GB377255A - Manufacture of therapeutically active compounds - Google Patents

Manufacture of therapeutically active compounds

Info

Publication number
GB377255A
GB377255A GB1101431A GB1101431A GB377255A GB 377255 A GB377255 A GB 377255A GB 1101431 A GB1101431 A GB 1101431A GB 1101431 A GB1101431 A GB 1101431A GB 377255 A GB377255 A GB 377255A
Authority
GB
United Kingdom
Prior art keywords
imide
perhydrocarbazole
aminopyridine
atoms
compound
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.)
Expired
Application number
GB1101431A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to DEI41174D priority Critical patent/DE586802C/en
Application filed by Individual filed Critical Individual
Priority to GB1101431A priority patent/GB377255A/en
Priority to US602400A priority patent/US2003623A/en
Publication of GB377255A publication Critical patent/GB377255A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/14—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
    • C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
    • C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
    • C07D473/12—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1, 3, and 7, e.g. caffeine

Landscapes

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

Abstract

Perhydrocarbazole derivatives are prepared by exchanging the imine hydrogen in known manner for a residue containing one or more basic nitrogen atoms, i.e. capable of combining by addition with hydrogen chloride or bromide, said basic nitrogen atom or atoms being linked by an aliphatic residue with the imino group. The same products may also be obtained by treating a compound, derived from perhydrocarbazole by substitution of the imine hydrogen by an aliphatic residue containing a reactive group, with a compound containing a group capable of interaction with the reactive group and containing one or more nitrogen atoms which are either basic in character or rendered basic by subsequent treatment, e.g. reduction. The aliphatic residue may contain oxygen atoms or other nitrogen atoms or cyclic carbon atoms. According to the examples, (1) 1-perhydrocarbazylethylpyridone-2-imide is prepared by treating perhydrocarbazole with ethylene oxide or ethylene chlorhydrin, converting the oxyethylperhydrocarbazole into the N-chlorethyl compound by means of thionyl chloride, and treating it with 2-aminopyridine; using 4-methyl-2-aminopyridine in the final stage, 1-perhydrocarbazylethyl - 4 - methylpyridone - 2 - imide is obtained; similarly, 1-perhydrocarbazylethylpyridone-4-imide is formed by interaction of the N-chlorethyl compound with 4-aminopyridine, 1-perhydrocarbazylethylquinolone-2-imide using 2-aminoquinoline, 1-perhydrocarbazylethyl - 2 - methyl - 6 - ethoxyquinolone-4-imide using 6-ethoxy-4-aminoquinaldine, 1-perhydrocarbazylethylimidazole using imidazole, 1-perhydrocarbazylethyl - 5 - methylpyrazoline using 5-methylpyrazoline, methylaminoethyl-perhydrocarbazole using methylamine, diethyl-aminoethylperhydrocarbazole using diethyl-amine, benzylaminoethylperhydrocarbazole using benzylamine, methylbenzylaminoethyl-perhydrocarbazole using methylbenzylamine and 1-perhydrocarbazyl-2-hydroxy-3-diethyl-aminopropane using diethylaminoepihydrin; (2) 1-(1<1>-perhydrocarbazyl-3<1>-diethylaminopropyl-2<1>) -pyridone-2-imide is obtained by converting 1 - perhydrocarbazyl - 2 - hydroxy - 3 -di-ethylaminopropane into the 2-chloro compound by means of thionyl chloride and treating it with 2-aminopyridine; (3) 8-perhydrocarbazyl-ethoxycaffeine is prepared by interaction of N-oxyethylperhydrocarbazole with chlorocaffeine; from the same starting material is obtained diperhydrocarbazylethane using ethylene bromide, 2-imino-3-perhydrocarbazylethyl-4-methylthiazole-2 : 3-dihydride using 4-methyl-2-aminothiazole, 1 - perhydrocarbazylethyl - 2 - methylimidazole-4 : 5-dihydride using 2-methyl4 : 5-dihydroimidazole and 2-perhydrocarbazyl-ethylaminopyridine using 2-aminopyridine; (4) m-tolylhydrazine is condensed with cyclohexanol, the resulting 7-methyl-1 : 2 : 3 : 4-tetrahydrocarbazole then hydrogenated to 2-methylperhydrocarbazole, which is treated in succession with ehtylene chlorhydrin, thionyl chloride and 2-aminopyridine, to form 1-(2<1>-methyl) perhydrocarbazylethylpyridone-2-imide. The formul of the products are given. The Provisional Specification states that the residue connecting the imino group with the basic nitrogen atom or atoms may also be cyclic or alicyclic or may comprise an aliphatic chain containing sulphur atoms. If the connecting member is to consist wholly or partly of a cyclic hydrocarbon residue, the perhydrocarbazole may be treated with an aromatic body containing nitrogen and a reactive halogen, e.g. p-nitrochlorbenzene and the product further converted into a polyamino compound.
GB1101431A 1931-04-05 1931-04-14 Manufacture of therapeutically active compounds Expired GB377255A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DEI41174D DE586802C (en) 1931-04-05 1931-04-05 Process for the preparation of particles of perhydrocarbazole
GB1101431A GB377255A (en) 1931-04-14 1931-04-14 Manufacture of therapeutically active compounds
US602400A US2003623A (en) 1931-04-05 1932-03-31 Heterocyclically substituted perhydrocarbazoles

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1101431A GB377255A (en) 1931-04-14 1931-04-14 Manufacture of therapeutically active compounds

Publications (1)

Publication Number Publication Date
GB377255A true GB377255A (en) 1932-07-14

Family

ID=9978454

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1101431A Expired GB377255A (en) 1931-04-05 1931-04-14 Manufacture of therapeutically active compounds

Country Status (1)

Country Link
GB (1) GB377255A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2541211A (en) * 1948-10-15 1951-02-13 Searle & Co Tertiary-aminoalkyl-tetrahydrocarbazoles
US2569415A (en) * 1947-12-24 1951-09-25 Ciba Pharm Prod Inc Imidazolines
US2687414A (en) * 1948-11-26 1954-08-24 Searle & Co Method for producing aromatic aminoalkyl amines
US2751393A (en) * 1953-05-13 1956-06-19 Imidazoline derivatives of aryl indoles

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2569415A (en) * 1947-12-24 1951-09-25 Ciba Pharm Prod Inc Imidazolines
US2541211A (en) * 1948-10-15 1951-02-13 Searle & Co Tertiary-aminoalkyl-tetrahydrocarbazoles
US2687414A (en) * 1948-11-26 1954-08-24 Searle & Co Method for producing aromatic aminoalkyl amines
US2751393A (en) * 1953-05-13 1956-06-19 Imidazoline derivatives of aryl indoles

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