GB1026501A - Improvements in or relating to steroids and the manufacture thereof - Google Patents
Improvements in or relating to steroids and the manufacture thereofInfo
- Publication number
- GB1026501A GB1026501A GB38760/62A GB3876062A GB1026501A GB 1026501 A GB1026501 A GB 1026501A GB 38760/62 A GB38760/62 A GB 38760/62A GB 3876062 A GB3876062 A GB 3876062A GB 1026501 A GB1026501 A GB 1026501A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloro
- dione
- pregnadiene
- acylate
- trihydroxy
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000003431 steroids Chemical class 0.000 title 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 4
- 229910052731 fluorine Chemical group 0.000 abstract 4
- 239000011737 fluorine Chemical group 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000002252 acyl group Chemical group 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 abstract 3
- 239000003826 tablet Substances 0.000 abstract 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 abstract 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 abstract 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 2
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- -1 hydrocarbon carboxylic acid Chemical class 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 abstract 2
- SITPHKYOZLUNHQ-ROVFHEEESA-N (8S,9S,10R,13S,14S,16R,17S)-16-chloro-17-(2-iodoacetyl)-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound ICC([C@H]1[C@@H](C[C@H]2[C@@H]3CCC4=CC(C=C[C@]4(C)[C@H]3CC[C@]12C)=O)Cl)=O SITPHKYOZLUNHQ-ROVFHEEESA-N 0.000 abstract 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 abstract 1
- 108010001478 Bacitracin Proteins 0.000 abstract 1
- 229910000014 Bismuth subcarbonate Inorganic materials 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 101100241859 Mus musculus Oacyl gene Chemical group 0.000 abstract 1
- YJQPYGGHQPGBLI-UHFFFAOYSA-N Novobiocin Natural products O1C(C)(C)C(OC)C(OC(N)=O)C(O)C1OC1=CC=C(C(O)=C(NC(=O)C=2C=C(CC=C(C)C)C(O)=CC=2)C(=O)O2)C2=C1C YJQPYGGHQPGBLI-UHFFFAOYSA-N 0.000 abstract 1
- 229930182555 Penicillin Natural products 0.000 abstract 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 abstract 1
- 108010040201 Polymyxins Proteins 0.000 abstract 1
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 abstract 1
- 239000004098 Tetracycline Substances 0.000 abstract 1
- 229960001138 acetylsalicylic acid Drugs 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 abstract 1
- 229910021502 aluminium hydroxide Inorganic materials 0.000 abstract 1
- 229940035676 analgesics Drugs 0.000 abstract 1
- 229940069428 antacid Drugs 0.000 abstract 1
- 239000003159 antacid agent Substances 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 235000010323 ascorbic acid Nutrition 0.000 abstract 1
- 229960005070 ascorbic acid Drugs 0.000 abstract 1
- 239000011668 ascorbic acid Substances 0.000 abstract 1
- 229960003071 bacitracin Drugs 0.000 abstract 1
- 229930184125 bacitracin Natural products 0.000 abstract 1
- CLKOFPXJLQSYAH-ABRJDSQDSA-N bacitracin A Chemical compound C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2N=CNC=2)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 CLKOFPXJLQSYAH-ABRJDSQDSA-N 0.000 abstract 1
- 229960005274 benzocaine Drugs 0.000 abstract 1
- MGLUJXPJRXTKJM-UHFFFAOYSA-L bismuth subcarbonate Chemical compound O=[Bi]OC(=O)O[Bi]=O MGLUJXPJRXTKJM-UHFFFAOYSA-L 0.000 abstract 1
- 229940036358 bismuth subcarbonate Drugs 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 229910000019 calcium carbonate Inorganic materials 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 229960005091 chloramphenicol Drugs 0.000 abstract 1
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 abstract 1
- 239000000460 chlorine Chemical group 0.000 abstract 1
- 229910052801 chlorine Chemical group 0.000 abstract 1
- 239000006071 cream Substances 0.000 abstract 1
- 230000003111 delayed effect Effects 0.000 abstract 1
- PPQREHKVAOVYBT-UHFFFAOYSA-H dialuminum;tricarbonate Chemical compound [Al+3].[Al+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O PPQREHKVAOVYBT-UHFFFAOYSA-H 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000012055 enteric layer Substances 0.000 abstract 1
- 229960003276 erythromycin Drugs 0.000 abstract 1
- 239000003862 glucocorticoid Substances 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 230000000640 hydroxylating effect Effects 0.000 abstract 1
- 230000033444 hydroxylation Effects 0.000 abstract 1
- 238000005805 hydroxylation reaction Methods 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000003589 local anesthetic agent Substances 0.000 abstract 1
- 229960005015 local anesthetics Drugs 0.000 abstract 1
- 239000006210 lotion Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229960002950 novobiocin Drugs 0.000 abstract 1
- YJQPYGGHQPGBLI-KGSXXDOSSA-N novobiocin Chemical compound O1C(C)(C)[C@H](OC)[C@@H](OC(N)=O)[C@@H](O)[C@@H]1OC1=CC=C(C(O)=C(NC(=O)C=2C=C(CC=C(C)C)C(O)=CC=2)C(=O)O2)C2=C1C YJQPYGGHQPGBLI-KGSXXDOSSA-N 0.000 abstract 1
- 239000002674 ointment Substances 0.000 abstract 1
- 150000001451 organic peroxides Chemical class 0.000 abstract 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 abstract 1
- 239000012285 osmium tetroxide Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 229940049954 penicillin Drugs 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000006187 pill Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 229960004919 procaine Drugs 0.000 abstract 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 abstract 1
- 229960000581 salicylamide Drugs 0.000 abstract 1
- 229940096017 silver fluoride Drugs 0.000 abstract 1
- REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical compound [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 abstract 1
- BOYYFZLRUNZGFW-UHFFFAOYSA-M silver;dihydrogen phosphate Chemical compound [Ag+].OP(O)([O-])=O BOYYFZLRUNZGFW-UHFFFAOYSA-M 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- 235000009518 sodium iodide Nutrition 0.000 abstract 1
- 229960004025 sodium salicylate Drugs 0.000 abstract 1
- 235000010269 sulphur dioxide Nutrition 0.000 abstract 1
- 239000004291 sulphur dioxide Substances 0.000 abstract 1
- 239000006188 syrup Substances 0.000 abstract 1
- 235000020357 syrup Nutrition 0.000 abstract 1
- 229960002372 tetracaine Drugs 0.000 abstract 1
- GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 abstract 1
- 235000019364 tetracycline Nutrition 0.000 abstract 1
- 229940040944 tetracyclines Drugs 0.000 abstract 1
- 150000003522 tetracyclines Chemical class 0.000 abstract 1
- 229940088594 vitamin Drugs 0.000 abstract 1
- 235000013343 vitamin Nutrition 0.000 abstract 1
- 239000011782 vitamin Substances 0.000 abstract 1
- 229930003231 vitamin Natural products 0.000 abstract 1
- 235000019156 vitamin B Nutrition 0.000 abstract 1
- 239000011720 vitamin B Substances 0.000 abstract 1
- 229940046001 vitamin b complex Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (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)
Abstract
The invention comprises 16a -chloro steriods of the structural formula <FORM:1026501/C2/1> wherein R is hydroxyl, OAcyl or -OPO3H, the term Acyl representing the acyl radical of a hydrocarbon carboxylic acid containing from 1-12 carbon atoms, inclusive, R1 is an alkyl or aryl organic sulphonyl radical, X is hydrogen or fluorine, X1 is bromine or chlorine, Y is hydrogen, methyl or fluorine and processes for the preparation thereof by oxidatively hydroxylating an 11b -hydroxy-16a -chloro-21-acyloxy-1,4,17 (20-pregnatriene-3-one to produce 11b , 17a ,21-trihydroxy-16a -chloro-1,4-pregnadiene-3,20-dione 21-acylate III, dehydrating III with an N-haloacylamide and sulphur dioxide to form a 17a ,21-dihydroxy-16a -chloro-1,4,9(11)-pregnatriene-3,20 -dione 21-acylate IV, treating IV with an N-haloacylamide to form the corresponding 11b ,17a ,21 - trihydroxy - 9a - chloro-, bromo- or iodo-16a -chloro-1,4-pregnadiene-3,20-dione 21-acylate V; treating V with a mild base such as sodium acetate to form a 9b ,11b -oxido-17a ,21 -dihydroxy-16a -chloro-1,4-pregnadiene-3,20-dione 21-acylate VI, and treating VI with HF to form a 9a -fluoro-11b ,17a ,21-trihydroxy-16a - chloro - 1,4 - pregnadiene - 3,20 - dione 21-acylate. The oxidative hydroxylation may be effected with osmium tetroxide and an organic peroxide or an aryliodoso acetate. The 21-hydroxy compounds so obtained may be converted into the corresponding 21-sulphonyloxy compounds by means of an organic sulphonyl halide, which on further treatment with sodium or potassium iodide yield the corresponding 21-iodo compound. The 21-iodo compounds on treatment with silver dihydrogen phosphate gives 16a - chloro - 11b ,17a ,21 - trihydroxy - 1,4- pregnadiene - 3,20 - dione - 21 - dihydrogen phosphate which may be esterified in 17-position, or with silver fluoride 16a -chloro-21-fluoro-11b , 17a -dihydroxy-1,4-pregnadiene-3,20-dione is obtained.ALSO:Pharmaceutical compositions having anti-inflammatory and glucocorticoid activity and containing compounds having the formula <FORM:1026501/A5-A6/1> (wherein R is hydroxyl, O Acyl or OPO3H2, the term acyl representing the acyl radical of an organic carboxylic acid having 1-12 carbon atoms inclusive; X is hydrogen or fluorine and Y is hydrogen methyl or fluorine) are administered orally in pills, tablets, capsules, syrups elixirs, powders and granules, parenterally in sterile liquid form or topically in the forms of ointments, creams and lotions with or without coacting antibiotics e.g. chloramphenicol, penicillin, tetracyclines, erythromycin, novobiocin, polymyxin and bacitracin; analgesics e.g. aspirin, sodium salicylate, N-acetyl-p-aminophenol and salicylamide; amphetamines and tranquillizers; local anesthetics e.g. benzocaine, procaine and tetracaine; antacids, such as calcium carbonate, aluminium hydroxide, basic aluminium carbonate and bismuth subcarbonate; and the vitamins e.g. ascorbic acid and the Vitamin B-complex. The tablets can be laminated to form an inner-dosage and an outer-dosage component separated by an enteric layer thereby obtaining a delayed release. Alternatively the two components system can be utilized for preparing tablets containing incompatible ingredients.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US144830A US3137712A (en) | 1961-10-13 | 1961-10-13 | 16alpha-chloro-1, 4-pregnadienes |
| US20240362A | 1962-06-14 | 1962-06-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1026501A true GB1026501A (en) | 1966-04-20 |
Family
ID=26842402
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB38760/62A Expired GB1026501A (en) | 1961-10-13 | 1962-10-12 | Improvements in or relating to steroids and the manufacture thereof |
| GB49713/65A Expired GB1026503A (en) | 1961-10-13 | 1962-10-12 | Improvements in or relating to steroids and the manufacture thereof |
| GB49712/65A Expired GB1026502A (en) | 1961-10-13 | 1962-10-12 | Improvements in or relating to steroids and the manufacture thereof |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB49713/65A Expired GB1026503A (en) | 1961-10-13 | 1962-10-12 | Improvements in or relating to steroids and the manufacture thereof |
| GB49712/65A Expired GB1026502A (en) | 1961-10-13 | 1962-10-12 | Improvements in or relating to steroids and the manufacture thereof |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR2260M (en) |
| GB (3) | GB1026501A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19715594A1 (en) | 1997-04-15 | 1998-10-22 | Bayer Ag | Analgesic combination |
-
1962
- 1962-10-12 GB GB38760/62A patent/GB1026501A/en not_active Expired
- 1962-10-12 GB GB49713/65A patent/GB1026503A/en not_active Expired
- 1962-10-12 GB GB49712/65A patent/GB1026502A/en not_active Expired
-
1963
- 1963-01-11 FR FR921196A patent/FR2260M/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| FR2260M (en) | 1964-01-06 |
| GB1026503A (en) | 1966-04-20 |
| GB1026502A (en) | 1966-04-20 |
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