GB997167A - Improvements in or relating to steroids and the manufacture thereof - Google Patents
Improvements in or relating to steroids and the manufacture thereofInfo
- Publication number
- GB997167A GB997167A GB42687/61A GB4268761A GB997167A GB 997167 A GB997167 A GB 997167A GB 42687/61 A GB42687/61 A GB 42687/61A GB 4268761 A GB4268761 A GB 4268761A GB 997167 A GB997167 A GB 997167A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- hydroxy
- difluoromethyl
- bismethylenedioxy
- methyl
- 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
- 150000003431 steroids Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 carbonyl radical Chemical class 0.000 abstract 22
- 125000002252 acyl group Chemical group 0.000 abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract 8
- 239000001257 hydrogen Substances 0.000 abstract 8
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- 150000002431 hydrogen Chemical class 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 229930195733 hydrocarbon Natural products 0.000 abstract 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 abstract 3
- 239000000243 solution Substances 0.000 abstract 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 101100241859 Mus musculus Oacyl gene Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 150000005840 aryl radicals Chemical group 0.000 abstract 2
- 229940117975 chromium trioxide Drugs 0.000 abstract 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 abstract 2
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 abstract 2
- 239000011737 fluorine Substances 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 235000019253 formic acid Nutrition 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 230000001590 oxidative effect Effects 0.000 abstract 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- LEFWXNMOYZJRBM-NMKBPFOZSA-N (8s,10s,13r,14s,17s)-17-ethyl-10,13-dimethyl-2,3,6,7,8,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthrene Chemical class C1CC[C@]2(C)C3=CC[C@]4(C)[C@@H](CC)CC[C@H]4[C@@H]3CCC2=C1 LEFWXNMOYZJRBM-NMKBPFOZSA-N 0.000 abstract 1
- WILIRDQOEMCACO-BYZMTCBYSA-N (8s,9s,10r,13r,14s,17s)-17-ethyl-10,13-dimethyl-8,9,11,12,14,15,16,17-octahydro-3h-cyclopenta[a]phenanthrene Chemical compound C1=CC2=CCC=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 WILIRDQOEMCACO-BYZMTCBYSA-N 0.000 abstract 1
- 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 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- 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 abstract 1
- IIUZTXTZRGLYTI-UHFFFAOYSA-N Dihydrogriseofulvin Natural products COC1CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 IIUZTXTZRGLYTI-UHFFFAOYSA-N 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004593 Epoxy Substances 0.000 abstract 1
- UXWOXTQWVMFRSE-UHFFFAOYSA-N Griseoviridin Natural products O=C1OC(C)CC=C(C(NCC=CC=CC(O)CC(O)C2)=O)SCC1NC(=O)C1=COC2=N1 UXWOXTQWVMFRSE-UHFFFAOYSA-N 0.000 abstract 1
- DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 abstract 1
- 229930193140 Neomycin Natural products 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
- 239000004133 Sodium thiosulphate Substances 0.000 abstract 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 230000001974 anti-anabolic effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 229940121375 antifungal agent Drugs 0.000 abstract 1
- 239000003429 antifungal agent Substances 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 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
- 239000010941 cobalt Substances 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 229960004544 cortisone Drugs 0.000 abstract 1
- 239000006071 cream Substances 0.000 abstract 1
- 238000005695 dehalogenation reaction Methods 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- 150000002085 enols Chemical class 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 abstract 1
- 229960002867 griseofulvin Drugs 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000006210 lotion Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 244000005700 microbiome Species 0.000 abstract 1
- HBPXFHNNLMCUPA-UHFFFAOYSA-M molport-023-277-200 Chemical group [Br-].C1N(C2)CN3CN2C[N+]1(CCO)C3 HBPXFHNNLMCUPA-UHFFFAOYSA-M 0.000 abstract 1
- 229960004927 neomycin Drugs 0.000 abstract 1
- 229960002950 novobiocin Drugs 0.000 abstract 1
- YJQPYGGHQPGBLI-KGSXXDOSSA-M novobiocin(1-) 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-M 0.000 abstract 1
- 239000002674 ointment Substances 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 150000002960 penicillins Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000001817 pituitary effect Effects 0.000 abstract 1
- 235000003270 potassium fluoride Nutrition 0.000 abstract 1
- 239000011698 potassium fluoride Substances 0.000 abstract 1
- 230000001072 progestational effect Effects 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 230000001105 regulatory effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 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
- 239000012279 sodium borohydride Substances 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
- 235000009518 sodium iodide Nutrition 0.000 abstract 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 abstract 1
- 235000019345 sodium thiosulphate Nutrition 0.000 abstract 1
- 239000007921 spray Substances 0.000 abstract 1
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 abstract 1
- OFVLGDICTFRJMM-WESIUVDSSA-N tetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O OFVLGDICTFRJMM-WESIUVDSSA-N 0.000 abstract 1
- 229930101283 tetracycline Natural products 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- 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
-
- 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
- C07J75/00—Processes for the preparation of steroids in general
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/886—Streptomyces
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80523A US3251834A (en) | 1961-01-04 | 1961-01-04 | Process for the production of 6-difluoro methyl hydrocortisone and intermediates obtaned therefrom |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB997167A true GB997167A (en) | 1965-07-07 |
Family
ID=22157930
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB997168D Active GB997168A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1961-01-04 | ||
| GB42687/61A Expired GB997167A (en) | 1961-01-04 | 1961-11-29 | Improvements in or relating to steroids and the manufacture thereof |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB997168D Active GB997168A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1961-01-04 |
Country Status (3)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3440252A (en) * | 1965-06-23 | 1969-04-22 | Glaxo Lab Ltd | Preparation of 21-deoxy steroids |
-
0
- GB GB997168D patent/GB997168A/en active Active
-
1961
- 1961-01-04 US US80523A patent/US3251834A/en not_active Expired - Lifetime
- 1961-11-29 GB GB42687/61A patent/GB997167A/en not_active Expired
- 1961-12-08 CH CH1429561A patent/CH402854A/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB997168A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| US3251834A (en) | 1966-05-17 |
| CH402854A (de) | 1965-11-30 |
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