JP2002356472A5 - - Google Patents
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- JP2002356472A5 JP2002356472A5 JP2001309559A JP2001309559A JP2002356472A5 JP 2002356472 A5 JP2002356472 A5 JP 2002356472A5 JP 2001309559 A JP2001309559 A JP 2001309559A JP 2001309559 A JP2001309559 A JP 2001309559A JP 2002356472 A5 JP2002356472 A5 JP 2002356472A5
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【0101】
〔C法およびD法における反応〕
C法における反応(化合物[VII]と、化合物[VIII]又はその塩(又は化合物[X])との反応);および
D法における反応(化合物[XI]又は[XIII]と、化合物[XII]又はそれらの塩(又は化合物[X])との反応)は、必要に応じ縮合剤及び/又は脱酸剤の存在下、適当な溶媒中又は無溶媒で行い、更にリンカー及び樹脂残基部分を常法により除去し、必要に応じ、例えば抽出、分配、再沈殿、結晶化、再結晶、各種クロマトグラフィー、高速クロマトグラフィー等によって精製することにより実施できる。[0101]
[Reaction in Method C and Method D]
Reaction in Method C (reaction of Compound [VII] with Compound [VIII] or a salt thereof (or Compound [X] ) ; and Reaction in Method D (Compound [XI] or [XIII] with Compound [XII] Or reaction with their salts (or compound [X] ) , if necessary, in the presence of a condensing agent and / or a deoxidizing agent, in a suitable solvent or in the absence of a solvent, and further containing a linker and a resin residue It can be carried out by removing by a conventional method and, if necessary, purifying by, for example, extraction, distribution, reprecipitation, crystallization, recrystallization, various chromatography, high speed chromatography and the like.
【0261】
(7)前記(6)項で得られる化合物174 mgのアセトニトリル7 ml中の懸濁液に氷冷下ヨウ化トリメチルシリル282μLを加え室温で1時間撹拌する。反応液に氷水を加え、クロロホルムで洗浄後、水層に炭酸カリウムを加えて飽和させ、クロロホルムで3回抽出する。抽出液を硫酸ナトリウムで乾燥し、減圧濃縮することにより、trans-4-(4-アミノ-5-シアノピリミジン-2-イル)シクロヘキシルアミン(表9 参考例8−35)105 mgを得る。[0261]
(7) To a suspension of 174 mg of the compound obtained in the above (6) in 7 ml of acetonitrile is added 282 μL of trimethylsilyl iodide under ice-cooling and stirred at room temperature for 1 hour. Ice water is added to the reaction solution, and after washing with chloroform, potassium carbonate is added to the aqueous layer to saturate, and extraction is performed 3 times with chloroform. The extract was dried over sodium sulfate and concentrated in vacuo to give, trans-4-(4-Amino-5-cyano-2-yl) Shikurohe hexyl amine (Table 9 Reference Example 8-35) obtaining 105 mg.
【0262】
参考例 8−36
trans-4-(ベンジルオキシカルボニルアミノ)-1-シクロヘキサンカルボキサミジン・塩酸塩 (参考例8−35(5)項の化合物) (348 mg) を出発物質とし、Libmanらの方法(J. Chem. Soc.、第2305頁、1952年)に従ってアセチルアセトンと反応させることにより、trans-1-ベンジルオキシカルボニルアミノ-4-(4,6-ジメチルピリミジン-2-イル)シクロヘキサン(220 mg)を得る。
この化合物(205 mg)を、参考例8−35の(7)項と同様にヨウ化トリメチルシリルで処理することにより、trans-4-(4,6-ジメチルピリミジン-2-イル)シクロヘキシルアミン(表9 参考例8−36)(129mg)を得る。[0262]
Reference Example 8-36
trans-4- (benzyloxycarbonylamino) -1-cyclohexanecarboxamidine hydrochloride (compound of Reference Example 8-35 (5)) (348 mg) as a starting material, and the method of Libman et al. (J. Chem) Reaction with acetylacetone according to Soc., Page 2305, 1952) gives trans-1-benzyloxycarbonylamino-4- (4,6-dimethylpyrimidin-2-yl) cyclohexane (220 mg).
The compound (205 mg), by treatment with (7) section as well as trimethylsilyl iodide in Reference Example 8-35, trans-4- (4,6- dimethyl-pyrimidin-2-yl) Shikurohe hexyl amine ( Table 9 Reference Example 8-36) (129 mg) is obtained.
Claims (15)
A:−CH2− 又は −S−、
B:CH、
R1:H、低級アルキル基、ヒドロキシ低級アルキル基 又は
低級アルコキシ低級アルキル基、
X:単結合手、
R2:以下の(1)および(2)から選択される基;
(1)置換されていてもよい環式基であって該環式基部分が(i)単環もしくは二環式炭化水素基 又は(ii)単環もしくは二環式複素環基 である基; 及び
(2)置換もしくは非置換低級アルキル基から選択される同一又は異なる1〜2個の置換基で置換されたアミノ基。〕
で示される脂肪族含窒素五員環化合物又はその薬理的に許容しうる塩。General formula [I]
A: -CH 2 -or -S-,
B: CH ,
R 1 : H, lower alkyl group, hydroxy lower alkyl group or lower alkoxy lower alkyl group,
X: Single bond hand ,
R 2 : a group selected from the following (1) and (2);
(1) a cyclic group which may be substituted, wherein the cyclic group moiety is (i) a monocyclic or bicyclic hydrocarbon group or (ii) a monocyclic or bicyclic heterocyclic group; And (2) an amino group substituted with the same or different 1 to 2 substituents selected from substituted or unsubstituted lower alkyl groups . ]
And an aliphatic nitrogen-containing five-membered ring compound or a pharmacologically acceptable salt thereof.
(1)以下のA群置換基から選択される同一又は異なる1〜3個の置換基を有していてもよい環式基であって該環式基部分が(i)単環もしくは二環式炭化水素基又は(ii)単環もしくは二環式複素環基である基;及び
(2)「シアノ基、低級アルコキシ基、フェニル基および含窒素単環式6員芳香族複素環基から選択される基で置換されていてもよい低級アルキル基」から選択される同一又は異なる1〜2個の置換基で置換されたアミノ基。
A群置換基:
ハロゲン原子、シアノ基、ニトロ基、アミノ基、オキソ基、低級アルキル基、低級アルコキシ基、低級アルカノイル基、低級アルコキシカルボニル基、低級アルコキシカルボニルアミノ基、低級シクロアルカノイル基、ハロ低級アルキル基、ハロ低級アルキルカルボニル基、含窒素単環式5〜6員脂肪族複素環基置換カルボニル基、含窒素単環式6員芳香族複素環基、単環式アリール基、単環式アリール基置換アリール低級アルキルカルボニルアミノ基、低級アルキルチオ基 および アミノスルホニル基。The compound according to claim 1, wherein R 2 is a group selected from the following (1) and (2).
(1) A cyclic group which may have the same or different 1 to 3 substituents selected from the following group A substituents, and the cyclic group moiety is (i) a monocyclic or bicyclic ring Of the formula hydrocarbon group or (ii) a monocyclic or bicyclic heterocyclic group; and (2) selected from a cyano group, a lower alkoxy group, a phenyl group and a nitrogen-containing monocyclic 6-membered aromatic heterocyclic group the same or different 1-2 amino group substituted with a substituent selected from is a lower alkyl group optionally "substituted by a group.
Group A substituent:
Halogen atom, cyano, nitro, amino, oxo, lower alkyl, lower alkoxy, lower alkanoyl, lower alkoxycarbonyl, lower alkoxycarbonylamino, lower cycloalkanoyl, halo lower alkyl, halo lower Alkyl carbonyl group, nitrogen-containing monocyclic 5- to 6-membered aliphatic heterocyclic group-substituted carbonyl group, nitrogen-containing monocyclic 6-membered aromatic heterocyclic group, monocyclic aryl group, monocyclic aryl group-substituted aryl lower alkyl Carbonylamino group, lower alkylthio group and aminosulfonyl group.
(i)炭素数3〜7の単環式炭化水素基、
(ii)窒素原子、酸素原子及び硫黄原子から選ばれる1〜2個の異項原子を含む単環式複素環基、および
(iii)窒素原子、酸素原子及び硫黄原子から選ばれる1〜3個の異項原子を含み、5〜7員環が2個縮合してなる二環式複素環基。The R 2 is a cyclic group which may be substituted, and the cyclic group moiety is a group selected from the following (i), (ii) and (iii): The compound according to item 1.
(I) monocyclic hydrocarbon group having 3 to 7 carbon atoms,
(Ii) monocyclic heterocyclic group containing 1 to 2 hetero atoms selected from nitrogen atom, oxygen atom and sulfur atom, and (iii) 1 to 3 selected from nitrogen atom, oxygen atom and sulfur atom And a hetero ring group formed by condensing two 5- to 7-membered rings.
フェニル基、シクロへキシル基、シクロペンチル基、シクロブチル基、シクロプロピル基、ピロリジニル基、イミダゾリジニル基、ピラゾリジニル基、オキソラニル基、チオラニル基、ピロリニル基、イミダゾリニル基、ピラゾリニル基、ピロリル基、イミダゾリル基、ピラゾリル基、トリアゾリル基、テトラゾリル基、フリル基、オキサゾリル基、イソオキサゾリル基、オキサジアゾリル基、チエニル基、チアゾリル基、イソチアゾリル基、チアジアゾリル基、ピペリジル基、ピペラジニル基、モルホリニル基、チオモルホリニル基、ピリジル基、ピリミジニル基、ピラジニル基、ピリダジニル基、ピラニル基、テトラヒドロピリジル基、ジヒドロピリダジニル基、パーヒドロアゼピニル基、パーヒドロチアゼピニル基、インドリニル基、イソインドリニル基、インドリル基、インダゾリル基、イソインドリル基、ベンズイミダゾリル基、ベンゾチアゾリル基、ベンゾキサゾリル基、ベンゾジオキソリル基、ベンゾチエニル基、ベンゾフリル基、チエノピリジル基、チアゾロピリジル基、ピロロピリジル基、ジヒドロピロロピリジル基、キノリル基、イソキノリル基、キノキサリニル基、キナゾリニル基、フタラジニル基、シンノリニル基、クロマニル基、イソクロマニル基、ナフチリジニル基、およびこれらの一部又は全部が飽和している環式基から選択される基である、請求項1〜5のいずれか1項記載の化合物。R 2 is a cyclic group which may have the same or different 1 to 3 substituents, and the cyclic group moiety is
Phenyl group, cyclohexyl group, cyclopentyl group, cyclobutyl group, cyclopropyl group, pyrrolidinyl group, imidazolidinyl group, pyrazolidinyl group, oxolanyl group, thioranyl group, pyrrolinyl group, imidazolinyl group, pyrazolinyl group, pyrrolyl group, imidazolyl group, pyrazolyl group , Triazolyl group, tetrazolyl group, furyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, piperidyl group, piperazinyl group, morpholinyl group, thiomorpholinyl group, pyridyl group, pyrimidinyl group, pyrazinyl group Group, pyridazinyl group, pyranyl group, tetrahydropyridyl group, dihydropyridazinyl group, perhydroazepinyl group, perhydrothiazepinyl group, indolinyl group, A soindolinyl group, an indolyl group, an indazolyl group, an isoindolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzoxazolyl group, a benzodioxolyl group, a benzothienyl group, a benzofuryl group, a benzofuryl group, a thienopyridyl group, a thiazolopyridyl group, a pyrrolopyridyl group, a dihydropyrrolopyridyl group A quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a phthalazinyl group, a cinazolinyl group, a chromanyl group, an isochromanyl group, a naphthyridinyl group, and a group selected from a cyclic group in which part or all of them is saturated. The compound according to any one of claims 1 to 5.
A’群置換基:
オキソ基、低級アルカノイル基、低級シクロアルカノイル基、低級アルコキシカルボニル基 および 含窒素脂肪族複素環式基置換カルボニル基。R 2 is a cyclic group which may have the same or different 1 to 3 substituents selected from the following group A ′ substituents, and the cyclic group is a piperidyl group, a piperazinyl group, a morpholinyl group The compound according to any one of claims 1 to 5, which is a group selected from an indolinyl group, an isoindolinyl group and a thiazolopyridyl group.
A 'group substituent:
An oxo group, a lower alkanoyl group, a lower cycloalkanoyl group, a lower alkoxycarbonyl group and a nitrogen-containing aliphatic heterocyclic group-substituted carbonyl group.
(S)−2−シアノ−1−〔t−4−(4−アセチル−1−ピペラジニル)−1−メチル−r−1−シクロヘキシルアミノ〕アセチルピロリジン、
(S)−2−シアノ−1−〔トランス−4−(1,3−ジオキソ−2−イソインドリニル)シクロヘキシルアミノ〕アセチルピロリジン;
(S)−2−シアノ−1−(トランス−4−モルホリノシクロヘキシルアミノ)アセチルピロリジン;および
(S)−2−シアノ−1−〔トランス−4−(チアゾロ[5,4−b]ピリジン−2−イル)シクロヘキシルアミノ〕アセチルピロリジン。The compound selected from the group consisting of: or a pharmaceutically acceptable salt thereof:
(S) -2-Cyano-1- [t-4- (4-acetyl-1-piperazinyl) -1-methyl-r-1-cyclohexylamino] acetylpyrrolidine,
(S) -2-cyano-1- [trans-4- (1,3-dioxo-2-isoindolinyl) cyclohexylamino] acetyl pyrrolidine;
(S) -2-cyano-1- (trans-4-morpholinocyclohexylamino) acetylpyrrolidine; and (S) -2-cyano-1- [trans-4- (thiazolo [5,4-b] pyridine-2 -Yl) cyclohexylamino] acetylpyrrolidine.
で示される化合物と、一般式[III]
B:CH、
R1:H、低級アルキル基、ヒドロキシ低級アルキル基 又は
低級アルコキシ低級アルキル基、
X:単結合手、
R2:以下の(1)および(2)から選択される基;
(1)置換されていてもよい環式基であって該環式基部分が(i)単環もしくは二環式炭化水素基 又は(ii)単環もしくは二環式複素環基 である基; 及び
(2)置換もしくは非置換低級アルキル基から選択される同一又は異なる1〜2個の置換基で置換されたアミノ基〕
で示される化合物又はその塩とを反応させ、所望により生成物を薬理的に許容しうる塩とすることを特徴とする、一般式[I]
で示される脂肪族含窒素五員環化合物又はその薬理的に許容しうる塩の製法。General formula [II]
And a compound represented by the general formula [III]
B: CH ,
R 1 : H, lower alkyl group, hydroxy lower alkyl group or lower alkoxy lower alkyl group,
X: Single bond hand ,
R 2 : a group selected from the following (1) and (2);
(1) a cyclic group which may be substituted, wherein the cyclic group moiety is (i) a monocyclic or bicyclic hydrocarbon group or (ii) a monocyclic or bicyclic heterocyclic group; And (2) an amino group substituted with the same or different 1 to 2 substituents selected from substituted or unsubstituted lower alkyl groups ]
Or a salt thereof, optionally converting the product into a pharmacologically acceptable salt, and reacting the compound with a compound of the general formula [I]
A process for producing an aliphatic nitrogen-containing five-membered ring compound or a pharmacologically acceptable salt thereof
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