JP2007509114A5 - - Google Patents
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- Publication number
- JP2007509114A5 JP2007509114A5 JP2006536158A JP2006536158A JP2007509114A5 JP 2007509114 A5 JP2007509114 A5 JP 2007509114A5 JP 2006536158 A JP2006536158 A JP 2006536158A JP 2006536158 A JP2006536158 A JP 2006536158A JP 2007509114 A5 JP2007509114 A5 JP 2007509114A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- fluoro
- indol
- acetic acid
- solvate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000003814 drug Substances 0.000 claims description 10
- 102000009389 Prostaglandin D receptors Human genes 0.000 claims description 7
- 108050000258 Prostaglandin D receptors Proteins 0.000 claims description 7
- 239000005557 antagonist Substances 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- -1 chloro, fluoro, methyl Chemical group 0.000 claims description 5
- 102000005962 receptors Human genes 0.000 claims description 5
- 108020003175 receptors Proteins 0.000 claims description 5
- 102100031111 Disintegrin and metalloproteinase domain-containing protein 17 Human genes 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 108091007505 ADAM17 Proteins 0.000 claims description 2
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 claims description 2
- 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 claims description 2
- 108090000978 Interleukin-4 Proteins 0.000 claims description 2
- 108010002616 Interleukin-5 Proteins 0.000 claims description 2
- 230000000903 blocking effect Effects 0.000 claims description 2
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 claims description 2
- BFPSDSIWYFKGBC-UHFFFAOYSA-N chlorotrianisene Chemical compound C1=CC(OC)=CC=C1C(Cl)=C(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 BFPSDSIWYFKGBC-UHFFFAOYSA-N 0.000 claims description 2
- 230000016396 cytokine production Effects 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 239000002571 phosphodiesterase inhibitor Substances 0.000 claims description 2
- MWLSOWXNZPKENC-SSDOTTSWSA-N zileuton Chemical compound C1=CC=C2SC([C@H](N(O)C(N)=O)C)=CC2=C1 MWLSOWXNZPKENC-SSDOTTSWSA-N 0.000 claims description 2
- 229960005332 zileuton Drugs 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 25
- 239000012453 solvate Substances 0.000 claims 24
- 150000003839 salts Chemical class 0.000 claims 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 208000010247 contact dermatitis Diseases 0.000 claims 6
- 230000001404 mediated effect Effects 0.000 claims 6
- 206010012438 Dermatitis atopic Diseases 0.000 claims 5
- 201000008937 atopic dermatitis Diseases 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 239000013543 active substance Substances 0.000 claims 4
- 230000006806 disease prevention Effects 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 208000002874 Acne Vulgaris Diseases 0.000 claims 3
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 claims 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims 3
- 206010010741 Conjunctivitis Diseases 0.000 claims 3
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 3
- 208000011231 Crohn disease Diseases 0.000 claims 3
- 206010012442 Dermatitis contact Diseases 0.000 claims 3
- 206010065563 Eosinophilic bronchitis Diseases 0.000 claims 3
- 208000004262 Food Hypersensitivity Diseases 0.000 claims 3
- 206010016946 Food allergy Diseases 0.000 claims 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 3
- 201000004681 Psoriasis Diseases 0.000 claims 3
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims 3
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims 3
- 206010063837 Reperfusion injury Diseases 0.000 claims 3
- 206010039094 Rhinitis perennial Diseases 0.000 claims 3
- 208000036284 Rhinitis seasonal Diseases 0.000 claims 3
- 206010000496 acne Diseases 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 201000009961 allergic asthma Diseases 0.000 claims 3
- 208000002205 allergic conjunctivitis Diseases 0.000 claims 3
- 201000010105 allergic rhinitis Diseases 0.000 claims 3
- 208000006673 asthma Diseases 0.000 claims 3
- 208000024998 atopic conjunctivitis Diseases 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 201000001564 eosinophilic gastroenteritis Diseases 0.000 claims 3
- 230000002349 favourable effect Effects 0.000 claims 3
- 235000020932 food allergy Nutrition 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 208000008585 mastocytosis Diseases 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 201000006417 multiple sclerosis Diseases 0.000 claims 3
- 201000008482 osteoarthritis Diseases 0.000 claims 3
- 208000022719 perennial allergic rhinitis Diseases 0.000 claims 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 3
- 208000017022 seasonal allergic rhinitis Diseases 0.000 claims 3
- 208000011580 syndromic disease Diseases 0.000 claims 3
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 3
- FATGTHLOZSXOBC-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-(quinolin-2-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=CC=C2)C2=N1 FATGTHLOZSXOBC-UHFFFAOYSA-N 0.000 claims 2
- VURBJTJUNFTLRH-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(4-methylsulfonylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(S(C)(=O)=O)C=C1 VURBJTJUNFTLRH-UHFFFAOYSA-N 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- AUHRDYPGCRKIKZ-UHFFFAOYSA-N 2-[2-methyl-3-(quinolin-2-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=CC=C2)C2=N1 AUHRDYPGCRKIKZ-UHFFFAOYSA-N 0.000 claims 1
- CMUBATJXNUXZRE-UHFFFAOYSA-N 2-[3-[(4-chlorophenyl)methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(Cl)C=C1 CMUBATJXNUXZRE-UHFFFAOYSA-N 0.000 claims 1
- ZCUYLCQVFFSXST-UHFFFAOYSA-N 2-[3-[(4-tert-butylphenyl)methyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C(C)(C)C)C=C1 ZCUYLCQVFFSXST-UHFFFAOYSA-N 0.000 claims 1
- BHEFOTSBJZWUIS-UHFFFAOYSA-N 2-[3-[1-(4-chlorophenyl)ethyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound CC=1N(CC(O)=O)C2=CC=C(F)C=C2C=1C(C)C1=CC=C(Cl)C=C1 BHEFOTSBJZWUIS-UHFFFAOYSA-N 0.000 claims 1
- XYLOSFUTUBOLNB-UHFFFAOYSA-N 2-[3-[1-(4-tert-butylphenyl)ethyl]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound CC=1N(CC(O)=O)C2=CC=C(F)C=C2C=1C(C)C1=CC=C(C(C)(C)C)C=C1 XYLOSFUTUBOLNB-UHFFFAOYSA-N 0.000 claims 1
- QILUMBJCLHPTEK-UHFFFAOYSA-N 2-[5-chloro-2-methyl-3-(quinolin-2-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=CC=C2)C2=N1 QILUMBJCLHPTEK-UHFFFAOYSA-N 0.000 claims 1
- JWGPBCUWRFVNDU-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-(1-naphthalen-2-ylethyl)indol-1-yl]acetic acid Chemical compound C1=CC=CC2=CC(C(C=3C4=CC(F)=CC=C4N(CC(O)=O)C=3C)C)=CC=C21 JWGPBCUWRFVNDU-UHFFFAOYSA-N 0.000 claims 1
- BYKXFHSGUBZCES-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-(naphthalen-2-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=CC=C2)C2=C1 BYKXFHSGUBZCES-UHFFFAOYSA-N 0.000 claims 1
- RAQFMAVUQKXQON-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-(quinoxalin-2-ylmethyl)indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CN=C(C=CC=C2)C2=N1 RAQFMAVUQKXQON-UHFFFAOYSA-N 0.000 claims 1
- HJLPNIQIMSEBHY-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[(4-phenylphenyl)methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC(C=C1)=CC=C1C1=CC=CC=C1 HJLPNIQIMSEBHY-UHFFFAOYSA-N 0.000 claims 1
- JSXSFKOJCMWLDV-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[1-(4-methylsulfonylphenyl)ethyl]indol-1-yl]acetic acid Chemical compound CC=1N(CC(O)=O)C2=CC=C(F)C=C2C=1C(C)C1=CC=C(S(C)(=O)=O)C=C1 JSXSFKOJCMWLDV-UHFFFAOYSA-N 0.000 claims 1
- SFESJDVHISLSIZ-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[1-[4-(trifluoromethyl)phenyl]ethyl]indol-1-yl]acetic acid Chemical compound CC=1N(CC(O)=O)C2=CC=C(F)C=C2C=1C(C)C1=CC=C(C(F)(F)F)C=C1 SFESJDVHISLSIZ-UHFFFAOYSA-N 0.000 claims 1
- FSYLFZCDQZBNBD-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-[[4-(trifluoromethyl)phenyl]methyl]indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C(F)(F)F)C=C1 FSYLFZCDQZBNBD-UHFFFAOYSA-N 0.000 claims 1
- RZEGYTODLNWOFL-UHFFFAOYSA-N 2-[5-fluoro-3-[(4-methoxyphenyl)methyl]-2-methylindol-1-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1CC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 RZEGYTODLNWOFL-UHFFFAOYSA-N 0.000 claims 1
- FOJBXYNSYGEMCI-UHFFFAOYSA-N 2-[5-fluoro-3-[(6-fluoroquinolin-2-yl)methyl]-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=C(F)C=C2)C2=N1 FOJBXYNSYGEMCI-UHFFFAOYSA-N 0.000 claims 1
- CIBHTCADKNJJQS-UHFFFAOYSA-N 2-[5-fluoro-3-[(8-hydroxyquinolin-2-yl)methyl]-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1CC1=CC=C(C=CC=C2O)C2=N1 CIBHTCADKNJJQS-UHFFFAOYSA-N 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- IECPWNUMDGFDKC-UHFFFAOYSA-N Fusicsaeure Natural products C12C(O)CC3C(=C(CCC=C(C)C)C(O)=O)C(OC(C)=O)CC3(C)C1(C)CCC1C2(C)CCC(O)C1C IECPWNUMDGFDKC-UHFFFAOYSA-N 0.000 claims 1
- UCHDWCPVSPXUMX-TZIWLTJVSA-N Montelukast Chemical compound CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC(O)=O)CC1 UCHDWCPVSPXUMX-TZIWLTJVSA-N 0.000 claims 1
- GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 claims 1
- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 230000000843 anti-fungal effect Effects 0.000 claims 1
- 230000002924 anti-infective effect Effects 0.000 claims 1
- 229940124691 antibody therapeutics Drugs 0.000 claims 1
- 229940121375 antifungal agent Drugs 0.000 claims 1
- 229940125715 antihistaminic agent Drugs 0.000 claims 1
- 239000000739 antihistaminic agent Substances 0.000 claims 1
- 229960005475 antiinfective agent Drugs 0.000 claims 1
- 229940124748 beta 2 agonist Drugs 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229960004022 clotrimazole Drugs 0.000 claims 1
- VNFPBHJOKIVQEB-UHFFFAOYSA-N clotrimazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNFPBHJOKIVQEB-UHFFFAOYSA-N 0.000 claims 1
- 239000003246 corticosteroid Substances 0.000 claims 1
- 229960001334 corticosteroids Drugs 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- HQINKYRZTRFVMI-UHFFFAOYSA-N ethyl 2-[5-fluoro-2-methyl-3-(1,3-thiazol-2-ylmethyl)indol-1-yl]acetate Chemical compound C12=CC(F)=CC=C2N(CC(=O)OCC)C(C)=C1CC1=NC=CS1 HQINKYRZTRFVMI-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- MGNNYOODZCAHBA-GQKYHHCASA-N fluticasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(O)[C@@]2(C)C[C@@H]1O MGNNYOODZCAHBA-GQKYHHCASA-N 0.000 claims 1
- 229960002714 fluticasone Drugs 0.000 claims 1
- IECPWNUMDGFDKC-MZJAQBGESA-N fusidic acid Chemical compound O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C(O)=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C IECPWNUMDGFDKC-MZJAQBGESA-N 0.000 claims 1
- 229960004675 fusidic acid Drugs 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 229960003444 immunosuppressant agent Drugs 0.000 claims 1
- 239000003018 immunosuppressive agent Substances 0.000 claims 1
- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims 1
- 229960003088 loratadine Drugs 0.000 claims 1
- JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229960005127 montelukast Drugs 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 229960000470 omalizumab Drugs 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 claims 1
- KASDHRXLYQOAKZ-ZPSXYTITSA-N pimecrolimus Chemical compound C/C([C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H]([C@H](C[C@H]2C)OC)[C@@H](OC)C[C@@H](C)C/C(C)=C/[C@H](C(C[C@H](O)[C@H]1C)=O)CC)=C\[C@@H]1CC[C@@H](Cl)[C@H](OC)C1 KASDHRXLYQOAKZ-ZPSXYTITSA-N 0.000 claims 1
- 229960005330 pimecrolimus Drugs 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 229960004017 salmeterol Drugs 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 229960001967 tacrolimus Drugs 0.000 claims 1
- QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 2
- 102000000536 PPAR gamma Human genes 0.000 description 1
- 108010016731 PPAR gamma Proteins 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 229960004586 rosiglitazone Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0324763.2A GB0324763D0 (en) | 2003-10-23 | 2003-10-23 | Use of compounds in therapy |
| PCT/GB2004/004417 WO2005044260A1 (en) | 2003-10-23 | 2004-10-19 | Use of crth2 antagonist compounds in therapy |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007509114A JP2007509114A (ja) | 2007-04-12 |
| JP2007509114A5 true JP2007509114A5 (https=) | 2009-03-12 |
| JP4313819B2 JP4313819B2 (ja) | 2009-08-12 |
Family
ID=29595698
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006536158A Expired - Fee Related JP4313819B2 (ja) | 2003-10-23 | 2004-10-19 | 治療におけるｃｒｔｈ２アンタゴニストの使用 |
Country Status (25)
| Country | Link |
|---|---|
| US (5) | US7582672B2 (https=) |
| EP (2) | EP1682121B1 (https=) |
| JP (1) | JP4313819B2 (https=) |
| KR (1) | KR20060096145A (https=) |
| CN (1) | CN101141956B (https=) |
| AT (1) | ATE439129T1 (https=) |
| AU (1) | AU2004287245B2 (https=) |
| BR (1) | BRPI0415374B8 (https=) |
| CA (1) | CA2543199C (https=) |
| CY (1) | CY1109980T1 (https=) |
| DE (1) | DE602004022579D1 (https=) |
| DK (1) | DK1682121T3 (https=) |
| ES (1) | ES2330113T3 (https=) |
| GB (1) | GB0324763D0 (https=) |
| HR (1) | HRP20090577T8 (https=) |
| IL (1) | IL175085A0 (https=) |
| NO (1) | NO335228B1 (https=) |
| NZ (1) | NZ547319A (https=) |
| PL (1) | PL1682121T3 (https=) |
| PT (1) | PT1682121E (https=) |
| RU (1) | RU2412934C2 (https=) |
| SI (1) | SI1682121T1 (https=) |
| UA (1) | UA86602C2 (https=) |
| WO (1) | WO2005044260A1 (https=) |
| ZA (1) | ZA200603235B (https=) |
Families Citing this family (78)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0301010D0 (sv) | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| SA04250253B1 (ar) | 2003-08-21 | 2009-11-10 | استرازينيكا ايه بي | احماض فينوكسي اسيتيك مستبدلة باعتبارها مركبات صيدلانية لعلاج الامراض التنفسية مثل الربو ومرض الانسداد الرئوي المزمن |
| GB0324763D0 (en) * | 2003-10-23 | 2003-11-26 | Oxagen Ltd | Use of compounds in therapy |
| GB0415320D0 (en) | 2004-07-08 | 2004-08-11 | Astrazeneca Ab | Novel compounds |
| GB0418830D0 (en) | 2004-08-24 | 2004-09-22 | Astrazeneca Ab | Novel compounds |
| JP5208510B2 (ja) | 2004-11-23 | 2013-06-12 | アストラゼネカ・アクチエボラーグ | 呼吸器疾患の処置に有用なフェノキシ酢酸誘導体 |
| ES2369782T3 (es) | 2004-12-27 | 2011-12-05 | Actelion Pharmaceuticals Ltd. | Derivados de 2,3,4,9-tetrahidro-1h-carbazol como antagonistas del receptor crth2. |
| GB0504150D0 (en) * | 2005-03-01 | 2005-04-06 | Oxagen Ltd | Microcrystalline material |
| GB0505048D0 (en) | 2005-03-11 | 2005-04-20 | Oxagen Ltd | Compounds with PGD antagonist activity |
| GB0512944D0 (en) * | 2005-06-24 | 2005-08-03 | Argenta Discovery Ltd | Indolizine compounds |
| JP5064219B2 (ja) | 2005-07-22 | 2012-10-31 | 塩野義製薬株式会社 | Ｐｇｄ２受容体アンタゴニスト活性を有するアザインドール酸誘導体 |
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