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US 4,921,939 AGranted
Sweetening agents
AssigneeUniversite Claude Bernard Lyon 1
InventorsClaude Nofre, Jean M. Tinti, Farroudja Ouar Chatzopoulos
Life of this patent
Estimating the term…
Abstract
Substituted guanidines and ethanamidines are provided as high potency sweetening agents.
Claims37
A sweetening agent having the formula, ##STR120## including tautomeric forms thereof and physiologically acceptable salts thereof;
- wherein X.sub.3, X.sub.4 and X.sub.5 are the same or different and are selected from the group consisting of
- H,
- Br,
- CF.sub.3,
- CF.sub.2 CH.sub.3,
- CH.sub.2 CF.sub.3,
- C.sub.1 -C.sub.4 alkyl,
- CH.dbd.NOC.sub.3,
- CH.dbd.NOH,
- CHO,
- CH.sub.2 OCH.sub.3,
- CH.sub.2 OH,
- Cl,
- CN,
- COCF.sub.3,
- COC.sub.1 -C.sub.3 alkyl,
- CONH.sub.2,
- CONHC.sub.1 -C.sub.3 alkyl,
- CN(C.sub.1 -C.sub.3 alkyl).sub.2,
- COOC.sub.1 -C.sub.3 alkyl,
- COOH,
- F,
- I,
- NH.sub.2,
- NHC.sub.1 -C.sub.3 alkyl,
- N(C.sub.1 -C.sub.3 alkyl).sub.2,
- NHCHO,
- NHCOCH.sub.3,
- NHCONH.sub.2,
- NHSO.sub.2 CH.sub.3,
- NO.sub.2,
- OC.sub.1 C.sub.3 alkyl,
- OCOCH.sub.3,
- OH,
- SC.sub.1 -C.sub.3 alkyl,
- SOC.sub.1 -C.sub.3 alkyl,
- SO.sub.2 C.sub.1 -C.sub.3 alkyl,
- SO.sub.2 NH.sub.2,
- SO.sub.2 NHC.sub.1 -C.sub.3 alkyl,
- SO.sub.2 N(C.sub.1 -C.sub.3 alkyl).sub.2, and
- SO.sub.3 H;
- wherein A is selected from the group consisting of N and C;
- wherein R.sub.1 is an atom of hydrogen or R.sub.1 is a C.sub.1 to C.sub.4 saturated, unsaturated, acyclic, cyclic or mixed hydrocarbyl or modified hydrocarbyl group and wherein, in the modified hydrocarbyl group,
- 1to 2 atoms of carbon may be replaced by 1 to 2 of the same or different heteroatoms selected from the group consisting of N, O, S, Cl, Br and I,
- and 1 to 3 atoms of hydrogen may be replaced by 1 to 3 atoms of fluorine;
- wherein R.sub.2 is a C.sub.2 to C.sub.13 saturated, unsaturated, acyclic, cyclic or mixed hydrocarbyl or modified hydrocarbyl group and wherein, in the modified hydrocarbyl group,
- 1to 4 atoms of carbon may be replaced by 1 to 4 of the same or different heteroatoms selected from the group consisting of N, O, S, Cl, Br and I,
- and 1 to 5 atoms of hydrogen may be replaced by 1 to 5 atoms of fluorine;
- wherein R.sub.1 and R.sub.2 are different unless fused as a single moiety;
- wherein R.sub.3 is selected from the group consisting of H and C.sub.1 -C.sub.3 alkyl;
- and
- wherein R.sub.4 is selected from the group consisting of H and CH.sub.3 ;
- with the proviso that, when X.sub.3, X.sub.5, R.sub.3 and R.sub.4 are atoms of hydrogen,
- and when X.sub.4 is CN or NO.sub.2, that R.sub.1 and R.sub.2 are not CN or OCH.sub.3 ;
- and when X.sub.4 is H, Cl, CN, COCH.sub.3, F or NO.sub.2, that R.sub.1 is not NO.sub.2, and that R.sub.2 is not NO.sub.2 or SO.sub.2 R,
- R being an alkyl, cycloalkyl, or aryl group having up to 10 atoms of carbon, or such a group wherein 1 or 2 carbon atoms are substituted by 1 or 2 atoms of sulfur or oxygen.
53 more elements
A sweetening agent having the formula, ##STR122## including tautomeric forms thereof and physiologically acceptable salts thereof;
- wherein X.sub.3, X.sub.4 and X.sub.5 are the same or different and are selected from the group consisting of
- H,
- Br,
- CF.sub.3,
- CF.sub.2 CF.sub.3,
- CH.sub.2 CF.sub.3,
- C.sub.1 -C.sub.4 alkyl
- CH=NOCH.sub.3,
- CH=NOH,
- CHO,
- CH.sub.2 OCH.sub.3,
- CH.sub.2 OH,
- Cl,
- CN,
- COCF.sub.3,
- COC.sub.1 -C.sub.3 alkyl,
- CONH.sub.2,
- CONHC.sub.1 -C.sub.3 alkyl,
- CON(C.sub.1 -C.sub.3 alkyl).sub.2,
- COOC.sub.1 -C.sub.3 alkyl,
- COOH,
- F,
- I,
- NH.sub.2,
- NHC.sub.1 -C.sub.3 alkyl,
- N(C.sub.1 -C.sub.3 alkyl).sub.2,
- NHCHO,
- NHCOCH.sub.3,
- NHCONH.sub.2,
- NHSO.sub.2 CH.sub.3,
- NO.sub.2,
- OC.sub.1 -C.sub.3 alkyl,
- OCOCH.sub.3,
- OH,
- SC.sub.1 -C.sub.3 alkyl,
- SOC.sub.1 -C.sub.3 alkyl,
- SO.sub.2 C.sub.1 -C.sub.3 alkyl,
- SO.sub.2 NH.sub.2,
- SO.sub.2 NHC.sub.1 -C.sub.3 alkyl,
- SO.sub.2 N(C.sub.1 -C.sub.3 alkyl).sub.2, and
- SO.sub.3 H;
- wherein A is selected from the group consisting of N and C;
- wherein R.sub.1 is an atom of hydrogen or R.sub.1 is a C.sub.1 to C.sub.4 saturated, unsaturated, acyclic, cyclic or mixed hydrocarbyl or modified hydrocarbyl group and wherein, in the modified hydrocarbyl group,
- 1to 2 atoms of carbon may be replaced by 1 to 2 of the same or different heteroatoms selected from the group consisting of N, O, S, Cl, Br and I, and 1 to 3 atoms of hydrogen may be replaced by 1 to 3 atoms of fluorine;
- wherein R.sub.2 is a C.sub.2 to C.sub.13 saturated, unsaturated, acyclic, cyclic or mixed hydrocarbyl or modified hydrocarbyl group and wherein, in the modified hydrocarbyl group,
- 1 to 4 atoms of carbon may be replaced by 1 to 4 of the same or different heteroatoms selected from the group consisting of N, O, S, Cl, Br and I,
- and 1 to 5 atoms of hydrogen may be replaced by 1 to 5 atoms of fluorine;
- wherein R.sub.1 and R.sub.2 are different unless fused as a single moiety;
- wherein R.sub.3 is selected from the group consisting of H and C.sub.1 -C.sub.3 alkyl;
- and p1 wherein R.sub.4 is selected from the group consisting of H and CH.sub.3 ;
- with the proviso that, when X.sub.3, X.sub.5, R.sub.3 and R.sub.4 are atoms of hydrogen,
- and when X.sub.4 is CN or NO.sub.2, that R.sub.1 and R.sub.2 are not CN or OCH.sub.3 ;
- and when X.sub.4 is H, CF.sub.3, CHO, Cl, CN, COCH.sub.3, F or NO.sub.2, that R.sub.1 is not NO.sub.2, SOCH.sub.3 or SOC.sub.2 H.sub.5, and that R.sub.2 is not NO.sub.2, SOR, SO.sub.2 R, SO.sub.2 NHR or SO.sub.2 N(R).sub.2,
- R being an alkyl, cycloalkyl, or aryl group having up to 10 atoms of carbon, or such a group wherein 1 or 2 carbon atoms are substituted by 1 or 2 atoms of sulfura or oxygen.
51 more elements
Dependencies are inferred from the claim text.