AU607811B2 - (2-thienyl-methyl)-thiourea derivatives - Google Patents
(2-thienyl-methyl)-thiourea derivatives Download PDFInfo
- Publication number
- AU607811B2 AU607811B2 AU23329/88A AU2332988A AU607811B2 AU 607811 B2 AU607811 B2 AU 607811B2 AU 23329/88 A AU23329/88 A AU 23329/88A AU 2332988 A AU2332988 A AU 2332988A AU 607811 B2 AU607811 B2 AU 607811B2
- Authority
- AU
- Australia
- Prior art keywords
- thienyl
- methyl
- general formula
- thiourea
- alkyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Ceased
Links
- XARZSESQHPGTIA-UHFFFAOYSA-N thiophen-2-ylmethylthiourea Chemical class NC(=S)NCC1=CC=CS1 XARZSESQHPGTIA-UHFFFAOYSA-N 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 29
- 241001465754 Metazoa Species 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 18
- -1 N-(p-methoxy-benzoyl)-N -(2-thienyl-methyl)- -thiourea Chemical compound 0.000 claims description 15
- OKJOHEAQGOKDDQ-UHFFFAOYSA-N 2-(isothiocyanatomethyl)thiophene Chemical compound S=C=NCC1=CC=CS1 OKJOHEAQGOKDDQ-UHFFFAOYSA-N 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 239000000654 additive Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000006564 (C4-C8) cycloalkyl group Chemical group 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
- 235000019786 weight gain Nutrition 0.000 claims description 8
- 230000004584 weight gain Effects 0.000 claims description 8
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- 239000003085 diluting agent Substances 0.000 claims description 7
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- 238000003756 stirring Methods 0.000 claims description 7
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
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- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
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- 239000004467 fishmeal Substances 0.000 claims description 5
- JWROELOQCWYKLG-UHFFFAOYSA-N 1,1-dicyclohexyl-3-(thiophen-2-ylmethyl)thiourea Chemical compound C1CCCCC1N(C1CCCCC1)C(=S)NCC1=CC=CS1 JWROELOQCWYKLG-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
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- 125000004076 pyridyl group Chemical group 0.000 claims description 4
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
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- 238000009835 boiling Methods 0.000 description 7
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- LTAWCHATRSDECJ-UHFFFAOYSA-N n-(thiophen-2-ylmethylcarbamothioyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(=S)NCC1=CC=CS1 LTAWCHATRSDECJ-UHFFFAOYSA-N 0.000 description 3
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- 125000005011 alkyl ether group Chemical group 0.000 description 1
- 229950011175 aminopicoline Drugs 0.000 description 1
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 235000021052 average daily weight gain Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229940036811 bone meal Drugs 0.000 description 1
- 239000002374 bone meal Substances 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- YYRMJZQKEFZXMX-UHFFFAOYSA-L calcium bis(dihydrogenphosphate) Chemical compound [Ca+2].OP(O)([O-])=O.OP(O)([O-])=O YYRMJZQKEFZXMX-UHFFFAOYSA-L 0.000 description 1
- 229960003563 calcium carbonate Drugs 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- AGVAZMGAQJOSFJ-WZHZPDAFSA-M cobalt(2+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+2].N#[C-].[N-]([C@@H]1[C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP(O)(=O)O[C@H]3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)\C2=C(C)/C([C@H](C\2(C)C)CCC(N)=O)=N/C/2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O AGVAZMGAQJOSFJ-WZHZPDAFSA-M 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- UVOWYVYTBHYQOR-UHFFFAOYSA-J dicalcium hydrogen phosphate phosphoric acid carbonate Chemical compound C([O-])([O-])=O.[Ca+2].P(=O)([O-])([O-])O.[Ca+2].P(O)(O)(O)=O UVOWYVYTBHYQOR-UHFFFAOYSA-J 0.000 description 1
- IDAGXRIGDWCIET-SDFKWCIISA-L disodium;(2s,3s,4s,5r)-2,3,4,5-tetrahydroxyhexanedioate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O IDAGXRIGDWCIET-SDFKWCIISA-L 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- MZSJGCPBOVTKHR-UHFFFAOYSA-N isothiocyanatocyclohexane Chemical compound S=C=NC1CCCCC1 MZSJGCPBOVTKHR-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 229910000150 monocalcium phosphate Inorganic materials 0.000 description 1
- 235000019691 monocalcium phosphate Nutrition 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- RADKZDMFGJYCBB-UHFFFAOYSA-N pyridoxal hydrochloride Natural products CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 235000019163 vitamin B12 Nutrition 0.000 description 1
- 239000011715 vitamin B12 Substances 0.000 description 1
- 235000019158 vitamin B6 Nutrition 0.000 description 1
- 239000011726 vitamin B6 Substances 0.000 description 1
- 229940011671 vitamin b6 Drugs 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 229940041603 vitamin k 3 Drugs 0.000 description 1
- 235000015099 wheat brans Nutrition 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A23K20/116—Heterocyclic compounds
- A23K20/121—Heterocyclic compounds containing oxygen or sulfur as hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Food Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Fodder In General (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU4437/87 | 1987-10-02 | ||
| HU874437A HU202516B (en) | 1987-10-02 | 1987-10-02 | Process for producing (2-thenyl)-thiourea derivatives and yield increasing agents comprising such compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2332988A AU2332988A (en) | 1989-04-06 |
| AU607811B2 true AU607811B2 (en) | 1991-03-14 |
Family
ID=10967957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU23329/88A Ceased AU607811B2 (en) | 1987-10-02 | 1988-09-30 | (2-thienyl-methyl)-thiourea derivatives |
Country Status (19)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO20093460A1 (no) * | 2009-12-02 | 2011-06-03 | Ewos Innovation As | Fôrsammensetning til fisk inneholdende en semiokjemisk maskeringsforbindelse samt anvendelse av forbindelsen. |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1020611A (en) * | 1963-05-31 | 1966-02-23 | Wellcome Found | Thenylguanidines, the preparation thereof, and pharmaceutical compositions containinghem |
| AU1145088A (en) * | 1987-02-10 | 1988-08-11 | Hoechst Aktiengesellschaft | Pyridine-2,4- and -2,5-dicarboxylic acid derivatives, processes for their preparation, the use thereof and medicaments based on these compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4267191A (en) * | 1980-05-21 | 1981-05-12 | American Cyanamid Company | Process for enhancing growth promotion in animals |
| US4313885A (en) * | 1980-05-21 | 1982-02-02 | American Cyanamid Company | Furfuryl thiourea compounds |
| JP2581556B2 (ja) * | 1986-05-06 | 1997-02-12 | メレルダウファーマスーティカルズ インコーポレーテッド | 新規なドパミンベ−タヒドロキシラ−ゼ抑制剤 |
-
1987
- 1987-10-02 HU HU874437A patent/HU202516B/hu not_active IP Right Cessation
-
1988
- 1988-09-29 IL IL87874A patent/IL87874A0/xx unknown
- 1988-09-29 YU YU01821/88A patent/YU182188A/xx unknown
- 1988-09-29 CH CH3625/88A patent/CH676849A5/de not_active IP Right Cessation
- 1988-09-30 NL NL8802406A patent/NL8802406A/nl unknown
- 1988-09-30 GB GB8823012A patent/GB2210616B/en not_active Expired - Lifetime
- 1988-09-30 KR KR1019880012758A patent/KR890006612A/ko not_active Withdrawn
- 1988-09-30 IT IT8822147A patent/IT1226862B/it active
- 1988-09-30 ES ES8802966A patent/ES2012122A6/es not_active Expired - Lifetime
- 1988-09-30 FR FR8812802A patent/FR2621315A1/fr not_active Withdrawn
- 1988-09-30 DK DK549788A patent/DK549788A/da not_active Application Discontinuation
- 1988-09-30 RU SU884356919A patent/RU1792415C/ru active
- 1988-09-30 PL PL1988274988A patent/PL151572B1/pl unknown
- 1988-09-30 JP JP63244723A patent/JPH01156975A/ja active Pending
- 1988-09-30 DD DD88320334A patent/DD282914A5/de not_active IP Right Cessation
- 1988-09-30 PL PL1988277628A patent/PL151836B1/pl unknown
- 1988-09-30 BE BE8801119A patent/BE1003234A4/fr not_active IP Right Cessation
- 1988-09-30 AU AU23329/88A patent/AU607811B2/en not_active Ceased
- 1988-09-30 PL PL1988277629A patent/PL151837B1/pl unknown
- 1988-10-03 DE DE3833603A patent/DE3833603A1/de not_active Withdrawn
-
1989
- 1989-04-18 SU SU894613899A patent/SU1739847A3/ru active
- 1989-04-18 SU SU894613916A patent/SU1709909A3/ru active
-
1990
- 1990-02-05 YU YU00205/90A patent/YU20590A/xx unknown
- 1990-02-05 YU YU00204/90A patent/YU20490A/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1020611A (en) * | 1963-05-31 | 1966-02-23 | Wellcome Found | Thenylguanidines, the preparation thereof, and pharmaceutical compositions containinghem |
| AU1145088A (en) * | 1987-02-10 | 1988-08-11 | Hoechst Aktiengesellschaft | Pyridine-2,4- and -2,5-dicarboxylic acid derivatives, processes for their preparation, the use thereof and medicaments based on these compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| NL8802406A (nl) | 1989-05-01 |
| YU20590A (en) | 1990-06-30 |
| AU2332988A (en) | 1989-04-06 |
| ES2012122A6 (es) | 1990-03-01 |
| YU20490A (en) | 1990-06-30 |
| DE3833603A1 (de) | 1989-04-13 |
| PL151837B1 (en) | 1990-10-31 |
| SU1739847A3 (ru) | 1992-06-07 |
| IT1226862B (it) | 1991-02-19 |
| PL151836B1 (en) | 1990-10-31 |
| GB8823012D0 (en) | 1988-11-09 |
| HU202516B (en) | 1991-03-28 |
| BE1003234A4 (fr) | 1992-02-04 |
| PL151572B1 (en) | 1990-09-28 |
| PL277628A1 (en) | 1989-08-21 |
| JPH01156975A (ja) | 1989-06-20 |
| IL87874A0 (en) | 1989-03-31 |
| GB2210616B (en) | 1991-03-27 |
| KR890006612A (ko) | 1989-06-14 |
| YU182188A (en) | 1990-06-30 |
| CH676849A5 (enrdf_load_stackoverflow) | 1991-03-15 |
| DK549788A (da) | 1989-04-03 |
| IT8822147A0 (it) | 1988-09-30 |
| DK549788D0 (da) | 1988-09-30 |
| PL277629A1 (en) | 1989-08-21 |
| HUT48879A (en) | 1989-07-28 |
| SU1709909A3 (ru) | 1992-01-30 |
| FR2621315A1 (fr) | 1989-04-07 |
| PL274988A1 (en) | 1989-06-12 |
| GB2210616A (en) | 1989-06-14 |
| DD282914A5 (de) | 1990-09-26 |
| RU1792415C (ru) | 1993-01-30 |
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