SE301309B - - Google Patents
Info
- Publication number
- SE301309B SE301309B SE1105261A SE1105261A SE301309B SE 301309 B SE301309 B SE 301309B SE 1105261 A SE1105261 A SE 1105261A SE 1105261 A SE1105261 A SE 1105261A SE 301309 B SE301309 B SE 301309B
- Authority
- SE
- Sweden
- Prior art keywords
- formyl
- diene
- enol
- methoxy
- ether
- Prior art date
Links
- -1 chlorethynyl Chemical group 0.000 abstract 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 150000002596 lactones Chemical class 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- 150000003431 steroids Chemical class 0.000 abstract 2
- 229920002554 vinyl polymer Polymers 0.000 abstract 2
- XIIAYQZJNBULGD-UHFFFAOYSA-N (5alpha)-cholestane Natural products C1CC2CCCCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 XIIAYQZJNBULGD-UHFFFAOYSA-N 0.000 abstract 1
- CZHRPATVHYCKRE-CQQQGGGPSA-N (8R,9S,10R,13R,14S,17S)-6-formyl-17-(1-hydroxyethyl)-3-methoxy-10-methyl-2,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-13-carboxylic acid Chemical compound C(=O)C=1C[C@H]2[C@@H]3CC[C@H](C(C)O)[C@]3(CC[C@@H]2[C@]2(CCC(=CC12)OC)C)C(=O)O CZHRPATVHYCKRE-CQQQGGGPSA-N 0.000 abstract 1
- XSEGZMGGWOSZDS-FLWFXTAKSA-N (8R,9S,10R,13S,14S)-17-acetyl-3-methoxy-10,13,16-trimethyl-2,7,8,9,11,12,14,15-octahydro-1H-cyclopenta[a]phenanthrene-6-carbaldehyde Chemical compound C(=O)C=1C[C@H]2[C@@H]3CC(=C(C(C)=O)[C@]3(CC[C@@H]2[C@]2(CCC(=CC12)OC)C)C)C XSEGZMGGWOSZDS-FLWFXTAKSA-N 0.000 abstract 1
- JWMFYGXQPXQEEM-UEDPGYFUSA-N (8S,9R,10R,13R,14S,17S)-17-ethyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene Chemical class CC[C@H]1CC[C@H]2[C@@H]3CCC4CCCC[C@@]4(C)[C@@H]3CC[C@]12C JWMFYGXQPXQEEM-UEDPGYFUSA-N 0.000 abstract 1
- QZLYKIGBANMMBK-XTFZJFRFSA-N (8S,9R,10R,13S,14S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene Chemical compound C[C@@]12CCC[C@H]1[C@@H]1CCC3CCCC[C@@]3(C)[C@@H]1CC2 QZLYKIGBANMMBK-XTFZJFRFSA-N 0.000 abstract 1
- WFUFKDFRQIDJCS-GJINLHFDSA-N (8S,9R,10S,13S,14S,17S)-17-acetyl-3-methoxy-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-6-carbaldehyde Chemical compound C(=O)C=1C[C@H]2[C@@H]3CC[C@H](C(C)=O)[C@]3(CC[C@H]2[C@@]2(CCC(=CC12)OC)C)C WFUFKDFRQIDJCS-GJINLHFDSA-N 0.000 abstract 1
- ALSXNTIVNJBNQE-ZWONNITHSA-N (8r,9r,10s,13r,14s,17s)-17-ethyl-13-methyl-1,2,3,4,5,6,7,8,9,10,11,12,14,15,16,17-hexadecahydrocyclopenta[a]phenanthrene Chemical compound C1CC2CCCC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 ALSXNTIVNJBNQE-ZWONNITHSA-N 0.000 abstract 1
- YEYWUTRGKZIONH-RSAWAZGESA-N 2-[(8S,9S,10R,13S,14S)-6-formyl-3-methoxy-10,13-dimethyl-11-oxo-2,7,8,9,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-ylidene]ethyl acetate Chemical compound C(C)(=O)OCC=C1CC[C@H]2[C@@H]3CC(=C4C=C(CC[C@]4(C)[C@H]3C(C[C@]12C)=O)OC)C=O YEYWUTRGKZIONH-RSAWAZGESA-N 0.000 abstract 1
- WAAWMJYYKITCGF-WTPIMUJOSA-N 5alpha-ergostane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CC[C@H](C)C(C)C)[C@@]2(C)CC1 WAAWMJYYKITCGF-WTPIMUJOSA-N 0.000 abstract 1
- GKBHKNPLNHLYHT-UHFFFAOYSA-N 5beta-Stigmastan Natural products C1CC2CCCCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 GKBHKNPLNHLYHT-UHFFFAOYSA-N 0.000 abstract 1
- QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 abstract 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 abstract 1
- 229930194542 Keto Natural products 0.000 abstract 1
- 101100241859 Mus musculus Oacyl gene Proteins 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- 239000012445 acidic reagent Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- XIIAYQZJNBULGD-LDHZKLTISA-N cholestane Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 XIIAYQZJNBULGD-LDHZKLTISA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- RKHQGWMMUURILY-UHRZLXHJSA-N cortivazol Chemical group C([C@H]1[C@@H]2C[C@H]([C@]([C@@]2(C)C[C@H](O)[C@@H]1[C@@]1(C)C2)(O)C(=O)COC(C)=O)C)=C(C)C1=CC1=C2C=NN1C1=CC=CC=C1 RKHQGWMMUURILY-UHRZLXHJSA-N 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 abstract 1
- 150000002084 enol ethers Chemical class 0.000 abstract 1
- 125000003700 epoxy group Chemical group 0.000 abstract 1
- GRXPVLPQNMUNNX-MHJRRCNVSA-N estrane Chemical compound C1CC2CCCC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 GRXPVLPQNMUNNX-MHJRRCNVSA-N 0.000 abstract 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 abstract 1
- AUAZBCWTBVDFKZ-GXVBGZBGSA-N ethyl 2-[(8S,9S,10R,13S,14S)-6-formyl-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-ylidene]acetate Chemical compound CCOC(=O)C=C1CC[C@H]2[C@@H]3CC(C=O)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C AUAZBCWTBVDFKZ-GXVBGZBGSA-N 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 230000002035 prolonged effect Effects 0.000 abstract 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 abstract 1
- INLFWQCRAJUDCR-LYLBMTSKSA-N spirostane Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CCCCC4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 INLFWQCRAJUDCR-LYLBMTSKSA-N 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
- GKBHKNPLNHLYHT-LWQAOISPSA-N stigmastane Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 GKBHKNPLNHLYHT-LWQAOISPSA-N 0.000 abstract 1
- LAGFCVRVICMFFF-UHFFFAOYSA-N stigmastane Natural products CCC(CCC(C)C1CCC2C3CCC4CC(=O)CC(C)C4C3CCC12C)C(C)C LAGFCVRVICMFFF-UHFFFAOYSA-N 0.000 abstract 1
- 150000003573 thiols Chemical class 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 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
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
-
- 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
- A61K31/568—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 substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
-
- 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
- A61K31/568—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 substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
- A61K31/569—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 substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone substituted in position 17 alpha, e.g. ethisterone
-
- 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
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- 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
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
-
- 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
- C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- 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
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J73/00—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3823660A GB929983A (en) | 1960-11-07 | 1960-11-07 | 6-formyl steroids |
Publications (1)
Publication Number | Publication Date |
---|---|
SE301309B true SE301309B (zh) | 1968-06-04 |
Family
ID=10402138
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SE1105261A SE301309B (zh) | 1960-11-07 | 1961-11-07 |
Country Status (6)
Country | Link |
---|---|
BE (1) | BE610054A (zh) |
BR (1) | BR6133972D0 (zh) |
CH (1) | CH476707A (zh) |
FR (3) | FR1563606A (zh) |
GB (1) | GB929983A (zh) |
SE (1) | SE301309B (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3004508C2 (de) * | 1980-02-05 | 1981-12-10 | Schering Ag Berlin Und Bergkamen, 1000 Berlin | Verfahren zur Herstellung von 6-Methylensteroiden |
FR2724174B1 (fr) | 1994-09-06 | 1997-01-17 | Roussel Uclaf | Procede de preparation d'un derive steroide 17beta-carboxy et nouveaux intermediaires |
-
1960
- 1960-11-07 GB GB3823660A patent/GB929983A/en not_active Expired
-
1961
- 1961-11-07 BR BR13397261A patent/BR6133972D0/pt unknown
- 1961-11-07 BE BE610054A patent/BE610054A/fr unknown
- 1961-11-07 FR FR1563606D patent/FR1563606A/fr not_active Expired
- 1961-11-07 FR FR1563605D patent/FR1563605A/fr not_active Expired
- 1961-11-07 SE SE1105261A patent/SE301309B/xx unknown
- 1961-11-07 FR FR1563607D patent/FR1563607A/fr not_active Expired
- 1961-11-07 CH CH1291061A patent/CH476707A/de not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
FR1563606A (zh) | 1969-04-18 |
CH476707A (de) | 1969-08-15 |
BE610054A (fr) | 1962-05-07 |
FR1563605A (zh) | 1969-04-18 |
FR1563607A (zh) | 1969-04-18 |
GB929983A (en) | 1963-06-26 |
BR6133972D0 (pt) | 1973-05-15 |
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