ZA200602993B - Organic compounds - Google Patents
Organic compounds Download PDFInfo
- Publication number
- ZA200602993B ZA200602993B ZA200602993A ZA200602993A ZA200602993B ZA 200602993 B ZA200602993 B ZA 200602993B ZA 200602993 A ZA200602993 A ZA 200602993A ZA 200602993 A ZA200602993 A ZA 200602993A ZA 200602993 B ZA200602993 B ZA 200602993B
- Authority
- ZA
- South Africa
- Prior art keywords
- methoxy
- hydroxy
- methyl
- amino
- isopropyl
- Prior art date
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- 150000002894 organic compounds Chemical class 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 379
- -1 acid amide compound Chemical class 0.000 claims description 298
- 125000003545 alkoxy group Chemical group 0.000 claims description 257
- 150000001875 compounds Chemical class 0.000 claims description 169
- 125000002947 alkylene group Chemical group 0.000 claims description 75
- 150000003839 salts Chemical class 0.000 claims description 68
- 229910052799 carbon Inorganic materials 0.000 claims description 49
- 229910052736 halogen Inorganic materials 0.000 claims description 46
- 150000002367 halogens Chemical group 0.000 claims description 46
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 34
- 239000000460 chlorine Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 108090000783 Renin Proteins 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 102100028255 Renin Human genes 0.000 claims description 23
- 239000008194 pharmaceutical composition Substances 0.000 claims description 23
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 19
- 230000000694 effects Effects 0.000 claims description 19
- 208000010877 cognitive disease Diseases 0.000 claims description 18
- 150000002431 hydrogen Chemical group 0.000 claims description 18
- 208000011580 syndromic disease Diseases 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 230000004410 intraocular pressure Effects 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 150000001721 carbon Chemical group 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 125000001589 carboacyl group Chemical group 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 208000019901 Anxiety disease Diseases 0.000 claims description 9
- 201000001320 Atherosclerosis Diseases 0.000 claims description 9
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 9
- 206010007572 Cardiac hypertrophy Diseases 0.000 claims description 9
- 208000006029 Cardiomegaly Diseases 0.000 claims description 9
- 208000031229 Cardiomyopathies Diseases 0.000 claims description 9
- 208000028698 Cognitive impairment Diseases 0.000 claims description 9
- 206010012289 Dementia Diseases 0.000 claims description 9
- 206010052337 Diastolic dysfunction Diseases 0.000 claims description 9
- 208000010412 Glaucoma Diseases 0.000 claims description 9
- 206010019280 Heart failures Diseases 0.000 claims description 9
- 206010019668 Hepatic fibrosis Diseases 0.000 claims description 9
- 206010020571 Hyperaldosteronism Diseases 0.000 claims description 9
- 206010020772 Hypertension Diseases 0.000 claims description 9
- 206010061216 Infarction Diseases 0.000 claims description 9
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 9
- 238000002399 angioplasty Methods 0.000 claims description 9
- 230000009787 cardiac fibrosis Effects 0.000 claims description 9
- 208000020832 chronic kidney disease Diseases 0.000 claims description 9
- 210000004351 coronary vessel Anatomy 0.000 claims description 9
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 9
- 206010012601 diabetes mellitus Diseases 0.000 claims description 9
- 208000017169 kidney disease Diseases 0.000 claims description 9
- 201000001119 neuropathy Diseases 0.000 claims description 9
- 230000007823 neuropathy Effects 0.000 claims description 9
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 9
- 201000009395 primary hyperaldosteronism Diseases 0.000 claims description 9
- 208000037803 restenosis Diseases 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 230000002159 abnormal effect Effects 0.000 claims description 8
- 229940030600 antihypertensive agent Drugs 0.000 claims description 8
- 239000002220 antihypertensive agent Substances 0.000 claims description 8
- 239000003524 antilipemic agent Substances 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 230000006444 vascular growth Effects 0.000 claims description 8
- 239000000883 anti-obesity agent Substances 0.000 claims description 7
- 239000003472 antidiabetic agent Substances 0.000 claims description 7
- 229940125710 antiobesity agent Drugs 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 6
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 6
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 5
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 229940125708 antidiabetic agent Drugs 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 150000002829 nitrogen Chemical class 0.000 claims description 4
- 239000001301 oxygen Chemical group 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- FNVOFDGAASRDQY-UHFFFAOYSA-N 3-amino-2,2-dimethylpropan-1-ol Chemical compound NCC(C)(C)CO FNVOFDGAASRDQY-UHFFFAOYSA-N 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000005325 aryloxy aryl group Chemical group 0.000 claims description 3
- IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- FXTQCVHVRHKYHV-UHFFFAOYSA-N 1-fluorocyclopentan-1-amine Chemical compound NC1(F)CCCC1 FXTQCVHVRHKYHV-UHFFFAOYSA-N 0.000 claims description 2
- TWASBYPJZBHZQJ-UHFFFAOYSA-N 1-methylcyclopentan-1-amine Chemical compound CC1(N)CCCC1 TWASBYPJZBHZQJ-UHFFFAOYSA-N 0.000 claims description 2
- NGZVNONVXYLYQW-UHFFFAOYSA-N 3,3,3-trifluoropropan-1-amine Chemical compound NCCC(F)(F)F NGZVNONVXYLYQW-UHFFFAOYSA-N 0.000 claims description 2
- CAOQEOHEZKVYOJ-UHFFFAOYSA-N cycloheptylmethanamine Chemical compound NCC1CCCCCC1 CAOQEOHEZKVYOJ-UHFFFAOYSA-N 0.000 claims description 2
- AVKNGPAMCBSNSO-UHFFFAOYSA-N cyclohexylmethanamine Chemical compound NCC1CCCCC1 AVKNGPAMCBSNSO-UHFFFAOYSA-N 0.000 claims description 2
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 8
- 150000004702 methyl esters Chemical class 0.000 claims 3
- SDMXLAZIFYYECU-UHFFFAOYSA-N 4-methoxycyclohexan-1-amine Chemical compound COC1CCC(N)CC1 SDMXLAZIFYYECU-UHFFFAOYSA-N 0.000 claims 2
- 150000003857 carboxamides Chemical class 0.000 claims 2
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 claims 2
- PDNZJLMPXLQDPL-UHFFFAOYSA-N (1-aminocyclopentyl)methanol Chemical compound OCC1(N)CCCC1 PDNZJLMPXLQDPL-UHFFFAOYSA-N 0.000 claims 1
- VVTJJJIVABEZIO-UHFFFAOYSA-N (1-methoxycyclopentyl)methanamine Chemical compound COC1(CN)CCCC1 VVTJJJIVABEZIO-UHFFFAOYSA-N 0.000 claims 1
- QOWBXWFYRXSBAS-UHFFFAOYSA-N (2,4-dimethoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C(OC)=C1 QOWBXWFYRXSBAS-UHFFFAOYSA-N 0.000 claims 1
- GDFBHCMFIUBEQT-UHFFFAOYSA-N (2,5-difluorophenyl)methanamine Chemical compound NCC1=CC(F)=CC=C1F GDFBHCMFIUBEQT-UHFFFAOYSA-N 0.000 claims 1
- PQCUDKMMPTXMAL-UHFFFAOYSA-N (2,6-difluorophenyl)methanamine Chemical compound NCC1=C(F)C=CC=C1F PQCUDKMMPTXMAL-UHFFFAOYSA-N 0.000 claims 1
- XEKGMBAKVJAVAZ-UHFFFAOYSA-N (2,6-dimethoxyphenyl)methanamine Chemical compound COC1=CC=CC(OC)=C1CN XEKGMBAKVJAVAZ-UHFFFAOYSA-N 0.000 claims 1
- KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-UHFFFAOYSA-N 0.000 claims 1
- LRFWYBZWRQWZIM-UHFFFAOYSA-N (2-fluorophenyl)methanamine Chemical compound NCC1=CC=CC=C1F LRFWYBZWRQWZIM-UHFFFAOYSA-N 0.000 claims 1
- CJAAPVQEZPAQNI-UHFFFAOYSA-N (2-methylphenyl)methanamine Chemical compound CC1=CC=CC=C1CN CJAAPVQEZPAQNI-UHFFFAOYSA-N 0.000 claims 1
- YVEJLBIEESKJLG-UHFFFAOYSA-N (2-methylsulfanylphenyl)methanamine Chemical compound CSC1=CC=CC=C1CN YVEJLBIEESKJLG-UHFFFAOYSA-N 0.000 claims 1
- PLXNYYYHSZRVJH-UHFFFAOYSA-N (2-pyrrolidin-1-ylphenyl)methanamine Chemical compound NCC1=CC=CC=C1N1CCCC1 PLXNYYYHSZRVJH-UHFFFAOYSA-N 0.000 claims 1
- PHLZUDXEBCQHKM-UHFFFAOYSA-N (3,4-difluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C(F)=C1 PHLZUDXEBCQHKM-UHFFFAOYSA-N 0.000 claims 1
- VJNGGOMRUHYAMC-UHFFFAOYSA-N (3,5-difluorophenyl)methanamine Chemical compound NCC1=CC(F)=CC(F)=C1 VJNGGOMRUHYAMC-UHFFFAOYSA-N 0.000 claims 1
- YGZJTYCCONJJGZ-UHFFFAOYSA-N (3,5-dimethoxyphenyl)methanamine Chemical compound COC1=CC(CN)=CC(OC)=C1 YGZJTYCCONJJGZ-UHFFFAOYSA-N 0.000 claims 1
- RGXUCUWVGKLACF-UHFFFAOYSA-N (3-methylphenyl)methanamine Chemical compound CC1=CC=CC(CN)=C1 RGXUCUWVGKLACF-UHFFFAOYSA-N 0.000 claims 1
- RVNBOLIRQOSAAX-UHFFFAOYSA-N (3-morpholin-4-ylphenyl)methanamine Chemical compound NCC1=CC=CC(N2CCOCC2)=C1 RVNBOLIRQOSAAX-UHFFFAOYSA-N 0.000 claims 1
- XLBYUDUEHVKUKQ-UHFFFAOYSA-N (3-pyrrol-1-ylphenyl)methanamine Chemical compound NCC1=CC=CC(N2C=CC=C2)=C1 XLBYUDUEHVKUKQ-UHFFFAOYSA-N 0.000 claims 1
- BXTWTBYGOKOWQX-UHFFFAOYSA-N (3-pyrrolidin-1-ylphenyl)methanamine Chemical compound NCC1=CC=CC(N2CCCC2)=C1 BXTWTBYGOKOWQX-UHFFFAOYSA-N 0.000 claims 1
- YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 claims 1
- HMTSWYPNXFHGEP-UHFFFAOYSA-N (4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1 HMTSWYPNXFHGEP-UHFFFAOYSA-N 0.000 claims 1
- YQSHYGCCYVPRDI-UHFFFAOYSA-N (4-propan-2-ylphenyl)methanamine Chemical compound CC(C)C1=CC=C(CN)C=C1 YQSHYGCCYVPRDI-UHFFFAOYSA-N 0.000 claims 1
- FGXCYGHFHAVYTE-UHFFFAOYSA-N (4-pyrrol-1-ylphenyl)methanamine Chemical compound C1=CC(CN)=CC=C1N1C=CC=C1 FGXCYGHFHAVYTE-UHFFFAOYSA-N 0.000 claims 1
- OCVQUKOCFUOCBM-UHFFFAOYSA-N (4-pyrrolidin-1-ylphenyl)methanamine Chemical compound C1=CC(CN)=CC=C1N1CCCC1 OCVQUKOCFUOCBM-UHFFFAOYSA-N 0.000 claims 1
- QTXFTOUAVPVJMZ-UHFFFAOYSA-N (4-thiophen-3-ylphenyl)methanamine Chemical compound C1=CC(CN)=CC=C1C1=CSC=C1 QTXFTOUAVPVJMZ-UHFFFAOYSA-N 0.000 claims 1
- OHQDEEKAUZTSQC-UHFFFAOYSA-N 1-(aminomethyl)-n,n-dimethylcyclopentan-1-amine Chemical compound CN(C)C1(CN)CCCC1 OHQDEEKAUZTSQC-UHFFFAOYSA-N 0.000 claims 1
- XUSXTHMTOSFZII-UHFFFAOYSA-N 1-(aminomethyl)cyclohexan-1-ol Chemical compound NCC1(O)CCCCC1 XUSXTHMTOSFZII-UHFFFAOYSA-N 0.000 claims 1
- JXJORHGRCCODBV-UHFFFAOYSA-N 1-(aminomethyl)cyclopropan-1-ol Chemical compound NCC1(O)CC1 JXJORHGRCCODBV-UHFFFAOYSA-N 0.000 claims 1
- ALMYLABZOCCULD-UHFFFAOYSA-N 1-(methoxymethyl)cyclopentan-1-amine Chemical compound COCC1(N)CCCC1 ALMYLABZOCCULD-UHFFFAOYSA-N 0.000 claims 1
- RIKUOLJPJNVTEP-UHFFFAOYSA-N 2-(2-fluorophenyl)ethanamine Chemical compound NCCC1=CC=CC=C1F RIKUOLJPJNVTEP-UHFFFAOYSA-N 0.000 claims 1
- KRQUFUKTQHISJB-YYADALCUSA-N 2-[(E)-N-[2-(4-chlorophenoxy)propoxy]-C-propylcarbonimidoyl]-3-hydroxy-5-(thian-3-yl)cyclohex-2-en-1-one Chemical compound CCC\C(=N/OCC(C)OC1=CC=C(Cl)C=C1)C1=C(O)CC(CC1=O)C1CCCSC1 KRQUFUKTQHISJB-YYADALCUSA-N 0.000 claims 1
- LMHHFZAXSANGGM-UHFFFAOYSA-N 2-aminoindane Chemical compound C1=CC=C2CC(N)CC2=C1 LMHHFZAXSANGGM-UHFFFAOYSA-N 0.000 claims 1
- KDFDOINBXBEOLZ-UHFFFAOYSA-N 2-phenylpropan-2-amine Chemical compound CC(C)(N)C1=CC=CC=C1 KDFDOINBXBEOLZ-UHFFFAOYSA-N 0.000 claims 1
- LFIWXXXFJFOECP-UHFFFAOYSA-N 4-(aminomethyl)benzonitrile Chemical compound NCC1=CC=C(C#N)C=C1 LFIWXXXFJFOECP-UHFFFAOYSA-N 0.000 claims 1
- IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 claims 1
- 206010001497 Agitation Diseases 0.000 claims 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 claims 1
- 241000283984 Rodentia Species 0.000 claims 1
- FYXMMFFZMQMXCQ-UHFFFAOYSA-N [2-(trifluoromethoxy)phenyl]methanamine Chemical compound NCC1=CC=CC=C1OC(F)(F)F FYXMMFFZMQMXCQ-UHFFFAOYSA-N 0.000 claims 1
- TUPUHSXMDIWJQT-UHFFFAOYSA-N [3-(trifluoromethoxy)phenyl]methanamine Chemical compound NCC1=CC=CC(OC(F)(F)F)=C1 TUPUHSXMDIWJQT-UHFFFAOYSA-N 0.000 claims 1
- DBGROTRFYBSUTR-UHFFFAOYSA-N [4-(trifluoromethoxy)phenyl]methanamine Chemical compound NCC1=CC=C(OC(F)(F)F)C=C1 DBGROTRFYBSUTR-UHFFFAOYSA-N 0.000 claims 1
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 claims 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
- NVSYANRBXPURRQ-UHFFFAOYSA-N naphthalen-1-ylmethanamine Chemical compound C1=CC=C2C(CN)=CC=CC2=C1 NVSYANRBXPURRQ-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 72
- 238000000034 method Methods 0.000 description 69
- 238000004128 high performance liquid chromatography Methods 0.000 description 58
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 43
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 27
- 238000012360 testing method Methods 0.000 description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 239000003112 inhibitor Substances 0.000 description 15
- 238000003818 flash chromatography Methods 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 108010064733 Angiotensins Proteins 0.000 description 10
- 102000015427 Angiotensins Human genes 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 101000579218 Homo sapiens Renin Proteins 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 238000001727 in vivo Methods 0.000 description 8
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 7
- 230000036772 blood pressure Effects 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 125000003282 alkyl amino group Chemical group 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 235000012239 silicon dioxide Nutrition 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- CJNRGSHEMCMUOE-UHFFFAOYSA-N 2-piperidin-1-ylethanamine Chemical compound NCCN1CCCCC1 CJNRGSHEMCMUOE-UHFFFAOYSA-N 0.000 description 5
- 102000004881 Angiotensinogen Human genes 0.000 description 5
- 108090001067 Angiotensinogen Proteins 0.000 description 5
- 241000282693 Cercopithecidae Species 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 5
- 125000005236 alkanoylamino group Chemical group 0.000 description 5
- 230000003178 anti-diabetic effect Effects 0.000 description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 210000003734 kidney Anatomy 0.000 description 5
- 230000001404 mediated effect Effects 0.000 description 5
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 5
- 239000002461 renin inhibitor Substances 0.000 description 5
- 229940086526 renin-inhibitors Drugs 0.000 description 5
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- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
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- C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/40—Y being a hydrogen or a carbon atom
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- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
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- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
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- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
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- C—CHEMISTRY; METALLURGY
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- C07C2601/00—Systems containing only non-condensed rings
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- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
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- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
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US52537403P | 2003-11-26 | 2003-11-26 |
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EP (2) | EP2266951A1 (cs) |
JP (1) | JP4884230B2 (cs) |
KR (1) | KR20060111530A (cs) |
CN (2) | CN102260188A (cs) |
AU (2) | AU2004293178B8 (cs) |
BR (1) | BRPI0417017A (cs) |
CA (1) | CA2600973C (cs) |
CO (1) | CO5700726A2 (cs) |
EC (1) | ECSP066561A (cs) |
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TN (1) | TNSN06156A1 (cs) |
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ZA (1) | ZA200602993B (cs) |
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EP2266951A1 (en) * | 2003-11-26 | 2010-12-29 | Novartis AG | Organic compounds |
GB0327839D0 (en) * | 2003-12-01 | 2003-12-31 | Novartis Ag | Organic compounds |
RU2407523C2 (ru) * | 2004-10-08 | 2010-12-27 | Новартис Аг | Применение ингибиторов ренина для профилактики или лечения диастолической дисфункции или диастолической сердечной недостаточности |
TW200631929A (en) * | 2004-12-10 | 2006-09-16 | Speedel Experimenta Ag | ω -phenyloctanamides |
JP2008532983A (ja) * | 2005-03-11 | 2008-08-21 | シュペーデル・エクスペリメンタ・アーゲー | レニン阻害剤として有用な複素環置換アルカンアミド |
GB0505969D0 (en) * | 2005-03-23 | 2005-04-27 | Novartis Ag | Organic compounds |
EP1764098A1 (en) * | 2005-09-17 | 2007-03-21 | Speedel Experimenta AG | Diaminoalcohols derivatives for the treatment of Alzheimer, malaria, HIV |
CA2622375A1 (en) * | 2005-09-17 | 2007-03-22 | Speedel Experimenta Ag | Alcanoic acid amides substituted by saturated o-heterocycles |
GB0521083D0 (en) * | 2005-10-17 | 2005-11-23 | Novartis Ag | Organic compounds |
EP2332526A3 (en) * | 2005-10-21 | 2011-10-12 | Novartis AG | Combination of a renin-inhibitor and an anti-dyslipidemic agent and/or an antiobesity agent |
GB2431649A (en) * | 2005-10-25 | 2007-05-02 | Novartis Ag | Alternative synthesis of aryl-octanoyl amide compounds |
GB2431653A (en) * | 2005-10-25 | 2007-05-02 | Novartis Ag | Alternative synthesis of aryl-octanoyl amide compounds |
GB2431648A (en) * | 2005-10-25 | 2007-05-02 | Novartis Ag | Alternative synthesis of aryl-octanoyl amide compounds |
GB2431640A (en) * | 2005-10-25 | 2007-05-02 | Novartis Ag | Alternative synthesis of aryl-octanoyl amide compounds |
GB2431641A (en) * | 2005-10-25 | 2007-05-02 | Novartis Ag | Alternative synthesis of aryl-octanoyl amide compounds |
GB2431646A (en) * | 2005-10-25 | 2007-05-02 | Novartis Ag | Alternative synthesis of aryl-octanoyl amide compounds |
GB2431645A (en) * | 2005-10-25 | 2007-05-02 | Novartis Ag | Alternative synthesis of aryl-octanoyl amide compounds |
GB2431642A (en) * | 2005-10-25 | 2007-05-02 | Novartis Ag | Alternative synthesis of aryl-octanoyl amide compounds |
AU2006332124B2 (en) | 2005-12-30 | 2011-03-03 | Novartis Ag | 3 , 5-substitgammaued piperidine compounds as renin inhibitors |
GB0611696D0 (en) * | 2006-06-13 | 2006-07-26 | Novartis Ag | Organic compounds |
GB0611697D0 (en) * | 2006-06-13 | 2006-07-26 | Novartis Ag | Organic compounds |
EP1867329A3 (en) * | 2006-06-14 | 2008-05-07 | Speedel Experimenta AG | 5-Amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxypropoxy)benzyl]-8-methylnonanamides as therapeutic compounds |
EP1872780A3 (en) * | 2006-06-14 | 2008-04-30 | Speedel Experimenta AG | Omega-Phenyloctanamides as therapeutic compounds |
TW200815324A (en) * | 2006-06-23 | 2008-04-01 | Daiichi Sankyo Co Ltd | Straight chain amine compound |
AU2007262004B2 (en) | 2006-06-23 | 2011-07-07 | Daiichi Sankyo Company, Limited | Cyclic amine compound |
EP1958666A1 (en) * | 2007-02-13 | 2008-08-20 | Speedel Experimenta AG | Heterocyclic-substituted alkanamides as therapeutic compounds |
WO2009000811A1 (en) | 2007-06-25 | 2008-12-31 | Novartis Ag | N5-(2-ethoxyethyl)-n3-(2-pyridinyl)-3,5-piperidinedicarboxamide derivatives for use as renin inhibitors |
JP5223686B2 (ja) * | 2009-01-07 | 2013-06-26 | 株式会社リコー | 撮像装置および撮像方法 |
IN2012DN00862A (cs) * | 2009-08-11 | 2015-07-10 | Novartis Ag | |
US8491927B2 (en) | 2009-12-02 | 2013-07-23 | Nimble Epitech, Llc | Pharmaceutical composition containing a hypomethylating agent and a histone deacetylase inhibitor |
CN102161627A (zh) * | 2011-02-24 | 2011-08-24 | 中国药科大学 | ω-(N取代-氨基烷基)辛酰胺 |
WO2012161173A1 (ja) * | 2011-05-23 | 2012-11-29 | 第一三共株式会社 | 置換アミド化合物 |
WO2012165314A1 (ja) * | 2011-05-27 | 2012-12-06 | 第一三共株式会社 | アミド化合物 |
WO2013045505A1 (en) | 2011-09-28 | 2013-04-04 | Novartis Ag | Biomarkers for raas combination therapy |
EP2810644A1 (en) | 2013-06-06 | 2014-12-10 | Ferrer Internacional, S.A. | Oral formulation for the treatment of cardiovascular diseases |
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IL96942A (en) * | 1990-01-31 | 1995-01-24 | Abbott Lab | A pharmaceutical mixture containing a history of amide prevents renin |
JPH0532602A (ja) * | 1991-07-26 | 1993-02-09 | Terumo Corp | ナフチルメチルアミン誘導体及びこれを含有するレニン阻害剤 |
JPH06199891A (ja) * | 1992-09-18 | 1994-07-19 | Japan Tobacco Inc | レニン阻害活性を有するアルコール誘導体及びその用途 |
DE4300388C2 (de) * | 1993-01-09 | 1995-03-16 | Metallgesellschaft Ag | Verfahren zur kontinuierlichen Einstellung und Regelung des pH-Wertes einer sauren Flüssigkeit, bei dem die kontinuierliche Messung des pH-Wertes mit einer Glaselektrode erfolgt |
MY119161A (en) * | 1994-04-18 | 2005-04-30 | Novartis Ag | Delta-amino-gamma-hydroxy-omega-aryl-alkanoic acid amides with enzyme especially renin inhibiting activities |
US5606078A (en) * | 1994-04-18 | 1997-02-25 | Ciba-Geigy Corporation | 3,5-Disubstituted tetrahydrofuran-2-ones |
US8168616B1 (en) | 2000-11-17 | 2012-05-01 | Novartis Ag | Combination comprising a renin inhibitor and an angiotensin receptor inhibitor for hypertension |
WO2003103653A1 (en) * | 2002-06-11 | 2003-12-18 | Elan Pharmaceuticals, Inc. | Methods of treating alzheimer's disease using aryl alkanoic acid amides |
EP2266951A1 (en) * | 2003-11-26 | 2010-12-29 | Novartis AG | Organic compounds |
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IS8513A (is) | 2006-06-19 |
NO20062968L (no) | 2006-08-28 |
WO2005051895A1 (en) | 2005-06-09 |
AU2004293178A1 (en) | 2005-06-09 |
CO5700726A2 (es) | 2006-11-30 |
KR20060111530A (ko) | 2006-10-27 |
RU2006122636A (ru) | 2008-01-27 |
US20090253703A1 (en) | 2009-10-08 |
AU2004293178B8 (en) | 2009-01-08 |
JP4884230B2 (ja) | 2012-02-29 |
IL175435A0 (en) | 2006-09-05 |
ECSP066561A (es) | 2006-10-17 |
US7919529B2 (en) | 2011-04-05 |
AU2009200957A1 (en) | 2009-04-02 |
AU2009200957B2 (en) | 2011-09-01 |
US20070135498A1 (en) | 2007-06-14 |
US20090253701A1 (en) | 2009-10-08 |
CA2600973C (en) | 2012-08-07 |
TNSN06156A1 (en) | 2007-11-15 |
US7582782B2 (en) | 2009-09-01 |
CN1882528A (zh) | 2006-12-20 |
US7851642B2 (en) | 2010-12-14 |
MA28175A1 (fr) | 2006-09-01 |
EP1689702B1 (en) | 2013-01-30 |
EP2266951A1 (en) | 2010-12-29 |
RU2413716C2 (ru) | 2011-03-10 |
CN102260188A (zh) | 2011-11-30 |
JP2007512283A (ja) | 2007-05-17 |
WO2005051895A8 (en) | 2006-07-20 |
BRPI0417017A (pt) | 2007-02-21 |
CA2600973A1 (en) | 2005-06-09 |
EP1689702A1 (en) | 2006-08-16 |
AU2004293178B2 (en) | 2008-12-11 |
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