GB1589787A - Pro-drugs for certain steroids - Google Patents
Pro-drugs for certain steroids Download PDFInfo
- Publication number
- GB1589787A GB1589787A GB42298/77A GB4229877A GB1589787A GB 1589787 A GB1589787 A GB 1589787A GB 42298/77 A GB42298/77 A GB 42298/77A GB 4229877 A GB4229877 A GB 4229877A GB 1589787 A GB1589787 A GB 1589787A
- Authority
- GB
- United Kingdom
- Prior art keywords
- spiro
- thiazolidine
- compound
- formula
- ethoxycarbonyl
- 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
- 239000000651 prodrug Substances 0.000 title claims description 12
- 229940002612 prodrug Drugs 0.000 title claims description 12
- 150000003431 steroids Chemical class 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 59
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 42
- 125000003003 spiro group Chemical group 0.000 claims description 42
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 30
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- -1 or substituted C 1-C Chemical group 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 229960000890 hydrocortisone Drugs 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 12
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 claims description 10
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 claims description 10
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 10
- 229960004544 cortisone Drugs 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 229960005205 prednisolone Drugs 0.000 claims description 9
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 229960004618 prednisone Drugs 0.000 claims description 8
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 238000009472 formulation Methods 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- 230000000699 topical effect Effects 0.000 claims description 7
- 241001465754 Metazoa Species 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000012876 carrier material Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- OVTZIJOGPKGLQV-BYZMTCBYSA-N (8s,9s,10r,13r,14s,17s)-17-ethyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1C=C2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 OVTZIJOGPKGLQV-BYZMTCBYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 206010061218 Inflammation Diseases 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 claims description 4
- FCYQTGCEDUOHLT-LEKSSAKUSA-N 1-[(8s,9s,10r,13s,14s,17s)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound C1C=C2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 FCYQTGCEDUOHLT-LEKSSAKUSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000002552 dosage form Substances 0.000 claims description 3
- LPNRQDKBYYAJQV-UDCWSGSHSA-N 1-[(8s,9s,10r,13s,14s,17s)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2,2,2-trihydroxyethanone Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)C(O)(O)O)[C@@H]4[C@@H]3CC=C21 LPNRQDKBYYAJQV-UDCWSGSHSA-N 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 2
- 239000007822 coupling agent Substances 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 230000001747 exhibiting effect Effects 0.000 claims description 2
- 239000001087 glyceryl triacetate Substances 0.000 claims description 2
- 235000013773 glyceryl triacetate Nutrition 0.000 claims description 2
- 230000028709 inflammatory response Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229960002622 triacetin Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 4
- AWYLBPYKIGVOEF-LEKSSAKUSA-N 1-[(8S,9S,10R,13S,14S,17S)-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound CC([C@H]1CC[C@H]2[C@@H]3CCC4=CCC=C[C@]4(C)[C@H]3CC[C@]12C)=O AWYLBPYKIGVOEF-LEKSSAKUSA-N 0.000 claims 2
- FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 claims 2
- 239000004615 ingredient Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 235000002639 sodium chloride Nutrition 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 210000003918 fraction a Anatomy 0.000 description 7
- 231100000252 nontoxic Toxicity 0.000 description 7
- 230000003000 nontoxic effect Effects 0.000 description 7
- 230000003637 steroidlike Effects 0.000 description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 230000009102 absorption Effects 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 4
- 150000007522 mineralic acids Chemical class 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 210000003491 skin Anatomy 0.000 description 4
- 125000001984 thiazolidinyl group Chemical group 0.000 description 4
- WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000002260 anti-inflammatory agent Substances 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
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- 229910052740 iodine Inorganic materials 0.000 description 3
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- ROGNGKQHZKVSIE-SWRQQMGTSA-N (8S,9S,10R,13R,14S,17S)-17-ethyl-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthrene-1,2,4-triol Chemical compound OC1=C(CC(=C2CC[C@H]3[C@@H]4CC[C@H](CC)[C@]4(CC[C@@H]3[C@@]12C)C)O)O ROGNGKQHZKVSIE-SWRQQMGTSA-N 0.000 description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- GTBJQKNDIKQBSL-MIBLLKTRSA-N 2-[(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl]ethane-1,1-diol Chemical compound C1C=C[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)CC(O)O)[C@@H]4[C@@H]3CCC2=C1 GTBJQKNDIKQBSL-MIBLLKTRSA-N 0.000 description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
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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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/005—Ketals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of only two carbon atoms, e.g. pregnane derivatives
-
- 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
- C07J43/006—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton spiro-condensed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Rheumatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Pain & Pain Management (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/731,373 US4069322A (en) | 1976-10-12 | 1976-10-12 | Pro-drugs for the improved delivery of certain selected anti-inflammatory steroids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1589787A true GB1589787A (en) | 1981-05-20 |
Family
ID=24939222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB42298/77A Expired GB1589787A (en) | 1976-10-12 | 1977-10-11 | Pro-drugs for certain steroids |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4069322A (enExample) |
| JP (1) | JPS5392753A (enExample) |
| AU (1) | AU513155B2 (enExample) |
| BE (1) | BE859613A (enExample) |
| CA (1) | CA1100482A (enExample) |
| DE (1) | DE2745948A1 (enExample) |
| FR (1) | FR2367777A1 (enExample) |
| GB (1) | GB1589787A (enExample) |
| SE (1) | SE433220B (enExample) |
| ZA (1) | ZA776014B (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4235887A (en) * | 1977-04-13 | 1980-11-25 | The Upjohn Company | Process for therapeutic treatment |
| US4221787A (en) * | 1978-03-28 | 1980-09-09 | Interx Research Corporation | Esteramide prodrugs of anti-inflammatory corticosteroids |
| US4279900A (en) * | 1978-07-13 | 1981-07-21 | Intrex Research Corporation | Prodrugs for the improved delivery of halogen-containing glucocorticosteroids |
| US4213978A (en) * | 1978-12-05 | 1980-07-22 | Interx Research Corporation | Anti-acne and anti-seborrhea prodrug derivatives of progesterone |
| US4268441A (en) * | 1979-03-13 | 1981-05-19 | Interx Research Corporation | Prodrugs for improved bioavailability of certain Δ4 -3-ketosteroidal sex hormones |
| ATE126695T1 (de) * | 1982-05-18 | 1995-09-15 | Univ Florida | Gehirnspezifische arzneimittelabgabe. |
| WO1984004041A1 (en) * | 1983-04-14 | 1984-10-25 | Univ California | Colon-specific drug delivery system |
| US5886162A (en) * | 1989-11-03 | 1999-03-23 | Research Foundation Of State University Of New York | Lipophilic diakylaminomethylene prodrug derivatives for the inhibition of replication of viruses |
| US5061700A (en) * | 1989-11-16 | 1991-10-29 | Gordon Jay Dow | Glyceryl acetate ointment vehicles |
| CN116023425B (zh) * | 2023-03-28 | 2023-06-20 | 南京师范大学 | 曲安西龙衍生物及其医药用途 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB959377A (en) * | 1959-10-12 | 1964-06-03 | Scherico Ltd | Dioxy steroids and processes for their preparation |
| CH432513A (de) * | 1961-06-13 | 1967-03-31 | Vismara Francesco Spa | Verfahren zur Herstellung neuer, 1'-substituierter 17a,21-(1'-Alkoxy)-methylendioxysteroide |
| US3119816A (en) * | 1961-12-19 | 1964-01-28 | Shionogi & Co | 2'-substituted thiazolo[5', 4'-16, 17] steroid of androstane series |
| GB1043347A (en) * | 1963-05-10 | 1966-09-21 | Glaxo Lab Ltd | 17,21-orthoesters of steroids |
| IT1056712B (it) * | 1967-04-01 | 1982-02-20 | Vismara F Spa | Derivati steroidali |
-
1976
- 1976-10-12 US US05/731,373 patent/US4069322A/en not_active Expired - Lifetime
-
1977
- 1977-10-07 ZA ZA00776014A patent/ZA776014B/xx unknown
- 1977-10-11 AU AU29572/77A patent/AU513155B2/en not_active Expired
- 1977-10-11 SE SE7711385A patent/SE433220B/xx not_active IP Right Cessation
- 1977-10-11 CA CA288,679A patent/CA1100482A/en not_active Expired
- 1977-10-11 GB GB42298/77A patent/GB1589787A/en not_active Expired
- 1977-10-12 BE BE2056332A patent/BE859613A/xx not_active IP Right Cessation
- 1977-10-12 JP JP12291277A patent/JPS5392753A/ja active Pending
- 1977-10-12 FR FR7730746A patent/FR2367777A1/fr active Granted
- 1977-10-12 DE DE19772745948 patent/DE2745948A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| CA1100482A (en) | 1981-05-05 |
| AU513155B2 (en) | 1980-11-20 |
| JPS5392753A (en) | 1978-08-15 |
| AU2957277A (en) | 1979-04-26 |
| FR2367777B1 (enExample) | 1980-10-17 |
| US4069322A (en) | 1978-01-17 |
| ZA776014B (en) | 1978-05-30 |
| FR2367777A1 (fr) | 1978-05-12 |
| DE2745948A1 (de) | 1978-04-13 |
| SE433220B (sv) | 1984-05-14 |
| SE7711385L (sv) | 1978-04-13 |
| BE859613A (fr) | 1978-02-01 |
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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 |
Effective date: 19931011 |