ES427187A1 - Vinylic and acetylenic pyridines and their n-oxides - Google Patents

Vinylic and acetylenic pyridines and their n-oxides

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Publication number
ES427187A1
ES427187A1 ES427187A ES427187A ES427187A1 ES 427187 A1 ES427187 A1 ES 427187A1 ES 427187 A ES427187 A ES 427187A ES 427187 A ES427187 A ES 427187A ES 427187 A1 ES427187 A1 ES 427187A1
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Prior art keywords
see formula
compound
produce
formula
hydrogen
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Expired
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ES427187A
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Spanish (es)
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Merck and Co Inc
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Merck and Co Inc
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Publication of ES427187A1 publication Critical patent/ES427187A1/en
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    • 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
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/32—Sulfur 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
    • C07D213/60—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
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • 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
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • C07D213/66—One oxygen atom attached in position 3 or 5 having in position 3 an oxygen atom and in each of the positions 4 and 5 a carbon atom bound to an oxygen, sulphur, or nitrogen atom, e.g. pyridoxal
    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • 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
    • C07D213/89—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 with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
    • C07D263/36—One oxygen atom
    • C07D263/42—One oxygen atom attached in position 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D497/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D497/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/58—Pyridine rings

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  • Animal Behavior & Ethology (AREA)
  • Pain & Pain Management (AREA)
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  • Medicinal Chemistry (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

A procedure for the preparation of a compound of structural formula: **(See formula)** or pharmaceutically acceptable salts thereof, where m is 0 or 1; x is an integer from 0 to 3; A is (see formula) where R7 is hydrogen, chlorine or fluorine; R1 and R2 are hydrogen or C1-3 alkyl; R3 is (a) hydrogen, (b) -SO3H, (c) -PO3H2, (d) amidino, (e) N (C1-4-alkyl), (f) -CH2CH (NH2) COOH, (g) ethoxycarbonylmethyl, (h) (see formula), where E represents (1) adamantyl, (2) C3-8 cycloalkyl (3) C1-5 alkoxy, (4) C2-6 alkyl, (5) N (C1-4 alkyl), 2, (6) phenyl, (7) 2-acetoxyphenyl, (8) 2-hydroxy-4- (2,4-difluorophenyl) phenyl, (9) 3-chloro-4-allyloxybenzyl (10) α-methyl-4-isobutylbenzyl, (11) α-methyl-3-phenoxybenzyl, (12) α-methyl-3-benzoylbenzyl (13) 1- (6-methoxynaft-2-yl) ethyl, (14) α-methyl-3-fluoro-4-phenylbenzyl, (15) 2- (3-chloro-4-cyclohexylbenzoyl) -ethyl, (16) 2- (3-trifluoromethylanilino) phenyl, (17) 2- (2,3-dimethylanilino) phenyl, (18) 2- (2,6-dichloro-3-methylanilino) phenyl, (19) 2- (3-trifluoromethylanilino) -3-pyridyl, (20) 2- (2-methyl-3-chloroanilino) -3-pyridyl or (i) (see formula), (j) **(See formula)** (k) (see formula), where G represents (1) C1-4 alkoxy, (2) -S (alkali metal) or (3) **(See formula)** (l) (see formula), where L represents (1) - (CH2) 1-5-, (2) phenylene or (3) (see formula), (m) -S-R8, where R8 represents (1) -C (CH3) 2CH (NH2) COOH, (2) C1-5 alkyl, (3) C2-5 alkenyl, (4) phenylalkyl - (C1-3), (5) phenyl, (6) C2-5 alkynyl, (7) 2- carboxyphenyl or (8) **(See formula)** (n) (see formula) (o) (see formula); (p) **(See formula)** R4 is hydrogen, C1-3alkyl, phenyl, chlorine, carboxy, (C1-3) alkoxycarbonyl, fluorine and R is (a) C1-3 alkyl, (b) hydroxy, (c) **(See formula)** (d) C1-3 hydroxyalkyl and (e) when a radical R is hydroxy adjacent to the group (see formula), oxygen and sulfur thereof can be linked together through a group of formula: **(See formula)** where R5 and R5α are the same or different and each represents hydrogen, C1-6 alkyl, phenyldimethylphenyl or difluorfluorophenyl or, taken together, R5 and R5α represent = O or = S, whose procedure is characterized in that a compound of structural formula: **(See formula)** where m, x, A, R1, R2, R4 and R are as defined above and Q is chlorine, bromine, iodine, methanesulfonyloxy, toluenesulfonyloxy, benzosulfonyloxy or 2,4-dinitrobenzoyloxy, treated with (a) sodium thiosulfate to form the product where R3 is -SO3H; followed, if desired, by treatment with (1) an alkali metal hydroxide and a compound of the formula R8SH, where R8 is -C (CH3) 2CH (NH2) COOH, C1-5 alkyl, C2-5 alkenyl, phenyl (C1-3) alkyl, phenyl, C2 alkynyl -5 or 2-carboxyphenyl to produce the compound where R3 is -SR8, (2) an alkali metal hydroxide and a compound of the formula: **(See formula)** to produce the compound where R3 is: **(See formula)** (3) an alkali metal hydroxide or a mineral acid to produce the compound where R3 is **(See formula)** (4) a reducing agent to produce the compound where R3 is hydrogen; (5) Na2S2 or Na2S to produce the compound where R3 is **(See formula)** (6) iodine to produce the compound where R3 is **(See formula)** (b) an alkali metal trithiocarbonate to produce the compound where R3 is **(See formula)** followed if desired by treatment with an alkali and/or an acid to produce the compound where R3 is hydrogen; (c) trisodium phosphorothioate and a mineral acid to produce the compound where R3 is -PO3H2; (d) thiourea or (C1-4) alkyl potassium xanthogenate to produce the compound where Q is (see formula) or (see formula) respectively, followed if desired by treatment with (1) when Y is (see formula), an alkali metal hydroxide or a reducing agent to produce the compound where R3 is hydrogen; (2) when Y is (see formula), an alkali metal hydroxide and an oxidizing agent to produce the compound where R3 is **(See formula)** (3) when Y is (see formula), an alkali metal hydroxide or a reducing agent to produce the compound where R3 is hydrogen (4) when Y is (see formula), with ammonium hydroxide or ammonium hydroxide and an oxidizing agent to produce the compound where R3 is **(See formula)** (e) potassium thioacyloate to produce the compound where R3 is acyl, followed if desired by treatment with an alkali to produce the compound where R3 is hydrogen; (f) Na2S2 to produce the compound where R3 is **(See formula)** (g) HSCH2CO2Et or (see formula) to produce the compound where R3 is -CH2CO2Et or (see formula) respectively; or when at least one R os hydroxy group and the group (see formula), where Q is -OH, is adjacent thereto and is in position 2, 4 or 6, by treatment with carbon disulfide and an alkali metal hydroxide to produce the compound where R3 is hydrogen; or when Q is -OH, by treatment with P2S5 to produce the compound where R3 is **(See formula)** (h) the product from Stage A (4) is treated with: (1) a compound of formula (see formula) or (see formula), where the halogen is chlorine or bromine to produce the compound where R3 is (see formula), where E is the one previously defined; (2) cyanogen bromide and di (C1-4alkyl) amine to produce the compound where R3 is -N (C1-4alkyl) 2; (3) phosgene to produce the compound where R3 is **(See formula)** (4) phosgene and NH2CH2CO2 (C1-4alkyl) or ammonia to produce the compound where R3 is (see formula), respectively; (5) a compound of formula (see formula) where L is - (CH2) 1-5 phenylene or (see formula) and the halogen is chlorine or bromine, to produce the compound where R3 is **(See formula)** (6) o-carboxyphenyl o-carboxybenzothiolsulfonate to produce the compound where R3 is **(See formula)** (7) S-thiamine monoxide to produce the compound where R3 is **(See formula)** (8) sulfur dichloride and sulfur monochloride to produce the compound where R3 is **(See formula)** respectively, (9) an oxidizing agent to produce the compound where R3 is **(See formula)** (10) when R3 is adjacent to a hydroxyl group, by treatment with a compound of formula: **(See formula)** where R5 and R5α are the same or different and each is hydrogen, C1-5 alkyl, phenyl, dimethylphenyl or difluorophenyl or, taken together, R5 and R5α represent = O or = S and the reagent is of formula **(See formula)** to produce the compound where the hydroxy group and the group (see formula) are linked together through a group of formula: **(See formula)** (i) reduce a compound where R3 is **(See formula)** to form the compound where R3 is hydrogen or (j) an alkali metal hydrosulfide to form the product where R3 is hydrogen. (Machine-translation by Google Translate, not legally binding)
ES427187A 1973-06-15 1974-06-11 Vinylic and acetylenic pyridines and their n-oxides Expired ES427187A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US36877273A 1973-06-15 1973-06-15
US46177874A 1974-04-18 1974-04-18
US46401174A 1974-04-26 1974-04-26

Publications (1)

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ES427187A1 true ES427187A1 (en) 1977-01-01

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ES427187A Expired ES427187A1 (en) 1973-06-15 1974-06-11 Vinylic and acetylenic pyridines and their n-oxides

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JP (1) JPS59511B2 (en)
CA (1) CA1021342A (en)
CH (1) CH605764A5 (en)
DE (1) DE2428470A1 (en)
DK (1) DK148594C (en)
EG (1) EG11578A (en)
ES (1) ES427187A1 (en)
FI (1) FI167474A (en)
FR (1) FR2233055B1 (en)
GB (1) GB1473591A (en)
IE (1) IE39896B1 (en)
IL (1) IL44958A (en)
LU (1) LU70318A1 (en)
NL (1) NL187395C (en)
NO (1) NO144569C (en)
SE (2) SE411208B (en)
ZM (1) ZM9274A1 (en)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3290319A (en) * 1965-02-26 1966-12-06 Bristol Myers Co Substituted carbamates of pyridine 2, 6-dimethanethiols
US3591584A (en) * 1968-08-27 1971-07-06 Pfizer Benzothiazine dioxides
DE2161403A1 (en) * 1970-12-17 1972-07-06 Hidaka, Hiroyoshi, Nagoya, Aichi (Japan) Pyridine carbamate derivatives and processes for making the same

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Publication number Publication date
NO144569B (en) 1981-06-15
CH605764A5 (en) 1978-10-13
IE39896B1 (en) 1979-01-31
JPS5040574A (en) 1975-04-14
AU6976574A (en) 1975-12-04
LU70318A1 (en) 1975-03-06
SE411208B (en) 1979-12-10
NL7407212A (en) 1974-12-17
DK148594B (en) 1985-08-12
DE2428470A1 (en) 1975-01-23
IL44958A0 (en) 1974-09-10
SE7406972L (en) 1974-12-16
EG11578A (en) 1978-03-29
IE39896L (en) 1974-12-15
FR2233055B1 (en) 1977-11-04
NL187395C (en) 1991-09-16
JPS59511B2 (en) 1984-01-07
NO144569C (en) 1981-09-23
DK290274A (en) 1975-02-10
ZM9274A1 (en) 1976-02-23
CA1021342A (en) 1977-11-22
SE7711211L (en) 1977-10-06
FI167474A (en) 1974-12-16
GB1473591A (en) 1977-05-18
DE2428470C2 (en) 1988-10-13
NO741962L (en) 1975-01-13
NL187395B (en) 1991-04-16
IL44958A (en) 1978-09-29
SE426170B (en) 1982-12-13
FR2233055A1 (en) 1975-01-10
DK148594C (en) 1986-01-27

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