UA76461C2 - Pyrrazole derivatives as pharmaceutical agents, use thereof, a pharmaceutical composition on their basis - Google Patents
Pyrrazole derivatives as pharmaceutical agents, use thereof, a pharmaceutical composition on their basis Download PDFInfo
- Publication number
- UA76461C2 UA76461C2 UA20031110606A UA20031110606A UA76461C2 UA 76461 C2 UA76461 C2 UA 76461C2 UA 20031110606 A UA20031110606 A UA 20031110606A UA 20031110606 A UA20031110606 A UA 20031110606A UA 76461 C2 UA76461 C2 UA 76461C2
- Authority
- UA
- Ukraine
- Prior art keywords
- dihydro
- pyrrolo
- pyridin
- pyrazol
- quinoline
- Prior art date
Links
- 239000008177 pharmaceutical agent Substances 0.000 title abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 abstract description 294
- 229920006395 saturated elastomer Polymers 0.000 abstract description 31
- 229910052799 carbon Inorganic materials 0.000 abstract description 25
- 229910052717 sulfur Inorganic materials 0.000 abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 abstract description 4
- 239000003112 inhibitor Substances 0.000 abstract description 3
- 230000019491 signal transduction Effects 0.000 abstract 1
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 description 515
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 261
- -1 acetamido- Chemical class 0.000 description 236
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 236
- 239000000203 mixture Substances 0.000 description 228
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 198
- 239000000243 solution Substances 0.000 description 165
- 229910052739 hydrogen Inorganic materials 0.000 description 131
- 239000001257 hydrogen Substances 0.000 description 126
- 125000000217 alkyl group Chemical group 0.000 description 120
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 104
- 230000015572 biosynthetic process Effects 0.000 description 101
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 98
- 239000002253 acid Substances 0.000 description 97
- 238000003786 synthesis reaction Methods 0.000 description 95
- 238000000034 method Methods 0.000 description 89
- 238000006243 chemical reaction Methods 0.000 description 77
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 75
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 73
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
- 229940093499 ethyl acetate Drugs 0.000 description 67
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
- 235000019439 ethyl acetate Nutrition 0.000 description 66
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 63
- 239000007787 solid Substances 0.000 description 63
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 58
- 239000000047 product Substances 0.000 description 58
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 51
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- 239000003480 eluent Substances 0.000 description 41
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- 238000003756 stirring Methods 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 37
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- 125000003118 aryl group Chemical group 0.000 description 35
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- 125000001424 substituent group Chemical class 0.000 description 27
- 125000003710 aryl alkyl group Chemical group 0.000 description 26
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 26
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 23
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- 238000010992 reflux Methods 0.000 description 22
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- 238000002360 preparation method Methods 0.000 description 20
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- 125000003282 alkyl amino group Chemical group 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 19
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 18
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- 238000010828 elution Methods 0.000 description 17
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- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 16
- 125000004076 pyridyl group Chemical group 0.000 description 16
- 102100033891 Arylsulfatase I Human genes 0.000 description 15
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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| US29346401P | 2001-05-24 | 2001-05-24 | |
| PCT/US2002/011884 WO2002094833A1 (en) | 2001-05-24 | 2002-05-13 | Novel pyrrole derivatives as pharmaceutical agents |
Publications (1)
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| UA76461C2 true UA76461C2 (en) | 2006-08-15 |
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| UA20031110606A UA76461C2 (en) | 2001-05-24 | 2002-05-13 | Pyrrazole derivatives as pharmaceutical agents, use thereof, a pharmaceutical composition on their basis |
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| AU2003290734A1 (en) * | 2002-11-27 | 2004-06-23 | Eli Lilly And Company | Novel compounds as pharmaceutical agents |
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| US7511065B2 (en) * | 2003-11-12 | 2009-03-31 | Eli Lilly And Company | Mixed lineage kinase modulators |
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