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Products and process

Assignee: Commercial Solvents Corp
•
Filing: 1972-10-31
•
Granted: 1975-06-03
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Expires: 1992-10-31
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Abstract

Abstract Compounds of the formula: WHEREIN T is a radical selected from the group consisting of CH CH- and -CH2CH2-; Z is >C O, >CH2, or >CHOR; R is hydrogen, alkyl, aromatic hydrocarbon radicals or acyl; X is hydrogen, -OR or -OR''; R'' is benzoxazolyl, benzothiazolyl, or phenyltetrazolyl, X'' is X or tetrahydropyranyloxy; Y is hydrogen, or hydroxyl; and unless at least one of X and X'' is tetrahydropyranyloxy, benzoxazolyloxy, benzothiazolyloxy, or phenyltetrazolyloxy, then at least one of X and X'' is hydrogen; and animal feeds containing growth promoting amounts of these compounds. The novel compounds can be prepared from zearalenone and appropriate derivatives or zearalenone by (a) etherifying at least one or both of the substituents in the 2 and 4 positions (the X substituents) of the A ring with certain heterocyclic compounds and subjecting the ether to hydrogenolysis to cleave the heterocyclic ether radical and replace at least one of these substituents with hydrogen and (b) when producing compounds having at least one hydroxyl, amino or nitro substituent in the 3 and 5 positions (the Y substituents) of the A ring, nitrating either one or both, depending upon the final compound desired, of the 3 and 5 positions of compounds produced by process (a) and converting, when desired, the nitro substituent to an amino or a hydroxyl substituent. Alternatively, compounds having at least one of a hydroxyl, amino or nitro substituent can be used as a starting material in process (a).

Inventors

  • 👤 Herbert L Wehrmeister
  • 👤 David B R Johnston
  • 👤 Thomas B Windholz

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 08:47
CPC Classifications
C; C07; C07D; C07D313/00; A; A23; A23K; A23K20/00; A23K20/10; A23K20/116; A23K20/121; A23K20/126; A23K50/00; A23K50/30

Claims Analysis

Total Claims: 50
Claim 1
Independent Claim 5 words
A COMPOUND HAVING THE FORMULA
Claim 2
Dependent Claim 5 words
A COMPOUND HAVING THE FORMULA
Claim 3
Dependent Claim 5 words
A compound having the formula:
Claim 4
Dependent Claim 5 words
A compound having the formula:
Claim 5
Dependent Claim 12 words
A compound of claim 1 wherein at least one Y is amino.
Claim 6
Dependent Claim 9 words
A compound of claim 2 wherein T is -CH2CH2-.
Claim 7
Dependent Claim 12 words
A compound of claim 1 wherein at least one Y is nitro.
Claim 8
Dependent Claim 9 words
A compound of claim 4 wherein T is -CH2CH2-.
Claim 9
Dependent Claim 31 words
A compound of claim 1 wherein R is selected from the group consisting of hydrogen, lower alkyl, lower alkanoyl radicals and alkyl benzyl radicals containing up to about 10 carbon atoms.
Claim 10
Dependent Claim 4 words
Dideoxyzearalane of the formula:
Claim 11
Dependent Claim 4 words
Dideoxyzearalane of the formula:
Claim 12
Dependent Claim 5 words
A compound having the formula:
Claim 13
Dependent Claim 5 words
A compound having the formula:
Claim 14
Dependent Claim 5 words
A compound having the formula:
Claim 15
Dependent Claim 5 words
A compound having the formula:
Claim 16
Dependent Claim 5 words
A compound having the formula:
Claim 17
Dependent Claim 5 words
A compound having the formula:
Claim 18
Dependent Claim 10 words
The compounds of claim 10 wherein Z is > CH2.
Claim 19
Dependent Claim 13 words
A compound of claim 10 wherein T is -CH2CH2- and Y is hydrogen.
Claim 20
Dependent Claim 10 words
A compound of claim 12 wherein Z is > CH2.
Claim 21
Dependent Claim 9 words
A compound of claim 13 wherein X is hydrogen.
Claim 22
Dependent Claim 9 words
A compound of claim 13 wherein X'' is hydrogen.
Claim 23
Dependent Claim 11 words
A compound of claim 13 wherein X and X'' are hydrogen.
Claim 24
Dependent Claim 11 words
A compound of claim 10 wherein Z is > C O.
Claim 25
Dependent Claim 11 words
A compound of claim 17 wherein X and X'' are hydrogen.
Claim 26
Dependent Claim 21 words
A compound of claim 18 wherein Y is the 3 position is hydroxyl and Y in the 5 position is hydrogen.
Claim 27
Dependent Claim 21 words
A compound of claim 18 wherein Y in the 3 position is hydrogen and Y in the 5 position is hydroxyl.
Claim 28
Dependent Claim 5 words
A compound having the formula:
Claim 29
Dependent Claim 5 words
A compound having the formula:
Claim 30
Dependent Claim 5 words
A compound having the formula:
Claim 31
Dependent Claim 5 words
A compound having the formula:
Claim 32
Dependent Claim 5 words
A compound having the formula:
Claim 33
Dependent Claim 5 words
A compound having the formula:
Claim 34
Dependent Claim 11 words
A compound of claim 23 wherein Z is > C O.
Claim 35
Dependent Claim 9 words
A compound of claim 24 wherein X is hydrogen.
Claim 36
Dependent Claim 9 words
A compound of claim 24 wherein X'' is hydrogen.
Claim 37
Dependent Claim 11 words
A compound of claim 24 wherein X and X'' are hydrogen.
Claim 38
Dependent Claim 9 words
A process for preparing a compound having the formula:
Claim 39
Dependent Claim 9 words
A process for preparing a compound having the formula:
Claim 40
Dependent Claim 25 words
The process of claim 28 wherein R is hydrogen and the heterocyclic etherifying agent is selected from the group consisting of 2-chlorobenzothiazole, 2-chlorobenzoxazole, and 1-phenyl-5-chlorotetrazole.
Claim 41
Dependent Claim 14 words
The process of claim 29 wherein Y is hydrogen and Z is > CH2.
Claim 42
Dependent Claim 15 words
The process of claim 29 wherein Y is hydrogen and Z is > C O.
Claim 43
Dependent Claim 23 words
The process of claim 30 wherein a heterocyclic ether group is hydrogenolyzed under hydrogenolyzing conditions including hydrogen and a Group VIII metal catalyst.
Claim 44
Dependent Claim 24 words
The process of claim 31 wherein a heterocyclic ether group is hydrogenolyzed under hydrogenolyzing conditions including hydrogeN and a Group of VIII metal catalyst.
Claim 45
Dependent Claim 41 words
The process of claim 32 wherein the hydrogenolyzing conditions include temperatures from about 50* to 100*C. and the catalyst is used in a ratio from about 0.02 to 2 grams of catalyst per gram of compound to be subjected to hydrogenolysis.
Claim 46
Dependent Claim 41 words
The process of claim 33 wherein the hydrogenolyzing conditions include temperatures from about 50* to 100*C. and the catalyst is used in a ratio from about 0.02 to 2 grams of catalyst per gram of compound to be subjected to hydrogenolysis.
Claim 47
Dependent Claim 41 words
The process of claim 34 wherein one X of the starting compound is hydroxyl and it is protected against cleavage by converting the hydroxyl group to a masking ether group and subsequently removing the masking group to regenerate the hydroxyl group.
Claim 48
Dependent Claim 41 words
The process of claim 35 wherein one X of the starting compound is hydroxyl and it is protected against cleavage by converting the hydroxyl group to a masking ether group and subsequently removing the masking group to regenerate the hydroxyl group.
Claim 49
Dependent Claim 75 words
The process of claim 34 for producing dideoxyzearalane wherein zearalane is etherified with 2-chloro-benzoxazole as the heterocyclic etherifying agent in the presence of potassium carbonate to produce a heterocyclic ether group in each of the 2 and 4 positions of the A ring and each of these heterocyclic ether groups is cleaved by hydrogenolysis under hydrogenolysis conditions wherein the Group VIII metal catalyst is palladium and pressures from about 15 to 100 p.s.i. are used.
Claim 50
Dependent Claim 13 words
The process of claim 28 wherein the heterocyclic ether compound of the formula

References Cited (Backward Citations)

US3585216A Cited
US3535343A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1978-06-02 1978-12-02 1979-06-03 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1982-06-02 1982-12-02 1983-06-03 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1986-06-02 1986-12-02 1987-06-03 $7700.00 Window Closed / Lapsed

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