ES348464A1 - Benzylpyridinium compounds and a process for their production - Google Patents

Benzylpyridinium compounds and a process for their production

Info

Publication number
ES348464A1
ES348464A1 ES348464A ES348464A ES348464A1 ES 348464 A1 ES348464 A1 ES 348464A1 ES 348464 A ES348464 A ES 348464A ES 348464 A ES348464 A ES 348464A ES 348464 A1 ES348464 A1 ES 348464A1
Authority
ES
Spain
Prior art keywords
prepared
ether
compounds
hbr
benzyl
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
ES348464A
Other languages
Spanish (es)
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.)
Novartis AG
Original Assignee
JR Geigy 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 JR Geigy AG filed Critical JR Geigy AG
Publication of ES348464A1 publication Critical patent/ES348464A1/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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/53—Nitrogen atoms
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/48—Aldehydo radicals
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/51—Acetal radicals
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine

Landscapes

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

Abstract

The invention comprises compounds of formula wherein X is Cl or Br R 1 is H or R(=C 1-6 alkyl) or in the 3- or 5-positions OH, OR, aralkoxy or aryloxy R 2 is H, R, OR, F, Cl, Br, NO2, OH, CF 3 , CO 2 alkyl or CN R 3 is as R 2 except OH R 4 is as R 3 except R R 6 is H, OR, F, Cl, Br or NO 2 R 6 is H or (when R 2 = R 3 = R 4 = R 5 = F) F R 7 is H, R, Ph (optionally R- or halogen-substituted), aralkyl, carboalkoxy or 2-pyridyl, and R 8 is OH, OR, aralkoxy or -NHCONH 2 , with the provisos that (1) at least one of R 2 -R 5 is not H (2) when R 2 is Me, at least one of R 2 -R 5 is not H (3) when -CR 7 =NR 8 is in the 2-position and (a) if R 3 is OR, at least one of R 2 , R 4 and R 5 is not H, and (b) if R 2 and R 5 are both OR, at least R 3 or R 4 is not H. These compounds are prepared by reacting together the corresponding (i) 1- benzylacylpyridinium salt and NH 2 OH, its O- ether or NH 2 NHCONH 2 or (ii) benzyl halide and acylpyridine-oxime (or it O-ether) or -semicarbazone. Starting materials.-Alkoxy-substituted benzyl bromides are prepared by reacting the alkoxysubstituted benzene with CH 2 O/HBr or with MeOCH 2 Br (made from MeOH, CH 2 O and HBr), or the benzyl alcohol with HBr 4- chlorobenzyl bromide is prepared similarly. 5-Ethyl-2-formylpyridine is prepared by oxidizing 5-ethyl-2-methylpyridine with H 2 O 2 /HOAc, reacting the product with Ac 2 O and again oxidizing with H 2 O 2 /HOAc. 3-Methylcatechol diethyl ether is prepared from the phenol with Et 2 SO 4 4-isopropylcatechol dimethyl ether is prepared analogously. 2,5-Dimethoxybenzyl alcohol is prepared by reducing the aldehyde with t - butylborane. 1 - (2 - Methyl - 3,4 - dimethoxybenzyl) -2-formylpyridinium bromide is made from the benzyl bromide and 2-formylpyridine. Therapeutic compositions for treating cardiovascular disorders, particularly for lowering blood pressure, comprise compounds of the above general formula, and may be administered orally, rectally or parenterally.
ES348464A 1966-12-21 1967-12-20 Benzylpyridinium compounds and a process for their production Expired ES348464A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US60341866A 1966-12-21 1966-12-21
US68531767A 1967-11-24 1967-11-24

Publications (1)

Publication Number Publication Date
ES348464A1 true ES348464A1 (en) 1969-06-16

Family

ID=27084423

Family Applications (1)

Application Number Title Priority Date Filing Date
ES348464A Expired ES348464A1 (en) 1966-12-21 1967-12-20 Benzylpyridinium compounds and a process for their production

Country Status (13)

Country Link
AT (1) AT278783B (en)
BE (1) BE708316A (en)
CH (1) CH487154A (en)
DE (1) DE1695101A1 (en)
DK (1) DK118876B (en)
ES (1) ES348464A1 (en)
FR (2) FR1550578A (en)
GB (1) GB1210519A (en)
GR (1) GR37786B (en)
IL (1) IL29176A (en)
NL (2) NL6717412A (en)
NO (1) NO123894B (en)
SE (1) SE337373B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1600969A (en) * 1977-01-07 1981-10-21 Acf Chemiefarma Nv Heterocyclic compounds
NL7905789A (en) * 1979-07-26 1981-01-28 Tno 1-SUBSTITUTED-HYDROXYIMINOMETHYL-PYRIDINIUM SALTS, METHOD FOR PREPARING THESE COMPOUNDS, PREPARATIONS AGAINST ORGANO-PHOSPHATE POISONING, AND METHOD FOR PREPARING SUCH PREPARATION.
US5206371A (en) * 1990-08-10 1993-04-27 Georgia Tech Research Corporation Quaternary pyridinium compounds

Also Published As

Publication number Publication date
NL6717413A (en) 1968-06-24
FR1550578A (en) 1968-12-20
CH487154A (en) 1970-03-15
IL29176A (en) 1972-08-30
NL6717412A (en) 1968-06-24
FR7308M (en) 1969-09-29
DE1695101A1 (en) 1971-03-18
GR37786B (en) 1969-07-15
BE708316A (en) 1968-06-20
NO123894B (en) 1972-01-31
GB1210519A (en) 1970-10-28
AT278783B (en) 1970-02-10
SE337373B (en) 1971-08-09
DK118876B (en) 1970-10-19

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