JPS6146480B2 - - Google Patents
Info
- Publication number
- JPS6146480B2 JPS6146480B2 JP51067563A JP6756376A JPS6146480B2 JP S6146480 B2 JPS6146480 B2 JP S6146480B2 JP 51067563 A JP51067563 A JP 51067563A JP 6756376 A JP6756376 A JP 6756376A JP S6146480 B2 JPS6146480 B2 JP S6146480B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- hydroxy
- formula
- general formula
- iodobenzoyl
- 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.)
- Expired
Links
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 6
- -1 steroid ester Chemical class 0.000 claims description 6
- KVBWBCRPWVKFQT-UHFFFAOYSA-N 3-iodobenzoic acid Chemical compound OC(=O)C1=CC=CC(I)=C1 KVBWBCRPWVKFQT-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- KSRHWBLHVZJTKV-UHFFFAOYSA-N iodobenzene dichloride Chemical compound ClI(Cl)C1=CC=CC=C1 KSRHWBLHVZJTKV-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 230000008018 melting Effects 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- VGJKBWPZBVBXGI-UHFFFAOYSA-N 1,2-dichloro-3-iodobenzene Chemical compound ClC1=CC=CC(I)=C1Cl VGJKBWPZBVBXGI-UHFFFAOYSA-N 0.000 description 3
- RSRDWHPVTMQUGZ-OZIWPBGVSA-N 1-[(8r,9s,10s,13s,14s,17s)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RSRDWHPVTMQUGZ-OZIWPBGVSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 235000011118 potassium hydroxide Nutrition 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 150000003431 steroids Chemical class 0.000 description 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
- AURFZBICLPNKBZ-FZCSVUEKSA-N 3beta-hydroxy-5alpha-pregnan-20-one Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)C)[C@@]2(C)CC1 AURFZBICLPNKBZ-FZCSVUEKSA-N 0.000 description 2
- RBWNDBNSJFCLBZ-UHFFFAOYSA-N 7-methyl-5,6,7,8-tetrahydro-3h-[1]benzothiolo[2,3-d]pyrimidine-4-thione Chemical compound N1=CNC(=S)C2=C1SC1=C2CCC(C)C1 RBWNDBNSJFCLBZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002168 ethanoic acid esters Chemical class 0.000 description 2
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FAFCMRWYAIRVDU-CSMRHZIVSA-N 1-[(3r,5s,8s,10s,13s,14s,17s)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound C1[C@H](O)CC[C@]2(C)C3=CC[C@]4(C)[C@@H](C(=O)C)CC[C@H]4[C@@H]3CC[C@H]21 FAFCMRWYAIRVDU-CSMRHZIVSA-N 0.000 description 1
- DOIUYMHEABAPBH-VDMKTYGSSA-N 19-Nor-5alpha-pregnane-3,20-dione Chemical compound C([C@@H]1CC2)C(=O)CC[C@@H]1[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)C)[C@@]2(C)CC1 DOIUYMHEABAPBH-VDMKTYGSSA-N 0.000 description 1
- JUQJEDUDGZZGLN-JIUSCHCVSA-N 2-chloro-1-[(8r,9s,10s,13s,14s,17s)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CCl)[C@@H]4[C@@H]3CCC21 JUQJEDUDGZZGLN-JIUSCHCVSA-N 0.000 description 1
- CJNZAXGUTKBIHP-UHFFFAOYSA-N 2-iodobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1I CJNZAXGUTKBIHP-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa
- C07J7/002—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa not substituted in position 16
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2526373A DE2526373C2 (de) | 1975-06-11 | 1975-06-11 | Verfahren zur Herstellung von Δ↑9↑↑(↑↑1↑↑1↑↑)↑-5α-20-Ketosteroiden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51149260A JPS51149260A (en) | 1976-12-22 |
| JPS6146480B2 true JPS6146480B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1986-10-14 |
Family
ID=5948981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51067563A Granted JPS51149260A (en) | 1975-06-11 | 1976-06-09 | Production of delta 9 *11* 5 alphaa200ketosterod |
Country Status (10)
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2748442C3 (de) * | 1977-10-26 | 1981-08-27 | Schering Ag Berlin Und Bergkamen, 1000 Berlin | 17α-(3-Jodbenzoyloxy)-9α -chlor4-pregnen-3.20-dione, Zwischenprodukte und Verfahren zu ihrer Herstellung, 9α -chlor-17α, 21-dihydroxy-1,4-pregnadien-3,20-dion und dieses enthaltende Arzneimittel |
| US4252729A (en) * | 1978-05-12 | 1981-02-24 | Hoffmann-La Roche Inc. | Steroids and process for their manufacture |
| US4252719A (en) * | 1978-08-17 | 1981-02-24 | Research Corporation | Steroid conversion method and products produced thereby |
| DE2929558C2 (de) * | 1979-07-18 | 1982-03-11 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Verfahren zur Herstellung von Δ↑9↑↑(↑↑1↑↑1↑↑)↑ und/oder Δ↑1↑↑6↑ ungesättigten Steroiden |
| US4328162A (en) * | 1980-09-05 | 1982-05-04 | Eastman Kodak Company | Process for preparing 9,11-unsaturated steroidal compound from the corresponding saturated steroidal compound |
| US5232917A (en) * | 1987-08-25 | 1993-08-03 | University Of Southern California | Methods, compositions, and compounds for allosteric modulation of the GABA receptor by members of the androstane and pregnane series |
| PT2766380T (pt) | 2011-10-14 | 2019-07-29 | Sage Therapeutics Inc | Compostos de 19-nor pregnano 3,3-dissubstituídos, composições e seus usos |
| SMT201900066T1 (it) | 2013-04-17 | 2019-02-28 | Sage Therapeutics Inc | Steroidi di c21-n-pirazolile 19-nor c3,3-disostituiti e metodi d’uso degli stessi |
| WO2014169836A1 (en) | 2013-04-17 | 2014-10-23 | Sage Therapeutics, Inc. | 19-nor neuroactive steroids and methods of use thereof |
| 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 |
| HUE051403T2 (hu) | 2013-04-17 | 2021-03-01 | Sage Therapeutics Inc | Neuroaktív 19-nor-szteroidok kezelési eljárásokhoz |
| PT3021852T (pt) | 2013-07-19 | 2021-04-21 | Sage Therapeutics Inc | Esteroides neuroativos, composições e utilizações das mesmas |
| WO2015027227A1 (en) | 2013-08-23 | 2015-02-26 | Sage Therapeutics, Inc. | Neuroactive steroids, compositions, and uses thereof |
| US10246482B2 (en) | 2014-06-18 | 2019-04-02 | Sage Therapeutics, Inc. | Neuroactive steroids, compositions, and uses thereof |
| US10577390B2 (en) | 2014-10-16 | 2020-03-03 | Sage Therapeutics, Inc. | Compositions and methods for treating CNS disorders |
| SMT202000414T1 (it) | 2014-10-16 | 2020-09-10 | Sage Therapeutics Inc | Composizioni e metodi per trattare disturbi del snc |
| EP3719029A1 (en) | 2014-11-27 | 2020-10-07 | Sage Therapeutics, Inc. | Compositions for inducing sedation |
| ES2857082T3 (es) | 2015-01-26 | 2021-09-28 | Sage Therapeutics Inc | Composiciones y métodos para el tratamiento de trastornos del SNC |
| JP6875996B2 (ja) | 2015-02-20 | 2021-05-26 | セージ セラピューティクス， インコーポレイテッド | 神経刺激性ステロイド、組成物、およびその使用 |
| US20180311258A1 (en) * | 2015-04-10 | 2018-11-01 | Sage Therapeutics, Inc. | Compositions and methods for treating cns disorders |
| JP7065825B2 (ja) | 2016-07-11 | 2022-05-12 | セージ セラピューティクス， インコーポレイテッド | Ｃ７、ｃ１２、およびｃ１６置換神経刺激性ステロイドおよびそれらの使用方法 |
| MA45599A (fr) | 2016-07-11 | 2019-05-15 | Sage Therapeutics Inc | Stéroïdes neuroactifs substitués en c17, c20 et c21 et leurs procédés d'utilisation |
| EP3712161A1 (en) * | 2019-03-19 | 2020-09-23 | Bionice, S.L.U. | Process for preparing high puritiy allopregnanolone and intermediates thereof |
| CA3139554A1 (en) | 2019-05-31 | 2020-12-03 | Sage Therapeutics, Inc. | Neuroactive steroids and compositions thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2681353A (en) * | 1952-03-11 | 1954-06-15 | Sterling Drug Inc | Chlorination of keto-steroids |
| GB1380248A (en) * | 1970-12-17 | 1975-01-08 | Glaxo Lab Ltd | 3alpha-hydroxy steroids and esters thereof |
-
1975
- 1975-06-11 DE DE2526373A patent/DE2526373C2/de not_active Expired
-
1976
- 1976-06-08 US US05/693,848 patent/US4061661A/en not_active Expired - Lifetime
- 1976-06-08 NL NL7606137A patent/NL7606137A/xx not_active Application Discontinuation
- 1976-06-09 JP JP51067563A patent/JPS51149260A/ja active Granted
- 1976-06-09 CH CH726176A patent/CH620452A5/de not_active IP Right Cessation
- 1976-06-09 GB GB23849/76A patent/GB1554901A/en not_active Expired
- 1976-06-09 DD DD193275A patent/DD125699A5/xx unknown
- 1976-06-10 HU HU76SCHE569A patent/HU174227B/hu not_active IP Right Cessation
- 1976-06-11 FR FR7617698A patent/FR2314197A1/fr active Granted
- 1976-06-11 DK DK260976A patent/DK137837C/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2314197A1 (fr) | 1977-01-07 |
| DK137837C (da) | 1978-10-23 |
| DE2526373C2 (de) | 1983-11-10 |
| DD125699A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-05-11 |
| DK137837B (da) | 1978-05-16 |
| FR2314197B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-03-20 |
| CH620452A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-11-28 |
| US4061661A (en) | 1977-12-06 |
| HU174227B (hu) | 1979-11-28 |
| NL7606137A (nl) | 1976-12-14 |
| DK260976A (da) | 1976-12-12 |
| JPS51149260A (en) | 1976-12-22 |
| DE2526373A1 (de) | 1976-12-30 |
| GB1554901A (en) | 1979-10-31 |
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