CA1073455A - (aroyl-2'eth-1'yl)-1 (acetamido-4"piperazin-1"methyl)-2 benzimidazoles, leur application en therapeutique et leur procede de preparation_______ - Google Patents
(aroyl-2'eth-1'yl)-1 (acetamido-4"piperazin-1"methyl)-2 benzimidazoles, leur application en therapeutique et leur procede de preparation_______Info
- Publication number
- CA1073455A CA1073455A CA243,226A CA243226A CA1073455A CA 1073455 A CA1073455 A CA 1073455A CA 243226 A CA243226 A CA 243226A CA 1073455 A CA1073455 A CA 1073455A
- Authority
- CA
- Canada
- Prior art keywords
- group
- formula
- carbon atoms
- alpha
- alkyl group
- 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
- 101100513046 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) eth-1 gene Proteins 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- -1 or a group Chemical group 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 238000009833 condensation Methods 0.000 claims abstract description 3
- 230000005494 condensation Effects 0.000 claims abstract description 3
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 2
- 229960005141 piperazine Drugs 0.000 claims 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
- 125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 230000000767 anti-ulcer Effects 0.000 abstract description 6
- 230000002496 gastric effect Effects 0.000 abstract description 6
- 230000002048 spasmolytic effect Effects 0.000 abstract description 6
- 230000001262 anti-secretory effect Effects 0.000 abstract description 5
- 238000001727 in vivo Methods 0.000 abstract description 5
- 239000000812 cholinergic antagonist Substances 0.000 abstract description 3
- 230000000202 analgesic effect Effects 0.000 abstract description 2
- 230000002686 anti-diuretic effect Effects 0.000 abstract description 2
- 230000003276 anti-hypertensive effect Effects 0.000 abstract description 2
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
- 230000001078 anti-cholinergic effect Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 208000025865 Ulcer Diseases 0.000 description 4
- 231100000397 ulcer Toxicity 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- LCTZPQRFOZKZNK-UHFFFAOYSA-N 4-(diphenylmethylene)-1,1-dimethylpiperidin-1-ium Chemical compound C1C[N+](C)(C)CCC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 LCTZPQRFOZKZNK-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 206010006482 Bronchospasm Diseases 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000007885 bronchoconstriction Effects 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 229960005116 diphemanil Drugs 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- 125000006197 2-benzoyl ethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(=O)C([H])([H])C([H])([H])* 0.000 description 1
- UYWWLYCGNNCLKE-UHFFFAOYSA-N 2-pyridin-4-yl-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1C1=CC=NC=C1 UYWWLYCGNNCLKE-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010008583 Chloroma Diseases 0.000 description 1
- 101001126084 Homo sapiens Piwi-like protein 2 Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 231100000111 LD50 Toxicity 0.000 description 1
- 241000252067 Megalops atlanticus Species 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- 102100029365 Piwi-like protein 2 Human genes 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 206010042220 Stress ulcer Diseases 0.000 description 1
- GYMWQLRSSDFGEQ-ADRAWKNSSA-N [(3e,8r,9s,10r,13s,14s,17r)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate;(8r,9s,13s,14s,17r)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17-diol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1.O/N=C/1CC[C@@H]2[C@H]3CC[C@](CC)([C@](CC4)(OC(C)=O)C#C)[C@@H]4[C@@H]3CCC2=C\1 GYMWQLRSSDFGEQ-ADRAWKNSSA-N 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
- 239000004480 active ingredient Substances 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000011038 discontinuous diafiltration by volume reduction Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 210000001630 jejunum Anatomy 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000000793 phophlogistic effect Effects 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 230000009278 visceral effect Effects 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/10—Radicals substituted by halogen atoms or nitro radicals
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7500724A FR2297045A1 (fr) | 1975-01-10 | 1975-01-10 | Nouveaux (aroyl-2' eth-1' yl)-1 (acetamido-4'' piperazin-1'' yl methyl)-2 benzimidazoles a proprietes antisecretoire gastrique et antiulcereuse |
| FR7537297A FR2333510A2 (fr) | 1975-12-05 | 1975-12-05 | Nouveaux (aroyl-2' eth-1 yl)-1 (acetamido-4'' piperazin-1'' yl methyl)-2 benzimidazoles, leur application en therapeutique et leur procede de preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1073455A true CA1073455A (fr) | 1980-03-11 |
Family
ID=26218682
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA243,226A Expired CA1073455A (fr) | 1975-01-10 | 1976-01-08 | (aroyl-2'eth-1'yl)-1 (acetamido-4"piperazin-1"methyl)-2 benzimidazoles, leur application en therapeutique et leur procede de preparation_______ |
Country Status (13)
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2190439B1 (enrdf_load_html_response) * | 1972-07-06 | 1975-06-20 | Delalande Sa |
-
1975
- 1975-12-16 GB GB51396/75A patent/GB1487128A/en not_active Expired
- 1975-12-18 LU LU74043A patent/LU74043A1/xx unknown
- 1975-12-19 DE DE2557446A patent/DE2557446C2/de not_active Expired
-
1976
- 1976-01-03 ES ES444064A patent/ES444064A1/es not_active Expired
- 1976-01-06 MX MX001645U patent/MX3428E/es unknown
- 1976-01-07 CH CH12876A patent/CH612675A5/xx not_active IP Right Cessation
- 1976-01-08 AU AU10117/76A patent/AU509084B2/en not_active Expired
- 1976-01-08 SU SU762305959A patent/SU651701A3/ru active
- 1976-01-08 CA CA243,226A patent/CA1073455A/fr not_active Expired
- 1976-01-08 SE SE7600116A patent/SE421527B/xx unknown
- 1976-01-08 JP JP761833A patent/JPS6020386B2/ja not_active Expired
- 1976-01-09 IT IT67044/76A patent/IT1062803B/it active
- 1976-01-09 NL NL7600224A patent/NL7600224A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IT1062803B (it) | 1985-02-11 |
| MX3428E (es) | 1980-11-21 |
| ES444064A1 (es) | 1977-08-16 |
| NL7600224A (nl) | 1976-07-13 |
| AU509084B2 (en) | 1980-04-17 |
| LU74043A1 (enrdf_load_html_response) | 1976-11-11 |
| JPS6020386B2 (ja) | 1985-05-21 |
| AU1011776A (en) | 1977-07-14 |
| SU651701A3 (ru) | 1979-03-05 |
| SE7600116L (sv) | 1976-07-12 |
| CH612675A5 (en) | 1979-08-15 |
| DE2557446C2 (de) | 1984-11-29 |
| GB1487128A (en) | 1977-09-28 |
| DE2557446A1 (de) | 1976-07-15 |
| JPS51131885A (en) | 1976-11-16 |
| SE421527B (sv) | 1982-01-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4207324A (en) | 1,2-Di-Substituted-4-haloimidazole-5-acetic acid derivatives and their use | |
| PL143010B1 (en) | Process for preparing novel derivatives of 1,2,3,5-tetrahydroimidazo/2,1-b/quinazoline | |
| FR2503155A2 (fr) | Nouveaux imino diacides substitues, leurs procedes de preparation et leur emploi comme inhibiteur d'enzyme | |
| EP0385850A2 (fr) | Nouveaux dérivés de benzimidazoles et azabenzimidazoles, leurs procédés de préparation, intermédiaires de synthèse, compositions pharmaceutiques les contenant, utiles notamment pour le traitement des maladies cardiovasculaires, et les ulcères duodénaux | |
| CH618975A5 (enrdf_load_html_response) | ||
| FR2673182A1 (fr) | Piperazines n,n'-disubstituees, leur procede de preparation et leur application en therapeutique. | |
| LU83400A1 (fr) | Nouvelles n-aryl oxazolidinones-2,leur procede de preparation et leur application en therapeutique | |
| JPS63310872A (ja) | ドーパミン−β−ヒドロキシラーゼ抑制剤 | |
| CA1073455A (fr) | (aroyl-2'eth-1'yl)-1 (acetamido-4"piperazin-1"methyl)-2 benzimidazoles, leur application en therapeutique et leur procede de preparation_______ | |
| JPH04282374A (ja) | 新規５ｈ−ベンゾジアゼピン誘導体、それを含有してなる製剤組成物、およびそれらの製造方法 | |
| CA2059311A1 (fr) | Composes de structure aryltriazinique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
| CH632268A5 (de) | Verfahren zur herstellung von neuen heterocyclylaminoderivaten. | |
| EP0008259A1 (fr) | Nouveaux dérivés de la pipéridylbenzimidazolinone, leurs procédés de préparation et les compositions pharmaceutiques les renfermant | |
| EP0209435B1 (fr) | Dérivés de l'hydroxy alkoxy 4-phénylpropyl indole, leurs sels, procédé et intermédiaires de préparation, application à titre de médicaments et compositions les renfermant | |
| CH497433A (fr) | Procédé de préparation de nouveaux dérivés des benzimidazoles | |
| EP0502110B1 (fr) | Derives d'(hetero) arylmethyloxy-4 phenyl diazole, leur procede de preparation et leur application en therapeutique | |
| CA2306428C (fr) | Derives de la 3-oxo-2(h)-1,2,4 - triazine en tant que ligands des recepteurs 5ht1a | |
| CZ357190A3 (en) | Dihydropyrimidothiazine derivatives, process of their preparation and pharmaceutical compositions containing thereof | |
| EP0282390A1 (fr) | Nouveaux dérivés de l'acide (dihydro-2,3 oxo-2 benzofurannyl-3)-2 acétique et les compositions pharmaceutiques qui les contiennent | |
| US3281468A (en) | beta-phenyl-beta-hydroxyethylamines | |
| LT4457B (lt) | Nauji pasižymintys antispazminiu aktyvumu imidazolin-2,4-dionai, turintys orto-pakeistą aril(alkil)-radikalą 1 padėtyje, ir jų gavimo būdas | |
| US5322846A (en) | 4-methylthiazole derivatives, their methods of preparation and the pharmaceutical compositions in which they are present | |
| EP0347305B1 (fr) | [(Aryl-4-pipérazinyl-1)-2 éthoxy]-3 p-cymène, les dérivés ortho, méta, para monosubstitués ou disubstitués sur le noyau phényle dudit produit, le procédé de préparation desdits dérivés, et les médicaments contenant lesdits composés comme principe actif | |
| EP0275221B1 (fr) | Nouveaux dérivés du N-(1H-indol 4-yl) benzamide ainsi que leurs sels, leur application à titre de médicaments et les compositions les renfermant | |
| BE819057A (fr) | Nouveaux derives arylamino pyrimidiniques |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |