CA1037031A - 8-n-methylpiperazinyl-n'-carbonyldibenzo-bicyclooctadiene and salts thereof - Google Patents
8-n-methylpiperazinyl-n'-carbonyldibenzo-bicyclooctadiene and salts thereofInfo
- Publication number
- CA1037031A CA1037031A CA193,621A CA193621A CA1037031A CA 1037031 A CA1037031 A CA 1037031A CA 193621 A CA193621 A CA 193621A CA 1037031 A CA1037031 A CA 1037031A
- Authority
- CA
- Canada
- Prior art keywords
- octadiene
- carbonyl
- methylpiperazinyl
- process according
- dibenzobicyclo
- 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
- 150000003839 salts Chemical class 0.000 title claims abstract description 16
- QTYUSOHYEPOHLV-FNORWQNLSA-N 1,3-Octadiene Chemical compound CCCC\C=C\C=C QTYUSOHYEPOHLV-FNORWQNLSA-N 0.000 claims abstract description 30
- 239000002253 acid Substances 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 6
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 5
- 150000001263 acyl chlorides Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 28
- 229940125723 sedative agent Drugs 0.000 abstract description 2
- 239000000932 sedative agent Substances 0.000 abstract description 2
- 239000003204 tranquilizing agent Substances 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 241000699670 Mus sp. Species 0.000 description 11
- 235000002639 sodium chloride Nutrition 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 6
- -1 chloro compound Chemical class 0.000 description 5
- 230000002936 tranquilizing effect Effects 0.000 description 5
- 229910001868 water Inorganic materials 0.000 description 5
- 238000007792 addition Methods 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 229960004424 carbon dioxide Drugs 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 229940025084 amphetamine Drugs 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 231100001274 therapeutic index Toxicity 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 235000001055 magnesium Nutrition 0.000 description 2
- 229940091250 magnesium supplement Drugs 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 244000186140 Asperula odorata Species 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 235000008526 Galium odoratum Nutrition 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229940008238 amphetamine sulfate Drugs 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000003137 locomotive effect Effects 0.000 description 1
- 230000006742 locomotor activity Effects 0.000 description 1
- 229960003390 magnesium sulfate Drugs 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- AQFGKZRFNWKFCA-UHFFFAOYSA-N n-methylpiperazin-1-amine Chemical class CNN1CCNCC1 AQFGKZRFNWKFCA-UHFFFAOYSA-N 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 231100001160 nonlethal Toxicity 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/39—Unsaturated compounds containing six-membered aromatic rings
-
- 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
- A61P25/20—Hypnotics; Sedatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Anesthesiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US339359A US3904630A (en) | 1973-03-08 | 1973-03-08 | 8-n-methylpiperazinyl-n'-carbonyldibenzo-bicyclooctadiene and salts thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1037031A true CA1037031A (en) | 1978-08-22 |
Family
ID=23328651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA193,621A Expired CA1037031A (en) | 1973-03-08 | 1974-02-27 | 8-n-methylpiperazinyl-n'-carbonyldibenzo-bicyclooctadiene and salts thereof |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3904630A (enrdf_load_stackoverflow) |
| JP (1) | JPS526998B2 (enrdf_load_stackoverflow) |
| AU (1) | AU467513B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1037031A (enrdf_load_stackoverflow) |
| DE (1) | DE2410982C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2220268B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1458892A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3976774A (en) * | 1975-06-02 | 1976-08-24 | Riker Laboratories, Inc. | Antiemetic method |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1813918C3 (de) * | 1968-12-11 | 1979-02-15 | Bayer Ag | 2-Hydroxymethyl-3-carbonsäureamido--chinoxalin-M-di-N-oxide, ein Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende antibakterielle Mittel |
| GB1250538A (enrdf_load_stackoverflow) * | 1969-03-18 | 1971-10-20 | ||
| FR2081507B1 (enrdf_load_stackoverflow) * | 1970-02-13 | 1974-10-18 | Ciba Geigy Ag | |
| FR2129838A1 (en) * | 1971-03-16 | 1972-11-03 | Boehringer Mannheim Gmbh | Diuretic/saluretic dibenzo cycloheptene - derivs |
-
1973
- 1973-03-08 US US339359A patent/US3904630A/en not_active Expired - Lifetime
-
1974
- 1974-02-27 CA CA193,621A patent/CA1037031A/en not_active Expired
- 1974-03-07 AU AU66373/74A patent/AU467513B2/en not_active Expired
- 1974-03-07 FR FR7407836A patent/FR2220268B1/fr not_active Expired
- 1974-03-07 DE DE2410982A patent/DE2410982C3/de not_active Expired
- 1974-03-07 JP JP49026718A patent/JPS526998B2/ja not_active Expired
- 1974-03-07 GB GB1029974A patent/GB1458892A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU467513B2 (en) | 1975-12-04 |
| JPS526998B2 (enrdf_load_stackoverflow) | 1977-02-26 |
| DE2410982B2 (de) | 1981-01-15 |
| FR2220268A1 (enrdf_load_stackoverflow) | 1974-10-04 |
| JPS49124084A (enrdf_load_stackoverflow) | 1974-11-27 |
| AU6637374A (en) | 1975-09-11 |
| US3904630A (en) | 1975-09-09 |
| DE2410982C3 (de) | 1981-11-05 |
| FR2220268B1 (enrdf_load_stackoverflow) | 1977-11-10 |
| DE2410982A1 (de) | 1974-09-26 |
| GB1458892A (en) | 1976-12-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CY1201A (en) | Substituted orthoanisamides methods of preparing them compositions containing them and their application as psychotropic agents | |
| HU182801B (en) | Process for preparing n-substituted aziridine-2-carboxylic acid derivatives | |
| EP0240180A1 (en) | 2-alkoxy-N-(1-azabicyclo[2.2.2]-oct-3-yl) benzamides and thiobenzamides in the alleviation of emesis caused by non-platinum anticancer drugs | |
| CA1037031A (en) | 8-n-methylpiperazinyl-n'-carbonyldibenzo-bicyclooctadiene and salts thereof | |
| IE46975B1 (en) | Pyrido-indole tranquilising agents | |
| US3969505A (en) | 8-N-methylpiperazinyl-N'-carbonyldibenzobicyclooctadiene and salts thereof | |
| HU181608B (en) | Process for producing imidazo-thieno-pyrimidine derivatives | |
| US3383409A (en) | Beta-(2, 6-dihalophenyl) ethylamino guanidines and the salts thereof | |
| US4006159A (en) | Substituted 1,2,4-triazole carboxamides | |
| US3880932A (en) | 4-(2-Naphthyl)-4-alkyl-3-buten-2-ones | |
| US3923996A (en) | 3-Substituted-oxindoles in compositions and methods of treating obesity | |
| US3634426A (en) | Pyrimido( 2-a)indoles and diazepino (1 12-a)indoles | |
| US3671583A (en) | Glutaric acid derivatives | |
| US5489609A (en) | 2-aminoethanesulfonic acid zinc complex compound | |
| DE2644121A1 (de) | Neue pyridobenzodiazepinone, verfahren zu ihrer herstellung und diese enthaltende arzneimittel | |
| US3772378A (en) | 7-oxo-benzocycloheptene acetic acids | |
| US3546291A (en) | Bicyclo(3.2.1)octane amines | |
| US3860652A (en) | 8-Aminoalkyl substituted dibenzobicyclo {8 3.2.1{9 {0 octadienes | |
| US3532741A (en) | Amino,monomethylamino and dimethylamino derivatives of decahydro-1,5,2,4 - ethanediylidenecyclopenta(cd) pentalene | |
| US3635971A (en) | 3 (3 4-dihydro-3-oxo-2-quinoxalinyl) propionamides | |
| US3856808A (en) | S-triazolo (4,3-d)(1,4)benzothiazepin-3(2h)-one-7,7-dioxides | |
| US3875161A (en) | Imidazo(2,1-b)quinazolin-5(1OH)-ones | |
| US3553267A (en) | 3-dimethylamino-1,2,3,4-tetrahydrofluorene | |
| US3976774A (en) | Antiemetic method | |
| US3689490A (en) | Derivatives of 2-(4-aryl-1-piperazyl)-bicyclo{8 3.3.1{9 nonan-9-ones |