JP2016531134A5 - - Google Patents
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- JP2016531134A5 JP2016531134A5 JP2016536503A JP2016536503A JP2016531134A5 JP 2016531134 A5 JP2016531134 A5 JP 2016531134A5 JP 2016536503 A JP2016536503 A JP 2016536503A JP 2016536503 A JP2016536503 A JP 2016536503A JP 2016531134 A5 JP2016531134 A5 JP 2016531134A5
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- JP
- Japan
- Prior art keywords
- item
- pharmaceutically acceptable
- compound according
- alkyl
- acceptable 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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- 150000001875 compounds Chemical class 0.000 claims description 124
- 239000001257 hydrogen Substances 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 38
- 125000000623 heterocyclic group Chemical group 0.000 claims description 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- -1 nitro, hydroxy Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 11
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 3
- VQNDBXJTIJKJPV-UHFFFAOYSA-N 2h-triazolo[4,5-b]pyridine Chemical compound C1=CC=NC2=NNN=C21 VQNDBXJTIJKJPV-UHFFFAOYSA-N 0.000 claims description 3
- CBHTTYDJRXOHHL-UHFFFAOYSA-N 2h-triazolo[4,5-c]pyridazine Chemical compound N1=NC=CC2=C1N=NN2 CBHTTYDJRXOHHL-UHFFFAOYSA-N 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 3
- 239000012964 benzotriazole Substances 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 150000003536 tetrazoles Chemical class 0.000 claims description 3
- 150000003852 triazoles Chemical class 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 241000023320 Luma <angiosperm> Species 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 description 42
- 238000000034 method Methods 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
- 125000003545 alkoxy group Chemical group 0.000 description 10
- 208000035475 disorder Diseases 0.000 description 7
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 5
- 206010002091 Anaesthesia Diseases 0.000 description 5
- 230000037005 anaesthesia Effects 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
- 206010039897 Sedation Diseases 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 230000036280 sedation Effects 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- 125000006163 5-membered heteroaryl group Chemical group 0.000 description 3
- 206010010904 Convulsion Diseases 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- 208000009575 Angelman syndrome Diseases 0.000 description 2
- 206010003805 Autism Diseases 0.000 description 2
- 208000020706 Autistic disease Diseases 0.000 description 2
- 208000014644 Brain disease Diseases 0.000 description 2
- 208000001914 Fragile X syndrome Diseases 0.000 description 2
- 208000026139 Memory disease Diseases 0.000 description 2
- 208000019022 Mood disease Diseases 0.000 description 2
- 208000016285 Movement disease Diseases 0.000 description 2
- 208000006289 Rett Syndrome Diseases 0.000 description 2
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 2
- 208000009205 Tinnitus Diseases 0.000 description 2
- 206010048010 Withdrawal syndrome Diseases 0.000 description 2
- 208000010877 cognitive disease Diseases 0.000 description 2
- 230000036407 pain Effects 0.000 description 2
- 208000022821 personality disease Diseases 0.000 description 2
- 230000000698 schizophrenic effect Effects 0.000 description 2
- 208000019116 sleep disease Diseases 0.000 description 2
- 208000020685 sleep-wake disease Diseases 0.000 description 2
- 208000005809 status epilepticus Diseases 0.000 description 2
- 208000011117 substance-related disease Diseases 0.000 description 2
- 231100000886 tinnitus Toxicity 0.000 description 2
- 230000000472 traumatic effect Effects 0.000 description 2
- VVHBTPCUGVBTLJ-WCXQWVHUSA-N C[C@](CC1)([C@@H](CC2)[C@H](CC3)[C@H]1[C@@](COC)(CC1)[C@@H]3C[C@]1(C)O)[C@H]2C(C[n](c1c2)ncc1ccc2Cl)=O Chemical compound C[C@](CC1)([C@@H](CC2)[C@H](CC3)[C@H]1[C@@](COC)(CC1)[C@@H]3C[C@]1(C)O)[C@H]2C(C[n](c1c2)ncc1ccc2Cl)=O VVHBTPCUGVBTLJ-WCXQWVHUSA-N 0.000 description 1
- MESGFKUBBMXBKM-WCXQWVHUSA-N C[C@](CC1)([C@@H](CC2)[C@H](CC3)[C@H]1[C@@](COC)(CC1)[C@@H]3C[C@]1(C)O)[C@H]2C(C[n](c1c2)ncc1ccc2F)=O Chemical compound C[C@](CC1)([C@@H](CC2)[C@H](CC3)[C@H]1[C@@](COC)(CC1)[C@@H]3C[C@]1(C)O)[C@H]2C(C[n](c1c2)ncc1ccc2F)=O MESGFKUBBMXBKM-WCXQWVHUSA-N 0.000 description 1
- JUKIOILIHXZUES-DTZLGSCESA-N C[C@](CC1)([C@@H](CC2)[C@H](CC3)[C@H]1[C@@](COC)(CC1)[C@@H]3C[C@]1(C)O)[C@H]2C(C[n](c1ccc2F)nnc1c2F)=O Chemical compound C[C@](CC1)([C@@H](CC2)[C@H](CC3)[C@H]1[C@@](COC)(CC1)[C@@H]3C[C@]1(C)O)[C@H]2C(C[n](c1ccc2F)nnc1c2F)=O JUKIOILIHXZUES-DTZLGSCESA-N 0.000 description 1
- QTUAVIZHGUBOSP-APLVINOVSA-N C[C@](CC1)([C@@H](CC2)[C@H](CC3)[C@H]1[C@@](COC)(CC1)[C@@H]3C[C@]1(C)O)[C@H]2C(C[n](cc1)nc1C#N)=O Chemical compound C[C@](CC1)([C@@H](CC2)[C@H](CC3)[C@H]1[C@@](COC)(CC1)[C@@H]3C[C@]1(C)O)[C@H]2C(C[n](cc1)nc1C#N)=O QTUAVIZHGUBOSP-APLVINOVSA-N 0.000 description 1
- KOXFAJCPBYWCJO-DTZLGSCESA-N C[C@](CC1)([C@@H](CC2)[C@H](CC3)[C@H]1[C@@](COC)(CC1)[C@@H]3C[C@]1(C)O)[C@H]2C(C[n](nc1cc2)nc1c(F)c2F)=O Chemical compound C[C@](CC1)([C@@H](CC2)[C@H](CC3)[C@H]1[C@@](COC)(CC1)[C@@H]3C[C@]1(C)O)[C@H]2C(C[n](nc1cc2)nc1c(F)c2F)=O KOXFAJCPBYWCJO-DTZLGSCESA-N 0.000 description 1
- FMPVRYRZGYDZQH-WCXQWVHUSA-N C[C@](CC1)([C@@H](CC2)[C@H](CC3)[C@H]1[C@@](COC)(CC1)[C@@H]3C[C@]1(C)O)[C@H]2C(C[n]1nc(cc(cc2)Cl)c2c1)=O Chemical compound C[C@](CC1)([C@@H](CC2)[C@H](CC3)[C@H]1[C@@](COC)(CC1)[C@@H]3C[C@]1(C)O)[C@H]2C(C[n]1nc(cc(cc2)Cl)c2c1)=O FMPVRYRZGYDZQH-WCXQWVHUSA-N 0.000 description 1
- CQERWFMVBUSUPZ-WCXQWVHUSA-N C[C@](CC1)([C@@H](CC2)[C@H](CC3)[C@H]1[C@@](COC)(CC1)[C@@H]3C[C@]1(C)O)[C@H]2C(C[n]1nc(cc(cc2)F)c2c1)=O Chemical compound C[C@](CC1)([C@@H](CC2)[C@H](CC3)[C@H]1[C@@](COC)(CC1)[C@@H]3C[C@]1(C)O)[C@H]2C(C[n]1nc(cc(cc2)F)c2c1)=O CQERWFMVBUSUPZ-WCXQWVHUSA-N 0.000 description 1
- WGLNKRFCOUXFJS-MEYBVDQASA-N C[C@](CC1)([C@@H](CC2)[C@H](CC3)[C@H]1[C@@](COC)(CC1)[C@@H]3C[C@]1(C)O)[C@H]2C(C[n]1nnc(C)n1)=O Chemical compound C[C@](CC1)([C@@H](CC2)[C@H](CC3)[C@H]1[C@@](COC)(CC1)[C@@H]3C[C@]1(C)O)[C@H]2C(C[n]1nnc(C)n1)=O WGLNKRFCOUXFJS-MEYBVDQASA-N 0.000 description 1
- HNAWNTCTAUIJCQ-DTZLGSCESA-N C[C@](CC1)([C@@H](CC2)[C@H](CC3)[C@H]1[C@@](COC)(CC1)[C@@H]3C[C@]1(C)O)[C@H]2C(C[n]1nnc(cc2)c1c(F)c2F)=O Chemical compound C[C@](CC1)([C@@H](CC2)[C@H](CC3)[C@H]1[C@@](COC)(CC1)[C@@H]3C[C@]1(C)O)[C@H]2C(C[n]1nnc(cc2)c1c(F)c2F)=O HNAWNTCTAUIJCQ-DTZLGSCESA-N 0.000 description 1
- LZBNHOMYDURDCI-MEYBVDQASA-N C[C@](CC1)([C@@H](CC2)[C@H](CC3)[C@H]1[C@@](COC)(CC1)[C@@H]3C[C@]1(C)O)[C@H]2C(C[n]1nnnc1C)=O Chemical compound C[C@](CC1)([C@@H](CC2)[C@H](CC3)[C@H]1[C@@](COC)(CC1)[C@@H]3C[C@]1(C)O)[C@H]2C(C[n]1nnnc1C)=O LZBNHOMYDURDCI-MEYBVDQASA-N 0.000 description 1
- 206010013654 Drug abuse Diseases 0.000 description 1
- 102000005915 GABA Receptors Human genes 0.000 description 1
- 108010005551 GABA Receptors Proteins 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 208000012201 sexual and gender identity disease Diseases 0.000 description 1
- 208000015891 sexual disease Diseases 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 201000009032 substance abuse Diseases 0.000 description 1
- 231100000736 substance abuse Toxicity 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361869446P | 2013-08-23 | 2013-08-23 | |
| US201361869440P | 2013-08-23 | 2013-08-23 | |
| US61/869,440 | 2013-08-23 | ||
| US61/869,446 | 2013-08-23 | ||
| US201462014018P | 2014-06-18 | 2014-06-18 | |
| US62/014,018 | 2014-06-18 | ||
| PCT/US2014/052417 WO2015027227A1 (en) | 2013-08-23 | 2014-08-22 | Neuroactive steroids, compositions, and uses thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019002860A Division JP6826615B2 (ja) | 2013-08-23 | 2019-01-10 | 向神経活性ステロイド、組成物、及びその使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016531134A JP2016531134A (ja) | 2016-10-06 |
| JP2016531134A5 true JP2016531134A5 (https=) | 2017-09-28 |
| JP6466942B2 JP6466942B2 (ja) | 2019-02-06 |
Family
ID=52484216
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016536503A Active JP6466942B2 (ja) | 2013-08-23 | 2014-08-22 | 向神経活性ステロイド、組成物、及びその使用 |
| JP2019002860A Active JP6826615B2 (ja) | 2013-08-23 | 2019-01-10 | 向神経活性ステロイド、組成物、及びその使用 |
| JP2020193080A Active JP7269911B2 (ja) | 2013-08-23 | 2020-11-20 | 向神経活性ステロイド、組成物、及びその使用 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019002860A Active JP6826615B2 (ja) | 2013-08-23 | 2019-01-10 | 向神経活性ステロイド、組成物、及びその使用 |
| JP2020193080A Active JP7269911B2 (ja) | 2013-08-23 | 2020-11-20 | 向神経活性ステロイド、組成物、及びその使用 |
Country Status (20)
| Country | Link |
|---|---|
| US (3) | US20160229887A1 (https=) |
| EP (3) | EP3488852B1 (https=) |
| JP (3) | JP6466942B2 (https=) |
| CN (2) | CN105579043B (https=) |
| AU (3) | AU2014308621C1 (https=) |
| BR (1) | BR112016003862B1 (https=) |
| CA (2) | CA3235088A1 (https=) |
| CY (1) | CY1124112T1 (https=) |
| DK (1) | DK3488852T3 (https=) |
| ES (2) | ES2848823T3 (https=) |
| HK (1) | HK1225977B (https=) |
| HU (1) | HUE052308T2 (https=) |
| LT (1) | LT3488852T (https=) |
| PL (1) | PL3488852T3 (https=) |
| PT (2) | PT3488852T (https=) |
| RS (1) | RS61370B1 (https=) |
| RU (1) | RU2696585C2 (https=) |
| SI (1) | SI3488852T1 (https=) |
| SM (1) | SMT202100048T1 (https=) |
| WO (1) | WO2015027227A1 (https=) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN119192266A (zh) | 2011-10-14 | 2024-12-27 | 萨奇治疗股份有限公司 | 3,3-二取代的19-去甲孕甾烷化合物、组合物、及其用途 |
| MX2015002252A (es) | 2012-08-21 | 2015-07-21 | Sage Therapeutics Inc | Metodos para tratar epilepsia o estado de epilepsia. |
| MX365644B (es) | 2012-12-18 | 2019-06-10 | Univ Washington | Esteroides neuroactivos sustituidos con 19-alcoxi-17, profarmacos de los mismos, y metodos de tratamiento usando los mismos. |
| WO2014169836A1 (en) | 2013-04-17 | 2014-10-23 | Sage Therapeutics, Inc. | 19-nor neuroactive steroids and methods of use thereof |
| JP6470258B2 (ja) | 2013-04-17 | 2019-02-13 | セージ セラピューティクス， インコーポレイテッド | １９−ノルｃ３，３−ジ置換ｃ２１−ｎ−ピラゾリルステロイドおよびその使用方法 |
| WO2014169831A1 (en) | 2013-04-17 | 2014-10-23 | Sage Therapeutics, Inc. | 19-nor c3,3-disubstituted c21-c-bound heteroaryl steroids and methods of use thereof |
| ES2807264T3 (es) | 2013-04-17 | 2021-02-22 | Sage Therapeutics Inc | Esteroides neuroactivos 19-nor para métodos de tratamiento |
| WO2015010054A2 (en) | 2013-07-19 | 2015-01-22 | Sage Therapeutics, Inc. | Neuroactive steroids, compositions, and uses thereof |
| ES2848823T3 (es) | 2013-08-23 | 2021-08-12 | Sage Therapeutics Inc | Esteroides neuroactivos, composiciones y usos de los mismos |
| WO2015195962A1 (en) | 2014-06-18 | 2015-12-23 | Sage Therapeutics, Inc. | Neuroactive steroids, compositions, and uses thereof |
| JOP20200195A1 (ar) | 2014-09-08 | 2017-06-16 | Sage Therapeutics Inc | سترويدات وتركيبات نشطة عصبياً، واستخداماتها |
| ME03809B (me) | 2014-10-16 | 2021-04-20 | Sage Therapeutics Inc | KOMPOZICIJE I POSTUPCI ZA LEČENJE POREMEĆAJA CNS-a |
| US10577390B2 (en) | 2014-10-16 | 2020-03-03 | Sage Therapeutics, Inc. | Compositions and methods for treating CNS disorders |
| WO2016082789A1 (en) | 2014-11-27 | 2016-06-02 | Sage Therapeutics, Inc. | Compositions and methods for treating cns disorders |
| WO2016123056A1 (en) | 2015-01-26 | 2016-08-04 | Sage Therapeutics, Inc. | Compositions and methods for treating cns disorders |
| EP4155314A1 (en) * | 2015-02-20 | 2023-03-29 | Sage Therapeutics, Inc. | Neuroactive steroids, compositions, and uses thereof |
| AR105044A1 (es) | 2015-06-18 | 2017-08-30 | Sage Therapeutics Inc | Soluciones de esteroides neuroactivos y sus métodos de uso, recipiente |
| EA036155B1 (ru) | 2015-10-16 | 2020-10-06 | Маринус Фармасьютикалс, Инк. | Инъекционные составы нейростероида, содержащие наночастицы |
| HK1258616A1 (zh) | 2016-03-08 | 2019-11-15 | Sage Therapeutics, Inc. | 神经活性类固醇、组合物、及其用途 |
| MA45599A (fr) | 2016-07-11 | 2019-05-15 | Sage Therapeutics Inc | Stéroïdes neuroactifs substitués en c17, c20 et c21 et leurs procédés d'utilisation |
| US20190233465A1 (en) | 2016-07-11 | 2019-08-01 | Sage Therapeutics, Inc. | C7, c12, and c16 substituted neuroactive steroids and their methods of use |
| TWI904593B (zh) | 2016-08-23 | 2025-11-11 | 美商賽吉醫療公司 | 結晶19-去甲c3,3-二取代之c21-n-吡唑類固醇 |
| US10391105B2 (en) | 2016-09-09 | 2019-08-27 | Marinus Pharmaceuticals Inc. | Methods of treating certain depressive disorders and delirium tremens |
| EP3720867A1 (en) | 2017-12-08 | 2020-10-14 | Sage Therapeutics, Inc. | Deuterated 21 -[4-cyano-pyrazol-1 -yl]-19-nor-pregan-3. alpha-ol-20-one derivatives for treating cns disorders |
| EP3728284B1 (en) * | 2017-12-22 | 2024-08-21 | Sage Therapeutics, Inc. | 19-homo, 3.alpha.-hydroxy-steroid-20-one compounds for treating cns disorders |
| CN114656514B (zh) | 2018-02-11 | 2024-05-14 | 江苏豪森药业集团有限公司 | 一种甾族类衍生物调节剂及其制备方法和应用 |
| CN109503694A (zh) * | 2018-11-21 | 2019-03-22 | 苏州闻天医药科技有限公司 | 一种新型gabaa受体调节剂及其用途 |
| GB201903664D0 (en) * | 2019-03-18 | 2019-05-01 | Univ Edinburgh | Small, orthogonal and tunable dyes and photosensitizers |
| CR20240234A (es) | 2019-05-31 | 2024-07-09 | Sage Therapeutics Inc | ESTEROIDES NEUROACTIVOS Y COMPOSICIONES DE ESTOS (Divisional 2021-629) |
| CN118027131A (zh) | 2019-08-07 | 2024-05-14 | 上海翰森生物医药科技有限公司 | 一种甾族类衍生物调节剂的盐及其晶型 |
| US10857163B1 (en) | 2019-09-30 | 2020-12-08 | Athenen Therapeutics, Inc. | Compositions that preferentially potentiate subtypes of GABAA receptors and methods of use thereof |
| KR20220157426A (ko) | 2020-03-25 | 2022-11-29 | 세이지 테라퓨틱스, 인크. | 호흡기 병태의 치료를 위한 작용제의 용도 |
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| US3206459A (en) | 1962-10-19 | 1965-09-14 | Syntex Corp | 10alpha-pregnan-19-ol derivatives |
| US3169134A (en) | 1963-03-21 | 1965-02-09 | Searle & Co | 2, 3-oxygenated-17alpha-methyl-5alpha-androstan-17beta-ols |
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| GB1380246A (en) | 1970-12-17 | 1975-01-08 | Glaxo Lab Ltd | 3alpha-hydroxy-androstanes and esters thereof |
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| GB1430942A (en) | 1972-05-05 | 1976-04-07 | Glaxo Lab Ltd | 21-substituted 3alpha-hydroxy pregnanes |
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