GB1423576A - Butyrophenone derivatives and production thereof - Google Patents

Butyrophenone derivatives and production thereof

Info

Publication number
GB1423576A
GB1423576A GB1280473A GB1280473A GB1423576A GB 1423576 A GB1423576 A GB 1423576A GB 1280473 A GB1280473 A GB 1280473A GB 1280473 A GB1280473 A GB 1280473A GB 1423576 A GB1423576 A GB 1423576A
Authority
GB
United Kingdom
Prior art keywords
alkyl
formula
halogen
alkoxy
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
GB1280473A
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.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co 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
Priority claimed from JP47027610A external-priority patent/JPS5755714B2/ja
Priority claimed from JP47057249A external-priority patent/JPS4914476A/ja
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Publication of GB1423576A publication Critical patent/GB1423576A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
    • C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/16—Radicals substituted by halogen atoms or nitro radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1423576 Butyrophenone derivatives SUMITOMO CHEMICAL CO Ltd 16 March 1973 [18 March 1972 7 June 1972] 12804/73 Heading C2C Novel compounds of Formula I wherein R is an oxygen atom, an ethylenedioxy or ethylenedithio group and wherein Z is a secondary amino group of one of the formulµ wherein R<SP>1</SP> is H or OH, R<SP>2</SP> and R<SP>3</SP>, independently, denote H, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or CF 3 , and n is 0 or 1 wherein R<SP>4</SP> is H, or C 1 -C 4 alkyl, R<SP>5</SP> and R<SP>6</SP>, independently, denote H, halogen, or C 1 -C 4 alkyl, and the dotted line represents an optional additional bond between the carbon atoms at the 3- and 4- positions of the piperidino ring wherein R<SP>7</SP> is H or C 1 -C 4 alkyl and R<SP>8</SP> is H, halogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy wherein R<SP>9</SP> is H, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or CF 3 , and m is 0, 1 or 2; and wherein R<SP>10</SP> is H, halogen, OH, C 1 -C 4 alkyl or C 1 -C 4 alkoxy, may be obtained by reacting a compound of Formula I<SP>1</SP> where X is a halogen atom with a secondary amine of formula HZ. Compounds of Formula VII, wherein A is a group of the Formula VIII or IX and W is morpholino, pyrrolidino, piperidino or -NR<SP>11</SP>(R<SP>12</SP>), where R<SP>11</SP> and R<SP>12</SP> are, independently, each a H atom, optionally HO- substituted-C 1 -C 8 -alkyl, C 1 -C 4 alkoxy-C 1 -C 8 alkyl, di (C 1 -C 4 alkyl)-C 1 -C 8 alkyl, C 3 -C 7 cycloalkyl or optionally substituted aryl, or W is any of the Formulµ II to VI defined above for Z, may be obtained by reacting a compound of the Formula X (i.e. I in which R is an oxygen atom) with a compound HW. Compounds of Formula VII, excepting those in which A is VIII and W is amino or N-monoalkylamino, are novel compounds. Pharamaceutical compositions, having depressive properties on the central and autonomic nervous system, comprise a compound of Formula I or VII above, or a salt thereof, together with a pharmaceutically acceptable carrier or diluent, which may be processed to tablets, capsules, pills or ampoules. Reference has been directed by the Comptroller to Specifications 1,332,737, 1,304,599, 1,301,631 and 1,301,431.
GB1280473A 1972-03-18 1973-03-16 Butyrophenone derivatives and production thereof Expired GB1423576A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP47027610A JPS5755714B2 (en) 1972-03-18 1972-03-18
JP47057249A JPS4914476A (en) 1972-06-07 1972-06-07

Publications (1)

Publication Number Publication Date
GB1423576A true GB1423576A (en) 1976-02-04

Family

ID=26365557

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1280473A Expired GB1423576A (en) 1972-03-18 1973-03-16 Butyrophenone derivatives and production thereof

Country Status (10)

Country Link
AU (1) AU470114B2 (en)
CA (1) CA1024984A (en)
CH (2) CH599939A5 (en)
FI (1) FI58636C (en)
FR (1) FR2183683B1 (en)
GB (1) GB1423576A (en)
HU (1) HU167671B (en)
NL (1) NL7303854A (en)
NO (2) NO144068C (en)
SE (1) SE419441B (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS595587B2 (en) * 1974-04-18 1984-02-06 住友化学工業株式会社 Synkinabutylofenon Yudoutai Oyobi Sonoen no Seihou
JPS5116677A (en) * 1974-07-29 1976-02-10 Sumitomo Chemical Co SHINKINABUCHIROFUENONJUDOTAI OYOBI SONOSANFUKAENNOSEIHO
FR2530632A1 (en) * 1982-07-26 1984-01-27 Bouchara Emile NOVEL SUBSTITUTED 2,5-DIAMINO 1,4-DIAZOLE DERIVATIVES, PROCESSES FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
US4569933A (en) * 1984-04-13 1986-02-11 Cornu Pierre Jean Antihypertensive substituted derivatives of 2,5-diamino 1,4-diazole

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1304599A (en) * 1969-07-16 1973-01-24
SE381656B (en) * 1970-02-06 1975-12-15 Sumitomo Chemical Co METHOD OF PREPARATION OF 1,2,3,4-TETRAHYDROISOCHINOLINE DERIVATIVES
DE2110534C3 (en) * 1970-03-06 1979-03-08 Sumitomo Chemical Co., Ltd., Osaka (Japan) γ-Piperazinobutyrophenone derivatives, process for their production and medicinal preparations
US3799932A (en) * 1970-03-20 1974-03-26 Sumitomo Chemical Co Gamma-piperidinobutyrophenones

Also Published As

Publication number Publication date
NO144069C (en) 1981-06-17
AU5346873A (en) 1974-09-19
AU470114B2 (en) 1976-03-04
FI58636C (en) 1981-03-10
NO144068C (en) 1981-06-17
CH599939A5 (en) 1978-06-15
NO144068B (en) 1981-03-09
CA1024984A (en) 1978-01-24
NL7303854A (en) 1973-09-20
FI58636B (en) 1980-11-28
SE419441B (en) 1981-08-03
CH589626A5 (en) 1977-07-15
HU167671B (en) 1975-11-28
FR2183683A1 (en) 1973-12-21
FR2183683B1 (en) 1976-12-31
NO144069B (en) 1981-03-09

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee