 2743483 A CA2743483 A CA 2743483A CA 2743483 C CA2743483 C CA 2743483C
- Authority
- CA
- Canada
- Prior art keywords
- trifluoromethyl
- methyl
- piperidin
- cancer
- pharmaceutically acceptable
- 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.)
- Expired - Fee Related
Links
- 239000005557 antagonist Substances 0.000 title abstract description 10
- 230000037361 pathway Effects 0.000 title abstract description 8
- 241000289669 Erinaceus europaeus Species 0.000 title abstract 2
- 150000004892 pyridazines Chemical class 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims abstract description 38
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 28
- -1 di-F-substituted cyclohexyl Chemical group 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims abstract description 8
- 201000011510 cancer Diseases 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 7
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims abstract description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 84
- 206010004146 Basal cell carcinoma Diseases 0.000 claims description 6
- 206010060862 Prostate cancer Diseases 0.000 claims description 6
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 6
- 206010041067 Small cell lung cancer Diseases 0.000 claims description 6
- 208000000587 small cell lung carcinoma Diseases 0.000 claims description 6
- 208000003950 B-cell lymphoma Diseases 0.000 claims description 5
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 5
- 206010006187 Breast cancer Diseases 0.000 claims description 5
- 208000026310 Breast neoplasm Diseases 0.000 claims description 5
- 206010009944 Colon cancer Diseases 0.000 claims description 5
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 5
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 5
- 208000034578 Multiple myelomas Diseases 0.000 claims description 5
- 206010033128 Ovarian cancer Diseases 0.000 claims description 5
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 5
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 5
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 5
- 206010038389 Renal cancer Diseases 0.000 claims description 5
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 5
- 206010017758 gastric cancer Diseases 0.000 claims description 5
- 201000010982 kidney cancer Diseases 0.000 claims description 5
- 201000007270 liver cancer Diseases 0.000 claims description 5
- 208000014018 liver neoplasm Diseases 0.000 claims description 5
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 5
- 201000001441 melanoma Diseases 0.000 claims description 5
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 5
- 201000002528 pancreatic cancer Diseases 0.000 claims description 5
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 201000011549 stomach cancer Diseases 0.000 claims description 5
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 5
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 4
- 201000009036 biliary tract cancer Diseases 0.000 claims description 4
- 208000020790 biliary tract neoplasm Diseases 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 201000004101 esophageal cancer Diseases 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- XPRLKUVETLKKLZ-UHFFFAOYSA-N n-[1-[6-(4-fluorophenyl)-4,5-dimethylpyridazin-3-yl]piperidin-4-yl]-n-methyl-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C=1N=CC=C(C(F)(F)F)C=1C(=O)N(C)C(CC1)CCN1C(C(=C1C)C)=NN=C1C1=CC=C(F)C=C1 XPRLKUVETLKKLZ-UHFFFAOYSA-N 0.000 claims 2
- BWDIPHPUMOWMNP-UHFFFAOYSA-N n-[1-(4,5-dimethyl-6-phenylpyridazin-3-yl)piperidin-4-yl]-n-methyl-2-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C=1C=CN=C(C(F)(F)F)C=1C(=O)N(C)C(CC1)CCN1C(C(=C1C)C)=NN=C1C1=CC=CC=C1 BWDIPHPUMOWMNP-UHFFFAOYSA-N 0.000 claims 1
- IIKLWUQDTWOOBZ-UHFFFAOYSA-N n-[1-(4,5-dimethyl-6-phenylpyridazin-3-yl)piperidin-4-yl]-n-methyl-2-(trifluoromethyl)pyridine-3-carboxamide;dihydrochloride Chemical compound Cl.Cl.C=1C=CN=C(C(F)(F)F)C=1C(=O)N(C)C(CC1)CCN1C(C(=C1C)C)=NN=C1C1=CC=CC=C1 IIKLWUQDTWOOBZ-UHFFFAOYSA-N 0.000 claims 1
- GMVKNXLEUMOQPW-UHFFFAOYSA-N n-[1-(4,5-dimethyl-6-phenylpyridazin-3-yl)piperidin-4-yl]-n-methyl-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C=1N=CC=C(C(F)(F)F)C=1C(=O)N(C)C(CC1)CCN1C(C(=C1C)C)=NN=C1C1=CC=CC=C1 GMVKNXLEUMOQPW-UHFFFAOYSA-N 0.000 claims 1
- WPIDECBVBSVBTR-UHFFFAOYSA-N n-[1-(4,5-dimethyl-6-phenylpyridazin-3-yl)piperidin-4-yl]-n-methyl-4-(trifluoromethyl)pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C=1N=CC=C(C(F)(F)F)C=1C(=O)N(C)C(CC1)CCN1C(C(=C1C)C)=NN=C1C1=CC=CC=C1 WPIDECBVBSVBTR-UHFFFAOYSA-N 0.000 claims 1
- QCFSVDFDHTXNSC-UHFFFAOYSA-N n-[1-[6-(4-cyanophenyl)-4,5-dimethylpyridazin-3-yl]piperidin-4-yl]-n-methyl-2-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C=1C=CN=C(C(F)(F)F)C=1C(=O)N(C)C(CC1)CCN1C(C(=C1C)C)=NN=C1C1=CC=C(C#N)C=C1 QCFSVDFDHTXNSC-UHFFFAOYSA-N 0.000 claims 1
- MBSCWJBDUBGHEO-UHFFFAOYSA-N n-[1-[6-(4-cyanophenyl)-4,5-dimethylpyridazin-3-yl]piperidin-4-yl]-n-methyl-2-(trifluoromethyl)pyridine-3-carboxamide;dihydrochloride Chemical compound Cl.Cl.C=1C=CN=C(C(F)(F)F)C=1C(=O)N(C)C(CC1)CCN1C(C(=C1C)C)=NN=C1C1=CC=C(C#N)C=C1 MBSCWJBDUBGHEO-UHFFFAOYSA-N 0.000 claims 1
- ATTRAXBINPRSJB-UHFFFAOYSA-N n-[1-[6-(4-cyanophenyl)-4,5-dimethylpyridazin-3-yl]piperidin-4-yl]-n-methyl-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C=1N=CC=C(C(F)(F)F)C=1C(=O)N(C)C(CC1)CCN1C(C(=C1C)C)=NN=C1C1=CC=C(C#N)C=C1 ATTRAXBINPRSJB-UHFFFAOYSA-N 0.000 claims 1
- GJTUWTHVFJFIMO-UHFFFAOYSA-N n-[1-[6-(4-cyanophenyl)-4,5-dimethylpyridazin-3-yl]piperidin-4-yl]-n-methyl-4-(trifluoromethyl)pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C=1N=CC=C(C(F)(F)F)C=1C(=O)N(C)C(CC1)CCN1C(C(=C1C)C)=NN=C1C1=CC=C(C#N)C=C1 GJTUWTHVFJFIMO-UHFFFAOYSA-N 0.000 claims 1
- OUOFEKKACPVGSL-UHFFFAOYSA-N n-[1-[6-(4-fluorophenyl)-4,5-dimethylpyridazin-3-yl]piperidin-4-yl]-n,1-dimethyl-5-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C1=NN(C)C(C(F)(F)F)=C1C(=O)N(C)C(CC1)CCN1C(C(=C1C)C)=NN=C1C1=CC=C(F)C=C1 OUOFEKKACPVGSL-UHFFFAOYSA-N 0.000 claims 1
- OMKGKESTUZYPPU-UHFFFAOYSA-N n-[1-[6-(4-fluorophenyl)-4,5-dimethylpyridazin-3-yl]piperidin-4-yl]-n,1-dimethyl-5-(trifluoromethyl)pyrazole-4-carboxamide;dihydrochloride Chemical compound Cl.Cl.C1=NN(C)C(C(F)(F)F)=C1C(=O)N(C)C(CC1)CCN1C(C(=C1C)C)=NN=C1C1=CC=C(F)C=C1 OMKGKESTUZYPPU-UHFFFAOYSA-N 0.000 claims 1
- OYZIFZSMJFNNSH-UHFFFAOYSA-N n-[1-[6-(4-fluorophenyl)-4,5-dimethylpyridazin-3-yl]piperidin-4-yl]-n-methyl-2-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C=1C=CN=C(C(F)(F)F)C=1C(=O)N(C)C(CC1)CCN1C(C(=C1C)C)=NN=C1C1=CC=C(F)C=C1 OYZIFZSMJFNNSH-UHFFFAOYSA-N 0.000 claims 1
- HZULYVWAEOUXLB-UHFFFAOYSA-N n-[1-[6-(4-fluorophenyl)-4,5-dimethylpyridazin-3-yl]piperidin-4-yl]-n-methyl-2-(trifluoromethyl)pyridine-3-carboxamide;dihydrochloride Chemical compound Cl.Cl.C=1C=CN=C(C(F)(F)F)C=1C(=O)N(C)C(CC1)CCN1C(C(=C1C)C)=NN=C1C1=CC=C(F)C=C1 HZULYVWAEOUXLB-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 1
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Classifications
-
- 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
- C07D401/04—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 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11533208P | 2008-11-17 | 2008-11-17 | |
| US61/115,332 | 2008-11-17 | ||
| PCT/US2009/063370 WO2010056588A1 (en) | 2008-11-17 | 2009-11-05 | Tetrasubstituted pyridazine hedgehog pathway antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2743483A1 CA2743483A1 (en) | 2010-05-20 |
| CA2743483C true CA2743483C (en) | 2014-03-11 |
Family
ID=41722877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2743483A Expired - Fee Related CA2743483C (en) | 2008-11-17 | 2009-11-05 | Tetrasubstituted pyridazine hedgehog pathway antagonists |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US8507490B2 (OSRAM) |
| EP (1) | EP2358698B1 (OSRAM) |
| JP (1) | JP5518887B2 (OSRAM) |
| KR (1) | KR101342184B1 (OSRAM) |
| CN (1) | CN102216285B (OSRAM) |
| AU (1) | AU2009314349B2 (OSRAM) |
| BR (1) | BRPI0921782A2 (OSRAM) |
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Families Citing this family (15)
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| BRPI0714872A2 (pt) * | 2006-07-17 | 2013-03-19 | Syngenta Participations Ag | derivados de piridazina |
| NZ588001A (en) | 2008-04-29 | 2012-06-29 | Lilly Co Eli | Disubstituted phthalazine hedgehog pathway antagonists |
| AU2009320251C1 (en) | 2008-11-03 | 2013-08-15 | Eli Lilly And Company | Disubstituted phthalazine Hedgehog pathway antagonists |
| US8445493B2 (en) | 2008-11-17 | 2013-05-21 | Eli Lilly And Company | Tetrasubstituted pyridazines hedgehog pathway antagonists |
| 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 |
| GB201309508D0 (en) | 2013-05-28 | 2013-07-10 | Redx Pharma Ltd | Compounds |
| US9814703B2 (en) | 2013-11-14 | 2017-11-14 | The Board Of Trustees Of The Leland Stanford Junior University | Methods for treating cancer by activation of BMP signaling |
| GB2528298A (en) * | 2014-07-16 | 2016-01-20 | Redx Pharma Plc | Compounds |
| CN105130980B (zh) * | 2015-09-09 | 2018-05-22 | 沈阳药科大学 | N-3-苯并咪唑噻唑胺类衍生物及其制备方法与应用 |
| CN107163028B (zh) * | 2017-05-24 | 2019-07-12 | 东南大学 | 一种苯甲酰胺类Hedgehog抑制剂及其制备方法和应用 |
| CN110208424A (zh) * | 2019-06-28 | 2019-09-06 | 江苏恒生检测有限公司 | 一种农药氟啶虫酰胺中含有杂质的分析方法 |
| WO2021071981A1 (en) * | 2019-10-08 | 2021-04-15 | Skyhawk Therapeutics, Inc. | Compounds for modulating splicing |
| KR20230107568A (ko) | 2020-10-13 | 2023-07-17 | 엔데버 바이오메디신스, 인크. | 섬유증 치료 방법 |
| WO2023034836A1 (en) * | 2021-08-30 | 2023-03-09 | Remix Therapeutics Inc. | Compounds and methods for modulating splicing |
| US12447148B2 (en) | 2024-03-05 | 2025-10-21 | Endeavor Biomedicines, Inc. | Methods of improving lung function |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1293565A (en) | 1969-05-03 | 1972-10-18 | Aspro Nicholas Ltd | Aminophthalazines and pharmaceutical compositions thereof |
| CN1104430C (zh) | 1996-01-15 | 2003-04-02 | 詹森药业有限公司 | 抑制血管生成的哒嗪胺 |
| CA2326654C (en) | 1998-04-09 | 2010-11-09 | Johns Hopkins University School Of Medicine | Use of steroidal alkaloid derivatives as inhibitors of hedgehog signaling pathways |
| US6432970B2 (en) | 1998-04-09 | 2002-08-13 | Johns Hopkins University School Of Medicine | Inhibitors of hedgehog signaling pathways, compositions and uses related thereto |
| WO2000074706A1 (en) | 1999-06-08 | 2000-12-14 | Lorantis Limited | Therapeutic use of an inhibitor of a hedgehog or a hedgehog-related signalling pathway |
| ATE404200T1 (de) | 2002-04-22 | 2008-08-15 | Univ Johns Hopkins Med | Modulatoren von hedgehog signalpfaden, zusammensetzungen und verwandte verwendungen |
| WO2004020599A2 (en) | 2002-08-29 | 2004-03-11 | Curis, Inc. | Hedgehog antagonists, methods and uses related thereto |
| US8067608B2 (en) | 2003-09-29 | 2011-11-29 | The Johns Hopkins University | Hedgehog pathway antagonists |
| TW200533356A (en) | 2004-02-24 | 2005-10-16 | Mitsubishi Pharma Corp | Fused pyridazine derivatives |
| CA2564996A1 (en) | 2004-05-08 | 2006-01-12 | Taeyoung Yoon | 3-aryl-5,6-disubstituted pyridazines |
| EP1789390B1 (en) | 2004-09-02 | 2011-11-09 | Genentech, Inc. | Pyridyl inhibitors of hedgehog signalling |
| EP1900731A1 (de) | 2006-09-07 | 2008-03-19 | Bayer Schering Pharma Aktiengesellschaft | N-(1-Phthalazin-1-yl-piperidin-4-yl)-amide als EP2-Rezeptor Modulatoren |
| NZ579402A (en) | 2007-03-15 | 2012-03-30 | Novartis Ag | Organic compounds for diagnosis and treatment of pathologies relating to the Hedgehog pathway |
| AU2008269128B2 (en) | 2007-06-25 | 2012-08-02 | Amgen Inc. | Phthalazine compounds, compositions and methods of use |
| ES2392157T3 (es) | 2007-09-07 | 2012-12-05 | Amgen Inc. | Piridazinas anilladas para el tratamiento de tumores dirigidos por señalización Hedgehog inapropiada |
| NZ588001A (en) | 2008-04-29 | 2012-06-29 | Lilly Co Eli | Disubstituted phthalazine hedgehog pathway antagonists |
| US20100041663A1 (en) | 2008-07-18 | 2010-02-18 | Novartis Ag | Organic Compounds as Smo Inhibitors |
| AU2009320251C1 (en) | 2008-11-03 | 2013-08-15 | Eli Lilly And Company | Disubstituted phthalazine Hedgehog pathway antagonists |
| US8445493B2 (en) | 2008-11-17 | 2013-05-21 | Eli Lilly And Company | Tetrasubstituted pyridazines hedgehog pathway antagonists |
| 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 |
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- 2009-11-05 MX MX2011005177A patent/MX2011005177A/es active IP Right Grant
- 2009-11-05 PT PT09752059T patent/PT2358698E/pt unknown
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- 2009-11-05 EP EP09752059A patent/EP2358698B1/en not_active Not-in-force
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- 2009-11-05 KR KR1020117011148A patent/KR101342184B1/ko not_active Expired - Fee Related
- 2009-11-05 WO PCT/US2009/063370 patent/WO2010056588A1/en not_active Ceased
- 2009-11-05 EA EA201170699A patent/EA017386B1/ru not_active IP Right Cessation
- 2009-11-05 PL PL09752059T patent/PL2358698T3/pl unknown
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2012
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Also Published As
| Publication number | Publication date |
|---|---|
| HRP20120762T1 (hr) | 2012-10-31 |
| EA201170699A1 (ru) | 2011-12-30 |
| BRPI0921782A2 (pt) | 2019-09-24 |
| SI2358698T1 (sl) | 2012-11-30 |
| CN102216285B (zh) | 2014-08-13 |
| US8507490B2 (en) | 2013-08-13 |
| CA2743483A1 (en) | 2010-05-20 |
| ES2392759T3 (es) | 2012-12-13 |
| EP2358698B1 (en) | 2012-09-05 |
| MX2011005177A (es) | 2011-05-30 |
| KR20110070920A (ko) | 2011-06-24 |
| PT2358698E (pt) | 2012-10-24 |
| KR101342184B1 (ko) | 2013-12-19 |
| JP5518887B2 (ja) | 2014-06-11 |
| AU2009314349A1 (en) | 2010-05-20 |
| AU2009314349B2 (en) | 2013-04-18 |
| EA017386B1 (ru) | 2012-12-28 |
| CN102216285A (zh) | 2011-10-12 |
| US20110263602A1 (en) | 2011-10-27 |
| EP2358698A1 (en) | 2011-08-24 |
| PL2358698T3 (pl) | 2013-01-31 |
| CY1113377T1 (el) | 2016-06-22 |
| WO2010056588A1 (en) | 2010-05-20 |
| DK2358698T3 (da) | 2012-10-08 |
| JP2012509263A (ja) | 2012-04-19 |
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