NZ588001A - Disubstituted phthalazine hedgehog pathway antagonists - Google Patents
Disubstituted phthalazine hedgehog pathway antagonistsInfo
- Publication number
- NZ588001A NZ588001A NZ588001A NZ58800109A NZ588001A NZ 588001 A NZ588001 A NZ 588001A NZ 588001 A NZ588001 A NZ 588001A NZ 58800109 A NZ58800109 A NZ 58800109A NZ 588001 A NZ588001 A NZ 588001A
- Authority
- NZ
- New Zealand
- Prior art keywords
- cancer
- fluoro
- trifluoromethyl
- pharmaceutically acceptable
- piperidin
- Prior art date
Links
- 239000005557 antagonist Substances 0.000 title abstract description 12
- 241000289669 Erinaceus europaeus Species 0.000 title abstract 2
- 230000037361 pathway Effects 0.000 title description 10
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 title description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 93
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 54
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 49
- 239000001257 hydrogen Substances 0.000 claims abstract description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 42
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 18
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 17
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- 201000011510 cancer Diseases 0.000 claims abstract description 10
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- 206010041067 Small cell lung cancer Diseases 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
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- 208000034578 Multiple myelomas Diseases 0.000 claims abstract description 7
- 206010035226 Plasma cell myeloma Diseases 0.000 claims abstract description 7
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- 201000002528 pancreatic cancer Diseases 0.000 claims abstract description 6
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 4
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- 238000004519 manufacturing process Methods 0.000 claims description 2
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- 230000002611 ovarian Effects 0.000 claims 1
- -1 Di-substituted phthalazines Chemical class 0.000 abstract description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 51
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- SNIABFMMCKVXSY-UHFFFAOYSA-N benzoylazanium;chloride Chemical compound Cl.NC(=O)C1=CC=CC=C1 SNIABFMMCKVXSY-UHFFFAOYSA-N 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 23
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 23
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- 239000002002 slurry Substances 0.000 description 6
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- NFPRIKGYZVNTTF-UHFFFAOYSA-N 2-(trifluoromethoxy)benzamide;hydrochloride Chemical compound Cl.NC(=O)C1=CC=CC=C1OC(F)(F)F NFPRIKGYZVNTTF-UHFFFAOYSA-N 0.000 description 5
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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| PCT/US2009/039065 WO2009134574A2 (en) | 2008-04-29 | 2009-04-01 | Disubstituted phthalazine hedgehog pathway antagonists |
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| EP2364185B1 (en) | 2008-11-03 | 2013-05-22 | Eli Lilly And Company | Disubstituted phthalazine hedgehog pathway antagonists |
| MX2011005176A (es) | 2008-11-17 | 2011-05-30 | Lilly Co Eli | Antagonistas de la trayectoria hedgehog de piridazinas tetrasustituidas. |
| CA2743483C (en) | 2008-11-17 | 2014-03-11 | Eli Lilly And Company | Tetrasubstituted pyridazine 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 |
| CA2781210A1 (en) * | 2009-11-18 | 2011-05-26 | Novartis Ag | Methods and compositions for treating solid tumors and other malignancies |
| CN102702108A (zh) * | 2012-06-27 | 2012-10-03 | 上海大学 | 1,2-二氢酞嗪类化合物及其合成方法 |
| EP2895474B1 (en) * | 2012-09-17 | 2019-12-11 | Duke University | Smoothened receptor modulators and methods of use thereof |
| CN102863393A (zh) * | 2012-09-26 | 2013-01-09 | 上海大学 | 1,2-二氢酞嗪类化合物及其合成方法 |
| GB201309508D0 (en) | 2013-05-28 | 2013-07-10 | Redx Pharma Ltd | Compounds |
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| CN105985321B (zh) * | 2015-02-11 | 2018-10-26 | 复旦大学 | 吡唑酞嗪化合物及其制备方法和用途 |
| CN105985320B (zh) * | 2015-02-11 | 2018-10-26 | 复旦大学 | 苄基酞嗪化合物及其制备方法和用途 |
| CN105985319B (zh) * | 2015-02-11 | 2019-02-26 | 复旦大学 | 芳基酞嗪化合物及其制备方法和用途 |
| 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 |
| US12605377B2 (en) | 2020-10-13 | 2026-04-21 | Endeavor Biomedicines, Inc. | Methods of treating fibrosis |
| JP2023546536A (ja) | 2020-10-13 | 2023-11-02 | エンデバー バイオメディシンズ， インコーポレイテッド | 線維症を処置する方法 |
| GEAP202516743A (en) * | 2022-09-23 | 2025-08-11 | Merck Sharp & Dohme Llc | Phthalazine derivatives useful as inhibitors of nod-like receptor protein 3 |
| WO2025188802A1 (en) | 2024-03-05 | 2025-09-12 | Endeavor Biomedicines, Inc. | Methods of improving lung function |
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| GB1293565A (en) * | 1969-05-03 | 1972-10-18 | Aspro Nicholas Ltd | Aminophthalazines and pharmaceutical compositions thereof |
| ATE203534T1 (de) * | 1996-01-15 | 2001-08-15 | Janssen Pharmaceutica Nv | Angiogenesis hemmende pyridazinamine |
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2009
- 2009-04-01 UA UAA201012722A patent/UA102250C2/ru unknown
- 2009-04-01 CA CA2723042A patent/CA2723042A1/en not_active Abandoned
- 2009-04-01 JP JP2011507512A patent/JP5442717B2/ja not_active Expired - Fee Related
- 2009-04-01 MX MX2010011948A patent/MX2010011948A/es active IP Right Grant
- 2009-04-01 EA EA201071248A patent/EA201071248A1/ru unknown
- 2009-04-01 BR BRPI0911618A patent/BRPI0911618A2/pt not_active IP Right Cessation
- 2009-04-01 KR KR1020107024209A patent/KR101260116B1/ko not_active Expired - Fee Related
- 2009-04-01 US US12/935,655 patent/US7981892B2/en not_active Expired - Fee Related
- 2009-04-01 NZ NZ588001A patent/NZ588001A/en not_active IP Right Cessation
- 2009-04-01 WO PCT/US2009/039065 patent/WO2009134574A2/en not_active Ceased
- 2009-04-01 CN CN2009801152085A patent/CN102066353B/zh not_active Expired - Fee Related
- 2009-04-01 EP EP09739376A patent/EP2294061A2/en not_active Withdrawn
- 2009-04-01 AU AU2009241561A patent/AU2009241561B2/en not_active Ceased
- 2009-04-01 MY MYPI2010005097A patent/MY159491A/en unknown
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2010
- 2010-09-16 IL IL208211A patent/IL208211A0/en unknown
- 2010-09-17 ZA ZA2010/06695A patent/ZA201006695B/en unknown
- 2010-10-11 DO DO2010000302A patent/DOP2010000302A/es unknown
- 2010-10-15 CR CR11741A patent/CR11741A/es unknown
- 2010-10-21 HN HN2010002157A patent/HN2010002157A/es unknown
- 2010-10-25 MA MA33284A patent/MA32349B1/fr unknown
- 2010-10-27 EC EC2010010577A patent/ECSP10010577A/es unknown
- 2010-11-11 CO CO10141824A patent/CO6300945A2/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| HN2010002157A (es) | 2014-09-08 |
| ECSP10010577A (es) | 2010-11-30 |
| ZA201006695B (en) | 2012-09-26 |
| KR20100126580A (ko) | 2010-12-01 |
| KR101260116B1 (ko) | 2013-05-02 |
| AU2009241561B2 (en) | 2013-05-16 |
| WO2009134574A2 (en) | 2009-11-05 |
| EP2294061A2 (en) | 2011-03-16 |
| DOP2010000302A (es) | 2010-11-15 |
| CA2723042A1 (en) | 2009-11-05 |
| CR11741A (es) | 2011-01-05 |
| EA201071248A1 (ru) | 2011-06-30 |
| CO6300945A2 (es) | 2011-07-21 |
| JP5442717B2 (ja) | 2014-03-12 |
| AU2009241561A1 (en) | 2009-11-05 |
| WO2009134574A3 (en) | 2014-09-04 |
| CN102066353A (zh) | 2011-05-18 |
| US20110046143A1 (en) | 2011-02-24 |
| MA32349B1 (fr) | 2011-06-01 |
| MX2010011948A (es) | 2010-12-14 |
| CN102066353B (zh) | 2013-12-11 |
| BRPI0911618A2 (pt) | 2019-09-24 |
| JP2011527666A (ja) | 2011-11-04 |
| UA102250C2 (ru) | 2013-06-25 |
| IL208211A0 (en) | 2010-12-30 |
| US7981892B2 (en) | 2011-07-19 |
| MY159491A (en) | 2017-01-13 |
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