JP2014506602A5 - - Google Patents
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- Publication number
- JP2014506602A5 JP2014506602A5 JP2013555597A JP2013555597A JP2014506602A5 JP 2014506602 A5 JP2014506602 A5 JP 2014506602A5 JP 2013555597 A JP2013555597 A JP 2013555597A JP 2013555597 A JP2013555597 A JP 2013555597A JP 2014506602 A5 JP2014506602 A5 JP 2014506602A5
- Authority
- JP
- Japan
- Prior art keywords
- pain
- crystalline form
- pentalene
- diaza
- tetrahydro
- 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
- 238000000034 method Methods 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 46
- 208000002193 Pain Diseases 0.000 claims description 37
- YZGJIENQZBJQNS-UHFFFAOYSA-N pentalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C21 YZGJIENQZBJQNS-UHFFFAOYSA-N 0.000 claims description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- 239000013078 crystal Substances 0.000 claims description 17
- 238000002425 crystallisation Methods 0.000 claims description 17
- 230000008025 crystallization Effects 0.000 claims description 17
- 239000012453 solvate Substances 0.000 claims description 17
- 239000003937 drug carrier Substances 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 10
- KMEFNKVVLAMWRW-CQSZACIVSA-N N-[(2S)-1-hydroxy-3,3-dimethylbutan-2-yl]tricyclo[4.3.0.02,4]nona-1,4,6,8-tetraene-7-carboxamide Chemical compound OC[C@H](C(C)(C)C)NC(=O)C1=C2C=C3C(=C2C=C1)C3 KMEFNKVVLAMWRW-CQSZACIVSA-N 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- ACSQLTBPYZSGBA-GMXVVIOVSA-N olorinab Chemical compound C([C@@H]1C[C@@H]1C=12)C=1C(C(=O)N[C@H](CO)C(C)(C)C)=NN2C1=C[N+]([O-])=CC=N1 ACSQLTBPYZSGBA-GMXVVIOVSA-N 0.000 claims description 8
- -1 1-hydroxymethyl-2,2-dimethyl-propyl Chemical group 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 7
- 239000002552 dosage form Substances 0.000 claims description 7
- 238000002955 isolation Methods 0.000 claims description 7
- 201000001119 neuropathy Diseases 0.000 claims description 7
- 230000007823 neuropathy Effects 0.000 claims description 7
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 7
- 208000006820 Arthralgia Diseases 0.000 claims description 6
- 206010006002 Bone pain Diseases 0.000 claims description 6
- 206010058019 Cancer Pain Diseases 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 208000001640 Fibromyalgia Diseases 0.000 claims description 6
- 206010020751 Hypersensitivity Diseases 0.000 claims description 6
- 206010065390 Inflammatory pain Diseases 0.000 claims description 6
- 208000019695 Migraine disease Diseases 0.000 claims description 6
- 208000000112 Myalgia Diseases 0.000 claims description 6
- 208000001132 Osteoporosis Diseases 0.000 claims description 6
- 208000008765 Sciatica Diseases 0.000 claims description 6
- 206010039710 Scleroderma Diseases 0.000 claims description 6
- 208000030961 allergic reaction Diseases 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 206010027599 migraine Diseases 0.000 claims description 6
- 201000006417 multiple sclerosis Diseases 0.000 claims description 6
- 208000013465 muscle pain Diseases 0.000 claims description 6
- 208000004296 neuralgia Diseases 0.000 claims description 6
- 208000021722 neuropathic pain Diseases 0.000 claims description 6
- 201000008482 osteoarthritis Diseases 0.000 claims description 6
- 206010043778 thyroiditis Diseases 0.000 claims description 6
- 206010019233 Headaches Diseases 0.000 claims description 5
- ZRHDMEYVNHQLEF-SNVBAGLBSA-N OC[C@H](C(C)(C)C)NC(=O)C1=C2C=C3C(=C2N=C1)N3 Chemical compound OC[C@H](C(C)(C)C)NC(=O)C1=C2C=C3C(=C2N=C1)N3 ZRHDMEYVNHQLEF-SNVBAGLBSA-N 0.000 claims description 5
- 230000001363 autoimmune Effects 0.000 claims description 5
- 231100000869 headache Toxicity 0.000 claims description 5
- 208000004371 toothache Diseases 0.000 claims description 5
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 4
- 230000002411 adverse Effects 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 238000002411 thermogravimetry Methods 0.000 claims description 4
- 238000001757 thermogravimetry curve Methods 0.000 claims description 4
- 230000004580 weight loss Effects 0.000 claims description 4
- 238000013213 extrapolation Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 206010065673 Nephritic syndrome Diseases 0.000 claims 3
- VZZHIZMWAZGNAU-SFVIPPHHSA-N N-[(2S)-1-hydroxy-3,3-dimethylbutan-2-yl]-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxamide Chemical compound OC[C@H](C(C)(C)C)NC(=O)C=1C=2CC3C(C=2NN=1)C3 VZZHIZMWAZGNAU-SFVIPPHHSA-N 0.000 claims 1
- 230000002939 deleterious effect Effects 0.000 claims 1
- 230000001747 exhibiting effect Effects 0.000 claims 1
- 238000007614 solvation Methods 0.000 claims 1
- YNZYKPIVVIWDGU-CYBMUJFWSA-N N-[(2S)-1-hydroxy-3,3-dimethylbutan-2-yl]pentalene-1-carboxamide Chemical compound OC[C@H](C(C)(C)C)NC(=O)C=1C2=CC=CC2=CC1 YNZYKPIVVIWDGU-CYBMUJFWSA-N 0.000 description 3
- 201000008383 nephritis Diseases 0.000 description 3
- GUVXZFRDPCKWEM-UHFFFAOYSA-N pentalene Chemical compound C1=CC2=CC=CC2=C1 GUVXZFRDPCKWEM-UHFFFAOYSA-N 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
- 238000001035 drying Methods 0.000 description 2
- 230000005784 autoimmunity Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161446732P | 2011-02-25 | 2011-02-25 | |
| US61/446,732 | 2011-02-25 | ||
| US201161448542P | 2011-03-02 | 2011-03-02 | |
| US61/448,542 | 2011-03-02 | ||
| PCT/US2012/026506 WO2012116276A1 (en) | 2011-02-25 | 2012-02-24 | Crystalline forms and processes for the preparation of condensed azacycles ( cannabinoid receptor modulators) |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014506602A JP2014506602A (ja) | 2014-03-17 |
| JP2014506602A5 true JP2014506602A5 (OSRAM) | 2015-04-16 |
| JP5945554B2 JP5945554B2 (ja) | 2016-07-05 |
Family
ID=45841624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013555597A Active JP5945554B2 (ja) | 2011-02-25 | 2012-02-24 | 縮合型アザ環の結晶形およびその調製プロセス（カンナビノイド受容体モジュレーター） |
Country Status (20)
| Country | Link |
|---|---|
| US (4) | US9458136B2 (OSRAM) |
| EP (3) | EP3395812B8 (OSRAM) |
| JP (1) | JP5945554B2 (OSRAM) |
| KR (1) | KR102036932B1 (OSRAM) |
| CN (1) | CN103608343B (OSRAM) |
| AU (1) | AU2012222146B2 (OSRAM) |
| BR (1) | BR112013021549B1 (OSRAM) |
| CA (1) | CA2827057C (OSRAM) |
| CL (1) | CL2013002436A1 (OSRAM) |
| CO (1) | CO6852066A2 (OSRAM) |
| DK (1) | DK3395812T3 (OSRAM) |
| EA (1) | EA035989B1 (OSRAM) |
| ES (1) | ES2932441T3 (OSRAM) |
| IL (1) | IL227782A (OSRAM) |
| MX (1) | MX346533B (OSRAM) |
| MY (1) | MY165767A (OSRAM) |
| PH (1) | PH12013501726A1 (OSRAM) |
| SG (1) | SG192817A1 (OSRAM) |
| WO (1) | WO2012116276A1 (OSRAM) |
| ZA (1) | ZA201306402B (OSRAM) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200008045A (ko) | 2009-08-28 | 2020-01-22 | 아레나 파마슈티칼스, 인크. | 칸나비노이드 수용체 조절제 |
| US9597340B2 (en) | 2011-02-25 | 2017-03-21 | Arena Pharmaceuticals, Inc. | Cannabinoid receptor modulators |
| MX346533B (es) * | 2011-02-25 | 2017-03-14 | Arena Pharm Inc | Formas cristalinas y procesos para la preparacion de azaciclos condensados (moduladores de receptores canabinoides). |
| JP6043733B2 (ja) | 2011-02-25 | 2016-12-14 | アリーナ ファーマシューティカルズ， インコーポレイテッド | カンナビノイド受容体モジュレーター |
| WO2016085941A1 (en) * | 2014-11-25 | 2016-06-02 | Arena Pharmaceuticals, Inc. | Processes for the preparation of cannabinoid receptor modulators |
| CN109310673A (zh) * | 2016-04-10 | 2019-02-05 | 艾尼纳制药公司 | 用选择性cb2受体激动剂治疗的方法 |
| WO2018208847A1 (en) | 2017-05-08 | 2018-11-15 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of pain from inflammatory bowel disease |
| EP3621619B1 (en) * | 2017-05-08 | 2023-06-28 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of visceral pain |
| WO2021047581A1 (zh) * | 2019-09-12 | 2021-03-18 | 四川海思科制药有限公司 | 一种六氢化苯并吡唑衍生物及其制备 |
| TW202330496A (zh) | 2021-10-05 | 2023-08-01 | 美商艾尼納製藥公司 | 用於製備大麻素受體調節劑之結晶形式及方法 |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3964478B2 (ja) | 1995-06-30 | 2007-08-22 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ヘテロ環含有カルボン酸誘導体及びそれを含有する医薬 |
| ATE368037T1 (de) | 1999-04-28 | 2007-08-15 | Sanofi Aventis Deutschland | Di-aryl-säurederivate als ppar rezeptor liganden |
| EP1461027A4 (en) | 2001-12-07 | 2005-09-07 | Univ Virginia Commonwealth | TREATMENT OF NEOPLASIA |
| SE0300010D0 (sv) | 2003-01-07 | 2003-01-07 | Astrazeneca Ab | Novel Compounds |
| WO2005123677A1 (en) | 2004-06-16 | 2005-12-29 | Actelion Pharmaceuticals Ltd | 4-carbonyl substituted 1,1,2-trimethyl-1a,4,5,5a-tetrahydro-1h-4-aza-cyclopropa'a!pentalene derivatives as agonists for the g-protein-coupled receptor s1p1/edg1 and immunosuppressive agents |
| NZ580387A (en) | 2004-07-12 | 2011-06-30 | Cadila Healthcare Ltd | Tricyclic pyrazole derivatives as cannabinoid receptor modulators |
| FR2875230A1 (fr) | 2004-09-13 | 2006-03-17 | Sanofi Aventis Sa | Derives de pyrazole condense, leur preparation et leur application en therapeutique |
| DE102004054666A1 (de) | 2004-11-12 | 2006-05-18 | Bayer Cropscience Gmbh | Substituierte Pyrazol-3-carboxamide, Verfahren zur Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| PE20060949A1 (es) | 2004-12-23 | 2006-10-11 | Arena Pharm Inc | Derivados fusionados de pirazol como agonistas del receptor de niacina |
| CN101238107A (zh) * | 2005-06-02 | 2008-08-06 | 格兰马克药品股份有限公司 | 新的大麻素受体配体，含有该配体的药物组合物及其制备方法 |
| PL1902034T3 (pl) * | 2005-06-02 | 2011-09-30 | Glenmark Pharmaceuticals Sa | Nowe ligandy receptorów kanabinoidowych, kompozycja farmaceutyczna je zawierająca oraz proces ich wytwarzania |
| ATE459352T1 (de) | 2006-07-04 | 2010-03-15 | Janssen Pharmaceutica Nv | Benzimidazol-cannabinoid-agonisten mit einer substituierten heterocyclischen gruppe |
| US7928123B2 (en) | 2006-09-25 | 2011-04-19 | Boehringer Ingelheim International Gmbh | Compounds which modulate the CB2 receptor |
| WO2008063781A2 (en) | 2006-10-12 | 2008-05-29 | Abbott Laboratories | Chemical compounds as cannabinoid receptor ligands |
| US7928103B2 (en) | 2006-10-17 | 2011-04-19 | Boehringer Ingelheim International Gmbh | Compounds which modulate the CB2 receptor |
| RU2009117203A (ru) | 2006-11-03 | 2010-12-10 | Гленмарк Фармасеутикалс С.А. (Ch) | Новые лиганды каннабиноидных рецепторов, фармацевтические композиции, содержащие данные лиганды, и способы их получения |
| WO2008064054A2 (en) | 2006-11-21 | 2008-05-29 | Boehringer Ingelheim International Gmbh | Compounds which modulate the cb2 receptor |
| EP2120938A4 (en) | 2006-12-20 | 2010-12-08 | Merck Sharp & Dohme | IMIDAZOPYRIDINE ANALOGUE AS CB2 RECEPTOR MODULATORS FOR THE TREATMENT OF PAIN, RESPIRATORY AND NON-RESPIRATORY DISEASES |
| WO2008079316A1 (en) | 2006-12-20 | 2008-07-03 | Cara Therapeutics, Inc. | Tetrahydroquinolinones, tetrahydronaphthyridones and derivatives thereof |
| WO2008109007A1 (en) | 2007-03-02 | 2008-09-12 | Cara Therapeutics, Inc. | Bridged phenanthridines |
| WO2008114619A1 (ja) | 2007-03-16 | 2008-09-25 | Kyocera Corporation | 誘電体磁器およびコンデンサ |
| WO2008119694A1 (en) | 2007-03-30 | 2008-10-09 | Janssen Pharmaceutica Nv | Benzimidazole cannabinoid agonists |
| US20090209536A1 (en) | 2007-06-17 | 2009-08-20 | Kalypsys, Inc. | Aminoquinazoline cannabinoid receptor modulators for treatment of disease |
| EP2170350B1 (en) | 2007-06-21 | 2013-09-11 | Cara Therapeutics, Inc. | Substituted imidazoheterocycles |
| US8338623B2 (en) | 2007-07-09 | 2012-12-25 | Abbvie Inc. | Compounds as cannabinoid receptor ligands |
| US7943658B2 (en) | 2007-07-23 | 2011-05-17 | Bristol-Myers Squibb Company | Indole indane amide compounds useful as CB2 agonists and method |
| EP2203171A2 (en) | 2007-08-21 | 2010-07-07 | Merck Sharp & Dohme Corp. | Cb2 receptor ligands for the treatment of pain |
| UA104010C2 (en) | 2008-12-18 | 2013-12-25 | Эли Лилли Энд Компани | Purine compounds |
| US7741350B1 (en) | 2009-01-28 | 2010-06-22 | Cara Therapeutics, Inc. | Bicyclic pyrazolo-heterocycles |
| CA2749884C (en) | 2009-01-28 | 2018-01-23 | Cara Therapeutics, Inc. | Bicyclic pyrazolo-heterocycles |
| KR20200008045A (ko) * | 2009-08-28 | 2020-01-22 | 아레나 파마슈티칼스, 인크. | 칸나비노이드 수용체 조절제 |
| MX346533B (es) | 2011-02-25 | 2017-03-14 | Arena Pharm Inc | Formas cristalinas y procesos para la preparacion de azaciclos condensados (moduladores de receptores canabinoides). |
| WO2012116278A1 (en) | 2011-02-25 | 2012-08-30 | Arena Pharmaceuticals, Inc. | Cannabinoid receptor modulators |
| US9597340B2 (en) | 2011-02-25 | 2017-03-21 | Arena Pharmaceuticals, Inc. | Cannabinoid receptor modulators |
| JP6043733B2 (ja) | 2011-02-25 | 2016-12-14 | アリーナ ファーマシューティカルズ， インコーポレイテッド | カンナビノイド受容体モジュレーター |
-
2012
- 2012-02-24 MX MX2013009760A patent/MX346533B/es active IP Right Grant
- 2012-02-24 PH PH1/2013/501726A patent/PH12013501726A1/en unknown
- 2012-02-24 EP EP18164225.7A patent/EP3395812B8/en active Active
- 2012-02-24 WO PCT/US2012/026506 patent/WO2012116276A1/en not_active Ceased
- 2012-02-24 EP EP22197435.5A patent/EP4166552B1/en active Active
- 2012-02-24 EP EP12709201.3A patent/EP2678330A1/en not_active Withdrawn
- 2012-02-24 JP JP2013555597A patent/JP5945554B2/ja active Active
- 2012-02-24 AU AU2012222146A patent/AU2012222146B2/en not_active Ceased
- 2012-02-24 KR KR1020137025057A patent/KR102036932B1/ko not_active Expired - Fee Related
- 2012-02-24 DK DK18164225.7T patent/DK3395812T3/da active
- 2012-02-24 EA EA201391233A patent/EA035989B1/ru not_active IP Right Cessation
- 2012-02-24 BR BR112013021549-6A patent/BR112013021549B1/pt not_active IP Right Cessation
- 2012-02-24 US US14/001,133 patent/US9458136B2/en active Active
- 2012-02-24 MY MYPI2013003122A patent/MY165767A/en unknown
- 2012-02-24 CA CA2827057A patent/CA2827057C/en active Active
- 2012-02-24 ES ES18164225T patent/ES2932441T3/es active Active
- 2012-02-24 CN CN201280020512.3A patent/CN103608343B/zh not_active Expired - Fee Related
- 2012-02-24 SG SG2013062427A patent/SG192817A1/en unknown
-
2013
- 2013-08-04 IL IL227782A patent/IL227782A/en active IP Right Grant
- 2013-08-23 ZA ZA2013/06402A patent/ZA201306402B/en unknown
- 2013-08-23 CL CL2013002436A patent/CL2013002436A1/es unknown
- 2013-09-10 CO CO13214674A patent/CO6852066A2/es active IP Right Grant
-
2016
- 2016-08-26 US US15/248,300 patent/US10183930B2/en active Active
-
2018
- 2018-12-10 US US16/214,388 patent/US10981895B2/en active Active
-
2021
- 2021-03-16 US US17/202,946 patent/US11560369B2/en active Active
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