NO131133B - - Google Patents
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- Publication number
- NO131133B NO131133B NO366373A NO366373A NO131133B NO 131133 B NO131133 B NO 131133B NO 366373 A NO366373 A NO 366373A NO 366373 A NO366373 A NO 366373A NO 131133 B NO131133 B NO 131133B
- Authority
- NO
- Norway
- Prior art keywords
- oxazolidine
- general formula
- steroid
- functional derivative
- carbonyl compound
- Prior art date
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- 150000001728 carbonyl compounds Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 101000687448 Homo sapiens REST corepressor 1 Proteins 0.000 claims description 3
- 102100024864 REST corepressor 1 Human genes 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- -1 steroid oxazolidine oxazines Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 4
- 150000003431 steroids Chemical class 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
Analogifremgangsmåte til fremstilling av Analogy method for the production of
terapeutisk virksomme steroid-oksazolidinoksaziner. therapeutically active steroid oxazolidine oxazines.
Foreliggende oppfinnelse vedrører en analogifremgangsmåte til fremstilling av terapeutisk virksomme steroid-oksazolidinoksaziner med den generelle -formel: hvor R, som kan være like eller forskjellige, er hydrogen eller metyl og denne fremgangsmåte er kjennetegnet ved at en steroid-oksazolidin med den generelle, formel: The present invention relates to an analogous process for the production of therapeutically effective steroid-oxazolidine oxazines with the general formula: where R, which may be the same or different, is hydrogen or methyl and this process is characterized by the fact that a steroid-oxazolidine with the general formula:
hvor R har den ovenfor angitte betydning, omsettes med en karbonyl-forbindelse med den generelle formel RCOR, hvor R har den ovenfor angitte betydning, eller et funksjonelt derivat derav, ved en temperatur på mellom 0°C og karbonylforbindelsens éller dens funksjonelle derivats kokepunkttempera'tur. where R has the meaning given above, is reacted with a carbonyl compound of the general formula RCOR, where R has the meaning given above, or a functional derivative thereof, at a temperature between 0°C and the boiling point temperature of the carbonyl compound or its functional derivative' trip.
De fremstilte, hittil ukjente forbindelser som har terapeutisk virkning, har spesielt en meget sterk betennelseshemmende virkning. The manufactured, hitherto unknown compounds which have a therapeutic effect, in particular have a very strong anti-inflammatory effect.
Kondensasjonen mellom steroid-oksazolidinet og karbonyl-forbindelsen RCOR, hvor R har den angitte betydning, eller et funksjonelt derivat av karbonylgruppen, slik som et acetal, kan utføres i nærvær av vann eller under vannfrie betingelser. . Cyklopentanringen D i steroidet har, som det fremgår fra formlene, en temmelig fastlagt struktur, mens strukturen til de andre tre ringer i steroidet kan variere i utstrakt grad. F.eks. kan det være en eller flere dobbeltbindinger i stillingene 1, ^, 6, 9, (11). OksygenhoIdige grupper slik som en ketongruppe eller en hydroksygruppe kan wære tilstede i stillingene 3 og 11 eller i begge stillinger. Det er også mulig å utføre de ovenfor angitte reaksjoner på steroider med en 9~halogensubstituent. The condensation between the steroid oxazolidine and the carbonyl compound RCOR, where R has the stated meaning, or a functional derivative of the carbonyl group, such as an acetal, can be carried out in the presence of water or under anhydrous conditions. . The cyclopentane ring D in the steroid has, as can be seen from the formulas, a rather fixed structure, while the structure of the other three rings in the steroid can vary widely. E.g. there may be one or more double bonds in positions 1, ^, 6, 9, (11). Oxygen-containing groups such as a ketone group or a hydroxy group may be present in positions 3 and 11 or in both positions. It is also possible to carry out the above-mentioned reactions on steroids with a 9-halogen substituent.
Praktisk talt alle forbindelser som er omfattet av følgende formel-har betennelseshemmende virkning: Practically all compounds covered by the following formula have an anti-inflammatory effect:
hvor R, som er like eller forskjellige, er hydrogen, en lavere alkylgruppe eller arylgruppe, og som kan ha en eller to oksygen-holdige grupper i stillingene 3 og 11 eller i begge stillinger, et halogenatom kan være tilstede i stilling 9, og det kan forefinnes where R, which are the same or different, is hydrogen, a lower alkyl group or an aryl group, and which may have one or two oxygen-containing groups in positions 3 and 11 or in both positions, a halogen atom may be present in position 9, and the can be found
dobbeltbindinger mellom stillingene 1, (2) og/eller 4, (5) og/eller 9, (ID-Fremgangsmåten ifølge oppfinnelsen skal forklares nærmere double bonds between positions 1, (2) and/or 4, (5) and/or 9, (ID-The method according to the invention must be explained in more detail
Ek sempel 1 9a-fluor-11g-hydroksyandrosta-1, 4-dien-3-on-/ 17a, l6ct-d7-oksazolidin/ 3' 34'- c7- 2"- metyl- 2H- tetrahydro- l, 3- oksazin- 5"- on. Example 1 9a-Fluoro-11g-hydroxyandrosta-1, 4-dien-3-one-/ 17a, 16ct-d7-oxazolidine/ 3' 34'- c7- 2"- methyl- 2H- tetrahydro- 1, 3- oxazine-5"-one.
En blanding av 11 g 11(3, 21-dihydroksy-9ct-f lurpregna-1, 4-dien-3s20-dion-/17a,l6a-d7-oksazolidin, 50 ml vann og 60 ml acetalde- A mixture of 11 g of 11(3,21-dihydroxy-9ct-flupregna-1,4-diene-3s20-dione-/17a,16a-d7-oxazolidine, 50 ml of water and 60 ml of acetaldehyde-
hyd holdes ved 0°C i 2 timer, hvoretter det tilsettes 100 ml vann, hyd is kept at 0°C for 2 hours, after which 100 ml of water is added,
og blandingen ekstraheres med etylacetat. Etter inndampning av opp-løsningsmidlet omkrystalliseres resten fra metanol. Forbindelsen er 9a-fluor- 113-hydroksyandrosta-l ,4-dien-3-on-/17a,l6a-d/'-oksazolidin/3'5^'_c/-2"-mety1-2H-tetrahydro-l,3~oksazin-5"-on med smeltepunkt 248-2*49°C. and the mixture is extracted with ethyl acetate. After evaporation of the solvent, the residue is recrystallized from methanol. The compound is 9a-fluoro-113-hydroxyandrosta-1,4-dien-3-one-[17a,16a-d/'-oxazolidine/3'5^'_c/-2"-methyl-2H-tetrahydro-1, 3~oxazin-5"-one with melting point 248-2*49°C.
Eksempel 2 Example 2
9a-fiuor-116-hydroksyandrosta-l,4-dien-3-on-/17a,l6a-d/-2'-metyloksa-z olidin-/ 3', ^ '- c7- 2H- tetrahydro- l, 3- oksazin- 5"~ on. 9a-fluoro-116-hydroxyandrosta-1,4-dien-3-one-/17a,16a-d/-2'-methyloxa-zolidine-/ 3', ^ '- c7- 2H- tetrahydro- 1, 3 - oxazine- 5"~ on.
En blanding av 8 g 113 , 21-dihydroksy~9a-f luorpregna-1,El-dlen- 3,20-dion-/17a,l6a-d7-2'-metyloksazolidin, 200 ml metanol og vandig J>6% formaldehyd, holdes natten over ved romtemperatur. ' Etter inndampning av metanol oppnås 6,8 g praktisk talt ren forbindelse A mixture of 8 g of 113 , 21-dihydroxy~9a-fluoropregna-1,E1-dlen-3,20-dione-/17a,16a-d7-2'-methyloxazolidine, 200 ml of methanol and aqueous J>6% formaldehyde , kept overnight at room temperature. After evaporation of methanol, 6.8 g of practically pure compound are obtained
ved filtrering. Smeltepunkt 285°C by filtering. Melting point 285°C
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO366373A NO131133C (en) | 1968-05-03 | 1973-09-19 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1602968 | 1968-05-03 | ||
| NO01825/69A NO128608B (en) | 1968-05-03 | 1969-05-02 | |
| NO366373A NO131133C (en) | 1968-05-03 | 1973-09-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO131133B true NO131133B (en) | 1974-12-30 |
| NO131133C NO131133C (en) | 1975-04-09 |
Family
ID=27272884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO366373A NO131133C (en) | 1968-05-03 | 1973-09-19 |
Country Status (1)
| Country | Link |
|---|---|
| NO (1) | NO131133C (en) |
-
1973
- 1973-09-19 NO NO366373A patent/NO131133C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO131133C (en) | 1975-04-09 |
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