SU450404A3 - СПОСОБ ПОЛУЧЕНИЯ 3-ЦИКЛОПЕНТИЛОВОГО ЭФИРА7а-МЕТИЛ-3,16а, П-ТРИОКСИ-А^з.^сю) ЭСТРАТРИЕПА ИЛИ ЕГО 16,17-ДИАЦЕТАТОВ - Google Patents
СПОСОБ ПОЛУЧЕНИЯ 3-ЦИКЛОПЕНТИЛОВОГО ЭФИРА7а-МЕТИЛ-3,16а, П-ТРИОКСИ-А^з.^сю) ЭСТРАТРИЕПА ИЛИ ЕГО 16,17-ДИАЦЕТАТОВInfo
- Publication number
- SU450404A3 SU450404A3 SU1649123A SU1649123A SU450404A3 SU 450404 A3 SU450404 A3 SU 450404A3 SU 1649123 A SU1649123 A SU 1649123A SU 1649123 A SU1649123 A SU 1649123A SU 450404 A3 SU450404 A3 SU 450404A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- methyl
- water
- estratriene
- formula
- esterified
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 8
- 230000012173 estrus Effects 0.000 title 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 5
- -1 steroid compounds Chemical class 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 4
- 238000002360 preparation method Methods 0.000 claims 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 150000007513 acids Chemical class 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 239000012043 crude product Substances 0.000 claims 3
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 claims 3
- BOTLEXFFFSMRLQ-UHFFFAOYSA-N cyclopentyloxycyclopentane Chemical compound C1CCCC1OC1CCCC1 BOTLEXFFFSMRLQ-UHFFFAOYSA-N 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 3
- 239000000741 silica gel Substances 0.000 claims 3
- 229910002027 silica gel Inorganic materials 0.000 claims 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical group CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 238000000862 absorption spectrum Methods 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Chemical group CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 238000005886 esterification reaction Methods 0.000 claims 2
- 239000005457 ice water Substances 0.000 claims 2
- 238000002844 melting Methods 0.000 claims 2
- 230000008018 melting Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 235000011121 sodium hydroxide Nutrition 0.000 claims 2
- 239000000725 suspension Substances 0.000 claims 2
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical group COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Chemical group 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- BRTFVKHPEHKBQF-UHFFFAOYSA-N bromocyclopentane Chemical compound BrC1CCCC1 BRTFVKHPEHKBQF-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 150000002009 diols Chemical class 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 230000001766 physiological effect Effects 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical group 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 claims 1
- 230000007017 scission Effects 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
- 150000003460 sulfonic acids Chemical class 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/168—Steroids
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/184—Hormones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Food Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Pharmacology & Pharmacy (AREA)
- Endocrinology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH621970A CH551959A (de) | 1970-04-24 | 1970-04-24 | Verfahren zur herstellung neuer oestrogen hochwirksamer steroide. |
| CH622070A CH540243A (de) | 1970-04-24 | 1970-04-24 | Verfahren zur Herstellung eines neuen, östrogen hochwirksamen Steroids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU450404A3 true SU450404A3 (ru) | 1974-11-15 |
Family
ID=25699190
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1649123A SU450404A3 (ru) | 1970-04-24 | 1971-04-23 | СПОСОБ ПОЛУЧЕНИЯ 3-ЦИКЛОПЕНТИЛОВОГО ЭФИРА7а-МЕТИЛ-3,16а, П-ТРИОКСИ-А^з.^сю) ЭСТРАТРИЕПА ИЛИ ЕГО 16,17-ДИАЦЕТАТОВ |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3804866A (enExample) |
| AR (3) | AR192730A1 (enExample) |
| AT (2) | AT312825B (enExample) |
| BE (1) | BE766184A (enExample) |
| CA (1) | CA931944A (enExample) |
| CS (2) | CS157118B2 (enExample) |
| DE (1) | DE2118995A1 (enExample) |
| DK (1) | DK128533B (enExample) |
| FI (1) | FI48729C (enExample) |
| FR (1) | FR2092082B1 (enExample) |
| HU (1) | HU162762B (enExample) |
| IE (1) | IE35147B1 (enExample) |
| IL (1) | IL36654A (enExample) |
| NL (1) | NL7105578A (enExample) |
| PL (1) | PL81612B1 (enExample) |
| SE (1) | SE373577B (enExample) |
| SU (1) | SU450404A3 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3929844A (en) * | 1970-04-24 | 1975-12-30 | Ciba Geigy Corp | 3-Cyclopentyl ethers of 7{60 -methyl estrone |
| DE10159217A1 (de) | 2001-11-27 | 2003-06-05 | Schering Ag | 17alpha-Alkyl-17ß-oxy-estratriene und Zwischenprodukte zu deren Herstellung, Verwendung der 17alpha-Alkyl-17ß-oxy-estratriene zur Herstellung von Arzneimitteln sowie pharmazeutische Präparate |
| US20040242551A1 (en) * | 2003-05-28 | 2004-12-02 | Schering Ag | Composition comprising antiprogestins and pure antiestrogens for prophylaxis and treatment of hormone-dependent diseases |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1866M (fr) * | 1961-04-07 | 1963-06-17 | Vismara Francesco Spa | Nouveaux éthers des hormones oestrogenes. |
| CH537914A (de) * | 1969-02-27 | 1973-06-15 | Ciba Geigy Ag | Verfahren zur Herstellung eines neuen pharmakologisch hochwirksamen Östratriols |
| FR2034569B1 (enExample) * | 1969-02-27 | 1973-07-13 | Ciba Geigy Ag |
-
1971
- 1971-04-19 CA CA110656A patent/CA931944A/en not_active Expired
- 1971-04-19 IL IL36654A patent/IL36654A/xx unknown
- 1971-04-20 IE IE491/71A patent/IE35147B1/xx unknown
- 1971-04-20 DE DE19712118995 patent/DE2118995A1/de active Pending
- 1971-04-21 US US00136170A patent/US3804866A/en not_active Expired - Lifetime
- 1971-04-22 HU HUCI1106A patent/HU162762B/hu unknown
- 1971-04-22 PL PL1971147684A patent/PL81612B1/pl unknown
- 1971-04-22 FR FR7114322A patent/FR2092082B1/fr not_active Expired
- 1971-04-23 CS CS298671A patent/CS157118B2/cs unknown
- 1971-04-23 NL NL7105578A patent/NL7105578A/xx unknown
- 1971-04-23 AT AT273072A patent/AT312825B/de not_active IP Right Cessation
- 1971-04-23 BE BE766184A patent/BE766184A/xx unknown
- 1971-04-23 FI FI711131A patent/FI48729C/fi active
- 1971-04-23 AT AT351171A patent/AT311567B/de not_active IP Right Cessation
- 1971-04-23 CS CS173873*1A patent/CS157119B2/cs unknown
- 1971-04-23 SE SE7105303A patent/SE373577B/xx unknown
- 1971-04-23 SU SU1649123A patent/SU450404A3/ru active
- 1971-12-27 AR AR239826A patent/AR192730A1/es active
- 1971-12-27 AR AR239837A patent/AR192731A1/es active
- 1971-12-27 AR AR239825A patent/AR192605A1/es active
-
1972
- 1972-08-18 DK DK412172AA patent/DK128533B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2118995A1 (de) | 1971-11-04 |
| CS157119B2 (enExample) | 1974-08-23 |
| FR2092082A1 (enExample) | 1972-01-21 |
| IE35147L (en) | 1971-10-24 |
| HU162762B (enExample) | 1973-04-28 |
| AT312825B (de) | 1974-01-25 |
| AT311567B (de) | 1973-11-26 |
| IE35147B1 (en) | 1975-11-26 |
| IL36654A (en) | 1974-07-31 |
| CA931944A (en) | 1973-08-14 |
| SU447884A3 (ru) | 1974-10-25 |
| FI48729B (enExample) | 1974-09-02 |
| US3804866A (en) | 1974-04-16 |
| AR192731A1 (es) | 1973-03-14 |
| CS157118B2 (enExample) | 1974-08-23 |
| FR2092082B1 (enExample) | 1974-08-23 |
| AR192730A1 (es) | 1973-03-14 |
| FI48729C (fi) | 1974-12-10 |
| AR192605A1 (es) | 1973-02-28 |
| SE373577B (sv) | 1975-02-10 |
| BE766184A (fr) | 1971-10-25 |
| PL81612B1 (enExample) | 1975-08-30 |
| DK128533B (da) | 1974-05-20 |
| NL7105578A (enExample) | 1971-10-26 |
| IL36654A0 (en) | 1971-08-25 |
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