GB1373246A - Benzopyrano derivatives and processes for the preparation thereof - Google Patents

Benzopyrano derivatives and processes for the preparation thereof

Info

Publication number
GB1373246A
GB1373246A GB5289971A GB5289971A GB1373246A GB 1373246 A GB1373246 A GB 1373246A GB 5289971 A GB5289971 A GB 5289971A GB 5289971 A GB5289971 A GB 5289971A GB 1373246 A GB1373246 A GB 1373246A
Authority
GB
United Kingdom
Prior art keywords
prepared
ring
azaxanthene
piperidylidene
polyhaloalkyl
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
GB5289971A
Inventor
F J Villani
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.)
Scherico Ltd
Original Assignee
Scherico Ltd
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
Application filed by Scherico Ltd filed Critical Scherico Ltd
Publication of GB1373246A publication Critical patent/GB1373246A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1373246 Azaxanthene derivatives SCHERICO Ltd 15 Nov 1971 [16 Nov 1970] 52899/71 Heading C2C The invention comprises compounds of formula and their pharmaceutically acceptable acid addition salts, wherein the ring labelled (N) is a pyridine ring, (in which the N atom may not be in a ring-fusion position), Q is halogen, polyhaloalkyl (C 1-6 ), OH or C 1-6 alkoxy; n is 0, 1 or 2; A is 3- or 4- piperidylidene (possibly NC 1-6 alkyl or -polyhaloalkyl-substituted) or is C 2-4 aminoalkylidene (possibly N-mono- or di- C 1-6 -alkyl-substituted) with at least 2 C atoms between N and the tricyclic nucleus; and W is H(Ia) or OH (Ib) while R is H, or W-R forms a further bond (Ic). In examples, Ia are prepared by hydrogenating Ic; Ib are prepared by reacting the corresponding azaxanthone with RAMgCl or RACl+Na/NH 3 ; and Ic are prepared by (i) heating Ib with polyphosphoric acid or H 2 SO 4 , (ii) cyclizing with polyphosphoric acid a phenoxypyridyl/N-methylpiperidyl ketone or ketimine, (iii) removing the O of a corresponding N-oxide, (iv) decarboxylating a derived carboxylic acid, and (v) (where A is piperidylidene) removing an N-methyl group, replacing an N- attached H atom by Me or CH 2 CF 3 , or reacting the tetrahydropyranylidene analogue (itself made from the tetrahydropyranyl-hydroxy-azaxanthene) with MeNH 2 . Therapeutic compositions having bronchodilator and (in the case of 3-azaxanthenes) CNS activity, comprise compounds of the above formula, and may be administered orally, parenterally or by inhalation.
GB5289971A 1970-11-16 1971-11-15 Benzopyrano derivatives and processes for the preparation thereof Expired GB1373246A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US9000470A 1970-11-16 1970-11-16

Publications (1)

Publication Number Publication Date
GB1373246A true GB1373246A (en) 1974-11-06

Family

ID=22220642

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5289971A Expired GB1373246A (en) 1970-11-16 1971-11-15 Benzopyrano derivatives and processes for the preparation thereof

Country Status (17)

Country Link
AT (3) AT320646B (en)
AU (1) AU463647B2 (en)
BE (1) BE775370A (en)
CA (1) CA966136A (en)
DD (1) DD108754A5 (en)
DE (1) DE2156235A1 (en)
ES (1) ES397014A1 (en)
FR (1) FR2113971B1 (en)
GB (1) GB1373246A (en)
HU (1) HU164332B (en)
IE (1) IE35810B1 (en)
IL (1) IL38144A (en)
NL (1) NL7115753A (en)
PL (3) PL92091B1 (en)
SE (1) SE375533B (en)
SU (1) SU406348A3 (en)
ZA (1) ZA717653B (en)

Also Published As

Publication number Publication date
AT319237B (en) 1974-12-10
IL38144A0 (en) 1972-01-27
DE2156235A1 (en) 1972-05-18
IL38144A (en) 1974-11-29
NL7115753A (en) 1972-05-18
ZA717653B (en) 1972-11-29
ES397014A1 (en) 1975-03-01
PL92091B1 (en) 1977-03-31
DD108754A5 (en) 1974-10-05
HU164332B (en) 1974-01-28
FR2113971A1 (en) 1972-06-30
BE775370A (en) 1972-05-16
SU406348A3 (en) 1973-11-05
SE375533B (en) 1975-04-21
IE35810L (en) 1972-05-16
CA966136A (en) 1975-04-15
IE35810B1 (en) 1976-05-26
AU3570171A (en) 1973-05-24
AU463647B2 (en) 1975-07-17
FR2113971B1 (en) 1975-10-10
PL86672B1 (en) 1976-06-30
AT315172B (en) 1974-05-10
AT320646B (en) 1975-02-25
PL81681B1 (en) 1975-08-30

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees