CA1088947A - Imidazole compound and its process of preparation - Google Patents
Imidazole compound and its process of preparationInfo
- Publication number
- CA1088947A CA1088947A CA278,432A CA278432A CA1088947A CA 1088947 A CA1088947 A CA 1088947A CA 278432 A CA278432 A CA 278432A CA 1088947 A CA1088947 A CA 1088947A
- Authority
- CA
- Canada
- Prior art keywords
- chlorophenazole
- rats
- phenylbutazone
- activity
- compound
- 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
- 238000000034 method Methods 0.000 title claims description 9
- 230000008569 process Effects 0.000 title claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 4
- -1 Imidazole compound Chemical class 0.000 title description 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims abstract description 10
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 15
- 230000000202 analgesic effect Effects 0.000 abstract description 7
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 4
- 239000002221 antipyretic Substances 0.000 abstract description 4
- 239000000730 antalgic agent Substances 0.000 abstract description 3
- 239000002260 anti-inflammatory agent Substances 0.000 abstract description 2
- 229940125716 antipyretic agent Drugs 0.000 abstract description 2
- 241000700159 Rattus Species 0.000 description 23
- 229960002895 phenylbutazone Drugs 0.000 description 23
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 23
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 14
- 229940079593 drug Drugs 0.000 description 11
- 239000003814 drug Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 241000206575 Chondrus crispus Species 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
- JZFPYUNJRRFVQU-UHFFFAOYSA-N Niflumic acid Chemical compound OC(=O)C1=CC=CN=C1NC1=CC=CC(C(F)(F)F)=C1 JZFPYUNJRRFVQU-UHFFFAOYSA-N 0.000 description 8
- 229960000916 niflumic acid Drugs 0.000 description 8
- 229960005181 morphine Drugs 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- 206010030113 Oedema Diseases 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 4
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 229960002275 pentobarbital sodium Drugs 0.000 description 4
- 230000007958 sleep Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 230000001754 anti-pyretic effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- CLOMYZFHNHFSIQ-UHFFFAOYSA-N clonixin Chemical compound CC1=C(Cl)C=CC=C1NC1=NC=CC=C1C(O)=O CLOMYZFHNHFSIQ-UHFFFAOYSA-N 0.000 description 3
- 229960001209 clonixin Drugs 0.000 description 3
- 210000000416 exudates and transudate Anatomy 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000011514 reflex Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 2
- 229930003347 Atropine Natural products 0.000 description 2
- 208000037157 Azotemia Diseases 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 2
- 208000001953 Hypotension Diseases 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000036592 analgesia Effects 0.000 description 2
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 2
- 229960000396 atropine Drugs 0.000 description 2
- 229940125717 barbiturate Drugs 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000002526 effect on cardiovascular system Effects 0.000 description 2
- 230000036543 hypotension Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 230000001962 neuropharmacologic effect Effects 0.000 description 2
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 2
- 229960002748 norepinephrine Drugs 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 230000001052 transient effect Effects 0.000 description 2
- QJVOZXGJOGJKPT-IGHBBLSQSA-N (1r,2r,5s,11ar)-2-(prop-2-en-1-yl)-1,2,3,4,5,6,11,11a-octahydro-10h-1,5-methanopyrido[1,2-a][1,5]diazocin-10-one Chemical compound C([C@@H]12)C(=O)C=CN1C[C@@H]1CN[C@H](CC=C)[C@H]2C1 QJVOZXGJOGJKPT-IGHBBLSQSA-N 0.000 description 1
- GOOCRIHPADOQAS-ZNUXJMJHSA-N (4ar,5as,8ar,13as,15as,15br)-4a,5,5a,7,8,13a,15,15a,15b,16-decahydro-2h-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinoline-14-one;sulfuric acid Chemical compound OS(O)(=O)=O.O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1.O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 GOOCRIHPADOQAS-ZNUXJMJHSA-N 0.000 description 1
- DRUDFLDRXVNBRY-UHFFFAOYSA-N 2-chloro-2h-phenazin-1-one Chemical compound C1=CC=C2N=C(C(C(Cl)C=C3)=O)C3=NC2=C1 DRUDFLDRXVNBRY-UHFFFAOYSA-N 0.000 description 1
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 206010048964 Carotid artery occlusion Diseases 0.000 description 1
- 102000001554 Hemoglobins Human genes 0.000 description 1
- 108010054147 Hemoglobins Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010021113 Hypothermia Diseases 0.000 description 1
- 208000007379 Muscle Hypotonia Diseases 0.000 description 1
- 208000027419 Muscular hypotonia Diseases 0.000 description 1
- 241001464937 Neisseria perflava Species 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 208000010476 Respiratory Paralysis Diseases 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- UFLGIAIHIAPJJC-UHFFFAOYSA-N Tripelennamine Chemical compound C=1C=CC=NC=1N(CCN(C)C)CC1=CC=CC=C1 UFLGIAIHIAPJJC-UHFFFAOYSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- QJVOZXGJOGJKPT-UHFFFAOYSA-N albine Natural products C12CC(=O)C=CN2CC2CNC(CC=C)C1C2 QJVOZXGJOGJKPT-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000003501 anti-edematous effect Effects 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 206010007776 catatonia Diseases 0.000 description 1
- 230000009956 central mechanism Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 239000003179 convulsant agent Substances 0.000 description 1
- 230000002920 convulsive effect Effects 0.000 description 1
- 229940109239 creatinine Drugs 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 229960003699 evans blue Drugs 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005534 hematocrit Methods 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 229960005195 morphine hydrochloride Drugs 0.000 description 1
- XELXKCKNPPSFNN-BJWPBXOKSA-N morphine hydrochloride trihydrate Chemical compound O.O.O.Cl.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O XELXKCKNPPSFNN-BJWPBXOKSA-N 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 229960005152 pentetrazol Drugs 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000009955 peripheral mechanism Effects 0.000 description 1
- 210000003281 pleural cavity Anatomy 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 230000036578 sleeping time Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 229960003223 tripelennamine Drugs 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 238000005353 urine analysis Methods 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 238000009423 ventilation Methods 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
- C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7614381 | 1976-05-13 | ||
| FR7614381A FR2350839A1 (fr) | 1976-05-13 | 1976-05-13 | Nouveau compose imidazolique, procede pour sa preparation et compositions therapeutiques qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1088947A true CA1088947A (en) | 1980-11-04 |
Family
ID=9173064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA278,432A Expired CA1088947A (en) | 1976-05-13 | 1977-05-12 | Imidazole compound and its process of preparation |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4499104A (en:Method) |
| JP (1) | JPS5321162A (en:Method) |
| BE (1) | BE864833A (en:Method) |
| CA (1) | CA1088947A (en:Method) |
| DE (1) | DE2721835C2 (en:Method) |
| FR (1) | FR2350839A1 (en:Method) |
| GB (1) | GB1527700A (en:Method) |
| IL (1) | IL51938A (en:Method) |
| NZ (1) | NZ183934A (en:Method) |
| YU (1) | YU112277A (en:Method) |
| ZA (1) | ZA772370B (en:Method) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH524613A (de) * | 1969-12-31 | 1972-06-30 | Ciba Geigy Ag | Verfahren zur Herstellung von neuen Imidazolderivaten |
| US3657441A (en) * | 1970-07-30 | 1972-04-18 | Merck & Co Inc | Method of inhibiting the formation of phenylethanolamine n-methyl transferase with imidazoles |
| FR2115153A1 (en) * | 1970-11-30 | 1972-07-07 | Berlin Chemie Veb | 1-acyl-imidazoles - with antiviral activity |
| US4152441A (en) * | 1972-02-04 | 1979-05-01 | Gist-Brocades N.V. | Analgesic imidazolemethanols |
-
1976
- 1976-05-13 FR FR7614381A patent/FR2350839A1/fr active Granted
-
1977
- 1977-04-19 ZA ZA00772370A patent/ZA772370B/xx unknown
- 1977-04-25 IL IL51938A patent/IL51938A/xx unknown
- 1977-04-26 NZ NZ183934A patent/NZ183934A/xx unknown
- 1977-05-04 YU YU01122/77A patent/YU112277A/xx unknown
- 1977-05-12 CA CA278,432A patent/CA1088947A/en not_active Expired
- 1977-05-13 JP JP5448577A patent/JPS5321162A/ja active Granted
- 1977-05-13 GB GB20112/77A patent/GB1527700A/en not_active Expired
- 1977-05-13 DE DE2721835A patent/DE2721835C2/de not_active Expired
- 1977-05-31 US US05/796,532 patent/US4499104A/en not_active Expired - Lifetime
-
1978
- 1978-03-13 BE BE185887A patent/BE864833A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| YU112277A (en) | 1983-01-21 |
| IL51938A (en) | 1980-02-29 |
| FR2350839B1 (en:Method) | 1978-11-17 |
| US4499104A (en) | 1985-02-12 |
| ZA772370B (en) | 1978-06-28 |
| JPS5321162A (en) | 1978-02-27 |
| DE2721835C2 (de) | 1983-12-01 |
| BE864833A (fr) | 1978-07-03 |
| GB1527700A (en) | 1978-10-04 |
| IL51938A0 (en) | 1977-06-30 |
| JPS5420496B2 (en:Method) | 1979-07-23 |
| DE2721835A1 (de) | 1977-11-24 |
| NZ183934A (en) | 1978-12-18 |
| FR2350839A1 (fr) | 1977-12-09 |
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