JPWO2019204446A5 - - Google Patents
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- JPWO2019204446A5 JPWO2019204446A5 JP2021506619A JP2021506619A JPWO2019204446A5 JP WO2019204446 A5 JPWO2019204446 A5 JP WO2019204446A5 JP 2021506619 A JP2021506619 A JP 2021506619A JP 2021506619 A JP2021506619 A JP 2021506619A JP WO2019204446 A5 JPWO2019204446 A5 JP WO2019204446A5
- Authority
- JP
- Japan
- Prior art keywords
- crystal
- measured
- parameters listed
- xrpd pattern
- crystalline salt
- 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.)
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- 239000013078 crystal Substances 0.000 claims description 113
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 95
- 150000003839 salts Chemical class 0.000 claims description 81
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 28
- 238000001938 differential scanning calorimetry curve Methods 0.000 claims description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
- 208000003251 Pruritus Diseases 0.000 claims description 18
- 206010015037 epilepsy Diseases 0.000 claims description 18
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 18
- 208000002193 Pain Diseases 0.000 claims description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 14
- 208000035475 disorder Diseases 0.000 claims description 14
- 208000011580 syndromic disease Diseases 0.000 claims description 14
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 12
- 238000001757 thermogravimetry curve Methods 0.000 claims description 11
- 206010003805 Autism Diseases 0.000 claims description 9
- 208000020706 Autistic disease Diseases 0.000 claims description 9
- 206010061334 Partial seizures Diseases 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical compound N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 claims description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 7
- 230000007803 itching Effects 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- -1 biphenyl-2-carbo Nitrile phosphate Chemical compound 0.000 claims description 6
- 201000007186 focal epilepsy Diseases 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 201000001119 neuropathy Diseases 0.000 claims description 5
- 230000007823 neuropathy Effects 0.000 claims description 5
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 208000003078 Generalized Epilepsy Diseases 0.000 claims description 4
- 206010071082 Juvenile myoclonic epilepsy Diseases 0.000 claims description 4
- 208000005392 Spasm Diseases 0.000 claims description 4
- 201000001993 idiopathic generalized epilepsy Diseases 0.000 claims description 4
- 208000034287 idiopathic generalized susceptibility to 7 epilepsy Diseases 0.000 claims description 4
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 4
- 229940011051 isopropyl acetate Drugs 0.000 claims description 4
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 201000009053 Neurodermatitis Diseases 0.000 claims description 3
- 230000003211 malignant effect Effects 0.000 claims description 3
- 230000001617 migratory effect Effects 0.000 claims description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 2
- 208000007848 Alcoholism Diseases 0.000 claims description 2
- 208000019901 Anxiety disease Diseases 0.000 claims description 2
- 208000014644 Brain disease Diseases 0.000 claims description 2
- 208000028698 Cognitive impairment Diseases 0.000 claims description 2
- 206010010904 Convulsion Diseases 0.000 claims description 2
- 206010070666 Cortical dysplasia Diseases 0.000 claims description 2
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 2
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 2
- 241000004297 Draba Species 0.000 claims description 2
- 208000032274 Encephalopathy Diseases 0.000 claims description 2
- 208000001640 Fibromyalgia Diseases 0.000 claims description 2
- 208000001914 Fragile X syndrome Diseases 0.000 claims description 2
- 102000027484 GABAA receptors Human genes 0.000 claims description 2
- 108091008681 GABAA receptors Proteins 0.000 claims description 2
- 208000011688 Generalised anxiety disease Diseases 0.000 claims description 2
- 241000208818 Helianthus Species 0.000 claims description 2
- 235000003222 Helianthus annuus Nutrition 0.000 claims description 2
- 208000007514 Herpes zoster Diseases 0.000 claims description 2
- 208000017605 Hodgkin disease nodular sclerosis Diseases 0.000 claims description 2
- 206010021750 Infantile Spasms Diseases 0.000 claims description 2
- 208000035899 Infantile spasms syndrome Diseases 0.000 claims description 2
- 206010065390 Inflammatory pain Diseases 0.000 claims description 2
- 102000004310 Ion Channels Human genes 0.000 claims description 2
- 208000000676 Malformations of Cortical Development Diseases 0.000 claims description 2
- 208000007101 Muscle Cramp Diseases 0.000 claims description 2
- 206010028391 Musculoskeletal Pain Diseases 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- 208000037158 Partial Epilepsies Diseases 0.000 claims description 2
- 208000004983 Phantom Limb Diseases 0.000 claims description 2
- 206010056238 Phantom pain Diseases 0.000 claims description 2
- 208000004550 Postoperative Pain Diseases 0.000 claims description 2
- 206010037660 Pyrexia Diseases 0.000 claims description 2
- 206010071141 Rasmussen encephalitis Diseases 0.000 claims description 2
- 208000004160 Rasmussen subacute encephalitis Diseases 0.000 claims description 2
- 206010042496 Sunburn Diseases 0.000 claims description 2
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 2
- 206010044565 Tremor Diseases 0.000 claims description 2
- 201000006791 West syndrome Diseases 0.000 claims description 2
- 238000009825 accumulation Methods 0.000 claims description 2
- 201000007930 alcohol dependence Diseases 0.000 claims description 2
- 208000029650 alcohol withdrawal Diseases 0.000 claims description 2
- 230000036506 anxiety Effects 0.000 claims description 2
- 201000008937 atopic dermatitis Diseases 0.000 claims description 2
- 208000023397 cerebral cortical dysplasia Diseases 0.000 claims description 2
- 238000002512 chemotherapy Methods 0.000 claims description 2
- 230000001684 chronic effect Effects 0.000 claims description 2
- 208000010877 cognitive disease Diseases 0.000 claims description 2
- 208000013500 continuous spikes and waves during sleep Diseases 0.000 claims description 2
- 206010013663 drug dependence Diseases 0.000 claims description 2
- 230000004064 dysfunction Effects 0.000 claims description 2
- 206010014599 encephalitis Diseases 0.000 claims description 2
- 208000029364 generalized anxiety disease Diseases 0.000 claims description 2
- 230000000366 juvenile effect Effects 0.000 claims description 2
- 230000035772 mutation Effects 0.000 claims description 2
- 230000001272 neurogenic effect Effects 0.000 claims description 2
- 201000008482 osteoarthritis Diseases 0.000 claims description 2
- 208000019906 panic disease Diseases 0.000 claims description 2
- 230000002093 peripheral effect Effects 0.000 claims description 2
- 230000000069 prophylactic effect Effects 0.000 claims description 2
- 230000001107 psychogenic effect Effects 0.000 claims description 2
- 201000000980 schizophrenia Diseases 0.000 claims description 2
- 208000011117 substance-related disease Diseases 0.000 claims description 2
- 230000002123 temporal effect Effects 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 230000009529 traumatic brain injury Effects 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims 6
- 230000008018 melting Effects 0.000 claims 6
- 238000004807 desolvation Methods 0.000 claims 5
- 229910019142 PO4 Inorganic materials 0.000 claims 3
- 150000002825 nitriles Chemical class 0.000 claims 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 3
- 239000010452 phosphate Substances 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- 208000008035 Back Pain Diseases 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 208000019804 backache Diseases 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000010287 polarization Effects 0.000 claims 1
- 208000017940 prurigo nodularis Diseases 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 230000002485 urinary effect Effects 0.000 claims 1
- 206010037083 Prurigo Diseases 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 201000008009 Early infantile epileptic encephalopathy Diseases 0.000 description 1
- 208000002091 Febrile Seizures Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 208000013257 developmental and epileptic encephalopathy Diseases 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2024030150A JP7721712B2 (ja) | 2018-04-18 | 2024-02-29 | Ｇａｂａａ陽性アロステリックモジュレーター化合物、その作製の方法および使用 |
| JP2025127411A JP2025166011A (ja) | 2018-04-18 | 2025-07-30 | Ｇａｂａａ陽性アロステリックモジュレーター化合物、その作製の方法および使用 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862659226P | 2018-04-18 | 2018-04-18 | |
| US62/659,226 | 2018-04-18 | ||
| PCT/US2019/027880 WO2019204446A1 (en) | 2018-04-18 | 2019-04-17 | Gabaa positive allosteric modulator compounds, methods of making, and uses thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024030150A Division JP7721712B2 (ja) | 2018-04-18 | 2024-02-29 | Ｇａｂａａ陽性アロステリックモジュレーター化合物、その作製の方法および使用 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2021522330A JP2021522330A (ja) | 2021-08-30 |
| JPWO2019204446A5 true JPWO2019204446A5 (https=) | 2022-04-25 |
| JP2021522330A5 JP2021522330A5 (https=) | 2022-04-25 |
| JP7449272B2 JP7449272B2 (ja) | 2024-03-13 |
Family
ID=68239798
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021506619A Active JP7449272B2 (ja) | 2018-04-18 | 2019-04-17 | Ｇａｂａａ陽性アロステリックモジュレーター化合物、その作製の方法および使用 |
| JP2024030150A Active JP7721712B2 (ja) | 2018-04-18 | 2024-02-29 | Ｇａｂａａ陽性アロステリックモジュレーター化合物、その作製の方法および使用 |
| JP2025127411A Pending JP2025166011A (ja) | 2018-04-18 | 2025-07-30 | Ｇａｂａａ陽性アロステリックモジュレーター化合物、その作製の方法および使用 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024030150A Active JP7721712B2 (ja) | 2018-04-18 | 2024-02-29 | Ｇａｂａａ陽性アロステリックモジュレーター化合物、その作製の方法および使用 |
| JP2025127411A Pending JP2025166011A (ja) | 2018-04-18 | 2025-07-30 | Ｇａｂａａ陽性アロステリックモジュレーター化合物、その作製の方法および使用 |
Country Status (14)
| Country | Link |
|---|---|
| US (3) | US11542263B2 (https=) |
| EP (1) | EP3781566A4 (https=) |
| JP (3) | JP7449272B2 (https=) |
| KR (2) | KR102799156B1 (https=) |
| CN (2) | CN112384513A (https=) |
| AU (2) | AU2019255282B2 (https=) |
| BR (1) | BR112020021104A2 (https=) |
| CA (1) | CA3096890A1 (https=) |
| CL (1) | CL2020002663A1 (https=) |
| IL (1) | IL278067A (https=) |
| MX (2) | MX2020010878A (https=) |
| SG (1) | SG11202010220QA (https=) |
| TW (1) | TW202012402A (https=) |
| WO (1) | WO2019204446A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7449272B2 (ja) * | 2018-04-18 | 2024-03-13 | ニューロサイクル・セラピューティクス・インコーポレイテッド | Ｇａｂａａ陽性アロステリックモジュレーター化合物、その作製の方法および使用 |
| SG11202109526PA (en) * | 2019-03-18 | 2021-10-28 | Neurocycle Therapeutics Inc | Use of gabaa receptor modulators for treatment of pain |
| JP2022553718A (ja) * | 2019-10-22 | 2022-12-26 | ニューロサイクル・セラピューティクス・インコーポレイテッド | Ｇａｂａａ陽性アロステリック調節因子化合物、作成方法、およびその使用 |
| KR20220087507A (ko) * | 2019-10-23 | 2022-06-24 | 뉴로사이클 테라퓨틱스, 인크. | Gabaa 수용체 조절제를 사용한 간질 병태의 치료 |
| US12233070B2 (en) * | 2020-06-30 | 2025-02-25 | University Of Mississippi Medical Center | Methods for treating benzodiazepine misuse/use disorder |
| AU2023356939A1 (en) * | 2022-10-04 | 2025-04-10 | Engrail Therapeutics, Inc. | Gaba a receptor modulators and uses thereof |
| WO2025175214A1 (en) * | 2024-02-16 | 2025-08-21 | Engrail Therapeutics, Inc. | Methods of treating generalized anxiety disorder |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2802343C2 (de) | 1978-01-20 | 1982-04-22 | Peter Prof. Dr.-Ing. Friderichs | Latentwärmespeicher-Behälter |
| GB9813576D0 (en) * | 1998-06-24 | 1998-08-19 | Merck Sharp & Dohme | Therapeutic agents |
| CA2427779A1 (en) * | 2000-11-10 | 2002-05-16 | Merck Sharp & Dohme Limited | Imidazo-triazine derivatives as ligands for gaba receptors |
| GB0117277D0 (en) | 2001-07-16 | 2001-09-05 | Merck Sharp & Dohme | Therapeutic agents |
| TWI248936B (en) | 2001-03-21 | 2006-02-11 | Merck Sharp & Dohme | Imidazo-pyrimidine derivatives as ligands for GABA receptors |
| JP2004170323A (ja) | 2002-11-22 | 2004-06-17 | Sumitomo Pharmaceut Co Ltd | 皮膚疾患治療剤のスクリーニング方法 |
| WO2009021957A2 (en) | 2007-08-14 | 2009-02-19 | Novartis Ag | Tricyclic heterocyclic compounds as gaba a modulators |
| WO2009143211A2 (en) | 2008-05-21 | 2009-11-26 | Incyte Corporation | Salts of 2-fluoro-n-methyl-4-[7-(quinolin-6-yl-methyl)- imidazo[1,2-b][1,2,4]triazin-2-yl]benzamide and processes related to preparing the same |
| US20110082147A1 (en) | 2009-07-24 | 2011-04-07 | Concert Pharmaceuticals, Inc. | Substituted imidazotriazines |
| MX362181B (es) | 2013-02-19 | 2019-01-08 | Ono Pharmaceutical Co | Compuesto inhibidor de cinasa del receptor de tropomiosina (trk). |
| WO2015072853A1 (en) | 2013-11-13 | 2015-05-21 | Rjg Developments B.V. | Treatment of herpes virus infection outbreaks |
| SG11201806393QA (en) * | 2016-01-27 | 2018-08-30 | Univ Zuerich | Use of gabaa receptor modulators for treatment of itch |
| JP7449272B2 (ja) * | 2018-04-18 | 2024-03-13 | ニューロサイクル・セラピューティクス・インコーポレイテッド | Ｇａｂａａ陽性アロステリックモジュレーター化合物、その作製の方法および使用 |
-
2019
- 2019-04-17 JP JP2021506619A patent/JP7449272B2/ja active Active
- 2019-04-17 TW TW108113441A patent/TW202012402A/zh unknown
- 2019-04-17 CN CN201980041321.7A patent/CN112384513A/zh active Pending
- 2019-04-17 KR KR1020207033073A patent/KR102799156B1/ko active Active
- 2019-04-17 BR BR112020021104-4A patent/BR112020021104A2/pt unknown
- 2019-04-17 WO PCT/US2019/027880 patent/WO2019204446A1/en not_active Ceased
- 2019-04-17 MX MX2020010878A patent/MX2020010878A/es unknown
- 2019-04-17 CA CA3096890A patent/CA3096890A1/en active Pending
- 2019-04-17 KR KR1020257012376A patent/KR20250057112A/ko active Pending
- 2019-04-17 EP EP19788410.9A patent/EP3781566A4/en active Pending
- 2019-04-17 SG SG11202010220QA patent/SG11202010220QA/en unknown
- 2019-04-17 AU AU2019255282A patent/AU2019255282B2/en active Active
- 2019-04-17 CN CN202511219750.2A patent/CN121135719A/zh active Pending
-
2020
- 2020-10-14 MX MX2024004400A patent/MX2024004400A/es unknown
- 2020-10-15 IL IL278067A patent/IL278067A/en unknown
- 2020-10-15 CL CL2020002663A patent/CL2020002663A1/es unknown
- 2020-10-16 US US17/072,282 patent/US11542263B2/en active Active
-
2022
- 2022-12-28 US US18/089,661 patent/US12134619B2/en active Active
-
2024
- 2024-02-29 JP JP2024030150A patent/JP7721712B2/ja active Active
- 2024-10-02 US US18/904,228 patent/US20250034155A1/en active Pending
- 2024-11-07 AU AU2024259803A patent/AU2024259803A1/en active Pending
-
2025
- 2025-07-30 JP JP2025127411A patent/JP2025166011A/ja active Pending
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