Nitrile compound

Details Nitrile compound Nitrile compound

2001-08-27

2003-12-23

Gerstl, Robert (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitriles

C558S410000

Reexamination Certificate

active

06667412

ABSTRACT:

TECHNICAL FIELD
The present invention relates to a novel nitrile compound useful as an intermediate for the production of, for example, N,N-substituted cyclic amine derivatives useful as medicine as disclosed in WO00/05210 (published Feb. 3, 2000) or phenylacetonitrile derivatives useful as medicine as disclosed in JP-A-63-156,763 (EP-271,013). More particularly, it relates to a nitrile carboxylic acid compound, nitrile ester compound and nitrile alcohol compound.
PRIOR ART
N,N-Substituted cyclic amine derivatives disclosed in WO00/05210 (published Feb. 3, 2000) or phenylacetonitrile derivatives disclosed in JP-A 63-156763 (EP-271013), for example, have been synthesized by reductive amination using aldehyde derivatives and amine derivatives.
Although the above reductive amination is an excellent reaction from the viewpoint of yield, the aldehyde derivatives that serve as a raw material have various problems. That is, they have very high reactivity so that their stability is poor (oxidation, decomposition, polymerization etc.), by-products that are difficult to purify tend to occur depending on the reaction conditions, generally they are expensive, and the like.
DISCLOSURE OF THE INVENTION
Accordingly, the present inventors have made extensive studies paying attention to novel compounds having utility from the viewpoints of raw material stability, production costs, manipulability (workability), final product purity and so forth. As a result, they have found out that novel nitrile compounds, more particularly nitrile carboxylic acid compounds, nitrile ester compounds and nitrile alcohol compounds can solve the above problems simultaneously, thereby achieving the present invention.
Therefore, an object of the present invention is to provide novel intermediates useful for the production of fine chemicals such as medicines.
The present invention is a nitrile compound represented by the following formula (I).
Wherein
R
1
s are the same as or different from each other and each means hydrogen atom, a halogen atom, hydroxyl group, a lower alkyl group, a lower cycloalkyl group, a lower alkoxy group, a lower alkoxyalkoxy group, a halogenated lower alkyl group, a hydroxy-lower alkyl group, a cyano-lower alkyl group, a halogenated lower alkoxy group, a hydroxy-lower alkoxy group, a cyano-lower alkoxy group, a lower acyl group, nitro group, an optionally substituted amino group, an optionally substituted carbamoyl group, an optionally substituted sulfamoyl group, mercapto group or a lower alkylthio group;
R
2
means a lower alkyl group or a lower cycloalkyl group, and two R
1
s may combine to form an aliphatic ring, an aromatic ring, a hetero ring or an alkylenedioxy ring;
n means 0 or an integer of from 1 to 5;
m means 0 or an integer of from 1 to 6; and
R
3
means carboxyl group, a lower alkoxycarbonyl group, a phenyloxycarbonyl group optionally having a substituent, a phenyl-lower alkylenyl group optionally having a substituent, or hydroxymethyl group.
In the above definitions, the term “halogen atom” specifically means, for example, fluorine, chlorine, bromine or iodine.
The term “lower alkyl group” means an alkyl group having 1 to 6 carbon atoms and specifically includes, for example, straight chain or branched alkyl groups, such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, t-butyl group, n-pentyl group, i-pentyl group, neopentyl group, hexyl group, 1-methylpropyl group, 1-methylbutyl group and 2-methylbutyl group. The term “lower alkylenyl group” means an alkylene chain composed of the above-mentioned alkyl group, including, for example, methylene group, ethylene group, propylene group and so forth.
The term “lower cycloalkyl group” means a cyclic alkyl group having 3 to 8 carbon atoms and specifically includes, for example, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group and so forth.
The term “lower alkoxy group” means a group resulting from a combination of the above-mentioned lower alkyl group with oxygen atom, and specifically includes straight chain or branched alkoxy groups, for example, methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, i-butoxy group, t-butoxy group, pentyloxy group, hexyloxy group and so forth.
The term “lower alkoxyalkoxy group” means a group resulting from a combination of the above-mentioned alkoxy group with another lower alkoxy group, and specifically includes, for example, methoxymethoxy group, methoxyethoxy group, methoxypropoxy group, ethoxymethoxy group, ethoxyethoxy group, ethoxypropoxy group, propoxymethoxy group, propoxyethoxy group, propoxypropoxy group and so forth.
The term “halogenated lower alkyl group” means a group resulting from combination of the above-mentioned lower alkyl group with one or more halogen atoms, which may be the same as or different from, and specifically includes, for example, chloromethyl group, dichloromethyl group, trichloromethyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, fluoroethyl group, difluoroethyl group, trifluoroethyl group and so forth.
The term “hydroxy lower alkyl group” means a group resulting from combination of the above-mentioned alkyl group with one or more hydroxyl groups, and specifically includes, for example, hydroxymethyl group, hydroxyethyl group, 2,3-dihydroxypropyl group and so forth.
The term “cyano lower alkyl group” means a group resulting from combination of the above-mentioned lower alkyl group with one or more cyano groups, and specifically includes, for example, cyanomethyl group, cyanoethyl group, cyanopropyl group and so forth.
The terms “halogenated lower alkoxy group”, “hydroxy lower alkoxy group”, and “cyano lower alkoxy group” mean a group resulting from a combination of the above-mentioned halogenated lower alkyl group with an oxygen atom, a group resulting from a combination of the above-mentioned hydroxy lower alkyl group with an oxygen atom, and a group resulting from a combination of the above-mentioned cyano lower alkyl group with an oxygen atom, respectively.
The term “lower acyl group” means a straight chain or branched acyl group derived from a fatty acid having 1 to 6 carbon atoms, and specifically includes, for example, formyl group, acetyl group, propionyl group, butyryl group, isobutyryl group, valeryl group, isovaleryl group, pivaloyl group, hexanoyl group and so forth.
The term “optionally substituted amino group” means an amino group whose nitrogen atom may be substituted with a lower alkyl group or the like. It also includes the case where the nitrogen atom is a part of a cyclic amine. Specific examples thereof include amino group (—NH
2
), methylamino group (—NHCH
3
), dimethylamino group (—N(CH
3
)
2
), ethylamino group (—NHC
2
H
5
), diethylamino group (—N(C
2
H
5
)
2
), methylethylamino group (—N(CH
3
)C
2
H
5
), pyrrolidinyl group, pyrazolinyl group, piperidinyl group, piperazinyl group, 4-morpholinyl group, 4-thiomorpholinyl group and so forth.
The term “optionally substituted carbamoyl group” means a carbamoyl group whose nitrogen atom may be substituted with a lower alkyl group or the like, and also includes the case where the nitrogen atom is apart of a cyclic amine. Specific examples thereof include carbamoyl group (—CONH
2
), N-methylcarbamoyl group (—CONHCH
3
), N,N-dimethylcarbamoyl group (—CON(CH
3
)
2
), N-ethylcarbamoyl group (—CONHC
2
H
5
), N,N-diethylcarbamoyl group (—CON(C
2
H
5
)), N-methyl-N-ethylcarbamoyl group (—CON(CH
3
)C
2
H
5
), 1-pyrrolidinylcarbonyl group, 1-pyrazolinylcarbonyl group, 1-piperidinylcarbonyl group, 1-piperazinylcarbonyl group, 4-morpholinylcarbonyl group, 4-thiomorpholinylcarbonyl group and so forth.
The term “optionally substituted sulfamoyl group” means a sulfamoyl group whose nitrogen atom may be substituted with a lower alkyl group or the like, and includes also the case where the nitrogen atom is apart of a cyclic amine. Specific examples thereof include sulfamoyl group (—SO
2
NH
2
), N-methylsulfamoyl group (—SO
2
NHCH
3
), N,N-dimethylsulfamoyl grou

Affiliated with

Also associated with

Rating

Nitrile compound does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Nitrile compound, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Nitrile compound will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3163490