CS9589A2 - Agent for animals' yield increase and method of active substances production - Google Patents

Agent for animals' yield increase and method of active substances production Download PDF

Info

Publication number: CS9589A2
Authority: CS; Czechoslovakia
Prior art keywords: formula; compounds; acid; carbon atoms; alkyl group
Prior art date: 1988-01-05

Application number

CS8995A

Other languages

Czech (cs)

English (en)

Inventor

Gerhard Dr Bonse

Werner Dr Hallenbach

Hans Dr Lindel

Friedrich Prof Dr Berschauer

Original Assignee

Bayer Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1988-01-05

Filing date

1989-01-05

Publication date

1991-08-13

1989-01-05 Application filed by Bayer Ag filed Critical Bayer Ag

1991-08-13 Publication of CS9589A2 publication Critical patent/CS9589A2/cs

Links

241001465754 Metazoa Species 0.000 title claims description 28
238000004519 manufacturing process Methods 0.000 title claims description 14
238000000034 method Methods 0.000 title description 48
239000013543 active substance Substances 0.000 title description 4
239000003795 chemical substances by application Substances 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 101
239000004480 active ingredient Substances 0.000 claims description 34
239000000203 mixture Substances 0.000 claims description 27
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
-1 halomethyl ketones Chemical class 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 24
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
150000001412 amines Chemical class 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
229940058303 antinematodal benzimidazole derivative Drugs 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
239000003674 animal food additive Substances 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
239000003651 drinking water Substances 0.000 claims description 3
235000020188 drinking water Nutrition 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
240000006394 Sorghum bicolor Species 0.000 claims 1
235000011684 Sorghum saccharatum Nutrition 0.000 claims 1
235000009430 Thespesia populnea Nutrition 0.000 claims 1
239000000654 additive Substances 0.000 claims 1
150000002460 imidazoles Chemical class 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 18
239000003085 diluting agent Substances 0.000 description 18
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238000002360 preparation method Methods 0.000 description 10
125000001424 substituent group Chemical group 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
229910052500 inorganic mineral Inorganic materials 0.000 description 8
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235000010755 mineral Nutrition 0.000 description 8
239000011707 mineral Substances 0.000 description 8
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239000012279 sodium borohydride Substances 0.000 description 8
229910000033 sodium borohydride Inorganic materials 0.000 description 8
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150000001298 alcohols Chemical class 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
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LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
150000001556 benzimidazoles Chemical class 0.000 description 5
150000008282 halocarbons Chemical class 0.000 description 5
150000002825 nitriles Chemical class 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 5
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OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
240000008042 Zea mays Species 0.000 description 4
235000002017 Zea mays subsp mays Nutrition 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
230000003698 anagen phase Effects 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
235000013312 flour Nutrition 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
235000012054 meals Nutrition 0.000 description 4
229910052987 metal hydride Inorganic materials 0.000 description 4
150000004681 metal hydrides Chemical class 0.000 description 4
150000007522 mineralic acids Chemical class 0.000 description 4
239000012071 phase Substances 0.000 description 4
235000018102 proteins Nutrition 0.000 description 4
102000004169 proteins and genes Human genes 0.000 description 4
108090000623 proteins and genes Proteins 0.000 description 4
239000000243 solution Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
150000003722 vitamin derivatives Chemical class 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
PLHBJRPIYKTQOU-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)ethanone Chemical compound CC(=O)C1=CC=C2NC=NC2=C1 PLHBJRPIYKTQOU-UHFFFAOYSA-N 0.000 description 3
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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241000282887 Suidae Species 0.000 description 3
241000209140 Triticum Species 0.000 description 3
235000021307 Triticum Nutrition 0.000 description 3
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
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150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
235000010323 ascorbic acid Nutrition 0.000 description 3
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WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
230000037396 body weight Effects 0.000 description 3
229910000019 calcium carbonate Inorganic materials 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
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TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
235000013372 meat Nutrition 0.000 description 3
235000013379 molasses Nutrition 0.000 description 3
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MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
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239000000047 product Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 3
239000011573 trace mineral Substances 0.000 description 3
235000013619 trace mineral Nutrition 0.000 description 3
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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 2
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241000287828 Gallus gallus Species 0.000 description 2
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HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 2
229930003316 Vitamin D Natural products 0.000 description 2
QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 2
229930003427 Vitamin E Natural products 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
235000006708 antioxidants Nutrition 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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150000002148 esters Chemical class 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
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WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical class CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
ISPYRSDWRDQNSW-UHFFFAOYSA-L manganese(II) sulfate monohydrate Chemical compound O.[Mn+2].[O-]S([O-])(=O)=O ISPYRSDWRDQNSW-UHFFFAOYSA-L 0.000 description 2
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238000001228 spectrum Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229960004274 stearic acid Drugs 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000003760 tallow Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
KBPHJBAIARWVSC-XQIHNALSSA-N trans-lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C KBPHJBAIARWVSC-XQIHNALSSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
235000012141 vanillin Nutrition 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000019156 vitamin B Nutrition 0.000 description 1
239000011720 vitamin B Substances 0.000 description 1
229940068088 vitamin k 1 Drugs 0.000 description 1
238000005303 weighing Methods 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
235000010930 zeaxanthin Nutrition 0.000 description 1
239000001775 zeaxanthin Substances 0.000 description 1
229940043269 zeaxanthin Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/10—Radicals substituted by halogen atoms or nitro radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/26—Oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Fodder In General (AREA)

CS8995A 1988-01-05 1989-01-05 Agent for animals' yield increase and method of active substances production CS9589A2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3800096A DE3800096A1 (de)	1988-01-05	1988-01-05	Verwendung von benzimidazolderivaten als leistungsfoerderer

Publications (1)

Publication Number	Publication Date
CS9589A2 true CS9589A2 (en)	1991-08-13

Family

ID=6344829

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS8995A CS9589A2 (en)	1988-01-05	1989-01-05	Agent for animals' yield increase and method of active substances production

Country Status (15)

Country	Link
US (1)	US4960783A (pl)
EP (1)	EP0325802A1 (pl)
JP (1)	JPH02138264A (pl)
KR (1)	KR890011858A (pl)
AU (1)	AU2752888A (pl)
BR (1)	BR8900024A (pl)
CS (1)	CS9589A2 (pl)
DE (1)	DE3800096A1 (pl)
DK (1)	DK2489A (pl)
HU (1)	HU203324B (pl)
IL (1)	IL88847A0 (pl)
NZ (1)	NZ227460A (pl)
PH (1)	PH26142A (pl)
PL (1)	PL154143B1 (pl)
ZA (1)	ZA8941B (pl)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CZ104795A3 (en)	1994-04-29	1996-02-14	Lilly Co Eli	Benzimidazole derivative, process of its preparation, its use for preparing a pharmaceutical preparation and the pharmaceutical composition containing thereof
ZA967892B (en) *	1995-09-21	1998-03-18	Lilly Co Eli	Selective β3 adrenergic agonists.
TW472068B (en)	1995-10-27	2002-01-11	Mitsui Chemicals Inc	Semi-aromatic polyamide, its manufacturing process, and composition containing the same
ATE215369T1 (de)	1996-09-05	2002-04-15	Lilly Co Eli	Carbazolanaloge als selektive beta3-adrenergische agonisten
US5808080A (en) *	1996-09-05	1998-09-15	Eli Lilly And Company	Selective β3 adrenergic agonists
CO5011072A1 (es) *	1997-12-05	2001-02-28	Lilly Co Eli	Etanolaminas pirazinil substituidas como agfonistas de los receptores
CA3130291A1 (en)	2019-03-27	2020-10-01	Anthony P. FORD	Beta adrenergic agonist and methods of using the same
EP3993878A4 (en) *	2019-07-01	2023-11-08	Curasen Therapeutics, Inc.	BETA-ADRENERGIC AGONIST AND RELATED METHODS OF USE

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR3697M (fr) *	1963-05-27	1965-11-22	Ici Ltd	Médicaments a base de nouveaux composés hétérocycliques pour le traitement des maladies des arteres coronaires.
DE2432269A1 (de) *	1974-07-05	1976-01-22	Boehringer Mannheim Gmbh	Basisch substituierte derivate des 4-hydroxybenzimidazols und verfahren zu ihrer herstellung
CH624395A5 (pl) *	1976-01-08	1981-07-31	Ciba Geigy Ag
US4204069A (en) *	1976-12-06	1980-05-20	Merck & Co., Inc.	Reductive alkylation
US4082847A (en) *	1976-12-06	1978-04-04	Merck & Co., Inc.	Substituted aminoethanols and pharmaceutical use
US4070478A (en) *	1977-02-17	1978-01-24	Merck & Co., Inc.	Benzimidazole substituted alanines
DE3428526A1 (de) *	1984-08-02	1986-02-13	Boehringer Mannheim Gmbh, 6800 Mannheim	Neue aminoalkohole, verfahren zu deren herstellung sowie diese verbindung enthaltende arzneimittel

1988
- 1988-01-05 DE DE3800096A patent/DE3800096A1/de not_active Withdrawn
- 1988-12-22 NZ NZ227460A patent/NZ227460A/en unknown
- 1988-12-23 AU AU27528/88A patent/AU2752888A/en not_active Abandoned
- 1988-12-27 JP JP63328077A patent/JPH02138264A/ja active Pending
- 1988-12-30 US US07/292,581 patent/US4960783A/en not_active Expired - Fee Related
- 1988-12-30 EP EP88121880A patent/EP0325802A1/de not_active Withdrawn
- 1988-12-30 IL IL88847A patent/IL88847A0/xx unknown
1989
- 1989-01-04 DK DK002489A patent/DK2489A/da not_active Application Discontinuation
- 1989-01-04 PL PL1989277049A patent/PL154143B1/pl unknown
- 1989-01-04 ZA ZA8941A patent/ZA8941B/xx unknown
- 1989-01-04 BR BR898900024A patent/BR8900024A/pt unknown
- 1989-01-04 HU HU8922A patent/HU203324B/hu unknown
- 1989-01-05 KR KR1019890000023A patent/KR890011858A/ko not_active Withdrawn
- 1989-01-05 CS CS8995A patent/CS9589A2/cs unknown
- 1989-01-05 PH PH38006A patent/PH26142A/en unknown

Also Published As

Publication number	Publication date
HU203324B (en)	1991-07-29
US4960783A (en)	1990-10-02
PH26142A (en)	1992-03-18
PL154143B1 (en)	1991-07-31
KR890011858A (ko)	1989-08-23
DK2489A (da)	1989-07-06
NZ227460A (en)	1990-11-27
EP0325802A1 (de)	1989-08-02
HUT49588A (en)	1989-10-30
DK2489D0 (da)	1989-01-04
DE3800096A1 (de)	1989-07-13
AU2752888A (en)	1989-07-13
BR8900024A (pt)	1989-08-15
JPH02138264A (ja)	1990-05-28
PL277049A1 (en)	1989-09-18
IL88847A0 (en)	1989-07-31
ZA8941B (en)	1989-09-27

Publication	Publication Date	Title
CS9589A2 (en)	1991-08-13	Agent for animals' yield increase and method of active substances production
US4863939A (en)	1989-09-05	Heteroarylethylamine as production promoters in livestock
US4920136A (en)	1990-04-24	Substituted pyridylethanolamine livestock production promoters
US4847291A (en)	1989-07-11	Arylethanol-hydroxylamines for promotion of livestock production
US4935409A (en)	1990-06-19	Aminophenylethylamine yield promoters
US4845262A (en)	1989-07-04	Novel arylethanolamines for promoting livestock production
US5086181A (en)	1992-02-04	4-bromo-6-chloro-5-amino-2-substituted pyridyl compounds
US5010091A (en)	1991-04-23	2,4-dihalogeno-6-pyridylethanolphenylisopropylamines for shifting the protein-fat ratio of animals in favor of protein
NO750196L (pl)	1975-07-24
US4880840A (en)	1989-11-14	Arylethanolhydroxylamines and their use for promoting yield
CS465586A2 (en)	1987-12-17	Prostredek ke zvyseni uzitkovosti zvirat a zpusob vyroby ucinnych latek
JPH01216979A (ja)	1989-08-30	生産促進剤としてのピリミジン誘導体
DE3714485A1 (de)	1988-11-17	Pyrrolophenylalkanolamine und ihre derivate, verfahren zu ihrer herstellung und ihre verwendung als leistungsfoerderer