GB722679A - Isonicotinic acid derivatives and process for the manufacture thereof - Google Patents

Isonicotinic acid derivatives and process for the manufacture thereof

Info

Publication number
GB722679A
GB722679A GB6223/53A GB622353A GB722679A GB 722679 A GB722679 A GB 722679A GB 6223/53 A GB6223/53 A GB 6223/53A GB 622353 A GB622353 A GB 622353A GB 722679 A GB722679 A GB 722679A
Authority
GB
United Kingdom
Prior art keywords
compound
phenyl
ketone
prepared
methyl
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
GB6223/53A
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
Publication of GB722679A publication Critical patent/GB722679A/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
    • C07D213/60—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
    • C07D213/86—Hydrazides; Thio or imino analogues thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises chemotherapeutic compounds of the formula <FORM:0722679/IV (b)/1> wherein R stands for a disubstituted methyl- or methylene-amino group in which one substituent is alkyl or phenyl and the other is an isocyclic group, which substituents may be joined to form a ring including the carbon atom of the methyl- or methylene-amino group. The isocyclic group may also contain substituents such as methyl, hydroxy, methoxy or dimethylamino. They may be prepared by reacting isonicotinyl-hydrazine with a ketone R1COR2, wherein R1 and R2 represent the above substituents in the amino group, and, if desired, hydrogenating the product. The reaction is preferably effected at slightly elevated temperatures in a diluent, e.g. a lower alcohol or aqueous alcohol. The hydrogenation is performed in the presence of a catalyst, e.g. platinum oxide. In the examples, (1) 1-isonicotinyl - 2 - (11-phenyl-ethylidene) - hydrazine is prepared using acetophenone as the ketone reagent, and the corresponding ethyl derivative and its dihydrochloride salt are prepared by hydrogenation; (2) 1-isonicotinyl-2-[11-(311,411 dimethoxy - phenyl) - ethylidene] - hydrazine is prepared using 3,4-dimethoxy-acetophenone; (3) the 2-(11-phenyl-n-butylidene) compound is prepared using butyrophenone; (4) the 2-(11-phenyl - n - octylidene) compound using phenyl n-heptyl ketone; (5) the 2-[11-(p-tolyl)-n-hexadecylidene using p-tolyl-n-pentadecyl ketone and the n-hexadecyl derivative by hydrogenation; (6) the 2-[11-(b -naphthyl)-ethylidene] compound using methyl b -naphthyl ketone; (7) the 2-[indanylidene-(11)] compound using indanone-1; (8) the 2-(91-fluorenylidene) compound using fluorenone; (9) the 2-(11-cyclopropyl-ethylidene) compound using methyl cyclopropyl ketone; (10) the 2-(11-decalylidene) compound using a -decalone. Other ketones are mentioned as suitable reagents.
GB6223/53A 1952-03-07 1953-03-06 Isonicotinic acid derivatives and process for the manufacture thereof Expired GB722679A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US722679XA 1952-03-07 1952-03-07

Publications (1)

Publication Number Publication Date
GB722679A true GB722679A (en) 1955-01-26

Family

ID=22106562

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6223/53A Expired GB722679A (en) 1952-03-07 1953-03-06 Isonicotinic acid derivatives and process for the manufacture thereof

Country Status (1)

Country Link
GB (1) GB722679A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2967866A (en) * 1959-04-07 1961-01-10 Commercial Solvents Corp Nu-(p-chlorobenzyl) cycloserine
US2971004A (en) * 1959-04-07 1961-02-07 Commercial Solvents Corp Substituted cycloserines
US3060192A (en) * 1959-04-29 1962-10-23 Olin Mathieson Production of enantiomers of alphamethyl-phenethyl hydrazine and intermediate
US3247057A (en) * 1963-12-16 1966-04-19 Stauffer Chemical Co Inhibiting the growth of bacteria and fungi with application thereto of 2-bromo-indanone-1 or 2, 2-dibromo-indanone-1

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2967866A (en) * 1959-04-07 1961-01-10 Commercial Solvents Corp Nu-(p-chlorobenzyl) cycloserine
US2971004A (en) * 1959-04-07 1961-02-07 Commercial Solvents Corp Substituted cycloserines
US3060192A (en) * 1959-04-29 1962-10-23 Olin Mathieson Production of enantiomers of alphamethyl-phenethyl hydrazine and intermediate
US3247057A (en) * 1963-12-16 1966-04-19 Stauffer Chemical Co Inhibiting the growth of bacteria and fungi with application thereto of 2-bromo-indanone-1 or 2, 2-dibromo-indanone-1

Similar Documents

Publication Publication Date Title
US2710872A (en) Production of esters of dithiocarbamic acid
Rice et al. Raney Nickel catalyzed N-alkylation of aniline and benzidine with alcohols
GB722679A (en) Isonicotinic acid derivatives and process for the manufacture thereof
SU571192A3 (en) Method of preparing apylpyperazine derivatives of adenine
US3969409A (en) 3-Anilino-5,5-disubstituted-2-aminomethyl-2-cyclohexen-1-ones and the salts thereof
US3211778A (en) Method for preparing acrylonitrile derivatives
SU644374A3 (en) Method of obtaining sulfamilbenzylamine derivatives or salts thereof
US3879402A (en) Process for preparing 2-chloro-5-sulfamoylbenzoic acids
US2483436A (en) Thioethers and methods for obtaining the same
Wiley et al. 4 [N, N-Bis (2-haloethyl) amino] benzaldehyde Derivatives
HARVILL et al. The Synthesis of Alkylated Pentamethylenetetrazole Derivatives
Hartwell et al. Some Quaternary Ammonium Salts of Heterocyclic Bases1, 2
US2507647A (en) Synthesis of
Hayes et al. Some Furan Antihistaminic Agents
Cairns et al. Synthesis of Pyrimidines and Pyridines from Acetylene and Nitriles
US2489669A (en) Preparation of 1-alkyl-3-benzoyl-4-hydroxy-4-phenyl-piperidines
US3354161A (en) 8alpha-(4-phenyl-1-piperazyl)-4alpha, 5, 6, 7, 8alpha-hexahydro-4h-1-benzopyrans and process
ES406433A1 (en) Dihydroquinoline derivatives
GRAEF et al. Antitubercular studies. heterocyclic fatty acids
CS101891A2 (en) Method of pyridin and quinoline derivatives preparation
SU545257A3 (en) The method of obtaining 1-substituted pyrazolone-5 or their salts
GB730922A (en) Aromatic amino-ketones and acid addition salts thereof and a process for the manufacture of same
Keilin et al. Deamination of 5-Amino-8-nitroisoquinoline1
JOHNSON et al. 2, 6-Dicyanopiperidines
US3278599A (en) 2-(benzyloxyalkyl)-4-phenylimino-1, 3-cyclopentanedione derivatives