NO328709B1 - Acylerte indanylaminer, fremgangsmate for fremstilling derav, og deres anvendelse for fremstilling av farmasoytiske midler, samt farmasoytiske preparater omfattende forbindelsene - Google Patents
Acylerte indanylaminer, fremgangsmate for fremstilling derav, og deres anvendelse for fremstilling av farmasoytiske midler, samt farmasoytiske preparater omfattende forbindelsene Download PDFInfo
- Publication number
- NO328709B1 NO328709B1 NO20033565A NO20033565A NO328709B1 NO 328709 B1 NO328709 B1 NO 328709B1 NO 20033565 A NO20033565 A NO 20033565A NO 20033565 A NO20033565 A NO 20033565A NO 328709 B1 NO328709 B1 NO 328709B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- group
- phenyl
- indan
- heteroaryl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 113
- 238000000034 method Methods 0.000 title claims description 27
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical class C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title claims description 9
- 239000008177 pharmaceutical agent Substances 0.000 title claims description 7
- 230000008569 process Effects 0.000 title claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- -1 monosubstituted phenyl Chemical group 0.000 claims description 493
- 125000001424 substituent group Chemical group 0.000 claims description 152
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 112
- 229910052736 halogen Inorganic materials 0.000 claims description 96
- 150000002367 halogens Chemical class 0.000 claims description 84
- 125000001072 heteroaryl group Chemical group 0.000 claims description 79
- 239000000203 mixture Substances 0.000 claims description 76
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 75
- 125000002577 pseudohalo group Chemical group 0.000 claims description 71
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 150000003839 salts Chemical class 0.000 claims description 48
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 229910052731 fluorine Inorganic materials 0.000 claims description 32
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 30
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 26
- 125000005842 heteroatom Chemical group 0.000 claims description 26
- 239000000243 solution Substances 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 21
- 238000011282 treatment Methods 0.000 claims description 21
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 20
- LMHHFZAXSANGGM-UHFFFAOYSA-N 2-aminoindane Chemical compound C1=CC=C2CC(N)CC2=C1 LMHHFZAXSANGGM-UHFFFAOYSA-N 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 15
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
- 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 14
- 230000003511 endothelial effect Effects 0.000 claims description 14
- 230000014509 gene expression Effects 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 230000009467 reduction Effects 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000002883 imidazolyl group Chemical group 0.000 claims description 11
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 11
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 10
- 201000001320 Atherosclerosis Diseases 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 208000029078 coronary artery disease Diseases 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 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 7
- 206010002383 Angina Pectoris Diseases 0.000 claims description 7
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 7
- 208000002249 Diabetes Complications Diseases 0.000 claims description 7
- 102000008299 Nitric Oxide Synthase Human genes 0.000 claims description 7
- 108010021487 Nitric Oxide Synthase Proteins 0.000 claims description 7
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 239000003826 tablet Substances 0.000 claims description 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 6
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
- PAPNRQCYSFBWDI-UHFFFAOYSA-N 2,5-Dimethyl-1H-pyrrole Chemical compound CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 claims description 6
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 6
- 206010048554 Endothelial dysfunction Diseases 0.000 claims description 6
- 206010019280 Heart failures Diseases 0.000 claims description 6
- 206010020772 Hypertension Diseases 0.000 claims description 6
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 6
- 208000007718 Stable Angina Diseases 0.000 claims description 6
- 206010047281 Ventricular arrhythmia Diseases 0.000 claims description 6
- 230000008694 endothelial dysfunction Effects 0.000 claims description 6
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 6
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
- XIZXADDGOCJZAL-UHFFFAOYSA-N 3h-dioxole-5-carboxylic acid Chemical compound OC(=O)C1=CCOO1 XIZXADDGOCJZAL-UHFFFAOYSA-N 0.000 claims description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
- 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 5
- KKJUPNGICOCCDW-UHFFFAOYSA-N 7-N,N-Dimethylamino-1,2,3,4,5-pentathiocyclooctane Chemical compound CN(C)C1CSSSSSC1 KKJUPNGICOCCDW-UHFFFAOYSA-N 0.000 claims description 5
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims description 5
- 206010012655 Diabetic complications Diseases 0.000 claims description 5
- 208000007536 Thrombosis Diseases 0.000 claims description 5
- 208000007814 Unstable Angina Diseases 0.000 claims description 5
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 5
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 230000006378 damage Effects 0.000 claims description 5
- 125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 239000007903 gelatin capsule Substances 0.000 claims description 5
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 239000007924 injection Substances 0.000 claims description 5
- 238000002347 injection Methods 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- 208000010125 myocardial infarction Diseases 0.000 claims description 5
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 5
- 125000003226 pyrazolyl 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
- 208000037803 restenosis Diseases 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- 230000002792 vascular Effects 0.000 claims description 5
- 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 4
- 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 4
- 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 4
- 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 description 4
- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 4
- 208000007530 Essential hypertension Diseases 0.000 claims description 4
- 206010016654 Fibrosis Diseases 0.000 claims description 4
- 206010018367 Glomerulonephritis chronic Diseases 0.000 claims description 4
- 208000001132 Osteoporosis Diseases 0.000 claims description 4
- 201000003099 Renovascular Hypertension Diseases 0.000 claims description 4
- 208000017442 Retinal disease Diseases 0.000 claims description 4
- 206010038923 Retinopathy Diseases 0.000 claims description 4
- 201000004239 Secondary hypertension Diseases 0.000 claims description 4
- 208000006011 Stroke Diseases 0.000 claims description 4
- 230000033115 angiogenesis Effects 0.000 claims description 4
- 210000001367 artery Anatomy 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 208000020832 chronic kidney disease Diseases 0.000 claims description 4
- 230000007882 cirrhosis Effects 0.000 claims description 4
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 4
- 229940124558 contraceptive agent Drugs 0.000 claims description 4
- 239000003433 contraceptive agent Substances 0.000 claims description 4
- 239000008298 dragée Substances 0.000 claims description 4
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 4
- 239000000839 emulsion Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000007943 implant Substances 0.000 claims description 4
- 201000001881 impotence Diseases 0.000 claims description 4
- 238000001802 infusion Methods 0.000 claims description 4
- 208000017169 kidney disease Diseases 0.000 claims description 4
- 210000004185 liver Anatomy 0.000 claims description 4
- 239000003094 microcapsule Substances 0.000 claims description 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- YWMOQNRLTYZRJR-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-5-methyl-1-phenylpyrazole-4-carboxamide Chemical compound CC1=C(C(=O)NC2CC3=CC=CC=C3C2)C=NN1C1=CC=CC=C1 YWMOQNRLTYZRJR-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 239000007922 nasal spray Substances 0.000 claims description 4
- 239000006187 pill Substances 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 239000007940 sugar coated tablet Substances 0.000 claims description 4
- 239000000829 suppository Substances 0.000 claims description 4
- 239000006188 syrup Substances 0.000 claims description 4
- 235000020357 syrup Nutrition 0.000 claims description 4
- 125000004463 2,4-dimethyl-thiazol-5-yl group Chemical group CC=1SC(=C(N1)C)* 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
- KRHMOVIJQRSYJV-UHFFFAOYSA-N 2-bromo-4-chloro-n-(2,3-dihydro-1h-inden-2-yl)benzamide Chemical compound BrC1=CC(Cl)=CC=C1C(=O)NC1CC2=CC=CC=C2C1 KRHMOVIJQRSYJV-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
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 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
- 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
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- LEKWXWJZSOPFII-UHFFFAOYSA-N 4-bromo-2-chloro-n-(2,3-dihydro-1h-inden-2-yl)benzamide Chemical compound ClC1=CC(Br)=CC=C1C(=O)NC1CC2=CC=CC=C2C1 LEKWXWJZSOPFII-UHFFFAOYSA-N 0.000 claims description 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 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
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 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
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 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
- 239000008187 granular material Substances 0.000 claims description 3
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- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 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
- 239000002674 ointment Substances 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
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 3
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- 125000003944 tolyl group Chemical group 0.000 claims description 3
- 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 description 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
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- 238000007306 functionalization reaction Methods 0.000 claims description 2
- 230000002093 peripheral effect Effects 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
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 13
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- 229940079593 drug Drugs 0.000 claims 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 239000000443 aerosol Substances 0.000 claims 2
- 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 2
- 229940097496 nasal spray Drugs 0.000 claims 2
- 229940098465 tincture Drugs 0.000 claims 2
- 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
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
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- 125000000732 arylene group Chemical group 0.000 claims 1
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Classifications
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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 |
MY136316A (en) * | 2001-02-13 | 2008-09-30 | Sanofi Aventis Deutschland | Acylated 6,7,8,9-tetrahydro-5h-benzocycloheptenyl amines and their use as pharmaceutical. |
TWI243164B (en) * | 2001-02-13 | 2005-11-11 | Aventis Pharma Gmbh | Acylated indanyl amines and their use as pharmaceuticals |
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 |
US7338956B2 (en) | 2002-08-07 | 2008-03-04 | Sanofi-Aventis Deutschland Gmbh | Acylamino-substituted heteroaromatic compounds 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 |
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 |
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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 |
US20060014785A1 (en) * | 2004-05-25 | 2006-01-19 | Metabolex, Inc. | Bicyclic, substituted triazoles as modulators of ppar and methods of their preparation |
US8354427B2 (en) * | 2004-06-24 | 2013-01-15 | Vertex Pharmaceutical Incorporated | Modulators of ATP-binding cassette transporters |
EP2522659A3 (en) | 2004-06-24 | 2013-11-27 | Vertex Pharmaceuticals 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 |
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