ZA200305413B - Acylated indanyl amines and their use as pharmaceuticals. - Google Patents
Acylated indanyl amines and their use as pharmaceuticals. Download PDFInfo
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- ZA200305413B ZA200305413B ZA200305413A ZA200305413A ZA200305413B ZA 200305413 B ZA200305413 B ZA 200305413B ZA 200305413 A ZA200305413 A ZA 200305413A ZA 200305413 A ZA200305413 A ZA 200305413A ZA 200305413 B ZA200305413 B ZA 200305413B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- phenyl
- group
- methyl
- heteroaryl
- Prior art date
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- -1 Acylated indanyl amines Chemical class 0.000 title claims description 459
- 239000003814 drug Substances 0.000 title claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 174
- 229910052736 halogen Inorganic materials 0.000 claims description 118
- 150000002367 halogens Chemical class 0.000 claims description 116
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 113
- 125000001072 heteroaryl group Chemical group 0.000 claims description 103
- 229910052799 carbon Inorganic materials 0.000 claims description 81
- 125000002577 pseudohalo group Chemical group 0.000 claims description 80
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 78
- 125000003118 aryl group Chemical group 0.000 claims description 53
- 125000000623 heterocyclic group Chemical group 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 45
- 229910052757 nitrogen Inorganic materials 0.000 claims description 37
- 125000005842 heteroatom Chemical group 0.000 claims description 35
- 229910052731 fluorine Inorganic materials 0.000 claims description 33
- 229910052760 oxygen Inorganic materials 0.000 claims description 31
- 229910052717 sulfur Inorganic materials 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 21
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 20
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 19
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical class C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 claims description 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 125000003386 piperidinyl group Chemical group 0.000 claims description 9
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 8
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
- 238000003786 synthesis reaction Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 230000003511 endothelial effect Effects 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 6
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
- 102000008299 Nitric Oxide Synthase Human genes 0.000 claims description 4
- 108010021487 Nitric Oxide Synthase Proteins 0.000 claims description 4
- 230000014509 gene expression Effects 0.000 claims description 4
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 4
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 3
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims description 3
- XXOKIKKIMRAIDZ-UHFFFAOYSA-N 2-amino-n-(2,3-dihydro-1h-inden-2-yl)benzamide Chemical compound NC1=CC=CC=C1C(=O)NC1CC2=CC=CC=C2C1 XXOKIKKIMRAIDZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 3
- IGQDZYVWSOKCCO-UHFFFAOYSA-N 2-chloro-n-(2,3-dihydro-1h-inden-2-yl)-6-methylpyridine-3-carboxamide Chemical compound ClC1=NC(C)=CC=C1C(=O)NC1CC2=CC=CC=C2C1 IGQDZYVWSOKCCO-UHFFFAOYSA-N 0.000 claims description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
- KLMRGIURJNYXHB-UHFFFAOYSA-N 3-chloro-n-(2,3-dihydro-1h-inden-2-yl)-4-methylthiophene-2-carboxamide Chemical compound CC1=CSC(C(=O)NC2CC3=CC=CC=C3C2)=C1Cl KLMRGIURJNYXHB-UHFFFAOYSA-N 0.000 claims description 3
- WYRYWQXPSLVYJO-UHFFFAOYSA-N 3-chloro-n-(2,3-dihydro-1h-inden-2-yl)-4-propan-2-ylsulfonylthiophene-2-carboxamide Chemical compound CC(C)S(=O)(=O)C1=CSC(C(=O)NC2CC3=CC=CC=C3C2)=C1Cl WYRYWQXPSLVYJO-UHFFFAOYSA-N 0.000 claims description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 3
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 3
- QRENWBKXNZJPCB-UHFFFAOYSA-N 5-bromo-n-(2,3-dihydro-1h-inden-2-yl)thiophene-2-carboxamide Chemical compound S1C(Br)=CC=C1C(=O)NC1CC2=CC=CC=C2C1 QRENWBKXNZJPCB-UHFFFAOYSA-N 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- PYXHGQFGOJILPG-UHFFFAOYSA-N [2-(2,3-dihydro-1h-inden-2-ylcarbamoyl)-5-methylphenyl] acetate Chemical compound CC(=O)OC1=CC(C)=CC=C1C(=O)NC1CC2=CC=CC=C2C1 PYXHGQFGOJILPG-UHFFFAOYSA-N 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- QNKGSVMHFYKXMY-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-1h-indole-6-carboxamide Chemical compound C1=C2C=CNC2=CC(C(NC2CC3=CC=CC=C3C2)=O)=C1 QNKGSVMHFYKXMY-UHFFFAOYSA-N 0.000 claims description 3
- OKCJNSDIVCXYAL-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2,2-difluoro-1,3-benzodioxole-5-carboxamide Chemical compound C1C2=CC=CC=C2CC1NC(=O)C1=CC=C2OC(F)(F)OC2=C1 OKCJNSDIVCXYAL-UHFFFAOYSA-N 0.000 claims description 3
- ILSKEICCKVCVHE-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2,3-dihydro-1-benzofuran-5-carboxamide Chemical compound C1=C2OCCC2=CC(C(NC2CC3=CC=CC=C3C2)=O)=C1 ILSKEICCKVCVHE-UHFFFAOYSA-N 0.000 claims description 3
- WIMOSWXWAKVJHY-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2,5-dimethyl-1-(pyridin-4-ylmethyl)pyrrole-3-carboxamide Chemical compound CC1=CC(C(=O)NC2CC3=CC=CC=C3C2)=C(C)N1CC1=CC=NC=C1 WIMOSWXWAKVJHY-UHFFFAOYSA-N 0.000 claims description 3
- KPVOHHOWYRESDB-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2,5-dimethyl-1h-pyrrole-3-carboxamide Chemical compound N1C(C)=CC(C(=O)NC2CC3=CC=CC=C3C2)=C1C KPVOHHOWYRESDB-UHFFFAOYSA-N 0.000 claims description 3
- YSRBFWINKVMWLT-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-hydroxy-4-methylbenzamide Chemical compound OC1=CC(C)=CC=C1C(=O)NC1CC2=CC=CC=C2C1 YSRBFWINKVMWLT-UHFFFAOYSA-N 0.000 claims description 3
- NIHUGSQILVAFLW-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-3-methylthiophene-2-carboxamide Chemical compound C1=CSC(C(=O)NC2CC3=CC=CC=C3C2)=C1C NIHUGSQILVAFLW-UHFFFAOYSA-N 0.000 claims description 3
- LDRDLYITKGCQQZ-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-4-(methylamino)benzamide Chemical compound C1=CC(NC)=CC=C1C(=O)NC1CC2=CC=CC=C2C1 LDRDLYITKGCQQZ-UHFFFAOYSA-N 0.000 claims description 3
- NIXQKUWFMQZTOS-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-4-(trifluoromethyl)benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)NC1CC2=CC=CC=C2C1 NIXQKUWFMQZTOS-UHFFFAOYSA-N 0.000 claims description 3
- MPXUHFXUIZRORK-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-4-ethylsulfanylbenzamide Chemical compound C1=CC(SCC)=CC=C1C(=O)NC1CC2=CC=CC=C2C1 MPXUHFXUIZRORK-UHFFFAOYSA-N 0.000 claims description 3
- KJRZWIKUHMWWFM-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-4-methylsulfanylbenzamide Chemical compound C1=CC(SC)=CC=C1C(=O)NC1CC2=CC=CC=C2C1 KJRZWIKUHMWWFM-UHFFFAOYSA-N 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- LMHHFZAXSANGGM-UHFFFAOYSA-N 2-aminoindane Chemical compound C1=CC=C2CC(N)CC2=C1 LMHHFZAXSANGGM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- 206010020772 Hypertension Diseases 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 208000029078 coronary artery disease Diseases 0.000 claims description 2
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
- 238000007306 functionalization reaction Methods 0.000 claims description 2
- SWCDJGBAGZQBMO-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-5-methylthiophene-2-carboxamide Chemical compound S1C(C)=CC=C1C(=O)NC1CC2=CC=CC=C2C1 SWCDJGBAGZQBMO-UHFFFAOYSA-N 0.000 claims description 2
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 2
- 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims 8
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
- NQSTXRNSHFJLMH-UHFFFAOYSA-N 5-acetyl-n-(2,3-dihydro-1h-inden-2-yl)thiophene-2-carboxamide Chemical compound S1C(C(=O)C)=CC=C1C(=O)NC1CC2=CC=CC=C2C1 NQSTXRNSHFJLMH-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
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- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- KKJUPNGICOCCDW-UHFFFAOYSA-N 7-N,N-Dimethylamino-1,2,3,4,5-pentathiocyclooctane Chemical compound CN(C)C1CSSSSSC1 KKJUPNGICOCCDW-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
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Families Citing this family (97)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100074949A1 (en) | 2008-08-13 | 2010-03-25 | William Rowe | Pharmaceutical composition and administration thereof |
TWI241190B (en) * | 2001-02-13 | 2005-10-11 | Aventis Pharma Gmbh | 4-Fluoro-N-indan-2-yl benzamide and its use as pharmaceutical |
TWI243164B (en) * | 2001-02-13 | 2005-11-11 | Aventis Pharma Gmbh | Acylated indanyl amines and their use as pharmaceuticals |
AR035431A1 (es) * | 2001-02-13 | 2004-05-26 | Aventis Pharma Gmbh | 6,7,8,9-tetrahidro-5h-benzocicloheptenil aminas aciladas, un metodo para su sintesis, composiciones farmaceuticas y el uso de dichos compuestos para la fabricacion de medicamentos |
EP1388342A1 (en) * | 2002-08-07 | 2004-02-11 | Aventis Pharma Deutschland GmbH | Acylated, heteroaryl-condensed cycloalkenylamines and their use as pharmaceuticals |
US7186735B2 (en) | 2002-08-07 | 2007-03-06 | Sanofi-Aventis Deutschland Gmbh | Acylated arylcycloalkylamines and their use as pharmaceuticals |
US7105513B2 (en) * | 2002-08-07 | 2006-09-12 | Sanofi-Avertis Deutschland Gmbh | Acylated, heteroaryl-condensed cycloalkenylamines and their use as pharmaceuticals |
US7338956B2 (en) | 2002-08-07 | 2008-03-04 | Sanofi-Aventis Deutschland Gmbh | Acylamino-substituted heteroaromatic compounds and their use as pharmaceuticals |
GB0226931D0 (en) | 2002-11-19 | 2002-12-24 | Astrazeneca Ab | Chemical compounds |
US20040204383A1 (en) * | 2003-04-11 | 2004-10-14 | Gabor Tigyi | Lysophosphatidic acid analogs and inhibition of neointima formation |
US7132536B2 (en) * | 2003-04-24 | 2006-11-07 | Sanofi-Aventis Deutschland Gmbh | Triaza- and tetraaza-anthracenedione derivatives, their preparation and their use as pharmaceuticals |
GB0318464D0 (en) * | 2003-08-07 | 2003-09-10 | Astrazeneca Ab | Chemical compounds |
EP1529525A1 (en) * | 2003-11-06 | 2005-05-11 | Aventis Pharma Deutschland GmbH | ENOS transcription enhancers for use in the cell therapy of ischemic heart diseases |
US8309608B2 (en) * | 2003-11-06 | 2012-11-13 | Sanofi-Aventis Deutschland Gmbh | Use of eNOS transcription enhancers in the cell therapy of ischemic heart diseases |
JP2007519754A (ja) * | 2004-01-30 | 2007-07-19 | スミスクライン ビーチャム コーポレーション | 化合物 |
EP1568698A1 (en) | 2004-02-27 | 2005-08-31 | Aventis Pharma Deutschland GmbH | Pyrrole-derivatives as factor Xa inhibitors |
JP2008500358A (ja) * | 2004-05-25 | 2008-01-10 | メタボレックス インコーポレーティッド | Pparのモジュレーターとしての、二環式の置換されたトリアゾール、およびこれらの調製方法 |
CN101891680B (zh) * | 2004-06-24 | 2014-10-29 | 沃泰克斯药物股份有限公司 | Atp-结合弹夹转运蛋白的调控剂 |
US8354427B2 (en) | 2004-06-24 | 2013-01-15 | Vertex Pharmaceutical Incorporated | Modulators of ATP-binding cassette transporters |
JP2007277096A (ja) * | 2004-07-15 | 2007-10-25 | Astellas Pharma Inc | フェネチルニコチンアミド誘導体含有医薬 |
RU2392278C2 (ru) | 2004-07-15 | 2010-06-20 | Джапан Тобакко Инк. | Конденсированное производное бензамида и ингибитор активности подтипа 1 рецептора ваниллоида (vr1) |
WO2006040645A1 (en) * | 2004-10-11 | 2006-04-20 | Ranbaxy Laboratories Limited | N-(3,5-dichloropyridin-4-yl)-2,4,5-alkoxy and 2,3,4-alkoxy benzamide derivatives as pde-iv (phophodiesterase type-iv) inhibitors for the treatment of inflammatory diseases such as asthma |
KR101300046B1 (ko) * | 2004-10-14 | 2013-08-30 | 애보트 게엠베하 운트 콤파니 카게 | 도파민 d3 수용체 조절에 반응하는 질환 치료용으로 적합한 6-아미노(아자)인단 화합물 |
JP2008543785A (ja) * | 2005-06-09 | 2008-12-04 | バーテックス ファーマシューティカルズ インコーポレイテッド | イオンチャネルの調節因子としてのインダン誘導体 |
EP1741708A1 (en) | 2005-06-28 | 2007-01-10 | Sanofi-Aventis Deutschland GmbH | Heteroaryl-substituted amides comprising an unsaturated or cyclic linker group, and their use as pharmaceuticals |
EP1741709A1 (en) * | 2005-06-28 | 2007-01-10 | Sanofi-Aventis Deutschland GmbH | Heteroaryl-substituted amides comprising a saturated linker group, and their use as pharmaceuticals |
US7592461B2 (en) * | 2005-12-21 | 2009-09-22 | Bristol-Myers Squibb Company | Indane modulators of glucocorticoid receptor, AP-1, and/or NF-κB activity and use thereof |
EP1979367A2 (en) * | 2005-12-24 | 2008-10-15 | Vertex Pharmaceuticals Incorporated | Quinolin-4-one derivatives as modulators of abc transporters |
ES2624554T3 (es) | 2005-12-28 | 2017-07-14 | Vertex Pharmaceuticals Incorporated | Formas sólidas de n- [2,4 - bis (1,1 - dimetiletil) - 5 - hidroxifenil] - 1,4 - dihidro - 4 - oxoquinolina - 3 - carboxamida |
US7906508B2 (en) | 2005-12-28 | 2011-03-15 | Japan Tobacco Inc. | 3,4-dihydrobenzoxazine compounds and inhibitors of vanilloid receptor subtype 1 (VRI) activity |
PL1999114T3 (pl) | 2006-03-22 | 2015-12-31 | Hoffmann La Roche | Pirazole jako 11-Beta-HSD-1 |
CA2661017A1 (en) | 2006-08-24 | 2008-02-28 | Novartis Ag | Organic compounds |
US8236835B2 (en) | 2006-09-22 | 2012-08-07 | Novartis Ag | Heterocyclic inhibitors of stearoyl-CoA desaturase |
EP1905764A1 (en) | 2006-09-30 | 2008-04-02 | Sanofi-Aventis | Substituted 2-Phenyl-benzimidazoles and their use as pharmaceuticals |
EP1923062A1 (en) | 2006-11-16 | 2008-05-21 | sanofi-aventis | Imidazo[2,1-b]thiazoles and their use as pharmaceuticals |
EP1939180A1 (en) | 2006-12-20 | 2008-07-02 | sanofi-aventis | Heteroarylacrylamides and their use as pharmaceuticals for the stimulation of the expression of endothelial NO synthase |
EP1942104A1 (en) | 2006-12-20 | 2008-07-09 | sanofi-aventis | Heteroarylcyclopropanecarboxamides and their use as pharmaceuticals |
KR20090091337A (ko) | 2006-12-20 | 2009-08-27 | 노파르티스 아게 | Scd 억제제로서의 2-치환 5-원 헤테로사이클 |
EP1939181A1 (en) | 2006-12-27 | 2008-07-02 | sanofi-aventis | Heteroaryl-substituted carboxamides and use thereof for the stimulation of the expression of NO synthase |
EP1964841A1 (en) | 2007-02-28 | 2008-09-03 | sanofi-aventis | Imidazo[1,2-a]azine and their use as pharmaceuticals |
EP1964840A1 (en) | 2007-02-28 | 2008-09-03 | sanofi-aventis | Imidazo[1,2-a]pyridines and their use as pharmaceuticals |
EA011238B1 (ru) * | 2007-04-03 | 2009-02-27 | Марвел Лайфсайнсез Лтд. | Средство, обладающее противогипоксическим, противоинсультным, улучшающим память действием |
CN101903349B (zh) | 2007-08-27 | 2014-01-08 | Abbvie德国有限责任两合公司 | 4-(4-吡啶基)-苯甲酰胺及其作为rock活性调节剂的应用 |
TW200922558A (en) * | 2007-09-28 | 2009-06-01 | Mitsubishi Tanabe Pharma Corp | Indazole acrylic and amide compound |
EP2323978A1 (en) * | 2008-08-12 | 2011-05-25 | Takeda Pharmaceutical Company Limited | Amide compound |
CN101759683B (zh) * | 2008-12-25 | 2011-12-28 | 哈尔滨誉衡药业股份有限公司 | 二氢化茚酰胺化合物制备方法、包含其的药物组合物、及其作为蛋白激酶抑制剂的应用 |
EP2408750B1 (en) | 2009-03-20 | 2015-08-26 | Vertex Pharmaceuticals Incorporated | Process for making modulators of cystic fibrosis transmembrane conductance regulator |
WO2011115804A1 (en) | 2010-03-17 | 2011-09-22 | Ironwood Pharmaceuticals, Inc. | Sgc stimulators |
US20130137728A1 (en) * | 2010-03-24 | 2013-05-30 | MUSC Foundation for Research and Development | Compositions and Methods for the Treatment of Degenerative Diseases |
US8748442B2 (en) | 2010-06-30 | 2014-06-10 | Ironwood Pharmaceuticals, Inc. | sGC stimulators |
AU2011326241B2 (en) | 2010-11-09 | 2016-11-17 | Ironwood Pharmaceuticals, Inc. | sGC stimulators |
JP2014503504A (ja) * | 2010-11-24 | 2014-02-13 | ステマージ バイオテクノロジー エスエー | ミトコンドリアの電子伝達系の複合体iiiの活性の阻害剤、及び疾患を治療するためのその使用 |
US8802700B2 (en) | 2010-12-10 | 2014-08-12 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette transporters |
CN103018349B (zh) * | 2011-09-22 | 2015-04-08 | 北京美迪康信医药科技有限公司 | 一种二氢化茚酰胺化合物的检测分析方法 |
WO2013048928A1 (en) * | 2011-09-27 | 2013-04-04 | Bristol-Myers Squibb Company | Pyrrolinone carboxamide compounds useful as endothelial lipase inhibitors |
EP3112363A1 (en) | 2011-12-27 | 2017-01-04 | Ironwood Pharmaceuticals, Inc. | 2-[1-[(2-fluorophenyl)methyl]-5-(3-isoxazolyl)-1h-pyrazol-3-yl]-pyrimidine derivatives and related compounds as soluble guanylate cyclase (sgc) stimulators for the treatment of pulmonary hypertension |
NZ629199A (en) | 2012-02-27 | 2017-01-27 | Vertex Pharma | Pharmaceutical compositions comprising a solid dispersion of n-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide |
US9309235B2 (en) | 2012-09-18 | 2016-04-12 | Ironwood Pharmaceuticals, Inc. | SGC stimulators |
US9487508B2 (en) | 2012-09-19 | 2016-11-08 | Ironwood Pharmaceuticals, Inc. | SGC stimulators |
IL285564B2 (en) | 2013-03-15 | 2024-06-01 | Cyclerion Therapeutics Inc | sGC fans |
US10435364B2 (en) | 2013-04-17 | 2019-10-08 | Albert Ludwigs Universität Freiburg | Compounds for use as bromodomain inhibitors |
EP3092231B1 (en) | 2013-12-11 | 2018-06-27 | Ironwood Pharmaceuticals, Inc. | Sgc stimulators |
US20160324856A1 (en) | 2014-01-13 | 2016-11-10 | Ironwood Pharmaceuticals, Inc. | Use of sgc stimulators for the treatment of neuromuscular disorders |
ES2838573T3 (es) | 2014-08-21 | 2021-07-02 | Bristol Myers Squibb Co | Derivados de benzamida ligados como inhibidores potentes de ROCK |
US20170298055A1 (en) | 2014-09-17 | 2017-10-19 | Ironwood Pharmaceuticals, Inc. | sGC STIMULATORS |
MX2017003518A (es) | 2014-09-17 | 2017-07-28 | Ironwood Pharmaceuticals Inc | Estimuladores de guanilato ciclasa soluble (sgc). |
US20170291889A1 (en) | 2014-09-17 | 2017-10-12 | Ironwood Pharmaceuticals, Inc. | Pyrazole derivatives as sgc stimulators |
CA2963945C (en) | 2014-10-07 | 2023-01-10 | Vertex Pharmaceuticals Incorporated | Co-crystals of modulators of cystic fibrosis transmembrane conductance regulator |
EP4406616A3 (en) | 2014-11-06 | 2024-11-06 | Bial-R&D Investments, S.A. | Substituted pyrazolo(1,5-a)pyrimidines and their use in the treatment of medical disorders |
EP3215509B1 (en) | 2014-11-06 | 2020-02-26 | Lysosomal Therapeutics Inc. | Substituted pyrrolo[1,2-a]pyrimidines and their use in the treatment of medical disorders |
WO2016073889A1 (en) | 2014-11-06 | 2016-05-12 | Lysosomal Therapeutics Inc. | Substituted imidazo[1,5-a]pyrimidines and their use in the treatment of medical disorders |
CN107406369B (zh) | 2014-12-09 | 2021-01-15 | 以西结·戈兰 | 放纵行为调节剂 |
CN107406370A (zh) | 2014-12-09 | 2017-11-28 | 以西结·戈兰 | 酒精饮料替代品 |
ITUB20153978A1 (it) * | 2015-09-28 | 2017-03-28 | Laboratorio Chimico Int S P A | Procedimento per la preparazione di derivati di indanammina e di nuovi intermedi di sintesi. |
JP6855477B2 (ja) * | 2015-10-27 | 2021-04-07 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 血漿カリクレイン阻害薬としてのヘテロアリールカルボキサミド誘導体 |
US10399961B2 (en) * | 2015-10-27 | 2019-09-03 | Boehringer Ingelheim International Gmbh | Heteroarylcarboxamide derivatives as plasma kallikrein inhibitors |
GB201601301D0 (en) * | 2016-01-25 | 2016-03-09 | Takeda Pharmaceutical | Novel compounds |
JP7034935B2 (ja) | 2016-04-06 | 2022-03-14 | リソソーマル・セラピューティクス・インコーポレイテッド | ピロロ[1,2-a]ピリミジニルカルボキサミド化合物および医学的障害の処置におけるその使用 |
KR20230104752A (ko) | 2016-04-06 | 2023-07-10 | 비알 - 알&디 인베스트먼츠, 에스.에이. | 피라졸로[1,5-a]피리미디닐 카르복스아미드 화합물및 의학적 장애의 치료에서의 그의 용도 |
JP7046827B2 (ja) | 2016-04-06 | 2022-04-04 | リソソーマル・セラピューティクス・インコーポレイテッド | イミダゾ[1,5-a]ピリミジニルカルボキサミド化合物および医学的障害の処置におけるその使用 |
WO2017192930A1 (en) * | 2016-05-05 | 2017-11-09 | Lysosomal Therapeutics Inc. | SUBSTITUTED IMIDAZO[1,2-b]PYRIDAZINES, SUBSTITUTED IMIDAZO[1,5-b]PYRIDAZINES, RELATED COMPOUNDS, AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS |
EP3452455A4 (en) | 2016-05-05 | 2019-11-13 | Lysosomal Therapeutics Inc. | SUBSTITUTED IMDAZO [1,2-] PYRIDINES, SUBSTITUTED IMIDAZO [1,2-] PYRAZINES, RELATED COMPOUNDS AND THEIR USE IN THE TREATMENT OF ILLNESSES |
JP7016853B2 (ja) | 2016-07-07 | 2022-02-07 | サイクレリオン・セラピューティクス,インコーポレーテッド | sGC刺激剤のリンプロドラッグ |
KR20230074840A (ko) | 2016-07-07 | 2023-05-31 | 사이클리온 테라퓨틱스, 인크. | sGC 자극제의 고체 형태 |
GB201801355D0 (en) | 2018-01-26 | 2018-03-14 | Enterprise Therapeutics Ltd | Compounds |
US11708353B2 (en) | 2018-06-08 | 2023-07-25 | The General Hospital Corporation | Inhibitors of prolyl-tRNA-synthetase |
JP7378470B2 (ja) | 2018-10-10 | 2023-11-13 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 血漿カリクレイン阻害剤としてのフェニルテトラゾール誘導体 |
US10807973B2 (en) * | 2018-12-28 | 2020-10-20 | Endogena Therapeutics, Inc. | Compounds for use as therapeutically active substances in the treatment of retinal diseases |
CN113677334B (zh) * | 2019-02-01 | 2024-04-09 | 马歇尔大学科研协会 | 瞬时受体电位melastatin 8(trpm8)拮抗剂和相关方法 |
SG11202112212WA (en) * | 2019-05-03 | 2021-12-30 | Praxis Prec Medicines Inc | Kcnt1 inhibitors and methods of use |
TW202144330A (zh) | 2020-02-13 | 2021-12-01 | 德商百靈佳殷格翰國際股份有限公司 | 作為血漿激肽釋放酶抑制劑之雜芳族甲醯胺衍生物 |
TW202144331A (zh) | 2020-02-13 | 2021-12-01 | 德商百靈佳殷格翰國際股份有限公司 | 作為血漿激肽釋放酶抑制劑之雜芳族甲醯胺衍生物 |
US11773088B2 (en) | 2020-11-02 | 2023-10-03 | Praxis Precision Medicines, Inc. | KCNT1 inhibitors and methods of use |
WO2023098699A1 (en) * | 2021-12-01 | 2023-06-08 | Nanjing Immunophage Biotech Co., Ltd | Compounds and their uses as cd38 inhibitors |
WO2023211855A1 (en) * | 2022-04-25 | 2023-11-02 | Praxis Precision Medicines, Inc. | Kcnt1 inhibitors comprising a thiophene core and methods of use |
WO2024123716A1 (en) * | 2022-12-05 | 2024-06-13 | Praxis Precision Medicines, Inc. | Kcnt1 inhibitors comprising a sulfonamide ring core and methods of use |
WO2024159288A1 (pt) * | 2023-01-30 | 2024-08-08 | Eurofarma Laboratórios S.A. | Amidas bloqueadoras de nav 1.7 e/ou nav 1.8, seus processos de obtenção, composições, usos, métodos de tratamento destes e kits |
Family Cites Families (47)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1670282B2 (de) | 1967-10-24 | 1977-02-24 | Antidiabetisch wirksame hydrindensulfonylamino-pyrimidine sowie verfahren zu deren herstellung | |
US4192888A (en) | 1978-04-10 | 1980-03-11 | Smithkline Corporation | Pharmaceutical compositions and method of inhibiting phenylethanolamine N-methyltransferase |
AU543804B2 (en) | 1980-10-31 | 1985-05-02 | Takeda Chemical Industries Ltd. | Amides having bicyclic substituents on nitrogen |
CA2015473C (en) | 1989-04-28 | 1998-04-14 | Iwao Kinoshita | Triphenylmethane derivatives |
AU632809B2 (en) | 1989-05-25 | 1993-01-14 | Takeda Chemical Industries Ltd. | Benzocycloalkane benzopyran and benzothiopyran urea derivatives and production thereof |
EP0411507B1 (en) | 1989-08-02 | 1994-10-26 | Takeda Chemical Industries, Ltd. | Pyrazole derivatives, their production and use |
JPH03218371A (ja) | 1989-08-02 | 1991-09-25 | Takeda Chem Ind Ltd | ピラゾール誘導体 |
US5073566A (en) | 1989-11-30 | 1991-12-17 | Eli Lilly And Company | Angiotensin ii antagonist 1,3-imidazoles and use thereas |
AT392915B (de) | 1990-03-28 | 1991-07-10 | Chemiefaser Lenzing Ag | Verfahren zum abtrennen von wasser aus einer verduennten waesserigen loesung von n-methylmorpholin-n-oxid, n-methylmorpholin und/oder morpholin |
GB9010404D0 (en) * | 1990-05-09 | 1990-06-27 | Pfizer Ltd | Therapeutic agents |
CA2139088A1 (en) * | 1993-12-28 | 1995-06-29 | Akihiko Ishida | Indane derivatives, processes for preparing the same and synthetic intermediate of the same |
US5583221A (en) | 1994-05-04 | 1996-12-10 | Eli Lilly And Company | Substituted fused and bridged bicyclic compounds as therapeutic agents |
US5459274A (en) * | 1994-05-13 | 1995-10-17 | Hoechst-Roussel Pharmaceuticals Inc. | Preparation of N-alkyl-N-pyridinyl-1H-indol-1-amines |
TW397812B (en) | 1995-02-11 | 2000-07-11 | Astra Ab | Bicyclic isothiourea derivatives useful in therapy |
JPH0971534A (ja) | 1995-06-26 | 1997-03-18 | Tanabe Seiyaku Co Ltd | 医薬組成物 |
CA2225552A1 (en) | 1995-08-02 | 1997-02-13 | Chiroscience Limited | Quinolones and their therapeutic use |
ATE258437T1 (de) | 1995-08-02 | 2004-02-15 | Darwin Discovery Ltd | Chinolone und deren therapeutische verwendung |
BR9509297A (pt) * | 1995-08-10 | 1998-07-07 | Astra Ab | Composto composição farmacêutica utilização de um composto e processos de tratamento ou prolifaxia de uma doença ou condição na qual a síntese ou suprasintese da sintetase de óxido nitrico forma uma parte contribuinte e desordens neurodegenerativas ou de enxaqueca ou de prevenção e reversão da tolerância a opiatos e diazepinas ou de tratamento do vicio em tóxicos e de preparação de um composto |
JPH09255592A (ja) | 1996-01-17 | 1997-09-30 | Shionogi & Co Ltd | 不斉ボラン還元による光学活性アルコールの製造法 |
SE9701681D0 (sv) * | 1997-05-05 | 1997-05-05 | Astra Ab | New compounds |
CN1158264C (zh) * | 1997-11-21 | 2004-07-21 | Nps药物有限公司 | 用于治疗中枢神经系统疾病的代谢性谷氨酸受体拮抗剂 |
US6180597B1 (en) | 1998-03-19 | 2001-01-30 | Brigham And Women's Hospital, Inc. | Upregulation of Type III endothelial cell nitric oxide synthase by rho GTPase function inhibitors |
WO2000003746A2 (en) | 1998-07-14 | 2000-01-27 | The Brigham And Women's Hospital, Inc. | Upregulation of type iii endothelial cell nitric oxide synthase by agents that disrupt actin cytoskeletal organization |
NZ509252A (en) | 1998-08-20 | 2004-05-28 | Agouron Pharma | Non-peptide GnRH agents for treating GnRH associated diseases with pyrazole carboxamidine related structures |
US6326379B1 (en) * | 1998-09-16 | 2001-12-04 | Bristol-Myers Squibb Co. | Fused pyridine inhibitors of cGMP phosphodiesterase |
GB9825554D0 (en) * | 1998-11-20 | 1999-01-13 | Smithkline Beecham Spa | Novel Compounds |
DE19858191A1 (de) | 1998-12-17 | 2000-06-21 | Aventis Cropscience Gmbh | 4-Haloalkyl-3-heterocyclylpyridine und 4-Haloalkyl-5-heterocyclyl-pyrimidine und ihre Verwendung als Repellentien |
AUPP891299A0 (en) | 1999-02-26 | 1999-03-25 | Fujisawa Pharmaceutical Co., Ltd. | New 6-membered cyclic compounds |
GB9913083D0 (en) | 1999-06-04 | 1999-08-04 | Novartis Ag | Organic compounds |
PE20010306A1 (es) | 1999-07-02 | 2001-03-29 | Agouron Pharma | Compuestos de indazol y composiciones farmaceuticas que los contienen utiles para la inhibicion de proteina kinasa |
MY125533A (en) | 1999-12-06 | 2006-08-30 | Bristol Myers Squibb Co | Heterocyclic dihydropyrimidine compounds |
IT1317826B1 (it) | 2000-02-11 | 2003-07-15 | Dompe Spa | Ammidi, utili nell'inibizione della chemiotassi dei neutrofiliindotta da il-8. |
DE10019758A1 (de) * | 2000-04-20 | 2001-10-25 | Bayer Ag | Fungizide Wirkstoffkombinationen |
DE10021246A1 (de) | 2000-04-25 | 2001-10-31 | Schering Ag | Substituierte Benzoesäureamide und deren Verwendung als Arzneimittel |
GB0021831D0 (en) | 2000-09-06 | 2000-10-18 | Astrazeneca Ab | Chemical compounds |
WO2002024631A1 (en) * | 2000-09-18 | 2002-03-28 | Pharmacia & Upjohn Company | Process to prepare (2s)-2-(dipropylamino)-6-ethoxy-2,3-dihydro-1h-indene-5-carboxamide |
DE60138635D1 (de) | 2000-10-12 | 2009-06-18 | Merck & Co Inc | Aza- und polyaza naphthalenyl karboxamide als inhibitoren der hiv-integrase |
TWI241190B (en) * | 2001-02-13 | 2005-10-11 | Aventis Pharma Gmbh | 4-Fluoro-N-indan-2-yl benzamide and its use as pharmaceutical |
PE20020856A1 (es) * | 2001-02-13 | 2002-11-11 | Aventis Pharma Gmbh | 1,2,3,4-tetrahidronaftil aminas aciladas |
TWI243164B (en) * | 2001-02-13 | 2005-11-11 | Aventis Pharma Gmbh | Acylated indanyl amines and their use as pharmaceuticals |
AR035431A1 (es) * | 2001-02-13 | 2004-05-26 | Aventis Pharma Gmbh | 6,7,8,9-tetrahidro-5h-benzocicloheptenil aminas aciladas, un metodo para su sintesis, composiciones farmaceuticas y el uso de dichos compuestos para la fabricacion de medicamentos |
WO2002083648A1 (en) * | 2001-04-16 | 2002-10-24 | Eisai Co., Ltd. | Novel 1h-indazole compound |
US7263610B2 (en) * | 2002-07-30 | 2007-08-28 | Imagictv, Inc. | Secure multicast flow |
US7105513B2 (en) * | 2002-08-07 | 2006-09-12 | Sanofi-Avertis Deutschland Gmbh | Acylated, heteroaryl-condensed cycloalkenylamines and their use as pharmaceuticals |
US7186735B2 (en) * | 2002-08-07 | 2007-03-06 | Sanofi-Aventis Deutschland Gmbh | Acylated arylcycloalkylamines and their use as pharmaceuticals |
US7338956B2 (en) * | 2002-08-07 | 2008-03-04 | Sanofi-Aventis Deutschland Gmbh | Acylamino-substituted heteroaromatic compounds and their use as pharmaceuticals |
US8309608B2 (en) * | 2003-11-06 | 2012-11-13 | Sanofi-Aventis Deutschland Gmbh | Use of eNOS transcription enhancers in the cell therapy of ischemic heart diseases |
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