ZA200603582B - Bicyclic pyrazolone cytokine inhibitors - Google Patents
Bicyclic pyrazolone cytokine inhibitors Download PDFInfo
- Publication number
- ZA200603582B ZA200603582B ZA200603582A ZA200603582A ZA200603582B ZA 200603582 B ZA200603582 B ZA 200603582B ZA 200603582 A ZA200603582 A ZA 200603582A ZA 200603582 A ZA200603582 A ZA 200603582A ZA 200603582 B ZA200603582 B ZA 200603582B
- Authority
- ZA
- South Africa
- Prior art keywords
- substituted
- unsubstituted
- hydrogen
- alkyl
- methyl
- Prior art date
Links
- 102000004127 Cytokines Human genes 0.000 title claims description 19
- 108090000695 Cytokines Proteins 0.000 title claims description 19
- 125000002619 bicyclic group Chemical group 0.000 title description 6
- 239000003112 inhibitor Substances 0.000 title description 4
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 81
- 239000001257 hydrogen Substances 0.000 claims description 81
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 150000001875 compounds Chemical class 0.000 claims description 59
- -1 pyran-4-ylamino, piperidin—4-ylamino, pyridin-2-ylamino Chemical group 0.000 claims description 59
- 125000003118 aryl group Chemical group 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 48
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims description 39
- 150000002431 hydrogen Chemical class 0.000 claims description 37
- 125000000623 heterocyclic group Chemical group 0.000 claims description 36
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 125000002837 carbocyclic group Chemical group 0.000 claims description 26
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
- 125000004429 atom Chemical group 0.000 claims description 17
- 201000010099 disease Diseases 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 150000001768 cations Chemical class 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 241000124008 Mammalia Species 0.000 claims description 11
- 230000002757 inflammatory effect Effects 0.000 claims description 11
- 125000005275 alkylenearyl group Chemical group 0.000 claims description 10
- 125000005218 alkyleneheteroaryl group Chemical group 0.000 claims description 10
- 241000282412 Homo Species 0.000 claims description 8
- 125000005647 linker group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims description 2
- 206010006895 Cachexia Diseases 0.000 claims description 2
- 206010040070 Septic Shock Diseases 0.000 claims description 2
- 102100040247 Tumor necrosis factor Human genes 0.000 claims description 2
- 206010054094 Tumour necrosis Diseases 0.000 claims description 2
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
- 230000036303 septic shock Effects 0.000 claims description 2
- 208000024891 symptom Diseases 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 2
- 102100033668 Cartilage matrix protein Human genes 0.000 claims 3
- 101001018382 Homo sapiens Cartilage matrix protein Proteins 0.000 claims 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 claims 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 2
- KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-UHFFFAOYSA-N 0.000 claims 1
- NXMXETCTWNXSFG-BYPYZUCNSA-N (2s)-1-methoxypropan-2-amine Chemical compound COC[C@H](C)N NXMXETCTWNXSFG-BYPYZUCNSA-N 0.000 claims 1
- OVKDLPZRDQTOJW-BYPYZUCNSA-N (3s)-3-amino-2-methylbutan-2-ol Chemical compound C[C@H](N)C(C)(C)O OVKDLPZRDQTOJW-BYPYZUCNSA-N 0.000 claims 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- FFODYNVSVFUWQQ-UHFFFAOYSA-N 6-(2-chlorobenzoyl)-7-(2-phenoxypyrimidin-4-yl)-2,3-dihydro-1h-pyrazolo[1,2-a]pyrazol-5-one Chemical compound ClC1=CC=CC=C1C(=O)C(C(N1CCCN11)=O)=C1C1=CC=NC(OC=2C=CC=CC=2)=N1 FFODYNVSVFUWQQ-UHFFFAOYSA-N 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010006550 Bulimia nervosa Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 201000005569 Gout Diseases 0.000 claims 1
- 206010019233 Headaches Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 108090001005 Interleukin-6 Proteins 0.000 claims 1
- 108090001007 Interleukin-8 Proteins 0.000 claims 1
- 206010028289 Muscle atrophy Diseases 0.000 claims 1
- 206010037660 Pyrexia Diseases 0.000 claims 1
- 206010038687 Respiratory distress Diseases 0.000 claims 1
- HYSOPXHRAHXSFM-MRVPVSSYSA-N [(1s)-1-methylcyclohexa-2,4-dien-1-yl]methanamine Chemical compound NC[C@@]1(C)CC=CC=C1 HYSOPXHRAHXSFM-MRVPVSSYSA-N 0.000 claims 1
- 208000022531 anorexia Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 206010061428 decreased appetite Diseases 0.000 claims 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 1
- 231100000869 headache Toxicity 0.000 claims 1
- 206010025482 malaise Diseases 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 230000036470 plasma concentration Effects 0.000 claims 1
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims 1
- 239000004576 sand Substances 0.000 claims 1
- 201000004595 synovitis Diseases 0.000 claims 1
- 201000008827 tuberculosis Diseases 0.000 claims 1
- 235000013350 formula milk Nutrition 0.000 description 25
- 150000001412 amines Chemical group 0.000 description 9
- 150000002170 ethers Chemical class 0.000 description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 102000000589 Interleukin-1 Human genes 0.000 description 5
- 108010002352 Interleukin-1 Proteins 0.000 description 5
- 230000001276 controlling effect Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000002015 acyclic group Chemical group 0.000 description 4
- 125000001033 ether group Chemical group 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 102000003390 tumor necrosis factor Human genes 0.000 description 3
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 241000725303 Human immunodeficiency virus Species 0.000 description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001207 fluorophenyl group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 201000008482 osteoarthritis Diseases 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- ZCZVGQCBSJLDDS-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,8-naphthyridine Chemical compound C1=CC=C2CCCNC2=N1 ZCZVGQCBSJLDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- 125000003974 3-carbamimidamidopropyl group Chemical group C(N)(=N)NCCC* 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241001358212 Calia Species 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 206010028851 Necrosis Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000002612 cardiopulmonary effect Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012678 infectious agent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 125000005646 oximino group Chemical group 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- 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]
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Pulmonology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Oncology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Communicable Diseases (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51888603P | 2003-11-10 | 2003-11-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200603582B true ZA200603582B (en) | 2007-04-25 |
Family
ID=34590314
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200603582A ZA200603582B (en) | 2003-11-10 | 2006-05-05 | Bicyclic pyrazolone cytokine inhibitors |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US7482356B2 (pt) |
| EP (1) | EP1682551A2 (pt) |
| JP (1) | JP2007510739A (pt) |
| KR (1) | KR100835152B1 (pt) |
| CN (1) | CN1878772A (pt) |
| AR (1) | AR046618A1 (pt) |
| AU (1) | AU2004289691B2 (pt) |
| BR (1) | BRPI0416358A (pt) |
| CA (1) | CA2545781A1 (pt) |
| IL (1) | IL175151A0 (pt) |
| MA (1) | MA28154A1 (pt) |
| NO (1) | NO20062639L (pt) |
| PE (1) | PE20050578A1 (pt) |
| RU (1) | RU2358976C2 (pt) |
| SG (1) | SG147476A1 (pt) |
| TW (1) | TW200518754A (pt) |
| WO (1) | WO2005047287A2 (pt) |
| ZA (1) | ZA200603582B (pt) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101182114B1 (ko) * | 2010-03-05 | 2012-09-12 | 한림제약(주) | 유효성분으로서 레바미피드를 함유하는 골관절염 예방 또는 치료용 약학 조성물 |
| TWI800498B (zh) * | 2016-12-21 | 2023-05-01 | 義大利商吉斯藥品公司 | 作為Rho-激酶抑制劑之雙環二氫嘧啶-羧醯胺衍生物 |
| CN115286635B (zh) * | 2022-08-22 | 2023-10-24 | 河南师范大学 | 一种手性并环吡唑啉酮类化合物的合成方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1124982A (en) | 1965-02-09 | 1968-08-21 | Lepetit Spa | Diazabicyclo octanes and derivatives thereof |
| CH529154A (fr) | 1969-10-27 | 1972-10-15 | Lepetit Spa | Procédé de préparation de pyrazolo (1,2-b) phtalazine-1,5 (10H)-diones |
| US6472416B1 (en) | 1999-08-27 | 2002-10-29 | Abbott Laboratories | Sulfonylphenylpyrazole compounds useful as COX-2 inhibitors |
| US6849627B2 (en) * | 2001-09-20 | 2005-02-01 | The Procter & Gamble Company | 6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-ones which control inflammatory cytokines |
| US6730668B2 (en) * | 2001-09-20 | 2004-05-04 | The Procter & Gamble Company | 6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-ones which control inflammatory cytokines |
| US7087615B2 (en) * | 2001-09-20 | 2006-08-08 | The Procter & Gamble Company | 6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-ones which provide analgesia |
| US6566357B1 (en) * | 2001-09-20 | 2003-05-20 | The Procter & Gamble Co. | Spirocyclic-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-ones which control inflammatory cytokines |
| US6677337B2 (en) | 2002-03-19 | 2004-01-13 | The Procter & Gamble Company | 1,2-dihydropyrazol-3-ones which controls inflammatory cytokines |
-
2004
- 2004-11-05 US US10/983,114 patent/US7482356B2/en not_active Expired - Fee Related
- 2004-11-09 SG SG200808004-6A patent/SG147476A1/en unknown
- 2004-11-09 AR ARP040104133A patent/AR046618A1/es not_active Application Discontinuation
- 2004-11-09 RU RU2006114580/04A patent/RU2358976C2/ru not_active IP Right Cessation
- 2004-11-09 EP EP04810572A patent/EP1682551A2/en not_active Withdrawn
- 2004-11-09 BR BRPI0416358-3A patent/BRPI0416358A/pt not_active IP Right Cessation
- 2004-11-09 KR KR1020067008849A patent/KR100835152B1/ko not_active IP Right Cessation
- 2004-11-09 JP JP2006539725A patent/JP2007510739A/ja active Pending
- 2004-11-09 CA CA002545781A patent/CA2545781A1/en not_active Abandoned
- 2004-11-09 WO PCT/US2004/037264 patent/WO2005047287A2/en active Application Filing
- 2004-11-09 CN CNA2004800328398A patent/CN1878772A/zh active Pending
- 2004-11-09 AU AU2004289691A patent/AU2004289691B2/en not_active Expired - Fee Related
- 2004-11-09 PE PE2004001091A patent/PE20050578A1/es not_active Application Discontinuation
- 2004-11-10 TW TW093134336A patent/TW200518754A/zh unknown
-
2006
- 2006-04-24 IL IL175151A patent/IL175151A0/en unknown
- 2006-05-05 ZA ZA200603582A patent/ZA200603582B/en unknown
- 2006-05-11 MA MA29018A patent/MA28154A1/fr unknown
- 2006-06-08 NO NO20062639A patent/NO20062639L/no not_active Application Discontinuation
-
2008
- 2008-11-06 US US12/291,084 patent/US20090069355A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20090069355A1 (en) | 2009-03-12 |
| SG147476A1 (en) | 2008-11-28 |
| AU2004289691B2 (en) | 2009-04-23 |
| WO2005047287A2 (en) | 2005-05-26 |
| AU2004289691A1 (en) | 2005-05-26 |
| BRPI0416358A (pt) | 2007-05-08 |
| AR046618A1 (es) | 2005-12-14 |
| TW200518754A (en) | 2005-06-16 |
| CA2545781A1 (en) | 2005-05-26 |
| RU2006114580A (ru) | 2007-12-20 |
| RU2358976C2 (ru) | 2009-06-20 |
| US7482356B2 (en) | 2009-01-27 |
| NO20062639L (no) | 2006-06-08 |
| KR100835152B1 (ko) | 2008-06-09 |
| PE20050578A1 (es) | 2005-09-26 |
| KR20060086391A (ko) | 2006-07-31 |
| CN1878772A (zh) | 2006-12-13 |
| US20050113392A1 (en) | 2005-05-26 |
| EP1682551A2 (en) | 2006-07-26 |
| MA28154A1 (fr) | 2006-09-01 |
| IL175151A0 (en) | 2006-09-05 |
| WO2005047287A3 (en) | 2005-07-28 |
| JP2007510739A (ja) | 2007-04-26 |
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