GB1436324A - Anaesthetic 3alpha-hydroxy pregnanes - Google Patents
Anaesthetic 3alpha-hydroxy pregnanesInfo
- Publication number
- GB1436324A GB1436324A GB2248972A GB2248972A GB1436324A GB 1436324 A GB1436324 A GB 1436324A GB 2248972 A GB2248972 A GB 2248972A GB 2248972 A GB2248972 A GB 2248972A GB 1436324 A GB1436324 A GB 1436324A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- prepared
- steroids
- alkyl
- alkylidene
- 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
- 230000003444 anaesthetic effect Effects 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 9
- 150000003431 steroids Chemical class 0.000 abstract 9
- -1 di-substituted amino Chemical group 0.000 abstract 7
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 238000003512 Claisen condensation reaction Methods 0.000 abstract 3
- 150000003855 acyl compounds Chemical class 0.000 abstract 3
- 150000001412 amines Chemical class 0.000 abstract 3
- 125000004103 aminoalkyl group Chemical class 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 150000001241 acetals Chemical class 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 abstract 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- CEBZORSAHLSRQW-AHUZIMQLSA-N (3r,8s,9s,10s,13r,14s,17s)-17-ethyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-ol Chemical class C1CC2C[C@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 CEBZORSAHLSRQW-AHUZIMQLSA-N 0.000 abstract 1
- PBXJGQQGODZSQR-HUWVKCSISA-N (5R,8R,9S,10S,13S,14S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid Chemical class [C@@H]12CCC([C@@]1(C)CC[C@H]1[C@H]2CC[C@H]2CCCC[C@]12C)C(=O)O PBXJGQQGODZSQR-HUWVKCSISA-N 0.000 abstract 1
- ALSXNTIVNJBNQE-ZWONNITHSA-N (8r,9r,10s,13r,14s,17s)-17-ethyl-13-methyl-1,2,3,4,5,6,7,8,9,10,11,12,14,15,16,17-hexadecahydrocyclopenta[a]phenanthrene Chemical class C1CC2CCCC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 ALSXNTIVNJBNQE-ZWONNITHSA-N 0.000 abstract 1
- LRJYSKANRZHUIH-DRPHTYIMSA-N 2-[(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]oxirane Chemical class O1C([C@H]2CC[C@@H]3[C@]2(C)CC[C@H]2[C@H]3CCC3CCCC[C@]23C)C1 LRJYSKANRZHUIH-DRPHTYIMSA-N 0.000 abstract 1
- NCVOSBYIFCSIHI-LDTRTVGNSA-N 3-[(3R,5S,8S,9S,10S,13S,14S,17S)-10,13-dimethyl-3-(oxan-2-yloxy)-11-oxo-1,2,3,4,5,6,7,8,9,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-3-oxopropanal Chemical compound C(=O)CC([C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](CC[C@]4(C)[C@H]3C(C[C@]12C)=O)OC1OCCCC1)=O NCVOSBYIFCSIHI-LDTRTVGNSA-N 0.000 abstract 1
- DUHUCHOQIDJXAT-OLVMNOGESA-N 3-hydroxy-(3-α,5-α)-Pregnane-11,20-dione 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=O DUHUCHOQIDJXAT-OLVMNOGESA-N 0.000 abstract 1
- JWMFYGXQPXQEEM-NUNROCCHSA-N 5β-pregnane Chemical compound C([C@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](CC)[C@@]2(C)CC1 JWMFYGXQPXQEEM-NUNROCCHSA-N 0.000 abstract 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 abstract 1
- 229910002651 NO3 Inorganic materials 0.000 abstract 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- DCDGIMIMLRIXPN-VKMGZQQJSA-N [(3R,5S,8S,9S,10S,13S,14S,17S)-17-(2-bromoacetyl)-10,13-dimethyl-11-oxo-1,2,3,4,5,6,7,8,9,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] nitrate Chemical compound C[C@]12CC(=O)[C@H]3[C@@H](CC[C@H]4C[C@@H](CC[C@]34C)O[N+]([O-])=O)[C@@H]1CC[C@@H]2C(=O)CBr DCDGIMIMLRIXPN-VKMGZQQJSA-N 0.000 abstract 1
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000005035 acylthio group Chemical group 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000006430 alkyl cyclopropyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000001118 alkylidene group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 229940124326 anaesthetic agent Drugs 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 150000007514 bases Chemical class 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 1
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 125000004965 chloroalkyl group Chemical group 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- 150000002009 diols Chemical class 0.000 abstract 1
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 abstract 1
- 239000003193 general anesthetic agent Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000002346 iodo group Chemical group I* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910017604 nitric acid Inorganic materials 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 238000010525 oxidative degradation reaction Methods 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 abstract 1
- 150000003128 pregnanes Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
- 230000000707 stereoselective effect Effects 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 abstract 1
- 229910052727 yttrium Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2248972A GB1436324A (en) | 1972-05-12 | 1972-05-12 | Anaesthetic 3alpha-hydroxy pregnanes |
| US05/358,381 US3998829A (en) | 1972-05-12 | 1973-05-08 | Steroid anaesthetics of the pregnane and 19-norpregnane series |
| LU67585A LU67585A1 (cg-RX-API-DMAC10.html) | 1972-05-12 | 1973-05-11 | |
| ZA733218A ZA733218B (en) | 1972-05-12 | 1973-05-11 | Compounds of the pregnene series having anaesthetic activity |
| CA171,026A CA1014947A (en) | 1972-05-12 | 1973-05-11 | Steroids of the pregnane series having anaesthetic activity |
| NL7306606A NL7306606A (cg-RX-API-DMAC10.html) | 1972-05-12 | 1973-05-11 | |
| JP48052424A JPS4948652A (cg-RX-API-DMAC10.html) | 1972-05-12 | 1973-05-11 | |
| BE131031A BE799433A (fr) | 1972-05-12 | 1973-05-11 | Composes anesthesiques de la serie du pregnane et leur preparation |
| DE2323950A DE2323950A1 (de) | 1972-05-12 | 1973-05-11 | Steroidverbindungen |
| AU55616/73A AU474687B2 (en) | 1972-05-12 | 1973-05-11 | Pregnane anaesthetics |
| DK260473AA DK135775B (da) | 1972-05-12 | 1973-05-11 | Analogifremgangsmåde til fremstilling af mættede 3alfa-hydroxy-5alfa-pregnaner. |
| IE00753/73A IE38863B1 (en) | 1972-05-12 | 1973-05-11 | Anaesthetic 3a-hydroxy pregnanes |
| FR7317079A FR2184711B1 (cg-RX-API-DMAC10.html) | 1972-05-12 | 1973-05-11 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2248972A GB1436324A (en) | 1972-05-12 | 1972-05-12 | Anaesthetic 3alpha-hydroxy pregnanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1436324A true GB1436324A (en) | 1976-05-19 |
Family
ID=10180241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2248972A Expired GB1436324A (en) | 1972-05-12 | 1972-05-12 | Anaesthetic 3alpha-hydroxy pregnanes |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3998829A (cg-RX-API-DMAC10.html) |
| JP (1) | JPS4948652A (cg-RX-API-DMAC10.html) |
| AU (1) | AU474687B2 (cg-RX-API-DMAC10.html) |
| BE (1) | BE799433A (cg-RX-API-DMAC10.html) |
| CA (1) | CA1014947A (cg-RX-API-DMAC10.html) |
| DE (1) | DE2323950A1 (cg-RX-API-DMAC10.html) |
| DK (1) | DK135775B (cg-RX-API-DMAC10.html) |
| FR (1) | FR2184711B1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1436324A (cg-RX-API-DMAC10.html) |
| IE (1) | IE38863B1 (cg-RX-API-DMAC10.html) |
| LU (1) | LU67585A1 (cg-RX-API-DMAC10.html) |
| NL (1) | NL7306606A (cg-RX-API-DMAC10.html) |
| ZA (1) | ZA733218B (cg-RX-API-DMAC10.html) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4613463A (en) * | 1984-11-01 | 1986-09-23 | The Upjohn Company | Process and intermediates for the preparation of 17 alphahydroxyprogesterones and corticoids from an enol steroid |
| US5099019A (en) * | 1985-09-12 | 1992-03-24 | Upjohn Company | Amines useful in producing pharmaceutically active CNS compounds |
| US5382661A (en) * | 1985-09-12 | 1995-01-17 | The Upjohn Company | Pyrazinylpiperazinyl steroids |
| USRE35053E (en) * | 1985-09-12 | 1995-10-10 | The Upjohn Company | Amines useful in producing pharmaceutically active CNS compounds |
| 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 |
| JPH072555Y2 (ja) * | 1991-06-03 | 1995-01-25 | 日野自動車工業株式会社 | 車輛の前後方向兼用ウインチ |
| PT837874E (pt) * | 1995-06-06 | 2005-03-31 | Euro Celtique Sa | Esteroides neuroactivos da serie androstano e pregnano |
| US6780853B1 (en) | 1995-06-06 | 2004-08-24 | Euro-Celtique S.A. | Neuroactive steroids of the androstane and pregnane series |
| US6143737A (en) * | 1995-06-23 | 2000-11-07 | Georgetown University | Progesterone analogs to reverse multidrug resistance |
| UA73736C2 (en) * | 1999-04-29 | 2005-09-15 | Euro Celtic S A | Method for alleviating or preventing insomnia and inducing anesthesia |
| US20050101581A1 (en) * | 2002-08-28 | 2005-05-12 | Reading Christopher L. | Therapeutic treatment methods 2 |
| EP4717314A2 (en) | 2011-10-14 | 2026-04-01 | Sage Therapeutics, LLC | 3,3 disubstituted 19-nor pregnane compounds, compositions, and uses thereof |
| WO2014169836A1 (en) | 2013-04-17 | 2014-10-23 | Sage Therapeutics, Inc. | 19-nor neuroactive steroids and methods of use thereof |
| US9725481B2 (en) | 2013-04-17 | 2017-08-08 | Sage Therapeutics, Inc. | 19-nor C3, 3-disubstituted C21-C-bound heteroaryl steroids and methods of use thereof |
| CN117304245A (zh) | 2013-04-17 | 2023-12-29 | 萨奇治疗股份有限公司 | 刺激神经活性的19-去甲类固醇及其使用方法 |
| SMT202100509T1 (it) | 2013-04-17 | 2021-11-12 | Sage Therapeutics Inc | Steroide di c21-n-pirazolile 19-nor c3,3-disostituito per l'uso in terapia |
| CA2918735C (en) | 2013-07-19 | 2023-08-01 | Sage Therapeutics, Inc. | Neuroactive steroids, compositions, and uses thereof |
| CN105579043B (zh) | 2013-08-23 | 2021-09-14 | 萨奇治疗股份有限公司 | 神经活性类固醇、组合物和其用途 |
| US10246482B2 (en) | 2014-06-18 | 2019-04-02 | Sage Therapeutics, Inc. | Neuroactive steroids, compositions, and uses thereof |
| MY190408A (en) | 2014-10-16 | 2022-04-21 | Sage Therapeutics Inc | Compositions and methods for treating cns disorders |
| US20170233433A1 (en) | 2014-10-16 | 2017-08-17 | 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 |
| LT3250210T (lt) | 2015-01-26 | 2021-04-12 | Sage Therapeutics, Inc. | Kompozicijos ir būdai, skirti gydyti cns sutrikimus |
| DK3258939T3 (da) | 2015-02-20 | 2022-12-12 | Sage Therapeutics Inc | Neuroaktive steroider, sammensætninger og anvendelser heraf |
| CA3030420C (en) | 2016-07-11 | 2025-11-18 | Sage Therapeutics, Inc. | C7, C12 AND C16 SUBSTITUTED NEUROACTIVE STEROIDS AND ASSOCIATED METHODS OF USE |
| WO2018013613A1 (en) | 2016-07-11 | 2018-01-18 | Sage Therapeutics, Inc. | C17, c20, and c21 substituted neuroactive steroids and their methods of use |
| JP7670626B2 (ja) | 2019-05-31 | 2025-04-30 | 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及びその組成物 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1107662B (de) * | 1959-07-04 | 1961-05-31 | Merck Ag E | Verfahren zur Herstellung von Mannichbasen von Steroiden bzw. von deren Saeureadditionssalzen |
| US3042691A (en) * | 1960-05-11 | 1962-07-03 | Pfizer & Co C | 5alpha,21-dibromo-6beta-fluoro-21-methyl-pregnanes and process for making same |
| FR1764M (fr) * | 1962-02-20 | 1963-04-08 | Roussel Uclaf | Nouveau médicament notamment pour le traitement des spasmes d'origine coronarienne ou viscérale. |
| US3201425A (en) * | 1963-12-10 | 1965-08-17 | American Cyanamid Co | 20-alkoxy-delta20-21-carboxaldehydes of the pregnane series and method of preparing the same |
| GB1089945A (en) * | 1965-09-23 | 1967-11-08 | British Drug Houses Ltd | Steroidal-6-spirocyclopropyl-4-en-3-ones |
| GB1317184A (en) * | 1969-06-20 | 1973-05-16 | Glaxo Lab Ltd | Steroid-containing pharmaceutical preparations |
| DE1941226A1 (de) * | 1969-08-13 | 1971-02-18 | Degussa | Basisch substituierte Ketosteroide |
| US3661940A (en) * | 1970-04-13 | 1972-05-09 | Sandoz Ag | Derivatives of 21-methyl-19-norpregnanes |
| GB1377609A (en) * | 1970-12-17 | 1974-12-18 | Glaxo Lab Ltd | 3alpha-hydroxy-5alpha-pregnane compounds |
| GB1416427A (en) * | 1972-01-12 | 1975-12-03 | Akzo Nv | Alkylated pregnanes and process for obtaining same |
-
1972
- 1972-05-12 GB GB2248972A patent/GB1436324A/en not_active Expired
-
1973
- 1973-05-08 US US05/358,381 patent/US3998829A/en not_active Expired - Lifetime
- 1973-05-11 DK DK260473AA patent/DK135775B/da unknown
- 1973-05-11 ZA ZA733218A patent/ZA733218B/xx unknown
- 1973-05-11 JP JP48052424A patent/JPS4948652A/ja active Pending
- 1973-05-11 NL NL7306606A patent/NL7306606A/xx not_active Application Discontinuation
- 1973-05-11 CA CA171,026A patent/CA1014947A/en not_active Expired
- 1973-05-11 LU LU67585A patent/LU67585A1/xx unknown
- 1973-05-11 BE BE131031A patent/BE799433A/xx unknown
- 1973-05-11 IE IE00753/73A patent/IE38863B1/xx unknown
- 1973-05-11 FR FR7317079A patent/FR2184711B1/fr not_active Expired
- 1973-05-11 AU AU55616/73A patent/AU474687B2/en not_active Expired
- 1973-05-11 DE DE2323950A patent/DE2323950A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| IE38863B1 (en) | 1978-06-21 |
| DE2323950A1 (de) | 1973-12-13 |
| AU474687B2 (en) | 1976-07-29 |
| AU5561673A (en) | 1974-11-14 |
| US3998829A (en) | 1976-12-21 |
| DK135775C (cg-RX-API-DMAC10.html) | 1977-11-21 |
| ZA733218B (en) | 1974-05-29 |
| LU67585A1 (cg-RX-API-DMAC10.html) | 1973-07-24 |
| BE799433A (fr) | 1973-11-12 |
| FR2184711A1 (cg-RX-API-DMAC10.html) | 1973-12-28 |
| FR2184711B1 (cg-RX-API-DMAC10.html) | 1977-01-07 |
| JPS4948652A (cg-RX-API-DMAC10.html) | 1974-05-11 |
| CA1014947A (en) | 1977-08-02 |
| DK135775B (da) | 1977-06-20 |
| IE38863L (en) | 1973-11-12 |
| NL7306606A (cg-RX-API-DMAC10.html) | 1973-11-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |