GB1005025A - Naphthalene derivatives - Google Patents

Naphthalene derivatives

Info

Publication number
GB1005025A
GB1005025A GB46034/61A GB4603461A GB1005025A GB 1005025 A GB1005025 A GB 1005025A GB 46034/61 A GB46034/61 A GB 46034/61A GB 4603461 A GB4603461 A GB 4603461A GB 1005025 A GB1005025 A GB 1005025A
Authority
GB
United Kingdom
Prior art keywords
stands
radical
alkyl
substituted
naphthyl
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
GB46034/61A
Inventor
Albert Frederick Crowther
Ralph Howe
Leslie Harold Smith
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries 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 to BE626434D priority Critical patent/BE626434A/xx
Priority to NL287141D priority patent/NL287141A/xx
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB46034/61A priority patent/GB1005025A/en
Priority to DK551263A priority patent/DK105535C/en
Priority to DK551363A priority patent/DK104631C/en
Priority to AT1002362A priority patent/AT238714B/en
Priority to AT247664A priority patent/AT238715B/en
Priority to AT247864A priority patent/AT240848B/en
Priority to AT247764A priority patent/AT245564B/en
Priority to DK558562A priority patent/DK104309C/en
Priority to ES283604A priority patent/ES283604A1/en
Priority to DK551163A priority patent/DK105534C/en
Priority to FR919606A priority patent/FR1516716A/en
Priority to FR928815A priority patent/FR3913M/fr
Publication of GB1005025A publication Critical patent/GB1005025A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • 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
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • 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
    • C07D295/092—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 with aromatic radicals attached to the chain
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • 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
    • C07D317/44—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 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—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 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58—Radicals substituted by nitrogen atoms

Landscapes

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

Abstract

The invention comprises racemic compounds of the general formula <FORM:1005025/C2/1> wherein R1 stands for a hydrogen atom or a straight- or branched-chain alkyl radical of not more than six carbon atoms, R2 stands for an alkyl radical of more than four carbon atoms, a substituted alkyl radical, a cycloalkyl radical, optionally substituted, or an alkenyl radical, optionally substituted, or R1 and R2 are joined together with the adjacent nitrogen atom to form a heterocyclic radical, optionally substituted, and wherein the naphthalene nucleus may optionally bear one or more alkyl substituents, and the acid addition salts thereof, but excluding 1 - (2 - naphthyl) - 2 - benzylaminoethanol, 1 - (2 - naphthyl) - 2 - (2 - phenylethylamino)-ethanol, 1 - (2 - naphthyl) - 2 - cyclohexyl-aminoethanol, 1 - (2-naphthyl)-2-[2-(1,2,3,4-tetrahydronaphthyl)]aminoethanol, 1 - (2 - naphthyl) - 2 - piperidinoethanol, 1 - (2 - naphthyl) - 2 - morpholinoethanol and 1 - (2 - naphthyl) - 2 - [N - (1,2,3,4-tetrahydroisoquinolyl)] -ethanol, and the acid addition salts thereof, pharmaceutical preparations containing them, and their preparation by (a) reducing a compound of the formula <FORM:1005025/C2/2> (wherein X stands for a halogen atom and the naphthalene nucleus may optionally bear one or more alkyl substituents) and reacting the product with NHR1R2, (b) reacting a compound of the formula <FORM:1005025/C2/3> (wherein R stands for the group <FORM:1005025/C2/4> or -CHOH.CH2X and the naphthalene nucleus may optionally bear one or more alkyl substituents) with NHR1R2, (e) reducing a compound of the formula <FORM:1005025/C2/5> (wherein the naphthalene nucleus may optionally bear one or more alkyl substituents) or an acid addition salt thereof, provided that when R2 in the starting material stands for an alkyl radical substituted on the carbon atom adjacent to the nitrogen atom by an aryl, substituted aryl or heterocyclic radical the starting material is used in the free base form, (d)-in the case of compounds wherein R1 stands for a hydrogen atom and R2 stands for -CHR3R4, wherein R3\h stands for a hydrogen atom or an alkyl radical and R4 stands for an alkyl radical, provided that R3 and R4 together contain more than three carbon atoms, or wherein R3 stands for a hydrogen atom or an alkyl or substituted alkyl radical and R4 stands for an alkyl, substituted alkyl or aryl radical, optionally substituted, provided that R3 or R4 or both stands, or stand, for an alkyl radical or radicals, bearing at least one substituent or R4 stands for an aryl radical, optionally substituted, or wherein R3 stands for a hydrogen atom or an alkyl, substituted alkyl, alkenyl, substituted alkenyl, aryl or substituted aryl radical and R4 stands for an alkenyl or substituted alkenyl radical, or wherein R3 and R4 are joined to form together with the adjacent carbon atom a cycloalkyl radical, optionally substituted-reacting a compound (which may be generated in situ) of the formula <FORM:1005025/C2/6> (wherein A stands for the group CO or CHOH and the naphthalene nucleus may optionally bear one or more alkyl substituents) with R3.CO.R4 under reducing conditions, (e)-in the case of compounds wherein R1 stands for a hydrogen atom and R2 stands for -CHR3R4-reducing a compound of the formula <FORM:1005025/C2/7> (wherein the naphthalene nucleus may optionally bear one or more alkyl substituents) in the presence of R3.CO.R4, (f) reducing a compound of the formula <FORM:1005025/C2/8> (wherein R5 stands for an aldehydo radical or a radical of the formula -CH(OR6)OH, wherein R6 stands for a hydrogen atom or an alkyl radical of not more than six carbon atoms, and the naphthalene nucleus may optionally bear one or more alkyl substituents) in the presence of NHR1R2 or an acid addition salt thereof, (g)-in the case of compounds wherein -NR1R2 stands for a heterocyclic radical, optionally substituted-reducing a compound of the formula <FORM:1005025/C2/9> (wherein <FORM:1005025/C2/100> stands for a heterocyclic radical containing at least one carbonyl radical in the ring and the naphthalene nucleus may optionally bear one or more alkyl substituents) or an acid addition salt thereof, or (h)-in the case of compounds wherein R1 stands for a hydrogen atom and R2 stands for an alkyl radical of more than four carbon atoms or a substituted alkyl radical-reducing the corresponding compound wherein R2 stands for an alkenyl or substituted alkenyl radical, optionally followed in each case by acid addition salt formation and/or (in the case of compounds wherein R1 or R2 contains one or more elements of asymmetry) separation of a mixture of two or more racemic diastereoisomeric mixtures into individual racemic mixtures. The following intermediates are prepared from the starting materials indicated in parentheses: 2 - naphthylglyoxal hydrate (2 -naphthacyl bromide); 1 - (2 - naphthyl) - 2 - (2 - methyl - N - pyrrolid - 5 - onyl)ethanol (1 - (2 naphthyl) - 2 - aminoethanol and ethyl laevulinate); 2 - methoxy - 2 - (3 - methoxyphenyl)-ethylamine and its hydrochloride (3 - methoxy - b - nitrostyrene, via 1-(3-methoxyphenyl)-2-nitroethyl methyl ether); 2-(1-methyl-2-phenyl-ethylaminoacetyl)naphthalene hydrobromide (2 - naphthacyl bromide and 1-methyl-2-phenyl-ethylamine); 6-methyl-2-naphthacyl bromide (6-methyl-2-acetonaphthone). The compounds of the invention are of value in the treatment of prophylaxis of coronary artery disease and may be administered in the form of pharmaceutical preparations (e.g. tablets, capsules, aqueous or oily solutions, aqueous or oily suspensions, emulsions, injectable aqueous or oily solutions or suspensions, and dispersible powders) containing them together with a diluent or carrier. Specification 909,357 is referred to.
GB46034/61A 1961-12-22 1961-12-22 Naphthalene derivatives Expired GB1005025A (en)

Priority Applications (14)

Application Number Priority Date Filing Date Title
BE626434D BE626434A (en) 1961-12-22
NL287141D NL287141A (en) 1961-12-22
GB46034/61A GB1005025A (en) 1961-12-22 1961-12-22 Naphthalene derivatives
AT247864A AT240848B (en) 1961-12-22 1962-12-21 Process for the preparation of new 1- (β-naphthyl) -2-aminoethanol derivatives and salts of these compounds
DK551363A DK104631C (en) 1961-12-22 1962-12-21 Process for the preparation of 1- (2-naphthyl) -2-aminoethanol derivatives or salts thereof.
AT1002362A AT238714B (en) 1961-12-22 1962-12-21 Process for the preparation of new 1- (β-naphthyl) -2-aminoethanol derivatives and salts of these compounds
AT247664A AT238715B (en) 1961-12-22 1962-12-21 Process for the preparation of new 1- (β-naphthyl) -2-aminoethanol derivatives and salts of these compounds
DK551263A DK105535C (en) 1961-12-22 1962-12-21 Process for the preparation of 1- (2-naphthyl) -2-aminoethanol derivatives or salts thereof.
AT247764A AT245564B (en) 1961-12-22 1962-12-21 Process for the preparation of new 1- (β-naphthyl) -2-aminoethanol derivatives
DK558562A DK104309C (en) 1961-12-22 1962-12-21 Process for the preparation of 1- (2-naphthyl) -2-aminoethanol derivatives or salts thereof.
ES283604A ES283604A1 (en) 1961-12-22 1962-12-21 Procedure for the obtaining of naftalene derivatives (Machine-translation by Google Translate, not legally binding)
DK551163A DK105534C (en) 1961-12-22 1962-12-21 Process for the preparation of 1- (2-naphthyl) -2-aminoethanol derivatives or salts thereof.
FR919606A FR1516716A (en) 1961-12-22 1962-12-22 Naphthalene derivatives and their manufacturing process
FR928815A FR3913M (en) 1961-12-22 1963-03-21

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB46034/61A GB1005025A (en) 1961-12-22 1961-12-22 Naphthalene derivatives

Publications (1)

Publication Number Publication Date
GB1005025A true GB1005025A (en) 1965-09-22

Family

ID=10439573

Family Applications (1)

Application Number Title Priority Date Filing Date
GB46034/61A Expired GB1005025A (en) 1961-12-22 1961-12-22 Naphthalene derivatives

Country Status (6)

Country Link
AT (2) AT240848B (en)
BE (1) BE626434A (en)
ES (1) ES283604A1 (en)
FR (1) FR3913M (en)
GB (1) GB1005025A (en)
NL (1) NL287141A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5770615A (en) * 1996-04-04 1998-06-23 Bristol-Myers Squibb Company Catecholamine surrogates useful as β3 agonists
US5776983A (en) * 1993-12-21 1998-07-07 Bristol-Myers Squibb Company Catecholamine surrogates useful as β3 agonists

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108653736A (en) * 2018-04-28 2018-10-16 中国人民解放军第二军医大学 Application of the M2 types pyruvate kinase as drug target in the drug for preparing prevention psoriasis

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5776983A (en) * 1993-12-21 1998-07-07 Bristol-Myers Squibb Company Catecholamine surrogates useful as β3 agonists
US5770615A (en) * 1996-04-04 1998-06-23 Bristol-Myers Squibb Company Catecholamine surrogates useful as β3 agonists

Also Published As

Publication number Publication date
AT240848B (en) 1965-06-25
AT238714B (en) 1965-02-25
NL287141A (en)
FR3913M (en) 1966-02-14
ES283604A1 (en) 1963-05-01
BE626434A (en)

Similar Documents

Publication Publication Date Title
GB1058822A (en) 3-amino-2-hydroxypropoxy heterocyclic derivatives
GB1034939A (en) Isoxazole derivative and processes for its production
GB989013A (en) New guanidines and process for their manufacture
GB1005025A (en) Naphthalene derivatives
ES391633A1 (en) 2,2,-diaryl-4-4-aryl-4-hydroxy-piperidino butyramides
GB831920A (en) New phenthiazine derivatives and processes for their preparation
GB1024643A (en) Optically active naphthalene derivatives
GB872943A (en) Improvements in and relating to derivatives of cyclopropane
GB1059968A (en) Naphthalene derivatives
GB810304A (en) Improvements in or relating to amines
GB1046001A (en) Propanolamine derivatives
GB959203A (en) Indole derivatives and salts thereof
Kerwin et al. Adrenergic Blocking Agents. I. N-(9-Fluorenyl)-β-chloroethylamine Series1
GB1080496A (en) Improvements in or relating to a new derivatives of 2,4,6-triiodo-3-hydroxy-benzene and process for preparing the same
US3085094A (en) Heterocyclic compounds
GB1019225A (en) Aminoethanol derivatives
GB729967A (en) Isonicotinic acid derivatives and process for the manufacture thereof
GB871235A (en) Novel substituted pyrrolidones and salts thereof and a process for the manufacture of same
GB1193534A (en) Novel Benzazocine Derivatives, the Preparation thereof and Compositions Containing the same
GB876678A (en) Organic salts of substituted quinolines and process for the manufacture thereof
GB1079747A (en) Alkene derivatives
GB920859A (en) Substituted triphenylmethanols
US2925420A (en) Piperazine derivatives
ES412484A1 (en) Procedure for the preparation of carbostirilic derivatives. (Machine-translation by Google Translate, not legally binding)
GB937878A (en) N-[5-nitro-(2)-furfurylidene]-pyrazole-carboxylic acid hydrazides and process for their manufacture