DE823593C - Verfahren zur Herstellung von Anhydro-corticosteronen und ihren Estern - Google Patents
Verfahren zur Herstellung von Anhydro-corticosteronen und ihren EsternInfo
- Publication number
- DE823593C DE823593C DEC52A DEC0000052A DE823593C DE 823593 C DE823593 C DE 823593C DE C52 A DEC52 A DE C52A DE C0000052 A DEC0000052 A DE C0000052A DE 823593 C DE823593 C DE 823593C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- esters
- anhydro
- production
- parts
- 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
- 150000002148 esters Chemical class 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical class O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical compound [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000005283 haloketone group Chemical group 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical class [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- -1 carboxylic acid halides Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 102000001554 Hemoglobins Human genes 0.000 description 1
- 108010054147 Hemoglobins Proteins 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- DNKYMRIVXIQCFO-UHFFFAOYSA-N benzene pentane Chemical compound CCCCC.CCCCC.C1=CC=CC=C1 DNKYMRIVXIQCFO-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 229960004486 desoxycorticosterone acetate Drugs 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 150000003124 pregnadienes Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH281597T | 1948-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE823593C true DE823593C (de) | 1951-12-06 |
Family
ID=4483238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC52A Expired DE823593C (de) | 1948-11-30 | 1949-10-23 | Verfahren zur Herstellung von Anhydro-corticosteronen und ihren Estern |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH281597A (enrdf_load_stackoverflow) |
| DE (1) | DE823593C (enrdf_load_stackoverflow) |
| FR (1) | FR1000391A (enrdf_load_stackoverflow) |
| GB (1) | GB665585A (enrdf_load_stackoverflow) |
| NL (1) | NL71753C (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE957030C (de) * | 1952-01-21 | 1957-01-31 | Organon Nv | Verfahren zur Herstellung der Phenylpropionsaeureester von Steroidhormonen |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2984556A (en) * | 1954-03-19 | 1961-05-16 | Shell Oil Co | Fuel composition and process for its manufacture |
| US3009935A (en) * | 1954-10-29 | 1961-11-21 | Merck & Co Inc | 4, 9(11)-pregnadien-17alpha-ol-3, 20-dione compounds and process therefor |
-
1948
- 1948-11-30 CH CH281597D patent/CH281597A/de unknown
-
1949
- 1949-10-23 DE DEC52A patent/DE823593C/de not_active Expired
- 1949-10-28 NL NL149626A patent/NL71753C/xx active
- 1949-11-25 GB GB30298/49A patent/GB665585A/en not_active Expired
- 1949-11-28 FR FR1000391D patent/FR1000391A/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE957030C (de) * | 1952-01-21 | 1957-01-31 | Organon Nv | Verfahren zur Herstellung der Phenylpropionsaeureester von Steroidhormonen |
Also Published As
| Publication number | Publication date |
|---|---|
| NL71753C (enrdf_load_stackoverflow) | 1953-02-16 |
| CH281597A (de) | 1952-03-15 |
| FR1000391A (fr) | 1952-02-11 |
| GB665585A (en) | 1952-01-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1244777B (de) | Verfahren zur Herstellung von 7alpha-Methyl-16alpha-hydroxy-oestron bzw. -3, 16-diacetat | |
| DE823593C (de) | Verfahren zur Herstellung von Anhydro-corticosteronen und ihren Estern | |
| DE1131665B (de) | Verfahren zur Herstellung von Aminosteroidverbindungen | |
| DE883897C (de) | Verfahren zur Herstellung von 17-(ª‡)-Oxy-20-ketopregnanen | |
| DE897704C (de) | Verfahren zur Herstellung von A4,5;16,17-Pregna-dien-ol-(21)-dion-(3,20)-Abkoemmlingen | |
| DE825408C (de) | Verfahren zur Herstellung von 7-Dehydrothiosterinen und ihren Derivaten | |
| AT253704B (de) | Verfahren zur Herstellung des neuen 7α-Methyl-16α-hydroxy-östrons und seines 3, 16-Diacetates | |
| CH286366A (de) | Verfahren zur Herstellung eines Anhydro-corticosterons. | |
| AT233176B (de) | Verfahren zur Herstellung neuer 21-Halbester von im Ring A ungesättigten 3, 20-Dioxo-21-hydroxypregnanverbindungen | |
| DE855264C (de) | Verfahren zur Herstellung von Acylaminodiolen | |
| DE940587C (de) | Verfahren zur Herstellung von in 7 (8)-Stellung ungesaettigten 11-Ketosteroiden bzw.von in 8 (9)-Stellung ungesaettigten 11-Ketosteroiden | |
| EP0011121A1 (de) | Hydrocortisonester, diese enthaltende pharmazeutische Zubereitungen und Verfahren zu ihrer Herstellung | |
| AT240540B (de) | Verfahren zur Herstellung von 4-Chlor-Δ<4>-3-ketosteroidverbindungen | |
| AT257849B (de) | Verfahren zur Herstellung von neuen 20-Oxo-21-hydroxy-16, 21-methano-Δ<21>-steroiden | |
| DE1468554C (de) | 20 beta tert Amino 3 alpha hydroxy (bzw acyloxy) 5 beta pregnane bzw de ren Salze sowie Verfahren zu ihrer Her stellung | |
| DEC0000052MA (de) | Verfahren zur Herstellung von Anhydro-corticosteronen und ihren Estern | |
| DE973365C (de) | Verfahren zur Herstellung von Cortison und Hydrocortison | |
| DE965637C (de) | Verfahren zur Herstellung von 19-Nortestosteron-17-acylaten und bzw. oder deren 3-Enolacylaten | |
| AT209007B (de) | Verfahren zur Herstellung von 9 α-Halogen-4-pregnen-16 α, 17 α,21-triol-3, 11, 20-trionen und ihren Estern | |
| AT235475B (de) | Verfahren zur Herstellung neuer, wasserlöslicher, therapeutisch verwendbarer Salze des Hydrocortisons | |
| DE1468919C (de) | 3,11 Dioxo steroid 4,9 diene und ein Verfahren zu ihrer Herstellung | |
| AT274260B (de) | Verfahren zur Herstellung von neuen 21-Fluor-Δ<4,6>-pregnadienen | |
| AT213898B (de) | Verfahren zur Herstellung des neuen 3-p-Amino-benzolsulfonamido-6-oxy-pyridazins und seiner Salze | |
| DE1101415B (de) | Verfahren zur Herstellung von 6ª‡-Methyl-17ª‡-acetoxy-4-pregnen-3, 20-dion | |
| CH396883A (de) | Verfahren zur Herstellung neuer Hydrazone |