CA2688614C - Phenyl-butoxy-phenyl-ethynyl substituted indole compounds having cyslt1/cyslt2 receptor antagonistic activity - Google Patents
Phenyl-butoxy-phenyl-ethynyl substituted indole compounds having cyslt1/cyslt2 receptor antagonistic activity Download PDFInfo
- Publication number
- CA2688614C CA2688614C CA2688614A CA2688614A CA2688614C CA 2688614 C CA2688614 C CA 2688614C CA 2688614 A CA2688614 A CA 2688614A CA 2688614 A CA2688614 A CA 2688614A CA 2688614 C CA2688614 C CA 2688614C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- butoxy
- indole
- methyl
- diyl
- 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.)
- Expired - Fee Related
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- -1 Phenyl-butoxy-phenyl-ethynyl Chemical group 0.000 title claims description 58
- 102000004155 Cysteinyl leukotriene receptor 2 Human genes 0.000 title abstract description 21
- 108090000655 Cysteinyl leukotriene receptor 2 Proteins 0.000 title abstract description 21
- 102000010918 Cysteinyl leukotriene receptors Human genes 0.000 title abstract description 19
- 108050001116 Cysteinyl leukotriene receptors Proteins 0.000 title abstract description 19
- 230000003042 antagnostic effect Effects 0.000 title abstract description 17
- 150000002475 indoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 315
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 114
- 239000002253 acid Substances 0.000 claims description 69
- 150000003839 salts Chemical class 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 239000012453 solvate Substances 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- HLPSHXIVNYPKND-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-2-methyl-7-[2-[4-[4-(2,3,4,5,6-pentafluorophenyl)butoxy]phenyl]ethynyl]indol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=CC=CC=1C#CC(C=C1)=CC=C1OCCCCC1=C(F)C(F)=C(F)C(F)=C1F HLPSHXIVNYPKND-UHFFFAOYSA-N 0.000 claims 2
- SILHYVDKGHXGBL-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-4-fluoro-7-[2-[4-[4-(3-fluoro-2-methylphenyl)butoxy]phenyl]ethynyl]-2-methylindol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=C(F)C=CC=1C#CC(C=C1)=CC=C1OCCCCC1=CC=CC(F)=C1C SILHYVDKGHXGBL-UHFFFAOYSA-N 0.000 claims 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 2
- TXTOGNHBXCXSDY-UHFFFAOYSA-N 2-[1-[[1-(carboxymethyl)-2-methyl-7-[2-[4-[4-(2,3,4,5,6-pentafluorophenyl)butoxy]phenyl]ethynyl]indol-3-yl]methyl]cyclopropyl]acetic acid Chemical compound C12=CC=CC(C#CC=3C=CC(OCCCCC=4C(=C(F)C(F)=C(F)C=4F)F)=CC=3)=C2N(CC(O)=O)C(C)=C1CC1(CC(O)=O)CC1 TXTOGNHBXCXSDY-UHFFFAOYSA-N 0.000 claims 1
- URNRXOPHGYWKLX-UHFFFAOYSA-N 2-[1-[[1-(carboxymethyl)-7-[2-[4-[4-(3-chloro-2-methylphenyl)butoxy]phenyl]ethynyl]-2-methylindol-3-yl]methyl]cyclopropyl]acetic acid Chemical compound C12=CC=CC(C#CC=3C=CC(OCCCCC=4C(=C(Cl)C=CC=4)C)=CC=3)=C2N(CC(O)=O)C(C)=C1CC1(CC(O)=O)CC1 URNRXOPHGYWKLX-UHFFFAOYSA-N 0.000 claims 1
- ZSIOUYAJBOECNZ-UHFFFAOYSA-N 2-[1-[[1-(carboxymethyl)-7-[2-[4-[4-(3-fluoro-2-methylphenyl)butoxy]phenyl]ethynyl]-2-methylindol-3-yl]methyl]cyclopropyl]acetic acid Chemical compound C12=CC=CC(C#CC=3C=CC(OCCCCC=4C(=C(F)C=CC=4)C)=CC=3)=C2N(CC(O)=O)C(C)=C1CC1(CC(O)=O)CC1 ZSIOUYAJBOECNZ-UHFFFAOYSA-N 0.000 claims 1
- PYUVJTWRSZWPDP-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-2-methyl-7-[2-[4-[4-(2,3,4,5-tetrafluorophenyl)butoxy]phenyl]ethynyl]indol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=CC=CC=1C#CC(C=C1)=CC=C1OCCCCC1=CC(F)=C(F)C(F)=C1F PYUVJTWRSZWPDP-UHFFFAOYSA-N 0.000 claims 1
- HUIIHFBKBWWWJM-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-2-methyl-7-[2-[4-[4-(2,3,4,6-tetrafluorophenyl)butoxy]phenyl]ethynyl]indol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=CC=CC=1C#CC(C=C1)=CC=C1OCCCCC1=C(F)C=C(F)C(F)=C1F HUIIHFBKBWWWJM-UHFFFAOYSA-N 0.000 claims 1
- BCNPNPHFYVYYGW-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-2-methyl-7-[2-[4-[4-(3,4,5-trifluorophenyl)butoxy]phenyl]ethynyl]indol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=CC=CC=1C#CC(C=C1)=CC=C1OCCCCC1=CC(F)=C(F)C(F)=C1 BCNPNPHFYVYYGW-UHFFFAOYSA-N 0.000 claims 1
- OKNHXOCNFKQLBL-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-4-fluoro-2-methyl-7-[2-[4-[4-(2,3,4,5,6-pentafluorophenyl)butoxy]phenyl]ethynyl]indol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=C(F)C=CC=1C#CC(C=C1)=CC=C1OCCCCC1=C(F)C(F)=C(F)C(F)=C1F OKNHXOCNFKQLBL-UHFFFAOYSA-N 0.000 claims 1
- HOXJOAWSVADHMC-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-4-fluoro-2-methyl-7-[2-[4-[4-(2,3,4,6-tetrafluorophenyl)butoxy]phenyl]ethynyl]indol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=C(F)C=CC=1C#CC(C=C1)=CC=C1OCCCCC1=C(F)C=C(F)C(F)=C1F HOXJOAWSVADHMC-UHFFFAOYSA-N 0.000 claims 1
- CUZTUQOWAJAZCQ-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-7-[2-[4-[4-(2,3,4,5,6-pentafluorophenyl)butoxy]phenyl]ethynyl]indol-3-yl]butanoic acid Chemical compound C1=CC=C2C(CCCC(=O)O)=CN(CCCC(O)=O)C2=C1C#CC(C=C1)=CC=C1OCCCCC1=C(F)C(F)=C(F)C(F)=C1F CUZTUQOWAJAZCQ-UHFFFAOYSA-N 0.000 claims 1
- FHIWKHKLAOPBDE-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-7-[2-[4-[4-(3-chloro-2-methylphenyl)butoxy]phenyl]ethynyl]-2-methylindol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=CC=CC=1C#CC(C=C1)=CC=C1OCCCCC1=CC=CC(Cl)=C1C FHIWKHKLAOPBDE-UHFFFAOYSA-N 0.000 claims 1
- AWYSEGZBFYYQQL-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-7-[2-[4-[4-(3-chloro-2-methylphenyl)butoxy]phenyl]ethynyl]-4-fluoro-2-methylindol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=C(F)C=CC=1C#CC(C=C1)=CC=C1OCCCCC1=CC=CC(Cl)=C1C AWYSEGZBFYYQQL-UHFFFAOYSA-N 0.000 claims 1
- AGUZWUNQAJUHQG-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-7-[2-[4-[4-(3-fluoro-2-methylphenyl)butoxy]phenyl]ethynyl]-2-methylindol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=CC=CC=1C#CC(C=C1)=CC=C1OCCCCC1=CC=CC(F)=C1C AGUZWUNQAJUHQG-UHFFFAOYSA-N 0.000 claims 1
- YWFJJZNSTFOQLJ-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-7-[2-[4-[4-(4-fluoro-2-methylphenyl)butoxy]phenyl]ethynyl]-2-methylindol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=CC=CC=1C#CC(C=C1)=CC=C1OCCCCC1=CC=C(F)C=C1C YWFJJZNSTFOQLJ-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 22
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- 206010039085 Rhinitis allergic Diseases 0.000 abstract description 4
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- 208000029523 Interstitial Lung disease Diseases 0.000 abstract description 2
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- MNDBXUUTURYVHR-UHFFFAOYSA-N roflumilast Chemical compound FC(F)OC1=CC=C(C(=O)NC=2C(=CN=CC=2Cl)Cl)C=C1OCC1CC1 MNDBXUUTURYVHR-UHFFFAOYSA-N 0.000 description 1
- HJORMJIFDVBMOB-UHFFFAOYSA-N rolipram Chemical compound COC1=CC=C(C2CC(=O)NC2)C=C1OC1CCCC1 HJORMJIFDVBMOB-UHFFFAOYSA-N 0.000 description 1
- 229950005741 rolipram Drugs 0.000 description 1
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- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
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- KGZGMOFDZSCICN-YCBFMBTMSA-M sodium;(2s)-3-[4-[(7-fluoroquinolin-2-yl)methoxy]phenyl]-2-(quinoline-2-carbonylamino)propanoate Chemical compound [Na+].C1=CC=CC2=NC(C(=O)N[C@@H](CC=3C=CC(OCC=4N=C5C=C(F)C=CC5=CC=4)=CC=3)C(=O)[O-])=CC=C21 KGZGMOFDZSCICN-YCBFMBTMSA-M 0.000 description 1
- BGXXYHIWOXFRLF-UHFFFAOYSA-M sodium;2-(imidazol-1-ylmethyl)-4,5-dihydro-1-benzothiophene-6-carboxylate Chemical compound [Na+].C=1C=2CCC(C(=O)[O-])=CC=2SC=1CN1C=CN=C1 BGXXYHIWOXFRLF-UHFFFAOYSA-M 0.000 description 1
- PRTHJNRDIBBOIR-UHFFFAOYSA-N sodium;3-[(4-tert-butyl-1,3-thiazol-2-yl)methoxy]-n-[5-[3-(4-chlorophenyl)sulfonylpropyl]-2-(2h-tetrazol-5-ylmethoxy)phenyl]benzamide Chemical compound [Na+].CC(C)(C)C1=CSC(COC=2C=C(C=CC=2)C(=O)NC=2C(=CC=C(CCCS(=O)(=O)C=3C=CC(Cl)=CC=3)C=2)OCC2=NNN=N2)=N1 PRTHJNRDIBBOIR-UHFFFAOYSA-N 0.000 description 1
- QIBQVFYOTMPEIP-UHFFFAOYSA-M sodium;3-[4-[(4-chlorophenyl)sulfonylamino]butyl]-6-propan-2-ylazulene-1-sulfonate Chemical compound [Na+].C=1C(S([O-])(=O)=O)=C2C=CC(C(C)C)=CC=C2C=1CCCCNS(=O)(=O)C1=CC=C(Cl)C=C1 QIBQVFYOTMPEIP-UHFFFAOYSA-M 0.000 description 1
- UVMDAJYLEKEIPJ-RWRWEHELSA-M sodium;7-[(1r,2s,3e,5z)-10-(4-acetyl-3-hydroxy-2-propylphenoxy)-1-hydroxy-1-[3-(trifluoromethyl)phenyl]deca-3,5-dien-2-yl]sulfanyl-4-oxochromene-2-carboxylate Chemical compound [Na+].CCCC1=C(O)C(C(C)=O)=CC=C1OCCCC\C=C/C=C/[C@@H]([C@H](O)C=1C=C(C=CC=1)C(F)(F)F)SC1=CC=C2C(=O)C=C(C([O-])=O)OC2=C1 UVMDAJYLEKEIPJ-RWRWEHELSA-M 0.000 description 1
- ZDEVPOBNLIVGFA-UHFFFAOYSA-M sodium;7-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)-2-hydroxypropoxy]-4-oxo-8-propylchromene-2-carboxylate Chemical compound [Na+].CCCC1=C(O)C(C(C)=O)=CC=C1OCC(O)COC1=CC=C2C(=O)C=C(C([O-])=O)OC2=C1CCC ZDEVPOBNLIVGFA-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- YPHOSUPSOWQQCB-AFOLHBCXSA-N sulukast Chemical compound CCCCCCCCC\C=C/C=C/[C@@H](SCCC(O)=O)[C@@H](O)C1=CC=CC(C2=NNN=N2)=C1 YPHOSUPSOWQQCB-AFOLHBCXSA-N 0.000 description 1
- 229950009709 sulukast Drugs 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
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- XYKWNRUXCOIMFZ-UHFFFAOYSA-N tepoxalin Chemical compound C1=CC(OC)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=CC(CCC(=O)N(C)O)=N1 XYKWNRUXCOIMFZ-UHFFFAOYSA-N 0.000 description 1
- KFVSLSTULZVNPG-UHFFFAOYSA-N terbutaline sulfate Chemical compound [O-]S([O-])(=O)=O.CC(C)(C)[NH2+]CC(O)C1=CC(O)=CC(O)=C1.CC(C)(C)[NH2+]CC(O)C1=CC(O)=CC(O)=C1 KFVSLSTULZVNPG-UHFFFAOYSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- HTJXMOGUGMSZOG-UHFFFAOYSA-N tiaramide Chemical compound C1CN(CCO)CCN1C(=O)CN1C(=O)SC2=CC=C(Cl)C=C21 HTJXMOGUGMSZOG-UHFFFAOYSA-N 0.000 description 1
- 229950010302 tiaramide Drugs 0.000 description 1
- PFENFDGYVLAFBR-UHFFFAOYSA-N tinoridine Chemical compound C1CC=2C(C(=O)OCC)=C(N)SC=2CN1CC1=CC=CC=C1 PFENFDGYVLAFBR-UHFFFAOYSA-N 0.000 description 1
- 229950010298 tinoridine Drugs 0.000 description 1
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- 210000001519 tissue Anatomy 0.000 description 1
- MWYHLEQJTQJHSS-UHFFFAOYSA-N tomelukast Chemical compound C1=CC(C(C)=O)=C(O)C(CCC)=C1OCCCCC1=NNN=N1 MWYHLEQJTQJHSS-UHFFFAOYSA-N 0.000 description 1
- 229950010953 tomelukast Drugs 0.000 description 1
- 238000007483 tonsillectomy Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229960005342 tranilast Drugs 0.000 description 1
- NZHGWWWHIYHZNX-CSKARUKUSA-N tranilast Chemical compound C1=C(OC)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1C(O)=O NZHGWWWHIYHZNX-CSKARUKUSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 229940126307 triamcinolone acetate Drugs 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 description 1
- 229960001593 triprolidine hydrochloride Drugs 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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- MDYZKJNTKZIUSK-UHFFFAOYSA-N tyloxapol Chemical compound O=C.C1CO1.CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 MDYZKJNTKZIUSK-UHFFFAOYSA-N 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
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- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- MWLSOWXNZPKENC-UHFFFAOYSA-N zileuton Chemical compound C1=CC=C2SC(C(N(O)C(N)=O)C)=CC2=C1 MWLSOWXNZPKENC-UHFFFAOYSA-N 0.000 description 1
- MWLSOWXNZPKENC-SSDOTTSWSA-N zileuton Chemical compound C1=CC=C2SC([C@H](N(O)C(N)=O)C)=CC2=C1 MWLSOWXNZPKENC-SSDOTTSWSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
-
- 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
- A61P11/02—Nasal agents, e.g. decongestants
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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
- A61P11/14—Antitussive agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A—HUMAN NECESSITIES
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008325815 | 2008-12-22 | ||
| JP2008-325815 | 2008-12-22 |
Publications (2)
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| CA2688614A1 CA2688614A1 (en) | 2010-06-22 |
| CA2688614C true CA2688614C (en) | 2015-01-06 |
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| CA2688614A Expired - Fee Related CA2688614C (en) | 2008-12-22 | 2009-12-15 | Phenyl-butoxy-phenyl-ethynyl substituted indole compounds having cyslt1/cyslt2 receptor antagonistic activity |
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| EP (1) | EP2206698B1 (enExample) |
| JP (2) | JP5012884B2 (enExample) |
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| CN (1) | CN101759628B (enExample) |
| AU (1) | AU2009250960C1 (enExample) |
| BR (1) | BRPI0905601A2 (enExample) |
| CA (1) | CA2688614C (enExample) |
| DK (1) | DK2206698T3 (enExample) |
| ES (1) | ES2387185T3 (enExample) |
| IL (1) | IL202869A (enExample) |
| MX (1) | MX2009013926A (enExample) |
| NZ (1) | NZ582208A (enExample) |
| PL (1) | PL2206698T3 (enExample) |
| PT (1) | PT2206698E (enExample) |
| RU (1) | RU2505531C2 (enExample) |
| TW (1) | TWI469965B (enExample) |
| ZA (1) | ZA200909096B (enExample) |
Families Citing this family (7)
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| KR20130112715A (ko) | 2010-06-21 | 2013-10-14 | 오노 야꾸힝 고교 가부시키가이샤 | 4,4''-[4-플루오로-7-(｛4-[4-(3-플루오로-2-메틸페닐)부톡시]페닐｝에티닐)-2-메틸-1h-인돌-1,3-디일]디부탄산, 4,4''-[2-메틸-7-(｛4-[4-(펜타플루오로페닐)부톡시]페닐｝에티닐)-1h-인돌-1,3-디일]디부탄산 및 4,4''-[4-플루오로-2-메틸-7-(｛4-[4-(2,3,4,6-테트라플루오로페닐)부톡시]페닐｝에티닐)-1h-인돌-1,3-디일]디부탄산의 신규 결정형 |
| KR101171790B1 (ko) | 2010-07-30 | 2012-08-13 | 현대자동차주식회사 | 인출식 자전거 캐리어 |
| ES2612492T3 (es) | 2010-12-28 | 2017-05-17 | Sanofi | Nuevos derivados de piridiminas, su preparación y su utilización farmacéutica como inhibidores de fosforilación de AKT (PKB) |
| EP2537866A1 (en) * | 2011-06-21 | 2012-12-26 | Serumwerk Bernburg AG | Hydroxyethyl starch derivatives, method for manufacturing the same and therapeutical uses thereof |
| CN103893146A (zh) * | 2012-12-25 | 2014-07-02 | 天津药物研究院 | 含福多司坦缓释剂型 |
| US11427591B2 (en) * | 2018-10-17 | 2022-08-30 | Insilico Medicine Ip Limited | Kinase inhibitors |
| WO2021221111A1 (ja) * | 2020-04-30 | 2021-11-04 | 国立大学法人京都大学 | Ｒｎａウイルス関連疾患の予防又は治療剤 |
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| JPH01192476A (ja) | 1988-01-25 | 1989-08-02 | Kawasaki Steel Corp | 溶接鋼管の製造方法 |
| PT93943A (pt) | 1989-05-05 | 1991-02-08 | Searle & Co | Processo para a preparacao de composicoes contendo compostos indole-2-carboxilato para tratamento de perturbacoes do snc |
| US5137910A (en) * | 1989-05-05 | 1992-08-11 | C.D. Searle & Co. | Compositions containing indole-2-carboxylate compounds for treatment of CNS disorders |
| US5229413A (en) * | 1989-05-05 | 1993-07-20 | G. D. Searle & Co. | Compositions containing indole-2-carboxylate compounds for treatment of CNS disorders |
| CA2019335C (en) | 1989-06-27 | 2000-08-01 | Mitoshi Konno | Phenylalkan (en)oic acids |
| GB9027018D0 (en) * | 1990-12-12 | 1991-01-30 | Ici Plc | Heterocyclic compounds |
| US5530019A (en) * | 1993-04-05 | 1996-06-25 | Fujisawa Pharmaceutical Co., Ltd. | Indole derivatives useful as testosterone 5α-reductase inhibitors |
| DE69605128T2 (de) | 1995-10-10 | 2000-03-02 | Pfizer Inc., New York | Indol-carbamate als leukotriene antagonisten |
| FR2766824B1 (fr) * | 1997-07-30 | 1999-09-10 | Adir | Nouveaux composes heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
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| JP2003025362A (ja) | 2001-07-18 | 2003-01-29 | Nippon Tokushu Toryo Co Ltd | 通気性を有する発泡プラスチック及びその製法 |
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| AU2003225131A1 (en) | 2002-04-23 | 2003-11-10 | Aventis Pharmaceuticals Inc. | 3-substituted amino-1h-indole-2-carboxylic acid and 3-substituted amino-benzo' b! thiophene-2-carboxylic acid derivatives as interieukin-4 gene expression inhibitors |
| SE0202241D0 (sv) | 2002-07-17 | 2002-07-17 | Astrazeneca Ab | Novel Compounds |
| CA2523743A1 (en) | 2003-04-30 | 2004-11-18 | The Institutes For Pharmaceutical Discovery, Llc | Heterocycle substituted carboxylic acids as inhibitors of protein tyrosine phosphatase-1b |
| AU2004268865B8 (en) * | 2003-09-01 | 2011-01-06 | Ono Pharmaceutical Co., Ltd. | Condensed ring compound and use thereof |
| AU2006216170B2 (en) * | 2005-02-25 | 2012-02-09 | Ono Pharmaceutical Co., Ltd. | Indole compound and use thereof |
-
2009
- 2009-12-10 TW TW98142268A patent/TWI469965B/zh not_active IP Right Cessation
- 2009-12-15 AU AU2009250960A patent/AU2009250960C1/en not_active Ceased
- 2009-12-15 CA CA2688614A patent/CA2688614C/en not_active Expired - Fee Related
- 2009-12-17 MX MX2009013926A patent/MX2009013926A/es active IP Right Grant
- 2009-12-21 CN CN2009102608650A patent/CN101759628B/zh not_active Expired - Fee Related
- 2009-12-21 PL PL09180244T patent/PL2206698T3/pl unknown
- 2009-12-21 ES ES09180244T patent/ES2387185T3/es active Active
- 2009-12-21 JP JP2009289494A patent/JP5012884B2/ja active Active
- 2009-12-21 ZA ZA200909096A patent/ZA200909096B/en unknown
- 2009-12-21 PT PT09180244T patent/PT2206698E/pt unknown
- 2009-12-21 NZ NZ582208A patent/NZ582208A/en not_active IP Right Cessation
- 2009-12-21 RU RU2009147506/04A patent/RU2505531C2/ru not_active IP Right Cessation
- 2009-12-21 KR KR1020090128213A patent/KR101464778B1/ko not_active Expired - Fee Related
- 2009-12-21 IL IL202869A patent/IL202869A/en not_active IP Right Cessation
- 2009-12-21 EP EP09180244A patent/EP2206698B1/en not_active Not-in-force
- 2009-12-21 BR BRPI0905601-7A patent/BRPI0905601A2/pt not_active IP Right Cessation
- 2009-12-21 DK DK09180244.7T patent/DK2206698T3/da active
- 2009-12-22 US US12/644,378 patent/US8115014B2/en not_active Expired - Fee Related
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2012
- 2012-03-07 JP JP2012050217A patent/JP2012144546A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JP5012884B2 (ja) | 2012-08-29 |
| BRPI0905601A2 (pt) | 2012-05-02 |
| DK2206698T3 (da) | 2012-08-27 |
| US20100160647A1 (en) | 2010-06-24 |
| AU2009250960C1 (en) | 2014-01-23 |
| AU2009250960A1 (en) | 2010-07-08 |
| JP2010168359A (ja) | 2010-08-05 |
| CA2688614A1 (en) | 2010-06-22 |
| EP2206698A1 (en) | 2010-07-14 |
| EP2206698B1 (en) | 2012-07-18 |
| JP2012144546A (ja) | 2012-08-02 |
| CN101759628B (zh) | 2013-02-27 |
| ZA200909096B (en) | 2010-09-29 |
| RU2009147506A (ru) | 2011-06-27 |
| PT2206698E (pt) | 2012-08-03 |
| US8115014B2 (en) | 2012-02-14 |
| MX2009013926A (es) | 2010-06-22 |
| NZ582208A (en) | 2011-05-27 |
| RU2505531C2 (ru) | 2014-01-27 |
| TW201026664A (en) | 2010-07-16 |
| PL2206698T3 (pl) | 2012-12-31 |
| AU2009250960B2 (en) | 2013-09-05 |
| KR20100074036A (ko) | 2010-07-01 |
| TWI469965B (zh) | 2015-01-21 |
| ES2387185T3 (es) | 2012-09-17 |
| IL202869A (en) | 2015-02-26 |
| CN101759628A (zh) | 2010-06-30 |
| KR101464778B1 (ko) | 2014-11-24 |
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