DE19831985A1 - Substituierte Benzimidazole, ihre Herstellung und ihre Verwendung als Mittel gegen parasitäre Protozoen - Google Patents
Substituierte Benzimidazole, ihre Herstellung und ihre Verwendung als Mittel gegen parasitäre ProtozoenInfo
- Publication number
- DE19831985A1 DE19831985A1 DE19831985A DE19831985A DE19831985A1 DE 19831985 A1 DE19831985 A1 DE 19831985A1 DE 19831985 A DE19831985 A DE 19831985A DE 19831985 A DE19831985 A DE 19831985A DE 19831985 A1 DE19831985 A1 DE 19831985A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- alkyl
- benzimidazoles
- acid
- substituted
- 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- Withdrawn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
- 206010023076 Isosporiasis Diseases 0.000 title claims description 16
- 208000003495 Coccidiosis Diseases 0.000 title claims description 15
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title abstract 2
- 244000144977 poultry Species 0.000 title description 5
- 239000003096 antiparasitic agent Substances 0.000 title 1
- 229940125687 antiparasitic agent Drugs 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 5
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims abstract 8
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- 238000006243 chemical reaction Methods 0.000 claims description 10
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- 239000003795 chemical substances by application Substances 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
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- 239000008158 vegetable oil Substances 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound 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-YRZJJWOYSA-N 0.000 description 1
- 235000005282 vitamin D3 Nutrition 0.000 description 1
- 239000011647 vitamin D3 Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 229940021056 vitamin d3 Drugs 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- UCRLQOPRDMGYOA-DFTDUNEMSA-L zinc;(4r)-4-[[(2s)-2-[[(4r)-2-[(1s,2s)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazole-4-carbonyl]amino]-4-methylpentanoyl]amino]-5-[[(2s,3s)-1-[[(3s,6r,9s,12r,15s,18r,21s)-3-(2-amino-2-oxoethyl)-18-(3-aminopropyl)-12-benzyl-15-[(2s)-butan-2-yl]-6-(carbox Chemical compound [Zn+2].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=2NC=NC=2)C(=O)N[C@H](CC([O-])=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 UCRLQOPRDMGYOA-DFTDUNEMSA-L 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (21)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19831985A DE19831985A1 (de) | 1998-07-16 | 1998-07-16 | Substituierte Benzimidazole, ihre Herstellung und ihre Verwendung als Mittel gegen parasitäre Protozoen |
| ES99932812T ES2211119T3 (es) | 1998-07-16 | 1999-07-05 | Enzimidazoles substituidos su obtencion y su empleo como agentes contra protozoos parasitantes. |
| CN99810383A CN1117753C (zh) | 1998-07-16 | 1999-07-05 | 取代的苯并咪唑及其制备方法和用作抗寄生原生动物药的用途 |
| DE59907215T DE59907215D1 (de) | 1998-07-16 | 1999-07-05 | Substituierte benzimidazole, ihre herstellung und ihre verwendung als mittel gegen parasitäre protozoen |
| CA002337351A CA2337351A1 (en) | 1998-07-16 | 1999-07-05 | Substituted benzimidazoles, production and use thereof as agents for combating parasitic protozoas |
| AU49067/99A AU4906799A (en) | 1998-07-16 | 1999-07-05 | Substituted benzimidazoles, production and use thereof as agents for combating parasitic protozoas |
| NZ509352A NZ509352A (en) | 1998-07-16 | 1999-07-05 | Substituted benzimidazoles, their use as agents for combating parasitic protozoas and preparation process thereof |
| IDW20010111A ID26837A (id) | 1998-07-16 | 1999-07-05 | Benzimidazol tersubstitusi, pembuatan dan penggunaannya sebagai zat untuk mencegah protozoa parasit |
| DK99932812T DK1097154T3 (da) | 1998-07-16 | 1999-07-05 | Substituerede benzimidazoler, fremstilling og anvendelse deraf som midler til bekæmpelse af parasitiske protozoer |
| BR9912126-3A BR9912126A (pt) | 1998-07-16 | 1999-07-05 | Benximidazóis substituìdos, sua preparação e seu emprego como agente contra protozoários parasitários |
| PCT/EP1999/004650 WO2000004022A1 (de) | 1998-07-16 | 1999-07-05 | Substituierte benzimidazole, ihre herstellung und ihre verwendung als mittel gegen parasitäre protozoen |
| US09/743,440 US6620833B1 (en) | 1998-07-16 | 1999-07-05 | Substituted benzimidazoles, production and use thereof as agents for combating parasitic protozoas |
| JP2000560128A JP2002520414A (ja) | 1998-07-16 | 1999-07-05 | 置換ベンズイミダゾール、それの製造およびそれを寄生性原生動物防除剤として用いる使用 |
| EP99932812A EP1097154B1 (de) | 1998-07-16 | 1999-07-05 | Substituierte benzimidazole, ihre herstellung und ihre verwendung als mittel gegen parasitäre protozoen |
| KR1020007014939A KR100596667B1 (ko) | 1998-07-16 | 1999-07-05 | 치환된 벤즈이미다졸, 그의 제조방법 및 기생 원생동물구제제로서 그의 용도 |
| HU0104820A HUP0104820A3 (en) | 1998-07-16 | 1999-07-05 | Substituted benzimidazoles, production and use thereof as agents for combating parasitic protozoas |
| AT99932812T ATE251164T1 (de) | 1998-07-16 | 1999-07-05 | Substituierte benzimidazole, ihre herstellung und ihre verwendung als mittel gegen parasitäre protozoen |
| HK02102363.3A HK1040710B (zh) | 1998-07-16 | 1999-07-05 | 取代的苯並咪唑及其製備方法和用作抗寄生原生動物藥的用途 |
| TW088111400A TW584634B (en) | 1998-07-16 | 1999-07-06 | Substituted benzimidazoles, their preparation and their use as agents against parasitic protozoa |
| US10/613,818 US20040010025A1 (en) | 1998-07-16 | 2003-07-03 | Substituted benzimidazoles, their preparation and their use as agents against parasitic protozoa |
| US11/601,036 US20070066671A1 (en) | 1998-07-16 | 2006-11-17 | Substituted benzimidazoles, production and use thereof as agents for combating parasitic protozoas |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19831985A DE19831985A1 (de) | 1998-07-16 | 1998-07-16 | Substituierte Benzimidazole, ihre Herstellung und ihre Verwendung als Mittel gegen parasitäre Protozoen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19831985A1 true DE19831985A1 (de) | 2000-01-20 |
Family
ID=7874277
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19831985A Withdrawn DE19831985A1 (de) | 1998-07-16 | 1998-07-16 | Substituierte Benzimidazole, ihre Herstellung und ihre Verwendung als Mittel gegen parasitäre Protozoen |
| DE59907215T Expired - Fee Related DE59907215D1 (de) | 1998-07-16 | 1999-07-05 | Substituierte benzimidazole, ihre herstellung und ihre verwendung als mittel gegen parasitäre protozoen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59907215T Expired - Fee Related DE59907215D1 (de) | 1998-07-16 | 1999-07-05 | Substituierte benzimidazole, ihre herstellung und ihre verwendung als mittel gegen parasitäre protozoen |
Country Status (18)
| Country | Link |
|---|---|
| US (3) | US6620833B1 (enExample) |
| EP (1) | EP1097154B1 (enExample) |
| JP (1) | JP2002520414A (enExample) |
| KR (1) | KR100596667B1 (enExample) |
| CN (1) | CN1117753C (enExample) |
| AT (1) | ATE251164T1 (enExample) |
| AU (1) | AU4906799A (enExample) |
| BR (1) | BR9912126A (enExample) |
| CA (1) | CA2337351A1 (enExample) |
| DE (2) | DE19831985A1 (enExample) |
| DK (1) | DK1097154T3 (enExample) |
| ES (1) | ES2211119T3 (enExample) |
| HK (1) | HK1040710B (enExample) |
| HU (1) | HUP0104820A3 (enExample) |
| ID (1) | ID26837A (enExample) |
| NZ (1) | NZ509352A (enExample) |
| TW (1) | TW584634B (enExample) |
| WO (1) | WO2000004022A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10049468A1 (de) * | 2000-10-06 | 2002-04-11 | Bayer Ag | N-Alkoxyalkyl-substituierte Benzimidazole, ihre Herstellung und ihre Verwendung als Mittel gegen parasitäre Protozoen |
| DE102004042958A1 (de) * | 2004-09-02 | 2006-03-09 | Bayer Healthcare Ag | Neue antiparasitäre Kombination von Wirkstoffen |
| DE102005000746A1 (de) * | 2005-01-05 | 2006-07-13 | Bayer Healthcare Ag | Bekämpfung der Histomoniasis |
| DE102009038950A1 (de) | 2009-08-26 | 2011-03-03 | Bayer Animal Health Gmbh | Neue antiparasitäre Kombination von Wirkstoffen |
| WO2020050403A1 (ja) * | 2018-09-06 | 2020-03-12 | 日本水産株式会社 | サケ目魚類の筋肉の融解を防ぐ方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3271249A (en) * | 1963-06-24 | 1966-09-06 | S B Penick & Co Inc | Dihalobenzimidazoles for poultry disease treatment |
| GB1122988A (en) | 1964-10-22 | 1968-08-07 | Fisons Pest Control Ltd | Benzimidazole derivatives |
| GB1163262A (en) | 1966-01-13 | 1969-09-04 | Fisons Pest Control Ltd | Substituted Benzimidazoles and Biocidally Active Compositions |
| AU413408B2 (en) | 1966-09-19 | 1971-05-19 | 2-cyanobenzimidazoles | |
| DE2040175A1 (de) | 1970-08-13 | 1972-02-17 | Wolfgang Dr Ritter | Verfahren zur Herstellung von N-substituierten N-Chlormethylcarbamidsaeureestern |
| DE2119518A1 (de) | 1971-04-22 | 1972-10-26 | Farbenfabriken Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von N-substituiertenN-Chlormethylcarbamidsäureestern und -thiolestern |
| US3738994A (en) | 1971-08-13 | 1973-06-12 | Merck & Co Inc | 2-cyano-polyhalobenzimidazoles |
| FR2521141A1 (fr) | 1982-02-09 | 1983-08-12 | Rhone Poulenc Agrochimie | Nouveaux derives du cyano-2 benzimidazole, leur preparation et leur utilisation comme fongicides |
| FR2559150B1 (fr) | 1984-02-06 | 1986-06-27 | Rhone Poulenc Agrochimie | Nouveaux derives du cyano-2 benzimidazole, leur preparation et leur utilisation comme fongicides |
| FR2594437A1 (fr) | 1986-02-19 | 1987-08-21 | Rhone Poulenc Agrochimie | Nouveaux derives du cyano-2 benzimidazole, leur preparation, les compositions les contenant et leur utilisation comme fongicide |
| NZ221729A (en) | 1986-09-15 | 1989-07-27 | Janssen Pharmaceutica Nv | Imidazolyl methyl-substituted benzimidazole derivatives and pharmaceutical compositions |
| DE4237617A1 (de) | 1992-11-06 | 1994-05-11 | Bayer Ag | Verwendung von substituierten Benzimidazolen |
| US5331003A (en) | 1993-03-26 | 1994-07-19 | Eli Lilly And Company | Anticoccidial methods |
| DE19519821A1 (de) * | 1995-05-31 | 1996-12-05 | Bayer Ag | Mittel gegen parasitäre Protozoen |
| IT1282789B1 (it) | 1996-06-07 | 1998-03-31 | Electronic Systems Spa | Dispositivo di misurazione senza contatto di spessore per materiali non metallici in film,fogli,nastri o simili |
-
1998
- 1998-07-16 DE DE19831985A patent/DE19831985A1/de not_active Withdrawn
-
1999
- 1999-07-05 CA CA002337351A patent/CA2337351A1/en not_active Abandoned
- 1999-07-05 EP EP99932812A patent/EP1097154B1/de not_active Expired - Lifetime
- 1999-07-05 AT AT99932812T patent/ATE251164T1/de not_active IP Right Cessation
- 1999-07-05 CN CN99810383A patent/CN1117753C/zh not_active Expired - Fee Related
- 1999-07-05 ES ES99932812T patent/ES2211119T3/es not_active Expired - Lifetime
- 1999-07-05 DK DK99932812T patent/DK1097154T3/da active
- 1999-07-05 KR KR1020007014939A patent/KR100596667B1/ko not_active Expired - Fee Related
- 1999-07-05 DE DE59907215T patent/DE59907215D1/de not_active Expired - Fee Related
- 1999-07-05 US US09/743,440 patent/US6620833B1/en not_active Expired - Fee Related
- 1999-07-05 HK HK02102363.3A patent/HK1040710B/zh not_active IP Right Cessation
- 1999-07-05 NZ NZ509352A patent/NZ509352A/en unknown
- 1999-07-05 ID IDW20010111A patent/ID26837A/id unknown
- 1999-07-05 BR BR9912126-3A patent/BR9912126A/pt not_active Application Discontinuation
- 1999-07-05 WO PCT/EP1999/004650 patent/WO2000004022A1/de not_active Ceased
- 1999-07-05 AU AU49067/99A patent/AU4906799A/en not_active Abandoned
- 1999-07-05 HU HU0104820A patent/HUP0104820A3/hu unknown
- 1999-07-05 JP JP2000560128A patent/JP2002520414A/ja not_active Withdrawn
- 1999-07-06 TW TW088111400A patent/TW584634B/zh not_active IP Right Cessation
-
2003
- 2003-07-03 US US10/613,818 patent/US20040010025A1/en not_active Abandoned
-
2006
- 2006-11-17 US US11/601,036 patent/US20070066671A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| NZ509352A (en) | 2003-05-30 |
| US20070066671A1 (en) | 2007-03-22 |
| HUP0104820A2 (hu) | 2002-04-29 |
| EP1097154A1 (de) | 2001-05-09 |
| EP1097154B1 (de) | 2003-10-01 |
| DK1097154T3 (da) | 2003-12-29 |
| KR100596667B1 (ko) | 2006-07-06 |
| TW584634B (en) | 2004-04-21 |
| ATE251164T1 (de) | 2003-10-15 |
| AU4906799A (en) | 2000-02-07 |
| KR20010078750A (ko) | 2001-08-21 |
| BR9912126A (pt) | 2001-04-10 |
| US20040010025A1 (en) | 2004-01-15 |
| WO2000004022A1 (de) | 2000-01-27 |
| ID26837A (id) | 2001-02-15 |
| CN1117753C (zh) | 2003-08-13 |
| DE59907215D1 (de) | 2003-11-06 |
| HK1040710A1 (en) | 2002-06-21 |
| HUP0104820A3 (en) | 2003-12-29 |
| CA2337351A1 (en) | 2000-01-27 |
| JP2002520414A (ja) | 2002-07-09 |
| CN1315954A (zh) | 2001-10-03 |
| ES2211119T3 (es) | 2004-07-01 |
| US6620833B1 (en) | 2003-09-16 |
| HK1040710B (zh) | 2004-05-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |