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GB817932A - New compounds derived from tetrahydro-oxazine compounds and theophylline or halogen-theophyllines

Publication number

GB817932A

GB817932A GB35522/55A GB3552255A GB817932A GB 817932 A GB817932 A GB 817932A GB 35522/55 A GB35522/55 A GB 35522/55A GB 3552255 A GB3552255 A GB 3552255A GB 817932 A GB817932 A GB 817932A

Authority

GB

United Kingdom

Prior art keywords

tetrahydro

phenyl

oxazine

theophylline

solvent

Prior art date

1954-12-10

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.)

Expired

• Espacenet
• Global Dossier
• Discuss

• ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 title abstract 9
• 229960000278 theophylline Drugs 0.000 title abstract 6
• 150000001875 compounds Chemical class 0.000 title abstract 3
• KHVCOYGKHDJPBZ-WDCZJNDASA-N tetrahydrooxazine Chemical class OC[C@H]1ONC[C@@H](O)[C@@H]1O KHVCOYGKHDJPBZ-WDCZJNDASA-N 0.000 title 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 12
• DNUJVGBNIXGTHC-UHFFFAOYSA-N 3,6-dihydro-2h-oxazine Chemical class C1NOCC=C1 DNUJVGBNIXGTHC-UHFFFAOYSA-N 0.000 abstract 7
• -1 alkyl radical Chemical group 0.000 abstract 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 4
• 125000004432 carbon atom Chemical group C* 0.000 abstract 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
• 239000002904 solvent Substances 0.000 abstract 4
• YIUIVFFUEVPRIU-UHFFFAOYSA-N 8-chlorotheophylline Chemical compound O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21 YIUIVFFUEVPRIU-UHFFFAOYSA-N 0.000 abstract 3
• 239000007864 aqueous solution Substances 0.000 abstract 3
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 abstract 2
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 abstract 2
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 2
• TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 abstract 2
• 229910052739 hydrogen Inorganic materials 0.000 abstract 2
• 239000001257 hydrogen Substances 0.000 abstract 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
• 238000000034 method Methods 0.000 abstract 2
• 239000000047 product Substances 0.000 abstract 2
• 239000012265 solid product Substances 0.000 abstract 2
• 239000000243 solution Substances 0.000 abstract 2
• 229910021653 sulphate ion Inorganic materials 0.000 abstract 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
• 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
• 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract 1
• QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 abstract 1
• 229910001864 baryta Inorganic materials 0.000 abstract 1
• 238000001704 evaporation Methods 0.000 abstract 1
• 230000008020 evaporation Effects 0.000 abstract 1
• 238000001914 filtration Methods 0.000 abstract 1
• 239000000203 mixture Substances 0.000 abstract 1
• 239000003960 organic solvent Substances 0.000 abstract 1
• 239000000376 reactant Substances 0.000 abstract 1
• 150000003839 salts Chemical class 0.000 abstract 1
• 230000001225 therapeutic effect Effects 0.000 abstract 1

• • 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
  • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
  • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Water-soluble tetrahydro-1 : 4-oxazine derivatives are prepared by reacting a tetrahydro-1 : 4-oxazine of the formula <FORM:0817932/IV (b)/1> (wherein R1 is phenyl or substituted phenyl such as 4-hydroxy-, 3 : 4-dihydroxy- or o-chloro phenyl, R2 is an alkyl radical of at most 3 carbon atoms and R3 is hydrogen, an alkyl radical of at most 3 carbon atoms or hydroxyethyl) with theophylline or an 8-halogenotheophylline, preferably in molar proportions. The reactants may be heated alone to 128 DEG to 130 DEG C. or they may be refluxed in a solvent, e.g. an organic solvent such as methanol, or water, or they may be intimately ground together alone or in presence of a solvent, e.g. acetone. Alternatively, a salt of the tetrahydro-1 : 4-oxazine, e.g. its sulphate or hydrosulphate, is reacted with the theophylline compound in the presence of a quantity of an alkaline earth metal hydroxide equivalent to the quantity of sulphate present in a solvent, e.g. water or methanol, and the alkaline earth metal salt formed is removed. The product may be recovered from these processes by evaporation of the solvent where used or it may be isolated as an aqueous solution. Optically active tetrahydro-1 : 4-oxazines may be used in these processes. In examples: (1) 2 - phenyl - 3 - methyl - tetrahydro - 1 : 4 - oxazine and 8-chlorotheophylline are ground together to give a water-soluble product; (2) 2-(21 - chloro - phenyl) - 3 - methyl - tetrahydro - 1 : 4-oxazine and 8-chlorotheophylline are boiled together in methanol and the solution evaporated to give a solid product; (3) 2-(41-hydroxyphenyl) - 3 - methyl - tetrahydro - 1 : 4-oxazine hydrosulphate and theophylline in methanol are mixed with a concentrated baryta solution and boiled to give, on filtering off the barium sulphate, an aqueous solution of the required compound; and (4) 2-phenyl-3-methyl-4-hydroxyethyl - tetrahydro - 1 : 4 - oxazine and 8-chlorotheophylline are ground together in acetone to give a solid product.ALSO:Therapeutic compositions comprise aqueous solutions of compounds formed by the reaction of tetrahydro-1 : 4-oxazines of the formula <FORM:0817932/VI/1> (wherein R1 is phenyl or substituted phenyl such as 4-hydroxy-, 3 : 4-dihydroxy- or o-chloro-phenyl, R2 is an alkyl radical of at most 3 carbon atoms and R3 is hydrogen, an alkyl radical of at most 3 carbon atoms or hydroxyethyl) with theophylline or an 8-halogeno-theophylline. Examples are given.

• 1955
  • 1955-12-09 GB GB35522/55A patent/GB817932A/en not_active Expired

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