SK17932002A3 - Deriváty fenylu, spôsob ich prípravy, farmaceutické kompozície, ktoré ich obsahujú a ich použitie v terapii - Google Patents
Deriváty fenylu, spôsob ich prípravy, farmaceutické kompozície, ktoré ich obsahujú a ich použitie v terapii Download PDFInfo
- Publication number
- SK17932002A3 SK17932002A3 SK1793-2002A SK17932002A SK17932002A3 SK 17932002 A3 SK17932002 A3 SK 17932002A3 SK 17932002 A SK17932002 A SK 17932002A SK 17932002 A3 SK17932002 A3 SK 17932002A3
- Authority
- SK
- Slovakia
- Prior art keywords
- phenyl
- amino
- piperidinyl
- acetamide
- hydroxypropoxy
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 27
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 11
- 230000008569 process Effects 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 36
- 230000001225 therapeutic effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 78
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 8
- -1 nitro, carboxyl Chemical group 0.000 claims description 93
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 26
- 239000012453 solvate Substances 0.000 claims description 24
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 21
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 20
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 20
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 20
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 229920006395 saturated elastomer Polymers 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 8
- XQGVQRPSTODODM-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrrole-2-carboxylic acid Chemical compound CC1=CC(C)=C(C(O)=O)N1 XQGVQRPSTODODM-UHFFFAOYSA-N 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 5
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 239000001301 oxygen Chemical group 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 3
- JYNYZGTZSYGZFF-UHFFFAOYSA-N 2-[3-[[1-[(4-bromophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1OCC(O)CNC1CCN(CC=2C=CC(Br)=CC=2)CC1 JYNYZGTZSYGZFF-UHFFFAOYSA-N 0.000 claims description 3
- ZWHVZEVXTBVHKA-UHFFFAOYSA-N 2-[3-[[1-[(4-fluorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1OCC(O)CNC1CCN(CC=2C=CC(F)=CC=2)CC1 ZWHVZEVXTBVHKA-UHFFFAOYSA-N 0.000 claims description 3
- 102000009410 Chemokine receptor Human genes 0.000 claims description 3
- 108050000299 Chemokine receptor Proteins 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- UHWWMQGKINJTML-XMMPIXPASA-N n-[2-[(2r)-3-[[1-[(4-chlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxy-2-methylpropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OC[C@](C)(O)CNC1CCN(CC=2C=CC(Cl)=CC=2)CC1 UHWWMQGKINJTML-XMMPIXPASA-N 0.000 claims description 3
- UHWWMQGKINJTML-DEOSSOPVSA-N n-[2-[(2s)-3-[[1-[(4-chlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxy-2-methylpropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OC[C@@](C)(O)CNC1CCN(CC=2C=CC(Cl)=CC=2)CC1 UHWWMQGKINJTML-DEOSSOPVSA-N 0.000 claims description 3
- XZZZCTNRNINFIV-NRFANRHFSA-N n-[2-[(2s)-3-[[1-[(4-chlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OC[C@@H](O)CNC1CCN(CC=2C=CC(Cl)=CC=2)CC1 XZZZCTNRNINFIV-NRFANRHFSA-N 0.000 claims description 3
- JREWIIXZKFBBRF-NRFANRHFSA-N n-[2-[(2s)-3-[[1-[(4-fluorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OC[C@@H](O)CNC1CCN(CC=2C=CC(F)=CC=2)CC1 JREWIIXZKFBBRF-NRFANRHFSA-N 0.000 claims description 3
- OVJRIIXZEYSYCL-UHFFFAOYSA-N n-[2-[3-[[1-[(3,4-dichlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxy-2-methylpropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OCC(C)(O)CNC1CCN(CC=2C=C(Cl)C(Cl)=CC=2)CC1 OVJRIIXZEYSYCL-UHFFFAOYSA-N 0.000 claims description 3
- BKFHDKZKXZTNQR-UHFFFAOYSA-N n-[2-[3-[[1-[(3,4-dichlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]-5-phenylphenyl]acetamide Chemical compound CC(=O)NC1=CC(C=2C=CC=CC=2)=CC=C1OCC(O)CNC(CC1)CCN1CC1=CC=C(Cl)C(Cl)=C1 BKFHDKZKXZTNQR-UHFFFAOYSA-N 0.000 claims description 3
- DQKWBTYEFDDBCD-UHFFFAOYSA-N n-[2-[3-[[1-[(3,4-dichlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]phenyl]benzamide Chemical compound C=1C=CC=C(NC(=O)C=2C=CC=CC=2)C=1OCC(O)CNC(CC1)CCN1CC1=CC=C(Cl)C(Cl)=C1 DQKWBTYEFDDBCD-UHFFFAOYSA-N 0.000 claims description 3
- MBQWSRZWBXESPI-UHFFFAOYSA-N n-[2-[3-[[1-[(3,4-difluorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxy-2-methylpropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OCC(C)(O)CNC1CCN(CC=2C=C(F)C(F)=CC=2)CC1 MBQWSRZWBXESPI-UHFFFAOYSA-N 0.000 claims description 3
- XVXUQBGLPUEGPD-UHFFFAOYSA-N n-[2-[3-[[1-[(3,4-difluorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OCC(O)CNC1CCN(CC=2C=C(F)C(F)=CC=2)CC1 XVXUQBGLPUEGPD-UHFFFAOYSA-N 0.000 claims description 3
- MNBLPGMJPDFOBA-UHFFFAOYSA-N n-[2-[3-[[1-[(3,4-difluorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]phenyl]benzamide Chemical compound C=1C=CC=C(NC(=O)C=2C=CC=CC=2)C=1OCC(O)CNC(CC1)CCN1CC1=CC=C(F)C(F)=C1 MNBLPGMJPDFOBA-UHFFFAOYSA-N 0.000 claims description 3
- NACXBKZWHYBDEL-UHFFFAOYSA-N n-[2-[3-[[1-[(3-chloro-4-fluorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxy-2-methylpropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OCC(C)(O)CNC1CCN(CC=2C=C(Cl)C(F)=CC=2)CC1 NACXBKZWHYBDEL-UHFFFAOYSA-N 0.000 claims description 3
- ROYXRRXTBDPMIB-UHFFFAOYSA-N n-[2-[3-[[1-[(3-chloro-4-fluorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OCC(O)CNC1CCN(CC=2C=C(Cl)C(F)=CC=2)CC1 ROYXRRXTBDPMIB-UHFFFAOYSA-N 0.000 claims description 3
- ZHFGLTBMIUEXKD-UHFFFAOYSA-N n-[2-[3-[[1-[(3-chloro-4-fluorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]phenyl]benzamide Chemical compound C=1C=CC=C(NC(=O)C=2C=CC=CC=2)C=1OCC(O)CNC(CC1)CCN1CC1=CC=C(F)C(Cl)=C1 ZHFGLTBMIUEXKD-UHFFFAOYSA-N 0.000 claims description 3
- LYQPXPOTVRGEDB-UHFFFAOYSA-N n-[2-[3-[[1-[(4-bromophenyl)methyl]piperidin-4-yl]amino]-2-hydroxy-2-methylpropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OCC(C)(O)CNC1CCN(CC=2C=CC(Br)=CC=2)CC1 LYQPXPOTVRGEDB-UHFFFAOYSA-N 0.000 claims description 3
- CYSCAVXFUNWUFH-UHFFFAOYSA-N n-[2-[3-[[1-[(4-bromophenyl)methyl]piperidin-4-yl]amino]-2-hydroxy-2-methylpropoxy]phenyl]benzamide Chemical compound C=1C=CC=C(NC(=O)C=2C=CC=CC=2)C=1OCC(O)(C)CNC(CC1)CCN1CC1=CC=C(Br)C=C1 CYSCAVXFUNWUFH-UHFFFAOYSA-N 0.000 claims description 3
- NCRZBMXHPCBDHQ-UHFFFAOYSA-N n-[2-[3-[[1-[(4-bromophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OCC(O)CNC1CCN(CC=2C=CC(Br)=CC=2)CC1 NCRZBMXHPCBDHQ-UHFFFAOYSA-N 0.000 claims description 3
- WNSWPHLREVGNSE-UHFFFAOYSA-N n-[2-[3-[[1-[(4-bromophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]phenyl]benzamide Chemical compound C=1C=CC=C(NC(=O)C=2C=CC=CC=2)C=1OCC(O)CNC(CC1)CCN1CC1=CC=C(Br)C=C1 WNSWPHLREVGNSE-UHFFFAOYSA-N 0.000 claims description 3
- UHWWMQGKINJTML-UHFFFAOYSA-N n-[2-[3-[[1-[(4-chlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxy-2-methylpropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OCC(C)(O)CNC1CCN(CC=2C=CC(Cl)=CC=2)CC1 UHWWMQGKINJTML-UHFFFAOYSA-N 0.000 claims description 3
- VKAWDNYVQDHWLT-UHFFFAOYSA-N n-[2-[3-[[1-[(4-chlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxy-2-methylpropoxy]phenyl]benzamide Chemical compound C=1C=CC=C(NC(=O)C=2C=CC=CC=2)C=1OCC(O)(C)CNC(CC1)CCN1CC1=CC=C(Cl)C=C1 VKAWDNYVQDHWLT-UHFFFAOYSA-N 0.000 claims description 3
- HCRCJAUNDNWDKN-UHFFFAOYSA-N n-[2-[3-[[1-[(4-chlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]-4-methylphenyl]acetamide Chemical compound CC(=O)NC1=CC=C(C)C=C1OCC(O)CNC1CCN(CC=2C=CC(Cl)=CC=2)CC1 HCRCJAUNDNWDKN-UHFFFAOYSA-N 0.000 claims description 3
- XZZZCTNRNINFIV-UHFFFAOYSA-N n-[2-[3-[[1-[(4-chlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OCC(O)CNC1CCN(CC=2C=CC(Cl)=CC=2)CC1 XZZZCTNRNINFIV-UHFFFAOYSA-N 0.000 claims description 3
- OTSQSUHXXKRRPY-UHFFFAOYSA-N n-[2-[3-[[1-[(4-chlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]phenyl]benzamide Chemical compound C=1C=CC=C(NC(=O)C=2C=CC=CC=2)C=1OCC(O)CNC(CC1)CCN1CC1=CC=C(Cl)C=C1 OTSQSUHXXKRRPY-UHFFFAOYSA-N 0.000 claims description 3
- JHINGSHMHAREOG-UHFFFAOYSA-N n-[2-[3-[[1-[(4-fluorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxy-2-methylpropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OCC(C)(O)CNC1CCN(CC=2C=CC(F)=CC=2)CC1 JHINGSHMHAREOG-UHFFFAOYSA-N 0.000 claims description 3
- AKFLRPNJJJZUED-UHFFFAOYSA-N n-[2-[3-[[1-[(4-fluorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxy-2-methylpropoxy]phenyl]benzamide Chemical compound C=1C=CC=C(NC(=O)C=2C=CC=CC=2)C=1OCC(O)(C)CNC(CC1)CCN1CC1=CC=C(F)C=C1 AKFLRPNJJJZUED-UHFFFAOYSA-N 0.000 claims description 3
- JREWIIXZKFBBRF-UHFFFAOYSA-N n-[2-[3-[[1-[(4-fluorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OCC(O)CNC1CCN(CC=2C=CC(F)=CC=2)CC1 JREWIIXZKFBBRF-UHFFFAOYSA-N 0.000 claims description 3
- NFNDJLUWWMATSI-UHFFFAOYSA-N n-[2-[3-[[1-[(4-fluorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]phenyl]benzamide Chemical compound C=1C=CC=C(NC(=O)C=2C=CC=CC=2)C=1OCC(O)CNC(CC1)CCN1CC1=CC=C(F)C=C1 NFNDJLUWWMATSI-UHFFFAOYSA-N 0.000 claims description 3
- DGJICJJZEZPZAM-UHFFFAOYSA-N n-[2-fluoro-6-[3-[[1-[(4-fluorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=C(F)C=CC=C1OCC(O)CNC1CCN(CC=2C=CC(F)=CC=2)CC1 DGJICJJZEZPZAM-UHFFFAOYSA-N 0.000 claims description 3
- XBGPOFSOBGESNM-NRFANRHFSA-N n-[4-fluoro-2-[(2s)-3-[[1-[(4-fluorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(F)C=C1OC[C@@H](O)CNC1CCN(CC=2C=CC(F)=CC=2)CC1 XBGPOFSOBGESNM-NRFANRHFSA-N 0.000 claims description 3
- YILMPRHXSAYTAZ-UHFFFAOYSA-N n-[4-fluoro-2-[3-[[1-[(4-fluorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxy-2-methylpropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(F)C=C1OCC(C)(O)CNC1CCN(CC=2C=CC(F)=CC=2)CC1 YILMPRHXSAYTAZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 3
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 208000027866 inflammatory disease Diseases 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- FBMVIPOJAIEMEQ-UHFFFAOYSA-N n-[2-[3-[[1-[(3,4-dichlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]-4-fluorophenyl]acetamide Chemical compound CC(=O)NC1=CC=C(F)C=C1OCC(O)CNC1CCN(CC=2C=C(Cl)C(Cl)=CC=2)CC1 FBMVIPOJAIEMEQ-UHFFFAOYSA-N 0.000 claims description 2
- SFSYBIMGDOACAY-UHFFFAOYSA-N n-[2-[3-[[1-[(3,4-dichlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]-5-fluorophenyl]acetamide Chemical compound CC(=O)NC1=CC(F)=CC=C1OCC(O)CNC1CCN(CC=2C=C(Cl)C(Cl)=CC=2)CC1 SFSYBIMGDOACAY-UHFFFAOYSA-N 0.000 claims description 2
- VCFZUDKMHJJFCH-UHFFFAOYSA-N n-[2-[3-[[1-[(3,4-dichlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]-5-methylphenyl]acetamide Chemical compound CC(=O)NC1=CC(C)=CC=C1OCC(O)CNC1CCN(CC=2C=C(Cl)C(Cl)=CC=2)CC1 VCFZUDKMHJJFCH-UHFFFAOYSA-N 0.000 claims description 2
- JNJDANVEPOEXLR-UHFFFAOYSA-N n-[2-[3-[[1-[(3-chlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]phenyl]-3,5-dimethyl-1h-pyrrole-2-carboxamide Chemical compound N1C(C)=CC(C)=C1C(=O)NC1=CC=CC=C1OCC(O)CNC1CCN(CC=2C=C(Cl)C=CC=2)CC1 JNJDANVEPOEXLR-UHFFFAOYSA-N 0.000 claims description 2
- XXJAJULFILCYBG-UHFFFAOYSA-N n-[2-[3-[[1-[(3-fluorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]phenyl]-3,5-dimethyl-1h-pyrrole-2-carboxamide Chemical compound N1C(C)=CC(C)=C1C(=O)NC1=CC=CC=C1OCC(O)CNC1CCN(CC=2C=C(F)C=CC=2)CC1 XXJAJULFILCYBG-UHFFFAOYSA-N 0.000 claims description 2
- BHXJPNWBNCPZGU-UHFFFAOYSA-N n-[2-[3-[[1-[(4-chlorophenyl)methyl]piperidin-4-yl]amino]-3-hydroxypropoxy]phenyl]-2-methylpropanamide Chemical compound CC(C)C(=O)NC1=CC=CC=C1OCCC(O)NC1CCN(CC=2C=CC(Cl)=CC=2)CC1 BHXJPNWBNCPZGU-UHFFFAOYSA-N 0.000 claims description 2
- PBHKFCDHJNSZTE-UHFFFAOYSA-N n-[5-chloro-2-[3-[[1-[(4-chlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1OCC(O)CNC1CCN(CC=2C=CC(Cl)=CC=2)CC1 PBHKFCDHJNSZTE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 208000023504 respiratory system disease Diseases 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 claims 1
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- ZUMJGKIHNJRMPZ-UHFFFAOYSA-N n-[5-cyano-2-[3-[[1-[(3,4-dichlorophenyl)methyl]piperidin-4-yl]amino]-2-hydroxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC(C#N)=CC=C1OCC(O)CNC1CCN(CC=2C=C(Cl)C(Cl)=CC=2)CC1 ZUMJGKIHNJRMPZ-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 208000002574 reactive arthritis Diseases 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 201000000306 sarcoidosis Diseases 0.000 description 1
- 230000001932 seasonal effect Effects 0.000 description 1
- 208000008742 seborrheic dermatitis Diseases 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 201000005671 spondyloarthropathy Diseases 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- JHYOUOHNCPGQOS-UHFFFAOYSA-N tert-butyl 3-hydroxypiperidine-1-carboxylate;3-(4-chlorophenoxy)piperidine Chemical compound CC(C)(C)OC(=O)N1CCCC(O)C1.C1=CC(Cl)=CC=C1OC1CNCCC1 JHYOUOHNCPGQOS-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 206010043554 thrombocytopenia Diseases 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 208000001319 vasomotor rhinitis Diseases 0.000 description 1
Classifications
-
- 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
-
- 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
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0002331A SE0002331D0 (sv) | 2000-06-20 | 2000-06-20 | Novel compounds |
| SE0004480A SE0004480D0 (sv) | 2000-12-05 | 2000-12-05 | Novel compounds |
| PCT/SE2001/001377 WO2001098273A1 (en) | 2000-06-20 | 2001-06-14 | Novel compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK17932002A3 true SK17932002A3 (sk) | 2003-09-11 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1793-2002A SK17932002A3 (sk) | 2000-06-20 | 2001-06-14 | Deriváty fenylu, spôsob ich prípravy, farmaceutické kompozície, ktoré ich obsahujú a ich použitie v terapii |
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| JP (1) | JP4022142B2 (OSRAM) |
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| CN (1) | CN1307157C (OSRAM) |
| AR (1) | AR028948A1 (OSRAM) |
| AU (2) | AU2001274763B2 (OSRAM) |
| BR (1) | BR0111667A (OSRAM) |
| CA (1) | CA2414095C (OSRAM) |
| CZ (1) | CZ20024146A3 (OSRAM) |
| EE (1) | EE05157B1 (OSRAM) |
| HU (1) | HUP0301187A3 (OSRAM) |
| IL (2) | IL153167A0 (OSRAM) |
| IS (1) | IS6658A (OSRAM) |
| MX (1) | MXPA02012425A (OSRAM) |
| MY (1) | MY136520A (OSRAM) |
| NO (1) | NO324698B1 (OSRAM) |
| NZ (1) | NZ523047A (OSRAM) |
| PL (1) | PL203936B1 (OSRAM) |
| RU (2) | RU2298550C2 (OSRAM) |
| SK (1) | SK17932002A3 (OSRAM) |
| WO (1) | WO2001098273A1 (OSRAM) |
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| AR028948A1 (es) * | 2000-06-20 | 2003-05-28 | Astrazeneca Ab | Compuestos novedosos |
| US7005439B2 (en) * | 2000-06-20 | 2006-02-28 | Astrazeneca Ab | 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 |
| SE0202133D0 (sv) | 2002-07-08 | 2002-07-08 | Astrazeneca Ab | Novel compounds |
| JP4368375B2 (ja) * | 2003-02-17 | 2009-11-18 | エフ．ホフマン−ラ ロシュ アーゲー | ピペリジン−ベンゼンスルホンアミド誘導体 |
| US7723509B2 (en) | 2003-04-17 | 2010-05-25 | Alnylam Pharmaceuticals | IRNA agents with biocleavable tethers |
| US8017762B2 (en) | 2003-04-17 | 2011-09-13 | Alnylam Pharmaceuticals, Inc. | Modified iRNA agents |
| US7851615B2 (en) | 2003-04-17 | 2010-12-14 | Alnylam Pharmaceuticals, Inc. | Lipophilic conjugated iRNA agents |
| US8796436B2 (en) | 2003-04-17 | 2014-08-05 | Alnylam Pharmaceuticals, Inc. | Modified iRNA agents |
| CA2522637C (en) | 2003-04-17 | 2014-01-21 | Alnylam Pharmaceuticals, Inc. | Modified irna agents |
| WO2005023771A1 (ja) * | 2003-09-05 | 2005-03-17 | Ono Pharmaceutical Co., Ltd. | ケモカインレセプターアンタゴニストおよびその医薬用途 |
| SE0303090D0 (sv) | 2003-11-20 | 2003-11-20 | Astrazeneca Ab | Novel compounds |
| SE0303541D0 (sv) | 2003-12-22 | 2003-12-22 | Astrazeneca Ab | New compounds |
| CA2617127A1 (en) * | 2005-08-01 | 2007-02-08 | Astrazeneca Ab | Novel piperidine derivatives as chemokine receptor modulators useful for the treatment of respiratory diseases. |
| TW200738635A (en) * | 2005-08-02 | 2007-10-16 | Astrazeneca Ab | New salt |
| TW200734305A (en) * | 2005-08-02 | 2007-09-16 | Astrazeneca Ab | New salt III |
| TW200738634A (en) * | 2005-08-02 | 2007-10-16 | Astrazeneca Ab | New salt |
| TW200744612A (en) * | 2005-08-26 | 2007-12-16 | Astrazeneca Ab | New combination |
| JO2769B1 (en) | 2005-10-26 | 2014-03-15 | جانسين فارماسوتيكا ان. في | Rapid decomposition of physiologically antagonistic agents of the 2-dopamine receptor |
| TW200800895A (en) * | 2005-11-02 | 2008-01-01 | Astrazeneca Ab | Novel compounds |
| US20090023733A1 (en) * | 2006-03-07 | 2009-01-22 | Peter Cage | Piperidine Derivatives, Their Process for Preparation, Their Use as Therapeutic Agents and Pharmaceutical Compositions Containing Them |
| WO2007102768A1 (en) * | 2006-03-07 | 2007-09-13 | Astrazeneca Ab | Piperidine derivatives, their process for preparation, their use as therapeutic agents and pharmaceutical compositions containing them . |
| US20080064884A1 (en) * | 2006-05-10 | 2008-03-13 | Astrazeneca Ab | Novel Process 1 |
| JP2009544609A (ja) * | 2006-07-18 | 2009-12-17 | アストラゼネカ・アクチエボラーグ | 置換２−アセチルアミノ−アルコキシフェニルの製造方法 |
| JO2642B1 (en) | 2006-12-08 | 2012-06-17 | جانسين فارماسوتيكا ان. في | Dopamine 2 receptor antagonists are rapidly hydrolyzed |
| GB0702456D0 (en) | 2007-02-08 | 2007-03-21 | Astrazeneca Ab | New combination |
| JO2849B1 (en) | 2007-02-13 | 2015-03-15 | جانسين فارماسوتيكا ان. في | Dopamine 2 receptor antagonists are rapidly hydrolyzed |
| EP2125728A4 (en) * | 2007-02-23 | 2011-06-22 | Astrazeneca Ab | NOVEL COMBINATION OF COMPOUNDS FOR THE TREATMENT OF AIRWAY DISEASES, IN PARTICULAR CHRONIC OBSTRUCTIVE BRONCHOPNEUMOPATHY (COPD) AND ASTHMA |
| WO2008121065A1 (en) * | 2007-03-30 | 2008-10-09 | Astrazeneca Ab | Novel pyrrolidine derivatives as antagonists of the chemokine receptor |
| CA2682671C (en) | 2007-04-23 | 2015-11-17 | Janssen Pharmaceutica N.V. | Thia(dia)zoles as fast dissociating dopamine 2 receptor antagonists |
| PL2148873T3 (pl) | 2007-04-23 | 2013-01-31 | Janssen Pharmaceutica Nv | Pochodne 4-alkoksypirydazynowe jako szybko dysocjujący antagoniści receptora dopaminowego 2 |
| AU2009266001B2 (en) | 2008-07-03 | 2014-03-27 | Janssen Pharmaceutica Nv | Substituted 6- (1-piperazinyl) -pyridazines as 5-HT6 receptor antagonists |
| AU2009275887B2 (en) | 2008-07-31 | 2013-06-20 | Janssen Pharmaceutica Nv | Piperazin-1-yl-trifluoromethyl-substituted-pyridines as fast dissociating dopamine 2 receptor antagonists |
| GB0913345D0 (en) | 2009-07-31 | 2009-09-16 | Astrazeneca Ab | New combination 802 |
| WO2011061527A1 (en) | 2009-11-17 | 2011-05-26 | Astrazeneca Ab | Combinations comprising a glucocorticoid receptor modulator for the treatment of respiratory diseases |
| WO2011073662A1 (en) | 2009-12-17 | 2011-06-23 | Astrazeneca Ab | Combination of a benzoxazinone and a further agent for treating respiratory diseases |
| GB201021979D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | New compound |
| GB201021992D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | Compound |
| WO2012163848A1 (en) | 2011-05-27 | 2012-12-06 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment of crohn's disease |
| EP3083609B1 (en) | 2013-12-19 | 2018-08-15 | Merck Sharp & Dohme Corp. | Hiv protease inhibitors |
| US11958818B2 (en) | 2019-05-01 | 2024-04-16 | Boehringer Ingelheim International Gmbh | (R)-(2-methyloxiran-2-yl)methyl 4-bromobenzenesulfonate |
| EP4115885A1 (en) | 2021-07-05 | 2023-01-11 | Charité - Universitätsmedizin Berlin | A pharmaceutical composition comprising bay 86-5277 and salts thereof for use in the treatment of viral infections and hyperinflammation |
| TW202339719A (zh) | 2021-12-14 | 2023-10-16 | 德商百靈佳殷格翰國際股份有限公司 | 用於治療慢性腎臟病之醛固酮合成酶抑制劑 |
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- 2001-06-14 WO PCT/SE2001/001377 patent/WO2001098273A1/en not_active Ceased
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- 2001-06-14 CN CNB018142141A patent/CN1307157C/zh not_active Expired - Fee Related
- 2001-06-14 AU AU2001274763A patent/AU2001274763B2/en not_active Ceased
- 2001-06-14 EP EP01941406A patent/EP1299357A1/en not_active Withdrawn
- 2001-06-14 HU HU0301187A patent/HUP0301187A3/hu unknown
- 2001-06-14 AU AU7476301A patent/AU7476301A/xx active Pending
- 2001-06-14 SK SK1793-2002A patent/SK17932002A3/sk not_active Application Discontinuation
- 2001-06-14 IL IL15316701A patent/IL153167A0/xx unknown
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- 2001-06-14 CA CA002414095A patent/CA2414095C/en not_active Expired - Fee Related
- 2001-06-14 KR KR1020027017281A patent/KR100799061B1/ko not_active Expired - Fee Related
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- 2002-12-17 NO NO20026064A patent/NO324698B1/no not_active IP Right Cessation
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