JP2020534308A5 - - Google Patents
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- JP2020534308A5 JP2020534308A5 JP2020516468A JP2020516468A JP2020534308A5 JP 2020534308 A5 JP2020534308 A5 JP 2020534308A5 JP 2020516468 A JP2020516468 A JP 2020516468A JP 2020516468 A JP2020516468 A JP 2020516468A JP 2020534308 A5 JP2020534308 A5 JP 2020534308A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydrothieno
- azetidine
- oxide
- ium
- tetrahydropyran
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 cyano, hydroxyl Chemical group 0.000 claims description 148
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 126
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 116
- 150000001875 compounds Chemical class 0.000 claims description 50
- 239000000203 mixture Substances 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 23
- 239000011780 sodium chloride Substances 0.000 claims description 23
- 239000012453 solvate Substances 0.000 claims description 22
- HMVYYTRDXNKRBQ-UHFFFAOYSA-N 1,3-Thiazole-4-Carboxylic Acid Chemical compound OC(=O)C1=CSC=N1 HMVYYTRDXNKRBQ-UHFFFAOYSA-N 0.000 claims description 16
- 201000004624 dermatitis Diseases 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 15
- PCXTYKGTWQCNJI-UHFFFAOYSA-N 1,2-thiazole-4-carboxylic acid Chemical compound OC(=O)C=1C=NSC=1 PCXTYKGTWQCNJI-UHFFFAOYSA-N 0.000 claims description 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 14
- AVPKHOTUOHDTLW-UHFFFAOYSA-N oxane-4-carboxylic acid Chemical compound OC(=O)C1CCOCC1 AVPKHOTUOHDTLW-UHFFFAOYSA-N 0.000 claims description 14
- 206010040799 Skin atrophy Diseases 0.000 claims description 12
- 230000032683 aging Effects 0.000 claims description 12
- 201000004384 alopecia Diseases 0.000 claims description 12
- 231100000360 alopecia Toxicity 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 231100000406 dermatitis Toxicity 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 208000006641 Skin Disease Diseases 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- HCFRWBBJISAZNK-UHFFFAOYSA-N 4-Hydroxycyclohexylcarboxylic acid Chemical compound OC1CCC(C(O)=O)CC1 HCFRWBBJISAZNK-UHFFFAOYSA-N 0.000 claims description 6
- 206010000496 Acne Diseases 0.000 claims description 6
- 208000010247 Contact Dermatitis Diseases 0.000 claims description 6
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 6
- 206010012442 Dermatitis contact Diseases 0.000 claims description 6
- 208000005679 Eczema Diseases 0.000 claims description 6
- 206010061218 Inflammation Diseases 0.000 claims description 6
- 208000003251 Pruritus Diseases 0.000 claims description 6
- 208000008742 Seborrheic Dermatitis Diseases 0.000 claims description 6
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 claims description 6
- 210000003491 Skin Anatomy 0.000 claims description 6
- 206010046736 Urticarias Diseases 0.000 claims description 6
- 201000008937 atopic dermatitis Diseases 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 231100000080 dermatitis contact Toxicity 0.000 claims description 6
- 231100001003 eczema Toxicity 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 230000002757 inflammatory Effects 0.000 claims description 6
- 230000004054 inflammatory process Effects 0.000 claims description 6
- 230000002062 proliferating Effects 0.000 claims description 6
- 201000004681 psoriasis Diseases 0.000 claims description 6
- 150000003431 steroids Chemical class 0.000 claims description 6
- 125000004434 sulfur atoms Chemical group 0.000 claims description 6
- 108060002038 Pde4 Proteins 0.000 claims description 5
- 150000004677 hydrates Chemical class 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- HONIICLYMWZJFZ-UHFFFAOYSA-N Azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 4
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N P-Anisic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 claims description 4
- LPNBBFKOUUSUDB-UHFFFAOYSA-N P-Toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- RPJRJUVGGDVVDF-UHFFFAOYSA-N 1,1-dioxothiane-4-carboxylic acid Chemical compound OC(=O)C1CCS(=O)(=O)CC1 RPJRJUVGGDVVDF-UHFFFAOYSA-N 0.000 claims description 2
- GGYXPOOZYZHPLB-UHFFFAOYSA-N 1,2-thiazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=NS1 GGYXPOOZYZHPLB-UHFFFAOYSA-N 0.000 claims description 2
- PXRXGHUTKHXUGF-UHFFFAOYSA-N 1,5-dimethylpyrazole-3-carboxylic acid Chemical compound CC1=CC(C(O)=O)=NN1C PXRXGHUTKHXUGF-UHFFFAOYSA-N 0.000 claims description 2
- FRBBOXGMTKVHBW-UHFFFAOYSA-N 1-(dimethylcarbamoyl)piperidine-4-carboxylic acid Chemical compound CN(C)C(=O)N1CCC(C(O)=O)CC1 FRBBOXGMTKVHBW-UHFFFAOYSA-N 0.000 claims description 2
- WFCLWJHOKCQYOQ-UHFFFAOYSA-N 1-acetylpiperidine-4-carboxylic acid Chemical compound CC(=O)N1CCC(C(O)=O)CC1 WFCLWJHOKCQYOQ-UHFFFAOYSA-N 0.000 claims description 2
- YRKRPSDCHZQNDF-UHFFFAOYSA-N 1-ethylpyrazole-3-carboxylic acid Chemical compound CCN1C=CC(C(O)=O)=N1 YRKRPSDCHZQNDF-UHFFFAOYSA-N 0.000 claims description 2
- BXXOXFNLGLMZSO-UHFFFAOYSA-N 1-ethylpyrazole-4-carboxylic acid Chemical compound CCN1C=C(C(O)=O)C=N1 BXXOXFNLGLMZSO-UHFFFAOYSA-N 0.000 claims description 2
- YBFIKNNFQIBIQZ-UHFFFAOYSA-N 1-methyl-pyrazole-3-carboxylic acid Chemical compound CN1C=CC(C(O)=O)=N1 YBFIKNNFQIBIQZ-UHFFFAOYSA-N 0.000 claims description 2
- UPPPWUOZCSMDTR-UHFFFAOYSA-N 1-methyl-pyrazole-4-carboxylic acid Chemical compound CN1C=C(C(O)=O)C=N1 UPPPWUOZCSMDTR-UHFFFAOYSA-N 0.000 claims description 2
- WZTRQGJMMHMFGH-UHFFFAOYSA-N 1-methylimidazole-4-carboxylic acid Chemical compound CN1C=NC(C(O)=O)=C1 WZTRQGJMMHMFGH-UHFFFAOYSA-N 0.000 claims description 2
- JRJLLMLYUFAZOM-UHFFFAOYSA-N 2,6-dimethylpyridine-4-carboxylic acid Chemical compound CC1=CC(C(O)=O)=CC(C)=N1 JRJLLMLYUFAZOM-UHFFFAOYSA-N 0.000 claims description 2
- OFMZDYDHETWLMA-UHFFFAOYSA-N 2-ethyl-1,3-oxazole-4-carboxylic acid Chemical compound CCC1=NC(C(O)=O)=CO1 OFMZDYDHETWLMA-UHFFFAOYSA-N 0.000 claims description 2
- NMBMFJUWTJAVBG-UHFFFAOYSA-N 2-ethyl-1,3-thiazole-4-carboxylic acid Chemical compound CCC1=NC(C(O)=O)=CS1 NMBMFJUWTJAVBG-UHFFFAOYSA-N 0.000 claims description 2
- NSTREUWFTAOOKS-UHFFFAOYSA-N 2-fluorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1F NSTREUWFTAOOKS-UHFFFAOYSA-N 0.000 claims description 2
- IARMCEYEYXXEOS-UHFFFAOYSA-N 2-methyl-1,3-oxazole-4-carboxylic acid Chemical compound CC1=NC(C(O)=O)=CO1 IARMCEYEYXXEOS-UHFFFAOYSA-N 0.000 claims description 2
- MARKCZHBQSQUHU-UHFFFAOYSA-N 2-methyl-1,3-oxazole-5-carboxylic acid Chemical compound CC1=NC=C(C(O)=O)O1 MARKCZHBQSQUHU-UHFFFAOYSA-N 0.000 claims description 2
- ZHDRDZMTEOIWSX-UHFFFAOYSA-N 2-methyl-1,3-thiazole-4-carboxylic acid Chemical compound CC1=NC(C(O)=O)=CS1 ZHDRDZMTEOIWSX-UHFFFAOYSA-N 0.000 claims description 2
- QCXCIYPOMMIBHO-UHFFFAOYSA-N 2-methyl-1,3-thiazole-5-carboxylic acid Chemical compound CC1=NC=C(C(O)=O)S1 QCXCIYPOMMIBHO-UHFFFAOYSA-N 0.000 claims description 2
- NMGIXZFBQPETOK-UHFFFAOYSA-N 2-methylpyrimidine-5-carboxylic acid Chemical compound CC1=NC=C(C(O)=O)C=N1 NMGIXZFBQPETOK-UHFFFAOYSA-N 0.000 claims description 2
- CAOMCZAIALVUPA-UHFFFAOYSA-N 3-(methylthio)propionic acid Chemical compound CSCCC(O)=O CAOMCZAIALVUPA-UHFFFAOYSA-N 0.000 claims description 2
- VOIZNVUXCQLQHS-UHFFFAOYSA-N 3-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC(Br)=C1 VOIZNVUXCQLQHS-UHFFFAOYSA-N 0.000 claims description 2
- VMVZOLNGJGAOET-UHFFFAOYSA-N 3-ethylsulfonylbenzoic acid Chemical compound CCS(=O)(=O)C1=CC=CC(C(O)=O)=C1 VMVZOLNGJGAOET-UHFFFAOYSA-N 0.000 claims description 2
- ZSHGVMYLGGANKU-UHFFFAOYSA-N 3-hydroxycyclobutane-1-carboxylic acid Chemical compound OC1CC(C(O)=O)C1 ZSHGVMYLGGANKU-UHFFFAOYSA-N 0.000 claims description 2
- XHQZJYCNDZAGLW-UHFFFAOYSA-N 3-methoxybenzoic acid Chemical compound COC1=CC=CC(C(O)=O)=C1 XHQZJYCNDZAGLW-UHFFFAOYSA-N 0.000 claims description 2
- YSIKHBWUBSFBRZ-UHFFFAOYSA-N 3-methoxypropanoic acid Chemical compound COCCC(O)=O YSIKHBWUBSFBRZ-UHFFFAOYSA-N 0.000 claims description 2
- YANZAAFELHVNQZ-UHFFFAOYSA-N 3-methyl-1,2-thiazole-5-carboxylic acid Chemical compound CC=1C=C(C(O)=O)SN=1 YANZAAFELHVNQZ-UHFFFAOYSA-N 0.000 claims description 2
- ODUCCTTZGHSNKX-UHFFFAOYSA-N 3-methylsulfonylpropanoic acid Chemical compound CS(=O)(=O)CCC(O)=O ODUCCTTZGHSNKX-UHFFFAOYSA-N 0.000 claims description 2
- XFZWBJNMCIHLLI-UHFFFAOYSA-N 3-propan-2-ylsulfonylbenzoic acid Chemical compound CC(C)S(=O)(=O)C1=CC=CC(C(O)=O)=C1 XFZWBJNMCIHLLI-UHFFFAOYSA-N 0.000 claims description 2
- LHIJETBHEKJGOK-UHFFFAOYSA-N 4-(dimethylcarbamoyl)benzoic acid Chemical compound CN(C)C(=O)C1=CC=C(C(O)=O)C=C1 LHIJETBHEKJGOK-UHFFFAOYSA-N 0.000 claims description 2
- ZYTCRZMJZJPYEG-UHFFFAOYSA-N 4-(methylcarbamoyl)benzoic acid Chemical compound CNC(=O)C1=CC=C(C(O)=O)C=C1 ZYTCRZMJZJPYEG-UHFFFAOYSA-N 0.000 claims description 2
- PAOYGUDKABVANA-UHFFFAOYSA-N 4-(methylsulfamoyl)benzoic acid Chemical compound CNS(=O)(=O)C1=CC=C(C(O)=O)C=C1 PAOYGUDKABVANA-UHFFFAOYSA-N 0.000 claims description 2
- BFTPXPCTGHARJF-UHFFFAOYSA-N 4-(morpholine-4-carbonyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)N1CCOCC1 BFTPXPCTGHARJF-UHFFFAOYSA-N 0.000 claims description 2
- QBHDSQZASIBAAI-UHFFFAOYSA-N 4-acetylbenzoic acid Chemical compound CC(=O)C1=CC=C(C(O)=O)C=C1 QBHDSQZASIBAAI-UHFFFAOYSA-N 0.000 claims description 2
- HILDSQMINZBXHC-UHFFFAOYSA-N 4-cyclopentylsulfonylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1S(=O)(=O)C1CCCC1 HILDSQMINZBXHC-UHFFFAOYSA-N 0.000 claims description 2
- IOMGTNZQTBFAHK-UHFFFAOYSA-N 4-ethylsulfonylbenzoic acid Chemical compound CCS(=O)(=O)C1=CC=C(C(O)=O)C=C1 IOMGTNZQTBFAHK-UHFFFAOYSA-N 0.000 claims description 2
- AJBWNNKDUMXZLM-UHFFFAOYSA-N 4-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=C(C(O)=O)C=C1 AJBWNNKDUMXZLM-UHFFFAOYSA-N 0.000 claims description 2
- BOJGIPHAFYLYRH-UHFFFAOYSA-N 4-propan-2-ylsulfonylbenzoic acid Chemical compound CC(C)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 BOJGIPHAFYLYRH-UHFFFAOYSA-N 0.000 claims description 2
- UXDZNQXVCFIDJL-UHFFFAOYSA-N 5-ethyl-1-methylpyrazole-3-carboxylic acid Chemical compound CCC1=CC(C(O)=O)=NN1C UXDZNQXVCFIDJL-UHFFFAOYSA-N 0.000 claims description 2
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N M-Toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 claims description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N O-Toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims description 2
- 230000002730 additional Effects 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 2
- 235000001968 nicotinic acid Nutrition 0.000 claims description 2
- 239000011664 nicotinic acid Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims description 2
- IIKFXOLJMNWWCH-UHFFFAOYSA-N piperidine-1,4-dicarboxylic acid Chemical compound OC(=O)C1CCN(C(O)=O)CC1 IIKFXOLJMNWWCH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 239000003981 vehicle Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 4
- 229940079593 drugs Drugs 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- GMWFCJXSQQHBPI-UHFFFAOYSA-N azetidin-3-ol Chemical compound OC1CNC1 GMWFCJXSQQHBPI-UHFFFAOYSA-N 0.000 description 1
Description
第ïŒïŒé
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Claims (18)
- äžè¬åŒïŒïŒ©ïŒïŒ
1ã¯ãæ°ŽçŽ ãŸãã¯(1ã4)ã¢ã«ãã«ã§ããïŒ
2ã¯ãããã©ããããã©ãã«ããªããµã¹ããããã¿ãã«ããããªãžãã«ããã³ãããªãžãã«ãããªã矀ããéžæããïŒããã§ã該ãããªãžãã«ããã³è©²ãããªãžãã«ã¯ãç¬ç«ããŠïŒ²4ããéžæãããïŒå以äžã®çœ®æåºã§çœ®æãããŠããŠãããïŒ
4ã¯ãâ()(1ã4)ã¢ã«ãã«ã(1ã4)ã¢ã«ãã«ãâ()2xãâ()2abãâ()(1ã6)ã¢ã«ãã«ãâ()abããã³â(1ã4)ã¢ã«ãã«â()abãããªã矀ããéžæããïŒ
aããã³ïŒ²bã¯ãç¬ç«ããŠãæ°ŽçŽ ã(1ã4)ã¢ã«ãã«ããã³ãã(1ã4)ã¢ã«ãã«ãããªã矀ããéžæããããããŸãã¯
aããã³ïŒ²bã¯ãããããçµåããŠããçªçŽ ååãšäžç·ã«ãªã£ãŠ(ïŒãïŒ)å¡ãããã·ã¯ãã¢ã«ãã«ã圢æããŠããããããã§ã該ãããã·ã¯ãã¢ã«ãã«ã¯ãïŒå以äžã®(1ã4)ã¢ã«ãã«ã§çœ®æãããŠããŠãããïŒ
3ã¯ã(1ã6)ã¢ã«ãã«ã(3ã6)ã·ã¯ãã¢ã«ãã«ã(1ã4)ã¢ã«ãã«(3ã6)ã·ã¯ãã¢ã«ãã«ããã(1ã6)ã¢ã«ãã«ã(1ã6)ã¢ã«ã³ãã·ã(1ã6)ã¢ã«ãã«(1ã6)ã¢ã«ã³ãã·ããã(1ã4)ã¢ã«ãã«ãªãã·ã(ïŒãïŒ)å¡ãããã·ã¯ãã¢ã«ãã«ã(1ã4)ã¢ã«ãã«(ïŒãïŒ)å¡ãããã·ã¯ãã¢ã«ãã«ã(ïŒãïŒ)å¡ãããã¢ãªãŒã«ã(1ã4)ã¢ã«ãã«(ïŒãïŒ)å¡ãããã¢ãªãŒã«ãã¢ãªãŒã«ããã³(1ã4)ã¢ã«ãã«ã¢ãªãŒã«ãããªã矀ããéžæããïŒããã§ã該ã¢ã«ãã«ã該ã·ã¯ãã¢ã«ãã«ã該ãããã·ã¯ãã¢ã«ãã«ã該ãããã¢ãªãŒã«ããã³è©²ã¢ãªãŒã«ã¯ãç¬ç«ããŠïŒ²5ããéžæãããïŒå以äžã®çœ®æåºã§çœ®æãããŠããŠãããïŒ
5ã¯ãããã²ã³ãã·ã¢ããããããã·ã«ã(1ã4)ã¢ã«ãã«ããã(1ã4)ã¢ã«ãã«ããã(1ã4)ã¢ã«ãã«ãªãã·ãxãâxãâ()2xãâ()2abãâ()xãâ()(x)ãããã³â()abãããªã矀ããéžæããïŒ
xã¯ã(1ã4)ã¢ã«ãã«ã(3ã6)ã·ã¯ãã¢ã«ãã«ããããã·ã¯ãã¢ã«ãã«ãããªãïŒ
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ã§ç€ºãããè«æ±é ïŒèšèŒã®ååç©ããŸãã¯ãã®è¬åŠçã«èš±å®¹ãããå¡©ããšãã³ããªããŒããšãã³ããªããŒæ··åç©ããžã¢ã¹ãã¬ãªããŒããžã¢ã¹ãã¬ãªããŒæ··åç©ãæ°Žåç©ãããã¯æº¶åªåç©ã - äžè¬åŒïŒïŒ©ïŒ©ïœïŒïŒ
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ã§ç€ºãããè«æ±é ïŒãŸãã¯ïŒèšèŒã®ååç©ããŸãã¯ãã®è¬åŠçã«èš±å®¹ãããå¡©ããšãã³ããªããŒããšãã³ããªããŒæ··åç©ãæ°Žåç©ãããã¯æº¶åªåç©ã - 1ããæ°ŽçŽ ãŸãã¯ã¡ãã«ã§ãããè«æ±é ïŒãïŒããããïŒé èšèŒã®ååç©ããŸãã¯ãã®è¬åŠçã«èš±å®¹ãããå¡©ããšãã³ããªããŒããšãã³ããªããŒæ··åç©ãæ°Žåç©ãããã¯æº¶åªåç©ã
- 3ãã(3ã6)ã·ã¯ãã¢ã«ãã«ã(ïŒãïŒ)å¡ãããã·ã¯ãã¢ã«ãã«ãããã³(ïŒãïŒ)å¡ãããã¢ãªãŒã«ãããªã矀ããéžæããããè«æ±é ïŒãïŒããããïŒé èšèŒã®ååç©ããŸãã¯ãã®è¬åŠçã«èš±å®¹ãããå¡©ããšãã³ããªããŒããšãã³ããªããŒæ··åç©ãæ°Žåç©ãããã¯æº¶åªåç©ã
- ã€ãœãã¢ãŸãŒã«âïŒâã«ã«ãã³é ž[ïŒâ[(ïŒïŒ²)âïŒâãªãã·ãâïŒâ(ããã©ããããã©ã³âïŒâã€ã«ã¢ãã)âïŒ,ïŒâãžãããããšã[ïŒ,ïŒâïœ]ããªããžã³âïŒâã€ãŠã âïŒâã€ã«]ã¢ãŒããžã³âïŒâã€ã«]ïŒååç©ïŒïŒïŒïœïŒã
ãã¢ãŸãŒã«âïŒâã«ã«ãã³é ž[ïŒâ[(ïŒïŒ²)âïŒâãªãã·ãâïŒâ(ããã©ããããã©ã³âïŒâã€ã«ã¢ãã)âïŒ,ïŒâãžãããããšã[ïŒ,ïŒâïœ]ããªããžã³âïŒâã€ãŠã âïŒâã€ã«]ã¢ãŒããžã³âïŒâã€ã«]ïŒååç©ïŒïŒïŒïœïŒã
ã€ãœãã¢ãŸãŒã«âïŒâã«ã«ãã³é ž[ïŒâ[ïŒâ[ã¡ãã«(ããã©ããããã©ã³âïŒâã€ã«)ã¢ãã]âïŒâãªãã·ãâïŒ,ïŒâãžãããããšã[ïŒ,ïŒâïœ]ããªããžã³âïŒâã€ãŠã âïŒâã€ã«]ã¢ãŒããžã³âïŒâã€ã«]ïŒååç©ïŒïŒïŒïŒã
ã€ãœãã¢ãŸãŒã«âïŒâã«ã«ãã³é ž[ïŒâ[(ïŒïŒ²)âïŒâ[ã¡ãã«(ããã©ããããã©ã³âïŒâã€ã«)ã¢ãã]âïŒâãªãã·ãâïŒ,ïŒâãžãããããšã[ïŒ,ïŒâïœ]ããªããžã³âïŒâã€ãŠã âïŒâã€ã«]ã¢ãŒããžã³âïŒâã€ã«]ïŒååç©ïŒïŒïŒïœïŒã
ãã¢ãŸãŒã«âïŒâã«ã«ãã³é ž[ïŒâ[ïŒâ[ã¡ãã«(ããã©ããããã©ã³âïŒâã€ã«)ã¢ãã]âïŒâãªãã·ãâïŒ,ïŒâãžãããããšã[ïŒ,ïŒâïœ]ããªããžã³âïŒâã€ãŠã âïŒâã€ã«]ã¢ãŒããžã³âïŒâã€ã«]ïŒååç©ïŒïŒïŒïŒã
ãã¢ãŸãŒã«âïŒâã«ã«ãã³é ž[ïŒâ[(ïŒïŒ²)âïŒâ[ã¡ãã«(ããã©ããããã©ã³âïŒâã€ã«)ã¢ãã]âïŒâãªãã·ãâïŒ,ïŒâãžãããããšã[ïŒ,ïŒâïœ]ããªããžã³âïŒâã€ãŠã âïŒâã€ã«]ã¢ãŒããžã³âïŒâã€ã«]ïŒååç©ïŒïŒïŒïœïŒ
ãããªã矀ããéžæããããè«æ±é ïŒãïŒããããïŒé èšèŒã®ååç©ããŸãã¯ãã®è¬åŠçã«èš±å®¹ãããå¡©ããšãã³ããªããŒããšãã³ããªããŒã®æ··åç©ãæ°Žåç©ãããã¯æº¶åªåç©ã - ã·ã¯ããã³ã¿ã³ã«ã«ãã³é ž[ïŒâ[(ïŒïŒ²)âïŒâãªãã·ãâïŒâ(ããã©ããããã©ã³âïŒâã€ã«ã¢ãã)âïŒ,ïŒâãžãããããšã[ïŒ,ïŒâïœ]ããªããžã³âïŒâã€ãŠã âïŒâã€ã«]ã¢ãŒããžã³âïŒâã€ã«]ã
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- ç®èçŸæ£ãŸãã¯ç¶æ ãåŠçœ®ãŸãã¯å¯è§£ããããã®å»è¬ã§ãã£ãŠãè¬åŠçã«èš±å®¹ãããæ äœãŸãã¯ïŒçš®é¡ä»¥äžã®è³Šåœ¢å€ãšäžç·ã«ã§ãã£ãŠããããä»ã®æ²»ç掻æ§ååç©ãšçµã¿åãããŠã§ãã£ãŠããããè«æ±é ïŒãïŒããããïŒé èšèŒã®ïŒçš®é¡ä»¥äžã®ååç©ãŸãã¯ãã®è¬åŠçã«èš±å®¹ãããå¡©ããšãã³ããªããŒããšãã³ããªããŒã®æ··åç©ãæ°Žåç©ãããã¯æº¶åªåç©ãå«ããå»è¬ã
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AU2002364211A1 (en) | 2001-12-21 | 2003-07-15 | Bayer Pharmaceuticals Corporation | Thienopyrimidine derivative compounds as inhibitors of prolylpeptidase, inducers of apoptosis and cancer treatment agents |
CA2637245A1 (en) | 2006-01-17 | 2007-07-26 | Signal Pharmaceuticals, Llc | Inhibitors of tnf.alpha., pde4 and b-raf, compositions thereof and methods of use therewith |
EP1847543A1 (de) | 2006-04-19 | 2007-10-24 | Boehringer Ingelheim Pharma GmbH & Co. KG | Dihydrothienopyrimidine zur Behandlung von entzÃŒndlichen Erkrankungen |
PT1874781E (pt) | 2006-04-19 | 2009-07-27 | Boehringer Ingelheim Int | Di-hidro-tienopirimidinas para o tratamento de doenças inflamatórias |
BRPI0818006B8 (pt) | 2007-10-19 | 2021-05-25 | Boehringer Ingelheim Int | compostos de piperidino-di-hidrotienopirimidinas substituÃdas, uso dos mesmos e formulações farmacêuticas |
JP2011500621A (ja) | 2007-10-19 | 2011-01-06 | ããŒãªã³ã¬ãŒ ã€ã³ã²ã«ãã€ã ã€ã³ã¿ãŒãã·ã§ãã« ã²ãŒã«ã·ã£ãã ããã ãã·ã¥ã¬ã³ã¯ãã« ãããã³ã° | æ°èŠãã§ãã«çœ®æããã©ãžãâãžãããããšãããªããžã³ |
ATE537175T1 (de) | 2007-10-19 | 2011-12-15 | Boehringer Ingelheim Int | Neue piperazino-dihydrothienopyrimidin-derivate |
WO2009050242A2 (de) | 2007-10-19 | 2009-04-23 | Boehringer Ingelheim International Gmbh | Heterocyclus-substituierte piperazino-dihydrothienopyrimidine |
CA2753604A1 (en) | 2009-02-27 | 2010-09-02 | Boehringer Ingelheim International Gmbh | Drug combinations containing pde4-inhibitors and nsaids |
JP2013515740A (ja) | 2009-12-23 | 2013-05-09 | ãã€ãªã¯ã©ã€ã¹ã ãã¡ãŒãã·ã¥ãŒãã£ã«ã«ãºïŒ ã€ã³ã³ãŒãã¬ã€ããã | ïœïœïœïœãããŒãŒã€ã³ããã¿ãŒãšããŠã®è€çŽ ç°åŒååç© |
JP2013523792A (ja) | 2010-04-08 | 2013-06-17 | ããŒãªã³ã¬ãŒ ã€ã³ã²ã«ãã€ã ã€ã³ã¿ãŒãã·ã§ãã« ã²ãŒã«ã·ã£ãã ããã ãã·ã¥ã¬ã³ã¯ãã« ãããã³ã° | ïœïœ ïŒé»å®³å€åã³ïœ ïœïŒå容äœã¢ã³ã¿ãŽãã¹ããå«æããå»è¬ã®çµã¿åãã |
RS55624B1 (sr) | 2011-02-07 | 2017-06-30 | Scipharm SÃ rl | Nova kompozicija za leÄenje cistiÄne fibroze |
US20130059866A1 (en) | 2011-08-24 | 2013-03-07 | Boehringer Ingelheim International Gmbh | Novel piperidino-dihydrothienopyrimidine sulfoxides and their use for treating copd and asthma |
KR102189560B1 (ko) | 2012-10-25 | 2020-12-11 | í ížëŒ ëì€ì»€ë²ëŠ¬ íížëì€ ìììš | Pde4 ì í€í ë¡ì늎 ì íŽì |
WO2014124860A1 (en) | 2013-02-14 | 2014-08-21 | Boehringer Ingelheim International Gmbh | Specific pde4b-inhibitors for the treatment of diabetes mellitus |
JP7216719B2 (ja) * | 2017-09-20 | 2023-02-01 | ãŠããªã³ã»ã»ã©ãã¥ãŒãã£ã¯ã¹ã»ã¢ã¯ãã£ãšã»ã«ã¹ã«ã | 眮æãžãããããšãããªããžã³ããã³ãã¹ããžãšã¹ãã©ãŒãŒé»å®³å€ãšããŠã®ãã®äœ¿çš |
JP7203846B2 (ja) | 2017-12-15 | 2023-01-13 | ãŠããªã³ã»ã»ã©ãã¥ãŒãã£ã¯ã¹ã»ã¢ã¯ãã£ãšã»ã«ã¹ã«ã | 眮æã¢ãŒããžã³ãžãããããšãããªãžã³ããã³ãã¹ããžãšã¹ãã©ãŒãŒé»å®³å€ãšããŠã®ãããã®äœ¿çš |
JP7198820B2 (ja) | 2017-12-15 | 2023-01-04 | ãŠããªã³ã»ã»ã©ãã¥ãŒãã£ã¯ã¹ã»ã¢ã¯ãã£ãšã»ã«ã¹ã«ã | 眮æã¢ãŒããžã³ãžãããããšãããªããžã³ããã³ãã¹ããžãšã¹ãã©ãŒãŒé»å®³å€ãšããŠã®ãããã®äœ¿çš |
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