GB1510016A - Imidazole derivatives and process for their manufacture - Google Patents
Imidazole derivatives and process for their manufactureInfo
- Publication number
- GB1510016A GB1510016A GB15012/75A GB1501275A GB1510016A GB 1510016 A GB1510016 A GB 1510016A GB 15012/75 A GB15012/75 A GB 15012/75A GB 1501275 A GB1501275 A GB 1501275A GB 1510016 A GB1510016 A GB 1510016A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- imidazole
- methoxyphenyl
- alkyl
- dichlorobenzyloxy
- 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.)
- Expired
Links
- 150000002460 imidazoles Chemical class 0.000 title abstract 2
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 16
- IRSVDHPYXFLLDS-UHFFFAOYSA-N 2,4-dichloro-1-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1Cl IRSVDHPYXFLLDS-UHFFFAOYSA-N 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 6
- 229910052736 halogen Inorganic materials 0.000 abstract 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 5
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 239000002585 base Substances 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- YCCILVSKPBXVIP-UHFFFAOYSA-N 2-(4-hydroxyphenyl)ethanol Chemical compound OCCC1=CC=C(O)C=C1 YCCILVSKPBXVIP-UHFFFAOYSA-N 0.000 abstract 2
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 abstract 2
- NPFYZDNDJHZQKY-UHFFFAOYSA-N 4-Hydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 NPFYZDNDJHZQKY-UHFFFAOYSA-N 0.000 abstract 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000001299 aldehydes Chemical class 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- -1 alkali metal salt Chemical class 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- YKUCHDXIBAQWSF-UHFFFAOYSA-N methyl 3-hydroxybenzoate Chemical compound COC(=O)C1=CC=CC(O)=C1 YKUCHDXIBAQWSF-UHFFFAOYSA-N 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- RSPXXAJHFCWURE-UHFFFAOYSA-N (2-hydroxy-5-nitrophenyl)-imidazol-1-ylmethanone Chemical compound OC1=CC=C([N+]([O-])=O)C=C1C(=O)N1C=NC=C1 RSPXXAJHFCWURE-UHFFFAOYSA-N 0.000 abstract 1
- HFAQMYBPGXYUBH-UHFFFAOYSA-N (4-aminophenyl)-imidazol-1-ylmethanone Chemical compound C1=CC(N)=CC=C1C(=O)N1C=NC=C1 HFAQMYBPGXYUBH-UHFFFAOYSA-N 0.000 abstract 1
- OMWSZDODENFLSV-UHFFFAOYSA-N (5-chloro-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 OMWSZDODENFLSV-UHFFFAOYSA-N 0.000 abstract 1
- WQXWBFZMJXEMAV-UHFFFAOYSA-N 1-(2-methoxy-5-nitrophenyl)imidazole Chemical compound COC1=CC=C([N+]([O-])=O)C=C1N1C=NC=C1 WQXWBFZMJXEMAV-UHFFFAOYSA-N 0.000 abstract 1
- UFXRSQDZZKCBBQ-UHFFFAOYSA-N 1-(2-methoxyphenyl)imidazole Chemical compound COC1=CC=CC=C1N1C=NC=C1 UFXRSQDZZKCBBQ-UHFFFAOYSA-N 0.000 abstract 1
- OUHSWHKEFMTVBR-UHFFFAOYSA-N 1-(3-chloropropyl)-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(CCCCl)C=C1 OUHSWHKEFMTVBR-UHFFFAOYSA-N 0.000 abstract 1
- SKYCJQPITLYDOT-UHFFFAOYSA-N 1-(4-chlorobutan-2-yl)-4-methoxybenzene Chemical compound COC1=CC=C(C(C)CCCl)C=C1 SKYCJQPITLYDOT-UHFFFAOYSA-N 0.000 abstract 1
- BXCBUWKTXLWPSB-UHFFFAOYSA-N 1-(chloromethyl)-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1CCl BXCBUWKTXLWPSB-UHFFFAOYSA-N 0.000 abstract 1
- GXVAHCGFGVRIHQ-UHFFFAOYSA-N 1-[(2-nitrophenyl)methyl]imidazole Chemical compound [O-][N+](=O)C1=CC=CC=C1CN1C=NC=C1 GXVAHCGFGVRIHQ-UHFFFAOYSA-N 0.000 abstract 1
- ZIHZDSIJCJVNQJ-UHFFFAOYSA-N 1-[3-(4-nitrophenyl)propyl]imidazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1CCCN1C=NC=C1 ZIHZDSIJCJVNQJ-UHFFFAOYSA-N 0.000 abstract 1
- DBHODFSFBXJZNY-UHFFFAOYSA-N 2,4-dichlorobenzyl alcohol Chemical compound OCC1=CC=C(Cl)C=C1Cl DBHODFSFBXJZNY-UHFFFAOYSA-N 0.000 abstract 1
- KSKKEMJYPOUZKJ-UHFFFAOYSA-N 2-(1h-imidazol-2-ylmethyl)aniline Chemical compound NC1=CC=CC=C1CC1=NC=CN1 KSKKEMJYPOUZKJ-UHFFFAOYSA-N 0.000 abstract 1
- DRVFYNTWCAHSSS-UHFFFAOYSA-N 2-[(2,4-dichlorophenyl)methoxy]benzaldehyde Chemical compound ClC1=CC(Cl)=CC=C1COC1=CC=CC=C1C=O DRVFYNTWCAHSSS-UHFFFAOYSA-N 0.000 abstract 1
- SSGARGHTNKIJFT-UHFFFAOYSA-N 2-imidazol-1-ylbenzenethiol Chemical compound SC1=CC=CC=C1N1C=NC=C1 SSGARGHTNKIJFT-UHFFFAOYSA-N 0.000 abstract 1
- POIGXVYPRGOWQD-UHFFFAOYSA-N 2-imidazol-1-ylphenol Chemical compound OC1=CC=CC=C1N1C=NC=C1 POIGXVYPRGOWQD-UHFFFAOYSA-N 0.000 abstract 1
- YWFIUDNCQMSKNU-UHFFFAOYSA-N 3-(4-methoxyphenyl)butan-1-ol Chemical compound COC1=CC=C(C(C)CCO)C=C1 YWFIUDNCQMSKNU-UHFFFAOYSA-N 0.000 abstract 1
- GSBDHQDPAGRRJE-UHFFFAOYSA-N 4-(1h-imidazol-2-yl)aniline Chemical compound C1=CC(N)=CC=C1C1=NC=CN1 GSBDHQDPAGRRJE-UHFFFAOYSA-N 0.000 abstract 1
- HNJCSRMLVWFRPH-UHFFFAOYSA-N 4-(3-imidazol-1-ylpropyl)aniline Chemical compound C1=CC(N)=CC=C1CCCN1C=NC=C1 HNJCSRMLVWFRPH-UHFFFAOYSA-N 0.000 abstract 1
- ZZVLDZJWCSTQEJ-UHFFFAOYSA-N 4-(4-imidazol-1-ylbutan-2-yl)phenol Chemical compound C=1C=C(O)C=CC=1C(C)CCN1C=CN=C1 ZZVLDZJWCSTQEJ-UHFFFAOYSA-N 0.000 abstract 1
- KNKRHSVKIORZQB-UHFFFAOYSA-N 4-bromo-2-(hydroxymethyl)phenol Chemical compound OCC1=CC(Br)=CC=C1O KNKRHSVKIORZQB-UHFFFAOYSA-N 0.000 abstract 1
- WQZZTPSRAJMDMD-UHFFFAOYSA-N 4-chloro-2-[hydroxy(phenyl)methyl]phenol Chemical compound C=1C(Cl)=CC=C(O)C=1C(O)C1=CC=CC=C1 WQZZTPSRAJMDMD-UHFFFAOYSA-N 0.000 abstract 1
- RYUORQLHTYZCJV-UHFFFAOYSA-N 4-chloro-2-imidazol-1-ylphenol Chemical compound OC1=CC=C(Cl)C=C1N1C=NC=C1 RYUORQLHTYZCJV-UHFFFAOYSA-N 0.000 abstract 1
- 229940073735 4-hydroxy acetophenone Drugs 0.000 abstract 1
- YTHJCZRFJGXPTL-UHFFFAOYSA-N 4-hydroxy-3-nitrobenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1[N+]([O-])=O YTHJCZRFJGXPTL-UHFFFAOYSA-N 0.000 abstract 1
- XEJRCDGGVWETQJ-UHFFFAOYSA-N 4-imidazol-1-ylbenzenethiol Chemical compound C1=CC(S)=CC=C1N1C=NC=C1 XEJRCDGGVWETQJ-UHFFFAOYSA-N 0.000 abstract 1
- 241001480043 Arthrodermataceae Species 0.000 abstract 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 abstract 1
- 241000192125 Firmicutes Species 0.000 abstract 1
- 206010017533 Fungal infection Diseases 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- 208000031888 Mycoses Diseases 0.000 abstract 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 abstract 1
- 238000000297 Sandmeyer reaction Methods 0.000 abstract 1
- GMHDRBDDYDJKIZ-UHFFFAOYSA-N [4-[(2,4-dichlorophenyl)methoxy]phenyl]-phenylmethanol Chemical compound ClC1=C(COC2=CC=C(C(C3=CC=CC=C3)O)C=C2)C=CC(=C1)Cl GMHDRBDDYDJKIZ-UHFFFAOYSA-N 0.000 abstract 1
- ONBSDZDUXYKLKN-UHFFFAOYSA-N [4-[(2,4-dichlorophenyl)methoxy]phenyl]-phenylmethanone Chemical compound ClC1=CC(Cl)=CC=C1COC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 ONBSDZDUXYKLKN-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000005660 chlorination reaction Methods 0.000 abstract 1
- 230000017858 demethylation Effects 0.000 abstract 1
- 238000010520 demethylation reaction Methods 0.000 abstract 1
- 230000037304 dermatophytes Effects 0.000 abstract 1
- 229960004698 dichlorobenzyl alcohol Drugs 0.000 abstract 1
- ZXSBDSGRQIWJPM-UHFFFAOYSA-N dimethylcarbamothioic s-acid Chemical compound CN(C)C(S)=O ZXSBDSGRQIWJPM-UHFFFAOYSA-N 0.000 abstract 1
- ATJVZXXHKSYELS-FNORWQNLSA-N ethyl (e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate Chemical compound CCOC(=O)\C=C\C1=CC=C(O)C(OC)=C1 ATJVZXXHKSYELS-FNORWQNLSA-N 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- CFNFDUJWLXMVHH-KTKRTIGZSA-N ethyl (z)-3-(4-methoxyphenyl)but-2-enoate Chemical compound CCOC(=O)\C=C(\C)C1=CC=C(OC)C=C1 CFNFDUJWLXMVHH-KTKRTIGZSA-N 0.000 abstract 1
- ORAUFGIENZKKPP-UHFFFAOYSA-N ethyl 3-(4-methoxyphenyl)butanoate Chemical compound CCOC(=O)CC(C)C1=CC=C(OC)C=C1 ORAUFGIENZKKPP-UHFFFAOYSA-N 0.000 abstract 1
- RKXKDMWTGMRMPV-UHFFFAOYSA-N ethyl 3-[2-bromo-4-[(2,4-dichlorophenyl)methoxy]-5-methoxyphenyl]propanoate Chemical compound C(C)OC(CCC1=C(C=C(C(=C1)OC)OCC1=C(C=C(C=C1)Cl)Cl)Br)=O RKXKDMWTGMRMPV-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- SIGOIUCRXKUEIG-UHFFFAOYSA-N methyl 2-dimethoxyphosphorylacetate Chemical compound COC(=O)CP(=O)(OC)OC SIGOIUCRXKUEIG-UHFFFAOYSA-N 0.000 abstract 1
- HLXHDXRVKGTGOC-UHFFFAOYSA-N methyl 3-[(2,4-dichlorophenyl)methoxy]benzoate Chemical compound COC(=O)C1=CC=CC(OCC=2C(=CC(Cl)=CC=2)Cl)=C1 HLXHDXRVKGTGOC-UHFFFAOYSA-N 0.000 abstract 1
- PHWISQNXPLXQRU-UHFFFAOYSA-N n,n-dimethylcarbamothioyl chloride Chemical compound CN(C)C(Cl)=S PHWISQNXPLXQRU-UHFFFAOYSA-N 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 abstract 1
- 150000003333 secondary alcohols Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 230000009885 systemic effect Effects 0.000 abstract 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 abstract 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 abstract 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 abstract 1
- 235000012141 vanillin Nutrition 0.000 abstract 1
Classifications
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742418502 DE2418502C3 (de) | 1974-04-11 | 1974-04-11 | Dichlorbenzyl- [2-( a -imidazolylbutyl)-phenyl] -äther und -thioäther, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| DE19752510130 DE2510130A1 (de) | 1975-03-06 | 1975-03-06 | Imidazolderivate und verfahren zu ihrer herstellung |
| DE19752510781 DE2510781A1 (de) | 1975-03-07 | 1975-03-07 | Imidazolderivate und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1510016A true GB1510016A (en) | 1978-05-10 |
Family
ID=27185894
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB15012/75A Expired GB1510016A (en) | 1974-04-11 | 1975-04-11 | Imidazole derivatives and process for their manufacture |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4006243A (en, 2012) |
| JP (1) | JPS6018654B2 (en, 2012) |
| AT (1) | AT341518B (en, 2012) |
| CA (1) | CA1051908A (en, 2012) |
| CH (1) | CH612185A5 (en, 2012) |
| CS (1) | CS194221B2 (en, 2012) |
| DD (1) | DD121515A5 (en, 2012) |
| DK (1) | DK139909C (en, 2012) |
| ES (1) | ES436546A1 (en, 2012) |
| FR (1) | FR2267101B1 (en, 2012) |
| GB (1) | GB1510016A (en, 2012) |
| HU (1) | HU172895B (en, 2012) |
| IE (1) | IE40911B1 (en, 2012) |
| IL (1) | IL47061A (en, 2012) |
| NL (1) | NL7504387A (en, 2012) |
| SE (1) | SE418498B (en, 2012) |
| YU (1) | YU89875A (en, 2012) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2126218A (en) * | 1982-08-14 | 1984-03-21 | Wellcome Found | Imidazoles |
| US4448781A (en) * | 1979-01-19 | 1984-05-15 | Pfizer Inc. | N-Benzyl-imidazoles as selective inhibitors of the thromboxane synthetase enzyme |
| EP0247725A3 (en) * | 1986-04-29 | 1990-01-17 | Pfizer Inc. | Calcium independent camp phosphodiestrerase inhibitor antidepressant |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT328587B (de) * | 1973-08-20 | 1976-03-25 | Vianova Kunstharz Ag | Verfahren zur herstellung von wasserigen uberzugsmitteln |
| US4237158A (en) * | 1975-02-05 | 1980-12-02 | Rohm And Haas Company | 1-Substituted aralkyl imidazoles and their use as fungicides |
| DE2549798C3 (de) * | 1975-11-06 | 1978-06-29 | Nordmark-Werke Gmbh, 2000 Hamburg | 1,2-Dipheny l-3-(imidazo Wl-1 )propene, Verfahren zu deren Herstellung sowie diese enthaltende Arzneimittel |
| US4118461A (en) * | 1975-12-18 | 1978-10-03 | Rohm And Haas Company | 1-Substituted aralkyl imidazoles |
| US4115578A (en) * | 1975-12-18 | 1978-09-19 | Rohm And Haas Company | 1-Substituted aralkyl imidazoles |
| DE2732750A1 (de) * | 1977-07-20 | 1979-02-08 | Merck Patent Gmbh | Basische thioaether und verfahren zu ihrer herstellung |
| US4431815A (en) * | 1977-08-26 | 1984-02-14 | Burroughs Wellcome Co. | 1-[3-(2,4-Dichlorophenyl)propyl]imidazole and salts thereof |
| US4284641A (en) * | 1977-08-26 | 1981-08-18 | Burroughs Wellcome Co. | Pharmaceutically active imidazole derivatives |
| US4396771A (en) * | 1977-10-19 | 1983-08-02 | Burroughs Wellcome Co. | Imidazole derivatives and salts thereof |
| IT1097314B (it) * | 1978-07-26 | 1985-08-31 | Recordati Chem Pharm | Derivati dell'imidazolo ad attivita' anticonvulsivante |
| JPS5951943B2 (ja) * | 1978-08-21 | 1984-12-17 | キツセイ薬品工業株式会社 | 新規なイミダゾ−ル誘導体 |
| DE2842759A1 (de) * | 1978-09-30 | 1980-04-10 | Merck Patent Gmbh | Basische aether, diese enthaltende pharmazeutische zubereitungen und verfahren zu ihrer herstellung |
| DK157860C (da) * | 1979-06-07 | 1990-07-30 | Shionogi & Co | Analogifremgangsmaade til fremstilling af benzylimidazolderivater samt farmaceutisk acceptable syreadditionssalte deraf |
| US4218461A (en) * | 1979-08-15 | 1980-08-19 | E. R. Squibb & Sons, Inc. | 2,3-Dihydro-2-[(1H-imidazol-1-yl)-methylene]-1H-inden-1-ones |
| GB2069481B (en) * | 1980-02-13 | 1983-07-27 | Farmos Oy | Substituted imidazole derivatives |
| CA1156661A (en) * | 1980-02-25 | 1983-11-08 | Hoffmann-La Roche Limited | Phenoxy-aminopropanol derivatives |
| JPS57502126A (en, 2012) * | 1980-12-05 | 1982-12-02 | ||
| IL66242A0 (en) * | 1981-07-23 | 1982-11-30 | Erba Farmitalia | N-imidazolyl derivatives of 1,2,3,4-tetrahydro-naphthalene,indan and 2-substituted-1-chroman,their preparation and pharmaceutical compositions containing them |
| JPS58150566A (ja) * | 1982-03-03 | 1983-09-07 | Yoshitomi Pharmaceut Ind Ltd | 新規イミダゾ−ル誘導体 |
| ES8503669A1 (es) * | 1982-07-05 | 1985-03-01 | Erba Farmitalia | Procedimiento para preparar derivados n-imidazolilicos de compuestos biciclicos. |
| JPS60142965A (ja) * | 1983-09-05 | 1985-07-29 | Yoshitomi Pharmaceut Ind Ltd | イミダゾ−ル誘導体の製造法 |
| EP0149976A3 (de) * | 1983-12-30 | 1986-12-10 | Ciba-Geigy Ag | Substituierte Imidazole |
| US4755526A (en) * | 1984-06-18 | 1988-07-05 | Eli Lilly And Company | Method of inhibiting aromatase |
| US4937250A (en) * | 1988-03-07 | 1990-06-26 | Ciba-Geigy Corporation | Alpha-heterocycle substituted tolunitriles |
| US4978672A (en) * | 1986-03-07 | 1990-12-18 | Ciba-Geigy Corporation | Alpha-heterocyclc substituted tolunitriles |
| US5459145A (en) * | 1988-01-19 | 1995-10-17 | Pfizer Inc. | Calcium independent camp phosphodiesterase inhibitor antidepressant |
| CA1329614C (en) * | 1987-05-02 | 1994-05-17 | Rainer Buerstinghaus | N-substituted azoles |
| US5214064A (en) * | 1987-05-02 | 1993-05-25 | Basf Aktiengesellschaft | Phenoxyphenylmethyl substituted azoles and pesticidal composition thereof |
| US5280036A (en) * | 1987-05-02 | 1994-01-18 | Basf Aktiengesellschaft | N-phenoxyphenyloxymethyl substituted azoles and method for controlling pests therewith |
| IL91542A0 (en) * | 1988-10-06 | 1990-04-29 | Erba Carlo Spa | N-imidazolyl-and n-imidazolyl-methyl derivatives of substituted bicyclic compounds,their preparation and pharmaceutical compositions containing them |
| ZA923283B (en) * | 1991-05-29 | 1993-01-27 | Akzo Nv | Phenoxyphenyl derivatives |
| US5395935A (en) * | 1992-05-08 | 1995-03-07 | Pfizer Inc. | Endo-bicyclo[2.2.1]heptan-2-ol and derived pharmaceutical agents |
| EP0757988A4 (en) * | 1994-04-27 | 2000-07-26 | Nippon Soda Co | IMIDAZOLE DERIVATIVE AND PROCESS FOR PRODUCING THE SAME |
| US5922751A (en) * | 1994-06-24 | 1999-07-13 | Euro-Celtique, S.A. | Aryl pyrazole compound for inhibiting phosphodiesterase IV and methods of using same |
| DE19541146A1 (de) * | 1995-10-25 | 1997-04-30 | Schering Ag | Imidazolderivate und deren Verwendung als Stickstoffmonoxid-Synthase-Inhibitoren |
| US6297239B1 (en) | 1997-10-08 | 2001-10-02 | Merck & Co., Inc. | Inhibitors of prenyl-protein transferase |
| WO2000034437A2 (en) | 1998-12-08 | 2000-06-15 | Merck & Co., Inc. | Inhibitors of prenyl-protein transferase |
| WO2001051494A1 (en) | 2000-01-12 | 2001-07-19 | Merck & Co., Inc. | Inhibitors of prenyl-protein transferase |
| EP1178038A1 (en) | 2000-08-04 | 2002-02-06 | Aventis Cropscience S.A. | Fungicidal phenylamidine derivatives |
| US7553837B2 (en) * | 2003-08-01 | 2009-06-30 | Nippon Soda Co., Ltd. | Phenylazole compounds production process and antioxidants |
| KR101320790B1 (ko) | 2009-04-20 | 2013-10-22 | 에프. 호프만-라 로슈 아게 | 카텝신 억제제로서의 프롤린 유도체 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1908991B2 (de) * | 1969-02-22 | 1977-05-26 | Bayer Ag, 5090 Leverkusen | Alpha, alpha-disubstituierte n- benzylimidazole und deren salze |
| DE2007794A1 (de) * | 1970-02-20 | 1971-09-02 | Farbenfabriken Bayer Aktiengesell schaft, 5090 Leverkusen | Fungizide Mittel |
| US3833603A (en) * | 1970-04-09 | 1974-09-03 | Bayer Ag | 1-(alpha,alpha-disubstituted 4-phenoxy-benzyl)imidazoles |
| NL7108387A (en, 2012) * | 1970-06-22 | 1971-12-24 | Koninklijke Pharma Fab Nv | |
| US3927017A (en) * | 1974-06-27 | 1975-12-16 | Janssen Pharmaceutica Nv | 1-({62 -Aryl-{62 -R-ethyl)imidazoles |
-
1975
- 1975-04-08 IE IE780/75A patent/IE40911B1/xx unknown
- 1975-04-09 CS CS752431A patent/CS194221B2/cs unknown
- 1975-04-09 DK DK153075A patent/DK139909C/da not_active IP Right Cessation
- 1975-04-09 DD DD185337A patent/DD121515A5/xx unknown
- 1975-04-09 YU YU00898/75A patent/YU89875A/xx unknown
- 1975-04-09 AT AT268675A patent/AT341518B/de not_active IP Right Cessation
- 1975-04-10 HU HU75SC00000516A patent/HU172895B/hu unknown
- 1975-04-10 IL IL7547061A patent/IL47061A/xx unknown
- 1975-04-10 SE SE7504123A patent/SE418498B/xx unknown
- 1975-04-10 CH CH457575A patent/CH612185A5/xx not_active IP Right Cessation
- 1975-04-11 GB GB15012/75A patent/GB1510016A/en not_active Expired
- 1975-04-11 ES ES75436546A patent/ES436546A1/es not_active Expired
- 1975-04-11 US US05/567,361 patent/US4006243A/en not_active Expired - Lifetime
- 1975-04-11 JP JP50044147A patent/JPS6018654B2/ja not_active Expired
- 1975-04-11 CA CA224,402A patent/CA1051908A/en not_active Expired
- 1975-04-11 FR FR7511415A patent/FR2267101B1/fr not_active Expired
- 1975-04-11 NL NL7504387A patent/NL7504387A/xx not_active Application Discontinuation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4448781A (en) * | 1979-01-19 | 1984-05-15 | Pfizer Inc. | N-Benzyl-imidazoles as selective inhibitors of the thromboxane synthetase enzyme |
| US4555516A (en) * | 1979-01-19 | 1985-11-26 | Pfizer Inc. | N-Benzyl-imidazoles as selective inhibitors of the thromboxane synthetase enzyme |
| GB2126218A (en) * | 1982-08-14 | 1984-03-21 | Wellcome Found | Imidazoles |
| EP0247725A3 (en) * | 1986-04-29 | 1990-01-17 | Pfizer Inc. | Calcium independent camp phosphodiestrerase inhibitor antidepressant |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7504387A (nl) | 1975-10-14 |
| CH612185A5 (en, 2012) | 1979-07-13 |
| IL47061A0 (en) | 1975-06-25 |
| ES436546A1 (es) | 1977-01-16 |
| AT341518B (de) | 1978-02-10 |
| IE40911L (en) | 1975-10-11 |
| SE7504123L (sv) | 1975-12-19 |
| YU89875A (en) | 1982-05-31 |
| JPS50148357A (en, 2012) | 1975-11-27 |
| ATA268675A (de) | 1977-06-15 |
| HU172895B (hu) | 1978-12-28 |
| CS194221B2 (en) | 1979-11-30 |
| DK153075A (en, 2012) | 1975-10-12 |
| DK139909C (da) | 1979-10-08 |
| DK139909B (da) | 1979-05-14 |
| FR2267101B1 (en, 2012) | 1980-01-25 |
| IL47061A (en) | 1978-08-31 |
| FR2267101A1 (en, 2012) | 1975-11-07 |
| IE40911B1 (en) | 1979-09-12 |
| JPS6018654B2 (ja) | 1985-05-11 |
| DD121515A5 (en, 2012) | 1976-08-05 |
| SE418498B (sv) | 1981-06-09 |
| US4006243A (en) | 1977-02-01 |
| AU8002575A (en) | 1976-10-14 |
| CA1051908A (en) | 1979-04-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |