FR2621315A1 - Derives de 2-thienylmethyl thiouree, procede pour leur preparation et aliments les contenant - Google Patents
Derives de 2-thienylmethyl thiouree, procede pour leur preparation et aliments les contenant Download PDFInfo
- Publication number
- FR2621315A1 FR2621315A1 FR8812802A FR8812802A FR2621315A1 FR 2621315 A1 FR2621315 A1 FR 2621315A1 FR 8812802 A FR8812802 A FR 8812802A FR 8812802 A FR8812802 A FR 8812802A FR 2621315 A1 FR2621315 A1 FR 2621315A1
- Authority
- FR
- France
- Prior art keywords
- general formula
- methyl
- thiourea
- thienyl
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title abstract description 31
- 235000013305 food Nutrition 0.000 title description 25
- -1 2-THIENYLMETHYL Chemical class 0.000 title description 13
- 238000002360 preparation method Methods 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 abstract description 47
- 125000000217 alkyl group Chemical group 0.000 abstract description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 14
- 241000283903 Ovis aries Species 0.000 abstract description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 10
- 235000019786 weight gain Nutrition 0.000 abstract description 8
- 230000004584 weight gain Effects 0.000 abstract description 8
- 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 7
- 241000287828 Gallus gallus Species 0.000 abstract description 6
- 235000013330 chicken meat Nutrition 0.000 abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 5
- 125000001624 naphthyl group Chemical group 0.000 abstract description 5
- 125000004076 pyridyl group Chemical group 0.000 abstract description 5
- 238000009395 breeding Methods 0.000 abstract description 4
- 230000001488 breeding effect Effects 0.000 abstract description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract description 3
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 241001465754 Metazoa Species 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 12
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical compound NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 12
- OKJOHEAQGOKDDQ-UHFFFAOYSA-N 2-(isothiocyanatomethyl)thiophene Chemical compound S=C=NCC1=CC=CS1 OKJOHEAQGOKDDQ-UHFFFAOYSA-N 0.000 description 11
- 235000013312 flour Nutrition 0.000 description 11
- 238000003756 stirring Methods 0.000 description 9
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- 239000000306 component Substances 0.000 description 8
- 235000013373 food additive Nutrition 0.000 description 8
- 239000002778 food additive Substances 0.000 description 8
- XARZSESQHPGTIA-UHFFFAOYSA-N thiophen-2-ylmethylthiourea Chemical class NC(=S)NCC1=CC=CS1 XARZSESQHPGTIA-UHFFFAOYSA-N 0.000 description 8
- 240000008042 Zea mays Species 0.000 description 7
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- 239000002480 mineral oil Substances 0.000 description 4
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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 4
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZAUXSEINZZFHJQ-UHFFFAOYSA-N 1-(2,6-dimethylphenyl)-3-(thiophen-2-ylmethyl)thiourea Chemical compound CC1=CC=CC(C)=C1NC(=S)NCC1=CC=CS1 ZAUXSEINZZFHJQ-UHFFFAOYSA-N 0.000 description 3
- MGJQDYLEYDAZMM-UHFFFAOYSA-N 1-benzyl-3-(thiophen-2-ylmethyl)thiourea Chemical compound C=1C=CC=CC=1CNC(=S)NCC1=CC=CS1 MGJQDYLEYDAZMM-UHFFFAOYSA-N 0.000 description 3
- OHIBLLMOWFJKRX-UHFFFAOYSA-N 1-cyclohexyl-3-(thiophen-2-ylmethyl)thiourea Chemical compound C1CCCCC1NC(=S)NCC1=CC=CS1 OHIBLLMOWFJKRX-UHFFFAOYSA-N 0.000 description 3
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- 235000011941 Tilia x europaea Nutrition 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 3
- 229940038472 dicalcium phosphate Drugs 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000004571 lime Substances 0.000 description 3
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- 235000010755 mineral Nutrition 0.000 description 3
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- 239000000725 suspension Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- 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 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
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- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 108010001478 Bacitracin Proteins 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- BCZXFFBUYPCTSJ-UHFFFAOYSA-L Calcium propionate Chemical compound [Ca+2].CCC([O-])=O.CCC([O-])=O BCZXFFBUYPCTSJ-UHFFFAOYSA-L 0.000 description 2
- 235000019743 Choline chloride Nutrition 0.000 description 2
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- 240000005979 Hordeum vulgare Species 0.000 description 2
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- 206010028400 Mutagenic effect Diseases 0.000 description 2
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- 150000001263 acyl chlorides Chemical class 0.000 description 2
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- CLKOFPXJLQSYAH-ABRJDSQDSA-N bacitracin A Chemical compound C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2N=CNC=2)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 CLKOFPXJLQSYAH-ABRJDSQDSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
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- GPIGWSZGKHIJPT-UHFFFAOYSA-N 1-naphthalen-1-yl-3-(thiophen-2-ylmethyl)thiourea Chemical compound C=1C=CC2=CC=CC=C2C=1NC(=S)NCC1=CC=CS1 GPIGWSZGKHIJPT-UHFFFAOYSA-N 0.000 description 1
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- XSIPFHCTNJCODE-UHFFFAOYSA-N 1-pyridin-2-yl-3-(thiophen-2-ylmethyl)thiourea Chemical compound C=1C=CC=NC=1NC(=S)NCC1=CC=CS1 XSIPFHCTNJCODE-UHFFFAOYSA-N 0.000 description 1
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- 239000004615 ingredient Substances 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
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 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
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000020712 soy bean extract 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
- TXSVRMABOIMFTH-UHFFFAOYSA-N thiophen-2-ylthiourea Chemical class NC(=S)NC1=CC=CS1 TXSVRMABOIMFTH-UHFFFAOYSA-N 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 239000002076 α-tocopherol Substances 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)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Husbandry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Zoology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Food Science & Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Fodder In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU874437A HU202516B (en) | 1987-10-02 | 1987-10-02 | Process for producing (2-thenyl)-thiourea derivatives and yield increasing agents comprising such compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2621315A1 true FR2621315A1 (fr) | 1989-04-07 |
Family
ID=10967957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8812802A Withdrawn FR2621315A1 (fr) | 1987-10-02 | 1988-09-30 | Derives de 2-thienylmethyl thiouree, procede pour leur preparation et aliments les contenant |
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 (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 |
| EP0244803A2 (en) * | 1986-05-06 | 1987-11-11 | Merrell Dow Pharmaceuticals Inc. | Novel dopamine beta hydroxylase inhibitors |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL277326A (enrdf_load_stackoverflow) * | 1963-05-31 | |||
| DE3703963A1 (de) * | 1987-02-10 | 1988-08-18 | Hoechst Ag | Pyridin-2,4- und 2,,5-dicarbonsaeure-derivate, verfahren zu ihrer herstellung, verwendung derselben, sowie arzneimittel auf basis dieser verbindungen |
-
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 CH CH3625/88A patent/CH676849A5/de not_active IP Right Cessation
- 1988-09-29 YU YU01821/88A patent/YU182188A/xx unknown
- 1988-09-30 PL PL1988274988A patent/PL151572B1/pl unknown
- 1988-09-30 JP JP63244723A patent/JPH01156975A/ja active Pending
- 1988-09-30 NL NL8802406A patent/NL8802406A/nl unknown
- 1988-09-30 DK DK549788A patent/DK549788A/da not_active Application Discontinuation
- 1988-09-30 AU AU23329/88A patent/AU607811B2/en not_active Ceased
- 1988-09-30 KR KR1019880012758A patent/KR890006612A/ko not_active Withdrawn
- 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 GB GB8823012A patent/GB2210616B/en not_active Expired - Lifetime
- 1988-09-30 ES ES8802966A patent/ES2012122A6/es not_active Expired - Lifetime
- 1988-09-30 IT IT8822147A patent/IT1226862B/it active
- 1988-09-30 RU SU884356919A patent/RU1792415C/ru active
- 1988-09-30 FR FR8812802A patent/FR2621315A1/fr not_active Withdrawn
- 1988-09-30 DD DD88320334A patent/DD282914A5/de not_active IP Right Cessation
- 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 YU00204/90A patent/YU20490A/xx unknown
- 1990-02-05 YU YU00205/90A patent/YU20590A/xx unknown
Patent Citations (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 |
| EP0244803A2 (en) * | 1986-05-06 | 1987-11-11 | Merrell Dow Pharmaceuticals Inc. | Novel dopamine beta hydroxylase inhibitors |
Non-Patent Citations (1)
| Title |
|---|
| JOURNAL OF PHARMACEUTICAL SCIENCES, vol. 75, no. 12, décembre 1986, pages 1180-1184, American Pharmaceutical Association; W.O. FOYE et al.: #"Synthesis and antimicrobial activities of N4-(2-acetoxyethoxymethyl)thiosemicarbazones and N3-(2-acetoxyethmethyl)thioureas" * |
Also Published As
| Publication number | Publication date |
|---|---|
| PL277629A1 (en) | 1989-08-21 |
| DK549788D0 (da) | 1988-09-30 |
| AU607811B2 (en) | 1991-03-14 |
| RU1792415C (ru) | 1993-01-30 |
| PL274988A1 (en) | 1989-06-12 |
| GB2210616B (en) | 1991-03-27 |
| GB8823012D0 (en) | 1988-11-09 |
| JPH01156975A (ja) | 1989-06-20 |
| KR890006612A (ko) | 1989-06-14 |
| IT8822147A0 (it) | 1988-09-30 |
| YU182188A (en) | 1990-06-30 |
| DK549788A (da) | 1989-04-03 |
| YU20590A (en) | 1990-06-30 |
| CH676849A5 (enrdf_load_stackoverflow) | 1991-03-15 |
| IT1226862B (it) | 1991-02-19 |
| DD282914A5 (de) | 1990-09-26 |
| DE3833603A1 (de) | 1989-04-13 |
| YU20490A (en) | 1990-06-30 |
| PL151836B1 (en) | 1990-10-31 |
| IL87874A0 (en) | 1989-03-31 |
| GB2210616A (en) | 1989-06-14 |
| PL277628A1 (en) | 1989-08-21 |
| ES2012122A6 (es) | 1990-03-01 |
| PL151572B1 (en) | 1990-09-28 |
| AU2332988A (en) | 1989-04-06 |
| BE1003234A4 (fr) | 1992-02-04 |
| SU1709909A3 (ru) | 1992-01-30 |
| HU202516B (en) | 1991-03-28 |
| HUT48879A (en) | 1989-07-28 |
| SU1739847A3 (ru) | 1992-06-07 |
| NL8802406A (nl) | 1989-05-01 |
| PL151837B1 (en) | 1990-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |