New pyridine carboxamides

Patent metadata

Field	Value
Publication number	US-2020354321-A1
Application number	US-201916966057-A
Country	US
Kind code	A1
Filing date	Jan 29, 2019
Priority date	Feb 7, 2018
Publication date	Nov 12, 2020
Grant date	—

Abstract

The present invention relates to the use of compounds of formula I, wherein the variables are defined as given in the description and claims. The invention further relates to the compounds I and composition for compounds of formula I.

First claim

1 . A compound of formula I

wherein
X is O, S, NH
R 1 is in each case independently selected from hydrogen, halogen, OH, CN, COOH, CONH 2 , NO 2 , SH, NH 2 , NH(C 1 -C 4 -alkyl), N(C 1 -C 4 -alkyl) 2 , NH—SO 2 —R x , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein
R x is C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, unsubstituted aryl or aryl that is substituted by 1, 2, 3, 4 or 5 substituents R′ independently selected from C 1 -C 4 -alkyl, halogen, OH, CN, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -halogenalkoxy;
wherein the acyclic moieties of R 1 are unsubstituted or substituted with identical or different groups R 1a which independently of one another are selected from:
R 1a halogen, OH, CN, COOH, CONH 2 , C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl, C 1 -C 4 -halogenalkoxy, C 1 -C 6 -alkylthio, aryl and phenoxy, wherein the aryl group is unsubstituted or carries 1, 2, 3, 4 or 5 substituents R 11a selected from the group consisting of halogen, OH, C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -halogenalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R 1 are not further substituted or carry 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups R 1b which independently of one another are selected from:
R 1b halogen, OH, CN, COOH, CONH 2 , C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl, C 1 -C 4 -halogenalkoxy and C 1 -C 6 -alkylthio;

R 2 is in each case independently selected from halogen, OH, CN, COOH, CONH 2 , NO 2 , SH, NH 2 , NH(C 1 -C 4 -alkyl), N(C 1 -C 4 -alkyl) 2 , NH(C 2 -C 4 -alkenyl), N(C 2 -C 4 -alkenyl) 2 , NH(C 2 -C 4 -alkynyl), N(C 2 -C 4 -alkynyl) 2 , NH(C 3 -C 6 -cycloalkyl), N(C 3 -C 6 -cycloalkyl) 2 , N(C 1 -C 4 -alkyl)(C 2 -C 4 -alkenyl), N(C 1 -C 4 -alkyl)(C 2 -C 4 -alkynyl), N(C 1 -C 4 -alkyl)(C 3 -C 6 -cycloalkyl), N(C 2 -C 4 -alkenyl)(C 2 -C 4 -alkynyl), N(C 2 -C 4 -alkenyl)(C 3 -C 6 -cycloalkyl), N(C 2 -C 4 -alkynyl)(C 3 -C 6 -cycloalkyl), NH(C(═O)C 1 -C 4 -alkyl), N(C(═O)C 1 -C 4 -alkyl) 2 , NH—SO 2 —R x , S(O) n —C 1 -C 6 -alkyl, S(O) n -aryl, C 1 -C 6 -cycloalkylthio, S(O) n —C 2 -C 6 -alkenyl, S(O) n —C 2 -C 6 -alkynyl, CH(═O), C(═O)C 1 -C 6 -alkyl, C(═O)C 2 -C 6 -alkenyl, C(═O)C 2 -C 6 -alkynyl, C(═O)C 3 -C 6 -cycloalkyl, C(═O)NH(C 1 -C 6 -alkyl), CH(═S), C(═S)C 1 -C 6 -alkyl, C(═S)C 2 -C 6 -alkenyl, C(═S)C 2 -C 6 -alkynyl, C(═S)C 3 -C 6 -cycloalkyl, C(═S)O(C 2 -C 6 -alkenyl), C(═S)O(C 2 -C 6 -alkynyl), C(═S)O(C 3 -C 7 -cycloalkyl), C(═S)NH(C 1 -C 6 -alkyl), C(═S)NH(C 2 -C 6 -alkenyl), C(═S)NH(C 2 -C 6 -alkynyl), C(═S)NH(C 3 -C 7 -cycloalkyl), C(═S)N(C 1 -C 6 -alkyl) 2 , C(═S)N(C 2 -C 6 -alkenyl) 2 , C(═S)N(C 2 -C 6 -alkynyl) 2 , C(═S)N(C 3 -C 7 -cycloalkyl) 2 , C 1 -C 6 -alkyl, C 1 -C 6 -halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, OR′, C 3 -C 6 -cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein
R x is as defined above;
R Y is C 1 -C 6 -alkyl, C 1 -C 6 -halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -halogenalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl, phenyl and phenyl-C 1 -C 6 -alkyl; wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of CN, halogen, OH, C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -halogenalkoxy;
wherein the acyclic moieties of R 2 are unsubstituted or substituted by groups R 2a which independently of one another are selected from:
R 2a halogen, OH, CN, COOH, CONH 2 , C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl, C 1 -C 4 -halogenalkoxy, C 1 -C 6 -alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R 91a selected from the group consisting of halogen, OH, C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -halogenalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R 2 are unsubstituted or substituted by groups R 3b which independently of one another are selected from:
R 2b halogen, OH, CN, COOH, CONH 2 , C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl, C 1 -C 4 -halogenalkoxy and C 1 -C 6 -alkylthio;
and wherein n is defined as above;

R 3 is in each case independently selected from the substituents as defined for R 2 , wherein the possible substituents for R 3 are R 3a and R 3b , respectively, which correspond to R 2a and R 2b , respectively;
R 2 , R 3 together with the carbon atoms to which they are bound form a five-, six-, or seven-membered carbo-, heterocyclic or heteroaromatic ring; wherein the heterocyclic or heteroaromatic ring contains 1, 2, 3 or 4 heteroatoms selected from N, O and S, wherein N may carry one substituent R N selected from C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl and SO 2 Ph, wherein Ph is unsubstituted or substituted by substituents selected from C 1 -C 4 -alkyl, halogen, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkoxy, and CN; and wherein S may be in the form of its oxide SO or SO 2 ; and wherein in each case one or two CH 2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(═O) and C(═S); and wherein the carbo-, heterocyclic or heteroaromatic ring is substituent by (R 23 ) m , wherein m is 0, 1, 2, 3 or 4;
R 23 is in each case independently selected from halogen, OH, CN, COOH, CONH 2 , NO 2 , SH, NH 2 , NH(C 1 -C 4 -alkyl), N(C 1 -C 4 -alkyl) 2 , NH—SO 2 —R x , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl and aryl; wherein the heterocycle and heteroaryl contains 1, 2 or 3 heteroatoms selected from N, O and S; and wherein in each case one or two CH 2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(═O) and C(═S); and wherein
R x is as defined above;
wherein the acyclic moieties of R 23 are unsubstituted or carry 1, 2, 3 or up to the maximum possible number of identical or different groups R 23a which independently of one another are selected from:
R 23a halogen, OH, CN, COOH, CONH 2 , C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl, C 1 -C 4 -halogenalkoxy, C 1 -C 6 -alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R 91a selected from the group consisting of halogen, OH, C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkoxy, CN, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl, C 1 -C 4 -alkylthio;
wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R 23 are unsubstituted or substituted with identical or different groups R 23 which independently of one another are selected from:
R 23b halogen, OH, CN, COOH, CONH 2 , C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl, C 1 -C 4 -halogenalkoxy, and C 1 -C 6 -alkylthio;

R 4 is in each case independently selected from hydrogen, halogen, OH, CN, COOH, CONH 2 , NO 2 , SH, NH 2 , NH(C 1 -C 4 -alkyl), N(C 1 -C 4 -alkyl) 2 , NH—SO 2 —R x , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, five- or six-

Assignees

• Basf Se

Inventors

• Seet Michael
• Wolf Antje
• Mueller Bernd
• Riediger Nadine
• Fehr Marcus
• Mentzel Tobias
• Grote Thomas
• Rudolf Georg Christoph
• Lohmann Jan Klaas
• Winter Christian Harald
• Grammenos Wassilios
• Wiebe Christine
• Terteryan-Seiser Violeta
• Escribano Cuesta Ana

Classifications

• C07D417/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D413/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D409/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D409/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D407/12

  linked by a chain containing hetero atoms as chain links · CPC title