DE2161209A1 - Substituierte Imidazole, ihre pharmakologisch verträglichen Salze, Verfahren zu ihrer Herstellung, und diese Verbindungen enthaltende Arzneipräparate - Google Patents
Substituierte Imidazole, ihre pharmakologisch verträglichen Salze, Verfahren zu ihrer Herstellung, und diese Verbindungen enthaltende ArzneipräparateInfo
- Publication number
- DE2161209A1 DE2161209A1 DE19712161209 DE2161209A DE2161209A1 DE 2161209 A1 DE2161209 A1 DE 2161209A1 DE 19712161209 DE19712161209 DE 19712161209 DE 2161209 A DE2161209 A DE 2161209A DE 2161209 A1 DE2161209 A1 DE 2161209A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- radical
- methyl
- methoxy
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims description 57
- 238000000034 method Methods 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title claims description 17
- 150000002460 imidazoles Chemical class 0.000 title claims description 13
- 150000003839 salts Chemical class 0.000 title claims description 10
- -1 amino, hydroxyl Chemical group 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 9
- 125000001495 ethyl group Chemical class [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001302 tertiary amino group Chemical group 0.000 claims description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
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- 125000004429 atom Chemical group 0.000 claims 1
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- 239000000243 solution Substances 0.000 description 20
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
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- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
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- ZBNZAJFNDPPMDT-UHFFFAOYSA-N 1h-imidazole-5-carboxamide Chemical compound NC(=O)C1=CNC=N1 ZBNZAJFNDPPMDT-UHFFFAOYSA-N 0.000 description 2
- ZHQFCIVAXUTIGP-UHFFFAOYSA-N 2-(aminodiazenyl)-1H-imidazole Chemical compound NN=NC1=NC=CN1 ZHQFCIVAXUTIGP-UHFFFAOYSA-N 0.000 description 2
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- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
Classifications
-
- 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
- C07D233/66—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/52—Nitrogen atoms not forming part of a nitro radical with hetero atoms directly attached to said nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5838570A GB1373346A (en) | 1970-12-09 | 1970-12-09 | Biologically active imidazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2161209A1 true DE2161209A1 (de) | 1972-06-22 |
Family
ID=10481482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712161209 Pending DE2161209A1 (de) | 1970-12-09 | 1971-12-09 | Substituierte Imidazole, ihre pharmakologisch verträglichen Salze, Verfahren zu ihrer Herstellung, und diese Verbindungen enthaltende Arzneipräparate |
Country Status (13)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3720437A4 (en) * | 2017-12-06 | 2021-11-03 | Yale University | MEDICINAL PRODUCTS ACTIVATED BY REDUCTION IN CYTOSOL |
-
1970
- 1970-12-09 GB GB5838570A patent/GB1373346A/en not_active Expired
-
1971
- 1971-11-17 IE IE1448/71A patent/IE35817B1/xx unknown
- 1971-11-18 IL IL38174A patent/IL38174A0/xx unknown
- 1971-11-23 ZA ZA717873A patent/ZA717873B/xx unknown
- 1971-11-26 CA CA128,705A patent/CA979428A/en not_active Expired
- 1971-11-26 NL NL7116331A patent/NL7116331A/xx unknown
- 1971-12-01 ES ES397573A patent/ES397573A1/es not_active Expired
- 1971-12-03 AT AT1042171A patent/AT310740B/de not_active IP Right Cessation
- 1971-12-08 FR FR7144014A patent/FR2117939B1/fr not_active Expired
- 1971-12-08 BE BE776422A patent/BE776422A/xx unknown
- 1971-12-09 HU HUBE1108A patent/HU163484B/hu unknown
- 1971-12-09 DE DE19712161209 patent/DE2161209A1/de active Pending
-
1974
- 1974-10-02 SE SE7412430A patent/SE7412430L/xx not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3720437A4 (en) * | 2017-12-06 | 2021-11-03 | Yale University | MEDICINAL PRODUCTS ACTIVATED BY REDUCTION IN CYTOSOL |
Also Published As
| Publication number | Publication date |
|---|---|
| BE776422A (fr) | 1972-06-08 |
| IE35817B1 (en) | 1976-05-26 |
| ES397573A1 (es) | 1975-10-01 |
| IE35817L (en) | 1972-06-09 |
| AT310740B (de) | 1973-10-10 |
| IL38174A0 (en) | 1972-01-27 |
| SE7412430L (enrdf_load_stackoverflow) | 1974-10-02 |
| CA979428A (en) | 1975-12-09 |
| NL7116331A (enrdf_load_stackoverflow) | 1972-06-13 |
| ZA717873B (en) | 1972-08-30 |
| FR2117939A1 (enrdf_load_stackoverflow) | 1972-07-28 |
| GB1373346A (en) | 1974-11-13 |
| HU163484B (enrdf_load_stackoverflow) | 1973-09-27 |
| FR2117939B1 (enrdf_load_stackoverflow) | 1975-06-13 |
| AU3658871A (en) | 1973-06-14 |
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