DE2604110A1 - Anthelminthische zusammensetzungen auf basis von oxadiazolinonen - Google Patents
Anthelminthische zusammensetzungen auf basis von oxadiazolinonenInfo
- Publication number
- DE2604110A1 DE2604110A1 DE2604110A DE2604110A DE2604110A1 DE 2604110 A1 DE2604110 A1 DE 2604110A1 DE 2604110 A DE2604110 A DE 2604110A DE 2604110 A DE2604110 A DE 2604110A DE 2604110 A1 DE2604110 A1 DE 2604110A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- radical
- alkyl
- general formula
- alkyl part
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims description 12
- 230000000507 anthelmentic effect Effects 0.000 title claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical class O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000002994 raw material Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- -1 alkyl radical Chemical class 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 241001494479 Pecora Species 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 229910052801 chlorine Chemical group 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- NITMCMBJICXYBH-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-ethoxy-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCC)=NN1C1=CC=CC=C1Cl NITMCMBJICXYBH-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000244206 Nematoda Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000008119 colloidal silica Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- RKLIFFIQFGZOSK-UHFFFAOYSA-N ethyl n-(2-chloroanilino)carbamate Chemical compound CCOC(=O)NNC1=CC=CC=C1Cl RKLIFFIQFGZOSK-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- GHGPIPTUDQZJJS-UHFFFAOYSA-N (2-chlorophenyl)hydrazine Chemical compound NNC1=CC=CC=C1Cl GHGPIPTUDQZJJS-UHFFFAOYSA-N 0.000 description 1
- XUWFZVHZHBHDAP-UHFFFAOYSA-N 3-(2,3-dichlorophenyl)-5-methoxy-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OC)=NN1C1=CC=CC(Cl)=C1Cl XUWFZVHZHBHDAP-UHFFFAOYSA-N 0.000 description 1
- MLYKUOQLIKBKQK-UHFFFAOYSA-N 3-(2-bromophenyl)-5-ethoxy-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCC)=NN1C1=CC=CC=C1Br MLYKUOQLIKBKQK-UHFFFAOYSA-N 0.000 description 1
- HHDYKCJBBSXNOP-UHFFFAOYSA-N 3-(2-bromophenyl)-5-methoxy-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OC)=NN1C1=CC=CC=C1Br HHDYKCJBBSXNOP-UHFFFAOYSA-N 0.000 description 1
- WRLLERAOJZAAQK-UHFFFAOYSA-N 3-(2-chloro-3-methoxyphenyl)-5-ethoxy-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCC)=NN1C1=CC=CC(OC)=C1Cl WRLLERAOJZAAQK-UHFFFAOYSA-N 0.000 description 1
- LQGHPXCYCUDIHV-UHFFFAOYSA-N 3-(2-chloro-3-methoxyphenyl)-5-methoxy-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OC)=NN1C1=CC=CC(OC)=C1Cl LQGHPXCYCUDIHV-UHFFFAOYSA-N 0.000 description 1
- HQWUYCLWROXOEQ-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-methoxy-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OC)=NN1C1=CC=CC=C1Cl HQWUYCLWROXOEQ-UHFFFAOYSA-N 0.000 description 1
- MRZWJVPVDJKIBC-UHFFFAOYSA-N 5-methoxy-3-(2-methylsulfanylphenyl)-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OC)=NN1C1=CC=CC=C1SC MRZWJVPVDJKIBC-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241001465677 Ancylostomatoidea Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 241000243974 Haemonchus contortus Species 0.000 description 1
- 208000006968 Helminthiasis Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000882880 Nematodirus spathiger Species 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 241000191771 Teladorsagia circumcincta Species 0.000 description 1
- 241000122945 Trichostrongylus axei Species 0.000 description 1
- 241000243796 Trichostrongylus colubriformis Species 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- HECSHXUNOVTAIJ-UHFFFAOYSA-N hydron;(2-methoxyphenyl)hydrazine;chloride Chemical compound Cl.COC1=CC=CC=C1NN HECSHXUNOVTAIJ-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- KNOCFCBIILKQJN-UHFFFAOYSA-N methyl n-(2-methoxyanilino)carbamate Chemical compound COC(=O)NNC1=CC=CC=C1OC KNOCFCBIILKQJN-UHFFFAOYSA-N 0.000 description 1
- YARROUTVSSMVSZ-UHFFFAOYSA-N methyl n-(n-carbonochloridoyl-2-methoxyanilino)carbamate Chemical compound COC(=O)NN(C(Cl)=O)C1=CC=CC=C1OC YARROUTVSSMVSZ-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7503281A FR2299028A1 (fr) | 1975-02-03 | 1975-02-03 | Nouvea |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2604110A1 true DE2604110A1 (de) | 1976-08-05 |
Family
ID=9150654
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2604110A Pending DE2604110A1 (de) | 1975-02-03 | 1976-02-03 | Anthelminthische zusammensetzungen auf basis von oxadiazolinonen |
Country Status (7)
| Country | Link |
|---|---|
| AU (1) | AU1074176A (forum.php) |
| BE (1) | BE838195A (forum.php) |
| DE (1) | DE2604110A1 (forum.php) |
| FR (1) | FR2299028A1 (forum.php) |
| GB (1) | GB1518042A (forum.php) |
| NL (1) | NL7600777A (forum.php) |
| ZA (1) | ZA76574B (forum.php) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0419918A3 (en) * | 1989-09-23 | 1992-02-26 | Bayer Ag | Substituted 1,3,4-oxa(thia)-diazolinones, process for their preparation and their use in controlling endoparasites |
| US6369088B2 (en) | 2000-03-07 | 2002-04-09 | Aventis Pharma Deutschland Gmbh | Substituted 3-phenyl-5-alkoxy-1,3,4-oxadiazol-2-ones, their preparation and their use as pharmaceuticals |
| US6596742B1 (en) | 1999-09-04 | 2003-07-22 | Aventis Pharma Deutschland Gmbh | Substituted 3-phenyl-5-alkoxy-1,3,4-oxadiazol-2-ones, their preparation and their use in medicaments |
| US6900233B2 (en) | 2002-02-28 | 2005-05-31 | Aventis Pharma Deutschland Gmbh | Substituted 3-phenyl-5-alkoxy-3H-(1,3,4)-oxadiazol-2-ones, pharmaceutical composition and method for treating obesity thereof |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2142537A (en) * | 1983-06-03 | 1985-01-23 | Shell Int Research | <Mammalian ectoparasiticides containing n-phenyloxadiazolinones |
| DE3933092A1 (de) * | 1989-10-04 | 1991-04-11 | Bayer Ag | Substituierte 1,3,4-thiadiazolinone verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von endoparasiten |
| JP5790533B2 (ja) * | 2012-02-14 | 2015-10-07 | 住友化学株式会社 | フェニルヒドラジン−β−カルボキシレート化合物の精製方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL267311A (forum.php) * |
-
1975
- 1975-02-03 FR FR7503281A patent/FR2299028A1/fr active Granted
-
1976
- 1976-01-26 NL NL7600777A patent/NL7600777A/xx not_active Application Discontinuation
- 1976-02-02 BE BE164031A patent/BE838195A/xx unknown
- 1976-02-02 GB GB4029/76A patent/GB1518042A/en not_active Expired
- 1976-02-02 AU AU10741/76A patent/AU1074176A/en not_active Expired
- 1976-02-02 ZA ZA574A patent/ZA76574B/xx unknown
- 1976-02-03 DE DE2604110A patent/DE2604110A1/de active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0419918A3 (en) * | 1989-09-23 | 1992-02-26 | Bayer Ag | Substituted 1,3,4-oxa(thia)-diazolinones, process for their preparation and their use in controlling endoparasites |
| US6596742B1 (en) | 1999-09-04 | 2003-07-22 | Aventis Pharma Deutschland Gmbh | Substituted 3-phenyl-5-alkoxy-1,3,4-oxadiazol-2-ones, their preparation and their use in medicaments |
| US6369088B2 (en) | 2000-03-07 | 2002-04-09 | Aventis Pharma Deutschland Gmbh | Substituted 3-phenyl-5-alkoxy-1,3,4-oxadiazol-2-ones, their preparation and their use as pharmaceuticals |
| US6900233B2 (en) | 2002-02-28 | 2005-05-31 | Aventis Pharma Deutschland Gmbh | Substituted 3-phenyl-5-alkoxy-3H-(1,3,4)-oxadiazol-2-ones, pharmaceutical composition and method for treating obesity thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1518042A (en) | 1978-07-19 |
| BE838195A (fr) | 1976-08-02 |
| ZA76574B (en) | 1977-01-26 |
| FR2299028B1 (forum.php) | 1978-07-21 |
| FR2299028A1 (fr) | 1976-08-27 |
| NL7600777A (nl) | 1976-08-05 |
| AU1074176A (en) | 1977-08-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |