SU828970A3 - Способ получени сложных эноль-НыХ эфиРОВ СТЕРОидОВ - Google Patents
Способ получени сложных эноль-НыХ эфиРОВ СТЕРОидОВ Download PDFInfo
- Publication number
- SU828970A3 SU828970A3 SU772451700A SU2451700A SU828970A3 SU 828970 A3 SU828970 A3 SU 828970A3 SU 772451700 A SU772451700 A SU 772451700A SU 2451700 A SU2451700 A SU 2451700A SU 828970 A3 SU828970 A3 SU 828970A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- diene
- steroid
- amino
- pregna
- chloroethyl
- Prior art date
Links
- -1 steroid enol esters Chemical class 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 3
- 150000003431 steroids Chemical class 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 2
- 239000002253 acid Substances 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 125000000468 ketone group Chemical group 0.000 claims description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- UPVNJOUINDANKT-UGCZWRCOSA-N (5S,8S,9S,10S,13S,14S)-10,13-dimethyl-2,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene Chemical compound C([C@@H]1CC2)=CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 UPVNJOUINDANKT-UGCZWRCOSA-N 0.000 claims description 2
- NUPLBTPPIOMJPG-PNKHAZJDSA-N (8r,9s,10r,13s,14s)-13-methyl-1,2,7,8,9,10,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene Chemical compound C1C=C2C=CCC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 NUPLBTPPIOMJPG-PNKHAZJDSA-N 0.000 claims description 2
- HFJJFVWDQNSUGH-VMXHOPILSA-N (8s,9s,10r,13s,14s)-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]1CCC[C@@]1(C)CC2 HFJJFVWDQNSUGH-VMXHOPILSA-N 0.000 claims description 2
- IGJGDNGVVSKWKG-DXUGQKIESA-N (9s,10r,13r,14r,17s)-17-ethyl-10,13-dimethyl-2,9,11,12,14,15,16,17-octahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1=CCC[C@]2(C)[C@@H](CC[C@@]3([C@@H](CC)CC[C@H]33)C)C3=CC=C21 IGJGDNGVVSKWKG-DXUGQKIESA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229930194542 Keto Natural products 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims 2
- 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 claims 1
- GFLFYGQMMWGKMN-BYZMTCBYSA-N (8s,9s,10r,13r,14s,17s)-17-ethyl-10,13-dimethyl-8,9,11,12,14,15,16,17-octahydro-7h-cyclopenta[a]phenanthrene Chemical compound C1C=C2C=CC=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 GFLFYGQMMWGKMN-BYZMTCBYSA-N 0.000 claims 1
- WGBUTJCBIKWVDA-BDXSIMOUSA-N (8s,9s,13s,14s)-13-methyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene Chemical compound C([C@H]1[C@@H]2CCC[C@]2(CC[C@@H]11)C)CC2=C1CCC=C2 WGBUTJCBIKWVDA-BDXSIMOUSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 abstract description 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- 150000002085 enols Chemical class 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000003804 gonanes Chemical class 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 26
- 239000000243 solution Substances 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- NTDNQJMXFXTZLE-UGCZWRCOSA-N (5s,8s,9s,10s,13s,14s)-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C([C@@H]1CC2)C=CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 NTDNQJMXFXTZLE-UGCZWRCOSA-N 0.000 description 1
- YXRFQWKNFFQPAQ-LEKSSAKUSA-N 1-[(8s,9s,10r,13s,14s,17s)-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound C1C=C2C=CCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 YXRFQWKNFFQPAQ-LEKSSAKUSA-N 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- ILOJBLLNJCDTAS-UHFFFAOYSA-N CC1=C(C(=C(C=C1)C(=O)O)N)CCCl Chemical compound CC1=C(C(=C(C=C1)C(=O)O)N)CCCl ILOJBLLNJCDTAS-UHFFFAOYSA-N 0.000 description 1
- 101100189913 Caenorhabditis elegans pept-1 gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000490229 Eucephalus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- 229940035423 ethyl ether Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- AFJYYKSVHJGXSN-KAJWKRCWSA-N selamectin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1C(/C)=C/C[C@@H](O[C@]2(O[C@@H]([C@@H](C)CC2)C2CCCCC2)C2)C[C@@H]2OC(=O)[C@@H]([C@]23O)C=C(C)C(=N\O)/[C@H]3OC\C2=C/C=C/[C@@H]1C AFJYYKSVHJGXSN-KAJWKRCWSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0088—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing unsubstituted amino radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB6512/76A GB1527161A (en) | 1976-02-19 | 1976-02-19 | Enol esters of steroids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU828970A3 true SU828970A3 (ru) | 1981-05-07 |
Family
ID=9815869
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772451700A SU828970A3 (ru) | 1976-02-19 | 1977-02-14 | Способ получени сложных эноль-НыХ эфиРОВ СТЕРОидОВ |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4150126A (enExample) |
| JP (1) | JPS52100458A (enExample) |
| AT (1) | AT358200B (enExample) |
| AU (1) | AU511532B2 (enExample) |
| BE (1) | BE851649A (enExample) |
| CA (1) | CA1087167A (enExample) |
| DE (1) | DE2707121A1 (enExample) |
| DK (1) | DK71977A (enExample) |
| ES (1) | ES456057A1 (enExample) |
| FI (1) | FI57114C (enExample) |
| FR (1) | FR2341594A1 (enExample) |
| GB (1) | GB1527161A (enExample) |
| HU (1) | HU176558B (enExample) |
| LU (1) | LU76795A1 (enExample) |
| NL (1) | NL7701585A (enExample) |
| NO (1) | NO770560L (enExample) |
| NZ (1) | NZ183376A (enExample) |
| SE (1) | SE7700170L (enExample) |
| SU (1) | SU828970A3 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2719457C2 (ru) * | 2015-06-29 | 2020-04-17 | Галеника С.А. | Сложные эфиры стероидного лактама и производных бис(2-хлорэтил)аминофеноксипропановой кислоты |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4261910A (en) * | 1978-08-14 | 1981-04-14 | Kureha Kagaku Kogyo Kabushiki Kaisha | Process for the preparation of Chlorambucil derivatives |
| US4260736A (en) * | 1978-08-14 | 1981-04-07 | Kureha Kagaku Kogyo Kabushiki Kaisha | Steroid hormone-antitumor derivatives |
| US4512986A (en) * | 1983-07-26 | 1985-04-23 | Research Triangle Institute | Progrestationally active steroids |
| JPS61293993A (ja) * | 1985-06-21 | 1986-12-24 | Kureha Chem Ind Co Ltd | 新規な螢光物質，その製造方法及び薬剤 |
| JPH0621072B2 (ja) * | 1986-11-12 | 1994-03-23 | 呉羽化学工業株式会社 | エストラジオ−ル誘導体よりなる免疫調節剤 |
| GB9003939D0 (en) * | 1990-02-21 | 1990-04-18 | Imperial College | Sulphatase inhibitors |
| DE59109185D1 (de) * | 1990-08-18 | 2000-04-20 | Schering Ag | Verfahren zur Herstellung von 20-METHYL-5,7-PREGNADIEN-3 DOLLAR g(b),21-DIOL-DERIVATIVEN |
| GB9118465D0 (en) * | 1991-08-29 | 1991-10-16 | Imperial College | Steroid sulphatase inhibitors |
| GB0304927D0 (en) | 2003-03-04 | 2003-04-09 | Resolution Chemicals Ltd | Process for the production of tibolone |
-
1976
- 1976-02-19 GB GB6512/76A patent/GB1527161A/en not_active Expired
-
1977
- 1977-01-10 SE SE7700170A patent/SE7700170L/ not_active Application Discontinuation
- 1977-01-17 US US05/760,151 patent/US4150126A/en not_active Expired - Lifetime
- 1977-01-28 FI FI770296A patent/FI57114C/fi not_active IP Right Cessation
- 1977-02-09 AU AU22091/77A patent/AU511532B2/en not_active Expired
- 1977-02-14 SU SU772451700A patent/SU828970A3/ru active
- 1977-02-15 NL NL7701585A patent/NL7701585A/xx not_active Application Discontinuation
- 1977-02-17 CA CA271,963A patent/CA1087167A/en not_active Expired
- 1977-02-17 LU LU76795A patent/LU76795A1/xx unknown
- 1977-02-17 HU HU77LE801A patent/HU176558B/hu unknown
- 1977-02-18 AT AT111977A patent/AT358200B/de not_active IP Right Cessation
- 1977-02-18 NO NO770560A patent/NO770560L/no unknown
- 1977-02-18 JP JP1633477A patent/JPS52100458A/ja active Pending
- 1977-02-18 DE DE19772707121 patent/DE2707121A1/de not_active Withdrawn
- 1977-02-18 ES ES456057A patent/ES456057A1/es not_active Expired
- 1977-02-18 NZ NZ183376A patent/NZ183376A/xx unknown
- 1977-02-18 DK DK71977A patent/DK71977A/da unknown
- 1977-02-21 FR FR7704960A patent/FR2341594A1/fr active Granted
- 1977-02-21 BE BE175104A patent/BE851649A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2719457C2 (ru) * | 2015-06-29 | 2020-04-17 | Галеника С.А. | Сложные эфиры стероидного лактама и производных бис(2-хлорэтил)аминофеноксипропановой кислоты |
Also Published As
| Publication number | Publication date |
|---|---|
| SE7700170L (sv) | 1977-08-20 |
| NO770560L (no) | 1977-08-22 |
| FI770296A7 (enExample) | 1977-08-20 |
| AT358200B (de) | 1980-08-25 |
| FI57114B (fi) | 1980-02-29 |
| AU2209177A (en) | 1978-08-17 |
| NL7701585A (nl) | 1977-08-23 |
| CA1087167A (en) | 1980-10-07 |
| FR2341594B1 (enExample) | 1980-09-19 |
| DE2707121A1 (de) | 1977-09-01 |
| HU176558B (en) | 1981-03-28 |
| AU511532B2 (en) | 1980-08-21 |
| DK71977A (da) | 1977-08-20 |
| LU76795A1 (enExample) | 1978-10-18 |
| ATA111977A (de) | 1980-01-15 |
| US4150126A (en) | 1979-04-17 |
| FI57114C (fi) | 1980-06-10 |
| GB1527161A (en) | 1978-10-04 |
| BE851649A (fr) | 1977-08-22 |
| NZ183376A (en) | 1980-04-28 |
| FR2341594A1 (fr) | 1977-09-16 |
| JPS52100458A (en) | 1977-08-23 |
| ES456057A1 (es) | 1978-06-01 |
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| Vincze et al. | Steroids 49. Investigations on the dehydration of 17α-ethynl-17β-hydroxysteroids | |
| Zheng et al. | A convenient and efficient one-pot conversion of peimisine into cyclopamine |