DE1618993B1 - Verfahren zur Herstellung von 3-(2'-Chloräthylthio)-6-formyl-steroiden - Google Patents
Verfahren zur Herstellung von 3-(2'-Chloräthylthio)-6-formyl-steroidenInfo
- Publication number
- DE1618993B1 DE1618993B1 DE1967S0113470 DES0113470A DE1618993B1 DE 1618993 B1 DE1618993 B1 DE 1618993B1 DE 1967S0113470 DE1967S0113470 DE 1967S0113470 DE S0113470 A DES0113470 A DE S0113470A DE 1618993 B1 DE1618993 B1 DE 1618993B1
- Authority
- DE
- Germany
- Prior art keywords
- chloroethylthio
- formyl
- acetate
- pregnadiene
- fluoro
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- CLTOGOPSCZSYGS-CLWFVZRMSA-N ClCCSC1=CC2=CC[C@H]3[C@@H]4CC[C@H](CC)[C@]4(CC[C@@H]3[C@]2(CC1)C)C Chemical compound ClCCSC1=CC2=CC[C@H]3[C@@H]4CC[C@H](CC)[C@]4(CC[C@@H]3[C@]2(CC1)C)C CLTOGOPSCZSYGS-CLWFVZRMSA-N 0.000 claims description 3
- 239000003377 acid catalyst Substances 0.000 claims description 3
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000012320 chlorinating reagent Substances 0.000 claims description 3
- AYGFEWYXKDFVIQ-NWSAAYAGSA-N pregn-4-en-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 AYGFEWYXKDFVIQ-NWSAAYAGSA-N 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 4
- DHYMIGDMHYMJAQ-BYZMTCBYSA-N (8s,9s,10r,13r,14s,17s)-17-ethyl-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1C=C2C=CCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 DHYMIGDMHYMJAQ-BYZMTCBYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 150000003431 steroids Chemical class 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000002354 daily effect Effects 0.000 description 2
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 2
- 229960003957 dexamethasone Drugs 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 230000003203 everyday effect Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 1
- ITHKUADHDKZENI-UHFFFAOYSA-N 2-chloroethanethiol Chemical compound SCCCl ITHKUADHDKZENI-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010010741 Conjunctivitis Diseases 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 241000021559 Dicerandra Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 235000010654 Melissa officinalis Nutrition 0.000 description 1
- 206010029164 Nephrotic syndrome Diseases 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 206010014801 endophthalmitis Diseases 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- FJLHLDBEZKTSOK-UHFFFAOYSA-N n-ethyl-n-methylformamide Chemical compound CCN(C)C=O FJLHLDBEZKTSOK-UHFFFAOYSA-N 0.000 description 1
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 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
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
-
- 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)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3164666 | 1966-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1618993B1 true DE1618993B1 (de) | 1971-08-26 |
Family
ID=11234208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1967S0113470 Pending DE1618993B1 (de) | 1966-12-29 | 1967-12-22 | Verfahren zur Herstellung von 3-(2'-Chloräthylthio)-6-formyl-steroiden |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3480623A (enExample) |
| AT (1) | AT273393B (enExample) |
| BE (1) | BE708699A (enExample) |
| CH (1) | CH493510A (enExample) |
| DE (1) | DE1618993B1 (enExample) |
| DK (1) | DK116656B (enExample) |
| ES (1) | ES348727A1 (enExample) |
| FR (2) | FR1549032A (enExample) |
| GB (1) | GB1161629A (enExample) |
| IL (1) | IL29198A (enExample) |
| NL (1) | NL6717123A (enExample) |
| SE (1) | SE329154B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA04003865A (es) * | 2001-10-26 | 2004-07-08 | Upjohn Co | Compuestos de amonio cuaternario y sus usos como agentes antimuscarinicos. |
| JP2005511582A (ja) * | 2001-11-05 | 2005-04-28 | ファルマシア アンド アップジョン カンパニー リミティド ライアビリティー カンパニー | 抗ムスカリン・エアゾール |
| TW200412945A (en) * | 2002-10-25 | 2004-08-01 | Upjohn Co | Quaternary ammonium compounds |
| US20040242569A1 (en) * | 2003-04-15 | 2004-12-02 | Pfizer Inc. | Quatemary ammonium compounds |
| WO2004091597A2 (en) * | 2003-04-15 | 2004-10-28 | Pharmacia & Upjohn Company Llc | Method of treating irritable bowel syndrome (ibs) |
| MXPA05011225A (es) * | 2003-04-18 | 2005-12-14 | Pharmacia & Upjohn Co Llc | Politerapias. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3364236A (en) * | 1962-12-14 | 1968-01-16 | Merck & Co Inc | 3-keto-delta4-unsaturated-6-formyl steroids and process for the production thereof |
-
1967
- 1967-12-15 NL NL6717123A patent/NL6717123A/xx unknown
- 1967-12-22 FR FR1549032D patent/FR1549032A/fr not_active Expired
- 1967-12-22 DE DE1967S0113470 patent/DE1618993B1/de active Pending
- 1967-12-22 DK DK648967AA patent/DK116656B/da unknown
- 1967-12-22 GB GB58529/67A patent/GB1161629A/en not_active Expired
- 1967-12-22 IL IL29198A patent/IL29198A/xx unknown
- 1967-12-26 US US693096A patent/US3480623A/en not_active Expired - Lifetime
- 1967-12-26 FR FR133692A patent/FR8359M/fr not_active Expired
- 1967-12-27 SE SE17808/67A patent/SE329154B/xx unknown
- 1967-12-28 BE BE708699D patent/BE708699A/xx unknown
- 1967-12-28 CH CH1825267A patent/CH493510A/de not_active IP Right Cessation
- 1967-12-28 ES ES348727A patent/ES348727A1/es not_active Expired
- 1967-12-28 AT AT1174567A patent/AT273393B/de active
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1161629A (en) | 1969-08-13 |
| BE708699A (enExample) | 1968-06-28 |
| FR1549032A (enExample) | 1968-12-06 |
| ES348727A1 (es) | 1969-03-16 |
| IL29198A (en) | 1972-11-28 |
| US3480623A (en) | 1969-11-25 |
| DK116656B (da) | 1970-02-02 |
| NL6717123A (enExample) | 1968-07-01 |
| AT273393B (de) | 1969-08-11 |
| CH493510A (de) | 1970-07-15 |
| FR8359M (enExample) | 1971-02-08 |
| SE329154B (enExample) | 1970-10-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2707336C2 (enExample) | ||
| DE1443958B1 (de) | 9 alpha-Chlor- bzw. 9 alpha-Fluor-16 beta-methyl-prednisolon-17-monoester und ein Verfahren zu deren Herstellung | |
| EP0072547B1 (de) | Neue 6-alpha-Methylprednisolon-Derivate ihre Herstellung und Verwendung | |
| EP0110041A1 (de) | Neue 6alpha-Methylkortikoide, ihre Herstellung und Verwendung | |
| DE1618065B2 (de) | 21-oxo-23-desoxo-cardenolide, verfahren zu deren herstellung und daraus hergestellte arzneimittel | |
| DE1618993B1 (de) | Verfahren zur Herstellung von 3-(2'-Chloräthylthio)-6-formyl-steroiden | |
| DE1618993C (de) | Verfahren zur Herstellung von 3-(2-Chloräthylthio)-6-formyl-steroiden | |
| DE2852055C2 (enExample) | ||
| DE2162592A1 (de) | Steroide der 5 alpha-Pregnan-Reihen | |
| DE3116891A1 (de) | Steroid-oxazole | |
| DE1188079B (de) | Verfahren zur Herstellung von 17alpha, 21-Dioxysteroiden | |
| DE1493072C (de) | Neue 3 (omega Halogenalkoxy) 6 formyl Delta hoch 3,5 pregnadienverbindungen | |
| DE1668661C3 (de) | 6-Cyansteroide und Verfahren zu deren Herstellung | |
| DE1493178C3 (de) | 6 alpha-Fluor-16 alpha-methyl-1,4pregnadien-3,20-dion-derivate und Verfahren zu ihrer Herstellung | |
| DE1793606C (de) | Verfahren zur Herstellung von 3 (omega-Halogenalkoxy)-6-formyl-Delta hoch 3,5 -pregnadienverbindungen. Ausscheidung aus: 1493072 | |
| DE1921462C3 (de) | Steroid oxazoline, Verfahren zu deren Herstellung und dieselben ent haltende Arzneimittel | |
| DE1468893A1 (de) | Verfahren zur Herstellung von 21-Estern von Pregnanderivaten | |
| DE1643016C3 (de) | 1,2alpha-Methylensteroide, Verfahren zu deren Herstellung und diese Steroide enthaltende Mittel | |
| DE1802962C3 (de) | Neue Galpha, 6beta-Dlfluorsteroide, Verfahren zu ihrer Herstellung, sowie diese enthaltende Mittel | |
| DE1768673B1 (de) | 6alpha,9alpha-Difluorprednisolon-17,21-diester | |
| AT232659B (de) | Verfahren zur Herstellung neuer Steroidverbindungen | |
| DE1793461A1 (de) | 21-(Cyclobutyl-carbonsaeure)-ester von Steroidderivaten und Verfahren zu ihrer Herstellung | |
| AT292210B (de) | Verfahren zur Herstellung von neuen in 2-Stellung durch Chlor substituierten Steroiden der Pregnanreihe | |
| DE1418320C (de) | Verfahren zur Herstellung von 16 alpha-Methyl- 1,4-pregnadien-17 alpha, 21-diol-3,11,20-trion und von entsprechenden 21niedermolekularen Alkansäureestern desselben | |
| DE1568972C (de) | Pregna 1,4 dien 9alpha, 1 lbeta dichlor 3,20 dion eckige Klammer auf 17alpha, 16 alpha d eckige Klammer zu 2'methyloxazoline |