NO331917B1 - Pyrazolopyridinderivater samt anvendelse og fremstilling derav og farmasoytisk preparat - Google Patents
Pyrazolopyridinderivater samt anvendelse og fremstilling derav og farmasoytisk preparat Download PDFInfo
- Publication number
- NO331917B1 NO331917B1 NO20053647A NO20053647A NO331917B1 NO 331917 B1 NO331917 B1 NO 331917B1 NO 20053647 A NO20053647 A NO 20053647A NO 20053647 A NO20053647 A NO 20053647A NO 331917 B1 NO331917 B1 NO 331917B1
- Authority
- NO
- Norway
- Prior art keywords
- pyrazolo
- fluorophenyl
- pyridyl
- bis
- pyridine
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 title description 2
- 150000005229 pyrazolopyridines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 419
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 239000012453 solvate Substances 0.000 claims abstract description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 933
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 464
- 238000000034 method Methods 0.000 claims description 250
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 247
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 168
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 144
- 150000001412 amines Chemical class 0.000 claims description 110
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 110
- 238000006243 chemical reaction Methods 0.000 claims description 83
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 61
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 61
- 125000001424 substituent group Chemical group 0.000 claims description 60
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 52
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 49
- -1 4-piperidyl Chemical group 0.000 claims description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 40
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 150000002367 halogens Chemical class 0.000 claims description 30
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 23
- 150000002576 ketones Chemical class 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 20
- 229920006395 saturated elastomer Polymers 0.000 claims description 20
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 19
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 12
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 12
- 102100040247 Tumor necrosis factor Human genes 0.000 claims description 12
- 229910052705 radium Inorganic materials 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 11
- GVLRTOYGRNLSDW-UHFFFAOYSA-N 1h-pyrazolo[3,4-b]pyridine Chemical compound C1=CC=C2C=NNC2=N1 GVLRTOYGRNLSDW-UHFFFAOYSA-N 0.000 claims description 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
- QWOODJDZURZLML-UHFFFAOYSA-N 4,6-bis(4-fluorophenyl)-5-pyridin-4-yl-1h-pyrazolo[3,4-b]pyridine Chemical compound C1=CC(F)=CC=C1C(C(=C1C=2C=CC(F)=CC=2)C=2C=CN=CC=2)=NC2=C1C=NN2 QWOODJDZURZLML-UHFFFAOYSA-N 0.000 claims description 9
- DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 claims description 9
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 9
- 239000000654 additive Substances 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 235000019260 propionic acid Nutrition 0.000 claims description 9
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 9
- 229910052702 rhenium Inorganic materials 0.000 claims description 9
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 claims description 8
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- 239000003814 drug Substances 0.000 claims description 8
- 230000001404 mediated effect Effects 0.000 claims description 8
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- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 claims description 7
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- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 108010002352 Interleukin-1 Proteins 0.000 claims description 6
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- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 208000023275 Autoimmune disease Diseases 0.000 claims description 5
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- 150000001299 aldehydes Chemical class 0.000 claims description 5
- 208000027866 inflammatory disease Diseases 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 230000004770 neurodegeneration Effects 0.000 claims description 5
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 5
- MAEDTKUUFDDTCG-UHFFFAOYSA-N 2-ethyl-4,6-bis(4-fluorophenyl)-5-pyridin-4-ylpyrazolo[3,4-b]pyridine Chemical group C=1C=NC=CC=1C=1C(C=2C=CC(F)=CC=2)=NC2=NN(CC)C=C2C=1C1=CC=C(F)C=C1 MAEDTKUUFDDTCG-UHFFFAOYSA-N 0.000 claims description 4
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES200300640A ES2214150B1 (es) | 2003-02-27 | 2003-02-27 | "nuevos derivados de pirazolopiridinas". |
ES200300727A ES2214976B1 (es) | 2003-03-14 | 2003-03-14 | "nuevos derivados de pirazolopiridinas". |
ES200302504 | 2003-10-27 | ||
PCT/EP2004/001974 WO2004076450A1 (en) | 2003-02-27 | 2004-02-27 | Pyrazolopyridine derivates |
Publications (3)
Publication Number | Publication Date |
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NO20053647D0 NO20053647D0 (no) | 2005-07-27 |
NO20053647L NO20053647L (no) | 2005-10-18 |
NO331917B1 true NO331917B1 (no) | 2012-04-30 |
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NO20053647A NO331917B1 (no) | 2003-02-27 | 2005-07-27 | Pyrazolopyridinderivater samt anvendelse og fremstilling derav og farmasoytisk preparat |
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US (3) | US7468376B2 (ja) |
EP (1) | EP1611131B1 (ja) |
JP (1) | JP4814783B2 (ja) |
KR (1) | KR101312736B1 (ja) |
AR (1) | AR043416A1 (ja) |
AT (1) | ATE481402T1 (ja) |
AU (1) | AU2004215644B2 (ja) |
BR (1) | BRPI0407811A (ja) |
CA (1) | CA2515197C (ja) |
CL (1) | CL2004000398A1 (ja) |
CY (1) | CY1111544T1 (ja) |
DE (1) | DE602004029145D1 (ja) |
DK (1) | DK1611131T3 (ja) |
EC (2) | ECSP056041A (ja) |
HK (1) | HK1085214A1 (ja) |
HR (1) | HRP20050682B1 (ja) |
IL (1) | IL196021A (ja) |
IS (1) | IS2875B (ja) |
MX (1) | MXPA05009069A (ja) |
NO (1) | NO331917B1 (ja) |
NZ (1) | NZ541836A (ja) |
PE (1) | PE20050521A1 (ja) |
PL (1) | PL378296A1 (ja) |
PT (1) | PT1611131E (ja) |
RS (1) | RS51768B (ja) |
RU (1) | RU2359971C2 (ja) |
SI (1) | SI1611131T1 (ja) |
TW (1) | TWI325865B (ja) |
UA (1) | UA81453C2 (ja) |
WO (1) | WO2004076450A1 (ja) |
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