JP6404835B2 - ウイルス感染の治療のための2−アミノピリミジン誘導体 - Google Patents
ウイルス感染の治療のための2−アミノピリミジン誘導体 Download PDFInfo
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- JP6404835B2 JP6404835B2 JP2015558440A JP2015558440A JP6404835B2 JP 6404835 B2 JP6404835 B2 JP 6404835B2 JP 2015558440 A JP2015558440 A JP 2015558440A JP 2015558440 A JP2015558440 A JP 2015558440A JP 6404835 B2 JP6404835 B2 JP 6404835B2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
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Description
[式中、
XはS、S=OまたはO=S=Oを表し、
R1は水素、(C1〜6)−アルキル、(C1〜6)−アルコキシまたはアリールであり、
R2は(C1〜3)−アルキルまたは(C3〜6)−シクロアルキルであり、
n=1または2である]
の化合物、またはその薬学的に許容される塩、互変異性体、立体異性体の形態、溶媒和物もしくは多形体を提供する。
全体的なスキーム。化合物Aを、国際公開第2008147697号パンフレットおよび国際公開第2009067081号パンフレットに記載されている手順に従って調製した。
トリエチルアミン(10.5g、103.75mmol、2.4eq.)を、CH2Cl2(200mL)中A(10g、43.23mmol、1eq.)の溶液に0℃で添加した。メタンスルホニルクロリド(6.4g、55.87mmol、1.3eq.)をこの溶液に滴加し、0℃で1.5時間撹拌した。CH2Cl2(500mL)を添加した。溶液をaq.NaHCO3、塩水で洗浄し、Na2SO4で脱水し、固体を濾過により除去し、濾液の溶媒を減圧留去してBを得た。さらなる精製をせずにそのまま使用した。
1H NMR(400MHz,クロロホルム−d)δppm0.70−0.85(m,5H),1.15−1.49(m,13H),1.49−1.61(m,1H),1.61−1.80(m,1H),2.05(s,3H),2.38−2.50(m,2H),3.51(br.s.,1H),4.25(br.s.,1H)
1H NMR(400MHz,クロロホルム−d)δppm1.05−1.15(m,3H),1.40−1.60(m,4H),1.95(m,2H),2.15(m,1H),2.30(d,3H),2.70(t,1H),2.90(t,1H),3.55(m,1H),4.50(m,1H),3.95(s,3H),6.20(d,1H),6.60(br.s.,2H),7.45(s,1H)
LC−MS3.88分
1H NMR(400MHz,メタノール−d4)δppm0.92(t,J=6.9Hz,3H),1.21−1.50(m,4H),1.69(q,J=7.1Hz,2H),1.95−2.28(m,2H),2.98(s,3H),3.09−3.22(m,2H),3.87(s,3H),4.37−4.55(m,1H),7.26(s,1H)不安定なプロトンは観察されなかった。
LC−MS3.78分
1H NMR(400MHz,メタノール−d4)δppm0.90(t,J=6.8Hz,3H),1.19−1.49(m,4H),1.67(d,J=6.5Hz,2H),1.91−2.15(m,2H),2.63(br.s.,3H),2.69−2.96(m,2H),3.85(s,3H),4.46(br.s.,1H),7.25(s,1H)不安定なプロトンは観察されなかった。
生物学的アッセイの説明
TLR7およびTLR8活性の評価
化合物がヒトTLR7および/またはTLR8を活性化する能力を、TLR7またはTLR8発現ベクターおよびNFκB−lucレポーター構築物を一過的にトランスフェクトしたHEK293細胞を使用して、細胞レポーターアッセイで評価した。
PBMCからの調整培地によるインターフェロン刺激応答配列(ISRE)の活性化を測定することにより、化合物のIFN−I誘導能力も評価した。配列GAAACTGAAACTのISRE配列はSTAT1−STAT2−IRF9転写因子に対する応答性が高く、それはIFN−Iがその受容体IFNAR(Clontech、PT3372−5W)に結合すると活性化される。Clontech製のプラスミドpISRE−Luc(ref.631913)は、このISRE配列を5コピー、その後にホタルルシフェラーゼORFを含有する。pISRE−Lucを安定トランスフェクトしたHEK293細胞株(HEK−ISREluc)を、調整PBMC細胞培養培地のプロファイルに合うように樹立した。
[1]
式(I)
XはS、S=OまたはO=S=Oを表し、
R 1 は水素、(C 1 〜 6 )−アルキル、(C 1 〜 6 )−アルコキシまたはアリールであり、
R 2 は(C 1 〜 3 )−アルキルまたは(C 3 〜 6 )−シクロアルキルであり、
n=1または2である]
の化合物、またはその薬学的に許容される塩、互変異性体、立体異性体の形態、溶媒和物もしくは多形体。
[2]
上記[1]に記載の式(I)の化合物またはその薬学的に許容される塩、互変異性体、立体異性体の形態、溶媒和物もしくは多形体を、1種または複数種の薬学的に許容される賦形剤、希釈剤または担体とともに含む医薬組成物。
[3]
薬剤として使用するための、上記[1]に記載の式(I)の化合物またはその薬学的に許容される塩、互変異性体、立体異性体の形態、溶媒和物もしくは多形体、または上記[2]に記載の医薬組成物。
[4]
TLR7および/またはTLR8の調節が関与する疾患の治療に使用するための、上記[1]に記載の式(I)の化合物またはその薬学的に許容される塩、互変異性体、立体異性体の形態、溶媒和物もしくは多形体、または上記[2]に記載の医薬組成物。
Claims (6)
- 式(I)
XはS、S=OまたはO=S=Oを表し、
R1は水素、(C1〜6)−アルキル、(C1〜6)−アルコキシまたはアリールであり、
R2は(C1〜3)−アルキルまたは(C3〜6)−シクロアルキルであり、
n=1または2である]
の化合物、またはその薬学的に許容される塩、互変異性体、立体異性体の形態、溶媒和物もしくは多形体。 - 以下の式:
- 以下の式:
- 請求項1〜3のいずれか一項に記載の化合物またはその薬学的に許容される塩、互変異性体、立体異性体の形態、溶媒和物もしくは多形体を、1種または複数種の薬学的に許容される賦形剤、希釈剤または担体とともに含む医薬組成物。
- 薬剤として使用するための、請求項4に記載の医薬組成物。
- ウイルス感染、免疫疾患または炎症性疾患を治療するための、請求項4に記載の医薬組成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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EP13156167 | 2013-02-21 | ||
EP13156167.2 | 2013-02-21 | ||
PCT/EP2014/053273 WO2014128189A1 (en) | 2013-02-21 | 2014-02-20 | 2-aminopyrimidine derivatives for the treatment of viral infections |
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JP2016509041A JP2016509041A (ja) | 2016-03-24 |
JP6404835B2 true JP6404835B2 (ja) | 2018-10-17 |
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JP2015558440A Active JP6404835B2 (ja) | 2013-02-21 | 2014-02-20 | ウイルス感染の治療のための2−アミノピリミジン誘導体 |
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US (3) | US9598378B2 (ja) |
EP (1) | EP2958900B1 (ja) |
JP (1) | JP6404835B2 (ja) |
KR (2) | KR102300861B1 (ja) |
CN (1) | CN105189468B (ja) |
AU (2) | AU2014220717B2 (ja) |
BR (1) | BR112015020118B1 (ja) |
CA (1) | CA2897587C (ja) |
CL (1) | CL2015002335A1 (ja) |
DK (1) | DK2958900T3 (ja) |
EA (1) | EA035174B1 (ja) |
ES (1) | ES2733361T3 (ja) |
HK (1) | HK1213569A1 (ja) |
IL (1) | IL239859A0 (ja) |
MX (1) | MX367915B (ja) |
MY (1) | MY191389A (ja) |
PH (1) | PH12015501648B1 (ja) |
SG (1) | SG11201506639XA (ja) |
UA (1) | UA118751C2 (ja) |
WO (1) | WO2014128189A1 (ja) |
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