HRP20040349A2 - Benzoxazine and benzothiazine derivatives and pharmaceutical compositions containing them - Google Patents

Info

Publication number

HRP20040349A2

HRP20040349A2 HR20040349A HRP20040349A HRP20040349A2 HR P20040349 A2 HRP20040349 A2 HR P20040349A2 HR 20040349 A HR20040349 A HR 20040349A HR P20040349 A HRP20040349 A HR P20040349A HR P20040349 A2 HRP20040349 A2 HR P20040349A2

Authority

HR

Croatia

Prior art keywords

benzo

dihydro

oxazin

phenyl

propylamino

Prior art date

2001-10-16

Links

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• Global Dossier
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• 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
• UJVBZCCNLAAMOV-UHFFFAOYSA-N 2h-1,2-benzothiazine Chemical class C1=CC=C2C=CNSC2=C1 UJVBZCCNLAAMOV-UHFFFAOYSA-N 0.000 title 1
• CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 306
• 150000003839 salts Chemical class 0.000 claims description 161
• 125000003118 aryl group Chemical group 0.000 claims description 153
• 125000000217 alkyl group Chemical group 0.000 claims description 127
• -1 hydroxy, formyl Chemical group 0.000 claims description 109
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 97
• 238000006243 chemical reaction Methods 0.000 claims description 84
• 239000001257 hydrogen Substances 0.000 claims description 83
• 229910052739 hydrogen Inorganic materials 0.000 claims description 83
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 65
• 238000000034 method Methods 0.000 claims description 63
• 239000000243 solution Substances 0.000 claims description 54
• 125000003545 alkoxy group Chemical group 0.000 claims description 50
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 49
• 125000000623 heterocyclic group Chemical group 0.000 claims description 48
• 125000001072 heteroaryl group Chemical group 0.000 claims description 46
• 150000002431 hydrogen Chemical class 0.000 claims description 46
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 45
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 43
• 238000011282 treatment Methods 0.000 claims description 41
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 40
• 125000002252 acyl group Chemical group 0.000 claims description 39
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 38
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 38
• 229910052736 halogen Inorganic materials 0.000 claims description 37
• 150000002367 halogens Chemical class 0.000 claims description 36
• 229910052760 oxygen Inorganic materials 0.000 claims description 31
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 30
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 27
• 125000006308 propyl amino group Chemical group 0.000 claims description 27
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 26
• 239000001301 oxygen Substances 0.000 claims description 26
• 239000012453 solvate Substances 0.000 claims description 26
• 229910052717 sulfur Chemical group 0.000 claims description 26
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 25
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
• 201000010099 disease Diseases 0.000 claims description 23
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 23
• 125000004432 carbon atom Chemical group C* 0.000 claims description 22
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 22
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 21
• 229910052799 carbon Inorganic materials 0.000 claims description 21
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 21
• 239000011593 sulfur Chemical group 0.000 claims description 21
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 20
• 125000004442 acylamino group Chemical group 0.000 claims description 19
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 19
• 125000004423 acyloxy group Chemical group 0.000 claims description 18
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 18
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 18
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 17
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 17
• 125000001424 substituent group Chemical group 0.000 claims description 17
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 17
• 206010022489 Insulin Resistance Diseases 0.000 claims description 16
• 208000029078 coronary artery disease Diseases 0.000 claims description 16
• 125000005842 heteroatom Chemical group 0.000 claims description 16
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• 208000008589 Obesity Diseases 0.000 claims description 15
• 125000001769 aryl amino group Chemical group 0.000 claims description 15
• 125000004104 aryloxy group Chemical group 0.000 claims description 15
• 235000012000 cholesterol Nutrition 0.000 claims description 15
• 235000020824 obesity Nutrition 0.000 claims description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical class NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 14
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 14
• 230000009467 reduction Effects 0.000 claims description 14
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 13
• 125000005843 halogen group Chemical group 0.000 claims description 13
• 239000003826 tablet Substances 0.000 claims description 13
• USOQPARFHFSEKW-UHFFFAOYSA-N 3-[4-[3-(2,3-dihydro-1,4-benzoxazin-4-yl)propylamino]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1NCCCN1C2=CC=CC=C2OCC1 USOQPARFHFSEKW-UHFFFAOYSA-N 0.000 claims description 12
• 206010020772 Hypertension Diseases 0.000 claims description 12
• 125000004414 alkyl thio group Chemical group 0.000 claims description 12
• 229910052749 magnesium Inorganic materials 0.000 claims description 12
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 11
• 229910019142 PO4 Inorganic materials 0.000 claims description 11
• 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 11
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 11
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 11
• 239000008103 glucose Substances 0.000 claims description 11
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 11
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
• 235000019260 propionic acid Nutrition 0.000 claims description 11
• 125000004001 thioalkyl group Chemical group 0.000 claims description 11
• HEOPYTCRWHVKAU-UHFFFAOYSA-N 2-ethoxy-3-[4-[3-(7-fluoro-2,3-dihydro-1,4-benzoxazin-4-yl)propylamino]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1NCCCN1C2=CC=C(F)C=C2OCC1 HEOPYTCRWHVKAU-UHFFFAOYSA-N 0.000 claims description 10
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 10
• 102000023984 PPAR alpha Human genes 0.000 claims description 10
• 150000001412 amines Chemical class 0.000 claims description 10
• 206010012601 diabetes mellitus Diseases 0.000 claims description 10
• 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 claims description 10
• 235000021317 phosphate Nutrition 0.000 claims description 10
• MWDVFNUAAJDISV-UHFFFAOYSA-N 2-ethoxy-3-[4-[3-(2-methyl-2,3-dihydro-1,4-benzoxazin-4-yl)propylamino]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1NCCCN1C2=CC=CC=C2OC(C)C1 MWDVFNUAAJDISV-UHFFFAOYSA-N 0.000 claims description 9
• DIWMNMYQDAADJN-UHFFFAOYSA-N 2-ethoxy-3-[4-[3-(2-propyl-2,3-dihydro-1,4-benzoxazin-4-yl)propylamino]phenyl]propanoic acid Chemical compound C12=CC=CC=C2OC(CCC)CN1CCCNC1=CC=C(CC(OCC)C(O)=O)C=C1 DIWMNMYQDAADJN-UHFFFAOYSA-N 0.000 claims description 9
• KLAQPSTUATZURY-UHFFFAOYSA-N 3-[3-[3-(2,3-dihydro-1,4-benzoxazin-4-yl)propylamino]phenyl]-2-ethoxypropanoic acid Chemical compound CCOC(C(O)=O)CC1=CC=CC(NCCCN2C3=CC=CC=C3OCC2)=C1 KLAQPSTUATZURY-UHFFFAOYSA-N 0.000 claims description 9
• MQSSCQLXCGLHDN-UHFFFAOYSA-N 3-[3-[[4-[3-(2,3-dihydro-1,4-benzoxazin-4-yl)propoxy]phenyl]methylamino]phenyl]-2-ethoxypropanoic acid Chemical compound CCOC(C(O)=O)CC1=CC=CC(NCC=2C=CC(OCCCN3C4=CC=CC=C4OCC3)=CC=2)=C1 MQSSCQLXCGLHDN-UHFFFAOYSA-N 0.000 claims description 9
• ANQOUCUQDRHFER-UHFFFAOYSA-N 3-[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethylamino]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1NCCN1C2=CC=CC=C2OCC1 ANQOUCUQDRHFER-UHFFFAOYSA-N 0.000 claims description 9
• IMIDIOAXEGOKFB-UHFFFAOYSA-N 3-[4-[3-(2,3-dihydro-1,4-benzothiazin-4-yl)propylamino]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1NCCCN1C2=CC=CC=C2SCC1 IMIDIOAXEGOKFB-UHFFFAOYSA-N 0.000 claims description 9
• DBMPMAATOJISLF-UHFFFAOYSA-N 3-[4-[3-(7-fluoro-2,3-dihydro-1,4-benzoxazin-4-yl)propylamino]phenyl]-2-propan-2-yloxypropanoic acid Chemical compound C1=CC(CC(OC(C)C)C(O)=O)=CC=C1NCCCN1C2=CC=C(F)C=C2OCC1 DBMPMAATOJISLF-UHFFFAOYSA-N 0.000 claims description 9
• VPZODFSHHVNOGX-UHFFFAOYSA-N 3-[4-[[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]anilino]methyl]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1CNC(C=C1)=CC=C1OCCN1C2=CC=CC=C2OCC1 VPZODFSHHVNOGX-UHFFFAOYSA-N 0.000 claims description 9
• ZGVMVYDMFCATHE-UHFFFAOYSA-N 3-[4-[[4-[3-(2,3-dihydro-1,4-benzoxazin-4-yl)propoxy]phenyl]methylamino]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1NCC(C=C1)=CC=C1OCCCN1C2=CC=CC=C2OCC1 ZGVMVYDMFCATHE-UHFFFAOYSA-N 0.000 claims description 9
• CGWKUCIPOZOWRZ-UHFFFAOYSA-N 3-[4-[[5-(2,3-dihydro-1,4-benzoxazin-4-yl)-5-oxopentyl]amino]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1NCCCCC(=O)N1C2=CC=CC=C2OCC1 CGWKUCIPOZOWRZ-UHFFFAOYSA-N 0.000 claims description 9
• 201000001320 Atherosclerosis Diseases 0.000 claims description 9
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 9
• 108010016731 PPAR gamma Proteins 0.000 claims description 9
• 229910052742 iron Inorganic materials 0.000 claims description 9
• DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 9
• 150000003626 triacylglycerols Chemical class 0.000 claims description 9
• SPXOTSHWBDUUMT-UHFFFAOYSA-N 138-42-1 Chemical compound OS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-N 0.000 claims description 8
• GYXAKDRNKCKVCV-UHFFFAOYSA-N 2-ethoxy-3-[4-[3-(7-fluoro-2-methyl-2,3-dihydro-1,4-benzoxazin-4-yl)propylamino]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1NCCCN1C2=CC=C(F)C=C2OC(C)C1 GYXAKDRNKCKVCV-UHFFFAOYSA-N 0.000 claims description 8
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 8
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 8
• 102000016267 Leptin Human genes 0.000 claims description 8
• 108010092277 Leptin Proteins 0.000 claims description 8
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Chemical class CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 8
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 8
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 8
• 235000001014 amino acid Nutrition 0.000 claims description 8
• 229940024606 amino acid Drugs 0.000 claims description 8
• 150000001413 amino acids Chemical class 0.000 claims description 8
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 8
• 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 8
• 239000003085 diluting agent Substances 0.000 claims description 8
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Chemical class CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 8
• IHDXFHXPXCQRJW-TUXUZCGSSA-N ethyl (2s)-2-methoxy-3-[4-[3-(2-propyl-2,3-dihydro-1,4-benzoxazin-4-yl)propylamino]phenyl]propanoate Chemical compound C12=CC=CC=C2OC(CCC)CN1CCCNC1=CC=C(C[C@H](OC)C(=O)OCC)C=C1 IHDXFHXPXCQRJW-TUXUZCGSSA-N 0.000 claims description 8
• BPWYOZLWMYOSIL-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[3-(2-methyl-2,3-dihydro-1,4-benzoxazin-4-yl)propylamino]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1NCCCN1C2=CC=CC=C2OC(C)C1 BPWYOZLWMYOSIL-UHFFFAOYSA-N 0.000 claims description 8
• JINPHZJFMFAKEH-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[3-(2-propyl-2,3-dihydro-1,4-benzoxazin-4-yl)propylamino]phenyl]propanoate Chemical compound C12=CC=CC=C2OC(CCC)CN1CCCNC1=CC=C(CC(OCC)C(=O)OCC)C=C1 JINPHZJFMFAKEH-UHFFFAOYSA-N 0.000 claims description 8
• UETSGEVVPSHQSY-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[3-(7-fluoro-2-methyl-2,3-dihydro-1,4-benzoxazin-4-yl)propylamino]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1NCCCN1C2=CC=C(F)C=C2OC(C)C1 UETSGEVVPSHQSY-UHFFFAOYSA-N 0.000 claims description 8
• FHOYOPVTNYGBPP-UHFFFAOYSA-N ethyl 3-[4-[3-(2,3-dihydro-1,4-benzothiazin-4-yl)propylamino]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1NCCCN1C2=CC=CC=C2SCC1 FHOYOPVTNYGBPP-UHFFFAOYSA-N 0.000 claims description 8
• PCKNUSDTLDALCQ-UHFFFAOYSA-N ethyl 3-[4-[3-(2,3-dihydro-1,4-benzoxazin-4-yl)propylamino]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1NCCCN1C2=CC=CC=C2OCC1 PCKNUSDTLDALCQ-UHFFFAOYSA-N 0.000 claims description 8
• NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 claims description 8
• 229940039781 leptin Drugs 0.000 claims description 8
• LVPINMGGBDXSKM-UHFFFAOYSA-N methyl 2-ethoxy-3-[4-[3-(7-fluoro-2,3-dihydro-1,4-benzoxazin-4-yl)propylamino]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OC)=CC=C1NCCCN1C2=CC=C(F)C=C2OCC1 LVPINMGGBDXSKM-UHFFFAOYSA-N 0.000 claims description 8
• HIPAXOJIVJVOPK-UHFFFAOYSA-N methyl 3-[3-[3-(2,3-dihydro-1,4-benzoxazin-4-yl)propylamino]phenyl]-2-ethoxypropanoate Chemical compound CCOC(C(=O)OC)CC1=CC=CC(NCCCN2C3=CC=CC=C3OCC2)=C1 HIPAXOJIVJVOPK-UHFFFAOYSA-N 0.000 claims description 8
• LZNZCSYTSGRKEL-UHFFFAOYSA-N methyl 3-[4-[[5-(2,3-dihydro-1,4-benzoxazin-4-yl)-5-oxopentyl]amino]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(CC(OCC)C(=O)OC)=CC=C1NCCCCC(=O)N1C2=CC=CC=C2OCC1 LZNZCSYTSGRKEL-UHFFFAOYSA-N 0.000 claims description 8
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 8
• 239000010452 phosphate Substances 0.000 claims description 8
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 8
• 208000035150 Hypercholesterolemia Diseases 0.000 claims description 7
• 125000003282 alkyl amino group Chemical group 0.000 claims description 7
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 7
• 230000037396 body weight Effects 0.000 claims description 7
• GBLFUEDQJPMCPK-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[3-(7-fluoro-2,3-dihydro-1,4-benzoxazin-4-yl)propylamino]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1NCCCN1C2=CC=C(F)C=C2OCC1 GBLFUEDQJPMCPK-UHFFFAOYSA-N 0.000 claims description 7
• GKJJJMYAWFAXBE-UHFFFAOYSA-N ethyl 3-[4-[3-(7-fluoro-2,3-dihydro-1,4-benzoxazin-4-yl)propylamino]phenyl]-2-methoxypropanoate Chemical compound C1=CC(CC(C(=O)OCC)OC)=CC=C1NCCCN1C2=CC=C(F)C=C2OCC1 GKJJJMYAWFAXBE-UHFFFAOYSA-N 0.000 claims description 7
• GCQSGPBDMUETQD-UHFFFAOYSA-N ethyl 3-[4-[3-(7-fluoro-2,3-dihydro-1,4-benzoxazin-4-yl)propylamino]phenyl]-2-propan-2-yloxypropanoate Chemical compound C1=CC(CC(C(=O)OCC)OC(C)C)=CC=C1NCCCN1C2=CC=C(F)C=C2OCC1 GCQSGPBDMUETQD-UHFFFAOYSA-N 0.000 claims description 7
• 125000004043 oxo group Chemical group O=* 0.000 claims description 7
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
• 208000011580 syndromic disease Diseases 0.000 claims description 7
• 125000000464 thioxo group Chemical group S=* 0.000 claims description 7
• BZTKVNVOWUZRSH-UHFFFAOYSA-N 2-methoxy-3-[4-[3-(2-methyl-2,3-dihydro-1,4-benzoxazin-4-yl)propylamino]phenyl]propanoic acid Chemical compound C1=CC(CC(OC)C(O)=O)=CC=C1NCCCN1C2=CC=CC=C2OC(C)C1 BZTKVNVOWUZRSH-UHFFFAOYSA-N 0.000 claims description 6
• WFFHMUNWZQTZNQ-UHFFFAOYSA-N 2-methoxy-3-[4-[3-(2-propyl-2,3-dihydro-1,4-benzoxazin-4-yl)propylamino]phenyl]propanoic acid Chemical compound C12=CC=CC=C2OC(CCC)CN1CCCNC1=CC=C(CC(OC)C(O)=O)C=C1 WFFHMUNWZQTZNQ-UHFFFAOYSA-N 0.000 claims description 6
• VOINQATVKVAIOW-UHFFFAOYSA-N 3-[4-[3-(7-fluoro-2,3-dihydro-1,4-benzoxazin-4-yl)propylamino]phenyl]-2-methoxypropanoic acid Chemical compound C1=CC(CC(OC)C(O)=O)=CC=C1NCCCN1C2=CC=C(F)C=C2OCC1 VOINQATVKVAIOW-UHFFFAOYSA-N 0.000 claims description 6
• COAKHMNIDAXALI-UHFFFAOYSA-N 3-[4-[3-(7-fluoro-2-methyl-2,3-dihydro-1,4-benzoxazin-4-yl)propylamino]phenyl]-2-methoxypropanoic acid Chemical compound C1=CC(CC(OC)C(O)=O)=CC=C1NCCCN1C2=CC=C(F)C=C2OC(C)C1 COAKHMNIDAXALI-UHFFFAOYSA-N 0.000 claims description 6
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 6
• 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims description 6
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