Substituted tetrahydroiminobenzo(b)thien-4-ylureas as novel growth promoting compounds for animals
AssigneeAmerican Cyanamid Company
InventorsGoro Asato, Terence James Bentley
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Abstract
This disclosure describes novel 4,5,6,7-tetrahydro-7-iminobenzo[b]thien-4-ylureas, methods of preparation thereof, and methods of use of said compounds for enhancing feed efficiency and for promoting the growth rate of veterinary homothermic animals.
Claims23
A racemate consisting of enantiomeric 4,5,6,7-tetrahydro-7-(substituted)benzo[b]thien-4-ylureas of the formulae:
- ##STR21## wherein R.sub.1 is selected from the group consisting of hydrogen and alkyl C.sub.1 -C.sub.4 ;
- R.sub.2 is selected from the group consisting of hydrogen, hydroxy, alkyl C.sub.1 -C.sub.4, allyl, 2-propynyl, alkoxy C.sub.1 -C.sub.4 and benzyl;
- and R.sub.3 is a moiety selected from the group consisting of those of the formulae:
- ##STR22## wherein R.sub.4 is selected from the group consisting of hydrogen, alkyl C.sub.1 -C.sub.4 and benzyl;
- R.sub.5 is alkyl C.sub.1 -C.sub.4 ;
- R.sub.6 is selected from the group consisting of hydrogen and alkyl C.sub.1 -C.sub.4 ;
- and R.sub.7 is selected from the group consisting of hydrogen, chloro, methyl and methoxy.
An enantiomer selected from the group consisting of those of the formulae:
- ##STR23## wherein R.sub.1 is selected from the group consisting of hydrogen and alkyl C.sub.1 14 C.sub.4 ;
- R.sub.2 is selected from the group consisting of hydrogen, hydroxy, alkyl C.sub.1 14 C.sub.4, allyl, 2-propynyl, alkoxy C.sub.1 -C.sub.4 and benzyl;
- and R.sub.3 is a moiety selected from the group consisting of those of the formulae:
- ##STR24## wherein R.sub.4 is selected from the group consisting of hydrogen, alkyl C.sub.1 -C.sub.4 and benzyl;
- R.sub.5 is alkyl C.sub.1 -C.sub.4 ;
- R.sub.6 is selected from the group consisting of hydrogen and alkyl C.sub.1 -C.sub.4 ;
- and R.sub.7 is selected from the group consisting of hydrogen, chloro, methyl and methoxy.
A racemate consisting of enantiomeric 4,5,6,7-tetrahydro-7-(substituted)benzo[b]thien-4-ylureas of the formulae:
- ##STR25## wherein R.sub.1 is hydrogen or methyl;
- R.sub.2 is hydrogen or alkyl C.sub.1 -C.sub.4 ;
- and R.sub.3 is a moiety selected from the group consisting of those of the formulae:
- ##STR26## wherein R.sub.4 is selected from the group consisting of hydrogen, alkyl C.sub.1 -C.sub.4 and benzyl;
- and R.sub.5 is alkyl C.sub.1 -C.sub.4.
An enantiomer selected from the group consisting of those of the formulae:
- ##STR28## wherein R.sub.1 is hydrogen or methyl;
- R.sub.2 is hydrogen or alkyl C.sub.1 -C.sub.4 ;
- and R.sub.3 is a moiety selected from the group consisting of those of the formulae:
- ##STR29## wherein R.sub.4 is selected from the group consisting of hydrogen, alkyl C.sub.1 -C.sub.4 and benzyl;
- and R.sub.5 is alkyl C.sub.1 -C.sub.4.
An enantiomer of the formula:
- ##STR31## wherein R.sub.1 is hydrogen or methyl;
- R.sub.2 is hydrogen or alkyl C.sub.1 -C.sub.4 ;
- and R.sub.3 is a moiety selected from the group consisting of those of the formulae:
- ##STR32## wherein R.sub.4 is selected from the group consisting of hydrogen, alkyl C.sub.1 -C.sub.4 and benzyl;
- and R.sub.5 is alkyl C.sub.1 -C.sub.4.
A method for improving feed efficiency and enhancing the growth rate of veterinary homothermic animals comprising administering to said animals an effective amount of a racemate consisting of enantiomers of the formulae:
- ##STR33## wherein R.sub.1 is selected from the group consisting of hydrogen and alkyl C.sub.1 -C.sub.4 ;
- R.sub.2 is selected from the group consisting of hydrogen, hydroxy, alkyl C.sub.1 -C.sub.4, allyl, 2-propynyl, alkoxy C.sub.1 -C.sub.4 and benzyl;
- and R.sub.3 is a moiety selected from the group consisting of those of the formulae:
- ##STR34## wherein R.sub.4 is selected from the group consisting of hydrogen, alkyl C.sub.1 -C.sub.4 and benzyl;
- R.sub.5 is alkyl C.sub.1 -C.sub.4 ;
- R.sub.6 is selected from the group consisting of hydrogen and alkyl C.sub.1 -C.sub.4 ;
- and R.sub.7 is selected from the group consisting of hydrogen, chloro, methyl and methoxy.
A method for improving feed efficiency and enhancing the growth rate of veterinary homothermic animals comprising administering to said animals an effective amount of an enantiomer selected from the group consisting of those of the formulae:
- ##STR35## wherein R.sub.1 is selected from the group consisting of hydrogen and alkyl C.sub.1 -C.sub.4 ;
- R.sub.2 is selected from the group consisting of hydrogen, hydroxy, alkyl C.sub.1 -C.sub.4, allyl, 2-propynyl, alkoxy C.sub.1 -C.sub.4 and benzyl;
- and R.sub.3 is a moiety selected from the group consisting of those of the formulae:
- ##STR36## wherein R.sub.4 is selected from the group consisting of hydrogen, alkyl C.sub.1 -C.sub.4 and benzyl;
- R.sub.5 is alkyl C.sub.1 -C.sub.4 ;
- R.sub.6 is selected from the group consisting of hydrogen and alkyl C.sub.1 -C.sub.4 ;
- and R.sub.7 is selected from the group consisting of hydrogen, chloro, methyl and methoxy.
An animal feed composition for improving feed efficiency and enhancing the growth rate of poultry, fur-bearing animals, and farm animals comprising a nutritionally balanced animal feed containing from 0.0001% to 0.08% by weight of a racemate consisting of enantiomers of the formulae:
- ##STR37## wherein R.sub.1 is selected from the group consisting of hydrogen and alkyl C.sub.1 -C.sub.4 ;
- R.sub.2 is selected from the group consisting of hydrogen, hydroxy, alkyl C.sub.1 -C.sub.4, allyl, 2-propynyl, alkoxy C.sub.1 -C.sub.4 and benzyl;
- and R.sub.3 is a moiety selected from the group consisting of those of the formulae:
- ##STR38## wherein R.sub.4 is selected from the group consisting of hydrogen, alkyl C.sub.1 -C.sub.4 and benzyl;
- R.sub.5 is alkyl C.sub.1 -C.sub.4 ;
- R.sub.6 is selected from the group consisting of hydrogen and alkyl C.sub.1 -C.sub.4 ;
- and R.sub.7 is selected from the group consisting of hydrogen, chloro, methyl and methoxy.
An animal feed composition for improving feed efficiency and enhancing the growth rate of poultry, fur-bearing animals, and farm animals comprising a nutritionally balanced animal feed containing from 0.0001% to 0.08% by weight of an enantiomer selected from the group consisting of those of the formulae:
- ##STR39## wherein R.sub.1 is selected from the group consisting of hydrogen and alkyl C.sub.1 -C.sub.4 ;
- R.sub.2 is selected from the group consisting of hydrogen, hydroxy, alkyl C.sub.1 -C.sub.4, allyl, 2-propynyl, alkoxy C.sub.1 -C.sub.4 and benzyl;
- and R.sub.3 is a moiety selected from the group consisting of those of the formulae:
- ##STR40## wherein R.sub.4 is selected from the group consisting of hydrogen, alkyl C.sub.1 -C.sub.4 and benzyl;
- R.sub.5 is alkyl C.sub.1 -C.sub.4 ;
- R.sub.6 is selected from the group consisting of hydrogen and alkyl C.sub.1 -C.sub.4 ;
- and R.sub.7 is selected from the group consisting of hydrogen, chloro, methyl and methoxy.
Dependencies are inferred from the claim text.