NO153769B - Fremgangsmaate ved fremstilling av 2-oxo-dihydro-benzo-(d)(1,3)-oxaziner. - Google Patents
Fremgangsmaate ved fremstilling av 2-oxo-dihydro-benzo-(d)(1,3)-oxaziner. Download PDFInfo
- Publication number
- NO153769B NO153769B NO802844A NO802844A NO153769B NO 153769 B NO153769 B NO 153769B NO 802844 A NO802844 A NO 802844A NO 802844 A NO802844 A NO 802844A NO 153769 B NO153769 B NO 153769B
- Authority
- NO
- Norway
- Prior art keywords
- hydroxy
- keto
- oximino
- oxazines
- benzo
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 4
- 150000001441 androstanes Chemical class 0.000 claims description 4
- 229910017604 nitric acid Inorganic materials 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- -1 potassium amide Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Substances [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 3
- 150000003431 steroids Chemical class 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 229940124325 anabolic agent Drugs 0.000 description 1
- 239000003263 anabolic agent Substances 0.000 description 1
- 230000001195 anabolic effect Effects 0.000 description 1
- 229960003473 androstanolone Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound 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 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/18—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Fremgangsmåte for fremstilling av nye, anabolisk
virksomme 2-oximIno-17B-hydroxy-3-keto-steroider
av androstanrekken.
Foreliggende oppfinnelse angår ^n fremgangsmåte for fremstilling av de nye forbindelser 2-oximirio-17P-hydroxy-17a-me'thyl-åndr.o-stan-3-on og 2-oximino-17p-hydroxy-17a-methyl-androstan-^-en-3-on ved å omsette de.tilsvarende 2-hydroxymethylen-17p-hydroxy-3-keto-17a-methyl steroider med salpetersyrling. Disse 2-oximino steroider er verdifulle som anaboliske midler.
De nye 2-oximin0-17^-hydroxy-3-keto-17a-methyl steroider av androstanrekken kan representeres ved folgende formler:
Fremstillingen av de nye 2-oximino-17{3-hydroxy-3-keto-steroider av androstanrekken ved å omsette dé tilsvarende 2-hydroxy~ methylen-17{3-hydroxy-3-keto-17a-methyl steroider med salpetersyrling kan illustreres ved hjelp av folgende reaksjonsligning:
2-hydroxymethylen-3-keto-steroidmellomproduktene fremstilles ved å kondensere det tilsvarende i 2-posisjonen usubstituerte steroid med.et .alkanoyleringsmiddélf.eks. et lavere alkyl-lavere alkanoat, som ethylformiat eller methylf or.miat, under vannfrie betingelser i nærvær av en sterk base, f.eks. et alkalimetall-lavere alkoxyd, som kaliumamid, et alkalimetallhydrid, som natriumhydrid, oglignende.
Omsetningen mellom 2-hydroxymethylen-3-keto-steroidet og sal-petersyrlingen uff ores ved å bringe reaktantene sammen, fortrinns-vis, i omtrent ekvimolekylært forhold, i en vandig opplosning i en inert atmosfære, f.eks. nitrogen, helium eller argon. 2-hydroxy-methylen-3-keto-^steroidet bpploses i en blanding av et organisk opp-losningsmiddel,. f.eks. et lavere halogenert hydrocarbon, som methylenklorid, kloroform, diklorethan eller triklorethan, og en organisk syre, f.eks. en lavere alkansyre, som maursyre, eddiksyre el ler pro-pionsyre, og en liten mengde vann. Oppløsningen av steroidet av-kjoles i et isbad, og en opplosning av metallnitritt, f.eks. et alkalimetallnitritt som natrium- eller kaliumnitritt, i vann, til-settes. Blandingen av 2-hydrpxymethylen-3-keto-steroidet og. alkali-metallnitrittet omrores ved isbadtemperatur i 0,5 - 6 timer, hvorved det tilsvarende 2-oximino-3-keto-steroid dannes. Dette steroid ut-vinnes bekvemt ved å fortynne reaksjonsblandingen med isvann, hvorpå den dannede vandige blanding ekstraheres med et halogenert hydrocarbon, f.eks. methylenklorid. Den halogenerte hydrocarbon-ekstrakt vaskes fri for sure forurensninger, tbrres og inndampes til torrhet. Det dannede gjenværende materiale rekrystailiseres. fra et organisk opp-losningsmiddel, f.eks. ethylacetat, ethylacetatether og lignende, hvorved det tilsvarende 2-oximino-3-keto-steroid fås i praktisk talt ren form.
Eksempel 1
250 mg 2-hydroxymethylen-17p-hydroxy-17a-methylandrostan (allo-dihydrotestosteron)-3-on.i 3 ml methylenklorid, 15 ml iseddik og 1 ml vann ble avkjolt til 2°C i en nitrogenatmosfære. Blandingen ble om-rort, og 60 mg natriumnitritt.opplost i'3 ml vann ble dråpevis tilsatt idet temperaturen ble holdt ved 2°C. Den dannede blanding fikk hen-stå ved 0°C i 20 minutter. Reaksjonsopplosningen ble så fortynnet med 30 ml iskaldt vann,.og den således dannede, vandige blanding ble ekstrahert 3 ganger med methylenklorid. Methylenkloridekstrakten.ble vasket med vann og en mettet, vandig natriumkloridopplosning, torret og inndampet til tbrrhet. Residuumet ble krystallisert fra ethylacetat, og det ble oppnådd praktisk talt rent 2-oximino-17P~hydroxy-17a-methyl-androstan-3-on. Smeltepunktet var 252-256°C under spaltning.
Eksempel 2
Ved omsetning av 2-hydroxymethylen-17P-hydroxy-17a-methyl-androstan-^-en-3-on med salpetersyrling ved fremgangsmåten beskrevet i eksempel 1 ble 2-oximino-l7p-hydroxy-17a-methyl-androstan-<1>+-en-3-on oppnådd som produkt. Smeltepunktet var 225-228°C under spaltning.
Claims (1)
- Fremgangsmåte for fremstilling av nye, anabolisk virksomme 2-oximino-17P-hydroxy-3-keto-steroider av androstanrekken med formelen, hvor den punkterte • linje mellom carbonatomene h og 5 betyr en eventuell dobbeltbinding, karakterisert ved at en for-bindelse med formelenhvor den punkterte linje mellom carbonatomene h og 5 har den ovenfor angitte betydning, omsettes med salpetersyrling i en inert atmosfære. '
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7933442 | 1979-09-27 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO802844L NO802844L (no) | 1981-03-30 |
| NO153769B true NO153769B (no) | 1986-02-10 |
| NO153769C NO153769C (no) | 1986-07-02 |
Family
ID=10508087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO802844A NO153769C (no) | 1979-09-27 | 1980-09-26 | Fremgangsmaate ved fremstilling av 2-oxo-dihydro-benzo-(d)(1,3)-oxaziner. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4301283A (no) |
| JP (1) | JPS5673049A (no) |
| AT (1) | AT375653B (no) |
| BE (1) | BE885416A (no) |
| CH (1) | CH647240A5 (no) |
| DE (1) | DE3035792C2 (no) |
| DK (1) | DK149887C (no) |
| FI (1) | FI73211C (no) |
| FR (1) | FR2466464A1 (no) |
| GB (1) | GB2060631B (no) |
| IE (1) | IE50245B1 (no) |
| IT (1) | IT1129278B (no) |
| LU (1) | LU82806A1 (no) |
| NL (1) | NL8005364A (no) |
| NO (1) | NO153769C (no) |
| SE (1) | SE457170B (no) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4446319A (en) * | 1981-04-28 | 1984-05-01 | Takeda Chemical Industries, Ltd. | Aminocyclitols and their production |
| DE102007005283A1 (de) * | 2007-02-02 | 2008-08-07 | Cognis Ip Management Gmbh | Lösungsmittel für Phasentransfer-katalysierte Reaktionen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3526621A (en) * | 1966-08-03 | 1970-09-01 | Farmaceutical Italia Soc | Substituted 3,1-benzoxazin-2-one |
| US3705154A (en) * | 1971-07-08 | 1972-12-05 | Ashland Oil Inc | Synthesis of 4h-3,1-benzoxazin-2(1h)-one |
-
1980
- 1980-09-10 US US06/185,990 patent/US4301283A/en not_active Expired - Lifetime
- 1980-09-23 DE DE3035792A patent/DE3035792C2/de not_active Expired
- 1980-09-25 FR FR8020621A patent/FR2466464A1/fr active Granted
- 1980-09-26 DK DK406580A patent/DK149887C/da active
- 1980-09-26 NO NO802844A patent/NO153769C/no unknown
- 1980-09-26 JP JP13415180A patent/JPS5673049A/ja active Pending
- 1980-09-26 NL NL8005364A patent/NL8005364A/nl active Search and Examination
- 1980-09-26 LU LU82806A patent/LU82806A1/de unknown
- 1980-09-26 IT IT68497/80A patent/IT1129278B/it active
- 1980-09-26 SE SE8006761A patent/SE457170B/sv not_active IP Right Cessation
- 1980-09-26 AT AT0482980A patent/AT375653B/de not_active IP Right Cessation
- 1980-09-26 FI FI803041A patent/FI73211C/fi not_active IP Right Cessation
- 1980-09-26 IE IE2024/80A patent/IE50245B1/en unknown
- 1980-09-26 GB GB8031144A patent/GB2060631B/en not_active Expired
- 1980-09-26 BE BE0/202242A patent/BE885416A/fr not_active IP Right Cessation
- 1980-09-26 CH CH7242/80A patent/CH647240A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK149887B (da) | 1986-10-20 |
| SE457170B (sv) | 1988-12-05 |
| DE3035792C2 (de) | 1987-01-15 |
| IT8068497A0 (it) | 1980-09-26 |
| GB2060631A (en) | 1981-05-07 |
| NL8005364A (nl) | 1981-03-31 |
| DK149887C (da) | 1987-04-27 |
| DK406580A (da) | 1981-03-28 |
| NO802844L (no) | 1981-03-30 |
| DE3035792A1 (de) | 1981-04-16 |
| JPS5673049A (en) | 1981-06-17 |
| US4301283A (en) | 1981-11-17 |
| SE8006761L (sv) | 1981-03-28 |
| LU82806A1 (de) | 1980-12-15 |
| ATA482980A (de) | 1984-01-15 |
| FI73211C (fi) | 1987-09-10 |
| IE50245B1 (en) | 1986-03-05 |
| FR2466464B1 (no) | 1983-05-20 |
| FR2466464A1 (fr) | 1981-04-10 |
| CH647240A5 (de) | 1985-01-15 |
| NO153769C (no) | 1986-07-02 |
| GB2060631B (en) | 1983-07-20 |
| IT1129278B (it) | 1986-06-04 |
| FI803041A (fi) | 1981-03-28 |
| AT375653B (de) | 1984-08-27 |
| BE885416A (fr) | 1981-01-16 |
| FI73211B (fi) | 1987-05-29 |
| IE802024L (en) | 1981-03-27 |
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