JP2006520373A - 炎症の治療に有用なピラゾール化合物 - Google Patents
炎症の治療に有用なピラゾール化合物 Download PDFInfo
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- JP2006520373A JP2006520373A JP2006505952A JP2006505952A JP2006520373A JP 2006520373 A JP2006520373 A JP 2006520373A JP 2006505952 A JP2006505952 A JP 2006505952A JP 2006505952 A JP2006505952 A JP 2006505952A JP 2006520373 A JP2006520373 A JP 2006520373A
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- 238000011282 treatment Methods 0.000 title claims abstract description 24
- 206010061218 Inflammation Diseases 0.000 title claims abstract description 22
- 230000004054 inflammatory process Effects 0.000 title claims abstract description 22
- 150000003217 pyrazoles Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 285
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- 230000000694 effects Effects 0.000 claims abstract description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 15
- 102000009515 Arachidonate 15-Lipoxygenase Human genes 0.000 claims abstract description 14
- 108010048907 Arachidonate 15-lipoxygenase Proteins 0.000 claims abstract description 14
- 201000010099 disease Diseases 0.000 claims abstract description 14
- 102000003820 Lipoxygenases Human genes 0.000 claims abstract description 12
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- 230000005764 inhibitory process Effects 0.000 claims abstract description 8
- -1 2-thiazolyl Chemical group 0.000 claims description 276
- 125000000217 alkyl group Chemical group 0.000 claims description 81
- 125000005843 halogen group Chemical group 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 62
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 39
- 125000001424 substituent group Chemical group 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 34
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- 125000001153 fluoro group Chemical group F* 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
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- 239000003814 drug Substances 0.000 claims description 20
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 20
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 19
- 125000004429 atom Chemical group 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 208000024891 symptom Diseases 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 12
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 11
- 125000003386 piperidinyl group Chemical group 0.000 claims description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 10
- 239000002671 adjuvant Substances 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 10
- 125000004193 piperazinyl group Chemical group 0.000 claims description 10
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
- 208000006673 asthma Diseases 0.000 claims description 9
- 229940124597 therapeutic agent Drugs 0.000 claims description 9
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 8
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 8
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 7
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 208000027866 inflammatory disease Diseases 0.000 claims description 7
- 230000002757 inflammatory effect Effects 0.000 claims description 7
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 7
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 5
- 201000004624 Dermatitis Diseases 0.000 claims description 5
- 206010037660 Pyrexia Diseases 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 208000010668 atopic eczema Diseases 0.000 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 5
- 238000009472 formulation Methods 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 5
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 4
- 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
- 206010065390 Inflammatory pain Diseases 0.000 claims description 4
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- 238000004519 manufacturing process Methods 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000006850 spacer group Chemical group 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 206010010741 Conjunctivitis Diseases 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
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- 229910052802 copper Inorganic materials 0.000 claims description 3
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 3
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
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- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 3
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- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
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- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 claims description 2
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- 210000001519 tissue Anatomy 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000005455 trithianyl group Chemical group 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
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- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0300705A SE0300705D0 (sv) | 2003-03-14 | 2003-03-14 | New compounds |
| US48256303P | 2003-06-26 | 2003-06-26 | |
| PCT/GB2004/001054 WO2004080999A1 (en) | 2003-03-14 | 2004-03-12 | Pyrazole compounds useful in the treatment of inflammation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006520373A true JP2006520373A (ja) | 2006-09-07 |
| JP2006520373A5 JP2006520373A5 (enExample) | 2007-04-19 |
Family
ID=32993214
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006505952A Withdrawn JP2006520373A (ja) | 2003-03-14 | 2004-03-12 | 炎症の治療に有用なピラゾール化合物 |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP1603897A1 (enExample) |
| JP (1) | JP2006520373A (enExample) |
| WO (1) | WO2004080999A1 (enExample) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010536926A (ja) * | 2007-08-27 | 2010-12-02 | ビーエーエスエフ ソシエタス・ヨーロピア | 無脊椎動物系害虫を防除するためのピラゾール化合物 |
| US8710056B2 (en) | 2009-07-06 | 2014-04-29 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
| US8729083B2 (en) | 2008-09-24 | 2014-05-20 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
| US9029639B2 (en) | 2009-07-06 | 2015-05-12 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
| US9125414B2 (en) | 2009-07-24 | 2015-09-08 | Basf Se | Pyridine derivatives compounds for controlling invertebrate pests |
| CN110678456A (zh) * | 2017-05-23 | 2020-01-10 | 隆德贝克拉荷亚研究中心有限公司 | 吡唑magl抑制剂 |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008513426A (ja) * | 2004-09-20 | 2008-05-01 | バイオリポックス エービー | 炎症の治療に有用なピラゾール化合物 |
| EP1794130A1 (en) * | 2004-09-20 | 2007-06-13 | Biolipox AB | Pyrazole compounds useful in the treatment of inflammation |
| CA2620899A1 (en) * | 2005-10-12 | 2007-04-19 | Biolipox Ab | Benzoxazoles useful in the treatment of inflammation |
| WO2007042817A1 (en) * | 2005-10-13 | 2007-04-19 | Biolipox Ab | Naphthalene-disulfonamides useful for the treatment of inflammation |
| TW200800911A (en) * | 2005-10-20 | 2008-01-01 | Biolipox Ab | Pyrazoles useful in the treatment of inflammation |
| EP1943234A1 (en) * | 2005-10-31 | 2008-07-16 | Biolipox AB | Triazole compounds as lipoxygenase inhibitors |
| TW200732320A (en) * | 2005-10-31 | 2007-09-01 | Biolipox Ab | Pyrazoles useful in the treatment of inflammation |
| WO2007052000A1 (en) * | 2005-11-01 | 2007-05-10 | Biolipox Ab | Pyrazoles useful in the treatment of inflammation |
| WO2008001079A1 (en) * | 2006-06-27 | 2008-01-03 | Biolipox Ab | Methods for identifying modulators of eoxin formation |
| WO2008129276A1 (en) * | 2007-04-19 | 2008-10-30 | Boehringer Ingelheim International Gmbh | Disulfonamides useful in the treatment of inflammation |
| WO2008129280A1 (en) * | 2007-04-20 | 2008-10-30 | Biolipox Ab | Pyrazoles useful in the treatment of inflammation |
| CA2684105C (en) | 2007-05-03 | 2011-09-06 | Pfizer Limited | Pyridine derivatives |
| WO2008135767A1 (en) * | 2007-05-07 | 2008-11-13 | Biolipox Ab | New triazole compounds useful in the treatment of inflammation |
| CN102223798A (zh) | 2008-09-24 | 2011-10-19 | 巴斯夫欧洲公司 | 用于防治无脊椎动物害虫的吡唑化合物 |
| WO2012031383A1 (zh) * | 2010-09-06 | 2012-03-15 | 中国科学院广州生物医药与健康研究院 | 酰胺类化合物 |
| WO2021072487A1 (en) * | 2019-10-15 | 2021-04-22 | TroBio Therapeutics Pty Ltd | Sulfonamide compounds and the use thereof in the treatment of cancer |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AUPP042397A0 (en) * | 1997-11-18 | 1997-12-11 | Fujisawa Pharmaceutical Co., Ltd. | 5-arylpyrazole compounds |
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2004
- 2004-03-12 WO PCT/GB2004/001054 patent/WO2004080999A1/en not_active Ceased
- 2004-03-12 JP JP2006505952A patent/JP2006520373A/ja not_active Withdrawn
- 2004-03-12 EP EP04720088A patent/EP1603897A1/en not_active Withdrawn
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010536926A (ja) * | 2007-08-27 | 2010-12-02 | ビーエーエスエフ ソシエタス・ヨーロピア | 無脊椎動物系害虫を防除するためのピラゾール化合物 |
| US8642597B2 (en) | 2007-08-27 | 2014-02-04 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
| US9204647B2 (en) | 2007-08-27 | 2015-12-08 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
| US8729083B2 (en) | 2008-09-24 | 2014-05-20 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
| US9375008B2 (en) | 2008-09-24 | 2016-06-28 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
| US8710056B2 (en) | 2009-07-06 | 2014-04-29 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
| US9029639B2 (en) | 2009-07-06 | 2015-05-12 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
| US9125414B2 (en) | 2009-07-24 | 2015-09-08 | Basf Se | Pyridine derivatives compounds for controlling invertebrate pests |
| CN110678456A (zh) * | 2017-05-23 | 2020-01-10 | 隆德贝克拉荷亚研究中心有限公司 | 吡唑magl抑制剂 |
| CN110678456B (zh) * | 2017-05-23 | 2023-05-02 | H.隆德贝克有限公司 | 吡唑magl抑制剂 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1603897A1 (en) | 2005-12-14 |
| WO2004080999A1 (en) | 2004-09-23 |
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