ES263335A1 - Phenylcyclopropyl amides - Google Patents
Phenylcyclopropyl amidesInfo
- Publication number
- ES263335A1 ES263335A1 ES0263335A ES263335A ES263335A1 ES 263335 A1 ES263335 A1 ES 263335A1 ES 0263335 A ES0263335 A ES 0263335A ES 263335 A ES263335 A ES 263335A ES 263335 A1 ES263335 A1 ES 263335A1
- Authority
- ES
- Spain
- Prior art keywords
- lower alkyl
- amino
- nitrogen
- substituted
- mercapto
- 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
- AOTWIFLKURJQGE-UHFFFAOYSA-N n-cyclopropylaniline Chemical class C1CC1NC1=CC=CC=C1 AOTWIFLKURJQGE-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 20
- 150000001875 compounds Chemical class 0.000 abstract 5
- -1 (mercapto)-(amino) Chemical class 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 239000000969 carrier Substances 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 2
- 206010002383 Angina Pectoris Diseases 0.000 abstract 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 abstract 1
- 102000010909 Monoamine Oxidase Human genes 0.000 abstract 1
- 108010062431 Monoamine oxidase Proteins 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 206010003246 arthritis Diseases 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000007858 starting material Substances 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
- C07D295/14—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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of general formula: <FORM:0961313/C1/1> wherein R is hydrogen, lower (1-8C) alkyl, lower alkenyl, phenyl-lower alkyl, nuclear substituted phenyl-lower alkyl, cycloalkyl, cycloalkyl-lower alkyl, hydroxy-lower alkyl, halo-lower alkyl, dicyclic hydroxy methyl, mono- or di-amino-lower alkyl, (halophenoxy)-lower alkyl, (mercapto)-(amino)-substituted lower alkyl, (alkyl-mercapto)-(amino)-substituted lower alkyl, (hydroxy)-(amino)-substituted lower alkyl, o -carboxy-(amino)-lower alkyl, a nitrogen-containing heterocyclyl group, an o -(nitrogen-containing heterocyclyl)-(amino)-lower alkyl group, or an o -(nitrogen-containing heterocyclyl)-lower alkyl group trans isomers are preferred: and the process of reacting a compound of formula: <FORM:0961313/C1/2> with a compound of formula: <FORM:0961313/C1/3> in the presence of dicyclohexylcarbodiimide to yield a product of formula: <FORM:0961313/C1/4> wherein R1 is mono- or di-amino-lower alkyl, (mercapto)-(amino), substituted lower alkyl, (alkyl-mercapto)-(amino)-substituted lower alkyl, (hydroxy)-(amino)-substituted lower alkyl, an o -carboxy-(amino)-lower alkyl group, a nitrogen-containing heterocyclyl group, or an o -(nitrogen-containing-heterocyclyl) - (amino) - lower alkyl group. Other processes exemplified use as starting material acid halides which are reacted with the phenylcyclopropylamine N-(trans-2-phenylcyclopropyl)-2-piperidino-acetamide is prepared by reacting the chloroacetamide with piperidine. Pharmaceutical compositions are mentioned which comprise compounds I together with suitable carriers for administration to humans and animals. Oral administration and solid (tablets, capsules) and liquid carriers are mentioned. The compounds inhibit monoamine oxidase and are used in depression, angina pectoris and arthritis.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US1114260A | 1960-02-26 | 1960-02-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
ES263335A1 true ES263335A1 (en) | 1961-04-16 |
Family
ID=21749061
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES0263335A Expired ES263335A1 (en) | 1960-02-26 | 1960-12-17 | Phenylcyclopropyl amides |
Country Status (5)
Country | Link |
---|---|
DE (1) | DE1234728B (en) |
DK (1) | DK110096C (en) |
ES (1) | ES263335A1 (en) |
FR (1) | FR1445453A (en) |
GB (1) | GB961313A (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3954777A (en) * | 1970-03-03 | 1976-05-04 | Zambon S.P.A. | Aminopropionyl derivatives of 2,3-diphenyl cyclopropylamine |
US3954778A (en) * | 1970-03-03 | 1976-05-04 | Zambon S.P.A. | Aminoacetyl derivatives of 2,3-diphenyl cyclopropyl amine |
-
1960
- 1960-12-14 GB GB4308160A patent/GB961313A/en not_active Expired
- 1960-12-17 ES ES0263335A patent/ES263335A1/en not_active Expired
-
1961
- 1961-02-10 DK DK56461A patent/DK110096C/en active
- 1961-02-23 FR FR853691A patent/FR1445453A/en not_active Expired
-
1962
- 1962-03-17 DE DEL41511A patent/DE1234728B/en active Pending
Also Published As
Publication number | Publication date |
---|---|
DK110096C (en) | 1968-11-04 |
GB961313A (en) | 1964-06-17 |
FR1445453A (en) | 1966-07-15 |
DE1234728B (en) | 1967-02-23 |
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