DE2110084A1 - Neue l,2-Methylen-17alpha-acyloxy (oder verätherte Hydroxy)-9beta, lOalpha-steroid-Verbindungen der Pregnanreihe, pharmaceutische Präparate auf Basis dieser neuen Verbindungen und Verfahren zur Herstellung dieser Verbindungen und Präparate - Google Patents
Neue l,2-Methylen-17alpha-acyloxy (oder verätherte Hydroxy)-9beta, lOalpha-steroid-Verbindungen der Pregnanreihe, pharmaceutische Präparate auf Basis dieser neuen Verbindungen und Verfahren zur Herstellung dieser Verbindungen und PräparateInfo
- Publication number
- DE2110084A1 DE2110084A1 DE19712110084 DE2110084A DE2110084A1 DE 2110084 A1 DE2110084 A1 DE 2110084A1 DE 19712110084 DE19712110084 DE 19712110084 DE 2110084 A DE2110084 A DE 2110084A DE 2110084 A1 DE2110084 A1 DE 2110084A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- methylene
- hydroxy
- compound
- dione
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 79
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title claims description 70
- 238000000034 method Methods 0.000 title claims description 40
- 238000002360 preparation method Methods 0.000 title claims description 34
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- 239000000825 pharmaceutical preparation Substances 0.000 title claims 2
- JWMFYGXQPXQEEM-WZBAXQLOSA-N pregnane Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 JWMFYGXQPXQEEM-WZBAXQLOSA-N 0.000 title 1
- 229910052731 fluorine Inorganic materials 0.000 claims description 41
- 125000001153 fluoro group Chemical group F* 0.000 claims description 39
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 229910052801 chlorine Inorganic materials 0.000 claims description 31
- 239000002904 solvent Substances 0.000 claims description 29
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 27
- -1 6,7-methylene group Chemical group 0.000 claims description 24
- 239000013543 active substance Substances 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 150000002500 ions Chemical class 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- 239000012876 carrier material Substances 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 8
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 claims description 6
- 241000251730 Chondrichthyes Species 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 239000000262 estrogen Substances 0.000 claims description 5
- 229940011871 estrogen Drugs 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 239000012320 chlorinating reagent Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- JGMOKGBVKVMRFX-LEKSSAKUSA-N (8s,9s,10r,13s,14s,17s)-17-acetyl-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C1=CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 JGMOKGBVKVMRFX-LEKSSAKUSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 238000005822 methylenation reaction Methods 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000001145 hydrido group Chemical group *[H] 0.000 claims 2
- 230000002152 alkylating effect Effects 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000002084 enol ethers Chemical class 0.000 claims 1
- 239000012025 fluorinating agent Substances 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 46
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
- 239000000284 extract Substances 0.000 description 13
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- 238000002844 melting Methods 0.000 description 11
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 150000003431 steroids Chemical class 0.000 description 7
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- 230000007935 neutral effect Effects 0.000 description 6
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- 239000000460 chlorine Substances 0.000 description 5
- 239000008298 dragée Substances 0.000 description 5
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
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- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 5
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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- 238000004587 chromatography analysis Methods 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
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- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 229920001592 potato starch Polymers 0.000 description 4
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- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
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- 238000002425 crystallisation Methods 0.000 description 3
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- DKWOHBPRFZIUQL-UHFFFAOYSA-N dimethyl-methylidene-oxo-$l^{6}-sulfane Chemical compound C[S+](C)([CH2-])=O DKWOHBPRFZIUQL-UHFFFAOYSA-N 0.000 description 3
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
-
- 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
-
- 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
- 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
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
- C07J53/004—3 membered carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/001—Oxiranes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (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 |
|---|---|---|---|
| NL7003064A NL7003064A (ja) | 1970-03-04 | 1970-03-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2110084A1 true DE2110084A1 (de) | 1971-09-16 |
Family
ID=19809490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712110084 Pending DE2110084A1 (de) | 1970-03-04 | 1971-03-03 | Neue l,2-Methylen-17alpha-acyloxy (oder verätherte Hydroxy)-9beta, lOalpha-steroid-Verbindungen der Pregnanreihe, pharmaceutische Präparate auf Basis dieser neuen Verbindungen und Verfahren zur Herstellung dieser Verbindungen und Präparate |
Country Status (13)
| Country | Link |
|---|---|
| JP (4) | JPS5038103B1 (ja) |
| AT (4) | AT312828B (ja) |
| BE (1) | BE763754A (ja) |
| CA (1) | CA972350A (ja) |
| CH (1) | CH564944A5 (ja) |
| DE (1) | DE2110084A1 (ja) |
| ES (4) | ES388854A1 (ja) |
| FR (1) | FR2085668B1 (ja) |
| GB (1) | GB1330563A (ja) |
| IL (1) | IL36324A0 (ja) |
| NL (1) | NL7003064A (ja) |
| SE (1) | SE373750B (ja) |
| ZA (1) | ZA711332B (ja) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITBZ20030005A1 (it) | 2003-01-30 | 2004-07-31 | High Technology Invest Bv | Dispositivo pressore per la conduzione di fune in sistemi di trasporto a trazione di fune. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3198792A (en) * | 1962-06-12 | 1965-08-03 | Philips Corp | 10alpha methyl, 9beta hormonal steroids |
| GB1247661A (en) * | 1967-07-11 | 1971-09-29 | Philips Nv | NEW 9beta,10alpha-STEROIDS AND METHODS OF PRODUCING THE SAME |
-
1970
- 1970-03-04 NL NL7003064A patent/NL7003064A/xx unknown
-
1971
- 1971-03-01 SE SE7102589A patent/SE373750B/xx unknown
- 1971-03-01 CH CH295471A patent/CH564944A5/xx not_active IP Right Cessation
- 1971-03-02 AT AT414172A patent/AT312828B/de not_active IP Right Cessation
- 1971-03-02 AT AT414072A patent/AT316769B/de not_active IP Right Cessation
- 1971-03-02 AT AT176671A patent/AT315390B/de not_active IP Right Cessation
- 1971-03-02 CA CA106,613A patent/CA972350A/en not_active Expired
- 1971-03-02 AT AT413972A patent/AT316768B/de not_active IP Right Cessation
- 1971-03-02 ZA ZA711332A patent/ZA711332B/xx unknown
- 1971-03-02 IL IL36324A patent/IL36324A0/xx unknown
- 1971-03-03 DE DE19712110084 patent/DE2110084A1/de active Pending
- 1971-03-03 ES ES388854A patent/ES388854A1/es not_active Expired
- 1971-03-03 BE BE763754A patent/BE763754A/xx unknown
- 1971-03-04 FR FR7107523A patent/FR2085668B1/fr not_active Expired
- 1971-03-04 JP JP46011246A patent/JPS5038103B1/ja active Pending
- 1971-04-19 GB GB2284771A patent/GB1330563A/en not_active Expired
- 1971-11-22 ES ES397228A patent/ES397228A1/es not_active Expired
- 1971-11-22 ES ES397231A patent/ES397231A1/es not_active Expired
- 1971-11-22 ES ES397229A patent/ES397229A1/es not_active Expired
-
1974
- 1974-12-13 JP JP49143367A patent/JPS50105662A/ja active Pending
- 1974-12-13 JP JP49143366A patent/JPS50105661A/ja active Pending
- 1974-12-13 JP JP49143365A patent/JPS50105660A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2085668B1 (ja) | 1974-08-02 |
| BE763754A (fr) | 1971-09-03 |
| IL36324A0 (en) | 1971-05-26 |
| AT312828B (de) | 1974-01-25 |
| ES397231A1 (es) | 1975-04-01 |
| NL7003064A (ja) | 1971-09-07 |
| JPS50105660A (ja) | 1975-08-20 |
| JPS50105661A (ja) | 1975-08-20 |
| CA972350A (en) | 1975-08-05 |
| FR2085668A1 (ja) | 1971-12-31 |
| AT316769B (de) | 1974-07-25 |
| ZA711332B (en) | 1972-10-25 |
| ES397229A1 (es) | 1975-04-01 |
| CH564944A5 (ja) | 1975-08-15 |
| GB1330563A (en) | 1973-09-19 |
| ES388854A1 (es) | 1974-03-16 |
| JPS50105662A (ja) | 1975-08-20 |
| ES397228A1 (es) | 1975-04-01 |
| AT315390B (de) | 1974-05-27 |
| AT316768B (de) | 1974-07-25 |
| JPS5038103B1 (ja) | 1975-12-06 |
| SE373750B (ja) | 1975-02-17 |
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