US3846470A - Derivatives of 3-benzoyl-2-({62 -hydroxyphenethylamino)-propionitrile - Google Patents
Derivatives of 3-benzoyl-2-({62 -hydroxyphenethylamino)-propionitrile Download PDFInfo
- Publication number
- US3846470A US3846470A US00239359A US23935972A US3846470A US 3846470 A US3846470 A US 3846470A US 00239359 A US00239359 A US 00239359A US 23935972 A US23935972 A US 23935972A US 3846470 A US3846470 A US 3846470A
- Authority
- US
- United States
- Prior art keywords
- stands
- group
- member selected
- propionitrile
- nucleus
- 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 - Lifetime
Links
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
- C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- 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
Definitions
- the present invention relates to new pharmacologically valuable ketone derivatives exhibiting a distinct dilatory action on the cerebral vessels and which have the general formula and their pharmaceutically acceptable acid addition salts, wherein R stands for a member selected from the group consisting of CN, CONHg, COOH. COONa and COOK, R stands for a member selected from the group consisting of and X stands for alkylene having I to 4, carbon atoms, Y stands for a member selected from the group consisting of OCO- and CONH,
- R 3 and R each stand for a member selected from the group consisting of hydrogen and alkyl having I to 6 carbon atoms,
- R stands for a member selected from the group consisting of hydrogen and OH
- the nucleus 1 may have 1 to 3 alkoxy, halogen,
- the nucleus 11 may have 1 to 3 alkoxy, halogen or alkyl substituents,
- the nucleus III may be substituted by 1 to 3 methoxy groups and to processes for producing said ketone derivatives.
- R stands for -N N X Y -@-or f CH 1 X stands for alkylene having 1 to 4 carbon atoms
- Y stands for OCO- or CONH R and R each stand for hydrogen or alkyl having up to 6 carbon atoms, and
- R stands for hydrogen, or OH
- nucleus I may have I to 3 alkoxy, halogen, alkyl or nitro substituents,
- nucleus Il may have 1 to 3 alkoxy, halogen or alkyl substituents, and
- the nucleus III may be substituted by l to 3 methoxy groups.
- the compounds of general formula I contain at least one basic nitrogen atom and may consequently form or be formed as salts, in particular hydrohalides, and the invention extends to such acid addition salts, where 'pharmaceutically acceptable.
- Preferred halogen substituents for the nucleus I and- /or the nucleus II are fluorine, chlorine and bromine.
- Preferred alkyl substituents of the nucleus I and of the nucleus II contain 1 to 8 carbon atoms.
- Preferred alkoxy substuents are methoxy groups.
- the compounds of formula I may be prepared, for example,
- Xl may be 7 7 prepared, as far as they are not yet described in literature, according to known per se methods.
- the compounds of the present invention and their pharmaceutically acceptable salts may be employed together with pharamaceutically acceptable diluents or carriers for the preparation of pharmaceutical formulations such as tablets, dragees, suppositories, capsules, solutions, suspensions or emulsions.
- These pharmaceutical preparations may also contain other therapeutically active substances.
- hydrochloride (a-methyl-B-hydroxy- 2.0 14 l1 l0 +25l+50 l7 phenethylamino)-pt'opioi.v.
- the 2',3,4'trimethoxybenzoylacrylic acid required as starting material may be prepared as follows:
- the 2',3',4'-trimethoxybenzoylacrylic acid amide required as starting material may be prepared as followsr 8 g. 2',3,4'-trimethoxybenzoylacrylonitril are dissolved in 40 c.c. concentrated sulfuric acid and heated etheric hydrochloric acid, and the precipitate is sucked off and washed several times with ether. Subsequently, it is treated with water, whereby first muddy mass is formed which solidifies while further standing.
- the solid product is sucked off, suspended in dilute soda solution and immediately extracted three times with chloroform.
- the chloroform solution is washed with water, dried and concentrated in vacuo.
- the resinous residue is dissolved in anhydrous dioxane, admixed with etheric hydrochloric acid and the separated precipitate is sucked off and washed with ether.
- the residue is then stirred for one hour in about 30 c.c. water, whereby first a muddy mass is again formed which solidifies after a short while.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US359440A US3867389A (en) | 1972-03-29 | 1973-05-11 | Alpha-(n-benzoyloxy and phenylamino alkyl-piperazino)-beta-benzoyl-propionic acid derivatives |
US359442A US3864344A (en) | 1971-04-02 | 1973-05-11 | 3-(Benzoyl)-2-(4{40 -anilino carbonyl or benzoxy-alkyl piperazino)-propionitriles |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19712116293 DE2116293A1 (de) | 1971-04-02 | 1971-04-02 | Ketonderivate und Verfahren zu ihrer Herstellung |
Publications (1)
Publication Number | Publication Date |
---|---|
US3846470A true US3846470A (en) | 1974-11-05 |
Family
ID=5803749
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00239359A Expired - Lifetime US3846470A (en) | 1971-04-02 | 1972-03-29 | Derivatives of 3-benzoyl-2-({62 -hydroxyphenethylamino)-propionitrile |
Country Status (11)
Country | Link |
---|---|
US (1) | US3846470A (fr) |
AR (3) | AR192920A1 (fr) |
AT (3) | AT316522B (fr) |
BE (1) | BE781544A (fr) |
CS (3) | CS159703B2 (fr) |
DD (1) | DD96702A5 (fr) |
DE (1) | DE2116293A1 (fr) |
FR (1) | FR2132354B1 (fr) |
GB (1) | GB1346029A (fr) |
NL (1) | NL7203630A (fr) |
SU (1) | SU439983A3 (fr) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3980643A (en) * | 1974-01-04 | 1976-09-14 | Hokuriku Pharmaceutical Co., Ltd. | Novel piperazine- and homopiperazine-monoalkanol esters and a process of production thereof |
DE3214082A1 (de) * | 1981-04-17 | 1982-11-04 | Roussel-Uclaf, 75007 Paris | Neue derivate von phenyl-aliphatischen carbonsaeuren, deren herstellung, deren verwendung als arzneimittel und die sie enthaltenden zusammensetzungen |
US4384137A (en) * | 1980-09-04 | 1983-05-17 | Societe Francaise Hoechst | Process for preparation of hydroxyarylglyoxylic acids and their alkaline salts, and application thereof to preparation of sodium parahydroxyphenylglyoxylate |
US4402978A (en) * | 1980-04-24 | 1983-09-06 | Roussel-Uclaf | Gastro-protecting activity of substituted derivatives of 4-phenyl-4-oxo-2-hydroxy-butanoic acid |
US4436752A (en) | 1981-04-17 | 1984-03-13 | Roussel Uclaf | Treatment of gastric and gastro-duodenal disorders with derivatives of phenyl aliphatic carboxylic acids |
US4454155A (en) * | 1981-10-22 | 1984-06-12 | Roussel Uclaf | Pharmaceutical compositions containing a mono-substituted derivative of 4-phenyl-4-oxobuten-2-oic acid, and methods of using them in treating gastric and gastroduodenal ailments |
US4473583A (en) * | 1981-10-22 | 1984-09-25 | Roussel Uclaf | Compositions containing certain derivatives of 4-phenyl-4-oxobuten-2-oic acid and methods of treatment using them |
US4483868A (en) * | 1980-04-24 | 1984-11-20 | Roussel Uclaf | Gastro-protecting activity |
US4486429A (en) * | 1981-10-22 | 1984-12-04 | Roussel Uclaf | Amino derivatives of 4-phenyl 4-oxobuten-2-oic acid, pharmaceutical compositions containing them, and methods for preparing and therapeutically using them |
US4594443A (en) * | 1983-08-25 | 1986-06-10 | Roussel-Uclaf | Derivatives of 4-phenyl-4-oxo-buten-2-oic acid and therapeutic use thereof |
US4751324A (en) * | 1985-06-13 | 1988-06-14 | Henkel Kommanditgesellschaft Auf Aktien | Benzoyl alanine compounds and their use as corrosion inhibitors |
US4814348A (en) * | 1983-01-24 | 1989-03-21 | Roussel Uclaf | Therapeutic compositions containing derivatives of acrylic acid having an oxygen-containing heterocycle, therapeutic treatment therewith and new compounds |
US5234894A (en) * | 1991-03-29 | 1993-08-10 | Tokuyama Soda Kabushiki Kaisha | Carbonyl acetonitrile derivative and herbicide containing it as an active component |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1574019A (en) | 1977-01-14 | 1980-09-03 | Joullie International Sa | Therapeutically useful 3,4,5-trimethoxybenzene derivatives |
DE4443465A1 (de) * | 1994-12-07 | 1996-06-13 | Chemie Linz Deutschland | Verfahren zur Herstellung von (S,S)-(N-(1-Ethoxycarbonyl-3-oxo-3-phenylpropyl)-alanin)-(phenylmethyl)ester |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3225095A (en) * | 1962-03-31 | 1965-12-21 | Degussa | N-aryl-substituted-propan-(1)-ones and -ols of arylaminoalkanols and salts thereof |
US3646145A (en) * | 1967-06-29 | 1972-02-29 | Degussa | N-(1-hydroxy-1-phenyl-ethyl amino)-propiophenones |
-
1971
- 1971-04-02 DE DE19712116293 patent/DE2116293A1/de active Pending
-
1972
- 1972-03-17 NL NL7203630A patent/NL7203630A/xx unknown
- 1972-03-28 AR AR241197A patent/AR192920A1/es active
- 1972-03-29 US US00239359A patent/US3846470A/en not_active Expired - Lifetime
- 1972-03-30 DD DD161945A patent/DD96702A5/xx unknown
- 1972-03-30 GB GB15036/72*2A patent/GB1346029A/en not_active Expired
- 1972-03-31 AT AT282172A patent/AT316522B/de not_active IP Right Cessation
- 1972-03-31 AT AT460773A patent/AT315857B/de not_active IP Right Cessation
- 1972-03-31 SU SU1768202A patent/SU439983A3/ru active
- 1972-03-31 CS CS675*[A patent/CS159703B2/cs unknown
- 1972-03-31 FR FR7211561A patent/FR2132354B1/fr not_active Expired
- 1972-03-31 AT AT460873A patent/AT315185B/de not_active IP Right Cessation
- 1972-03-31 BE BE781544A patent/BE781544A/fr unknown
- 1972-03-31 CS CS674*[A patent/CS159702B2/cs unknown
- 1972-03-31 CS CS2198A patent/CS159701B2/cs unknown
-
1973
- 1973-02-01 AR AR246385A patent/AR199200A1/es active
- 1973-02-01 AR AR246384A patent/AR193462A1/es active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3225095A (en) * | 1962-03-31 | 1965-12-21 | Degussa | N-aryl-substituted-propan-(1)-ones and -ols of arylaminoalkanols and salts thereof |
US3646145A (en) * | 1967-06-29 | 1972-02-29 | Degussa | N-(1-hydroxy-1-phenyl-ethyl amino)-propiophenones |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3980643A (en) * | 1974-01-04 | 1976-09-14 | Hokuriku Pharmaceutical Co., Ltd. | Novel piperazine- and homopiperazine-monoalkanol esters and a process of production thereof |
US4483868A (en) * | 1980-04-24 | 1984-11-20 | Roussel Uclaf | Gastro-protecting activity |
US4402978A (en) * | 1980-04-24 | 1983-09-06 | Roussel-Uclaf | Gastro-protecting activity of substituted derivatives of 4-phenyl-4-oxo-2-hydroxy-butanoic acid |
US4384137A (en) * | 1980-09-04 | 1983-05-17 | Societe Francaise Hoechst | Process for preparation of hydroxyarylglyoxylic acids and their alkaline salts, and application thereof to preparation of sodium parahydroxyphenylglyoxylate |
DE3214082A1 (de) * | 1981-04-17 | 1982-11-04 | Roussel-Uclaf, 75007 Paris | Neue derivate von phenyl-aliphatischen carbonsaeuren, deren herstellung, deren verwendung als arzneimittel und die sie enthaltenden zusammensetzungen |
US4436752A (en) | 1981-04-17 | 1984-03-13 | Roussel Uclaf | Treatment of gastric and gastro-duodenal disorders with derivatives of phenyl aliphatic carboxylic acids |
US4450292A (en) * | 1981-04-17 | 1984-05-22 | Roussel Uclaf | Derivatives of phenyl aliphatic carboxylic acids, and use thereof in treating gastric and gastro-duodenal ailments |
US4454155A (en) * | 1981-10-22 | 1984-06-12 | Roussel Uclaf | Pharmaceutical compositions containing a mono-substituted derivative of 4-phenyl-4-oxobuten-2-oic acid, and methods of using them in treating gastric and gastroduodenal ailments |
US4473583A (en) * | 1981-10-22 | 1984-09-25 | Roussel Uclaf | Compositions containing certain derivatives of 4-phenyl-4-oxobuten-2-oic acid and methods of treatment using them |
US4486429A (en) * | 1981-10-22 | 1984-12-04 | Roussel Uclaf | Amino derivatives of 4-phenyl 4-oxobuten-2-oic acid, pharmaceutical compositions containing them, and methods for preparing and therapeutically using them |
US4814348A (en) * | 1983-01-24 | 1989-03-21 | Roussel Uclaf | Therapeutic compositions containing derivatives of acrylic acid having an oxygen-containing heterocycle, therapeutic treatment therewith and new compounds |
US4594443A (en) * | 1983-08-25 | 1986-06-10 | Roussel-Uclaf | Derivatives of 4-phenyl-4-oxo-buten-2-oic acid and therapeutic use thereof |
US4751324A (en) * | 1985-06-13 | 1988-06-14 | Henkel Kommanditgesellschaft Auf Aktien | Benzoyl alanine compounds and their use as corrosion inhibitors |
US5234894A (en) * | 1991-03-29 | 1993-08-10 | Tokuyama Soda Kabushiki Kaisha | Carbonyl acetonitrile derivative and herbicide containing it as an active component |
Also Published As
Publication number | Publication date |
---|---|
AT315185B (de) | 1974-05-10 |
CS159703B2 (fr) | 1975-01-31 |
AR192920A1 (es) | 1973-03-21 |
GB1346029A (fr) | 1974-02-06 |
DE2116293A1 (de) | 1972-10-19 |
NL7203630A (fr) | 1972-10-04 |
FR2132354A1 (fr) | 1972-11-17 |
DD96702A5 (fr) | 1973-04-05 |
AR193462A1 (es) | 1973-04-23 |
CS159702B2 (fr) | 1975-01-31 |
AT316522B (de) | 1974-07-10 |
SU439983A3 (ru) | 1974-08-15 |
AR199200A1 (es) | 1974-08-14 |
BE781544A (fr) | 1972-10-02 |
FR2132354B1 (fr) | 1975-04-25 |
AT315857B (de) | 1974-06-10 |
CS159701B2 (fr) | 1975-01-31 |
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