JP2016523258A5 - - Google Patents
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- Publication number
- JP2016523258A5 JP2016523258A5 JP2016521847A JP2016521847A JP2016523258A5 JP 2016523258 A5 JP2016523258 A5 JP 2016523258A5 JP 2016521847 A JP2016521847 A JP 2016521847A JP 2016521847 A JP2016521847 A JP 2016521847A JP 2016523258 A5 JP2016523258 A5 JP 2016523258A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- crystals
- powder diffraction
- diffraction pattern
- pattern
- 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.)
- Granted
Links
- 239000013078 crystal Substances 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
- 239000012044 organic layer Substances 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- 239000011975 tartaric acid Substances 0.000 claims description 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 17
- 229940126062 Compound A Drugs 0.000 claims 17
- 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 claims 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 15
- 238000000113 differential scanning calorimetry Methods 0.000 claims 15
- 239000012453 solvate Substances 0.000 claims 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 9
- 239000012458 free base Substances 0.000 claims 9
- BBIPVJCGIASXJB-PKTZIBPZSA-N (11R,15S)-5-anilino-4-[[4-(6-fluoropyridin-2-yl)phenyl]methyl]-8-methyl-1,3,4,8,10-pentazatetracyclo[7.6.0.02,6.011,15]pentadeca-2,5,9-trien-7-one Chemical compound N1([C@H]2CCC[C@H]2N=C1N(C(C1=C2NC=3C=CC=CC=3)=O)C)C1=NN2CC(C=C1)=CC=C1C1=CC=CC(F)=N1 BBIPVJCGIASXJB-PKTZIBPZSA-N 0.000 claims 8
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- OFCNXPDARWKPPY-UHFFFAOYSA-N allopurinol Chemical compound OC1=NC=NC2=C1C=NN2 OFCNXPDARWKPPY-UHFFFAOYSA-N 0.000 claims 6
- 239000000243 solution Substances 0.000 claims 5
- 238000003756 stirring Methods 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 150000004712 monophosphates Chemical class 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- JTBBWRKSUYCPFY-UHFFFAOYSA-N 2,3-dihydro-1h-pyrimidin-4-one Chemical compound O=C1NCNC=C1 JTBBWRKSUYCPFY-UHFFFAOYSA-N 0.000 claims 2
- -1 6-fluoropyridin-2-yl Chemical group 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 239000000843 powder Substances 0.000 claims 2
- MTAODLNXWYIKSO-UHFFFAOYSA-N 2-fluoropyridine Chemical compound FC1=CC=CC=N1 MTAODLNXWYIKSO-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- ZQJUAPPNCFBJJW-UHFFFAOYSA-N 1,3,4,8,10-pentazatricyclo[7.3.0.02,6]dodeca-2,4,6,8,10-pentaene Chemical compound C1=C2C=NN=C2N2CC=NC2=N1 ZQJUAPPNCFBJJW-UHFFFAOYSA-N 0.000 description 1
- DVMILACIDBEACH-UHFFFAOYSA-N 6-fluoropyridine Chemical compound FC1=C=CC=C[N]1 DVMILACIDBEACH-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361838105P | 2013-06-21 | 2013-06-21 | |
| US61/838,105 | 2013-06-21 | ||
| US201361919424P | 2013-12-20 | 2013-12-20 | |
| US61/919,424 | 2013-12-20 | ||
| PCT/US2014/043422 WO2014205354A2 (en) | 2013-06-21 | 2014-06-20 | Free base crystals |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019104412A Division JP2019189618A (ja) | 2013-06-21 | 2019-06-04 | 遊離塩基結晶 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016523258A JP2016523258A (ja) | 2016-08-08 |
| JP2016523258A5 true JP2016523258A5 (enExample) | 2018-03-08 |
| JP6865036B2 JP6865036B2 (ja) | 2021-04-28 |
Family
ID=52105535
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016521847A Active JP6865036B2 (ja) | 2013-06-21 | 2014-06-20 | 遊離塩基結晶 |
| JP2019104412A Pending JP2019189618A (ja) | 2013-06-21 | 2019-06-04 | 遊離塩基結晶 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019104412A Pending JP2019189618A (ja) | 2013-06-21 | 2019-06-04 | 遊離塩基結晶 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US9630971B2 (enExample) |
| EP (2) | EP3010509B1 (enExample) |
| JP (2) | JP6865036B2 (enExample) |
| KR (2) | KR20160040522A (enExample) |
| CN (3) | CN112851683A (enExample) |
| AU (1) | AU2014284224B2 (enExample) |
| BR (1) | BR112015032132B1 (enExample) |
| CA (1) | CA2916393C (enExample) |
| ES (1) | ES2894770T3 (enExample) |
| IL (2) | IL267331B2 (enExample) |
| MX (2) | MX2015017972A (enExample) |
| RU (1) | RU2675851C2 (enExample) |
| WO (1) | WO2014205354A2 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10561656B2 (en) | 2011-06-10 | 2020-02-18 | Intra-Cellular Therapies, Inc. | Organic compounds |
| AR091507A1 (es) | 2012-06-21 | 2015-02-11 | Intra Cellular Therapies Inc | SALES DE (6aR,9aS)-5,6a,7,8,9,9a-HEXAHIDRO-5-METIL-3-(FENILAMINO)-2-((4-(6-FLUOROPIRIDIN-2-IL)FENIL)METIL)-CICLOPENT[4,5]IMIDAZO[1,2-a]PIRAZOLO[4,3-e]PIRIMIDIN-4(2H)-ONA |
| EP3010509B1 (en) | 2013-06-21 | 2021-07-28 | Intra-Cellular Therapies, Inc. | Free base crystals |
| EP4413980A3 (en) | 2019-09-03 | 2024-10-30 | Intra-Cellular Therapies, Inc. | Novel compounds |
| US12435093B2 (en) | 2020-05-06 | 2025-10-07 | Intra-Cellular Therapies, Inc. | Free base crystals |
| JP2023535224A (ja) * | 2020-07-26 | 2023-08-16 | イントラ－セルラー・セラピーズ・インコーポレイテッド | 新規使用 |
| EP4395767A4 (en) * | 2021-09-03 | 2025-07-23 | Intra Cellular Therapies Inc | CO-CRYSTALS |
| US20250144029A1 (en) * | 2022-01-27 | 2025-05-08 | Intra-Cellular Therapies, Inc. | Novel compositions |
| WO2023233410A1 (en) * | 2022-06-02 | 2023-12-07 | Biosight Ltd. | Crystalline form of aspacytarabine intermediate |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9412571D0 (en) | 1994-06-22 | 1994-08-10 | Celltech Ltd | Chemical compounds |
| US5471001A (en) * | 1994-12-15 | 1995-11-28 | E. I. Du Pont De Nemours And Company | Crystallization of adipic acid |
| GB9624615D0 (en) | 1996-11-26 | 1997-01-15 | Zeneca Ltd | Chrystallisation process |
| TWI265925B (en) | 1999-10-11 | 2006-11-11 | Pfizer | Pyrazolo[4,3-d]pyrimidin-7-ones useful in inhibiting type 5 cyclic guanosine 3',5'-monophosphate phosphodiesterases(cGMP PDE5), process and intermediates for their preparation, their uses and composition comprising them |
| WO2003066590A1 (en) | 2002-02-08 | 2003-08-14 | Ono Pharmaceutical Co., Ltd. | Piperidine derivative compounds and drugs containing the compounds as the active ingredient |
| EP1613747A1 (en) * | 2003-03-31 | 2006-01-11 | Pfizer Products Inc. | Crystal structure of 3 ,5 -cyclic nucleotide phosphodiesterase 1b (pde1b) and uses thereof |
| AU2004268024B2 (en) | 2003-09-02 | 2007-07-12 | Merck Sharp & Dohme Llc | Novel crystalline forms of a phosphoric acid salt of a dipeptidyl peptidase-IV inhibitor |
| DK1794126T3 (da) * | 2004-09-27 | 2013-06-24 | Acadia Pharm Inc | Krystallinsk form af N-(-4-fluorbenzyl)-N-(1-methylpiperidn-4-yl)-N'-(4-(2-methylpropyloxy)phenylmethyl)carbamid-hemitartrat |
| CN101248050B (zh) | 2005-06-06 | 2013-07-17 | 武田药品工业株式会社 | 有机化合物 |
| WO2008063505A1 (en) | 2006-11-13 | 2008-05-29 | Intra-Cellular Therapies, Inc. | Organic compounds |
| US9006258B2 (en) | 2006-12-05 | 2015-04-14 | Intra-Cellular Therapies, Inc. | Method of treating female sexual dysfunction with a PDE1 inhibitor |
| WO2009075784A1 (en) | 2007-12-06 | 2009-06-18 | Intra-Cellular Therapies, Inc. | Organic compounds |
| US20120070443A1 (en) | 2008-12-02 | 2012-03-22 | University Of Utah Research Foundation | Pde1 as a target therapeutic in heart disease |
| EP2367429B1 (en) | 2008-12-06 | 2017-06-07 | Intra-Cellular Therapies, Inc. | Organic compounds |
| EP2358204B1 (en) | 2008-12-06 | 2015-08-05 | Intra-Cellular Therapies, Inc. | 4,5,7,8-tetrahydro-4-oxo-2H-imidazo[1,2-a]pyrrolo[3,4-e]pyrimidine compounds as PDE1 inhibitors. |
| CN102232077A (zh) | 2008-12-06 | 2011-11-02 | 细胞内治疗公司 | 有机化合物 |
| EP2400970A4 (en) | 2009-02-25 | 2012-07-18 | Intra Cellular Therapies Inc | PDE-1-HEMMER FOR EYE DRESSING |
| US9468637B2 (en) * | 2009-05-13 | 2016-10-18 | Intra-Cellular Therapies, Inc. | Organic compounds |
| JP2013507360A (ja) | 2009-10-08 | 2013-03-04 | イントラ−セルラー・セラピーズ・インコーポレイテッド | ホスホジエステラーゼ１−標的トレーサーおよび方法 |
| JP5911854B2 (ja) | 2010-05-31 | 2016-04-27 | イントラ−セルラー・セラピーズ・インコーポレイテッドＩｎｔｒａ−Ｃｅｌｌｕｌａｒ Ｔｈｅｒａｐｉｅｓ， Ｉｎｃ． | 有機化合物 |
| TW201206937A (en) | 2010-05-31 | 2012-02-16 | Intra Cellular Therapies Inc | Organic compounds |
| US10561656B2 (en) | 2011-06-10 | 2020-02-18 | Intra-Cellular Therapies, Inc. | Organic compounds |
| AR091507A1 (es) * | 2012-06-21 | 2015-02-11 | Intra Cellular Therapies Inc | SALES DE (6aR,9aS)-5,6a,7,8,9,9a-HEXAHIDRO-5-METIL-3-(FENILAMINO)-2-((4-(6-FLUOROPIRIDIN-2-IL)FENIL)METIL)-CICLOPENT[4,5]IMIDAZO[1,2-a]PIRAZOLO[4,3-e]PIRIMIDIN-4(2H)-ONA |
| EP3010509B1 (en) | 2013-06-21 | 2021-07-28 | Intra-Cellular Therapies, Inc. | Free base crystals |
-
2014
- 2014-06-20 EP EP14812994.3A patent/EP3010509B1/en active Active
- 2014-06-20 BR BR112015032132-1A patent/BR112015032132B1/pt active IP Right Grant
- 2014-06-20 AU AU2014284224A patent/AU2014284224B2/en active Active
- 2014-06-20 ES ES14812994T patent/ES2894770T3/es active Active
- 2014-06-20 CA CA2916393A patent/CA2916393C/en active Active
- 2014-06-20 US US14/900,589 patent/US9630971B2/en active Active
- 2014-06-20 CN CN202110144523.3A patent/CN112851683A/zh active Pending
- 2014-06-20 CN CN201480046150.4A patent/CN105658222A/zh active Pending
- 2014-06-20 EP EP20165092.6A patent/EP3702358A1/en active Pending
- 2014-06-20 RU RU2016101630A patent/RU2675851C2/ru active
- 2014-06-20 JP JP2016521847A patent/JP6865036B2/ja active Active
- 2014-06-20 KR KR1020167001273A patent/KR20160040522A/ko not_active Ceased
- 2014-06-20 IL IL267331A patent/IL267331B2/en unknown
- 2014-06-20 KR KR1020217030964A patent/KR102430126B1/ko active Active
- 2014-06-20 CN CN201910526464.9A patent/CN110498800A/zh active Pending
- 2014-06-20 MX MX2015017972A patent/MX2015017972A/es active IP Right Grant
- 2014-06-20 WO PCT/US2014/043422 patent/WO2014205354A2/en not_active Ceased
-
2015
- 2015-12-21 IL IL243269A patent/IL243269B/en active IP Right Grant
- 2015-12-21 MX MX2020001628A patent/MX2020001628A/es unknown
-
2019
- 2019-06-04 JP JP2019104412A patent/JP2019189618A/ja active Pending
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