WO2005123671A1 - Dérivé du pyrrole - Google Patents
Dérivé du pyrrole Download PDFInfo
- Publication number
- WO2005123671A1 WO2005123671A1 PCT/JP2005/011343 JP2005011343W WO2005123671A1 WO 2005123671 A1 WO2005123671 A1 WO 2005123671A1 JP 2005011343 W JP2005011343 W JP 2005011343W WO 2005123671 A1 WO2005123671 A1 WO 2005123671A1
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- WO
- WIPO (PCT)
- Prior art keywords
- ano
- benzoi
- group
- caboad
- atom
- Prior art date
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- 150000003233 pyrroles Chemical class 0.000 title abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 33
- -1 methylenedioxyphenyl Chemical group 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 108090000623 proteins and genes Proteins 0.000 claims description 24
- 125000004429 atom Chemical group 0.000 claims description 18
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 13
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000002355 alkine group Chemical group 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 108700026220 vif Genes Proteins 0.000 claims description 4
- 241000195493 Cryptophyta Species 0.000 claims description 3
- 241000790917 Dioxys <bee> Species 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 230000036039 immunity Effects 0.000 claims description 2
- 229940126585 therapeutic drug Drugs 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 239000000049 pigment Substances 0.000 claims 1
- 230000036186 satiety Effects 0.000 claims 1
- 235000019627 satiety Nutrition 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 52
- 238000006243 chemical reaction Methods 0.000 abstract description 9
- 206010012438 Dermatitis atopic Diseases 0.000 abstract description 3
- 201000008937 atopic dermatitis Diseases 0.000 abstract description 3
- 230000004913 activation Effects 0.000 abstract description 2
- 210000000056 organ Anatomy 0.000 abstract description 2
- 238000002054 transplantation Methods 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 abstract 1
- 230000002159 abnormal effect Effects 0.000 abstract 1
- 208000026935 allergic disease Diseases 0.000 abstract 1
- 208000006673 asthma Diseases 0.000 abstract 1
- 230000002255 enzymatic effect Effects 0.000 abstract 1
- 208000024711 extrinsic asthma Diseases 0.000 abstract 1
- 208000026278 immune system disease Diseases 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 53
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 34
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 33
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 229910001868 water Inorganic materials 0.000 description 25
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 24
- 241000270322 Lepidosauria Species 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 19
- 239000000243 solution Substances 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 13
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 229910052708 sodium Inorganic materials 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 125000005605 benzo group Chemical group 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000004020 conductor Substances 0.000 description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- 239000011591 potassium Substances 0.000 description 8
- 229910052700 potassium Inorganic materials 0.000 description 8
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 description 6
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 235000001484 Trigonella foenum graecum Nutrition 0.000 description 5
- 244000250129 Trigonella foenum graecum Species 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 238000007596 consolidation process Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- GPZXFICWCMCQPF-UHFFFAOYSA-N 2-methylbenzoyl chloride Chemical compound CC1=CC=CC=C1C(Cl)=O GPZXFICWCMCQPF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000238366 Cephalopoda Species 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 230000009931 harmful effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 210000002865 immune cell Anatomy 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical group CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- WEYVCQFUGFRXOM-UHFFFAOYSA-N perazine Chemical compound C1CN(C)CCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 WEYVCQFUGFRXOM-UHFFFAOYSA-N 0.000 description 2
- 229960002195 perazine Drugs 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 125000004149 thio group Chemical group *S* 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- NALIQVLPVWZDOO-UHFFFAOYSA-N 1-$l^{1}-oxidanyloxypropane Chemical group CCCO[O] NALIQVLPVWZDOO-UHFFFAOYSA-N 0.000 description 1
- XZVGQEYEEUNMQM-UHFFFAOYSA-N 2-chloro-6,7-dihydro-5h-cyclopenta[b]pyridin-7-ol Chemical compound C1=C(Cl)N=C2C(O)CCC2=C1 XZVGQEYEEUNMQM-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- YHOYYHYBFSYOSQ-UHFFFAOYSA-N 3-methylbenzoyl chloride Chemical compound CC1=CC=CC(C(Cl)=O)=C1 YHOYYHYBFSYOSQ-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- KLYCPFXDDDMZNQ-UHFFFAOYSA-N Benzyne Chemical compound C1=CC#CC=C1 KLYCPFXDDDMZNQ-UHFFFAOYSA-N 0.000 description 1
- 101100378101 Caenorhabditis briggsae ace-4 gene Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 102100023605 Homer protein homolog 2 Human genes 0.000 description 1
- 101710147600 Homer protein homolog 2 Proteins 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 101000981993 Oncorhynchus mykiss Myelin proteolipid protein Proteins 0.000 description 1
- 241000233855 Orchidaceae Species 0.000 description 1
- 241000479842 Pella Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 241001061127 Thione Species 0.000 description 1
- WGPAQYSVWYWZKT-UHFFFAOYSA-N [C].[Ra] Chemical compound [C].[Ra] WGPAQYSVWYWZKT-UHFFFAOYSA-N 0.000 description 1
- ARVNHJBMBBFPCP-UHFFFAOYSA-L [OH-].[OH-].[Ra+2] Chemical compound [OH-].[OH-].[Ra+2] ARVNHJBMBBFPCP-UHFFFAOYSA-L 0.000 description 1
- 206010000210 abortion Diseases 0.000 description 1
- 231100000176 abortion Toxicity 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 238000003149 assay kit Methods 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- OSVHLUXLWQLPIY-KBAYOESNSA-N butyl 2-[(6aR,9R,10aR)-1-hydroxy-9-(hydroxymethyl)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl]-2-methylpropanoate Chemical compound C(CCC)OC(C(C)(C)C1=CC(=C2[C@H]3[C@H](C(OC2=C1)(C)C)CC[C@H](C3)CO)O)=O OSVHLUXLWQLPIY-KBAYOESNSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- GHLITDDQOMIBFS-UHFFFAOYSA-H cerium(3+);tricarbonate Chemical compound [Ce+3].[Ce+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O GHLITDDQOMIBFS-UHFFFAOYSA-H 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940005305 methio-form Drugs 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
-
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
-
- 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
-
- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
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- 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
- 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
- C07D405/02—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 two hetero rings
- C07D405/06—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 two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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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
- C07D409/02—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
- C07D409/06—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 carbon chain containing only aliphatic carbon 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
- 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
- C07D413/06—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 carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/02—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing not further condensed quinolizine ring systems
Definitions
- 0001 relates to a compound which inhibits nitrogen and a salt thereof.
- 002-enzyme is a gene that controls the growth and differentiation of cells, and its normal activation has been suggested to be involved.
- too many elements have been discovered, which are classified into structural, cytoplasmic, and septa types.
- Sun conductors (4), 5-anorazo conductors (5), and the like are known, but they are not disclosed having a clear structure.
- the purpose of the present invention is to provide a drug for abortion, such as an atopic dermatitis or breath, which is unreactive in organ transplantation.
- C represents an alkyne group, and represents hydrogen atom, oxygen atom, gene,
- the compound represented by the above formula wherein 2 is a hydrogen atom is a pharmaceutically acceptable salt thereof.
- the compound represented by the above formula wherein is a hydrogen atom is a pharmaceutically acceptable salt thereof.
- the picones represented by the formulas described in 5 to 4 are therapeutic drugs for immunity and algae containing a pharmaceutically acceptable salt thereof as an active ingredient.
- Inhibition of ck which is involved in the normal activity of immune cells, is useful for the treatment of animals such as atopic dermatitis, breath, etc.
- Aki group means, for example, meth, thi, pupi, isoppi, thi, isothi, eti, seti, pliers, isopenti neopenti and thi groups. It is a meth group.
- 30 aki means a cyclic aki group having 3 or more atomic atoms or a polycyclic aki group, for example, cuppi, cuti, cuppenti, ku, cuti, quochi, Examples include a biocide and an dunk group, and a dunk group is preferable.
- Zero alkay means a straight-branched alkanoyl group having 2 or more atoms, and examples thereof include thi, ppio,, iso,, and octay groups, and preferably a thi group.
- C 0 ano means a straight-chain ano group having a few atoms, such as methano, thiano, pupiano, isopropylamine, thiano. , Isothiano, e-thiano, pentiano, and thiano groups.
- C 0 ano refers to an ano group in which several straight-chained aki groups are converted into two groups, such as methano, methiano, thiano, and tipia. And ppiano groups, with preference given to methano, thiano, zipiano, and dithianosopiano groups.
- 0026 is a group having at least one oxygen atom or nitrogen atom and having a bond with 3 to 8 quacan atoms or atoms, such as di, di, di, di, ,,,,,,,, And di groups are preferable, and a di, di, di,, di, non, and oxy group are preferable.
- 0027 means C6 space, hidden C6 space, ano C6 space, C space space, C space space, C100 space, C space space.
- Pella and 26 methino groups are preferred, with preference given to methidyl, methidyl, methipellar, and benzyl pertoxy.
- Aquine is a straight-branched alkyne group with 6 atoms
- chin methine, methine, methine, methine, methine, methine, methine, methine methine, methine methine, methine methine, methine methine, methine methine, methine methine, methine methine, methine methine, methine methine, methine methine, methine methine, methine methine, methine methine, methine methine, methine methine, methine methine, methine methine It is.
- Oki C6 akim means a form in which an oxygen atom and a C6 akim group are combined, and examples thereof include oktin, oktin, and okppine group.
- the term "akio" means a form in which an akine and an oxygen atom are combined, and examples thereof include a quinoki, a methinoquino, a methinoquino, a chinoki, a ppioki, and a 22-methyl pioki group.
- C 2 aciano refers to a complex form of an alkyne atom, for example,
- Examples thereof include a cyano, a methylthio, a methylthio, a cyano, a propiano, and a 22-methylpiperano group.
- Examples of the gene include a hydrogen atom, a chlorine atom, and a hydrogen atom, and a hydrogen atom, and a hydrogen atom, a chlorine atom, and a hydrogen atom are preferable.
- the aki that has been exchanged with the four genes is the hydrogen atom on it
- ibi 4 represents a C 4 aki group in which a hydrogen atom thereon has been replaced by four genes.
- ibis, ibis, ibis and ibis are preferred, with ibis being preferred.
- Saturated means that it contains at least one oxygen atom and at least one elementary atom.
- () Ride b can be produced by reacting a conductor a with tetradran, ton, or the like, or with soppine, tothane, N-methyl, or the like.
- C can be manufactured. C can also be produced by applying methane to b.
- G CHNH (, G is a hydrogen atom, 4 toki)
- e can be produced by reacting with an atom represented by RCOCHB, such as potassium carbonate, cesium carbonate, or sodium hydrogencarbonate, such as ton or tetradran. it can.
- RCOCHB an atom represented by RCOCHB, such as potassium carbonate, cesium carbonate, or sodium hydrogencarbonate, such as ton or tetradran. it can.
- Compound h reacts with, or does not react with, or exists in, sodium or methoxide, such as methane sulphone, tonic acid, or reacts compound 9 with radium carbon, radium hydroxide, such as tetradran or methano.
- Compound h can be produced by a hydrogenation method such as
- (2 2) 2a can be obtained by hydrolysis of 2a.
- 3a which is a group represented by 005, is converted to a rosin drug such as tetras-dran
- a compound 3b is produced by adding a drug such as bokeh and reacting with a compound represented by RH (where R and R are hydrogen atoms and genes, respectively, as defined above). Can be.
- step (53) 3b can be reacted with methic acid or methionine to form compound 3c.
- RH (where, R is a hydrogen atom and a gene except from the above definition)
- X represents a group, and X represents a gene.
- 3c can be produced by reacting the alkylates 3a represented by).
- (4) 4b can be produced by reacting 4a, which is a thiol group, with iron, salt, or the like, such as methano, isopno, or methioform.
- X (where X and X represent a gene and is a C-aki group) is obtained by reacting an acylated compound represented by X.
- 5 54 d can be manufactured. Also, 4d can be produced by using an aldehyde represented by the formula C (where is the same as the above definition) instead of the formula bark as a base agent such as Sodiu or Sodium Atoki. 006 (4 4) 4b is a mixture of (3 methyl methane propyl) 3 tide, benzoto azo, etc.
- [0063] 4e can be produced by reacting the represented product.
- 14 X represents a gene. 4f can be produced by reacting the alkylates represented by ()).
- 5b which is a toki group, is treated with a bonoid such as methane or 2-octane to produce 5b.
- the medicament containing the compound of the present invention as an active ingredient can be administered systemically and topically, orally, subcutaneously, muscle, intravenously, or via the skin.
- the dose for an adult is between ⁇ and OO mg kg, which can be administered in several doses.
- the mixture was washed with te, washed (, saturated saline), dried (granium sulfate), filtered and concentrated.
- the colorless 939 was obtained by treatment with the obtained lizard color (Xanchi 955).
- tetranothium hydride (2749, 5 mmo) was added, and the mixture was heated and flowed. The mixture was returned to a warm temperature, discharged with a tube, washed (a saturated saline solution), dried (aqueous sodium sulfate), filtered and concentrated. The colorless .5 was obtained by washing with the obtained lizard color.
- Hydrogen 2 (4) H 3 (5 289 2 96 mmo) e-dano (m) calcium hydroxide (7393 mmo) was added, and the mixture was heated and flowed for 5.5 minutes. The mixture was returned to a warm temperature, discharged with a tube, washed (, saturated saline), dried (granium sulfate), filtered and concentrated. Torn lizard
- the colorless compound 4.2 was obtained by performing the reaction in (h). 2 3 to 2 °
- Tan (349, 3 mmo) and potassium carbonate (722 m9, 5.24 mmo) were added in that order, and the mixture was treated at room temperature. Water and copper were added, and the mixture was extracted, washed (, saturated saline), dried (granium sulfate), filtered and concentrated.
- the colorless compound (799) was obtained by reconstitution (thixane) with the obtained lizard color (h).
- Tano (3 m) hydroxide (2293 mmo) of an H 3 bot (79, 3 ⁇ O mo) was added, and the mixture was heated and flown for 4 hours. The mixture was returned to a warm temperature, discharged with a tube, washed (, saturated saline), dried (granium sulfate), filtered and concentrated. By re-solidifying with the obtained lizard color, the yellow .29 was obtained.
- Tan (49, 3 ⁇ mmo) and potassium carbonate (O 9, 7.34 mmo) were added to, and the mixture was allowed to stand at room temperature for 23 hours. Water and potassium were added, and the mixture was extracted, washed (, saturated saline), dried (grain water sulfate), filtered and concentrated.
- a colorless compound (987m9) was obtained by recrystallization (thixane) with a lizard color (h).
- Tonone (5 629 23 gmmo) was added at room temperature. Water and potassium were added, and the mixture was washed, washed (with saturated saline), dried (granium hydroxide), filtered and concentrated. Torn lizard
- the mixture was returned to a warm temperature, discharged with a tube, washed (, saturated saline), dried (granium sulfate), filtered and concentrated.
- the colorless compound (66) was obtained by using the obtained lizard color (thixane) and treating the obtained product with hexane.
- Tonone (332567 mmo) and potassium carbonate (975942 gmmo) were added in that order, and the mixture was cooled to room temperature.
- Tonone (28.9 gmmo) was added at room temperature. 2 more
- Tonone (289 gmmo) was treated with 6 at room temperature. Further, 2 (26 o) tonone (4 789 24 mo) was added, and the mixture was cooled to room temperature. Water and potassium were added to the mixture, and the mixture was extracted, washed (, saturated saline), dried (aqueous sodium sulfate), filtered, and concentrated.
- the cover was recombined (Tixane) with N Kage Karak NH Kage NH DM0200 (Akisha), developed siloxane 2 and then 9 to obtain a colorless compound (263).
- N-Kage-Kara-Ku NH-Kage-NH-DM020 (a formula company), developed thixane 4 and then kuhomemethano 9 to form a yellow color by re-consolidation (methano siloxane).
- the compound (3 mg) was obtained by washing with Chichome 5).
- the product is made of lizard, and is recrystallized from hexane.
- the product was obtained by using ano 2 toki 24 (2 toki) tan in place of ano 2 toki 2 (4) tan in accordance with the specifications of 4 (2 toki H pi 3 carbon).
- the mixture was added with water and water, and the mixture was extracted (, saturated saline), dried (aqueous sodium sulfate), filtered and concentrated.
- the compound (8) was obtained by reconstitution (Kuhomoxane).
- a compound was obtained by using ano2toki2 (3to4) tan instead of ano2to2 (4to) tan, and using 26 benzobenide instead of benzide.
- Figure 8 shows the physical properties of the substance.
- k25 and ATP2051 were added to a 96-ng ample and incubated at room temperature. After stopping the reaction by adding 10 phosphorus 200, the whole amount of the reaction was transferred to titanium (MAPHNB50), and the reaction was carried out at 0 M 2001.
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Abstract
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Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008105408A1 (fr) | 2007-02-26 | 2008-09-04 | Santen Pharmaceutical Co., Ltd. | Nouveau dérivé de pyrrole ayant un groupe uréide et un groupe aminocarbonyle comme substituants |
JP2009536617A (ja) * | 2006-04-11 | 2009-10-15 | バーテックス ファーマシューティカルズ インコーポレイテッド | タンパク質キナーゼの阻害剤として有用なチアゾール、イミダゾール、およびピラゾール |
WO2010024226A1 (fr) * | 2008-08-25 | 2010-03-04 | 参天製薬株式会社 | Agent prophylactique ou thérapeutique utilisé dans les maladies osseuses/articulaires comprenant, pour principe actif, un dérivé pyrrole contenant un groupe uréide, un groupe aminocarbonyle et un groupe phényle substitué comme substituants |
WO2010024227A1 (fr) | 2008-08-25 | 2010-03-04 | 参天製薬株式会社 | Nouveau dérivé de pyrrole ayant, en tant que substituants, un groupe uréide, un groupe aminocarbonyle et un groupe bicyclique qui peut avoir un substituant |
WO2011041461A3 (fr) * | 2009-10-01 | 2011-08-25 | Amira Pharmaceuticals, Inc. | Composés polycycliques utiles en tant qu'antagonistes du récepteur de l'acide lysophosphatidique |
US8217066B2 (en) | 2009-10-01 | 2012-07-10 | Amira Pharmaceuticals, Inc. | Compounds as lysophosphatidic acid receptor antagonists |
US8541587B2 (en) | 2011-04-05 | 2013-09-24 | Amira Pharmaceuticals, Inc. | Lysophosphatidic acid receptor antagonists |
US9145354B2 (en) | 2011-11-01 | 2015-09-29 | Astex Therapeutics Limited | Pharmaceutical compounds |
WO2015101670A3 (fr) * | 2014-01-03 | 2015-12-03 | Elexopharm Gmbh | Inhibiteurs des 17bêta-hydroxystéroïde déshydrogénases de type 1 et 2 |
US10532996B2 (en) | 2011-05-12 | 2020-01-14 | Proteostasis Therapeutics, Inc. | Proteostasis regulators |
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RU2485101C2 (ru) * | 2007-02-26 | 2013-06-20 | Сантен Фармасьютикал Ко., Лтд. | Новое производное пиррола, имеющее в качестве заместителей уреидную и аминокарбонильную группу |
US7977371B2 (en) | 2007-02-26 | 2011-07-12 | Santen Pharmaceutical Co., Ltd. | Pyrrole derivative having ureido group and aminocarbonyl group as substituents |
WO2008105408A1 (fr) | 2007-02-26 | 2008-09-04 | Santen Pharmaceutical Co., Ltd. | Nouveau dérivé de pyrrole ayant un groupe uréide et un groupe aminocarbonyle comme substituants |
WO2010024226A1 (fr) * | 2008-08-25 | 2010-03-04 | 参天製薬株式会社 | Agent prophylactique ou thérapeutique utilisé dans les maladies osseuses/articulaires comprenant, pour principe actif, un dérivé pyrrole contenant un groupe uréide, un groupe aminocarbonyle et un groupe phényle substitué comme substituants |
WO2010024227A1 (fr) | 2008-08-25 | 2010-03-04 | 参天製薬株式会社 | Nouveau dérivé de pyrrole ayant, en tant que substituants, un groupe uréide, un groupe aminocarbonyle et un groupe bicyclique qui peut avoir un substituant |
US8088817B2 (en) | 2008-08-25 | 2012-01-03 | Santen Pharmaceutical Co., Ltd. | Pyrrole derivative having, as substituents, ureido group, aminocarbonly group and bicyclic group which may have substituent |
WO2011041461A3 (fr) * | 2009-10-01 | 2011-08-25 | Amira Pharmaceuticals, Inc. | Composés polycycliques utiles en tant qu'antagonistes du récepteur de l'acide lysophosphatidique |
US9624182B2 (en) | 2009-10-01 | 2017-04-18 | Amira Pharmaceuticals, Inc. | Compounds as lysophosphatidic acid receptor antagonists |
JP2013506679A (ja) * | 2009-10-01 | 2013-02-28 | アミラ ファーマシューティカルス,インコーポレーテッド | リゾホスファチジン酸受容体アンタゴニストとしての多環式化合物 |
US8217066B2 (en) | 2009-10-01 | 2012-07-10 | Amira Pharmaceuticals, Inc. | Compounds as lysophosphatidic acid receptor antagonists |
US10000456B2 (en) | 2009-10-01 | 2018-06-19 | Amira Pharmaceuticals, Inc. | Polycyclic compounds as lysophosphatidic acid receptor antagonists |
US8664220B2 (en) | 2009-10-01 | 2014-03-04 | Amira Pharmaceuticals, Inc. | Polycyclic compounds as lysophosphatidic acid receptor antagonists |
US8778983B2 (en) | 2009-10-01 | 2014-07-15 | Amira Pharmaceuticals, Inc. | Polycyclic compounds as lysophosphatidic acid receptor antagonists |
US9090573B2 (en) | 2009-10-01 | 2015-07-28 | Amira Pharmaceuticals, Inc. | Compounds as lysophosphatidic acid receptor antagonists |
CN102656168A (zh) * | 2009-10-01 | 2012-09-05 | 艾米拉医药股份有限公司 | 作为溶血磷脂酸受体拮抗剂的多环化合物 |
US8541587B2 (en) | 2011-04-05 | 2013-09-24 | Amira Pharmaceuticals, Inc. | Lysophosphatidic acid receptor antagonists |
US10532996B2 (en) | 2011-05-12 | 2020-01-14 | Proteostasis Therapeutics, Inc. | Proteostasis regulators |
US9145354B2 (en) | 2011-11-01 | 2015-09-29 | Astex Therapeutics Limited | Pharmaceutical compounds |
WO2015101670A3 (fr) * | 2014-01-03 | 2015-12-03 | Elexopharm Gmbh | Inhibiteurs des 17bêta-hydroxystéroïde déshydrogénases de type 1 et 2 |
US9884839B2 (en) | 2014-01-03 | 2018-02-06 | Elexopharm Gmbh | Inhibitors of 17Beta-hydroxysteroid dehydrogenases type 1 and type 2 |
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