NZ509352A - Substituted benzimidazoles, their use as agents for combating parasitic protozoas and preparation process thereof - Google Patents
Substituted benzimidazoles, their use as agents for combating parasitic protozoas and preparation process thereofInfo
- Publication number
- NZ509352A NZ509352A NZ509352A NZ50935299A NZ509352A NZ 509352 A NZ509352 A NZ 509352A NZ 509352 A NZ509352 A NZ 509352A NZ 50935299 A NZ50935299 A NZ 50935299A NZ 509352 A NZ509352 A NZ 509352A
- Authority
- NZ
- New Zealand
- Prior art keywords
- formula
- benzimidazoles
- alkyl
- exemplified
- substituted
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 31
- 230000003071 parasitic effect Effects 0.000 title claims abstract description 15
- 150000001556 benzimidazoles Chemical class 0.000 title description 9
- 238000000034 method Methods 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 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 9
- 150000001875 compounds Chemical class 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 47
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 206010023076 Isosporiasis Diseases 0.000 claims description 15
- 208000003495 Coccidiosis Diseases 0.000 claims description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 9
- 235000011152 sodium sulphate Nutrition 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002168 alkylating agent Substances 0.000 claims description 7
- 229940100198 alkylating agent Drugs 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
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- 229940088710 antibiotic agent Drugs 0.000 claims description 5
- 229920000570 polyether Polymers 0.000 claims description 5
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- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
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- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
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- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 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)
Applications Claiming Priority (2)
| 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 |
| PCT/EP1999/004650 WO2000004022A1 (de) | 1998-07-16 | 1999-07-05 | Substituierte benzimidazole, ihre herstellung und ihre verwendung als mittel gegen parasitäre protozoen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ509352A true NZ509352A (en) | 2003-05-30 |
Family
ID=7874277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ509352A NZ509352A (en) | 1998-07-16 | 1999-07-05 | Substituted benzimidazoles, their use as agents for combating parasitic protozoas and preparation process thereof |
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 |
|---|---|
| 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 |
| DE19831985A1 (de) | 2000-01-20 |
| 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 |
|---|---|---|---|
| RENW | Renewal (renewal fees accepted) | ||
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) | ||
| ASS | Change of ownership |
Owner name: BAYER ANIMAL HEALTH GMBH, DE Free format text: OLD OWNER(S): BAYER AKTIENGESELLSCHAFT |