JP4782342B2 - フェノキシプロパノールアミン類、それらの製造方法およびそれらを含む医薬組成物 - Google Patents
フェノキシプロパノールアミン類、それらの製造方法およびそれらを含む医薬組成物 Download PDFInfo
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- JP4782342B2 JP4782342B2 JP2001544882A JP2001544882A JP4782342B2 JP 4782342 B2 JP4782342 B2 JP 4782342B2 JP 2001544882 A JP2001544882 A JP 2001544882A JP 2001544882 A JP2001544882 A JP 2001544882A JP 4782342 B2 JP4782342 B2 JP 4782342B2
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- Japan
- Prior art keywords
- alkyl
- phenoxy
- propanol
- hydroxy
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 238000000034 method Methods 0.000 title claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 title abstract description 6
- 238000004519 manufacturing process Methods 0.000 title description 33
- 150000001875 compounds Chemical class 0.000 claims abstract description 97
- 238000002360 preparation method Methods 0.000 claims abstract description 57
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 125000005843 halogen group Chemical group 0.000 claims abstract description 12
- 239000012453 solvate Substances 0.000 claims abstract description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 16
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
- -1 4-ethoxycarbonylphenylmethyl Chemical group 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- 229960004592 isopropanol Drugs 0.000 claims description 18
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 13
- 125000006239 protecting group Chemical group 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- WOTZFWTUWUQBLQ-FQEVSTJZSA-N ethyl 4-[4-[[(2s)-2-hydroxy-3-[4-hydroxy-3-(methylsulfamoyl)phenoxy]propyl]amino]piperidin-1-yl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N1CCC(NC[C@H](O)COC=2C=C(C(O)=CC=2)S(=O)(=O)NC)CC1 WOTZFWTUWUQBLQ-FQEVSTJZSA-N 0.000 claims description 2
- JFPMKBJCQKRRMC-QFIPXVFZSA-N ethyl 4-[4-[[(2s)-2-hydroxy-3-[4-hydroxy-3-(propylsulfonylamino)phenoxy]propyl]amino]piperidin-1-yl]benzoate Chemical compound C1=C(O)C(NS(=O)(=O)CCC)=CC(OC[C@@H](O)CNC2CCN(CC2)C=2C=CC(=CC=2)C(=O)OCC)=C1 JFPMKBJCQKRRMC-QFIPXVFZSA-N 0.000 claims description 2
- MRTINNCFOIVQPO-NRFANRHFSA-N ethyl 4-[4-[[[(2s)-2-hydroxy-3-[4-hydroxy-3-(methanesulfonamido)phenoxy]propyl]amino]methyl]piperidin-1-yl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N1CCC(CNC[C@H](O)COC=2C=C(NS(C)(=O)=O)C(O)=CC=2)CC1 MRTINNCFOIVQPO-NRFANRHFSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- JJRINQOHYYDQBX-SUHMBNCMSA-N n-[4-[2-[[(2s)-2-hydroxy-3-[4-hydroxy-3-(methanesulfonamido)phenoxy]propyl]amino]piperidin-1-yl]phenyl]-4-propan-2-ylbenzenesulfonamide Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)NC1=CC=C(N2C(CCCC2)NC[C@H](O)COC=2C=C(NS(C)(=O)=O)C(O)=CC=2)C=C1 JJRINQOHYYDQBX-SUHMBNCMSA-N 0.000 claims description 2
- VWMBXJFXWFYPFO-IBGZPJMESA-N n-[5-[(2s)-3-[[1-(4-cyanophenyl)piperidin-4-yl]amino]-2-hydroxypropoxy]-2-hydroxyphenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC(OC[C@@H](O)CNC2CCN(CC2)C=2C=CC(=CC=2)C#N)=C1 VWMBXJFXWFYPFO-IBGZPJMESA-N 0.000 claims description 2
- QMPLQMSXKMRVAL-NRFANRHFSA-N tert-butyl 4-[4-[[(2s)-2-hydroxy-3-[4-hydroxy-3-(methanesulfonamido)phenoxy]propyl]amino]piperidin-1-yl]benzoate Chemical compound C1=CC(C(=O)OC(C)(C)C)=CC=C1N1CCC(NC[C@H](O)COC=2C=C(NS(C)(=O)=O)C(O)=CC=2)CC1 QMPLQMSXKMRVAL-NRFANRHFSA-N 0.000 claims description 2
- MXKMYDLASXNPAP-YMQLSTQVSA-N 4-bromo-n-[4-[2-[[(2s)-2-hydroxy-3-[4-hydroxy-3-(methanesulfonamido)phenoxy]propyl]amino]piperidin-1-yl]phenyl]benzenesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC(OC[C@@H](O)CNC2N(CCCC2)C=2C=CC(NS(=O)(=O)C=3C=CC(Br)=CC=3)=CC=2)=C1 MXKMYDLASXNPAP-YMQLSTQVSA-N 0.000 claims 1
- 125000003865 brosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)S(*)(=O)=O 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 132
- 239000000047 product Substances 0.000 description 91
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 75
- 239000000203 mixture Substances 0.000 description 60
- 239000002904 solvent Substances 0.000 description 53
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- 238000003818 flash chromatography Methods 0.000 description 21
- 239000000463 material Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000002585 base Substances 0.000 description 16
- 238000010992 reflux Methods 0.000 description 14
- 239000007795 chemical reaction product Substances 0.000 description 13
- 239000004480 active ingredient Substances 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- 238000011282 treatment Methods 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 102000016959 beta-3 Adrenergic Receptors Human genes 0.000 description 3
- 108010014502 beta-3 Adrenergic Receptors Proteins 0.000 description 3
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000003599 food sweetener Nutrition 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000003765 sweetening agent Substances 0.000 description 3
- FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 0.000 description 3
- ZKPFWJHJJVCVAJ-UHFFFAOYSA-N 2-[(3-methylsulfinyl-4-phenylmethoxyphenoxy)methyl]oxirane Chemical compound C=1C=C(OCC=2C=CC=CC=2)C(S(=O)C)=CC=1OCC1CO1 ZKPFWJHJJVCVAJ-UHFFFAOYSA-N 0.000 description 2
- BYDXZYUGDXYSJY-UHFFFAOYSA-N 2-[(4-phenylmethoxyphenoxy)methyl]oxirane Chemical compound C1OC1COC(C=C1)=CC=C1OCC1=CC=CC=C1 BYDXZYUGDXYSJY-UHFFFAOYSA-N 0.000 description 2
- XDHMIZDZJOFRNL-UHFFFAOYSA-N 4-(4-aminopiperidin-1-yl)-n,n-diethylbenzamide;dihydrochloride Chemical compound Cl.Cl.C1=CC(C(=O)N(CC)CC)=CC=C1N1CCC(N)CC1 XDHMIZDZJOFRNL-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- PYGLCZHFNYYYTJ-UHFFFAOYSA-N 4-bromo-n-[6-[4-[[2-hydroxy-3-(4-hydroxy-3-methylsulfinylphenoxy)propyl]amino]piperidin-1-yl]pyridin-3-yl]benzenesulfonamide Chemical compound C1=C(O)C(S(=O)C)=CC(OCC(O)CNC2CCN(CC2)C=2N=CC(NS(=O)(=O)C=3C=CC(Br)=CC=3)=CC=2)=C1 PYGLCZHFNYYYTJ-UHFFFAOYSA-N 0.000 description 2
- CETRNHJIXGITKR-UHFFFAOYSA-N 4-propan-2-ylbenzenesulfonyl chloride Chemical compound CC(C)C1=CC=C(S(Cl)(=O)=O)C=C1 CETRNHJIXGITKR-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 208000008589 Obesity Diseases 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 230000001270 agonistic effect Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000003178 anti-diabetic effect Effects 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- MSSMZGTYKHJEMZ-JOCHJYFZSA-N benzyl n-methylsulfonyl-n-[5-[[(2s)-oxiran-2-yl]methoxy]-2-phenylmethoxyphenyl]carbamate Chemical compound C=1C(OC[C@H]2OC2)=CC=C(OCC=2C=CC=CC=2)C=1N(S(=O)(=O)C)C(=O)OCC1=CC=CC=C1 MSSMZGTYKHJEMZ-JOCHJYFZSA-N 0.000 description 2
- 238000010256 biochemical assay Methods 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- WEDIIKBPDQQQJU-UHFFFAOYSA-N butane-1-sulfonyl chloride Chemical compound CCCCS(Cl)(=O)=O WEDIIKBPDQQQJU-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 210000001072 colon Anatomy 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- OCRJEDMRYXXVEI-UHFFFAOYSA-N ethyl 4-[4-[[2-hydroxy-3-[4-hydroxy-3-(methanesulfonamido)phenoxy]propyl]amino]piperidin-1-yl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N1CCC(NCC(O)COC=2C=C(NS(C)(=O)=O)C(O)=CC=2)CC1 OCRJEDMRYXXVEI-UHFFFAOYSA-N 0.000 description 2
- LVAVMJSXFSKLLZ-UHFFFAOYSA-N ethyl 4-[[4-[[2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]piperidin-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1CN1CCC(NCC(O)COC=2C=CC(O)=CC=2)CC1 LVAVMJSXFSKLLZ-UHFFFAOYSA-N 0.000 description 2
- UMPRJGKLMUDRHL-UHFFFAOYSA-N ethyl 4-fluorobenzoate Chemical compound CCOC(=O)C1=CC=C(F)C=C1 UMPRJGKLMUDRHL-UHFFFAOYSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
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- 238000007918 intramuscular administration Methods 0.000 description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- CZNGTXVOZOWWKM-UHFFFAOYSA-N methyl 4-bromobenzoate Chemical compound COC(=O)C1=CC=C(Br)C=C1 CZNGTXVOZOWWKM-UHFFFAOYSA-N 0.000 description 2
- KUVWNDAUQMBWDS-UHFFFAOYSA-N n-[6-[4-[[2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]piperidin-1-yl]pyridin-3-yl]-4-propan-2-ylbenzenesulfonamide Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)NC1=CC=C(N2CCC(CC2)NCC(O)COC=2C=CC(O)=CC=2)N=C1 KUVWNDAUQMBWDS-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
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- 208000024891 symptom Diseases 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- LCSSICHULCDHJO-OAQYLSRUSA-N tert-butyl n-butylsulfonyl-n-[5-[[(2s)-oxiran-2-yl]methoxy]-2-phenylmethoxyphenyl]carbamate Chemical compound C=1C=C(OCC=2C=CC=CC=2)C(N(C(=O)OC(C)(C)C)S(=O)(=O)CCCC)=CC=1OC[C@@H]1CO1 LCSSICHULCDHJO-OAQYLSRUSA-N 0.000 description 2
- CKXZPVPIDOJLLM-UHFFFAOYSA-N tert-butyl n-piperidin-4-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCNCC1 CKXZPVPIDOJLLM-UHFFFAOYSA-N 0.000 description 2
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
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- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- KPBSJEBFALFJTO-UHFFFAOYSA-N propane-1-sulfonyl chloride Chemical compound CCCS(Cl)(=O)=O KPBSJEBFALFJTO-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000037390 scarring Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000006203 subcutaneous dosage form Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- PPBDBQUUDSPMOU-UHFFFAOYSA-N tert-butyl 1-(5-nitropyridin-2-yl)piperidine-4-carboxylate Chemical compound C1CC(C(=O)OC(C)(C)C)CCN1C1=CC=C([N+]([O-])=O)C=N1 PPBDBQUUDSPMOU-UHFFFAOYSA-N 0.000 description 1
- VXCHBMUMUYBTJW-UHFFFAOYSA-N tert-butyl 2-[4-(2,5-dimethylpyrrol-1-yl)piperidin-1-yl]benzoate Chemical compound CC1=CC=C(C)N1C1CCN(C=2C(=CC=CC=2)C(=O)OC(C)(C)C)CC1 VXCHBMUMUYBTJW-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WFKLUNLIZMWKNF-UHFFFAOYSA-N tert-butyl n-(1-benzylpiperidin-4-yl)carbamate Chemical compound C1CC(NC(=O)OC(C)(C)C)CCN1CC1=CC=CC=C1 WFKLUNLIZMWKNF-UHFFFAOYSA-N 0.000 description 1
- VHYXAWLOJGIJPC-UHFFFAOYSA-N tert-butyl n-(piperidin-4-ylmethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC1CCNCC1 VHYXAWLOJGIJPC-UHFFFAOYSA-N 0.000 description 1
- UPITUMSSPJTJPS-UHFFFAOYSA-N tert-butyl n-[1-(4-carbamoylphenyl)piperidin-4-yl]carbamate Chemical compound C1CC(NC(=O)OC(C)(C)C)CCN1C1=CC=C(C(N)=O)C=C1 UPITUMSSPJTJPS-UHFFFAOYSA-N 0.000 description 1
- QQKMRJBIMLSKQL-UHFFFAOYSA-N tert-butyl n-[1-(4-cyanophenyl)piperidin-4-yl]carbamate Chemical compound C1CC(NC(=O)OC(C)(C)C)CCN1C1=CC=C(C#N)C=C1 QQKMRJBIMLSKQL-UHFFFAOYSA-N 0.000 description 1
- PEPDLOXDPHPNSA-UHFFFAOYSA-N tert-butyl n-[1-(5-aminopyridin-2-yl)piperidin-4-yl]carbamate Chemical compound C1CC(NC(=O)OC(C)(C)C)CCN1C1=CC=C(N)C=N1 PEPDLOXDPHPNSA-UHFFFAOYSA-N 0.000 description 1
- VJTYCADUMVARGX-UHFFFAOYSA-N tert-butyl n-[1-[4-(butylcarbamoyl)phenyl]piperidin-4-yl]carbamate Chemical compound C1=CC(C(=O)NCCCC)=CC=C1N1CCC(NC(=O)OC(C)(C)C)CC1 VJTYCADUMVARGX-UHFFFAOYSA-N 0.000 description 1
- QVUQBORTADDFFO-UHFFFAOYSA-N tert-butyl n-[1-[4-(diethylcarbamoyl)phenyl]piperidin-4-yl]carbamate Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N1CCC(NC(=O)OC(C)(C)C)CC1 QVUQBORTADDFFO-UHFFFAOYSA-N 0.000 description 1
- RUBDVSZTHDLBFG-UHFFFAOYSA-N tert-butyl n-[1-[5-[(4-bromophenyl)sulfonylamino]pyridin-2-yl]piperidin-4-yl]carbamate Chemical compound C1CC(NC(=O)OC(C)(C)C)CCN1C(N=C1)=CC=C1NS(=O)(=O)C1=CC=C(Br)C=C1 RUBDVSZTHDLBFG-UHFFFAOYSA-N 0.000 description 1
- IXBJXNLJTWIGOU-UHFFFAOYSA-N tert-butyl n-[1-[5-[(4-propan-2-ylphenyl)sulfonylamino]pyridin-2-yl]piperidin-4-yl]carbamate Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)NC1=CC=C(N2CCC(CC2)NC(=O)OC(C)(C)C)N=C1 IXBJXNLJTWIGOU-UHFFFAOYSA-N 0.000 description 1
- GGMXZPHICXPQNP-UHFFFAOYSA-N tert-butyl n-butylsulfonyl-n-(5-hydroxy-2-phenylmethoxyphenyl)carbamate Chemical compound CCCCS(=O)(=O)N(C(=O)OC(C)(C)C)C1=CC(O)=CC=C1OCC1=CC=CC=C1 GGMXZPHICXPQNP-UHFFFAOYSA-N 0.000 description 1
- VMKJKEINOOXOCH-UHFFFAOYSA-N tert-butyl n-methylsulfonyl-n-[5-(oxiran-2-ylmethoxy)-2-phenylmethoxyphenyl]carbamate Chemical compound C=1C=C(OCC=2C=CC=CC=2)C(N(C(=O)OC(C)(C)C)S(C)(=O)=O)=CC=1OCC1CO1 VMKJKEINOOXOCH-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/06—Antiabortive agents; Labour repressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Ophthalmology & Optometry (AREA)
- Endocrinology (AREA)
- Gynecology & Obstetrics (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Pregnancy & Childbirth (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9915932A FR2802529B1 (fr) | 1999-12-17 | 1999-12-17 | Phenoxypropanolamines, procede pour les preparer et compositions pharmaceutiques les contenant |
| FR99/15932 | 1999-12-17 | ||
| FR99/15931 | 1999-12-17 | ||
| FR9915931A FR2802531B1 (fr) | 1999-12-17 | 1999-12-17 | Phenoxypropanolamines, procede pour leur preparation et compositions pharmaceutiques les contenant |
| PCT/FR2000/003535 WO2001043744A1 (fr) | 1999-12-17 | 2000-12-14 | Phenoxypropanolamines, procede pour leur preparation et compositions pharmaceutiques les contenant |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003517013A JP2003517013A (ja) | 2003-05-20 |
| JP2003517013A5 JP2003517013A5 (enExample) | 2008-02-14 |
| JP4782342B2 true JP4782342B2 (ja) | 2011-09-28 |
Family
ID=26235183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001544882A Expired - Fee Related JP4782342B2 (ja) | 1999-12-17 | 2000-12-14 | フェノキシプロパノールアミン類、それらの製造方法およびそれらを含む医薬組成物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6867220B2 (enExample) |
| EP (1) | EP1242083B1 (enExample) |
| JP (1) | JP4782342B2 (enExample) |
| AT (1) | ATE356624T1 (enExample) |
| AU (1) | AU2525801A (enExample) |
| DE (1) | DE60033964T2 (enExample) |
| WO (1) | WO2001043744A1 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9902987D0 (sv) | 1999-08-24 | 1999-08-24 | Astra Pharma Prod | Novel compounds |
| CO5300399A1 (es) | 2000-02-25 | 2003-07-31 | Astrazeneca Ab | Heterocicliocs que contienen nitrogeno, proceso para su preparacion y composiciones farmaceuticas que los contienen |
| US7074934B2 (en) * | 2000-06-13 | 2006-07-11 | Tularik Limited | Serine protease inhibitors |
| AR028948A1 (es) | 2000-06-20 | 2003-05-28 | Astrazeneca Ab | Compuestos novedosos |
| US7005439B2 (en) | 2000-06-20 | 2006-02-28 | Astrazeneca Ab | Compounds |
| US6537994B2 (en) | 2000-07-17 | 2003-03-25 | Wyeth | Heterocyclic β3 adrenergic receptor agonists |
| US6444685B1 (en) * | 2000-07-17 | 2002-09-03 | Wyeth | N-(4-sulfonylaryl)Cyclylamine 2-hydroxyethylamines as beta-3 adrenergic receptor agonists |
| US6465501B2 (en) | 2000-07-17 | 2002-10-15 | Wyeth | Azolidines as β3 adrenergic receptor agonists |
| US6525202B2 (en) | 2000-07-17 | 2003-02-25 | Wyeth | Cyclic amine phenyl beta-3 adrenergic receptor agonists |
| US6498170B2 (en) | 2000-07-17 | 2002-12-24 | Wyeth | Cyclamine sulfonamides as β-3 adrenergic receptor agonists |
| US6410734B1 (en) | 2000-07-17 | 2002-06-25 | Wyeth | 2-substituted thiazolidinones as beta-3 adrenergic receptor agonists |
| US6506901B2 (en) | 2000-07-17 | 2003-01-14 | Wyeth | Substituted 2-(S)-hydroxy-3-(piperidin-4-yl-methylamino)-propyl ethers and substituted 2-aryl-2-(R)-hydroxy-1-(piperidin-4-yl-methyl)-ethylamine β-3 adrenergic receptor agonists |
| GB0104050D0 (en) | 2001-02-19 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
| AR035230A1 (es) | 2001-03-19 | 2004-05-05 | Astrazeneca Ab | Compuestos de bencimidazol, proceso para su preparacion, composicion farmaceutica, proceso para la preparacion de dicha composicion farmaceutica, y usos de estos compuestos para la elaboracion de medicamentos |
| GB0107228D0 (en) | 2001-03-22 | 2001-05-16 | Astrazeneca Ab | Chemical compounds |
| SE0101038D0 (sv) * | 2001-03-23 | 2001-03-23 | Astrazeneca Ab | Novel compounds |
| SE0103818D0 (sv) | 2001-11-15 | 2001-11-15 | Astrazeneca Ab | Chemical compounds |
| SE0301369D0 (sv) | 2003-05-09 | 2003-05-09 | Astrazeneca Ab | Chemical compounds |
| TW200738634A (en) | 2005-08-02 | 2007-10-16 | Astrazeneca Ab | New salt |
| EP1947103A1 (en) * | 2007-01-22 | 2008-07-23 | 4Sc Ag | Aryloxypropanolamines, methods of preparation thereof and use of aryloxypropanolamines as medicaments |
| MA44037B1 (fr) | 2016-06-06 | 2020-03-31 | Arena Pharm Inc | Modulateurs du récepteur adrénergique bêta 3 utile dans le traitement ou la prévention de troubles associés à ceux-ci |
| ES2788856T3 (es) | 2017-03-20 | 2020-10-23 | Forma Therapeutics Inc | Composiciones de pirrolopirrol como activadores de quinasa de piruvato (PKR) |
| TWI822713B (zh) * | 2017-12-06 | 2023-11-21 | 美商艾尼納製藥公司 | 適用於治療或預防與其相關之病症之β－３腎上腺素受體的調節劑 |
| ES2989438T3 (es) | 2018-09-19 | 2024-11-26 | Novo Nordisk Healthcare Ag | Activación de la piruvato cinasa R |
| WO2020061378A1 (en) | 2018-09-19 | 2020-03-26 | Forma Therapeutics, Inc. | Treating sickle cell disease with a pyruvate kinase r activating compound |
| MA57202B1 (fr) | 2019-09-19 | 2025-09-30 | Novo Nordisk Health Care Ag | Compositions d'activation de la pyruvate kinase r (pkr) |
| US12128035B2 (en) | 2021-03-19 | 2024-10-29 | Novo Nordisk Health Care Ag | Activating pyruvate kinase R |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58206581A (ja) * | 1982-05-13 | 1983-12-01 | ゲロト−フアルマツオイチカ・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | ピロガロ−ルの新規な環置換誘導体 |
| WO1999052872A1 (en) * | 1998-04-09 | 1999-10-21 | Meiji Seika Kaisha, Ltd. | AMINOPIPERIDINE DERIVATIVES AS INTEGRIN αvβ3 ANTAGONISTS |
| JP2004504299A (ja) * | 2000-07-17 | 2004-02-12 | ワイス | 環状アミンフェニルベータ−３アドレナリン作用性受容体アゴニスト |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2163150B (en) * | 1984-07-19 | 1988-05-25 | Sandoz Ltd | 3-aminopropoxyaryl derivatives |
| DE3524955A1 (de) * | 1984-07-19 | 1986-01-30 | Sandoz-Patent-GmbH, 7850 Lörrach | 3-aminopropoxyaryl-derivate, ihre herstellung und sie enthaltende arzneimittel |
| US5627196A (en) * | 1995-01-17 | 1997-05-06 | Eli Lilly And Company | Compounds having effects on serotonin-related systems |
| PE92198A1 (es) * | 1996-08-01 | 1999-01-09 | Banyu Pharma Co Ltd | Derivados de 1,4-piperidina disustituida que contienen fluor |
| FR2780057B1 (fr) | 1998-06-18 | 2002-09-13 | Sanofi Sa | Phenoxypropanolamines, procede pour leur preparation et compositions pharmaceutiques les contenant |
| US6444685B1 (en) * | 2000-07-17 | 2002-09-03 | Wyeth | N-(4-sulfonylaryl)Cyclylamine 2-hydroxyethylamines as beta-3 adrenergic receptor agonists |
-
2000
- 2000-12-14 AU AU25258/01A patent/AU2525801A/en not_active Abandoned
- 2000-12-14 US US10/149,497 patent/US6867220B2/en not_active Expired - Fee Related
- 2000-12-14 AT AT00988915T patent/ATE356624T1/de not_active IP Right Cessation
- 2000-12-14 DE DE60033964T patent/DE60033964T2/de not_active Expired - Lifetime
- 2000-12-14 JP JP2001544882A patent/JP4782342B2/ja not_active Expired - Fee Related
- 2000-12-14 EP EP00988915A patent/EP1242083B1/fr not_active Expired - Lifetime
- 2000-12-14 WO PCT/FR2000/003535 patent/WO2001043744A1/fr not_active Ceased
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58206581A (ja) * | 1982-05-13 | 1983-12-01 | ゲロト−フアルマツオイチカ・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | ピロガロ−ルの新規な環置換誘導体 |
| WO1999052872A1 (en) * | 1998-04-09 | 1999-10-21 | Meiji Seika Kaisha, Ltd. | AMINOPIPERIDINE DERIVATIVES AS INTEGRIN αvβ3 ANTAGONISTS |
| JP2004504299A (ja) * | 2000-07-17 | 2004-02-12 | ワイス | 環状アミンフェニルベータ−３アドレナリン作用性受容体アゴニスト |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1242083A1 (fr) | 2002-09-25 |
| DE60033964D1 (de) | 2007-04-26 |
| US20030040530A1 (en) | 2003-02-27 |
| ATE356624T1 (de) | 2007-04-15 |
| US6867220B2 (en) | 2005-03-15 |
| EP1242083B1 (fr) | 2007-03-14 |
| DE60033964T2 (de) | 2007-11-29 |
| WO2001043744A1 (fr) | 2001-06-21 |
| JP2003517013A (ja) | 2003-05-20 |
| AU2525801A (en) | 2001-06-25 |
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