PH27056A - Ú5(6) (1H-azole-1-ylmethyl) benzimidazole - Google Patents
Ú5(6) (1H-azole-1-ylmethyl) benzimidazole Download PDFInfo
- Publication number
- PH27056A PH27056A PH38181A PH38181A PH27056A PH 27056 A PH27056 A PH 27056A PH 38181 A PH38181 A PH 38181A PH 38181 A PH38181 A PH 38181A PH 27056 A PH27056 A PH 27056A
- Authority
- PH
- Philippines
- Prior art keywords
- methyl
- formula
- parts
- compound
- helminths
- Prior art date
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- SVAYWWKLCLDUFZ-UHFFFAOYSA-N 2-(pyrrol-1-ylmethyl)-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1CN1C=CC=C1 SVAYWWKLCLDUFZ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 54
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 41
- 239000002253 acid Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 15
- 230000000507 anthelmentic effect Effects 0.000 claims description 14
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 12
- 241001465754 Metazoa Species 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 244000000013 helminth Species 0.000 claims 6
- 125000005059 halophenyl group Chemical group 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- -1 1H-AZOLE-1-YLMETHYL Chemical class 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 31
- 239000000243 solution Substances 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 241000282472 Canis lupus familiaris Species 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 239000003480 eluent Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- BHFLSZOGGDDWQM-UHFFFAOYSA-N 1h-benzimidazole;carbamic acid Chemical class NC(O)=O.C1=CC=C2NC=NC2=C1 BHFLSZOGGDDWQM-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 229960001701 chloroform Drugs 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
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- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical class NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 6
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- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
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- 239000007858 starting material Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/155,464 US4826862A (en) | 1988-02-12 | 1988-02-12 | Anthelminthic [(5(6) (1H-azole-1-ylmethyl)benzimidazole]carbamates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH27056A true PH27056A (en) | 1993-02-01 |
Family
ID=22555544
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH38181A PH27056A (en) | 1988-02-12 | 1989-02-10 | Ú5(6) (1H-azole-1-ylmethyl) benzimidazole |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4826862A (no) |
| EP (1) | EP0328203A3 (no) |
| JP (1) | JPH01228986A (no) |
| CN (1) | CN1022245C (no) |
| AU (1) | AU605406B2 (no) |
| DK (1) | DK64089A (no) |
| FI (1) | FI890654A (no) |
| IL (1) | IL89249A (no) |
| MA (1) | MA21493A1 (no) |
| MY (1) | MY104979A (no) |
| NO (1) | NO172438C (no) |
| NZ (1) | NZ227801A (no) |
| PH (1) | PH27056A (no) |
| PT (1) | PT89659B (no) |
| SU (1) | SU1706389A3 (no) |
| TN (1) | TNSN89015A1 (no) |
| ZA (1) | ZA891079B (no) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4943574A (en) * | 1987-06-01 | 1990-07-24 | Janssen Pharmaceutica N.V. | (1H-azol-1-ylmethyl) substituted benzotriazole derivatives and pharmaceutical compositions containing them |
| US5039677A (en) * | 1987-06-01 | 1991-08-13 | Janssen Pharmaceutica N.V. | 6-(1H-azol-1-ylmethyl)-1-(pyrimidinyloxy)-1H benzotriazoles |
| US5072453A (en) * | 1990-03-08 | 1991-12-17 | Nathaniel Widder | Body protection system |
| US5374615A (en) * | 1990-10-31 | 1994-12-20 | E. R. Squibb & Sons, Inc. | Indole- and benzimidazole-substituted imidazole and benzimidazole derivatives |
| PH31175A (en) * | 1990-10-31 | 1998-03-20 | Squibb & Sons Inc | Indole and benzimi-dazole-substituted imidazole and benzimidazole derivatives. |
| GB9115272D0 (en) * | 1991-07-15 | 1991-08-28 | Pfizer Ltd | Benzimidazole anthelmintics |
| GB9115273D0 (en) * | 1991-07-15 | 1991-08-28 | Pfizer Ltd | Benzimidazole anthelmintics |
| DE4142731A1 (de) * | 1991-12-21 | 1993-06-24 | Hoechst Ag | Biozide polymerisate und polymerisatdispersionen, verfahren zu ihrer herstellung und ihre verwendung |
| GB9205368D0 (en) * | 1992-03-12 | 1992-04-22 | Pfizer Ltd | Benzimidozole anthelmintic agents |
| US5278181A (en) * | 1992-05-12 | 1994-01-11 | Board Of Regents Acting On Behalf Of The University Of Michigan | Soluble alkyl[5-[amino (phenyl)methyl]-1H-benzimidazol-2-yl] carbamate anthelmintics |
| US20040170735A2 (en) * | 2002-04-05 | 2004-09-02 | Mcneil-Ppc, Inc. | Methods and compositions for altering the sweetness delivery profile of sucralose |
| US20040086605A1 (en) * | 2002-10-30 | 2004-05-06 | Sox Thomas E. | Composition for delivering a high intensity sweetener |
| WO2004099744A2 (en) * | 2003-05-02 | 2004-11-18 | Sensitech Inc. | Methods and apparatus for indicating temperature-related events |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3935209A (en) * | 1973-03-12 | 1976-01-27 | Syntex (U.S.A.) Inc. | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
| US3969526A (en) * | 1973-05-29 | 1976-07-13 | Smithkline Corporation | Anthelmintic 5-heterocycliothio and oxy-2-carbalkoxyaminobenzimidazles |
| US4512998A (en) * | 1980-10-20 | 1985-04-23 | Schering Corporation | Anthelmintic benzimidazole carbamates |
| NZ221729A (en) * | 1986-09-15 | 1989-07-27 | Janssen Pharmaceutica Nv | Imidazolyl methyl-substituted benzimidazole derivatives and pharmaceutical compositions |
-
1988
- 1988-02-12 US US07/155,464 patent/US4826862A/en not_active Expired - Fee Related
-
1989
- 1989-01-06 MY MYPI89000017A patent/MY104979A/en unknown
- 1989-01-30 NZ NZ227801A patent/NZ227801A/en unknown
- 1989-02-06 EP EP89200253A patent/EP0328203A3/en not_active Withdrawn
- 1989-02-06 AU AU29665/89A patent/AU605406B2/en not_active Ceased
- 1989-02-08 JP JP1027740A patent/JPH01228986A/ja active Pending
- 1989-02-09 PT PT89659A patent/PT89659B/pt active IP Right Grant
- 1989-02-10 SU SU894613388A patent/SU1706389A3/ru active
- 1989-02-10 MA MA21737A patent/MA21493A1/fr unknown
- 1989-02-10 DK DK064089A patent/DK64089A/da not_active Application Discontinuation
- 1989-02-10 FI FI890654A patent/FI890654A/fi not_active Application Discontinuation
- 1989-02-10 TN TNTNSN89015A patent/TNSN89015A1/fr unknown
- 1989-02-10 ZA ZA891079A patent/ZA891079B/xx unknown
- 1989-02-10 NO NO890579A patent/NO172438C/no unknown
- 1989-02-10 PH PH38181A patent/PH27056A/en unknown
- 1989-02-10 IL IL89249A patent/IL89249A/xx not_active IP Right Cessation
- 1989-02-11 CN CN89100752A patent/CN1022245C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| MA21493A1 (fr) | 1989-10-01 |
| IL89249A0 (en) | 1989-09-10 |
| PT89659B (pt) | 1994-02-28 |
| US4826862A (en) | 1989-05-02 |
| DK64089D0 (da) | 1989-02-10 |
| EP0328203A2 (en) | 1989-08-16 |
| CN1022245C (zh) | 1993-09-29 |
| NO890579D0 (no) | 1989-02-10 |
| JPH01228986A (ja) | 1989-09-12 |
| DK64089A (da) | 1989-08-13 |
| FI890654A0 (fi) | 1989-02-10 |
| CN1036014A (zh) | 1989-10-04 |
| EP0328203A3 (en) | 1990-03-14 |
| NO890579L (no) | 1989-08-14 |
| TNSN89015A1 (fr) | 1991-02-04 |
| NO172438B (no) | 1993-04-13 |
| NO172438C (no) | 1993-07-21 |
| SU1706389A3 (ru) | 1992-01-15 |
| ZA891079B (en) | 1990-10-31 |
| AU605406B2 (en) | 1991-01-10 |
| FI890654A (fi) | 1989-08-13 |
| IL89249A (en) | 1993-03-15 |
| AU2966589A (en) | 1989-08-17 |
| MY104979A (en) | 1994-07-30 |
| PT89659A (pt) | 1989-10-04 |
| NZ227801A (en) | 1990-10-26 |
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