JP2018501299A5 - - Google Patents
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- JP2018501299A5 JP2018501299A5 JP2017543308A JP2017543308A JP2018501299A5 JP 2018501299 A5 JP2018501299 A5 JP 2018501299A5 JP 2017543308 A JP2017543308 A JP 2017543308A JP 2017543308 A JP2017543308 A JP 2017543308A JP 2018501299 A5 JP2018501299 A5 JP 2018501299A5
- Authority
- JP
- Japan
- Prior art keywords
- pharmaceutically acceptable
- deuterium
- compound
- acceptable salt
- pharmaceutical composition
- 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
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- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 188
- 229910052805 deuterium Inorganic materials 0.000 claims description 187
- 150000001875 compounds Chemical class 0.000 claims description 186
- 239000008194 pharmaceutical composition Substances 0.000 claims description 153
- 150000003839 salts Chemical class 0.000 claims description 142
- BEQZHFIKTBVCAU-UHFFFAOYSA-N 2-amino-2-(2-chlorophenyl)-1-cyclohexanone Chemical compound C=1C=CC=C(Cl)C=1C1(N)CCCCC1=O BEQZHFIKTBVCAU-UHFFFAOYSA-N 0.000 claims description 105
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 53
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 claims description 52
- 229960003299 ketamine Drugs 0.000 claims description 52
- 208000002193 Pain Diseases 0.000 claims description 43
- 230000002401 inhibitory effect Effects 0.000 claims description 40
- 230000001508 neuroinhibitory effect Effects 0.000 claims description 40
- 239000003814 drug Substances 0.000 claims description 38
- 229940079593 drug Drugs 0.000 claims description 37
- 201000010099 disease Diseases 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- 210000005036 nerve Anatomy 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- 239000007916 tablet composition Substances 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 24
- 208000035475 disorder Diseases 0.000 claims description 21
- 238000013270 controlled release Methods 0.000 claims description 19
- 208000024891 symptom Diseases 0.000 claims description 17
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 8
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- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical group OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 5
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims description 5
- 208000009205 Tinnitus Diseases 0.000 claims description 5
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- 0 *C(C(*)(*)C(*)=C(*)C1=O)C1(c(c(*)c(*)c(*)c1*)c1Cl)N(*)* Chemical compound *C(C(*)(*)C(*)=C(*)C1=O)C1(c(c(*)c(*)c(*)c1*)c1Cl)N(*)* 0.000 description 14
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- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 3
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- 206010003246 arthritis Diseases 0.000 description 3
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- 208000028683 bipolar I disease Diseases 0.000 description 3
- 208000025307 bipolar depression Diseases 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 206010015037 epilepsy Diseases 0.000 description 3
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 3
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 3
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 3
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 3
- 208000024714 major depressive disease Diseases 0.000 description 3
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- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
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- 239000007897 gelcap Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000006197 inhalational dosage form Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000008203 oral pharmaceutical composition Substances 0.000 description 2
- 239000006201 parenteral dosage form Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 1
- LNSMPSPTFDIWRQ-GSVOUGTGSA-N (2r)-4-amino-2-(methylamino)-4-oxobutanoic acid Chemical compound CN[C@@H](C(O)=O)CC(N)=O LNSMPSPTFDIWRQ-GSVOUGTGSA-N 0.000 description 1
- BEQZHFIKTBVCAU-LBPRGKRZSA-N (2s)-2-amino-2-(2-chlorophenyl)cyclohexan-1-one Chemical compound C=1C=CC=C(Cl)C=1[C@@]1(N)CCCCC1=O BEQZHFIKTBVCAU-LBPRGKRZSA-N 0.000 description 1
- YQEZLKZALYSWHR-ZDUSSCGKSA-N (S)-ketamine Chemical compound C=1C=CC=C(Cl)C=1[C@@]1(NC)CCCCC1=O YQEZLKZALYSWHR-ZDUSSCGKSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- 208000011688 Generalised anxiety disease Diseases 0.000 description 1
- 229920002907 Guar gum Polymers 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 229920000569 Gum karaya Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229920000161 Locust bean gum Polymers 0.000 description 1
- 208000019022 Mood disease Diseases 0.000 description 1
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 1
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 229920000954 Polyglycolide Polymers 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000934878 Sterculia Species 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
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- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 239000000305 astragalus gummifer gum Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
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- 229920001525 carrageenan Polymers 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 208000029364 generalized anxiety disease Diseases 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 229920002674 hyaluronan Polymers 0.000 description 1
- 229960003160 hyaluronic acid Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
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- 235000010494 karaya gum Nutrition 0.000 description 1
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- 235000010420 locust bean gum Nutrition 0.000 description 1
- 239000000711 locust bean gum Substances 0.000 description 1
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- 229920001277 pectin Polymers 0.000 description 1
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- 235000010987 pectin Nutrition 0.000 description 1
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- 229920000747 poly(lactic acid) Polymers 0.000 description 1
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- 239000010457 zeolite Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021078368A JP2021120389A (ja) | 2014-11-04 | 2021-05-06 | 神経抑制性ケタミンおよびノルケタミン化合物、その誘導体ならびに方法 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462074645P | 2014-11-04 | 2014-11-04 | |
| US62/074,645 | 2014-11-04 | ||
| PCT/US2015/059113 WO2016073653A1 (en) | 2014-11-04 | 2015-11-04 | Neuro-attenuating ketamine and norketamine compounds, derivatives thereof, and methods |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021078368A Division JP2021120389A (ja) | 2014-11-04 | 2021-05-06 | 神経抑制性ケタミンおよびノルケタミン化合物、その誘導体ならびに方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018501299A JP2018501299A (ja) | 2018-01-18 |
| JP2018501299A5 true JP2018501299A5 (https=) | 2018-12-13 |
| JP6882180B2 JP6882180B2 (ja) | 2021-06-02 |
Family
ID=55909773
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017543308A Active JP6882180B2 (ja) | 2014-11-04 | 2015-11-04 | 神経抑制性ケタミンおよびノルケタミン化合物、その誘導体ならびに方法 |
| JP2021078368A Pending JP2021120389A (ja) | 2014-11-04 | 2021-05-06 | 神経抑制性ケタミンおよびノルケタミン化合物、その誘導体ならびに方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021078368A Pending JP2021120389A (ja) | 2014-11-04 | 2021-05-06 | 神経抑制性ケタミンおよびノルケタミン化合物、その誘導体ならびに方法 |
Country Status (18)
| Country | Link |
|---|---|
| US (6) | US10252982B2 (https=) |
| EP (2) | EP4393487A3 (https=) |
| JP (2) | JP6882180B2 (https=) |
| KR (1) | KR102604397B1 (https=) |
| CN (2) | CN115521217A (https=) |
| AU (1) | AU2015343083B2 (https=) |
| CA (1) | CA2966737A1 (https=) |
| DK (1) | DK3215147T3 (https=) |
| ES (1) | ES2977383T3 (https=) |
| FI (1) | FI3215147T3 (https=) |
| HU (1) | HUE066468T2 (https=) |
| LT (1) | LT3215147T (https=) |
| PL (1) | PL3215147T3 (https=) |
| PT (1) | PT3215147T (https=) |
| RS (1) | RS65411B1 (https=) |
| RU (1) | RU2771275C2 (https=) |
| SI (1) | SI3215147T1 (https=) |
| WO (1) | WO2016073653A1 (https=) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUE056378T2 (hu) | 2013-09-13 | 2022-02-28 | Univ Chiba Nat Univ Corp | R-Ketamin és sójának alkalmazása gyógyszerekként |
| US20150118300A1 (en) | 2013-10-31 | 2015-04-30 | Cima Labs Inc. | Immediate Release Abuse-Deterrent Granulated Dosage Forms |
| PL3287124T3 (pl) | 2014-04-17 | 2023-02-20 | Ketabon Gmbh | Doustna postać dawkowania ketaminy |
| DK3215147T3 (da) * | 2014-11-04 | 2024-04-02 | Acadia Pharm Inc | Neurodæmpende norketamin-forbindelser og fremgangsmåder |
| US11426366B2 (en) * | 2015-05-15 | 2022-08-30 | Arizona Board Of Regents On Behalf Of The Universsity Of Arizona | Compositions and methods for treating motor disorders |
| CN107847469A (zh) | 2015-06-27 | 2018-03-27 | 美国神农制药责任有限公司 | 氯胺酮透皮递送系统 |
| EP3442940A1 (en) * | 2016-04-11 | 2019-02-20 | Clexio Biosciences Ltd. | Deuterated ketamine derivatives |
| US20190256487A1 (en) * | 2016-09-16 | 2019-08-22 | BioPharmaWorks, LLC | Hydroxynorketamine prodrugs |
| AU2017351437B2 (en) * | 2016-10-27 | 2022-01-27 | National University Corporation Chiba University | Application of (S)-norketamine and salt thereof as pharmaceutical |
| CA3059775A1 (en) | 2017-04-13 | 2018-10-18 | Ovid Therapeutics Inc. | Methods of treating developmental encephalopathies |
| WO2018234568A2 (en) * | 2017-06-23 | 2018-12-27 | Develco Pharma Schweiz Ag | HYDROXYNORKETAMINE FOR USE IN TREATING DEPRESSION |
| CA3071491A1 (en) | 2017-07-31 | 2019-02-07 | Small Pharma Ltd | Crystalline forms of hydroxynorketamine |
| US12090123B2 (en) | 2017-10-10 | 2024-09-17 | Douglas Pharmaceuticals Ltd. | Extended release pharmaceutical formulation |
| CN111630026A (zh) * | 2017-10-10 | 2020-09-04 | 道格拉斯制药有限公司 | 缓释药物制剂和治疗方法 |
| US11471415B2 (en) | 2017-10-10 | 2022-10-18 | Douglas Pharmaceuticals, Ltd. | Extended release pharmaceutical formulation and methods of treatment |
| US10869838B2 (en) | 2017-10-10 | 2020-12-22 | Douglas Pharmaceuticals, Ltd. | Extended release pharmaceutical formulation |
| US10441544B2 (en) | 2017-10-10 | 2019-10-15 | Douglas Pharmaceuticals, Ltd. | Extended release pharmaceutical formulation |
| WO2022064387A1 (en) * | 2020-09-24 | 2022-03-31 | Douglas Pharmaceuticals Ltd. | Extended release pharmaceutical formulation |
| EP3501503A1 (en) * | 2017-12-22 | 2019-06-26 | Cosmo Technologies Ltd. | Solid delivery composition |
| ES2907692T3 (es) | 2017-12-29 | 2022-04-26 | Celon Pharma Sa | Composición de ketamina de polvo seco para su administración por vía pulmonar en la depresión resistente al tratamiento |
| US11980595B2 (en) | 2018-02-15 | 2024-05-14 | National University Corporation Chiba University | Preventive or therapeutic agent and pharmaceutical composition for inflammatory diseases or bone diseases |
| WO2019213551A1 (en) | 2018-05-04 | 2019-11-07 | Perception Neuroscience, Inc. | Methods of treating substance abuse |
| BR112020023882A2 (pt) | 2018-06-27 | 2021-02-09 | Clexio Biosciences Ltd. | método para tratar transtorno depressivo maior |
| CN112702995A (zh) | 2018-10-05 | 2021-04-23 | 克雷西奥生物科技有限公司 | 治疗重度抑郁症的艾氯胺酮的治疗方案 |
| EP3863617A1 (en) | 2018-10-11 | 2021-08-18 | Clexio Biosciences Ltd. | Esketamine for use in treating major depressive disorder |
| KR20220002905A (ko) * | 2019-03-25 | 2022-01-07 | 더글라스 파머수티클스 리미티드 | 서방형 약학 제제 |
| US12589083B2 (en) | 2019-05-07 | 2026-03-31 | Clexio Biosciences Ltd. | Abuse-deterrent dosage forms containing esketamine |
| US11324707B2 (en) | 2019-05-07 | 2022-05-10 | Clexio Biosciences Ltd. | Abuse-deterrent dosage forms containing esketamine |
| CA3148992A1 (en) * | 2019-08-06 | 2021-02-11 | The Regents Of The University Of California | Scaleable preparation of polyketides |
| EP4041209A4 (en) | 2019-10-11 | 2024-01-24 | Pike Therapeutics, Inc. | TRANSDERMAL COMPOSITIONS COMPRISING CANNABIDIOL (CBD) FOR USE IN THE TREATMENT OF EPILEPTIC DISORDERS |
| EP4084786A1 (en) | 2019-12-30 | 2022-11-09 | Clexio Biosciences Ltd. | Dosage regime with esketamine for treating major depressive disorder |
| JP2023507926A (ja) | 2019-12-30 | 2023-02-28 | クレキシオ バイオサイエンシーズ エルティーディー． | 神経精神状態または神経学的状態を治療するためのエスケタミンを用いた投与計画 |
| WO2021137148A1 (en) * | 2019-12-30 | 2021-07-08 | Clexio Biosciences Ltd. | Dosage regime with esketamine for treating neuropsychiatric or neurological conditions |
| MX2022014599A (es) * | 2020-05-20 | 2022-12-16 | Certego Therapeutics Inc | Gaboxadol deuterado en anillo y su uso para el tratamiento de trastornos psiquiatricos. |
| CN114524737B (zh) * | 2020-11-23 | 2024-10-22 | 江苏恒瑞医药股份有限公司 | 一种取代的环己酮类化合物 |
| GB202019952D0 (en) * | 2020-12-17 | 2021-02-03 | Neurocentrx Pharma Ltd | Novel compositions |
| US20240207338A1 (en) * | 2021-04-30 | 2024-06-27 | Progressive Therapeutics Inc | Ketamine and cannabis for the treatment of emotional disorders |
| CN116730853A (zh) * | 2022-03-04 | 2023-09-12 | 上海致根医药科技有限公司 | 新型氨基酮类化合物及其制备方法和用途 |
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| US5250732A (en) | 1991-07-18 | 1993-10-05 | Genentech, Inc. | Ketamine analogues for treatment of thrombocytopenia |
| AUPN605795A0 (en) | 1995-10-19 | 1995-11-09 | F.H. Faulding & Co. Limited | Analgesic pharmaceutical composition |
| JP2006510618A (ja) * | 2002-11-18 | 2006-03-30 | ヤウポン セラピューティクス，インコーポレーテッド | ノルケタミンおよびケタミン／ノルケタミンプロドラッグの鎮痛的使用 |
| US20100076087A1 (en) * | 2005-10-06 | 2010-03-25 | Auspex Pharmaceuticals, Inc. | Methods of reduction of interpatient variability |
| US8765178B2 (en) * | 2006-07-19 | 2014-07-01 | Watson Laboratories, Inc. | Controlled release formulations and associated methods |
| BRPI0809843A2 (pt) * | 2007-04-26 | 2014-09-23 | Auspex Pharmaceuticals Inc | "composto, composição farmacêutica e uso de um composto" |
| WO2009131794A1 (en) * | 2008-03-27 | 2009-10-29 | University Of Kentucky Research Foundation | Opioid-ketamine and norketamine codrug combinations for pain management |
| CA2922507C (en) | 2013-08-26 | 2022-07-05 | Amorsa Therapeutics, Inc. | Single-layer oral dose of neuro-attenuating ketamine |
| DK3215147T3 (da) | 2014-11-04 | 2024-04-02 | Acadia Pharm Inc | Neurodæmpende norketamin-forbindelser og fremgangsmåder |
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