Back to results
US 4,036,979 AGranted
Compositions containing 4,5,6,7-tetrahydrobenz[b]thien-4-yl-ureas or derivatives and methods of enhancing growth rate
AssigneeAmerican Cyanamid Company
InventorGoro Asato
Life of this patent
Estimating the term…
Abstract
This disclosure describes a novel method for improving feed efficiency and accelerating the growth rate of veterinary homothermic animals by administering to said animals a growth-promoting amount of a cycloalkano[b]thien-4-ylurea or thiourea.
Claims76
A method for improving the feed efficiency and enhancing the growth rate of veterinary homothermic animals which comprises administering to said animals an effective amount of a compound selected from the group consisting of those of the formulae:
- ##STR147## wherein X is oxygen or sulfur;
- n is the integer 1 or 2;
- Y is a divalent radical selected from the group consisting of those of the formulae:
- ##STR148## R.sub.1 is hydrogen or alkyl C.sub.1--C.sub.4 ;
- R.sub.3 is selected from the group consisting of hydrogen, alkyl C.sub.1 -C.sub.4, cycloalkyl C.sub.3 -C.sub.6, allyl, 2-propynyl, benzyl and .beta.-phenethyl;
- R.sub.4 is hydrogen or alkyl C.sub.1 -C.sub.4 ;
- R.sub.5 is hydrogen, chloro, bromo or iodo;
- R.sub.6 is hydrogen or alkyl C.sub.1 -C.sub.4 ;
- R.sub.2 is selected from the group consisting of the substituents listed in the following table:
- ______________________________________ hydrogen alkyl C.sub.1- C.sub.8 cycloalkyl C.sub.3- C.sub.6 allyl 2-propynyl hydroxy alkoxy C.sub.1- C.sub.6 allyloxy methoxymethyl phenoxy CH.sub.2CH(OR).sub.2 CH.sub.2CF.sub.3 CH.sub.2CN NHCO.sub.2 R OCH.sub.2CO.sub.2 H CO.sub.2 C.sub.2 H.sub.5 ##STR149## ##STR150## ##STR151## ##STR152## ##STR153## ##STR154## ##STR155## ______________________________________
- wherein R is alkyl C.sub.1 -C.sub.4, m is 0, 1 or 2, and Q is selected from the group consisting of the substituents listed in the following table:
- ______________________________________ m = 0 m = 1 m = 2 ______________________________________ 4-nitro hydrogen hydrogen 3- or 4-methoxy 4-chloro 4-ethoxy 4-methoxy 4-chloro 4-butoxy 2,4-dimethyl 2,4-dichloro 2,5-dimethoxy ______________________________________
- and R.sub.2 and R.sub.3 taken together with the associated N(itrogen) is selected from the group consisting of morpholino, piperidino, pyrrolidino, 4-(4-methoxyphenyl)piperazino, 1,2,3,4-tetrahydroquniolino and the moiety of the formula:
- ##STR156##
11 more elements
A method for improving the feed efficiency and enhancing the growth rate of veterinary homothermic animals which comprise administering to said animals an effective amount of a compound selected from the group consisting of the dextrorotatory enantiomorph, the levorotatory enantiomorph, and the racemic mixture thereof of a compound of the formula:
- ##STR158## wherein X is oxygen or sulfur;
- n is the integer 1 or 2;
- R.sub.1 is hydrogen or alkyl C.sub.1 -C.sub.4 ;
- R.sub.3 is selected from the group consisting of hydrogen, alkyl C.sub.1 -C.sub.4, cycloalkyl C.sub.3 -C.sub.6, allyl, 2-propynyl, benzyl and .beta.-phenethyl;
- R.sub.4 is hydrogen or alkyl C.sub.1 -C.sub.4 ;
- R.sub.5 is hydrogen, chloro, bromo or iodo;
- R.sub.6 is hydrogen or alkyl C.sub.1 -C.sub.4 ;
- R.sub.2 is selected from the group consisting of the substituents listed in the following table:
- ______________________________________ hydrogen alkyl C.sub.1- C.sub.8 cycloalkyl C.sub.3- C.sub.6 allyl 2-propynyl hydroxy alkoxy C.sub.1- C.sub.6 allyloxy methoxymethyl phenoxy CH.sub.2CH(OR).sub.2 CH.sub.2CF.sub.3 CH.sub.2CN NHCO.sub.2 R OCH.sub.2CO.sub.2 H CO.sub.2 C.sub.2 H.sub.5 ##STR159## ##STR160## ##STR161## ##STR162## ##STR163## ##STR164## ##STR165## ______________________________________
- wherein R is alkyl C.sub.1 -C.sub.4, m is 0, 1 or 2, and Q is selected from the group consisting of the substituents listed in the following table:
- ______________________________________ m = 0 m = 1 m = 2 ______________________________________ 4-nitro hydrogen hydrogen 3- or 4-methoxy 4-chloro 4-ethoxy 4-methoxy 4-chloro 4-butoxy 2,4-dimethyl 2,4-dichloro 2,5-dimethoxy ______________________________________
- and R.sub.2 and R.sub.3 taken together with the associated N(itrogen) is selected from the group consisting of morpholino, piperidino, pyrrolidino, 4-(4-methoxyphenyl)piperazino, 1,2,3,4-tetrahydroquinolino and the moiety of the formula:
- ##STR166##
10 more elements
A method for improving the feed efficiency and enhancing the growth rate of veterinary homothermic animals which comprises administering to said animals an effective amount of a compound selected from the group consisting of the dextrorotatory enantiomorph, the levorotatory enantiomorph, and the racemic mixture thereof of a compound of the formula:
- ##STR167## wherein X is oxygen or sulfur;
- n is the integer 1 or 2;
- R.sub.1 is hydrogen or alkyl C.sub.1 -C.sub.4 ;
- R.sub.3 is selected from the group consisting of hydrogen, alkyl C.sub.1 -C.sub.4, cycloalkyl C.sub.3 -C.sub.6, allyl, 2-propynyl, benzyl and .beta.-phenethyl;
- R.sub.4 is hydrogen or alkyl C.sub.1 -C.sub.4 ;
- R.sub.5 is hydrogen, chloro, bromo or iodo;
- R.sub.6 is hydrogen or alkyl C.sub.1 -C.sub.4 ;
- R.sub.2 is selected from the group consisting of the substituents listed in the following table:
- ______________________________________ hydrogen alkyl C.sub.1C.sub.8 cycloalkyl C.sub.3C.sub.6 allyl 2-propynyl hydroxy alkoxy C.sub.1C.sub.6 allyloxy methoxymethyl phenoxy CH.sub.2CH(OR).sub.2 CH.sub.2CF.sub.3 CH.sub.2CN NHCO.sub.2 R OCH.sub.2CO.sub.2 H CO.sub.2 C.sub.2 H.sub.5 ##STR168## ##STR169## ##STR170## ##STR171## ##STR172## ##STR173## ##STR174## ______________________________________
- wherein R is alkyl C.sub.1 -C.sub.4, m is 0, 1 or 2, and Q is selected from the group consisting of the substituents listed in the following table:
- ______________________________________ m = 0 m = 1 m = 2 ______________________________________ 4-nitro hydrogen hydrogen 3- or 4-methoxy 4-chloro 4-ethoxy 4-methoxy 4-chloro 4-butoxy 2,4-dimethyl 2,4-dichloro 2,5-dimethoxy ______________________________________
- and R.sub.2 and R.sub.3 taken together with the associated N(itrogen) is selected from the group consisting of morpholino, piperidino, pyrrolidino, 4-(4-methoxyphenyl)piperazino, 1,2,3,4-tetrahydroquinolino and the moiety of the formula:
- ##STR175##
10 more elements
A method for improving the feed efficiency and enhancing the growth rate of veterinary homothermic animals which comprises administering to said animals an effective amount of a compound selected from the group consisting of the cis-dextrorotatory enantiomorph, the cis-levorotatory enantiomorph, the racemic mixture of the cis-enantiomorphs, the trans-dextrorotatory enantiomorph, the trans-levorotatory enantiomorph, and the racemic mixture of the trans-enantiomorphs of a compound of the formula:
- ##STR176## wherein X is oxygen or sulfur;
- n is the integer 1 or 2;
- R.sub.1 is hydrogen or alkyl C.sub.1 -C.sub.4 ;
- R.sub.3 is selected from the group consisting of hydrogen, alkyl C.sub.1 -C.sub.4, cycloalkyl C.sub.3 -C.sub.6, allyl, 2-propynyl, benzyl and .beta.-phenethyl;
- R.sub.4 is hydrogen or alkyl C.sub.1 -C.sub.4 ;
- R.sub.5 is hydrogen, chloro, bromo or iodo;
- R.sub.6 is hydrogen or alkyl C.sub.1 -C.sub.4 ;
- R.sub.2 is selected from the group consisting of the substituents listed in the following table:
- ______________________________________ hydrogen alkyl C.sub.1C.sub.8 cycloalkyl C.sub.3C.sub.6 allyl 2-propynyl hydroxy alkoxy C.sub.1C.sub.6 allyloxy methoxymethyl phenoxy CH.sub.2CH(OR).sub.2 CH.sub.2CF.sub.3 CH.sub.2CN NHCO.sub.2 R OCH.sub.2CO.sub.2 H CO.sub.2 C.sub.2 H.sub.5 ##STR177## ##STR178## ##STR179## ##STR180## ##STR181## ##STR182## ##STR183## ______________________________________
- wherein R is alkyl C.sub.1 -C.sub.4, m is 0, 1 or 2, and Q is selected from the group consisting of the substituents listed in the following table:
- ______________________________________ m = 0 m = 1 m = 2 ______________________________________ 4-nitro hydrogen hydrogen 3- or 4-methoxy 4-chloro 4-ethoxy 4-methoxy 4-chloro 4-butoxy 2,4-dimethyl 2,4-dichloro 2,5-dimethoxy ______________________________________
- and R.sub.2 and R.sub.3 taken together with the associated N(itrogen) is selected from the group consisting of morpholino, piperidino, pyrrolidino, 4-(4-methoxyphenyl)piperazino, 1,2,3,4-tetrahydroquinolino and the moiety of the formula:
- ##STR184##
10 more elements
An animal feed composition for improving feed efficiency and enhancing the growth rate of poultry, fur-bearing and farm animals comprising, a nutritionally balanced animal feed containing from 0.0001% to 0.08% by weight of a compound selected from the group consisting of those of the formulae:
- ##STR185## wherein X is oxygen or sulfur;
- n is the integer 1 or 2;
- Y is a divalent radical selected from the group consisting of those of the formulae:
- ##STR186## R.sub.1 is hydrogen or alkyl C.sub.1 -C.sub.4 ;
- R.sub.3 is selected from the group consisting of hydrogen, alkyl C.sub.1 -C.sub.4, cycloalkyl C.sub.3 -C.sub.6, allyl, 2-propynyl, benzyl and .beta.-phenethyl;
- R.sub.4 is hydrogen or alkyl C.sub.1 -C.sub.4 ;
- R.sub.5 is hydrogen, chloro, bromo or iodo;
- R.sub.6 is hydrogen or alkyl C.sub.1 -C.sub.4 ;
- R.sub.2 is selected from the group consisting of the substituents listed in the following table:
- ______________________________________ hydrogen alkyl C.sub.1C.sub.8 cycloalkyl C.sub.3C.sub.6 allyl 2-propynyl hydroxy alkoxy C.sub.1C.sub.6 allyloxy methoxymethyl phenoxy CH.sub.2CH(OR).sub.2 CH.sub.2CF.sub.3 CH.sub.2CN NHCO.sub.2 R OCH.sub.2CO.sub.2 H CO.sub.2 C.sub.2 H.sub.5 ##STR187## ##STR188## ##STR189## ##STR190## ##STR191## ##STR192## ##STR193## ______________________________________
- wherein R is alkyl C.sub.1 -C.sub.4 ;
- m is 0, 1 or 2, and Q is selected from the group consisting of the substituents listed in the following table:
- ______________________________________ m = 0 m = 1 m = 2 ______________________________________ 4-nitro hydrogen hydrogen 3- or 4-methoxy 4-chloro 4-ethoxy 4-methoxy 4-chloro 4-butoxy 2,4-dimethyl 2,4-dichloro 2,5-dimethoxy ______________________________________
- and R.sub.2 and R.sub.3 taken together with the associated N(itrogen) is selected from the group consisting of morpholino, piperidino, pyrrolidino, 4-(4-methoxyphenyl)piperazino, 1,2,3,4-tetrahydroquinolino and the moiety of the formula:
- ##STR194##
12 more elements
An animal feed premix for enhancing the growth rate of poultry, fur-bearing and farm animals comprising, from about 70% to 99% by weight of an edible carrier and from about 1% to 30% by weight of, a compound selected from the group consisting of those of the formulae:
- ##STR195## wherein X is oxygen or sulfur;
- n is the integer 1 or 2;
- Y is a divalent radical selected from the group consisting of those of the formulae:
- ##STR196## R.sub.1 is hydrogen or alkyl C.sub.1 -C.sub.4 ;
- R.sub.3 is selected from the group consisting of hydrogen, alkyl C.sub.1 -C.sub.4, cycloalkyl C.sub.3 -C.sub.6, allyl, 2-propynyl, benzyl and .beta.-phenethyl;
- R.sub.4 is hydrogen or alkyl C.sub.1 -C.sub.4 ;
- R.sub.5 is hydrogen, chloro, bromo or iodo;
- R.sub.6 is hydrogen or alkyl C.sub.1 -C.sub.4 ;
- R.sub.2 is selected from the group consisting of the substituents listed in the following table:
- ______________________________________ hydrogen alkyl C.sub.1C.sub.8 cycloalkyl C.sub.3C.sub.6 allyl 2-propynyl hydroxy alkoxy C.sub.1C.sub.6 allyloxy methoxymethyl phenoxy CH.sub.2CH(OR).sub.2 CH.sub.2CF.sub.3 CH.sub.2CN NHCO.sub.2 R OCH.sub.2CO.sub.2 H CO.sub.2 C.sub.2 H.sub.5 ##STR197## ##STR198## ##STR199## ##STR200## ##STR201## ##STR202## ##STR203## ______________________________________
- wherein R is alkyl C.sub.1 -C.sub.4, m is 0, 1 or 2, and Q is selected from the group consisting of the substituents listed in the following table:
- ______________________________________ m = 0 m = 1 m = 2 ______________________________________ 4-nitro hydrogen hydrogen 3- or 4-methoxy 4-chloro 4-ethoxy 4-methoxy 4-chloro 4-butoxy 2,4-dimethyl 2,4-dichloro 2,5-dimethoxy ______________________________________
- and R.sub.2 and R.sub.3 taken together with the associated N(itrogen) is selected from the group consisting of morpholino, piperidino, pyrrolidino, 4-(4-methoxyphenyl)piperazino, 1,2,3,4-tetrahydroquinolino and the moiety of the formula:
- ##STR204##
11 more elements
Dependencies are inferred from the claim text.