DE1908991B2 - Alpha, alpha-disubstituierte n- benzylimidazole und deren salze - Google Patents
Alpha, alpha-disubstituierte n- benzylimidazole und deren salzeInfo
- Publication number
- DE1908991B2 DE1908991B2 DE19691908991 DE1908991A DE1908991B2 DE 1908991 B2 DE1908991 B2 DE 1908991B2 DE 19691908991 DE19691908991 DE 19691908991 DE 1908991 A DE1908991 A DE 1908991A DE 1908991 B2 DE1908991 B2 DE 1908991B2
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- butyl
- hcl
- cyclopropyl
- salts
- 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.)
- Granted
Links
- 150000003839 salts Chemical class 0.000 title claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 22
- -1 alkyl radical Chemical class 0.000 claims description 21
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 5
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 21
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
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- 240000004808 Saccharomyces cerevisiae Species 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
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- 125000004344 phenylpropyl group Chemical group 0.000 description 5
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- IIUZTXTZRGLYTI-UHFFFAOYSA-N Dihydrogriseofulvin Natural products COC1CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 IIUZTXTZRGLYTI-UHFFFAOYSA-N 0.000 description 4
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- DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 description 4
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- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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- 230000037396 body weight Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
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- 230000001225 therapeutic effect Effects 0.000 description 3
- KKKDZZRICRFGSD-UHFFFAOYSA-N 1-benzylimidazole Chemical class C1=CN=CN1CC1=CC=CC=C1 KKKDZZRICRFGSD-UHFFFAOYSA-N 0.000 description 2
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 2
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- 241000700198 Cavia Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- 208000031888 Mycoses Diseases 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
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- 125000006450 cyclopropyl cyclopropyl group Chemical group 0.000 description 2
- 229940127089 cytotoxic agent Drugs 0.000 description 2
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- 235000014655 lactic acid Nutrition 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- XFDFELYDTUQBDS-UHFFFAOYSA-N 2-butan-2-yl-1h-imidazole Chemical compound CCC(C)C1=NC=CN1 XFDFELYDTUQBDS-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
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- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 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
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Fodder In General (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691908991 DE1908991B2 (de) | 1969-02-22 | 1969-02-22 | Alpha, alpha-disubstituierte n- benzylimidazole und deren salze |
| BR215373/69A BR6915373D0 (pt) | 1969-02-22 | 1969-12-19 | Processo para a preparacao de benzimidazois alfa-dissibstituido e seus sais |
| CH165870A CH560196A5 (forum.php) | 1969-02-22 | 1970-02-05 | |
| IL33856A IL33856A (en) | 1969-02-22 | 1970-02-09 | Alpha,alpha-disubstituted benzylimidazoles and their salts,their preparation and pharmaceutical compositions containing them |
| SE7002068A SE375992B (forum.php) | 1969-02-22 | 1970-02-18 | |
| JP45013899A JPS4941197B1 (forum.php) | 1969-02-22 | 1970-02-19 | |
| FI445/70A FI55191C (fi) | 1969-02-22 | 1970-02-19 | Foerfarande foer framstaellning av mot patogena svampar verksamma alfa alfa-disubstituerade n-bensylimidazoler och deras salter |
| GB803070A GB1304623A (forum.php) | 1969-02-22 | 1970-02-19 | |
| NL7002356A NL167960C (nl) | 1969-02-22 | 1970-02-19 | Werkwijze voor de bereiding van nieuwe alfa,alfa-digesubstitueerde n-benzylimidazolen en van farmaceutische preparaten, die ten minste een van deze verbindingen bevatten. |
| US00012830A US3711487A (en) | 1969-02-22 | 1970-02-19 | Certain alpha,alpha-disubstituted benzylimidazoles and salts |
| LU60382D LU60382A1 (forum.php) | 1969-02-22 | 1970-02-20 | |
| CA075427A CA925081A (en) | 1969-02-22 | 1970-02-20 | CERTAIN .alpha., .alpha.-DISUBSTITUTED BENZYLIMIDAZOLES AND SALTS |
| FR7006242A FR2034562B1 (forum.php) | 1969-02-22 | 1970-02-20 | |
| AT156570A AT293380B (de) | 1969-02-22 | 1970-02-20 | Verfahren zur Herstellung neuer α,α-disubstituierter Benzylimidazole und ihrer Säureadditionssalze |
| BE746301D BE746301A (fr) | 1969-02-22 | 1970-02-20 | Nouveaux benzylimidazoles alpha, alpha-disubstitues, leur procede de preparation et compositions pharmaceutiques les contenant |
| ES376790A ES376790A1 (es) | 1969-02-22 | 1970-02-21 | Procedimiento para la obtencion de bencilimidazoles alfa, alfa-disustituidos. |
| PL1970138941A PL80618B1 (forum.php) | 1969-02-22 | 1970-02-21 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691908991 DE1908991B2 (de) | 1969-02-22 | 1969-02-22 | Alpha, alpha-disubstituierte n- benzylimidazole und deren salze |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1908991A1 DE1908991A1 (de) | 1970-09-03 |
| DE1908991B2 true DE1908991B2 (de) | 1977-05-26 |
| DE1908991C3 DE1908991C3 (forum.php) | 1978-01-19 |
Family
ID=5726054
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691908991 Granted DE1908991B2 (de) | 1969-02-22 | 1969-02-22 | Alpha, alpha-disubstituierte n- benzylimidazole und deren salze |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3711487A (forum.php) |
| JP (1) | JPS4941197B1 (forum.php) |
| AT (1) | AT293380B (forum.php) |
| BE (1) | BE746301A (forum.php) |
| BR (1) | BR6915373D0 (forum.php) |
| CA (1) | CA925081A (forum.php) |
| CH (1) | CH560196A5 (forum.php) |
| DE (1) | DE1908991B2 (forum.php) |
| ES (1) | ES376790A1 (forum.php) |
| FI (1) | FI55191C (forum.php) |
| FR (1) | FR2034562B1 (forum.php) |
| GB (1) | GB1304623A (forum.php) |
| IL (1) | IL33856A (forum.php) |
| LU (1) | LU60382A1 (forum.php) |
| NL (1) | NL167960C (forum.php) |
| PL (1) | PL80618B1 (forum.php) |
| SE (1) | SE375992B (forum.php) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2007794A1 (de) * | 1970-02-20 | 1971-09-02 | Farbenfabriken Bayer Aktiengesell schaft, 5090 Leverkusen | Fungizide Mittel |
| DE2213863C3 (de) * | 1972-03-22 | 1982-05-13 | Bayer Ag, 5090 Leverkusen | Disubstituierte Triphenylmethylimidazole, Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel |
| DE2229128C2 (de) * | 1972-06-15 | 1983-02-10 | Bayer Ag, 5090 Leverkusen | 1-(Dialkylphenyl-phenyl-pyridyl-)methyl-imidazole, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| IE40911B1 (en) * | 1974-04-11 | 1979-09-12 | Schering Ag | Imidazole derivatives and process for their manufacture |
| US4237158A (en) * | 1975-02-05 | 1980-12-02 | Rohm And Haas Company | 1-Substituted aralkyl imidazoles and their use as fungicides |
| US4115578A (en) * | 1975-12-18 | 1978-09-19 | Rohm And Haas Company | 1-Substituted aralkyl imidazoles |
| US4118461A (en) * | 1975-12-18 | 1978-10-03 | Rohm And Haas Company | 1-Substituted aralkyl imidazoles |
| DE2732531A1 (de) * | 1977-07-19 | 1979-02-01 | Hoechst Ag | Imidazolcarbonsaeuren und deren derivate |
| GB2008089B (en) * | 1977-08-26 | 1982-06-09 | Wellcome Found | Imidazole derivatives and salts thereof their synthesis and intermediates and pharmaceutical formulations |
| US4755526A (en) * | 1984-06-18 | 1988-07-05 | Eli Lilly And Company | Method of inhibiting aromatase |
| US4749713A (en) * | 1986-03-07 | 1988-06-07 | Ciba-Geigy Corporation | Alpha-heterocycle substituted tolunitriles |
| US4978672A (en) * | 1986-03-07 | 1990-12-18 | Ciba-Geigy Corporation | Alpha-heterocyclc substituted tolunitriles |
| US4937250A (en) * | 1988-03-07 | 1990-06-26 | Ciba-Geigy Corporation | Alpha-heterocycle substituted tolunitriles |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3321366A (en) * | 1965-11-15 | 1967-05-23 | Dow Chemical Co | Fungicidal methods and compositions |
-
1969
- 1969-02-22 DE DE19691908991 patent/DE1908991B2/de active Granted
- 1969-12-19 BR BR215373/69A patent/BR6915373D0/pt unknown
-
1970
- 1970-02-05 CH CH165870A patent/CH560196A5/xx not_active IP Right Cessation
- 1970-02-09 IL IL33856A patent/IL33856A/xx unknown
- 1970-02-18 SE SE7002068A patent/SE375992B/xx unknown
- 1970-02-19 US US00012830A patent/US3711487A/en not_active Expired - Lifetime
- 1970-02-19 NL NL7002356A patent/NL167960C/xx active
- 1970-02-19 JP JP45013899A patent/JPS4941197B1/ja active Pending
- 1970-02-19 GB GB803070A patent/GB1304623A/en not_active Expired
- 1970-02-19 FI FI445/70A patent/FI55191C/fi active
- 1970-02-20 LU LU60382D patent/LU60382A1/xx unknown
- 1970-02-20 BE BE746301D patent/BE746301A/xx not_active IP Right Cessation
- 1970-02-20 CA CA075427A patent/CA925081A/en not_active Expired
- 1970-02-20 FR FR7006242A patent/FR2034562B1/fr not_active Expired
- 1970-02-20 AT AT156570A patent/AT293380B/de not_active IP Right Cessation
- 1970-02-21 PL PL1970138941A patent/PL80618B1/pl unknown
- 1970-02-21 ES ES376790A patent/ES376790A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2034562B1 (forum.php) | 1974-02-01 |
| IL33856A0 (en) | 1970-04-20 |
| IL33856A (en) | 1974-05-16 |
| CA925081A (en) | 1973-04-24 |
| AT293380B (de) | 1971-10-11 |
| ES376790A1 (es) | 1972-05-01 |
| GB1304623A (forum.php) | 1973-01-24 |
| FR2034562A1 (forum.php) | 1970-12-11 |
| CH560196A5 (forum.php) | 1975-03-27 |
| SE375992B (forum.php) | 1975-05-05 |
| NL167960C (nl) | 1982-02-16 |
| PL80618B1 (forum.php) | 1975-08-30 |
| DE1908991A1 (de) | 1970-09-03 |
| FI55191B (fi) | 1979-02-28 |
| BE746301A (fr) | 1970-08-20 |
| JPS4941197B1 (forum.php) | 1974-11-07 |
| US3711487A (en) | 1973-01-16 |
| NL7002356A (forum.php) | 1970-08-25 |
| BR6915373D0 (pt) | 1973-01-04 |
| NL167960B (nl) | 1981-09-16 |
| LU60382A1 (forum.php) | 1970-04-22 |
| FI55191C (fi) | 1979-06-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |