Bicyclic compounds

Patent metadata

Field	Value
Publication number	US-11570992-B2
Application number	US-201716089732-A
Country	US
Kind code	B2
Filing date	Mar 29, 2017
Priority date	Apr 1, 2016
Publication date	Feb 7, 2023
Grant date	Feb 7, 2023

Abstract

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

First claim

The invention claimed is:

1. A compound of formula (I) selected from the group consisting of a compound of formula (I-A) or (I-B):

wherein
X is O or S;
R x , R y independently of each other are selected from the group consisting of C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkoxy-C 1 -C 4 -alkyl, which are unsubstituted or substituted by halogen; C(O)—OR a , NR b R c , C 1 -C 6 -alkylen-NR b R c , O—C 1 -C 6 -alkylen-NR b R c , C 1 -C 6 -alkylen-CN, NH—C 1 -C 6 -alkylen-NR b R c , C(O)—NR b R c , C(O)—R d , SO 2 NR b R c , S(═O) m R c ; phenyl and benzyl, wherein the phenyl ring is unsubstituted or substituted by radicals R f ;
R 1 is partially or fully halogenated C 1 -C 6 -alkyl, partially or fully halogenated C 1 -C 6 -alkoxy, partially or fully halogenated C 2 -C 6 -alkenyl, partially or fully halogenated C 2 -C 6 -alkynyl, partially or fully halogenated C 3 -C 6 -cycloalkyl, partially or fully halogenated C 3 -C 6 -cycloalkoxy, partially or fully halogenated C 1 -C 6 -sulfenyl, partially or fully halogenated C 1 -C 6 -sulfinyl, or partially or fully halogenated C 1 -C 6 -sulfonyl;
R 2 , R 3 , R 4 independently of each other are selected from the group consisting of H, halogen, N 3 , CN, NO 2 , —SCN, —SF 5 , C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, tri-C 1 -C 6 -alkylsilyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkoxyx-C 1 -C 4 -alkyl, which are unsubstituted or substituted by halogen, C(O)—OR a , NR b R c , C 1 -C 6 -alkylen-NR b R c , O—C 1 -C 6 -alkylen-NR b R c , C 1 -C 6 -alkylen-CN, NH—C 1 -C 6 -alkylen-NR b R c , C(O)—NR b R c , C(O)—R d , SO 2 NR b R c and S(═O) m R c , phenyl which is unsubstituted or substituted by radicals R f , phenoxy which is unsubstituted or substituted by radicals R f , phenylcarbonyl which is unsubstituted or substituted by radicals R f , phenylthio which is unsubstituted or substituted by radicals R f , or benzyl which is unsubstituted or substituted by radicals R f ;
Ar is phenyl or 5- or 6-membered heteroaryl, which are unsubstituted or substituted by radicals R Ar , which are identical or different, wherein
R Ar independently of each other, are selected from the group consisting of halogen, N 3 , OH, CN, NO 2 , —SCN, —SF 5 , C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, tri-C 1 -C 6 -alkylsilyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkoxy-C 1 -C 4 -alkyl, which are unsubstituted or substituted by halogen, C(O)—OR a , NR b R c , C 1 -C 6 -alkylen-NR b R c , O—C 1 -C 6 -alkylen-NR b R c , C 1 -C 6 -alkylen-CN, NH—C 1 -C 6 -alkylen-NR b R c , C(O)—NR b R c , C(O)—R d , SO 2 NR b R c and S(═O) m R e , phenyl which is unsubstituted or substituted by radicals R f , phenoxy which is unsubstituted or substituted by radicals R f , phenylcarbonyl which is unsubstituted or substituted by radicals R f , phenylthio which is unsubstituted or substituted by radicals R f , or benzyl which is unsubstituted or substituted by radicals R f ;
each R a is selected from H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkoxy-C 1 -C 4 -alkyl, which are unsubstituted or substituted by halogen, C 1 -C 6 -alkylen-NR b R c , C 1 -C 6 -alkylen-CN, phenyl and benzyl, wherein the phenyl ring is unsubstituted or substituted by radicals R f ;
each R b is selected from H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkoxy-C 1 -C 4 -alkyl, which are unsubstituted or substituted by halogen, C 1 -C 6 -alkylen-CN, phenyl and benzyl, wherein the phenyl is unsubstituted or substituted by radicals R f ;
each R c is selected from H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkoxy-C 1 -C 4 -alkyl, which are unsubstituted or substituted by halogen,
C 1 -C 6 -alkylen-CN, phenyl and benzyl, wherein the phenyl ring is unsubstituted or substituted by radicals R f ;
each moiety NR b R c may also form an N-bound, saturated 5- to 8-membered heterocycle, which in addition to the nitrogen atom may have 1 or 2 further heteroatoms or heteroatom moieties selected from O, S(═O) m and N—R′, wherein R′ is H or C 1 -C 6 -alkyl and wherein the N-bound heterocycle is unsubstituted or substituted by radicals selected from halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy;
each R d is selected from H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkoxy-C 1 -C 4 -alkyl, which are unsubstituted or substituted by halogen, phenyl and benzyl, wherein the phenyl ring is unsubstituted or substituted by radicals R f ;
each R e is selected from C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, which are unsubstituted or substituted by halogen, phenyl and benzyl, wherein the phenyl ring is unsubstituted or substituted by R f ;
each R f is selected from halogen, N 3 , OH, CN, NO 2 , SCN, SF 5 , C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy-C 1 -C 4 alkyl, C 1 -C 6 alkoxy-C 1 -C 4 alkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl, C 3 -C 6 cycloalkoxy-C 1 -C 4 alkyl, which are unsubstituted or substituted by halogen;
m is 0, 1 or 2;
and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.

2. The compound of formula (I-A) according to claim 1 , wherein
R x is selected from C 1 -C 3 alkyl, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, C 3 -C 6 cycloalkyl, and C 1 -C 3 haloalkyl;
R 1 is selected from partially or fully halogenated C 1 -C 6 alkyl, partially or fully halogenated C 1 -C 6 sulfenyl, partially or fully halogenated C 1 -C 6 sulfinyl, and partially or fully halogenated C 1 -C 6 sulfonyl;
R 2 is selected from H, CH 3 , C 2 H 5 , n-propyl, isopropyl, cyclopropyl, allyl and propargyl;
R 4 is selected from H, CH 3 , C 2 H 5 , n-propyl, isopropyl, cyclopropyl, allyl and propargyl;
Ar is a phenyl or 5- or 6-membered heteroaryl substituted with R Ar ,
R Ar is selected from halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, S(═O) m R e , phenyl, phenoxy, phenylcarbonyl, phenylthio and benzyl, wherein the phenyl ring is unsubstituted or substituted by radicals R f ;
R e is selected from C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 haloalkyl, and C 3 -C 6 halocycloalkyl;
R f is selected from Cl, F, Br, OCH 3 , OC 2 H 5 , SCH 3 , SC 2 H 5 , CN, CH 3 , C 2 H 5 , n-propyl, isopropyl, cyclopropyl, allyl, propargyl, CF 3 , CHF 2 , and CF 2 CF 3 .

3. The compound of formula (I-A) according to claim 1 , wherein
R x is CH 3 or C 2 H 5 ;
R 1 is selected from CF 3 , CF 2 CF 3 , CF(CF 3 ) 2 , SCF 3 , OCF 3 , OCHF 2 , S(═O)CF 3 , and S(═O) 2 CF 3 ;
R 2 is selected from H, CH 3 , and C 2 H 5 ;
R 4 is selected from H, CH 3 , and C 2 H

Assignees

• Basf Se

Inventors

• Narine Arun
• Adisechan Ashokkumar
• Chaudhuri Rupsha
• Datta Gopal Krishna
• Sambasivan Sunderraman
• Vyas Devendra

Classifications

• A61P33/10

  Anthelmintics · CPC title

• A01N43/90 Primary

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title

• C07D487/04 Primary

  Ortho-condensed systems · CPC title

• C07D471/04 Primary

  Ortho-condensed systems · CPC title

• A61P33/02

  Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis · CPC title