CA1237316A

CA1237316A - Derives de 1-(aminodihalogenophenyl)-2-aminoethane et leurs sels d'addition d'acide, utiles pour reduire l'accumulation de graisses chez les animaux a sang chaud

Derives de 1-(aminodihalogenophenyl)-2-aminoethane et leurs sels d'addition d'acide, utiles pour reduire l'accumulation de graisses chez les animaux a sang chaud

Info

Publication number: CA1237316A
Authority: CA; Canada
Prior art keywords: acid addition; compound; toxic; hydrogen; methyl
Prior art date: 1979-08-16
Legal status : Expired

Application number

CA000358312A

Other languages

English (en)

Inventor

Jane A. Kiernan

Pamela K. Baker

Current Assignee

Wyeth Holdings LLC

Original Assignee

American Cyanamid Co

Priority date

1979-08-16

Filing date

1980-08-15

Publication date

1988-05-31

1980-08-15 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1988-05-31 Application granted granted Critical

1988-05-31 Publication of CA1237316A publication Critical patent/CA1237316A/fr

Status Expired legal-status Critical Current

Links

241001465754 Metazoa Species 0.000 title claims abstract description 36
150000003839 salts Chemical class 0.000 title claims abstract description 23
239000002253 acid Substances 0.000 title claims abstract description 21
230000008021 deposition Effects 0.000 title claims abstract description 10
150000001875 compounds Chemical class 0.000 claims description 46
239000000203 mixture Substances 0.000 claims description 40
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
-1 4-amino-3,5-dichlorol- Chemical compound 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
231100000252 nontoxic Toxicity 0.000 claims description 12
230000003000 nontoxic effect Effects 0.000 claims description 12
235000012054 meals Nutrition 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
229910052736 halogen Chemical group 0.000 claims description 7
150000002367 halogens Chemical group 0.000 claims description 7
239000008188 pellet Substances 0.000 claims description 5
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
239000006052 feed supplement Substances 0.000 claims description 4
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
238000009472 formulation Methods 0.000 claims description 2
235000013372 meat Nutrition 0.000 claims description 2
238000007920 subcutaneous administration Methods 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
238000002513 implantation Methods 0.000 claims 1
238000000034 method Methods 0.000 abstract description 14
ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical class NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 abstract description 12
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244000144977 poultry Species 0.000 abstract description 9
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235000019441 ethanol Nutrition 0.000 description 20
239000000243 solution Substances 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
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238000006243 chemical reaction Methods 0.000 description 9
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QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 8
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238000002360 preparation method Methods 0.000 description 8
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230000000875 corresponding effect Effects 0.000 description 7
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239000000706 filtrate Substances 0.000 description 5
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YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 5
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239000007789 gas Substances 0.000 description 4
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OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
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NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
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125000000217 alkyl group Chemical group 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
239000012458 free base Substances 0.000 description 3
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JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
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238000002844 melting Methods 0.000 description 3
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GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
PUIRZUUEOCYTBV-UHFFFAOYSA-N 2-(3,5-dichlorophenyl)oxirane Chemical compound ClC1=CC(Cl)=CC(C2OC2)=C1 PUIRZUUEOCYTBV-UHFFFAOYSA-N 0.000 description 2
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
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AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 2
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235000011054 acetic acid Nutrition 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
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XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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JGMBBKVZFUHCJC-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)ethanone Chemical compound CC(=O)C1=CC(Cl)=CC(Cl)=C1 JGMBBKVZFUHCJC-UHFFFAOYSA-N 0.000 description 1
FGQMEAWGAUALJQ-UHFFFAOYSA-N 1-(3-phenylmethoxyphenyl)ethanone Chemical compound CC(=O)C1=CC=CC(OCC=2C=CC=CC=2)=C1 FGQMEAWGAUALJQ-UHFFFAOYSA-N 0.000 description 1
FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
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239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 description 1
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