NO310069B1 - Nye-4-(oksyalkoksyfenyl)-3-oksy-piperidiner for behandling av hjerte- og nyreinsuffisiens - Google Patents

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Publication number

NO310069B1

NO310069B1 NO980954A NO980954A NO310069B1 NO 310069 B1 NO310069 B1 NO 310069B1 NO 980954 A NO980954 A NO 980954A NO 980954 A NO980954 A NO 980954A NO 310069 B1 NO310069 B1 NO 310069B1

Authority

NO

Norway

Prior art keywords

alkyl

alkoxy

phenyl

ylmethoxy

naphthalen

Prior art date

1995-09-07

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• 206010019280 Heart failures Diseases 0.000 title claims description 5
• 208000001647 Renal Insufficiency Diseases 0.000 title claims description 4
• 201000006370 kidney failure Diseases 0.000 title description 2
• 230000000747 cardiac effect Effects 0.000 title 1
• -1 cyano, carboxy Chemical group 0.000 claims description 248
• 150000001875 compounds Chemical class 0.000 claims description 187
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 101
• 238000000034 method Methods 0.000 claims description 95
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 84
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 51
• 229960000583 acetic acid Drugs 0.000 claims description 38
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
• 125000000217 alkyl group Chemical group 0.000 claims description 26
• 239000001257 hydrogen Substances 0.000 claims description 24
• 229910052739 hydrogen Inorganic materials 0.000 claims description 24
• 229910052736 halogen Inorganic materials 0.000 claims description 23
• 150000002367 halogens Chemical class 0.000 claims description 22
• 125000006239 protecting group Chemical group 0.000 claims description 21
• 150000003839 salts Chemical class 0.000 claims description 21
• 125000001424 substituent group Chemical group 0.000 claims description 21
• 125000004432 carbon atom Chemical group C* 0.000 claims description 20
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
• 125000001624 naphthyl group Chemical group 0.000 claims description 18
• 238000010992 reflux Methods 0.000 claims description 18
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
• 125000004076 pyridyl group Chemical group 0.000 claims description 17
• 150000002431 hydrogen Chemical class 0.000 claims description 15
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
• 239000012362 glacial acetic acid Substances 0.000 claims description 10
• 239000003960 organic solvent Substances 0.000 claims description 10
• 125000004043 oxo group Chemical group O=* 0.000 claims description 10
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 10
• 238000002360 preparation method Methods 0.000 claims description 9
• 229920006395 saturated elastomer Polymers 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 239000001301 oxygen Substances 0.000 claims description 8
• VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims description 8
• 206010020772 Hypertension Diseases 0.000 claims description 7
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 7
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
• ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• 125000005842 heteroatom Chemical group 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• 125000001425 triazolyl group Chemical group 0.000 claims description 6
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
• 239000011701 zinc Substances 0.000 claims description 6
• 229910052725 zinc Inorganic materials 0.000 claims description 6
• 125000005605 benzo group Chemical group 0.000 claims description 5
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
• 238000005903 acid hydrolysis reaction Methods 0.000 claims description 4
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 4
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 229910052757 nitrogen Inorganic materials 0.000 claims description 4
• 125000000951 phenoxy group Chemical class [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
• 239000002461 renin inhibitor Substances 0.000 claims description 4
• 229940086526 renin-inhibitors Drugs 0.000 claims description 4
• 239000011593 sulfur Substances 0.000 claims description 4
• 229940102001 zinc bromide Drugs 0.000 claims description 4
• WUKPAJHFMBKCMX-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-ylmethoxy)-4-(4-fluorophenyl)piperidine Chemical compound C1=CC(F)=CC=C1C1C(OCC=2C=C3OCOC3=CC=2)CNCC1 WUKPAJHFMBKCMX-UHFFFAOYSA-N 0.000 claims description 3
• 239000005977 Ethylene Substances 0.000 claims description 3
• 125000004414 alkyl thio group Chemical group 0.000 claims description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
• FZAFAUXIODKSBH-KZXHCJOXSA-N (2r)-3-[7-[[(3r,4r)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxymethyl]naphthalen-2-yl]oxypropane-1,2-diol Chemical compound C1=CC([C@H]2CCNC[C@@H]2OCC=2C=CC3=CC=C(C=C3C=2)OC[C@H](O)CO)=CC=C1OCCCOCC1=CC=CC=C1 FZAFAUXIODKSBH-KZXHCJOXSA-N 0.000 claims description 2
• FZAFAUXIODKSBH-MYZAEBQFSA-N (2s)-3-[7-[[(3r,4r)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxymethyl]naphthalen-2-yl]oxypropane-1,2-diol Chemical compound C1=CC([C@H]2CCNC[C@@H]2OCC=2C=CC3=CC=C(C=C3C=2)OC[C@@H](O)CO)=CC=C1OCCCOCC1=CC=CC=C1 FZAFAUXIODKSBH-MYZAEBQFSA-N 0.000 claims description 2
• OIOVXGGCZBNFSE-SYBRLPANSA-N (3r,4r)-3-[(1,4-dimethoxynaphthalen-2-yl)methoxy]-4-[4-[3-(2-methoxyphenoxy)propoxy]phenyl]piperidine Chemical compound COC1=CC=CC=C1OCCCOC1=CC=C([C@@H]2[C@H](CNCC2)OCC=2C(=C3C=CC=CC3=C(OC)C=2)OC)C=C1 OIOVXGGCZBNFSE-SYBRLPANSA-N 0.000 claims description 2
• GQZNHBAQKXQYIV-SJHOIFEDSA-N (3r,4r)-3-[(1,4-dimethoxynaphthalen-2-yl)methoxy]-4-[4-[3-[(2-methoxyphenyl)methoxy]propoxy]phenyl]piperidine Chemical compound COC1=CC=CC=C1COCCCOC1=CC=C([C@@H]2[C@H](CNCC2)OCC=2C(=C3C=CC=CC3=C(OC)C=2)OC)C=C1 GQZNHBAQKXQYIV-SJHOIFEDSA-N 0.000 claims description 2
• NOZRXDYWCRPRSB-MPZFMJHNSA-N (3r,4r,5s)-3-[(1,4-dimethoxynaphthalen-2-yl)methoxy]-4-[4-[3-[(2-methoxyphenyl)methoxy]propoxy]phenyl]-5-(2h-tetrazol-5-ylmethyl)piperidine Chemical compound COC1=CC=CC=C1COCCCOC1=CC=C([C@@H]2[C@H](CNC[C@H]2CC=2NN=NN=2)OCC=2C(=C3C=CC=CC3=C(OC)C=2)OC)C=C1 NOZRXDYWCRPRSB-MPZFMJHNSA-N 0.000 claims description 2
• WUAIVTZASDYIOE-XLDNGHKCSA-N (3s,4r,5r)-3-(methoxymethyl)-5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidine Chemical compound C1=CC([C@@H]2[C@@H](OCC=3C=C4C=CC=CC4=CC=3)CNC[C@H]2COC)=CC=C1OCCCOCC1=CC=CC=C1 WUAIVTZASDYIOE-XLDNGHKCSA-N 0.000 claims description 2
• UNIHNYUCROCRPH-ULNSLHSMSA-N (3s,4s,5r)-5-[(4-methoxyphenyl)methoxy]-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-ol Chemical compound C1=CC(OC)=CC=C1CO[C@@H]1[C@@H](C=2C=CC(OCCCOCC=3C=CC=CC=3)=CC=2)[C@H](O)CNC1 UNIHNYUCROCRPH-ULNSLHSMSA-N 0.000 claims description 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
• OBPFLVNGKXWSPT-SYRLMZQMSA-N 1-[[(3s,4r,5r)-5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]methyl]imidazolidin-2-one Chemical compound O=C1NCCN1C[C@H]1[C@H](C=2C=CC(OCCCOCC=3C=CC=CC=3)=CC=2)[C@@H](OCC=2C=C3C=CC=CC3=CC=2)CNC1 OBPFLVNGKXWSPT-SYRLMZQMSA-N 0.000 claims description 2
• TWSDLMCSIFRJDC-VIZCGCQYSA-N 2-(4-cyclohexylbutoxy)-5-[(3r,4r)-3-[(1,4-dimethoxynaphthalen-2-yl)methoxy]piperidin-4-yl]pyrimidine Chemical compound N1=CC([C@H]2CCNC[C@@H]2OCC=2C=C(C3=CC=CC=C3C=2OC)OC)=CN=C1OCCCCC1CCCCC1 TWSDLMCSIFRJDC-VIZCGCQYSA-N 0.000 claims description 2
• PJZUGRXNVXFQNC-PLJDCMBSSA-N 3-[(3s,4s,5r)-5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxypropan-1-ol Chemical compound C1=CC([C@@H]2[C@@H](OCC=3C=C4C=CC=CC4=CC=3)CNC[C@H]2OCCCO)=CC=C1OCCCOCC1=CC=CC=C1 PJZUGRXNVXFQNC-PLJDCMBSSA-N 0.000 claims description 2
• SHAMCHNYKIYNST-AMAPPZPBSA-N 4-[2-[7-[[(3r,4r)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxymethyl]naphthalen-2-yl]oxyethyl]morpholine Chemical compound C=1C=C([C@@H]2[C@H](CNCC2)OCC=2C=C3C=C(OCCN4CCOCC4)C=CC3=CC=2)C=CC=1OCCCOCC1=CC=CC=C1 SHAMCHNYKIYNST-AMAPPZPBSA-N 0.000 claims description 2
• BGAWAKUWOBKLJF-MINDXDAISA-N 4-[2-[[(3s,4r,5r)-5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]methoxy]ethyl]morpholine Chemical compound C=1C=C([C@@H]2[C@H](CNC[C@H]2COCCN2CCOCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCCOCC1=CC=CC=C1 BGAWAKUWOBKLJF-MINDXDAISA-N 0.000 claims description 2
• UXRWZYYMQOXLII-PPTMTGTBSA-N 7-[[(3r,4r)-4-[4-[3-[(2-methoxyphenyl)methoxy]propoxy]phenyl]piperidin-3-yl]oxymethyl]-1,2,3,4-tetrahydroquinoline Chemical compound COC1=CC=CC=C1COCCCOC1=CC=C([C@@H]2[C@H](CNCC2)OCC=2C=C3NCCCC3=CC=2)C=C1 UXRWZYYMQOXLII-PPTMTGTBSA-N 0.000 claims description 2
• OTVOEZNYPLBKLK-PPTMTGTBSA-N 7-[[(3r,4r)-4-[4-[3-[(2-methoxyphenyl)methoxy]propoxy]phenyl]piperidin-3-yl]oxymethyl]quinoline Chemical compound COC1=CC=CC=C1COCCCOC1=CC=C([C@@H]2[C@H](CNCC2)OCC=2C=C3N=CC=CC3=CC=2)C=C1 OTVOEZNYPLBKLK-PPTMTGTBSA-N 0.000 claims description 2
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
• RQVPNCSWOUIVAQ-RGRQWMLTSA-N [(3s,4r,5r)-5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]methanol Chemical compound C1=CC([C@@H]2[C@@H](OCC=3C=C4C=CC=CC4=CC=3)CNC[C@H]2CO)=CC=C1OCCCOCC1=CC=CC=C1 RQVPNCSWOUIVAQ-RGRQWMLTSA-N 0.000 claims description 2
• 239000013543 active substance Substances 0.000 claims description 2
• 125000002947 alkylene group Chemical group 0.000 claims description 2
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
• 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
• 239000003814 drug Substances 0.000 claims description 2
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
• 125000002757 morpholinyl group Chemical group 0.000 claims description 2
• ABNIRSHNIAQENF-RHNUXINZSA-N n-ethyl-n-[[(3s,4r,5r)-5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]methyl]ethanamine Chemical compound C1=CC([C@@H]2[C@@H](OCC=3C=C4C=CC=CC4=CC=3)CNC[C@H]2CN(CC)CC)=CC=C1OCCCOCC1=CC=CC=C1 ABNIRSHNIAQENF-RHNUXINZSA-N 0.000 claims description 2
• 125000002971 oxazolyl group Chemical group 0.000 claims description 2
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• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
• 125000004434 sulfur atom Chemical group 0.000 claims description 2
• 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 2
• 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 2
• 125000004306 triazinyl group Chemical group 0.000 claims description 2
• 239000004146 Propane-1,2-diol Substances 0.000 claims 2
• 239000000571 coke Substances 0.000 claims 2
• 229960004063 propylene glycol Drugs 0.000 claims 2
• NEPVAKOZRPVHEM-RTBURBONSA-N (3r,4r)-3-(3-chlorophenoxy)-4-(3,4-dimethylphenoxy)piperidine Chemical compound C1=C(C)C(C)=CC=C1O[C@H]1[C@H](OC=2C=C(Cl)C=CC=2)CNCC1 NEPVAKOZRPVHEM-RTBURBONSA-N 0.000 claims 1
• CKFYLSMACGXFQB-XHFCRVKJSA-N 4-[[(3s,4r,5r)-5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]methylsulfanyl]pyridine Chemical compound C=1C=C([C@@H]2[C@H](CNC[C@H]2CSC=2C=CN=CC=2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCCOCC1=CC=CC=C1 CKFYLSMACGXFQB-XHFCRVKJSA-N 0.000 claims 1
• YNZOWKPPAKUTGP-ZUKKLESISA-N 5-[(3r,4r)-3-[(1,4-dimethoxynaphthalen-2-yl)methoxy]piperidin-4-yl]-2-[3-[(2-methoxyphenyl)methoxy]propoxy]pyridine Chemical compound COC1=CC=CC=C1COCCCOC1=CC=C([C@@H]2[C@H](CNCC2)OCC=2C(=C3C=CC=CC3=C(OC)C=2)OC)C=N1 YNZOWKPPAKUTGP-ZUKKLESISA-N 0.000 claims 1
• 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims 1
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• 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 claims 1
• 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
• 229910052731 fluorine Inorganic materials 0.000 claims 1
• 239000011737 fluorine Substances 0.000 claims 1
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 474
• 239000007787 solid Substances 0.000 description 261
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• 239000000243 solution Substances 0.000 description 249
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• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 188
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• 239000003921 oil Substances 0.000 description 110
• 235000019198 oils Nutrition 0.000 description 110
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