US3846470A - Derivatives of 3-benzoyl-2-({62 -hydroxyphenethylamino)-propionitrile - Google Patents

Derivatives of 3-benzoyl-2-({62 -hydroxyphenethylamino)-propionitrile Download PDF

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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
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US
United States
Prior art keywords
stands
group
member selected
propionitrile
nucleus
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Expired - Lifetime
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US00239359A
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English (en)
Inventor
T Raabe
J Scholtholt
R Nitz
A Stachel
I Stachel
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Cassella Farbwerke Mainkur AG
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Cassella Farbwerke Mainkur AG
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Priority to US359440A priority Critical patent/US3867389A/en
Priority to US359442A priority patent/US3864344A/en
Application granted granted Critical
Publication of US3846470A publication Critical patent/US3846470A/en
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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.

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  • 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)
US00239359A 1971-04-02 1972-03-29 Derivatives of 3-benzoyl-2-({62 -hydroxyphenethylamino)-propionitrile Expired - Lifetime US3846470A (en)

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

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ID=5803749

Family Applications (1)

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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 (xx)
AR (3) AR192920A1 (xx)
AT (3) AT315185B (xx)
BE (1) BE781544A (xx)
CS (3) CS159703B2 (xx)
DD (1) DD96702A5 (xx)
DE (1) DE2116293A1 (xx)
FR (1) FR2132354B1 (xx)
GB (1) GB1346029A (xx)
NL (1) NL7203630A (xx)
SU (1) SU439983A3 (xx)

Cited By (13)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Patent Citations (2)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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
CS159701B2 (xx) 1975-01-31
CS159703B2 (xx) 1975-01-31
DE2116293A1 (de) 1972-10-19
FR2132354B1 (xx) 1975-04-25
BE781544A (fr) 1972-10-02
AR192920A1 (es) 1973-03-21
NL7203630A (xx) 1972-10-04
DD96702A5 (xx) 1973-04-05
AT315857B (de) 1974-06-10
SU439983A3 (ru) 1974-08-15
AR193462A1 (es) 1973-04-23
AR199200A1 (es) 1974-08-14
GB1346029A (xx) 1974-02-06
AT316522B (de) 1974-07-10
CS159702B2 (xx) 1975-01-31
AT315185B (de) 1974-05-10
FR2132354A1 (xx) 1972-11-17

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