CA1086320A - Heterocyclic compounds - Google Patents
Heterocyclic compoundsInfo
- Publication number
- CA1086320A CA1086320A CA324,130A CA324130A CA1086320A CA 1086320 A CA1086320 A CA 1086320A CA 324130 A CA324130 A CA 324130A CA 1086320 A CA1086320 A CA 1086320A
- Authority
- CA
- Canada
- Prior art keywords
- chain
- group
- carbon atoms
- lower alkyl
- dimethoxy
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (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)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
This invention relates to a process for the production of a compound of the general formula (I) wherein R represents a group of the formula or (a) (b) in which R1, R2 and R3 each represent a hydrogen or halogen atom or a lower alkyl, lower alkoxy, aryl-(lower alkoxy), aryloxy, phenyl, nitro, trifluoro-methyl, hydroxy, cyano, di(lower alkyl)amino or lower alkanoyloxy group or two adjacent R1, R2 and R3 symbols together represent a methylenedioxy, ethylenedioxy or butadien-1,3-ylene-1,4 group, R4 represents a hydrogen atom or a lower alkyl group, R5, R6 and R7 each rcpresent a hydrogen or halogen atom or a lower alkyl, lower alkoxy, hydroxy or benzyloxy group or two ad-jacent R5, R6 and R7 symbols together represent a methylenedioxy or ethylene-dioxy group, Y represents a straight-chain or branched-chain, optionally hydroxy-substituted, aliphatic group containing 3 - 8 carbon atoms, of which 3 - 5 carbon atoms are present in the chain, and Z reprosents a straight-chain or branched-chain, optionally hydroxy-substituted aliphatic group containing 1 - 8 carbon atoms, of which 1 - 4 carbon atoms are present in the chain, and ? stands for zero or 1, or an acid addition salt thoreof, which comprises reacting a compound of the general formula (II) wherein R and Y have tbe same meanings as given above with a compound of the general formula
This invention relates to a process for the production of a compound of the general formula (I) wherein R represents a group of the formula or (a) (b) in which R1, R2 and R3 each represent a hydrogen or halogen atom or a lower alkyl, lower alkoxy, aryl-(lower alkoxy), aryloxy, phenyl, nitro, trifluoro-methyl, hydroxy, cyano, di(lower alkyl)amino or lower alkanoyloxy group or two adjacent R1, R2 and R3 symbols together represent a methylenedioxy, ethylenedioxy or butadien-1,3-ylene-1,4 group, R4 represents a hydrogen atom or a lower alkyl group, R5, R6 and R7 each rcpresent a hydrogen or halogen atom or a lower alkyl, lower alkoxy, hydroxy or benzyloxy group or two ad-jacent R5, R6 and R7 symbols together represent a methylenedioxy or ethylene-dioxy group, Y represents a straight-chain or branched-chain, optionally hydroxy-substituted, aliphatic group containing 3 - 8 carbon atoms, of which 3 - 5 carbon atoms are present in the chain, and Z reprosents a straight-chain or branched-chain, optionally hydroxy-substituted aliphatic group containing 1 - 8 carbon atoms, of which 1 - 4 carbon atoms are present in the chain, and ? stands for zero or 1, or an acid addition salt thoreof, which comprises reacting a compound of the general formula (II) wherein R and Y have tbe same meanings as given above with a compound of the general formula
Description
8~3ZO
This application is a divisional of our copending Canadian Patent Application Serial No. 216,313 filed December 18, 1974.
The present invention relates to sulphur-containing compounds.
According to the present invention there are provided compounds of the general formula O R4 ~ R5 R - C - Y - N ~ (Z)m ~ R6 (I) wherein R represents a group of the formula ,~ R
or (a) (b) in which Rl, R2 and R3 each represent a hydrogen or halogen atom or a lower alkyl, lower alkoxy, aryl-(lower alkoxy), aryloxy, phenyl, nitro, trifluoro-methyl, hydroxy, cyano, di(lower alkyl)amino or lower alkanoyloxy group or two adjacent Rl, R2 and R3 symbols together represent a methylenedioxy, ethyl-enedioxy or butadien-1,3-ylene-1,4 group, R4 represents a hydrogen atom or a lower alkyl group, R5, R6 and R7 each represent a hydrogen or halogen atom or a lower alkyl, lower alkoxy, hydroxy or benzyloxy group or two adjacent R5, R6 and R7 symbols together represent a methylenedioxy or ethylenedioxy group, Y represents a straight-chain or branched-chain, optionally hydroxy-substituted, aliphatic : :~ : . ::: .:: : :: : ~ ." . ;
- : - , :: . :: : .: ::: ~ ." . : , :. ::
108~:}20 group containing ~ - 8 carbon atoms, of which ~ - ~ carbon atoms are present B in the chain, and Z represents a straight-chain or branched-chain, optionally hydroxy-substituted aliphatic group containing 1 - 8 carbon atoms, of which 1 - 4 carbon atoms are present in the chain, and _ stands for zero or 1, and acid addition salts thereof.
The compounds of the present invention are precursors in the produc-tion of sulphur-containing compounds claimed in our copending Canadian Patent Application Serial No. 216313 filed December 18, 1974, which possess coronary-dilating properties.
As used in this description and in the accompanying claims, the term "lower alkyl" means straight-chain or branched-chain alkyl groups containing 1 - 6 carbon atoms (e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert.butyl, amyl, and hexyl). The term "lower alkoxy" means lower alkyl ether groups in which the "lower alkyl" moiety has the aforementioned significance.
The term "halogen" means fluorine, chlorine, bromine and iodine. The term ; "lower alkanoyl" means alkanoyl groups containing up to 6 carbon atoms (e.g.
formyl, acetyl, propionyl, and butyryl). The term "aryl" means unsubstituted or substituted phenyl, the substituent~s) being selected from halogen, lower alkyl, lower alkoxy, nitro and amino.
This invention also relates to a process in which the compounds of formula ~I) are prepared by reacting a compound of the general formula O
R-C-Y-Cl (II) wherein R and Y have the significance given earlier, with a compound of the general formula R4 ~ R6 ~III) . :, . ~. . : .
; . :: :
i320 wherein R4 - R7, Z and m have the significance given earlier, and where required, converting the resulting compound into an acid addition salt.
The reaction is expediently carried out in the presence of an acid-binding agent such as a tertiary amine (e.g. N-ethyl-N,N-diisopropylamine) which simultaneously serves as the solvent. The reaction is also expediently carried out at an elevated temperature, preferably at a temperature up to about 130C, depending on the boiling point of the solvent.
Example S00 g of polyphosphonic acid and 69 g of veratrol are added to a 1 litre round-bottomed flask, to this are added 61 g of 4-chlorobutyric acid in one portion, the temperature rising steadily to 55C. After 1 hour, the entire mixture is poured on to ice. The mixture is then extracted with a mixture of ether/methylene chloride (3:1). The organic extracts are extracted with water, then with a saturated sodium bicarbonate solution and finally again with water, dried over magnesium sulphate and evaporated in vacuo. The residual crystal mass is recrystallised from ether. There are obtained 62.9 g of 3,4-dimethoxy-~-chlorobutyrophenone of melting point 91-92C.
12 g of 3,4-dimethoxy-~-chlorobutyrophenone are treated with 40 ml of N-ethyl-N,N-diisopropylamine and 9 g of N-methyl-homoveratrylamine and stirred at 120C for 6 hours. After evaporation of the solvent in vacuo, the viscous mass is treated with ether and sodium hydroxide. The organic extracts are washed with water and extracted with l-N hydrochloric acid. The acidic extracts are then made alkaline and extracted with ether. The ether extracts are combined, dried over sodium sulphate and evaporated. The thus-obtained 3',4'-dimethoxy-4-(methylveratrylamino)-butyrophenone is pure according to thin-layer chromatography.
The following compounds can be manufactured in a manner analogous to that described in this Example:
5-1(3,4-dimethoxyphenethyl)-methylamino~-3',4'-dimethoxyvalero-1~6320 phenone (melting point of the hydrochloride 165 - 166C), obtained from 3,4-dimethoxy-~-chlorovalerophenone and N-methyl-homoveratrylamine.
6-/(3,4-dimethoxyphenetyl)-methylamino/-3',4'-dimethoxyhexanophenone ~melting point of the hydrochloride 128 - 129C), obtained from 6-chloro-3', 4'-dimethoxyhexanophenone and N-methyl-homoveratrylamine.
3',4'-dimethoxy-4-/ / (3,4-dimethoxyphenyl)-propyl/-methylamino/-butyrophenone, obtained from 3,4-dimethoxy-y-chlorobutyrophenone and 3-(3,4-dimethoxyphenyl)-N-methylpropylamine.
4-/ (3,4-dimethoxy-a-methylphenethyl)-methylamino/-3',4'-dimethoxy-butyrophenone, obtained from 3,4-dimethoxy-~-chlorobutyrophenone and N,a-dimethyl-~-phenylethylamine (boiling point 130 - 140C/20 mm Hg); and g 4-/ ~3,4-dimethoxyphenethyl) methylamino/-3',4'-dimethoxybutyrophenone.
This application is a divisional of our copending Canadian Patent Application Serial No. 216,313 filed December 18, 1974.
The present invention relates to sulphur-containing compounds.
According to the present invention there are provided compounds of the general formula O R4 ~ R5 R - C - Y - N ~ (Z)m ~ R6 (I) wherein R represents a group of the formula ,~ R
or (a) (b) in which Rl, R2 and R3 each represent a hydrogen or halogen atom or a lower alkyl, lower alkoxy, aryl-(lower alkoxy), aryloxy, phenyl, nitro, trifluoro-methyl, hydroxy, cyano, di(lower alkyl)amino or lower alkanoyloxy group or two adjacent Rl, R2 and R3 symbols together represent a methylenedioxy, ethyl-enedioxy or butadien-1,3-ylene-1,4 group, R4 represents a hydrogen atom or a lower alkyl group, R5, R6 and R7 each represent a hydrogen or halogen atom or a lower alkyl, lower alkoxy, hydroxy or benzyloxy group or two adjacent R5, R6 and R7 symbols together represent a methylenedioxy or ethylenedioxy group, Y represents a straight-chain or branched-chain, optionally hydroxy-substituted, aliphatic : :~ : . ::: .:: : :: : ~ ." . ;
- : - , :: . :: : .: ::: ~ ." . : , :. ::
108~:}20 group containing ~ - 8 carbon atoms, of which ~ - ~ carbon atoms are present B in the chain, and Z represents a straight-chain or branched-chain, optionally hydroxy-substituted aliphatic group containing 1 - 8 carbon atoms, of which 1 - 4 carbon atoms are present in the chain, and _ stands for zero or 1, and acid addition salts thereof.
The compounds of the present invention are precursors in the produc-tion of sulphur-containing compounds claimed in our copending Canadian Patent Application Serial No. 216313 filed December 18, 1974, which possess coronary-dilating properties.
As used in this description and in the accompanying claims, the term "lower alkyl" means straight-chain or branched-chain alkyl groups containing 1 - 6 carbon atoms (e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert.butyl, amyl, and hexyl). The term "lower alkoxy" means lower alkyl ether groups in which the "lower alkyl" moiety has the aforementioned significance.
The term "halogen" means fluorine, chlorine, bromine and iodine. The term ; "lower alkanoyl" means alkanoyl groups containing up to 6 carbon atoms (e.g.
formyl, acetyl, propionyl, and butyryl). The term "aryl" means unsubstituted or substituted phenyl, the substituent~s) being selected from halogen, lower alkyl, lower alkoxy, nitro and amino.
This invention also relates to a process in which the compounds of formula ~I) are prepared by reacting a compound of the general formula O
R-C-Y-Cl (II) wherein R and Y have the significance given earlier, with a compound of the general formula R4 ~ R6 ~III) . :, . ~. . : .
; . :: :
i320 wherein R4 - R7, Z and m have the significance given earlier, and where required, converting the resulting compound into an acid addition salt.
The reaction is expediently carried out in the presence of an acid-binding agent such as a tertiary amine (e.g. N-ethyl-N,N-diisopropylamine) which simultaneously serves as the solvent. The reaction is also expediently carried out at an elevated temperature, preferably at a temperature up to about 130C, depending on the boiling point of the solvent.
Example S00 g of polyphosphonic acid and 69 g of veratrol are added to a 1 litre round-bottomed flask, to this are added 61 g of 4-chlorobutyric acid in one portion, the temperature rising steadily to 55C. After 1 hour, the entire mixture is poured on to ice. The mixture is then extracted with a mixture of ether/methylene chloride (3:1). The organic extracts are extracted with water, then with a saturated sodium bicarbonate solution and finally again with water, dried over magnesium sulphate and evaporated in vacuo. The residual crystal mass is recrystallised from ether. There are obtained 62.9 g of 3,4-dimethoxy-~-chlorobutyrophenone of melting point 91-92C.
12 g of 3,4-dimethoxy-~-chlorobutyrophenone are treated with 40 ml of N-ethyl-N,N-diisopropylamine and 9 g of N-methyl-homoveratrylamine and stirred at 120C for 6 hours. After evaporation of the solvent in vacuo, the viscous mass is treated with ether and sodium hydroxide. The organic extracts are washed with water and extracted with l-N hydrochloric acid. The acidic extracts are then made alkaline and extracted with ether. The ether extracts are combined, dried over sodium sulphate and evaporated. The thus-obtained 3',4'-dimethoxy-4-(methylveratrylamino)-butyrophenone is pure according to thin-layer chromatography.
The following compounds can be manufactured in a manner analogous to that described in this Example:
5-1(3,4-dimethoxyphenethyl)-methylamino~-3',4'-dimethoxyvalero-1~6320 phenone (melting point of the hydrochloride 165 - 166C), obtained from 3,4-dimethoxy-~-chlorovalerophenone and N-methyl-homoveratrylamine.
6-/(3,4-dimethoxyphenetyl)-methylamino/-3',4'-dimethoxyhexanophenone ~melting point of the hydrochloride 128 - 129C), obtained from 6-chloro-3', 4'-dimethoxyhexanophenone and N-methyl-homoveratrylamine.
3',4'-dimethoxy-4-/ / (3,4-dimethoxyphenyl)-propyl/-methylamino/-butyrophenone, obtained from 3,4-dimethoxy-y-chlorobutyrophenone and 3-(3,4-dimethoxyphenyl)-N-methylpropylamine.
4-/ (3,4-dimethoxy-a-methylphenethyl)-methylamino/-3',4'-dimethoxy-butyrophenone, obtained from 3,4-dimethoxy-~-chlorobutyrophenone and N,a-dimethyl-~-phenylethylamine (boiling point 130 - 140C/20 mm Hg); and g 4-/ ~3,4-dimethoxyphenethyl) methylamino/-3',4'-dimethoxybutyrophenone.
Claims (7)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A process for the production of a compound of the general formula (I) wherein R represents a group of the formula or (a) (b) in which R1, R2 and R3 each represent a hydrogen or halogen atom or a lower alkyl, lower alkoxy, aryl-(lower alkoxy), aryloxy, phenyl, nitro, trifluoro-methyl, hydroxy, cyano, di(lower alkyl)amino or lower alkanoyloxy group or two adjacent R1, R2 and R3 symbols together represent a methylenedioxy, ethyl-enedioxy or butadien-1,3-ylene-1,4 group, R4 represents a hydrogen atom or a lower alkyl group, R5, R6 and R7 each represent a hydrogen or halogen atom or a lower alkyl, lower alkoxy, hydroxy or benzyloxy group or two adjacent R5, R6 and R7 symbols together represent a methylenedioxy or ethylenedioxy group, Y repre-sents a straight-chain or branched-chain, optionally hydroxy-substituted, ali-phatic group containing 3 - 8 carbon atoms, of which 3 - 5 carbon atoms are present in the chain, and Z represents a straight-chain or branched-chain, optionally hydroxy-substituted aliphatic group containing 1 - 8 carbon atoms, of which 1 - 4 carbon atoms are present in the chain, and ? stands for zero or 1, or an acid addition salt thereof, which comprises reacting a compound of the general formula (II) wherein R and Y have the same meanings as given above with a compound of the general formula (III) wherein R4, R5, R6, R7, Z and ? have the same meanings as given above, and where required, converting the resulting compound into an acid addition salt.
2. A compound of the general formula (I) wherein R represents a group of the formula or (a) (b) in which R1, R2 and R3 each represent a hydrogen or halogen atom or a lower alkyl, lower alkoxy, aryl-(lower alkoxy), aryloxy, phenyl, nitro, trifluoro-methyl, hydroxy, cyano, di(lower alkyl)amino or lower alkanoyloxy group or two adjacent R1, R2 and R3 symbols together represent a methylenedioxy, ethyl-enedioxy or butadien-1,3-ylene-1,4 group, R4 represents a hydrogen atom or a lower alkyl group, R5, R6 and R7 each represent a hydrogen or halogen atom or a lower alkyl, lower alkoxy, hydroxy or benzyloxy group or two adjacent R5, R6 and R7 symbols together represent a methylenedioxy or ethylenedioxy group, Y represents a straight-chain or branched-chain, optionally hydroxy-substi-tuted, aliphatic group containing 3 - 8 carbon atoms, of which 3 - 5 carbon atoms are present in the chain, and Z represents a straight-chain or branched-chain, optionally hydroxy-substituted aliphatic group containing 1 - 8 carbon atoms, of which 1 - 4 carbon atoms are present in the chain, and m stands for zero or 1, or an acid addition salt thereof, whenever prepared by the process of claim 1 or by an obvious chemical equivalent thereof.
3. A process for the preparation of 3',4'-dimethoxy-4-(methylveratryl-amino)butyrophenone which comprises reacting 3,4-dimethoxy-.gamma.-chlorobutyro-phenone with N-methyl-homoveratrylamine.
4. A process for the preparation of 5-[(3,4-dimethoxyphenethyl)methyl-amino]-3',4'-dimethoxyvalerophenone and its hydrochloride which comprises re-acting 3,4-dimethoxy-.delta.-chlorovalerophenone with N-methylhomoveratrylamine and when the hydrochloride is required reacting the base so obtained with hydrogen chloride.
5. A process for the preparation of 6-[(3,4-dimethoxyphenethyl)methyl-amino]-3',4'-dimethoxyhexanophenone and its hydrochloride which comprises re-acting 6-chloro-3',4'-dimethoxyhexanophenone with N-methylhomoveratrylamine and when the hydrochloride is required reacting the base so obtained with hydrogen chloride.
6. A process for the preparation of 3',4'-dimethoxy-4-{[(3,4-dimethoxy-phenyl)propyl]-methylamino}butyrophenone which comprises reacting 3,4-dimethoxy-.gamma.-chlorobutyrophenone with 3-(3,4-dimethoxyphenyl)-N-methylpropylamine.
7. A process for the preparation of 4-[(3,4-dimethoxy-.alpha.-methylphenethyl)-methylamino]-3',4'-dimethoxybutyrophenone which comprises reacting 3,4-dimethoxy-.gamma.-chlorobutyrophenone with N,.alpha.-dimethyl-.beta.-phenylethylamine.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH18030/73 | 1973-12-21 | ||
| CH1803073A CH611614A5 (en) | 1973-12-21 | 1973-12-21 | Process for the preparation of heterocyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1086320A true CA1086320A (en) | 1980-09-23 |
Family
ID=4429892
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA216,313A Expired CA1057295A (en) | 1973-12-21 | 1974-12-18 | Heterocyclic compounds |
| CA324,131A Expired CA1079290A (en) | 1973-12-21 | 1979-03-26 | Heterocyclic compounds |
| CA324,130A Expired CA1086320A (en) | 1973-12-21 | 1979-03-26 | Heterocyclic compounds |
| CA324,132A Expired CA1072966A (en) | 1973-12-21 | 1979-03-26 | Heterocyclic compounds |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA216,313A Expired CA1057295A (en) | 1973-12-21 | 1974-12-18 | Heterocyclic compounds |
| CA324,131A Expired CA1079290A (en) | 1973-12-21 | 1979-03-26 | Heterocyclic compounds |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA324,132A Expired CA1072966A (en) | 1973-12-21 | 1979-03-26 | Heterocyclic compounds |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS595594B2 (en) |
| AT (5) | AT344693B (en) |
| AU (1) | AU511714B2 (en) |
| BE (1) | BE823625A (en) |
| CA (4) | CA1057295A (en) |
| CH (3) | CH611614A5 (en) |
| DD (1) | DD116829A5 (en) |
| DE (2) | DE2460593C3 (en) |
| DK (1) | DK148323C (en) |
| ES (5) | ES433172A1 (en) |
| FI (1) | FI67216C (en) |
| FR (1) | FR2255064B1 (en) |
| GB (3) | GB1489086A (en) |
| HK (1) | HK43380A (en) |
| HU (1) | HU170429B (en) |
| IE (1) | IE40788B1 (en) |
| IL (3) | IL46146A (en) |
| LU (1) | LU71530A1 (en) |
| NL (1) | NL158496B (en) |
| NO (1) | NO142669C (en) |
| PH (3) | PH19393A (en) |
| SE (2) | SE415763B (en) |
| YU (1) | YU39311B (en) |
| ZA (1) | ZA747526B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2515173A1 (en) * | 1981-10-28 | 1983-04-29 | Delalande Sa | 3-Methoxy 4-alkoxy benzaldehyde(s) - useful as intermediates for antibacterials, esp. trimethoprim and tetroxoprim |
| JPS60142297U (en) * | 1984-02-29 | 1985-09-20 | 株式会社豊田自動織機製作所 | Rotating device for swiveling driver's seat in forklift |
| JPS62171328U (en) * | 1986-04-23 | 1987-10-30 | ||
| DE3642331A1 (en) * | 1986-12-11 | 1988-06-23 | Basf Ag | BASICLY SUBSTITUTED PHENYL ACETONITRILES, THEIR PRODUCTION AND THE MEDICINAL PRODUCTS CONTAINING THEM |
| US5434179A (en) * | 1989-06-06 | 1995-07-18 | Takeda Chemical Industries, Ltd. | Method for improving brain function using cholinesterase-inhibiting aminoketone compounds |
| BR0215389A (en) | 2001-12-28 | 2004-10-26 | Takeda Chemical Industries Ltd | Preventive or therapeutic agent for urinary disorder, method for preventing or treating urinary disorder, use of a compound, compound, prodrug, process for preparing the compound, medicament, and method for screening a compound |
| US20100137403A1 (en) * | 2008-07-10 | 2010-06-03 | Scott Malstrom | Method for enhancing cognition or inhibiting cognitive decline |
-
1973
- 1973-12-21 CH CH1803073A patent/CH611614A5/en not_active IP Right Cessation
-
1974
- 1974-07-19 PH PH20012A patent/PH19393A/en unknown
- 1974-11-25 ZA ZA00747526A patent/ZA747526B/en unknown
- 1974-11-28 IL IL46146A patent/IL46146A/en unknown
- 1974-12-05 FI FI3527/74A patent/FI67216C/en active
- 1974-12-09 IE IE2531/74A patent/IE40788B1/en unknown
- 1974-12-17 PH PH16639A patent/PH13326A/en unknown
- 1974-12-18 YU YU3368/74A patent/YU39311B/en unknown
- 1974-12-18 NL NL7416507.A patent/NL158496B/en not_active IP Right Cessation
- 1974-12-18 CA CA216,313A patent/CA1057295A/en not_active Expired
- 1974-12-19 LU LU71530A patent/LU71530A1/xx unknown
- 1974-12-19 DK DK668174A patent/DK148323C/en not_active IP Right Cessation
- 1974-12-19 DD DD183214A patent/DD116829A5/xx unknown
- 1974-12-19 SE SE7416086A patent/SE415763B/en not_active IP Right Cessation
- 1974-12-20 AT AT1022674A patent/AT344693B/en not_active IP Right Cessation
- 1974-12-20 NO NO744615A patent/NO142669C/en unknown
- 1974-12-20 DE DE2460593A patent/DE2460593C3/en not_active Expired
- 1974-12-20 DE DE2463173A patent/DE2463173C2/de not_active Expired
- 1974-12-20 GB GB55146/74A patent/GB1489086A/en not_active Expired
- 1974-12-20 GB GB23143/77A patent/GB1489088A/en not_active Expired
- 1974-12-20 HU HUHO1757A patent/HU170429B/hu unknown
- 1974-12-20 JP JP49145875A patent/JPS595594B2/en not_active Expired
- 1974-12-20 BE BE151729A patent/BE823625A/en not_active IP Right Cessation
- 1974-12-20 ES ES433172A patent/ES433172A1/en not_active Expired
- 1974-12-20 GB GB23144/77A patent/GB1489087A/en not_active Expired
- 1974-12-23 FR FR7442521A patent/FR2255064B1/fr not_active Expired
-
1976
- 1976-09-01 ES ES451134A patent/ES451134A1/en not_active Expired
- 1976-09-01 ES ES451137A patent/ES451137A1/en not_active Expired
- 1976-09-01 ES ES451135A patent/ES451135A1/en not_active Expired
- 1976-09-01 ES ES451136A patent/ES451136A1/en not_active Expired
-
1977
- 1977-07-19 PH PH20013A patent/PH13396A/en unknown
- 1977-08-29 IL IL52843A patent/IL52843A0/en not_active IP Right Cessation
- 1977-08-29 IL IL52844A patent/IL52844A0/en unknown
-
1978
- 1978-01-06 AU AU32242/78A patent/AU511714B2/en not_active Expired
- 1978-01-19 AT AT38778A patent/AT349012B/en not_active IP Right Cessation
- 1978-01-19 AT AT38978A patent/AT350053B/en not_active IP Right Cessation
- 1978-01-19 AT AT38878A patent/AT349013B/en not_active IP Right Cessation
- 1978-01-19 AT AT39178A patent/AT349014B/en not_active IP Right Cessation
- 1978-04-27 SE SE7804879A patent/SE434746B/en not_active IP Right Cessation
- 1978-06-15 CH CH654178A patent/CH620921A5/en not_active IP Right Cessation
- 1978-06-15 CH CH654078A patent/CH620920A5/en not_active IP Right Cessation
-
1979
- 1979-03-26 CA CA324,131A patent/CA1079290A/en not_active Expired
- 1979-03-26 CA CA324,130A patent/CA1086320A/en not_active Expired
- 1979-03-26 CA CA324,132A patent/CA1072966A/en not_active Expired
-
1980
- 1980-08-14 HK HK433/80A patent/HK43380A/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5225585A (en) | Production of fluoxetine and new intermediates | |
| KR870001382B1 (en) | Process for preparing triazine derivatives | |
| CA1086320A (en) | Heterocyclic compounds | |
| US5312927A (en) | Preparation of imidazoles | |
| Roberts et al. | Rearrangements in the Reactions of 2-(4-Substituted)-phenylethylamines-1-C14 with Nitrous Acid1, 2 | |
| KR101100064B1 (en) | Process for preparing nitrooxyderivatives of naproxen | |
| US4009172A (en) | 2,3,3A,6,7,7A-Hexahydro-thieno[3,2-b]pyridin-(4H)5-ones | |
| US4153631A (en) | Process for processing silver halide developing agents | |
| KR910003636B1 (en) | Process for the preparation of benzophenon oxime compounds | |
| US5874611A (en) | Butenyl hydroquinone derivatives | |
| JPS607632B2 (en) | Method for producing thieno(3,2-C)pyridine and its derivatives | |
| JP4245490B2 (en) | 2- (Dichlorophenyl) -4-phenylimidazole compound | |
| US3123648A (en) | Substituted-benzyl | |
| JPH01207276A (en) | Novel propane derivative | |
| IE911191A1 (en) | Method of producing alkanesulfonanilide derivatives | |
| SU1325052A1 (en) | Method of producing 5-5-bis(2-methyl-5-nitro-1,3-dioxanyl) | |
| IE47627B1 (en) | Oxaminic acids and esters, process for their preparation and pharmaceutical compositions containing them | |
| US6433176B1 (en) | Method for making 8-hydroxyjulolidine compound | |
| US4230871A (en) | Process for preparing 5,6-dihydro-2-methyl-1,4-oxathiin derivatives | |
| US4326076A (en) | Method for preparing the optically active isomer of 2,2-[[5-[3-[(1,1-dimethylethyl)amino]-2-hydroxypropoxy]-1,2,3,4-tetrahydro-2,3-naphthalene-diyl]bis(oxy)]bis[N,N-dipropylacetamide] | |
| US4208510A (en) | Preparation of 3-aryl-isoxazol-5-yl benzoates | |
| SU707520A3 (en) | Method of preparing anilinomethylenemalononitrile derivatives | |
| US4558143A (en) | Process for preparing 4-oxo-4,5,6,7-tetrahydrobenzofuran | |
| IE57221B1 (en) | Process and intermediates for preparation of 4-acetyl-2-substituted imidazoles | |
| KR800001129B1 (en) | Process for 2-(thienyl-3'-amino)-1,3-diaza-cycloalkene |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |