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
- 230000007135 neurotoxicity Effects 0.000 claims description 7
- 231100000228 neurotoxicity Toxicity 0.000 claims description 7
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- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 5
- 208000012661 Dyskinesia Diseases 0.000 claims description 5
- 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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- 229960004502 levodopa Drugs 0.000 claims description 5
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- 238000000034 method Methods 0.000 description 51
- 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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- 208000030886 Traumatic Brain injury Diseases 0.000 description 3
- 201000007930 alcohol dependence Diseases 0.000 description 3
- 206010003246 arthritis Diseases 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- 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
- 206010027599 migraine Diseases 0.000 description 3
- 239000006187 pill Substances 0.000 description 3
- 230000036470 plasma concentration Effects 0.000 description 3
- 208000016691 refractory malignant neoplasm Diseases 0.000 description 3
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- 208000004371 toothache Diseases 0.000 description 3
- 230000009529 traumatic brain injury Effects 0.000 description 3
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 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
- 230000016571 aggressive behavior Effects 0.000 description 1
- 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
- 239000000679 carrageenan Substances 0.000 description 1
- 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
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 235000010494 karaya gum Nutrition 0.000 description 1
- 239000000231 karaya gum Substances 0.000 description 1
- 229940039371 karaya gum Drugs 0.000 description 1
- 235000010420 locust bean gum Nutrition 0.000 description 1
- 239000000711 locust bean gum Substances 0.000 description 1
- 238000007726 management method Methods 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229960000292 pectin Drugs 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
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- 201000006137 substance-induced psychosis Diseases 0.000 description 1
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- 229920001285 xanthan gum 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 (OSRAM) | 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 (5) | US10252982B2 (OSRAM) |
| EP (2) | EP3215147B1 (OSRAM) |
| JP (2) | JP6882180B2 (OSRAM) |
| KR (1) | KR102604397B1 (OSRAM) |
| CN (2) | CN107106529A (OSRAM) |
| AU (1) | AU2015343083B2 (OSRAM) |
| CA (1) | CA2966737A1 (OSRAM) |
| DK (1) | DK3215147T3 (OSRAM) |
| ES (1) | ES2977383T3 (OSRAM) |
| FI (1) | FI3215147T3 (OSRAM) |
| HU (1) | HUE066468T2 (OSRAM) |
| LT (1) | LT3215147T (OSRAM) |
| PL (1) | PL3215147T3 (OSRAM) |
| PT (1) | PT3215147T (OSRAM) |
| RS (1) | RS65411B1 (OSRAM) |
| RU (1) | RU2771275C2 (OSRAM) |
| SI (1) | SI3215147T1 (OSRAM) |
| WO (1) | WO2016073653A1 (OSRAM) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015065547A1 (en) | 2013-10-31 | 2015-05-07 | Cima Labs Inc. | Immediate release abuse-deterrent granulated dosage forms |
| ES2829279T3 (es) | 2014-04-17 | 2021-05-31 | Develco Pharma Schweiz Ag | Forma de dosificación oral de ketamina |
| US10252982B2 (en) | 2014-11-04 | 2019-04-09 | Amorsa Therapeutics, Inc. | Neuro-attenuating ketamine and norketamine compounds, derivatives thereof, and methods |
| WO2016186968A1 (en) * | 2015-05-15 | 2016-11-24 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | Compositions and methods for treating motor disorders |
| JP6845162B2 (ja) | 2015-06-27 | 2021-03-17 | シェノックス・ファーマシューティカルズ・エルエルシー | ケタミン経皮送達システム |
| WO2017180589A1 (en) * | 2016-04-11 | 2017-10-19 | Auspex Pharmaceuticals, Inc. | Deuterated ketamine derivatives |
| CN110035997A (zh) * | 2016-09-16 | 2019-07-19 | 生物制药沃克斯有限公司 | 羟基去甲氯胺酮前药 |
| AU2017351437B2 (en) * | 2016-10-27 | 2022-01-27 | National University Corporation Chiba University | Application of (S)-norketamine and salt thereof as pharmaceutical |
| EP3609481A4 (en) | 2017-04-13 | 2021-05-26 | Ovid Therapeutics Inc. | DEVELOPMENTAL ENCEPHALOPATHY TREATMENT METHODS |
| EP3641742A2 (en) * | 2017-06-23 | 2020-04-29 | Develco Pharma Schweiz AG | Hydroxynorketamine for the use in the treatment of depression |
| EP3532457B1 (en) | 2017-07-31 | 2020-03-18 | Small Pharma Ltd | Crystalline forms of hydroxynorketamine |
| US10869838B2 (en) | 2017-10-10 | 2020-12-22 | Douglas Pharmaceuticals, Ltd. | Extended release pharmaceutical formulation |
| US11471415B2 (en) | 2017-10-10 | 2022-10-18 | Douglas Pharmaceuticals, Ltd. | Extended release pharmaceutical formulation and methods of treatment |
| US12090123B2 (en) | 2017-10-10 | 2024-09-17 | Douglas Pharmaceuticals Ltd. | Extended release pharmaceutical formulation |
| MX2020003546A (es) | 2017-10-10 | 2020-08-03 | Douglas Pharmaceuticals Ltd | Formulacion farmaceutica de liberacion prolongada y metodos de tratamiento. |
| US10441544B2 (en) | 2017-10-10 | 2019-10-15 | Douglas Pharmaceuticals, Ltd. | Extended release pharmaceutical formulation |
| EP3501503A1 (en) * | 2017-12-22 | 2019-06-26 | Cosmo Technologies Ltd. | Solid delivery composition |
| PL3505157T3 (pl) | 2017-12-29 | 2022-04-11 | Celon Pharma S.A. | Kompozycja ketaminy w postaci suchego proszku do podawania dopłucnego w leczeniu depresji opornej na leczenie |
| EP3753557B1 (en) | 2018-02-15 | 2025-11-05 | National University Corporation Chiba University | Preventive or therapeutic agent and pharmaceutical composition for inflammatory diseases or bone diseases |
| CA3099293A1 (en) | 2018-05-04 | 2019-11-07 | Perception Neuroscience, Inc. | Methods of treating substance abuse |
| CN112188889A (zh) | 2018-06-27 | 2021-01-05 | 克雷西奥生物科技有限公司 | 治疗重度抑郁症的方法 |
| EP3860579A1 (en) | 2018-10-05 | 2021-08-11 | Clexio Biosciences Ltd. | Dosage regime of esketamine for treating major depressive disorder |
| EP3863617A1 (en) | 2018-10-11 | 2021-08-18 | Clexio Biosciences Ltd. | Esketamine for use in treating major depressive disorder |
| CA3130039C (en) * | 2019-03-25 | 2025-04-15 | Douglas Pharmaceuticals Ltd. | SOLID, DELAYED-RELEASE PHARMACEUTICAL FORMULATIONS CONTAINING KETAMINE OR NORKETAMIN |
| US20220062200A1 (en) | 2019-05-07 | 2022-03-03 | Clexio Biosciences Ltd. | Abuse-deterrent dosage forms containing esketamine |
| WO2020225773A1 (en) | 2019-05-07 | 2020-11-12 | Clexio Biosciences Ltd. | Abuse-deterrent dosage forms containing esketamine |
| CN120817937A (zh) * | 2019-08-06 | 2025-10-21 | 加利福尼亚大学董事会 | 聚酮化合物及其制备方法和中间体 |
| JP7670700B2 (ja) | 2019-10-11 | 2025-04-30 | パイク セラピューティクス インコーポレイテッド | 発作性障害の治療用のカンナビジオール（ｃｂｄ）を含む経皮医薬組成物 |
| IL293506A (en) | 2019-12-30 | 2022-08-01 | Clexio Biosciences Ltd | Dosage regime with esketamine for treating major depressive disorder |
| WO2021137148A1 (en) * | 2019-12-30 | 2021-07-08 | Clexio Biosciences Ltd. | Dosage regime with esketamine for treating neuropsychiatric or neurological conditions |
| US12478592B2 (en) | 2019-12-30 | 2025-11-25 | Clexio Biosciences Ltd. | Dosage regime with esketamine for treating neuropsychiatric or neurological conditions |
| JP2023526439A (ja) | 2020-05-20 | 2023-06-21 | セルテゴ セラピューティクス インコーポレイテッド | 精神障害の処置のための環重水素化ガボキサドールおよびその使用 |
| 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 |
| EP4329737A1 (en) * | 2021-04-30 | 2024-03-06 | 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 |
| AU2003291037A1 (en) | 2002-11-18 | 2004-06-15 | Yaupon Therapeutics, Inc. | Analgesic uses of norketamine and ketamine/norketamine prodrugs |
| 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 |
| CN101765582A (zh) * | 2007-04-26 | 2010-06-30 | 奥斯拜客斯制药有限公司 | 氘标记的氯胺酮 |
| WO2009131794A1 (en) * | 2008-03-27 | 2009-10-29 | University Of Kentucky Research Foundation | Opioid-ketamine and norketamine codrug combinations for pain management |
| US9913803B2 (en) | 2013-08-26 | 2018-03-13 | Amorsa Therapeutics, Inc. | Single-layer oral dose of neuro-attenuating ketamine |
| US10252982B2 (en) | 2014-11-04 | 2019-04-09 | Amorsa Therapeutics, Inc. | Neuro-attenuating ketamine and norketamine compounds, derivatives thereof, and methods |
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