GB1479241A - 10,11-dihydro-10-piperazinyl-dibenz(b,f)oxepins methods for their preparation and compositions containing them - Google Patents

10,11-dihydro-10-piperazinyl-dibenz(b,f)oxepins methods for their preparation and compositions containing them

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Publication number
GB1479241A
GB1479241A GB241/75A GB24175A GB1479241A GB 1479241 A GB1479241 A GB 1479241A GB 241/75 A GB241/75 A GB 241/75A GB 24175 A GB24175 A GB 24175A GB 1479241 A GB1479241 A GB 1479241A
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GB
United Kingdom
Prior art keywords
prepared
substituted
compounds
alkyl
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
GB241/75A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1479241A publication Critical patent/GB1479241A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/44—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by —CHO groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
    • C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
    • C07D313/02—Seven-membered rings
    • C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
    • C07D313/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
    • C07D313/14—[b,f]-condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

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

Abstract

1479241 10,11-Dihydro-10-piperazyl-oxyines F HOFFMANN-LA ROCHE & CO AG 3 Jan 1975 [4 Jan 1974] 241/75 Heading C2C Novel compounds I and their salts in which R is a C 1-6 alkyl, C 3-6 alkenyl or C 3-6. 0 alkaryl group (which may be substituted by cyano, hydroxy or C 2-18 alkanoyloxy when R is other than methyl and in which unsaturation does not take place at the 1-position) or a group in which X is O, S, NH, CH 2 or C 1-6 alkylimino Y is an ethylene or propylene group optionally substituted by C 1-6 alkyl and m is 0 or 1, one of R 1 and R 2 is-H, and the other is halogen, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkylthio, CF 3 or OH and one of R 3 and R 4 is H and the other is H, halogen, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkylthio, CF, or OH are prepared by (i) reacting a compound II in which Z is a leaving atom or group and R<SP>1</SP> 1 , R<SP>1</SP> 2 , R<SP>1</SP> 3 and R<SP>1</SP> 4 have the values of R 1 to R 4 respectively and in addition any hydroxy group present may be protected, with an R substituted piperazine (2) reducing the corresponding #<SP>10,11</SP> compound in which any hydroxy group R 1 to R 4 may be protected or (3) introducing a group R into a compound V in a manner known per se. Compounds I (R=an alkanoyloxy substituted C 1-6 alkyl, C 3-6 alkenyl or C 3-6 alkynyl group) are prepared by esterifying the corresponding hydroxy substituted compound in which compound any hydroxy group R 1 to R 4 may be protected. Compounds I (R = C 1-6 alkyl or hydroxy C 1-6 alkyl) are prepared by reducing a compound VII in which R 5 is C 1-6 alkanoyl, hydroxy C 1-6 alkanoyl or (C 1-6 alkoxy) carbonyl. Compounds V are prepared by reacting an R<SP>1</SP> 1 , R<SP>1</SP> 2 , R<SP>1</SP> 3 , R<SP>1</SP> 4 substituted 10,11-dehydro-10-oxo-oxepine (XVI) with ethyl piperazinocarboxylate reducing the 10,11-double bond and decarboxylating. Compounds II (Z = C1) are prepared by reducing a compound XVI to the 10-ol and chlorinating. Compounds XVI (R<SP>1</SP> 1 or R<SP>1</SP> 2 =Me, Cl, MeO, R<SP>1</SP> 3 or R<SP>1</SP> 4 =Me, Cl, F, MeS, CF), are prepared by reacting an Me or Cl substituted 2-iodobenzoic acid with an Me, F or Cl substituted phenol and submitting the resultant 2-phenoxybenzoic acid to the standard homologation procedure to form the corresponding phenyl-acetic acid which is cyclized. Compounds XVI (R<SP>1</SP> 1 =F, Cl, Br) are prepared reduction of the nitro-derivative to an amine, diazotisation and reaction with NaBF 4 , CuCl or CuBr. 8-Fluoro- 10,11 - dihydro - 2 - nitro - oxepin - 10 - one is prepared by reacting 4-fluorophenol with 2- chloro-5-nitro benzaldehyde and treating the 2 - (p - fluorophenoxy) - 5 - nitro - benzaldehyde formed with acetylglycine in AC 2 O to give 2- (p - fluorophenoxy)- 5 - nitro - phenylpyruvic acid which is decarboxylated to the phenylacetic acid and cyclized. Me and MeO substituted 2-iodo-benzoic acids are prepared by diazotisation and iodination of the corresponding arthranilic acid. Compounds I have CNS depressant and neuroleptic properties and form with a carrier a pharmaceutical composition which may be administered orally, parenterally or rectally.
GB241/75A 1974-01-04 1975-01-03 10,11-dihydro-10-piperazinyl-dibenz(b,f)oxepins methods for their preparation and compositions containing them Expired GB1479241A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH6274A CH598252A5 (en) 1974-01-04 1974-01-04

Publications (1)

Publication Number Publication Date
GB1479241A true GB1479241A (en) 1977-07-06

Family

ID=4178442

Family Applications (1)

Application Number Title Priority Date Filing Date
GB241/75A Expired GB1479241A (en) 1974-01-04 1975-01-03 10,11-dihydro-10-piperazinyl-dibenz(b,f)oxepins methods for their preparation and compositions containing them

Country Status (12)

Country Link
JP (1) JPS5096583A (en)
AT (1) AT346847B (en)
BE (1) BE824066A (en)
CA (1) CA1055025A (en)
CH (1) CH598252A5 (en)
DE (1) DE2461137A1 (en)
FR (1) FR2256762B1 (en)
GB (1) GB1479241A (en)
IL (1) IL46194A (en)
NL (1) NL7417008A (en)
PH (1) PH13598A (en)
ZA (1) ZA747670B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0148417A1 (en) * 1983-12-12 1985-07-17 Hoechst-Roussel Pharmaceuticals Incorporated Analgesic dibenz[b,f]oxepins, a process for their preparation and their use as medicaments
US11673864B2 (en) 2013-01-31 2023-06-13 Vertex Pharmaceuticals Incorporated Pyridone amides as modulators of sodium channels

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5700445A (en) * 1994-12-12 1997-12-23 Allelix Biopharmaceuticals, Inc. N-methyl piperazine compounds having dopamine receptor affinity

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0148417A1 (en) * 1983-12-12 1985-07-17 Hoechst-Roussel Pharmaceuticals Incorporated Analgesic dibenz[b,f]oxepins, a process for their preparation and their use as medicaments
US11673864B2 (en) 2013-01-31 2023-06-13 Vertex Pharmaceuticals Incorporated Pyridone amides as modulators of sodium channels

Also Published As

Publication number Publication date
ATA3975A (en) 1978-04-15
FR2256762B1 (en) 1978-07-21
BE824066A (en) 1975-07-03
ZA747670B (en) 1975-12-31
NL7417008A (en) 1975-07-08
CA1055025A (en) 1979-05-22
AU7610874A (en) 1976-06-10
FR2256762A1 (en) 1975-08-01
IL46194A (en) 1980-05-30
IL46194A0 (en) 1975-03-13
JPS5096583A (en) 1975-07-31
DE2461137A1 (en) 1975-07-17
AT346847B (en) 1978-11-27
CH598252A5 (en) 1978-04-28
PH13598A (en) 1980-08-05

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee