WO2015113321A1 - 二氨基胍衍生物及其在制备动物饲用生长促进剂中的应用 - Google Patents
二氨基胍衍生物及其在制备动物饲用生长促进剂中的应用 Download PDFInfo
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- WO2015113321A1 WO2015113321A1 PCT/CN2014/073702 CN2014073702W WO2015113321A1 WO 2015113321 A1 WO2015113321 A1 WO 2015113321A1 CN 2014073702 W CN2014073702 W CN 2014073702W WO 2015113321 A1 WO2015113321 A1 WO 2015113321A1
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- WIPO (PCT)
- Prior art keywords
- added
- animal feed
- organic phase
- guanidine derivative
- hours
- Prior art date
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- 241001465754 Metazoa Species 0.000 title claims abstract description 18
- 239000007952 growth promoter Substances 0.000 title claims abstract description 10
- JGGFDEJXWLAQKR-UHFFFAOYSA-N 1,2-diaminoguanidine Chemical class NNC(N)=NN JGGFDEJXWLAQKR-UHFFFAOYSA-N 0.000 title claims abstract description 7
- -1 n-octyl Chemical group 0.000 claims abstract description 9
- 241000287828 Gallus gallus Species 0.000 claims abstract description 8
- 235000013330 chicken meat Nutrition 0.000 claims abstract description 8
- 241000282887 Suidae Species 0.000 claims abstract description 7
- 241000272517 Anseriformes Species 0.000 claims abstract description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims abstract description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims description 14
- 239000000654 additive Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 238000009395 breeding Methods 0.000 claims 1
- 230000001488 breeding effect Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 11
- 238000002474 experimental method Methods 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 28
- 239000007787 solid Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000012074 organic phase Substances 0.000 description 21
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 239000003208 petroleum Substances 0.000 description 18
- 238000003756 stirring Methods 0.000 description 17
- 235000019439 ethyl acetate Nutrition 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- HAZRIBSLCUYMQP-UHFFFAOYSA-N 1,2-diaminoguanidine;hydron;chloride Chemical compound Cl.NN\C(N)=N/N HAZRIBSLCUYMQP-UHFFFAOYSA-N 0.000 description 12
- 239000012065 filter cake Substances 0.000 description 11
- 238000001228 spectrum Methods 0.000 description 11
- 238000001035 drying Methods 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 238000010828 elution Methods 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- NDMVXIYCFFFPLE-UHFFFAOYSA-N anthracene-9,10-diamine Chemical class C1=CC=C2C(N)=C(C=CC=C3)C3=C(N)C2=C1 NDMVXIYCFFFPLE-UHFFFAOYSA-N 0.000 description 5
- VKKXEIQIGGPMHT-UHFFFAOYSA-N 7h-purine-2,8-diamine Chemical class NC1=NC=C2NC(N)=NC2=N1 VKKXEIQIGGPMHT-UHFFFAOYSA-N 0.000 description 4
- 241000272525 Anas platyrhynchos Species 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- JRHHJNMASOIRDS-UHFFFAOYSA-N 4-ethoxybenzaldehyde Chemical compound CCOC1=CC=C(C=O)C=C1 JRHHJNMASOIRDS-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- FSMCOBJDZVRWIZ-UHFFFAOYSA-N 2-butoxybenzaldehyde Chemical compound CCCCOC1=CC=CC=C1C=O FSMCOBJDZVRWIZ-UHFFFAOYSA-N 0.000 description 2
- KVOWZHASDIKNFK-UHFFFAOYSA-N 4-octoxybenzaldehyde Chemical compound CCCCCCCCOC1=CC=C(C=O)C=C1 KVOWZHASDIKNFK-UHFFFAOYSA-N 0.000 description 2
- ZVTWZSXLLMNMQC-UHFFFAOYSA-N 4-phenylmethoxybenzaldehyde Chemical compound C1=CC(C=O)=CC=C1OCC1=CC=CC=C1 ZVTWZSXLLMNMQC-UHFFFAOYSA-N 0.000 description 2
- FGXZWMCBNMMYPL-UHFFFAOYSA-N 4-propoxybenzaldehyde Chemical compound CCCOC1=CC=C(C=O)C=C1 FGXZWMCBNMMYPL-UHFFFAOYSA-N 0.000 description 2
- 241000193468 Clostridium perfringens Species 0.000 description 2
- 241001478212 Riemerella anatipestifer Species 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
- 239000012043 crude product Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 244000144972 livestock Species 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 235000013372 meat Nutrition 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 235000019786 weight gain Nutrition 0.000 description 2
- 230000004584 weight gain Effects 0.000 description 2
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- UPSXAPQYNGXVBF-UHFFFAOYSA-N 2-bromobutane Chemical compound CCC(C)Br UPSXAPQYNGXVBF-UHFFFAOYSA-N 0.000 description 1
- NHIGQSREBZKSAJ-UHFFFAOYSA-N 2-butan-2-yloxybenzaldehyde Chemical compound CCC(C)OC1=CC=CC=C1C=O NHIGQSREBZKSAJ-UHFFFAOYSA-N 0.000 description 1
- QFTDHKYNVLTLPG-UHFFFAOYSA-N 2-cyclopentyloxybenzaldehyde Chemical compound O=CC1=CC=CC=C1OC1CCCC1 QFTDHKYNVLTLPG-UHFFFAOYSA-N 0.000 description 1
- KPLIYWNHNIPFQR-UHFFFAOYSA-N 2-pentoxybenzaldehyde Chemical compound CCCCCOC1=CC=CC=C1C=O KPLIYWNHNIPFQR-UHFFFAOYSA-N 0.000 description 1
- ZZJVNPRHHLLANO-UHFFFAOYSA-N 2-propan-2-yloxybenzaldehyde Chemical compound CC(C)OC1=CC=CC=C1C=O ZZJVNPRHHLLANO-UHFFFAOYSA-N 0.000 description 1
- VTOQFOCYBTVOJZ-UHFFFAOYSA-N 3-bromopentane Chemical compound CCC(Br)CC VTOQFOCYBTVOJZ-UHFFFAOYSA-N 0.000 description 1
- AMTVZBSJJCTNNT-UHFFFAOYSA-N 3-pentoxybenzaldehyde Chemical compound CCCCCOC1=CC=CC(C=O)=C1 AMTVZBSJJCTNNT-UHFFFAOYSA-N 0.000 description 1
- XHWMNHADTZZHGI-UHFFFAOYSA-N 4-butoxybenzaldehyde Chemical compound CCCCOC1=CC=C(C=O)C=C1 XHWMNHADTZZHGI-UHFFFAOYSA-N 0.000 description 1
- WQIOJZLYELVSQQ-UHFFFAOYSA-N 4-pentan-3-yloxybenzaldehyde Chemical compound CCC(CC)OC1=CC=C(C=O)C=C1 WQIOJZLYELVSQQ-UHFFFAOYSA-N 0.000 description 1
- YAPVGSXODFOBBR-UHFFFAOYSA-N 4-pentoxybenzaldehyde Chemical compound CCCCCOC1=CC=C(C=O)C=C1 YAPVGSXODFOBBR-UHFFFAOYSA-N 0.000 description 1
- WDANSDASCKBVKH-UHFFFAOYSA-N 4-propan-2-yloxybenzaldehyde Chemical compound CC(C)OC1=CC=C(C=O)C=C1 WDANSDASCKBVKH-UHFFFAOYSA-N 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- OUUQMGXRAFUTOK-RNIAWFEPSA-N CC(C)Oc1ccc(/C=N/NC(N/N=C/c(cc2)ccc2OC(C)C)=N)cc1 Chemical compound CC(C)Oc1ccc(/C=N/NC(N/N=C/c(cc2)ccc2OC(C)C)=N)cc1 OUUQMGXRAFUTOK-RNIAWFEPSA-N 0.000 description 1
- XERDJTXXNXEXKC-UHFFFAOYSA-N Cl.NNNN Chemical compound Cl.NNNN XERDJTXXNXEXKC-UHFFFAOYSA-N 0.000 description 1
- BPSYCHVCHAZFOY-UHFFFAOYSA-N Cl.NSN Chemical compound Cl.NSN BPSYCHVCHAZFOY-UHFFFAOYSA-N 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- 241000239226 Scorpiones Species 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000006030 antibiotic growth promoter Substances 0.000 description 1
- 238000009360 aquaculture Methods 0.000 description 1
- 244000144974 aquaculture Species 0.000 description 1
- 235000021053 average weight gain Nutrition 0.000 description 1
- 235000014590 basal diet Nutrition 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- BRTFVKHPEHKBQF-UHFFFAOYSA-N bromocyclopentane Chemical compound BrC1CCCC1 BRTFVKHPEHKBQF-UHFFFAOYSA-N 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000001937 non-anti-biotic effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
- C07C281/18—Compounds containing any of the groups, e.g. aminoguanidine the other nitrogen atom being further doubly-bound to a carbon atom, e.g. guanylhydrazones
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/111—Aromatic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/30—Feeding-stuffs specially adapted for particular animals for swines
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/70—Feeding-stuffs specially adapted for particular animals for birds
- A23K50/75—Feeding-stuffs specially adapted for particular animals for birds for poultry
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
Definitions
- Diaminoanthracene derivatives and their use in preparing animal service growth promoters are provided.
- the invention belongs to the field of livestock and animal feeding, and particularly relates to diaminopurine derivatives and their use in preparing animal service growth promoters. Background technique:
- Bioactive substances and their preparations that use a variety of chemical structures including growth promoters and various mechanisms of action are important contributions to improving the conversion rate of the feedstock and improving the productivity of the livestock industry.
- growth promoters have been or will be banned due to drug resistance transmission problems.
- a first object of the present invention is to provide a diaminopurine derivative capable of promoting growth of an animal.
- a second object of the present invention is to provide a use of a diaminoanthracene derivative represented by the formula (1) for the preparation of an animal service growth promoter.
- the animals are farm animals such as ducks, pigs, and chickens at various stages of growth.
- the diaminoanthracene derivative has an additive amount of 0.1 to 200 ppm in an animal feed, and the carrier is a full-price compounding material.
- the diaminoanthracene derivative of the present invention represented by the formula (1) is low-toxic or non-toxic to animals, and thus is suitable As a service growth promoter, it has a very good application prospect in the aquaculture industry.
- the diaminoanthracene derivative in the present invention has the specific structural formula shown below, and its code name is shown below the structural formula.
- the first step is a first step:
- Pentyloxybenzaldehyde C15.36g, 0.08mol, 2eq was dissolved in about 150ml of ethanol, then diaminoguanidine monohydrochloride ((0.7 ⁇ 1.5eq)) was added, and stirred at 10 ⁇ 70 Q C for 17 hours. Clear the clear liquid.
- the first step is a first step:
- the first step is a first step:
- the first step is a first step:
- the first step is a first step:
- the first step is a first step:
- the cyclopentyloxybenzaldehyde (15.2 g, 0.08 mol, 2 eq) was dissolved in about 150 ml of ethanol, then diaminoguanidine monohydrochloride ((0.7 ⁇ 1.5 eq)), 10 ⁇ 70 Q C stirred 17 H, the diaminoguanidine monohydrochloride gradually dissolved, a large amount of white solid precipitated, and the filter cake was washed with ethanol (50 ml * 2), 40.
- the C water bath was spun dry to give the product (1,3-bis(p-cyclopentyloxydibenzylideneamine) hydrazine hydrochloride).
- the first step is a first step:
- P-propoxybenzaldehyde (12.4 g, 0.09 mol, 2 eq) was dissolved in about 150 ml of ethanol, then diamine hydrazine monohydrochloride «0.7 to 1.5 eq)), and stirred at 10-70 ° C for 17 hours.
- the diamine hydrazine monohydrochloride gradually dissolved, a large amount of white solid precipitated, and the filter cake was washed with ethanol (50 ml * 2), and the solid was obtained by spinning a solid with a 40 Q C water bath.
- Example 12 Minimum inhibitory concentration in vitro (MICs, ppm) for Clostridium perfringens
- Table 1 Minimum inhibitory concentration of diaminopurine derivatives against Clostridium perfringens in vitro
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Birds (AREA)
- Food Science & Technology (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA2936707A CA2936707C (en) | 2014-01-29 | 2014-03-19 | Diaminoguanidine derivatives and application thereof in preparation of animal growth promoters used in feed |
US15/114,025 US9663458B2 (en) | 2014-01-29 | 2014-03-19 | Diaminoguanidine derivatives and application thereof in preparation of animal growth promoters used in feed |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410043200.5 | 2014-01-29 | ||
CN201410043200.5A CN103880712B (zh) | 2014-01-29 | 2014-01-29 | 二氨基胍衍生物及其在制备动物饲用生长促进剂中的应用 |
Publications (1)
Publication Number | Publication Date |
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WO2015113321A1 true WO2015113321A1 (zh) | 2015-08-06 |
Family
ID=50949882
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/CN2014/073702 WO2015113321A1 (zh) | 2014-01-29 | 2014-03-19 | 二氨基胍衍生物及其在制备动物饲用生长促进剂中的应用 |
Country Status (4)
Country | Link |
---|---|
US (1) | US9663458B2 (zh) |
CN (1) | CN103880712B (zh) |
CA (1) | CA2936707C (zh) |
WO (1) | WO2015113321A1 (zh) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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CN104610682B (zh) * | 2015-01-08 | 2016-10-26 | 江苏黄金龙风筒科技有限公司 | 一种复合pvc水带及其制备方法 |
CN104744312A (zh) * | 2015-02-16 | 2015-07-01 | 广州英赛特生物技术有限公司 | 异丙氧苯胍的系列盐及其在制备饲用生长促进剂中的应用 |
CN105030744B (zh) | 2015-07-09 | 2019-04-19 | 广州英赛特生物技术有限公司 | 取代苯胍衍生物作为多粘菌素类抗生素增效剂的应用 |
US11001554B2 (en) * | 2018-03-29 | 2021-05-11 | Ut-Battelle, Llc | Lipophilic guanidinium compounds for removal of oxyanions from aqueous solutions |
WO2021012138A1 (zh) * | 2019-07-22 | 2021-01-28 | 广州英赛特生物技术有限公司 | 二氨基胍衍生物及其饲用组合物在制备兽医用药物中的应用 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3901944A (en) * | 1972-05-08 | 1975-08-26 | American Cyanamid Co | 1,3-bis(substituted benzylideneamino)guanidines |
US3973039A (en) * | 1975-02-03 | 1976-08-03 | The Dow Chemical Company | [(2-Alkoxybenzylidine)amino]guanidines and their anticoccidial use |
US4015016A (en) * | 1975-02-03 | 1977-03-29 | The Dow Chemical Company | [(2-Alkoxyberzylidine)amino]quanidines and their anticoccidal use |
JPS5495638A (en) * | 1978-01-12 | 1979-07-28 | Yoshitomi Pharmaceut Ind Ltd | Antifouling agent in water |
WO2002012178A1 (en) * | 2000-08-07 | 2002-02-14 | Melacure Therapeutics Ab | Compounds acting as melanocortin receptor ligands |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1339467A (en) * | 1970-11-02 | 1973-12-05 | Merck & Co Inc | Coccidiostatic compositions |
ZA708675B (en) * | 1970-12-28 | 1971-10-27 | American Cyanamid Co | Compositions of substituted guanidines and method of use thereof |
US3795692A (en) * | 1972-03-24 | 1974-03-05 | Merck & Co Inc | Compounds and processes |
CN1037345C (zh) * | 1993-03-29 | 1998-02-11 | 山西大学 | 制备1,3-二[(4-氯苯亚甲基)氨基]胍氢溴酸盐的方法 |
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2014
- 2014-01-29 CN CN201410043200.5A patent/CN103880712B/zh active Active
- 2014-03-19 CA CA2936707A patent/CA2936707C/en active Active
- 2014-03-19 WO PCT/CN2014/073702 patent/WO2015113321A1/zh active Application Filing
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CA2936707A1 (en) | 2015-08-06 |
US9663458B2 (en) | 2017-05-30 |
CN103880712A (zh) | 2014-06-25 |
CN103880712B (zh) | 2015-12-02 |
CA2936707C (en) | 2018-07-31 |
US20160340299A1 (en) | 2016-11-24 |
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