UA79464C2 - Substituted indoles, methods for their production and method for treating disorders mediated by prostaglandin d2 - Google Patents
Substituted indoles, methods for their production and method for treating disorders mediated by prostaglandin d2 Download PDFInfo
- Publication number
- UA79464C2 UA79464C2 UA20041109794A UA20041109794A UA79464C2 UA 79464 C2 UA79464 C2 UA 79464C2 UA 20041109794 A UA20041109794 A UA 20041109794A UA 20041109794 A UA20041109794 A UA 20041109794A UA 79464 C2 UA79464 C2 UA 79464C2
- Authority
- UA
- Ukraine
- Prior art keywords
- indole
- acetic acid
- thio
- dimethyl
- chlorophenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- 230000001404 mediated effect Effects 0.000 title claims description 4
- 150000002475 indoles Chemical class 0.000 title abstract description 3
- 238000004519 manufacturing process Methods 0.000 title description 6
- BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 title 1
- BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 178
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 178
- 238000006243 chemical reaction Methods 0.000 claims description 54
- 125000003118 aryl group Chemical group 0.000 claims description 28
- -1 Si-Svalkyl Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical group 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 206010039083 rhinitis Diseases 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004185 ester group Chemical group 0.000 claims description 5
- 229910052731 fluorine Chemical group 0.000 claims description 5
- 239000011737 fluorine Chemical group 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- IEWVQISRDPDETE-UHFFFAOYSA-N 2-(2,5-dimethyl-3-quinolin-8-ylsulfanylindol-1-yl)acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=CC2=CC=CN=C12 IEWVQISRDPDETE-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- QQAVOUWHBSNMAR-UHFFFAOYSA-N 2-[3-(1h-imidazol-2-ylsulfanyl)-2,5-dimethylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1SC1=NC=CN1 QQAVOUWHBSNMAR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 150000003180 prostaglandins Chemical class 0.000 claims description 2
- YLARYOPAOYGKNQ-UHFFFAOYSA-N 2-[2,5-dimethyl-3-(1h-1,2,4-triazol-5-ylsulfanyl)indol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1SC=1N=CNN=1 YLARYOPAOYGKNQ-UHFFFAOYSA-N 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 88
- 239000000047 product Substances 0.000 description 82
- 238000005481 NMR spectroscopy Methods 0.000 description 66
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 58
- 239000007787 solid Substances 0.000 description 56
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 51
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 238000003756 stirring Methods 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 229910052740 iodine Inorganic materials 0.000 description 26
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
- 239000003480 eluent Substances 0.000 description 25
- 239000011630 iodine Substances 0.000 description 25
- 239000012071 phase Substances 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- 239000003921 oil Substances 0.000 description 23
- 235000019439 ethyl acetate Nutrition 0.000 description 22
- 238000003818 flash chromatography Methods 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000543 intermediate Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 239000012453 solvate Substances 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 239000012267 brine Substances 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000012528 membrane Substances 0.000 description 9
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 235000011054 acetic acid Nutrition 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 150000003863 ammonium salts Chemical class 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 7
- 150000004702 methyl esters Chemical class 0.000 description 7
- 102000005962 receptors Human genes 0.000 description 7
- 108020003175 receptors Proteins 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 239000011324 bead Substances 0.000 description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
- 125000004494 ethyl ester group Chemical group 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000008194 pharmaceutical composition Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 6
- 239000000872 buffer Substances 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 5
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
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- 208000010668 atopic eczema Diseases 0.000 description 4
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 230000001684 chronic effect Effects 0.000 description 4
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- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 239000002207 metabolite Substances 0.000 description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000651 prodrug Substances 0.000 description 4
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
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- 208000011580 syndromic disease Diseases 0.000 description 3
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- 229940103494 thiosalicylic acid Drugs 0.000 description 3
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
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- MHTSJSRDFXZFHQ-UHFFFAOYSA-N quinoline-8-thiol Chemical compound C1=CN=C2C(S)=CC=CC2=C1 MHTSJSRDFXZFHQ-UHFFFAOYSA-N 0.000 description 1
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- MFBOGIVSZKQAPD-UHFFFAOYSA-M sodium butyrate Chemical compound [Na+].CCCC([O-])=O MFBOGIVSZKQAPD-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- 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
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
-
- 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D403/12—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 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
- C07D413/02—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
- 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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE0201635A SE0201635D0 (sv) | 2002-05-30 | 2002-05-30 | Novel compounds |
PCT/SE2003/000856 WO2003101961A1 (fr) | 2002-05-30 | 2003-05-27 | Nouveaux indoles substitues |
Publications (1)
Publication Number | Publication Date |
---|---|
UA79464C2 true UA79464C2 (en) | 2007-06-25 |
Family
ID=20288018
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
UA20041109794A UA79464C2 (en) | 2002-05-30 | 2003-05-27 | Substituted indoles, methods for their production and method for treating disorders mediated by prostaglandin d2 |
Country Status (25)
Country | Link |
---|---|
US (1) | US7166607B2 (fr) |
EP (1) | EP1513812B1 (fr) |
JP (1) | JP4485354B2 (fr) |
KR (1) | KR20050010507A (fr) |
CN (1) | CN100404505C (fr) |
AR (1) | AR039934A1 (fr) |
AT (1) | ATE501118T1 (fr) |
AU (1) | AU2003228201A1 (fr) |
BR (1) | BR0311494A (fr) |
CA (1) | CA2487675A1 (fr) |
CO (1) | CO5631431A2 (fr) |
DE (1) | DE60336314D1 (fr) |
ES (1) | ES2360936T3 (fr) |
IS (1) | IS7607A (fr) |
MX (1) | MXPA04011876A (fr) |
MY (1) | MY133624A (fr) |
NO (1) | NO20045589L (fr) |
NZ (1) | NZ536883A (fr) |
PL (1) | PL375111A1 (fr) |
RU (1) | RU2288914C2 (fr) |
SE (1) | SE0201635D0 (fr) |
TW (1) | TW200407305A (fr) |
UA (1) | UA79464C2 (fr) |
WO (1) | WO2003101961A1 (fr) |
ZA (1) | ZA200409641B (fr) |
Families Citing this family (98)
Publication number | Priority date | Publication date | Assignee | Title |
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TW200307542A (en) * | 2002-05-30 | 2003-12-16 | Astrazeneca Ab | Novel compounds |
SE0201635D0 (sv) | 2002-05-30 | 2002-05-30 | Astrazeneca Ab | Novel compounds |
SE0202241D0 (sv) * | 2002-07-17 | 2002-07-17 | Astrazeneca Ab | Novel Compounds |
EA011087B1 (ru) | 2002-12-20 | 2008-12-30 | Эмджен Инк. | Соединения и фармацевтические композиции для лечения воспалительных заболеваний |
SE0301010D0 (sv) | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
SE0301569D0 (sv) * | 2003-05-27 | 2003-05-27 | Astrazeneca Ab | Novel compounds |
SE0302232D0 (sv) * | 2003-08-18 | 2003-08-18 | 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 |
RU2006109108A (ru) * | 2003-10-14 | 2007-11-20 | Оксаген Лимитед (GB) | Соединения, обладающие активностью антагонистов crth2 рецепторов |
GB0324763D0 (en) | 2003-10-23 | 2003-11-26 | Oxagen Ltd | Use of compounds in therapy |
SE0303180D0 (sv) * | 2003-11-26 | 2003-11-26 | Astrazeneca Ab | Novel compounds |
JP4051398B2 (ja) | 2004-03-11 | 2008-02-20 | アクテリオン ファマシューティカルズ リミテッド | テトラヒドロピリドインドール誘導体 |
US7417063B2 (en) | 2004-04-13 | 2008-08-26 | Bristol-Myers Squibb Company | Bicyclic heterocycles useful as serine protease inhibitors |
JP2008500991A (ja) | 2004-05-29 | 2008-01-17 | 7ティーエム ファーマ エイ/エス | 医学的使用のためのcrth2レセプターリガンド |
GB0412914D0 (en) * | 2004-06-10 | 2004-07-14 | Oxagen Ltd | Compounds |
MY144903A (en) * | 2004-06-17 | 2011-11-30 | Novartis Ag | Pyrrolopyridine derivatives and their use as crth2 antagonists |
GB0415320D0 (en) | 2004-07-08 | 2004-08-11 | Astrazeneca Ab | Novel compounds |
GB0418830D0 (en) | 2004-08-24 | 2004-09-22 | Astrazeneca Ab | Novel compounds |
CA2577748A1 (fr) * | 2004-08-26 | 2006-03-02 | Actelion Pharmaceuticals Ltd | Derives de l'acide 2-sulfanyl-benzoimidazol-1-yl-acetique en tant qu'antagonistes de crth2 |
JP2008513512A (ja) | 2004-09-21 | 2008-05-01 | アサーシス, インク. | Crth2受容体拮抗作用を示すインドール酢酸およびこれらの使用 |
WO2006049889A1 (fr) * | 2004-10-27 | 2006-05-11 | Janssen Pharmaceutica N.V. | Derives d'indole utiles en tant que modulateurs recepteurs de progesterone |
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 |
RU2404163C2 (ru) | 2004-12-27 | 2010-11-20 | Актелион Фармасьютиклз Лтд | Производные 2,3,4,9-тетрагидро-1h-карбазола в качестве антагонистов рецептора crth2 |
GB0500604D0 (en) * | 2005-01-13 | 2005-02-16 | Astrazeneca Ab | Novel process |
US7842692B2 (en) | 2005-07-22 | 2010-11-30 | Shionogi & Co., Ltd. | Azaindole derivative having PGD2 receptor antagonistic activity |
ES2372701T3 (es) | 2005-07-22 | 2012-01-25 | Shionogi & Co., Ltd. | Derivado de indol que tiene actividad antagonista del receptor de pgd2. |
US20070027105A1 (en) | 2005-07-26 | 2007-02-01 | Alza Corporation | Peroxide removal from drug delivery vehicle |
TW200745003A (en) | 2005-10-06 | 2007-12-16 | Astrazeneca Ab | Novel compounds |
JP5155171B2 (ja) | 2005-10-06 | 2013-02-27 | アストラゼネカ・アクチエボラーグ | 新規化合物 |
GB0521275D0 (en) * | 2005-10-19 | 2005-11-30 | Argenta Discovery Ltd | 3-Aminoindole compounds |
GB0524428D0 (en) | 2005-11-30 | 2006-01-11 | 7Tm Pharma As | Medicinal use of receptor ligands |
GB0525143D0 (en) * | 2005-12-09 | 2006-01-18 | Novartis Ag | Organic compounds |
US7741360B2 (en) * | 2006-05-26 | 2010-06-22 | Astrazeneca Ab | Bi-aryl or aryl-heteroaryl substituted indoles |
PL2037967T3 (pl) | 2006-06-16 | 2017-07-31 | The Trustees Of The University Of Pennsylvania | Antagoniści receptora prostaglandyny D2 w leczeniu łysienia androgenowego |
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SE0201635D0 (sv) | 2002-05-30 | 2002-05-30 | Astrazeneca Ab | Novel compounds |
TW200307542A (en) | 2002-05-30 | 2003-12-16 | Astrazeneca Ab | Novel compounds |
SE0202241D0 (sv) | 2002-07-17 | 2002-07-17 | Astrazeneca Ab | Novel Compounds |
SE0301569D0 (sv) | 2003-05-27 | 2003-05-27 | Astrazeneca Ab | Novel compounds |
SE0302232D0 (sv) | 2003-08-18 | 2003-08-18 | Astrazeneca Ab | Novel Compounds |
SE0303180D0 (sv) | 2003-11-26 | 2003-11-26 | Astrazeneca Ab | Novel compounds |
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2002
- 2002-05-30 SE SE0201635A patent/SE0201635D0/xx unknown
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- 2003-05-26 TW TW092114174A patent/TW200407305A/zh unknown
- 2003-05-27 BR BR0311494-5A patent/BR0311494A/pt not_active IP Right Cessation
- 2003-05-27 US US10/516,557 patent/US7166607B2/en not_active Expired - Fee Related
- 2003-05-27 AT AT03725970T patent/ATE501118T1/de not_active IP Right Cessation
- 2003-05-27 AU AU2003228201A patent/AU2003228201A1/en not_active Abandoned
- 2003-05-27 CA CA002487675A patent/CA2487675A1/fr not_active Abandoned
- 2003-05-27 WO PCT/SE2003/000856 patent/WO2003101961A1/fr active Application Filing
- 2003-05-27 NZ NZ536883A patent/NZ536883A/en unknown
- 2003-05-27 JP JP2004509654A patent/JP4485354B2/ja not_active Expired - Fee Related
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- 2003-05-27 MX MXPA04011876A patent/MXPA04011876A/es active IP Right Grant
- 2003-05-27 KR KR10-2004-7019452A patent/KR20050010507A/ko not_active Application Discontinuation
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- 2003-05-27 RU RU2004135064/04A patent/RU2288914C2/ru not_active IP Right Cessation
- 2003-05-27 EP EP03725970A patent/EP1513812B1/fr not_active Expired - Lifetime
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- 2003-05-27 CN CNB038183447A patent/CN100404505C/zh not_active Expired - Fee Related
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NZ536883A (en) | 2006-08-31 |
US20050165055A1 (en) | 2005-07-28 |
PL375111A1 (en) | 2005-11-28 |
RU2004135064A (ru) | 2005-08-10 |
SE0201635D0 (sv) | 2002-05-30 |
EP1513812B1 (fr) | 2011-03-09 |
ATE501118T1 (de) | 2011-03-15 |
IS7607A (is) | 2004-12-21 |
TW200407305A (en) | 2004-05-16 |
CN100404505C (zh) | 2008-07-23 |
US7166607B2 (en) | 2007-01-23 |
AU2003228201A1 (en) | 2003-12-19 |
AR039934A1 (es) | 2005-03-09 |
BR0311494A (pt) | 2005-03-29 |
CN1671659A (zh) | 2005-09-21 |
EP1513812A1 (fr) | 2005-03-16 |
ZA200409641B (en) | 2006-02-22 |
CA2487675A1 (fr) | 2003-12-11 |
MXPA04011876A (es) | 2005-03-31 |
ES2360936T3 (es) | 2011-06-10 |
KR20050010507A (ko) | 2005-01-27 |
RU2288914C2 (ru) | 2006-12-10 |
JP2005538955A (ja) | 2005-12-22 |
CO5631431A2 (es) | 2006-04-28 |
MY133624A (en) | 2007-11-30 |
WO2003101961A1 (fr) | 2003-12-11 |
JP4485354B2 (ja) | 2010-06-23 |
NO20045589L (no) | 2005-02-02 |
DE60336314D1 (de) | 2011-04-21 |
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