GB1032054A - Substituted isoquinoline and piperazine derivatives and a process for the manufacture thereof - Google Patents

Substituted isoquinoline and piperazine derivatives and a process for the manufacture thereof

Info

Publication number
GB1032054A
GB1032054A GB28568/63A GB2856863A GB1032054A GB 1032054 A GB1032054 A GB 1032054A GB 28568/63 A GB28568/63 A GB 28568/63A GB 2856863 A GB2856863 A GB 2856863A GB 1032054 A GB1032054 A GB 1032054A
Authority
GB
United Kingdom
Prior art keywords
group
alkyl
alkoxy
reacting
formula
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
GB28568/63A
Inventor
John Mervyn Osbond
Hans Bruderer
James Charles Wickens
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.)
Roche Products Ltd
Original Assignee
Roche Products 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 Roche Products Ltd filed Critical Roche Products Ltd
Priority to GB28568/63A priority Critical patent/GB1032054A/en
Priority to AT569364A priority patent/AT251582B/en
Priority to IL2167464A priority patent/IL21674A/en
Priority to BE650658D priority patent/BE650658A/xx
Priority to FR981790A priority patent/FR4068M/fr
Priority to FR981789A priority patent/FR1408958A/en
Priority to NL6408192A priority patent/NL6408192A/xx
Priority to ES0302224A priority patent/ES302224A1/en
Publication of GB1032054A publication Critical patent/GB1032054A/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
    • C07D295/08—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 singly bound oxygen or sulfur atoms
    • C07D295/084—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 singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • 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
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
    • C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
    • C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/20—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 acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/205—Radicals derived from carbonic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
    • 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)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

The invention comprises compounds of the formula: <FORM:1032054/C2/1> wherein R1 is one of the following groups: <FORM:1032054/C2/2> wherein R2 represents a hydrogen atom or C1- 4 alkyl group, R3 represents a hydroxy group S1, S2 and S3 each represents a halogen atom or C1- 4 alkyl or C1- 4 alkoxy group or, except where R1 represents an S4-piperazino group as formulated above, a nitro or amino group, S4 represents a C1- 4 alkyl or C1- 4 alkoxycarbonyl group or a phenyl group which may carry one or more halo, C1- 4 alkyl, or C1- 4 alkoxy substituents, S5 represents a C1- 4 alkyl, (C2- 4 alkoxycarbonyl)-alkyl or C1- 4 hydroxyalkyl group, S6, S7 and S8 each represents a hydroxy, C1- 4 alkoxy or aralkoxy group (two adjacent C1- 4 alkoxy groups being joined, if desired, to form a C1- 4 alkylenedioxy group) and the broken lines indicate optional bonds or bonds to optional S groups as the case may require; acid addition salts thereof; and a process for their preparation comprising reacting a heterocyclic amine of the formula R1H, or an acid addition salt thereof, with an epoxide of the formula: <FORM:1032054/C2/3> and where required, reducing any nitro group in the reaction product to an amino group. 1 - (4 - Chlorophenyl) - 1 - methyl - epoxyethane is prepared by reacting chloroacetyl chloride with chlorobenzene in the presence of AlCl3, reacting the resulting 4,22-dichloroacetophenone with methyl magnesium iodide and heating the product with aqueous sodium hydroxide. Pharmaceutical compositions having hypotensive, sedative, antitussive and analgesic activity, for oral or parenteral administration, comprise a compound of the invention together with a pharmaceutical carrier.
GB28568/63A 1963-07-19 1963-07-19 Substituted isoquinoline and piperazine derivatives and a process for the manufacture thereof Expired GB1032054A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
GB28568/63A GB1032054A (en) 1963-07-19 1963-07-19 Substituted isoquinoline and piperazine derivatives and a process for the manufacture thereof
AT569364A AT251582B (en) 1963-07-19 1964-07-02 Process for the preparation of new N-substituted 1,2,3,4-tetrahydroisoquinoline compounds
IL2167464A IL21674A (en) 1963-07-19 1964-07-08 Substituted 1,2,3,4-tetrahydroisoquinoline derivatives
BE650658D BE650658A (en) 1963-07-19 1964-07-16
FR981790A FR4068M (en) 1963-07-19 1964-07-16
FR981789A FR1408958A (en) 1963-07-19 1964-07-16 Process for the preparation of heterocyclic compounds
NL6408192A NL6408192A (en) 1963-07-19 1964-07-17
ES0302224A ES302224A1 (en) 1963-07-19 1964-07-17 Procedure for the manufacture of heterociclic compounds. (Machine-translation by Google Translate, not legally binding)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB28568/63A GB1032054A (en) 1963-07-19 1963-07-19 Substituted isoquinoline and piperazine derivatives and a process for the manufacture thereof

Publications (1)

Publication Number Publication Date
GB1032054A true GB1032054A (en) 1966-06-08

Family

ID=10277676

Family Applications (1)

Application Number Title Priority Date Filing Date
GB28568/63A Expired GB1032054A (en) 1963-07-19 1963-07-19 Substituted isoquinoline and piperazine derivatives and a process for the manufacture thereof

Country Status (7)

Country Link
AT (1) AT251582B (en)
BE (1) BE650658A (en)
ES (1) ES302224A1 (en)
FR (1) FR4068M (en)
GB (1) GB1032054A (en)
IL (1) IL21674A (en)
NL (1) NL6408192A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1079520A (en) * 1965-07-19 1967-08-16 Roche Products Ltd Novel tetrahydro-isoquinoline derivatives and a process for the manufacture thereof
CN108484574B (en) * 2018-04-12 2020-06-19 广东医科大学 Preparation and application of tetrahydroisoquinoline derivative

Also Published As

Publication number Publication date
FR4068M (en) 1966-04-12
BE650658A (en) 1965-01-18
AT251582B (en) 1967-01-10
NL6408192A (en) 1965-01-20
IL21674A (en) 1968-03-28
ES302224A1 (en) 1965-01-16

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