HU183182B - Process for preparing steroid hormones with pregnane skeleton - Google Patents
Process for preparing steroid hormones with pregnane skeleton Download PDFInfo
- Publication number
- HU183182B HU183182B HU801791A HU179180A HU183182B HU 183182 B HU183182 B HU 183182B HU 801791 A HU801791 A HU 801791A HU 179180 A HU179180 A HU 179180A HU 183182 B HU183182 B HU 183182B
- Authority
- HU
- Hungary
- Prior art keywords
- group
- salt
- protecting
- dione
- temperature
- Prior art date
Links
- 239000003270 steroid hormone Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 3
- JWMFYGXQPXQEEM-WZBAXQLOSA-N pregnane group Chemical group [C@@H]12CC[C@H](CC)[C@@]1(C)CC[C@H]1[C@H]2CCC2CCCC[C@]12C JWMFYGXQPXQEEM-WZBAXQLOSA-N 0.000 title description 3
- 230000000813 microbial effect Effects 0.000 claims abstract description 10
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 10
- 230000021736 acetylation Effects 0.000 claims description 8
- 238000006640 acetylation reaction Methods 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 150000003431 steroids Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 230000031709 bromination Effects 0.000 claims description 3
- 238000005893 bromination reaction Methods 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 238000002329 infrared spectrum Methods 0.000 claims description 2
- 230000000397 acetylating effect Effects 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 239000011833 salt mixture Substances 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 12
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 9
- 238000005805 hydroxylation reaction Methods 0.000 abstract description 8
- 230000033444 hydroxylation Effects 0.000 abstract description 6
- 238000009835 boiling Methods 0.000 abstract description 5
- -1 enamine salt Chemical class 0.000 abstract description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract description 3
- 239000002184 metal Substances 0.000 abstract 2
- JYGXADMDTFJGBT-KZUKIWJVSA-N (8s,9s,10r,13s,14s,17r)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-3-one 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 JYGXADMDTFJGBT-KZUKIWJVSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- VZCSUCBQWVHBED-KIWLAIFZSA-N CC(=O)OCC(=O)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC(O)[C@]4(C)[C@H]3CC[C@]12C Chemical compound CC(=O)OCC(=O)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC(O)[C@]4(C)[C@H]3CC[C@]12C VZCSUCBQWVHBED-KIWLAIFZSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 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
- 150000002081 enamines Chemical class 0.000 abstract 1
- 229960002899 hydroxyprogesterone Drugs 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HPAKILCZTKWIFK-JZTHCNPZSA-N [2-[(8r,9s,10r,13s,14s,17r)-17-hydroxy-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)CC2 HPAKILCZTKWIFK-JZTHCNPZSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- IJWRHVPBIVEEQB-OBQKJFGGSA-N (8r,9s,10r,13s,14s,17r)-17-(2-bromoacetyl)-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@@](CC4)(O)C(=O)CBr)[C@@H]4[C@@H]3CCC2=C1 IJWRHVPBIVEEQB-OBQKJFGGSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 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 description 2
- 239000000543 intermediate Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- DBPWSSGDRRHUNT-UHFFFAOYSA-N 17alpha-hydroxy progesterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C(=O)C)(O)C1(C)CC2 DBPWSSGDRRHUNT-UHFFFAOYSA-N 0.000 description 1
- JWMFYGXQPXQEEM-NUNROCCHSA-N 5β-pregnane Chemical compound C([C@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](CC)[C@@]2(C)CC1 JWMFYGXQPXQEEM-NUNROCCHSA-N 0.000 description 1
- VHRSUDSXCMQTMA-UWKORSIYSA-N 6-methylprednisolone Chemical compound C([C@@]12C)=CC(=O)C=C1C(C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)CO)CC[C@H]21 VHRSUDSXCMQTMA-UWKORSIYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DOMWKUIIPQCAJU-LJHIYBGHSA-N Hydroxyprogesterone caproate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)CCCCC)[C@@]1(C)CC2 DOMWKUIIPQCAJU-LJHIYBGHSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical group [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical group C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007350 electrophilic reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229950000801 hydroxyprogesterone caproate Drugs 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- 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 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BG7945363A BG29777A1 (en) | 1979-07-24 | 1979-07-24 | Method for obtaining of steroid hormons with preguan skeleton |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU183182B true HU183182B (en) | 1984-04-28 |
Family
ID=3906663
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU801791A HU183182B (en) | 1979-07-24 | 1980-07-17 | Process for preparing steroid hormones with pregnane skeleton |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5622797A (enExample) |
| BG (1) | BG29777A1 (enExample) |
| CS (1) | CS231563B1 (enExample) |
| GR (1) | GR69192B (enExample) |
| HU (1) | HU183182B (enExample) |
| IN (1) | IN151353B (enExample) |
| PL (1) | PL215749A1 (enExample) |
| RO (1) | RO79971A (enExample) |
| YU (1) | YU176780A (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58161979U (ja) * | 1982-04-20 | 1983-10-28 | 株式会社キト− | 小型捲上兼牽引装置 |
| US9677346B2 (en) | 2012-11-28 | 2017-06-13 | Ultra Premium Oilfield Services, Ltd. | Tubular connection with helically extending torque shoulder |
| US9869139B2 (en) | 2012-11-28 | 2018-01-16 | Ultra Premium Oilfield Services, Ltd. | Tubular connection with helically extending torque shoulder |
| CN103232514B (zh) * | 2013-04-28 | 2014-04-02 | 赵云现 | 醋酸可的松的制备方法 |
| CN103421070A (zh) * | 2013-08-30 | 2013-12-04 | 郑州大学 | 一种改进的孕甾烯类化合物c21-乙酰氧基化方法 |
-
1979
- 1979-07-24 BG BG7945363A patent/BG29777A1/xx unknown
-
1980
- 1980-07-08 GR GR62404A patent/GR69192B/el unknown
- 1980-07-09 YU YU01767/80A patent/YU176780A/xx unknown
- 1980-07-11 IN IN796/CAL/80A patent/IN151353B/en unknown
- 1980-07-15 CS CS805065A patent/CS231563B1/cs unknown
- 1980-07-17 HU HU801791A patent/HU183182B/hu unknown
- 1980-07-18 PL PL21574980A patent/PL215749A1/xx unknown
- 1980-07-19 RO RO80101762A patent/RO79971A/ro unknown
- 1980-07-24 JP JP10063080A patent/JPS5622797A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BG29777A1 (en) | 1981-02-16 |
| PL215749A1 (enExample) | 1981-04-24 |
| CS231563B1 (en) | 1984-12-14 |
| RO79971B (ro) | 1983-01-30 |
| RO79971A (ro) | 1983-02-01 |
| JPS5622797A (en) | 1981-03-03 |
| IN151353B (enExample) | 1983-04-02 |
| GR69192B (enExample) | 1982-05-06 |
| YU176780A (en) | 1984-02-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Löken et al. | Steroids. LXXVII. 1 Synthesis and reactions of 16β-oxygenated pregnan-20-one derivatives | |
| Nakamura et al. | Stereocontrolled construction of oxygenated steroidal side chains. Synthesis and stereochemistry of depresosterol | |
| Bharucha et al. | The conversion of hyodesoxycholic acid to progesterone | |
| HU183182B (en) | Process for preparing steroid hormones with pregnane skeleton | |
| CA2394731C (en) | Process for preparing 17alpha-acetoxy-11beta-[4-n,n-(dimethylamino)phenyl]-21-methoxy-19-norpregna-4,9-diene-3,20-dione, intermediates useful in the process, and processes for preparing such intermediates | |
| US2752339A (en) | Preparation of cortisone | |
| US2773076A (en) | Process of preparing compounds having adreno-cortical hormone activity | |
| JPS6197298A (ja) | ２３位置にジヒドロオキサゾリル基を含む新規なステロイド化合物、それらの製造法、２０‐ケトプレグナン系化合物の製造への使用及びその中間体 | |
| US3036061A (en) | Steroids | |
| US2767155A (en) | Cortical hormones | |
| JPS58219196A (ja) | ４′−デメチル−エピポドフイロトキシン−β−Ｄ−エチリデングルコシドの製造法 | |
| Morrow et al. | Synthesis of 17-disubstituted steroids by the Claisen rearrangement | |
| US3102145A (en) | Intermediate in the preparation of 19-nor-progesterone | |
| US2705719A (en) | Preparation of aromatic steroids and intermediates therefor | |
| US4031080A (en) | 16-Alpha-methyl-17 alpha-bromo-1,4-pregnadiene-21-ol-3,20-dione-derivatives | |
| USRE22941E (en) | X-substituted | |
| JPH0122278B2 (enExample) | ||
| US2915535A (en) | Process and intermediates to produce substituted 4-bromo-21-acetoxy-pregnane-3, 20-dione compounds | |
| SU1132791A3 (ru) | Способ получени производных 17 @ -окси-прегн,-4-ен-3,20-диона | |
| JPH01131194A (ja) | プレグナノ［１７α，１６α−ｄ］オキサゾリン誘導体の製造法 | |
| US2686790A (en) | Tritylated hydroxyetiocholanic acids | |
| JPH023798B2 (enExample) | ||
| US3113142A (en) | Ring contraction process and products manufactured thereby | |
| US3033872A (en) | Method of making a substituted pregnadiene-dione | |
| US2813107A (en) | Pregnane compounds and a process of making same |