IE39166L - N-substituted acetamide pharmaceuticals. - Google Patents
N-substituted acetamide pharmaceuticals.Info
- Publication number
- IE39166L IE39166L IE740542A IE54274A IE39166L IE 39166 L IE39166 L IE 39166L IE 740542 A IE740542 A IE 740542A IE 54274 A IE54274 A IE 54274A IE 39166 L IE39166 L IE 39166L
- Authority
- IE
- Ireland
- Prior art keywords
- alkyl
- acid
- compounds
- prepared
- formula
- Prior art date
Links
- -1 N-substituted acetamide Chemical class 0.000 title 1
- 239000003814 drug Substances 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 9
- 150000001875 compounds Chemical class 0.000 abstract 5
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 abstract 2
- 150000003869 acetamides Chemical class 0.000 abstract 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 2
- 239000012346 acetyl chloride Substances 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- VJDWLGLJZNWMFB-UHFFFAOYSA-N 2,2-dicyclopropylacetaldehyde Chemical compound C1CC1C(C=O)C1CC1 VJDWLGLJZNWMFB-UHFFFAOYSA-N 0.000 abstract 1
- LAPHTVCKEMNVML-UHFFFAOYSA-N 2,2-dicyclopropylacetic acid Chemical compound C1CC1C(C(=O)O)C1CC1 LAPHTVCKEMNVML-UHFFFAOYSA-N 0.000 abstract 1
- JKOQJAQBOWTQAJ-UHFFFAOYSA-N 2,2-dicyclopropylacetyl chloride Chemical compound C1(CC1)C(C(=O)Cl)C1CC1 JKOQJAQBOWTQAJ-UHFFFAOYSA-N 0.000 abstract 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical class CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 230000002744 anti-aggregatory effect Effects 0.000 abstract 1
- 230000003276 anti-hypertensive effect Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 230000001778 cardiodepressive effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- LFAGQMCIGQNPJG-UHFFFAOYSA-N silver cyanide Chemical compound [Ag+].N#[C-] LFAGQMCIGQNPJG-UHFFFAOYSA-N 0.000 abstract 1
- 229940098221 silver cyanide Drugs 0.000 abstract 1
- 230000000304 vasodilatating effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/38—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
1436593 Substituted acetamides SCIENCE UNION ET CIE SOC FRANCAISE DE REMEDICALE 15 March 1974 [15 March 1973] 12430/73 Heading C2C Novel substituted acetamides of the Formula I in which R 1 is H or C 1 -C 6 alkyl; R 2 and R 3 each are C 1 -C 6 alkyl, cycloalkyl or aryl; R 6 is H or C 1 -C 6 alkyl; R 4 is H, C 1 -C 6 alkyl, C 2 -C 10 alkenyl or benzyl; R 5 is C 1 -C 6 alkyl, C 2 -C 10 alkenyl, C 2 -C 6 alkynyl or aryl-C 1 -C 4 alkyl; or R 4 and R 5 together with the nitrogen atom to which they are attached form a 5 to 8 membered saturated heterocyclic ring which is optionally substituted and may contain a further hetereo atom, and R<SP>1</SP> is H or acyl, and the acid addition salts thereof are prepared by reaction carboxylic acids of the formula or reactive functional derivatives thereof with amines of the formula compounds of the Formula I above in which R 4 is H may also be obtained by the hydrogenolysis or acid hydrolysis of the corresponding compounds in which R 4 is benzyl, and those in which R<SP>1</SP> is acyl by acylating the corresponding compounds in which R<SP>1</SP> is H. (2,2<SP>1</SP>,6,6<SP>1</SP> - Tetramethyldiphenyl)acetyl chloride is prepared by reacting thionyl chloride with the acid, resulting from the hydrolysis of the corresponding nitrile, which is made by reacting silver cyanide with (2,21,6,61-tetramethyldiphenyl)chloromethane. Similarly the following are prepared: (4,41 - difluorodiphenyl)acetyl chloride, (4,4<SP>1</SP> - difluorodiphenyl)acetic acid, and (4,4<SP>1</SP>-difluorodiphenyl)acetonitrile. Dicyclopropylacetyl chloride is prepared by reacting thionyl chloride with dicyclopropylacetic acid, obtained by oxidizing dicyclopropylacetaldehyde. (2,2<SP>1</SP>,3-Trimethoxy-5<SP>1</SP>-methyldiphenyl)acetic acid and (2-methoxy-2<SP>1</SP>-methylthio- 5<SP>1</SP>-methyldiphenyl)acetic acid are also obtained by oxidating the corresponding acetaldehydes. Pharmaceutical compositions, suitable for oral, parenteral, sublingual or rectal administration, contain the above compounds or non- toxic acid addition salts thereof in admixture or conjunction with pharmaceutical carriers. The compounds anti-arhythmic, cardio-depressive, vasodilatory, anti-hypertensive and anti-aggregating properties.
[GB1436593A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1243073A GB1436593A (en) | 1973-03-15 | 1973-03-15 | N-substituted acetamides processes for their preparation and pharmaceutical compositions containing them apparatus for processing photograp |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE39166L true IE39166L (en) | 1974-09-15 |
| IE39166B1 IE39166B1 (en) | 1978-08-16 |
Family
ID=10004460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE542/74A IE39166B1 (en) | 1973-03-15 | 1974-03-14 | N-substituted acetamides processes for their preparation and pharmaceutical compositions containing them |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS537406B2 (en) |
| AR (1) | AR213712A1 (en) |
| AT (1) | AT336579B (en) |
| AU (1) | AU503812B2 (en) |
| BE (1) | BE812339A (en) |
| CA (1) | CA1052788A (en) |
| CH (1) | CH583688A5 (en) |
| DE (1) | DE2411885A1 (en) |
| ES (1) | ES424238A1 (en) |
| FR (1) | FR2221144B1 (en) |
| GB (1) | GB1436593A (en) |
| HU (1) | HU168559B (en) |
| IE (1) | IE39166B1 (en) |
| NL (1) | NL154496B (en) |
| SU (1) | SU625600A3 (en) |
| ZA (1) | ZA741711B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2720915C2 (en) * | 1977-05-10 | 1986-04-17 | Kali-Chemie Pharma Gmbh, 3000 Hannover | N? 1? -Acyl-2-hydroxy-1,3-diaminopropanes and drugs containing these compounds as an active ingredient |
| ES469020A1 (en) * | 1977-05-10 | 1979-09-01 | Kali Chemie Pharma Gmbh | N1-acyl-N2-phenyldiaminopropanols and pharmaceutical compositions thereof |
| EP1640359A3 (en) * | 1997-12-10 | 2006-04-05 | Nps Pharmaceuticals, Inc. | Anticonvulsant and central nervous system-active bis(fluorophenyl)alkylamides |
| WO2004094793A1 (en) | 2003-04-24 | 2004-11-04 | Byd Company Limited | Muffler and catalytic converter devices |
-
1973
- 1973-03-15 GB GB1243073A patent/GB1436593A/en not_active Expired
-
1974
- 1974-03-08 CH CH332974A patent/CH583688A5/xx not_active IP Right Cessation
- 1974-03-08 AU AU66458/74A patent/AU503812B2/en not_active Expired
- 1974-03-11 AR AR252719A patent/AR213712A1/en active
- 1974-03-12 DE DE2411885A patent/DE2411885A1/en not_active Withdrawn
- 1974-03-12 HU HUSI1384A patent/HU168559B/hu unknown
- 1974-03-13 ES ES424238A patent/ES424238A1/en not_active Expired
- 1974-03-13 CA CA194,875A patent/CA1052788A/en not_active Expired
- 1974-03-14 JP JP2957974A patent/JPS537406B2/ja not_active Expired
- 1974-03-14 BE BE142041A patent/BE812339A/en unknown
- 1974-03-14 FR FR7408610A patent/FR2221144B1/fr not_active Expired
- 1974-03-14 IE IE542/74A patent/IE39166B1/en unknown
- 1974-03-14 SU SU742005426A patent/SU625600A3/en active
- 1974-03-15 ZA ZA00741711A patent/ZA741711B/en unknown
- 1974-03-15 NL NL747403543A patent/NL154496B/en unknown
- 1974-03-15 AT AT217874A patent/AT336579B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HU168559B (en) | 1976-05-28 |
| FR2221144B1 (en) | 1978-07-21 |
| AT336579B (en) | 1977-05-10 |
| JPS49134619A (en) | 1974-12-25 |
| ES424238A1 (en) | 1976-05-16 |
| NL7403543A (en) | 1974-09-17 |
| AR213712A1 (en) | 1979-03-15 |
| ATA217874A (en) | 1976-09-15 |
| AU503812B2 (en) | 1979-09-20 |
| CH583688A5 (en) | 1977-01-14 |
| SU625600A3 (en) | 1978-09-25 |
| ZA741711B (en) | 1975-04-30 |
| AU6645874A (en) | 1975-09-11 |
| FR2221144A1 (en) | 1974-10-11 |
| IE39166B1 (en) | 1978-08-16 |
| JPS537406B2 (en) | 1978-03-17 |
| NL154496B (en) | 1977-09-15 |
| GB1436593A (en) | 1976-05-19 |
| BE812339A (en) | 1974-09-16 |
| CA1052788A (en) | 1979-04-17 |
| DE2411885A1 (en) | 1974-09-26 |
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