CA1118446A - Racemic forms and optically active forms of 2-(4-biphenylyl)-n-(diethylamino alkyl) propionamide and salts thereof as well as processes for their production and use as spasmoltyic agents - Google Patents
Racemic forms and optically active forms of 2-(4-biphenylyl)-n-(diethylamino alkyl) propionamide and salts thereof as well as processes for their production and use as spasmoltyic agentsInfo
- Publication number
- CA1118446A CA1118446A CA000317175A CA317175A CA1118446A CA 1118446 A CA1118446 A CA 1118446A CA 000317175 A CA000317175 A CA 000317175A CA 317175 A CA317175 A CA 317175A CA 1118446 A CA1118446 A CA 1118446A
- Authority
- CA
- Canada
- Prior art keywords
- biphenyl
- propionamide
- ethyl
- diethyl
- bromide
- 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
- 229940080818 propionamide Drugs 0.000 title claims abstract description 19
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 150000003839 salts Chemical class 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims description 11
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 5
- 229940102396 methyl bromide Drugs 0.000 claims description 5
- MVFHRQWYCXYYMU-UHFFFAOYSA-N 3-(4-phenylphenyl)propanoic acid Chemical compound C1=CC(CCC(=O)O)=CC=C1C1=CC=CC=C1 MVFHRQWYCXYYMU-UHFFFAOYSA-N 0.000 claims description 4
- -1 alkyl quaternary ammonium salts Chemical class 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 claims description 2
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 7
- ASMXDHAGCXWRSL-UHFFFAOYSA-N 3-(2-phenylphenyl)propanamide Chemical class NC(=O)CCC1=CC=CC=C1C1=CC=CC=C1 ASMXDHAGCXWRSL-UHFFFAOYSA-N 0.000 claims 3
- 150000001350 alkyl halides Chemical class 0.000 claims 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims 2
- 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 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
- 239000000812 cholinergic antagonist Substances 0.000 abstract description 5
- 239000000203 mixture Substances 0.000 abstract description 5
- 150000004694 iodide salts Chemical class 0.000 abstract description 3
- 241001465754 Metazoa Species 0.000 abstract description 2
- 239000004480 active ingredient Substances 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 101150041968 CDC13 gene Proteins 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 206010012735 Diarrhoea Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010023644 Lacrimation increased Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 206010039424 Salivary hypersecretion Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- GUBNMFJOJGDCEL-UHFFFAOYSA-N dicyclomine hydrochloride Chemical compound [Cl-].C1CCCCC1C1(C(=O)OCC[NH+](CC)CC)CCCCC1 GUBNMFJOJGDCEL-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000004317 lacrimation Effects 0.000 description 2
- 210000001087 myotubule Anatomy 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- CWAFBZDOGVLICK-UHFFFAOYSA-N propanamide;hydrobromide Chemical compound Br.CCC(O)=N CWAFBZDOGVLICK-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 208000026451 salivation Diseases 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JWDYCNIAQWPBHD-UHFFFAOYSA-N 1-(2-methylphenyl)glycerol Chemical compound CC1=CC=CC=C1OCC(O)CO JWDYCNIAQWPBHD-UHFFFAOYSA-N 0.000 description 1
- JSUAJTLKVREZHV-UHFFFAOYSA-N 1-[4-(1-pyrrolidinyl)but-2-ynyl]pyrrolidine Chemical compound C1CCCN1CC#CCN1CCCC1 JSUAJTLKVREZHV-UHFFFAOYSA-N 0.000 description 1
- USQCUKQZXOWUDF-YWZLYKJASA-N 6-chloro-n-[(3s)-1-[(2s)-1-(4-methyl-5-oxo-1,4-diazepan-1-yl)-1-oxopropan-2-yl]-2-oxopyrrolidin-3-yl]naphthalene-2-sulfonamide Chemical compound O=C([C@@H](N1C([C@@H](NS(=O)(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CC1)=O)C)N1CCN(C)C(=O)CC1 USQCUKQZXOWUDF-YWZLYKJASA-N 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 206010029216 Nervousness Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- JPKKQJKQTPNWTR-KQAYXBCTSA-N [(1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2r)-3-hydroxy-2-phenylpropanoate;sulfuric acid;hydrate Chemical compound O.OS(O)(=O)=O.C1([C@H](CO)C(=O)OC2C[C@H]3CC[C@@H](C2)N3C)=CC=CC=C1.C1([C@H](CO)C(=O)OC2C[C@H]3CC[C@@H](C2)N3C)=CC=CC=C1 JPKKQJKQTPNWTR-KQAYXBCTSA-N 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000001741 anti-phlogistic effect Effects 0.000 description 1
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
- 229960004046 apomorphine Drugs 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 208000006218 bradycardia Diseases 0.000 description 1
- 230000036471 bradycardia Effects 0.000 description 1
- 230000007885 bronchoconstriction Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 1
- 229960004484 carbachol Drugs 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 230000035929 gnawing Effects 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 230000001379 nervous effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000002445 parasympatholytic effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 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
- DTYCLCKCZXMPME-UHFFFAOYSA-N propanamide hydroiodide Chemical compound CCC(N)=O.I DTYCLCKCZXMPME-UHFFFAOYSA-N 0.000 description 1
- 230000016160 smooth muscle contraction Effects 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT9643A/77 | 1977-11-30 | ||
| IT964377A IT1090782B (it) | 1977-11-30 | 1977-11-30 | 2 4 bifenilil 2 dietilamino alchil propionamide suoi sali e procedimenti di fabbricazione relativi |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1118446A true CA1118446A (en) | 1982-02-16 |
Family
ID=11132874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000317175A Expired CA1118446A (en) | 1977-11-30 | 1978-11-30 | Racemic forms and optically active forms of 2-(4-biphenylyl)-n-(diethylamino alkyl) propionamide and salts thereof as well as processes for their production and use as spasmoltyic agents |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5490157A (OSRAM) |
| BE (1) | BE872403A (OSRAM) |
| CA (1) | CA1118446A (OSRAM) |
| CH (1) | CH637370A5 (OSRAM) |
| DE (1) | DE2851416A1 (OSRAM) |
| ES (1) | ES475533A1 (OSRAM) |
| FR (1) | FR2410641A1 (OSRAM) |
| IT (1) | IT1090782B (OSRAM) |
| NL (1) | NL7811698A (OSRAM) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20012025A1 (it) * | 2001-09-28 | 2003-03-28 | Dompe Spa | Sali di ammonio quaternari di omega-amminoalchilammidi di acidi r 2-aril-propionici e composizioni farmaceutiche che li contengono |
| US20090238763A1 (en) | 2006-07-09 | 2009-09-24 | Chongxi Yu | High penetration compositions and uses thereof |
| US20090221703A1 (en) | 2006-07-09 | 2009-09-03 | Chongxi Yu | High penetration composition and uses thereof |
| PL2049482T3 (pl) * | 2006-08-08 | 2016-04-29 | Techfields Biochem Co Ltd | Dodatnio naładowane rozpuszczalne w wodzie proleki kwasów arylo- i heteroarylooctowych o bardzo dużej szybkości przenikania przez skórę |
| CN101506161B (zh) * | 2006-08-15 | 2013-11-13 | 于崇曦 | 具有快速皮肤穿透速度的带正电荷的水溶性的芳基和杂芳基丙酸类前药 |
| AU2013206218B2 (en) * | 2006-08-15 | 2016-06-30 | Techfields Biochem Co. Ltd | Positively charged water-soluble prodrugs of aryl- and heteroarylpropionic acids with very fast skin penetration rate |
| WO2008149181A1 (en) | 2007-06-04 | 2008-12-11 | Techfields Inc | Pro-drugs of nsaias with very high skin and membranes penetration rates and their new medicinal uses |
| RU2630577C2 (ru) | 2008-12-04 | 2017-09-11 | Чунси ЮЙ | Композиции интенсивного проникновения и их применение |
| JP5940036B2 (ja) * | 2013-10-08 | 2016-06-29 | テックフィールズ バイオケム カンパニー リミテッド | 非常に速い皮膚透過率を有するアリール−及びヘテロアリールプロピオン酸の正荷電水溶性プロドラッグ |
| JP6290947B2 (ja) * | 2016-02-05 | 2018-03-07 | テックフィールズ バイオケム カンパニー リミテッド | 非常に速い皮膚透過率を有するアリール−及びヘテロアリールプロピオン酸の正荷電水溶性プロドラッグ |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1584547A (OSRAM) * | 1968-06-05 | 1969-12-26 | ||
| FR1593024A (OSRAM) * | 1968-09-18 | 1970-05-25 | ||
| FR2119846A1 (en) * | 1970-12-28 | 1972-08-11 | Choay Sa | N,n-diethylaminoethylamide of para isobutyl phenylacetic - acid - antiinflammatory and analgesic |
| US4145435A (en) * | 1976-11-12 | 1979-03-20 | The Upjohn Company | 2-aminocycloaliphatic amide compounds |
-
1977
- 1977-11-30 IT IT964377A patent/IT1090782B/it active
-
1978
- 1978-11-28 CH CH1216178A patent/CH637370A5/it not_active IP Right Cessation
- 1978-11-28 DE DE19782851416 patent/DE2851416A1/de active Granted
- 1978-11-29 NL NL7811698A patent/NL7811698A/xx not_active Application Discontinuation
- 1978-11-29 ES ES475533A patent/ES475533A1/es not_active Expired
- 1978-11-30 FR FR7833889A patent/FR2410641A1/fr active Granted
- 1978-11-30 CA CA000317175A patent/CA1118446A/en not_active Expired
- 1978-11-30 BE BE192036A patent/BE872403A/xx not_active IP Right Cessation
- 1978-11-30 JP JP14730778A patent/JPS5490157A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2851416C2 (OSRAM) | 1989-02-23 |
| CH637370A5 (en) | 1983-07-29 |
| NL7811698A (nl) | 1979-06-01 |
| FR2410641B1 (OSRAM) | 1983-04-15 |
| IT1090782B (it) | 1985-06-26 |
| JPS631286B2 (OSRAM) | 1988-01-12 |
| ES475533A1 (es) | 1980-01-16 |
| FR2410641A1 (fr) | 1979-06-29 |
| DE2851416A1 (de) | 1979-05-31 |
| BE872403A (fr) | 1979-03-16 |
| JPS5490157A (en) | 1979-07-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0188248B1 (en) | Naphthalene derivatives, process for the preparation thereof and pharmaceutical composition containing same | |
| US3644636A (en) | Method of inducing bradycardia and suppressing tachycardiac effects of n-isopropyl-noradrenaline | |
| JPS61243053A (ja) | Ｎ‐（２‐アミノ脂環式族）アリールアシルアミド及びその製法 | |
| GB1565966A (en) | Aminoalkyl furan derivatives | |
| CY1446A (en) | Chemical compounds derived from cyclobutene | |
| US2862966A (en) | archo | |
| US3621043A (en) | N-substituted octadecadienoic acid amides as cholesterol lowering agents | |
| NZ202228A (en) | 2-hydroxypropylamine aryl ester derivatives and pharmaceutical compositions | |
| US3534085A (en) | 5,8-dihydronaphthloxy-aminopropanols and related compounds | |
| GB2030985A (en) | Substituted furans | |
| CA1102339A (en) | .alpha.-ARYL-.alpha.,.alpha.-BIS[.omega.-(DISUBSTITUTED AMINO)ALKYL]-ACETAMIDES AND RELATED COMPOUNDS | |
| US4242348A (en) | Novel basic substituted-alkylidenamino-oxylalkyl-carboxylic-acid esters | |
| US3506673A (en) | 2-(4'halo)-benzhydryl-3-quinuclidinols | |
| US4185124A (en) | 2-(4-Biphenylyl)-N-(2-diethylamino alkyl)propionamide and salts thereof used as spasmolytic agents | |
| CA1129875A (en) | Chromone derivatives | |
| US3522293A (en) | Selected 3-(trifluoromethylthio)propionyl compounds | |
| US3919201A (en) | 2-({62 -Aminoacryloyl)iminobenzothiazolines | |
| US3657269A (en) | Imidazo(2 1-a)isoindoles | |
| US4034011A (en) | 1,1-Diphenyl-4-(substituted-amino)butanes | |
| US3423512A (en) | Treatment of emesis in mammals with substituted methylenedioxy benzamides | |
| CA1071203A (en) | Aromatic amidines as antiviral agents in animals | |
| FR2525221A1 (fr) | Derives du furanne et sels d'addition de ces derives, leurs procedes de preparation et leurs applications en therapeutique | |
| US3148188A (en) | Benzothiazine derivatives | |
| US2855401A (en) | Certain n-(aminophenoxy pentyl) sulfonamide or saccharine compounds and higher homologues | |
| SU805607A1 (ru) | N-(1-адамантил)-3-аминопропионитрил гидрохлорид,обладающий антивирусной активностью,и способ его получени |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |