NO318786B1 - Pyrrolo(2,3-d)pyrimidinforbindelser samt anvendelse derav og farmasoytisk sammensetning - Google Patents
Pyrrolo(2,3-d)pyrimidinforbindelser samt anvendelse derav og farmasoytisk sammensetning Download PDFInfo
- Publication number
- NO318786B1 NO318786B1 NO20006454A NO20006454A NO318786B1 NO 318786 B1 NO318786 B1 NO 318786B1 NO 20006454 A NO20006454 A NO 20006454A NO 20006454 A NO20006454 A NO 20006454A NO 318786 B1 NO318786 B1 NO 318786B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- pyrrolo
- piperidin
- pyrimidine
- lrms
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 150000004943 pyrrolo[2,3-d]pyrimidines Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 88
- 150000003839 salts Chemical class 0.000 claims description 35
- -1 hydroxy, carboxy Chemical group 0.000 claims description 27
- 108010019421 Janus Kinase 3 Proteins 0.000 claims description 25
- 102000006500 Janus Kinase 3 Human genes 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
- 241000124008 Mammalia Species 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 8
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 210000000987 immune system Anatomy 0.000 claims description 8
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 6
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
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- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 5
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- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 5
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
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- 239000003937 drug carrier Substances 0.000 claims description 3
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 2
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- BHEXESBBAOCUEW-UHFFFAOYSA-N 4-(3,3-dimethylpiperidin-1-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1C(C)(C)CCCN1C1=NC=NC2=C1C=CN2 BHEXESBBAOCUEW-UHFFFAOYSA-N 0.000 claims description 2
- XMDULOSPOORHTJ-UHFFFAOYSA-N 5-(2-methylpyridin-4-yl)-4-piperidin-1-yl-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1=NC(C)=CC(C=2C3=C(N4CCCCC4)N=CN=C3NC=2)=C1 XMDULOSPOORHTJ-UHFFFAOYSA-N 0.000 claims description 2
- LWQNDUSDVLVELT-UHFFFAOYSA-N 5-(3-methylimidazol-4-yl)-4-piperidin-1-yl-7h-pyrrolo[2,3-d]pyrimidine Chemical compound CN1C=NC=C1C1=CNC2=NC=NC(N3CCCCC3)=C12 LWQNDUSDVLVELT-UHFFFAOYSA-N 0.000 claims description 2
- WZFLNSVJMWZIGG-UHFFFAOYSA-N 5-(3-methylphenyl)-4-piperidin-1-yl-7h-pyrrolo[2,3-d]pyrimidine Chemical compound CC1=CC=CC(C=2C3=C(N4CCCCC4)N=CN=C3NC=2)=C1 WZFLNSVJMWZIGG-UHFFFAOYSA-N 0.000 claims description 2
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- CIPYWMYUPREAMJ-UHFFFAOYSA-N 5-ethynyl-4-piperidin-1-yl-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C=12C(C#C)=CNC2=NC=NC=1N1CCCCC1 CIPYWMYUPREAMJ-UHFFFAOYSA-N 0.000 claims description 2
- LCTMPEQAHUTSGO-UHFFFAOYSA-N 5-fluoro-4-piperidin-1-yl-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C=12C(F)=CNC2=NC=NC=1N1CCCCC1 LCTMPEQAHUTSGO-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
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- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 2
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 2
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- GUWZKQIDHRZALH-UHFFFAOYSA-N 5-(1-methylimidazol-4-yl)-4-piperidin-1-yl-7h-pyrrolo[2,3-d]pyrimidine Chemical compound CN1C=NC(C=2C3=C(N4CCCCC4)N=CN=C3NC=2)=C1 GUWZKQIDHRZALH-UHFFFAOYSA-N 0.000 claims 1
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000002585 base Substances 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
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Classifications
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Landscapes
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- Pain & Pain Management (AREA)
- Emergency Medicine (AREA)
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US8988698P | 1998-06-19 | 1998-06-19 | |
PCT/IB1999/001110 WO1999065909A1 (en) | 1998-06-19 | 1999-06-14 | PYRROLO[2,3-d]PYRIMIDINE COMPOUNDS |
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