JP2013506671A - C−metキナーゼ阻害剤の結晶性塩酸塩 - Google Patents
C−metキナーゼ阻害剤の結晶性塩酸塩 Download PDFInfo
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- JP2013506671A JP2013506671A JP2012532126A JP2012532126A JP2013506671A JP 2013506671 A JP2013506671 A JP 2013506671A JP 2012532126 A JP2012532126 A JP 2012532126A JP 2012532126 A JP2012532126 A JP 2012532126A JP 2013506671 A JP2013506671 A JP 2013506671A
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- pyridin
- hcl salt
- compound
- crystalline
- cyclohepta
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title description 15
- 229940125895 MET kinase inhibitor Drugs 0.000 title description 2
- 150000003840 hydrochlorides Chemical class 0.000 claims description 25
- -1 Methyl-1H-pyrazol-4-yl Chemical group 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 8
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 7
- 230000008018 melting Effects 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims description 4
- 230000005855 radiation Effects 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 2
- 229910052802 copper Inorganic materials 0.000 claims 2
- 239000010949 copper Substances 0.000 claims 2
- BKIQDRGTLKPYCL-UHFFFAOYSA-N 1-[2-(1-methylpyrazol-4-yl)-11-oxobenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]-n-(pyridin-2-ylmethyl)methanesulfonamide;hydrochloride Chemical compound Cl.C1=NN(C)C=C1C1=CN=C(C=CC=2C(=CC(CS(=O)(=O)NCC=3N=CC=CC=3)=CC=2)C2=O)C2=C1 BKIQDRGTLKPYCL-UHFFFAOYSA-N 0.000 claims 1
- 229940126062 Compound A Drugs 0.000 abstract description 68
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 abstract description 68
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 abstract description 3
- 239000003112 inhibitor Substances 0.000 abstract description 3
- 239000012453 solvate Substances 0.000 description 17
- 238000002441 X-ray diffraction Methods 0.000 description 13
- PDBXHPORMXSXKO-UHFFFAOYSA-N 8-benzyl-7-[2-[ethyl(2-hydroxyethyl)amino]ethyl]-1,3-dimethylpurine-2,6-dione;hydron;chloride Chemical class Cl.N=1C=2N(C)C(=O)N(C)C(=O)C=2N(CCN(CCO)CC)C=1CC1=CC=CC=C1 PDBXHPORMXSXKO-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000006184 cosolvent Substances 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 150000004682 monohydrates Chemical class 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000005384 cross polarization magic-angle spinning Methods 0.000 description 2
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229940043355 kinase inhibitor Drugs 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 101100481033 Arabidopsis thaliana TGA7 gene Proteins 0.000 description 1
- 206010007572 Cardiac hypertrophy Diseases 0.000 description 1
- 208000006029 Cardiomegaly Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 238000005004 MAS NMR spectroscopy Methods 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007707 calorimetry Methods 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000005388 cross polarization Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000001622 two pulse phase modulation pulse sequence Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
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
- C07D401/14—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
に安定であるとわかった。結晶性一HCl塩水和物は、低い相対湿度に曝露される、又は高温で加熱されると、脱水し、一HCl塩無水物形態IIに変換する。
Claims (10)
- 結晶性1−[3−(1−メチル−1H−ピラゾール−4−イル)−5−オキソ−5H−ベンゾ[4,5]シクロヘプタ[1,2−b]ピリジン−7−イル]−N−(ピリジン−2−イルメチル)メタンスルホンアミド塩酸塩。
- 5.30、5.05、及び4.30オングストロームのd−スペーシングに対応する、銅Kα照射を使用して集められた粉末X線回折パターンを特徴とする、1−[3−(1−メチル−1H−ピラゾール−4−イル)−5−オキソ−5H−ベンゾ[4,5]シクロヘプタ[1,2−b]ピリジン−7−イル]−N−(ピリジン−2−イルメチル)メタンスルホンアミドの新規結晶性一HCl塩無水物形態I。
- 7.28、5.72、及び4.61オングストロームのd−スペーシングに対応する反射をさらに特徴とする、請求項1に記載の1−[3−(1−メチル−1H−ピラゾール−4−イル)−5−オキソ−5H−ベンゾ[4,5]シクロヘプタ[1,2−b]ピリジン−7−イル]−N−(ピリジン−2−イルメチル)メタンスルホンアミドの新規結晶性一HCl塩無水物の形態I。
- 6.48、4.41、及び3.42オングストロームのd−スペーシングに対応する反射をさらに特徴とする、請求項1に記載の1−[3−(1−メチル−1H−ピラゾール−4−イル)−5−オキソ−5H−ベンゾ[4,5]シクロヘプタ[1,2−b]ピリジン−7−イル]−N−(ピリジン−2−イルメチル)メタンスルホンアミドの新規結晶性一HCl塩無水物の形態I。
- 133.6、136.0、及び126.7p.p.mでシグナルを示す固体炭素−13CPMAS核磁気共鳴スペクトルを特徴とする、請求項2に記載の1−[3−(1−メチル−1H−ピラゾール−4−イル)−5−オキソ−5H−ベンゾ[4,5]シクロヘプタ[1,2−b]ピリジン−7−イル]−N−(ピリジン−2−イルメチル)メタンスルホンアミドの新規結晶性一HCl塩無水物形態I。
- 131.0、147.9、及び118.9p.p.mでのシグナルをさらに特徴とする、請求項5に記載の1−[3−(1−メチル−1H−ピラゾール−4−イル)−5−オキソ−5H−ベンゾ[4,5]シクロヘプタ[1,2−b]ピリジン−7−イル]−N−(ピリジン−2−イルメチル)メタンスルホンアミドの新規結晶性一HCl塩無水物形態I。
- 244.7℃での融解開始を特徴とする、請求項6に記載の1−[3−(1−メチル−1H−ピラゾール−4−イル)−5−オキソ−5H−ベンゾ[4,5]シクロヘプタ[1,2−b]ピリジン−7−イル]−N−(ピリジン−2−イルメチル)メタンスルホンアミドの新規結晶性一HCl塩無水物形態I。
- 12.58、6.31、及び5.18オングストロームのd−スペーシングに対応する、銅Kα照射を使用して集められた粉末X線回折パターンを特徴とする、1−[3−(1−メチル−1H−ピラゾール−4−イル)−5−オキソ−5H−ベンゾ[4,5]シクロヘプタ[1,2−b]ピリジン−7−イル]−N−(ピリジン−2−イルメチル)メタンスルホンアミドの新規結晶性1.6−HCl塩水和物。
- 5.05、4.63、及び4.54オングストロームのd−スペーシングをさらに特徴とする、請求項8に記載の1−[3−(1−メチル−1H−ピラゾール−4−イル)−5−オキソ−5H−ベンゾ[4,5]シクロヘプタ[1,2−b]ピリジン−7−イル]−N−(ピリジン−2−イルメチル)メタンスルホンアミドの新規結晶性1.6−HCl塩水和物。
- 219.2℃での融解開始を特徴とする、請求項9に記載の1−[3−(1−メチル−1H−ピラゾール−4−イル)−5−オキソ−5H−ベンゾ[4,5]シクロヘプタ[1,2−b]ピリジン−7−イル]−N−(ピリジン−2−イルメチル)メタンスルホンアミドの新規結晶性1.6−HCl塩水和物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US24702809P | 2009-09-30 | 2009-09-30 | |
US61/247,028 | 2009-09-30 | ||
PCT/US2010/049556 WO2011041157A1 (en) | 2009-09-30 | 2010-09-21 | Crystalline hydrochloride salts of c-met kinase inhibitors |
Publications (2)
Publication Number | Publication Date |
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JP2013506671A true JP2013506671A (ja) | 2013-02-28 |
JP5785171B2 JP5785171B2 (ja) | 2015-09-24 |
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JP2012532126A Active JP5785171B2 (ja) | 2009-09-30 | 2010-09-21 | C−metキナーゼ阻害剤の結晶性塩酸塩 |
Country Status (6)
Country | Link |
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US (1) | US8674105B2 (ja) |
EP (1) | EP2482821A4 (ja) |
JP (1) | JP5785171B2 (ja) |
AU (1) | AU2010300930B2 (ja) |
CA (1) | CA2771338A1 (ja) |
WO (1) | WO2011041157A1 (ja) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2009512698A (ja) * | 2006-07-10 | 2009-03-26 | メルク エンド カムパニー インコーポレーテッド | チロシンキナーゼインヒビター |
JP2013506648A (ja) * | 2009-09-30 | 2013-02-28 | メルク シャープ エンド ドーム リミテッド | c−METキナーゼ阻害剤の製剤 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2003084931A1 (en) | 2002-04-02 | 2003-10-16 | Merck & Co., Inc. | 5h-benzo[4,5]cyclohepta[1,2-b]pyridine nmda/nr2b antagonists |
TW200738638A (en) | 2005-06-23 | 2007-10-16 | Merck & Co Inc | Tyrosine kinase inhibitors |
JP4119478B1 (ja) | 2005-06-23 | 2008-07-16 | メルク エンド カムパニー インコーポレーテッド | チロシンキナーゼインヒビター |
WO2008067119A2 (en) | 2006-11-27 | 2008-06-05 | Smithkline Beecham Corporation | Novel compounds |
-
2010
- 2010-09-21 WO PCT/US2010/049556 patent/WO2011041157A1/en active Application Filing
- 2010-09-21 EP EP10821042A patent/EP2482821A4/en not_active Withdrawn
- 2010-09-21 JP JP2012532126A patent/JP5785171B2/ja active Active
- 2010-09-21 AU AU2010300930A patent/AU2010300930B2/en active Active
- 2010-09-21 US US13/498,605 patent/US8674105B2/en active Active
- 2010-09-21 CA CA2771338A patent/CA2771338A1/en not_active Abandoned
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2009512698A (ja) * | 2006-07-10 | 2009-03-26 | メルク エンド カムパニー インコーポレーテッド | チロシンキナーゼインヒビター |
JP2013506648A (ja) * | 2009-09-30 | 2013-02-28 | メルク シャープ エンド ドーム リミテッド | c−METキナーゼ阻害剤の製剤 |
Also Published As
Publication number | Publication date |
---|---|
JP5785171B2 (ja) | 2015-09-24 |
WO2011041157A1 (en) | 2011-04-07 |
AU2010300930B2 (en) | 2014-09-11 |
US8674105B2 (en) | 2014-03-18 |
EP2482821A4 (en) | 2013-03-06 |
US20120184744A1 (en) | 2012-07-19 |
CA2771338A1 (en) | 2011-04-07 |
AU2010300930A1 (en) | 2012-04-26 |
EP2482821A1 (en) | 2012-08-08 |
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