IE39541B1 - Primary amino acylanilides methods of making the same and use as anti-arrhythmic drugs - Google Patents
Primary amino acylanilides methods of making the same and use as anti-arrhythmic drugsInfo
- Publication number
- IE39541B1 IE39541B1 IE28/74A IE2874A IE39541B1 IE 39541 B1 IE39541 B1 IE 39541B1 IE 28/74 A IE28/74 A IE 28/74A IE 2874 A IE2874 A IE 2874A IE 39541 B1 IE39541 B1 IE 39541B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- reaction
- bromo
- prepared
- methyl
- Prior art date
Links
- 239000003416 antiarrhythmic agent Substances 0.000 title abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 10
- 150000001875 compounds Chemical class 0.000 abstract 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 6
- 229910021529 ammonia Inorganic materials 0.000 abstract 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 2
- ILLHORFDXDLILE-UHFFFAOYSA-N 2-bromopropanoyl bromide Chemical compound CC(Br)C(Br)=O ILLHORFDXDLILE-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000002346 iodo group Chemical group I* 0.000 abstract 2
- NLGKRVNANIZGNI-UHFFFAOYSA-N n,2,6-trimethylaniline Chemical compound CNC1=C(C)C=CC=C1C NLGKRVNANIZGNI-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- DITMPRUKGMJSKB-UHFFFAOYSA-N (4-butoxy-2,6-dimethylphenyl)-phenyldiazene Chemical compound CC1=CC(OCCCC)=CC(C)=C1N=NC1=CC=CC=C1 DITMPRUKGMJSKB-UHFFFAOYSA-N 0.000 abstract 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 abstract 1
- FHMPFSKGDPKPDJ-UHFFFAOYSA-N 2,3,6-trimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1C FHMPFSKGDPKPDJ-UHFFFAOYSA-N 0.000 abstract 1
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical group CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 abstract 1
- UWRBGVSJALGSLY-UHFFFAOYSA-N 2-bromo-n-(2,6-dimethylphenyl)-n-ethylpropanamide Chemical compound CC(Br)C(=O)N(CC)C1=C(C)C=CC=C1C UWRBGVSJALGSLY-UHFFFAOYSA-N 0.000 abstract 1
- FBDCSPTZEYWAQE-UHFFFAOYSA-N 2-bromo-n-(2,6-dimethylphenyl)-n-methylpropanamide Chemical compound CC(Br)C(=O)N(C)C1=C(C)C=CC=C1C FBDCSPTZEYWAQE-UHFFFAOYSA-N 0.000 abstract 1
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 abstract 1
- JJVKJJNCIILLRP-UHFFFAOYSA-N 2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1N JJVKJJNCIILLRP-UHFFFAOYSA-N 0.000 abstract 1
- IHBVNSPHKMCPST-UHFFFAOYSA-N 3-bromopropanoyl chloride Chemical compound ClC(=O)CCBr IHBVNSPHKMCPST-UHFFFAOYSA-N 0.000 abstract 1
- KIHUWAOTZVYMFH-UHFFFAOYSA-N 4-butoxy-2,6-dimethylaniline Chemical compound CCCCOC1=CC(C)=C(N)C(C)=C1 KIHUWAOTZVYMFH-UHFFFAOYSA-N 0.000 abstract 1
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 abstract 1
- XZJZXPFFLHBNGJ-UHFFFAOYSA-N Cc1cc(O)cc(C)c1N=Nc1ccccc1 Chemical compound Cc1cc(O)cc(C)c1N=Nc1ccccc1 XZJZXPFFLHBNGJ-UHFFFAOYSA-N 0.000 abstract 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 abstract 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 1
- -1 N-substituted phthalimide Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000006317 isomerization reaction Methods 0.000 abstract 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 abstract 1
- WPXNHSRXGYBXNL-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NC1=C(C)C=CC=C1C WPXNHSRXGYBXNL-UHFFFAOYSA-N 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 229940127557 pharmaceutical product Drugs 0.000 abstract 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B27/00—Preparations in which the azo group is formed in any way other than by diazotising and coupling, e.g. oxidation
-
- 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
- A61P9/06—Antiarrhythmics
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32159073A | 1973-01-08 | 1973-01-08 | |
| US32180073A | 1973-01-08 | 1973-01-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE39541L IE39541L (en) | 1974-07-08 |
| IE39541B1 true IE39541B1 (en) | 1978-11-08 |
Family
ID=26983031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE28/74A IE39541B1 (en) | 1973-01-08 | 1974-01-07 | Primary amino acylanilides methods of making the same and use as anti-arrhythmic drugs |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5833221B2 (de) |
| AR (2) | AR205617A1 (de) |
| CA (1) | CA1024528A (de) |
| CH (2) | CH603556A5 (de) |
| DD (1) | DD113749A5 (de) |
| DE (1) | DE2400540A1 (de) |
| ES (1) | ES422085A1 (de) |
| FR (1) | FR2213065B1 (de) |
| GB (1) | GB1461602A (de) |
| HU (1) | HU166667B (de) |
| IE (1) | IE39541B1 (de) |
| NL (1) | NL7400167A (de) |
| SU (2) | SU563119A3 (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4098895A (en) * | 1975-09-30 | 1978-07-04 | Ciba-Geigy Corporation | Triazolylacetanilide compounds and microbicidal compositions |
| GB2267709A (en) * | 1992-06-11 | 1993-12-15 | Merck & Co Inc | Novel process for the preparation of alpha-aminoacylanilides |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB705460A (en) * | 1951-02-26 | 1954-03-10 | Astra Apotekarnes Kem Fab | Process for the preparation of aminoacetyl-anilides having alkyl substituents at theamino nitrogen and products thereof |
| DE939207C (de) * | 1952-02-25 | 1956-02-16 | Cilag Ag | Verfahren zur Herstellung von als Lokalanaesthetica verwendbaren basisch substituierten Fettsaeure-(2-chlor-6-methyl-aniliden) und ihren Salzen |
| DE1046059B (de) * | 1952-06-12 | 1958-12-11 | Astra Ab | Verfahren zur Herstellung von als lokalanaesthetische Mittel verwendbaren N-Alkyl-alaninaniliden |
| US2912460A (en) * | 1952-08-18 | 1959-11-10 | Hoechst Ag | Basically substituted carboxylic acid amides and a process of preparing them |
| FR1167026A (fr) * | 1953-08-21 | 1958-11-19 | Hoechst Ag | Amides d'acides à substituant basique et procédé de préparation de ces amides d'acides |
| DE1001277B (de) * | 1953-11-10 | 1957-01-24 | Leo Pharm Prod Ltd | Verfahren zur Herstellung von lokalanaesthetisch wirksamen Dialkylaminoacylaniliden |
| CH318077A (de) * | 1954-01-29 | 1956-12-15 | Cilag Ag | Verfahren zur Herstellung von B-Amino-buttersäureaniliden |
| DE1055541B (de) * | 1954-11-01 | 1959-04-23 | Geistlich Soehne Ag | Verfahren zur Herstellung von beta-Dialkylaminoacylaniliden |
| DE1028099B (de) * | 1955-06-11 | 1958-04-17 | Goesta Lennart Flemmert Dr Tec | Verfahren zur Herstellung von amorphem, feinverteiltem Siliciumdioxyd |
| DE1170856B (de) * | 1960-10-11 | 1964-05-21 | Degussa | Verfahren zur Herstellung von festhaftenden und loetfaehigen Metallschichten, insbesondere Silberschichten, auf keramischem Material, insbesondere Aluminiumoxydkoerpern |
| GB1028099A (en) | 1965-03-30 | 1966-05-04 | Tanabe Seiyaku Co | Substituted propionanilides |
| CH449042A (de) * | 1965-04-02 | 1967-12-31 | Tanabe Seiyaku Co | Verfahren zur Herstellung substituierter Propionanilide |
| SE337810B (de) | 1966-05-13 | 1971-08-23 | Tanabe Seiyaku Co |
-
1974
- 1974-01-01 AR AR251845A patent/AR205617A1/es active
- 1974-01-04 SU SU1982938A patent/SU563119A3/ru active
- 1974-01-07 NL NL7400167A patent/NL7400167A/xx not_active Application Discontinuation
- 1974-01-07 IE IE28/74A patent/IE39541B1/xx unknown
- 1974-01-07 FR FR7400485A patent/FR2213065B1/fr not_active Expired
- 1974-01-07 DE DE2400540A patent/DE2400540A1/de not_active Ceased
- 1974-01-07 GB GB57074A patent/GB1461602A/en not_active Expired
- 1974-01-07 HU HUAA763A patent/HU166667B/hu unknown
- 1974-01-07 CH CH1010277A patent/CH603556A5/xx not_active IP Right Cessation
- 1974-01-07 CA CA189,559A patent/CA1024528A/en not_active Expired
- 1974-01-07 DD DD175865A patent/DD113749A5/xx unknown
- 1974-01-07 JP JP49005015A patent/JPS5833221B2/ja not_active Expired
- 1974-01-07 ES ES422085A patent/ES422085A1/es not_active Expired
- 1974-01-07 CH CH14174A patent/CH596148A5/xx not_active IP Right Cessation
-
1975
- 1975-03-24 SU SU752116825A patent/SU656504A3/ru active
- 1975-09-26 AR AR260567A patent/AR211695A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5833221B2 (ja) | 1983-07-18 |
| CH603556A5 (de) | 1978-08-31 |
| GB1461602A (en) | 1977-01-13 |
| SU656504A3 (ru) | 1979-04-05 |
| FR2213065A1 (de) | 1974-08-02 |
| CH596148A5 (de) | 1978-02-28 |
| JPS49116034A (de) | 1974-11-06 |
| AR205617A1 (es) | 1976-05-21 |
| FR2213065B1 (de) | 1978-01-06 |
| NL7400167A (de) | 1974-07-10 |
| HU166667B (de) | 1975-05-28 |
| DD113749A5 (de) | 1975-06-20 |
| ES422085A1 (es) | 1977-01-01 |
| AR211695A1 (es) | 1978-02-28 |
| CA1024528A (en) | 1978-01-17 |
| DE2400540A1 (de) | 1974-08-15 |
| AU6424774A (en) | 1975-07-10 |
| IE39541L (en) | 1974-07-08 |
| SU563119A3 (ru) | 1977-06-25 |
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