JP2002527503A - 新規化合物類、それらの調製及び使用 - Google Patents
新規化合物類、それらの調製及び使用Info
- Publication number
- JP2002527503A JP2002527503A JP2000577145A JP2000577145A JP2002527503A JP 2002527503 A JP2002527503 A JP 2002527503A JP 2000577145 A JP2000577145 A JP 2000577145A JP 2000577145 A JP2000577145 A JP 2000577145A JP 2002527503 A JP2002527503 A JP 2002527503A
- Authority
- JP
- Japan
- Prior art keywords
- ethoxy
- phenyl
- cyclohepten
- dibenzo
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 201
- 238000002360 preparation method Methods 0.000 title claims description 9
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims abstract description 20
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims abstract description 19
- 230000001404 mediated effect Effects 0.000 claims abstract description 7
- 108020005497 Nuclear hormone receptor Proteins 0.000 claims abstract description 5
- 102000006255 nuclear receptors Human genes 0.000 claims abstract description 5
- 108020004017 nuclear receptors Proteins 0.000 claims abstract description 5
- -1 cyano, formyl Chemical group 0.000 claims description 1018
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 288
- 125000000217 alkyl group Chemical group 0.000 claims description 128
- 241001024304 Mino Species 0.000 claims description 116
- 239000002253 acid Substances 0.000 claims description 112
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 84
- 229910052736 halogen Inorganic materials 0.000 claims description 74
- 150000002367 halogens Chemical class 0.000 claims description 74
- 239000001257 hydrogen Substances 0.000 claims description 69
- 229910052739 hydrogen Inorganic materials 0.000 claims description 69
- 125000003118 aryl group Chemical group 0.000 claims description 66
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 62
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 58
- 125000004104 aryloxy group Chemical group 0.000 claims description 52
- 150000002431 hydrogen Chemical class 0.000 claims description 51
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 34
- 125000000623 heterocyclic group Chemical group 0.000 claims description 32
- 125000002252 acyl group Chemical group 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 26
- 125000004494 ethyl ester group Chemical group 0.000 claims description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- 125000001769 aryl amino group Chemical group 0.000 claims description 22
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 20
- 125000000304 alkynyl group Chemical group 0.000 claims description 19
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 19
- 235000019260 propionic acid Nutrition 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 125000004442 acylamino group Chemical group 0.000 claims description 18
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 15
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 208000008589 Obesity Diseases 0.000 claims description 9
- 125000004423 acyloxy group Chemical group 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 9
- 235000020824 obesity Nutrition 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 206010012601 diabetes mellitus Diseases 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 5
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
- UUHJLWSFWXMQBR-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-[methyl-(3-phenyl-8-propyl-6,11-dihydro-5h-dibenzo[1,3-a:1',3'-e][7]annulen-11-yl)amino]ethoxy]phenyl]propanoic acid Chemical compound C12=CC=C(C=3C=CC=CC=3)C=C2CCC2=CC(CCC)=CC=C2C1N(C)CCOC1=CC=C(CC(OCC)C(O)=O)C=C1 UUHJLWSFWXMQBR-UHFFFAOYSA-N 0.000 claims description 4
- SKIKODKCSNWOPH-UHFFFAOYSA-N 2-methoxy-3-[4-[2-[methyl-(3-phenyl-8-propyl-6,11-dihydro-5h-dibenzo[1,3-a:1',3'-e][7]annulen-11-yl)amino]ethoxy]phenyl]propanoic acid Chemical compound C12=CC=C(C=3C=CC=CC=3)C=C2CCC2=CC(CCC)=CC=C2C1N(C)CCOC1=CC=C(CC(OC)C(O)=O)C=C1 SKIKODKCSNWOPH-UHFFFAOYSA-N 0.000 claims description 4
- LHPWQCOZYWLQII-UHFFFAOYSA-N 3-[4-[2-[(3-benzyl-8-propyl-6,11-dihydro-5h-dibenzo[1,3-a:1',3'-e][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C12=CC=C(CC=3C=CC=CC=3)C=C2CCC2=CC(CCC)=CC=C2C1N(C)CCOC1=CC=C(CC(OCC)C(O)=O)C=C1 LHPWQCOZYWLQII-UHFFFAOYSA-N 0.000 claims description 4
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 4
- LARUQGVTIYCNGG-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[methyl-(3-phenyl-8-propyl-6,11-dihydro-5h-dibenzo[1,3-a:1',3'-e][7]annulen-11-yl)amino]ethoxy]phenyl]propanoate Chemical compound C12=CC=C(C=3C=CC=CC=3)C=C2CCC2=CC(CCC)=CC=C2C1N(C)CCOC1=CC=C(CC(OCC)C(=O)OCC)C=C1 LARUQGVTIYCNGG-UHFFFAOYSA-N 0.000 claims description 4
- DZOLWTGFVSSEAD-UHFFFAOYSA-N ethyl 2-methoxy-3-[4-[2-[methyl-(3-phenyl-8-propyl-6,11-dihydro-5h-dibenzo[1,3-a:1',3'-e][7]annulen-11-yl)amino]ethoxy]phenyl]propanoate Chemical compound C12=CC=C(C=3C=CC=CC=3)C=C2CCC2=CC(CCC)=CC=C2C1N(C)CCOC1=CC=C(CC(OC)C(=O)OCC)C=C1 DZOLWTGFVSSEAD-UHFFFAOYSA-N 0.000 claims description 4
- 230000002685 pulmonary effect Effects 0.000 claims description 4
- SLAVQTUJAOFOCR-UHFFFAOYSA-N 3-[4-[2-(6,11-dihydro-5h-dibenzo[1,2-a:1',2'-e][7]annulen-11-yloxy)ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCOC1C2=CC=CC=C2CCC2=CC=CC=C21 SLAVQTUJAOFOCR-UHFFFAOYSA-N 0.000 claims description 3
- ZBAZSQZPEARCOP-UHFFFAOYSA-N 3-[4-[2-(6,11-dihydrobenzo[c][1]benzoxepin-11-ylsulfanyl)ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCSC1C2=CC=CC=C2OCC2=CC=CC=C21 ZBAZSQZPEARCOP-UHFFFAOYSA-N 0.000 claims description 3
- VMHIXYHOYMHIHS-UHFFFAOYSA-N 3-[4-[2-[(3-benzyl-8-propyl-6,11-dihydro-5h-dibenzo[1,3-a:1',3'-e][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-methoxypropanoic acid Chemical compound C12=CC=C(CC=3C=CC=CC=3)C=C2CCC2=CC(CCC)=CC=C2C1N(C)CCOC1=CC=C(CC(OC)C(O)=O)C=C1 VMHIXYHOYMHIHS-UHFFFAOYSA-N 0.000 claims description 3
- 208000017667 Chronic Disease Diseases 0.000 claims description 3
- 125000005038 alkynylalkyl group Chemical group 0.000 claims description 3
- WTHJKWQVWFZMJU-UHFFFAOYSA-N ethyl 3-[4-[2-[(3-benzyl-8-propyl-6,11-dihydro-5h-dibenzo[1,3-a:1',3'-e][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-ethoxypropanoate Chemical compound C12=CC=C(CC=3C=CC=CC=3)C=C2CCC2=CC(CCC)=CC=C2C1N(C)CCOC1=CC=C(CC(OCC)C(=O)OCC)C=C1 WTHJKWQVWFZMJU-UHFFFAOYSA-N 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- XFQSTNWIVSPDBO-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-[(5-methyl-6-oxo-11h-benzo[c][1]benzazepin-11-yl)oxy]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCOC1C2=CC=CC=C2C(=O)N(C)C2=CC=CC=C21 XFQSTNWIVSPDBO-UHFFFAOYSA-N 0.000 claims description 2
- CQCMYWURFOBPLC-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-[methyl-(2-phenyl-6,11-dihydro-5h-dibenzo[1,3-e:1',2'-f][7]annulen-11-yl)amino]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN(C)C1C2=CC(C=3C=CC=CC=3)=CC=C2CCC2=CC=CC=C21 CQCMYWURFOBPLC-UHFFFAOYSA-N 0.000 claims description 2
- YEMUJQIEZDZDGV-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-[methyl-(3-phenyl-6,11-dihydro-5h-dibenzo[1,2-a:1',3'-e][7]annulen-11-yl)amino]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN(C)C1C2=CC=C(C=3C=CC=CC=3)C=C2CCC2=CC=CC=C21 YEMUJQIEZDZDGV-UHFFFAOYSA-N 0.000 claims description 2
- OYZHJGVKAAAICK-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-[methyl-(3-phenyl-9-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl)amino]ethoxy]phenyl]propanoic acid Chemical compound C12=CC(CCC)=CC=C2CCC2=CC(C=3C=CC=CC=3)=CC=C2C1N(C)CCOC1=CC=C(CC(OCC)C(O)=O)C=C1 OYZHJGVKAAAICK-UHFFFAOYSA-N 0.000 claims description 2
- LBPBGICYDANAMK-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-[methyl-(9-phenyl-3-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl)amino]ethoxy]phenyl]propanoic acid Chemical compound C12=CC(C=3C=CC=CC=3)=CC=C2CCC2=CC(CCC)=CC=C2C1N(C)CCOC1=CC=C(CC(OCC)C(O)=O)C=C1 LBPBGICYDANAMK-UHFFFAOYSA-N 0.000 claims description 2
- NVLGUMDSZVTAKW-UHFFFAOYSA-N 2-methoxy-3-[4-[2-[methyl-(2-phenyl-6,11-dihydro-5h-dibenzo[1,3-e:1',2'-f][7]annulen-11-yl)amino]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OC)C(O)=O)=CC=C1OCCN(C)C1C2=CC(C=3C=CC=CC=3)=CC=C2CCC2=CC=CC=C21 NVLGUMDSZVTAKW-UHFFFAOYSA-N 0.000 claims description 2
- IUYZALOQZCSRFJ-UHFFFAOYSA-N 2-methoxy-3-[4-[2-[methyl-(2-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',2'-f][7]annulen-11-yl)amino]ethoxy]phenyl]propanoic acid Chemical compound C12=CC(CCC)=CC=C2CCC2=CC=CC=C2C1N(C)CCOC1=CC=C(CC(OC)C(O)=O)C=C1 IUYZALOQZCSRFJ-UHFFFAOYSA-N 0.000 claims description 2
- STQZRDCXYHHFBM-UHFFFAOYSA-N 2-methoxy-3-[4-[2-[methyl-(3-phenyl-6,11-dihydro-5h-dibenzo[1,2-a:1',3'-e][7]annulen-11-yl)amino]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OC)C(O)=O)=CC=C1OCCN(C)C1C2=CC=C(C=3C=CC=CC=3)C=C2CCC2=CC=CC=C21 STQZRDCXYHHFBM-UHFFFAOYSA-N 0.000 claims description 2
- OFDXVKQPYJNOLP-UHFFFAOYSA-N 2-methoxy-3-[4-[2-[methyl-(3-phenyl-9-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl)amino]ethoxy]phenyl]propanoic acid Chemical compound C12=CC(CCC)=CC=C2CCC2=CC(C=3C=CC=CC=3)=CC=C2C1N(C)CCOC1=CC=C(CC(OC)C(O)=O)C=C1 OFDXVKQPYJNOLP-UHFFFAOYSA-N 0.000 claims description 2
- BJHMYUZHXPAAAZ-UHFFFAOYSA-N 2-methoxy-3-[4-[2-[methyl-(9-phenyl-3-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl)amino]ethoxy]phenyl]propanoic acid Chemical compound C12=CC(C=3C=CC=CC=3)=CC=C2CCC2=CC(CCC)=CC=C2C1N(C)CCOC1=CC=C(CC(OC)C(O)=O)C=C1 BJHMYUZHXPAAAZ-UHFFFAOYSA-N 0.000 claims description 2
- CXEKPRGUENDJAK-UHFFFAOYSA-N 2-methoxy-3-[4-[2-[methyl-[2-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,3-e:1',2'-f][7]annulen-11-yl]amino]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OC)C(O)=O)=CC=C1OCCN(C)C1C2=CC(CCC=3C=CC=CC=3)=CC=C2CCC2=CC=CC=C21 CXEKPRGUENDJAK-UHFFFAOYSA-N 0.000 claims description 2
- QFLRQYUBWUNUOG-UHFFFAOYSA-N 3-[4-[2-[(2-benzyl-6,11-dihydro-5h-dibenzo[1,3-e:1',2'-f][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN(C)C1C2=CC(CC=3C=CC=CC=3)=CC=C2CCC2=CC=CC=C21 QFLRQYUBWUNUOG-UHFFFAOYSA-N 0.000 claims description 2
- AHASRLVRXQRSFZ-UHFFFAOYSA-N 3-[4-[2-[(2-benzyl-6,11-dihydro-5h-dibenzo[1,3-e:1',2'-f][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-methoxypropanoic acid Chemical compound C1=CC(CC(OC)C(O)=O)=CC=C1OCCN(C)C1C2=CC(CC=3C=CC=CC=3)=CC=C2CCC2=CC=CC=C21 AHASRLVRXQRSFZ-UHFFFAOYSA-N 0.000 claims description 2
- LLRBEBCQRCOBDE-UHFFFAOYSA-N 3-[4-[2-[(3-benzyl-6,11-dihydro-5h-dibenzo[1,2-a:1',3'-e][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN(C)C1C2=CC=C(CC=3C=CC=CC=3)C=C2CCC2=CC=CC=C21 LLRBEBCQRCOBDE-UHFFFAOYSA-N 0.000 claims description 2
- NRWPFFVGLUIJOQ-UHFFFAOYSA-N 3-[4-[2-[(3-benzyl-6,11-dihydro-5h-dibenzo[1,2-a:1',3'-e][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-methoxypropanoic acid Chemical compound C1=CC(CC(OC)C(O)=O)=CC=C1OCCN(C)C1C2=CC=C(CC=3C=CC=CC=3)C=C2CCC2=CC=CC=C21 NRWPFFVGLUIJOQ-UHFFFAOYSA-N 0.000 claims description 2
- JLQZYGIFPCSPPS-UHFFFAOYSA-N 3-[4-[2-[(9-benzyl-3-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C12=CC(CC=3C=CC=CC=3)=CC=C2CCC2=CC(CCC)=CC=C2C1N(C)CCOC1=CC=C(CC(OCC)C(O)=O)C=C1 JLQZYGIFPCSPPS-UHFFFAOYSA-N 0.000 claims description 2
- BICYSBWXEMTWKV-UHFFFAOYSA-N 3-[4-[2-[(9-benzyl-3-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-methoxypropanoic acid Chemical compound C12=CC(CC=3C=CC=CC=3)=CC=C2CCC2=CC(CCC)=CC=C2C1N(C)CCOC1=CC=C(CC(OC)C(O)=O)C=C1 BICYSBWXEMTWKV-UHFFFAOYSA-N 0.000 claims description 2
- YXUKYZQBPFMUTF-UHFFFAOYSA-N 3-[4-[2-[6,11-dihydro-5h-dibenzo[1,2-a:1',2'-e][7]annulen-11-yl(methyl)amino]ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN(C)C1C2=CC=CC=C2CCC2=CC=CC=C21 YXUKYZQBPFMUTF-UHFFFAOYSA-N 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- FKIAMAZMGOHICC-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[methyl-(3-phenyl-9-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl)amino]ethoxy]phenyl]propanoate Chemical compound C12=CC(CCC)=CC=C2CCC2=CC(C=3C=CC=CC=3)=CC=C2C1N(C)CCOC1=CC=C(CC(OCC)C(=O)OCC)C=C1 FKIAMAZMGOHICC-UHFFFAOYSA-N 0.000 claims description 2
- LSUXNLHWTTZKPU-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[methyl-(9-phenyl-3-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl)amino]ethoxy]phenyl]propanoate Chemical compound C12=CC(C=3C=CC=CC=3)=CC=C2CCC2=CC(CCC)=CC=C2C1N(C)CCOC1=CC=C(CC(OCC)C(=O)OCC)C=C1 LSUXNLHWTTZKPU-UHFFFAOYSA-N 0.000 claims description 2
- MCGKNKTYRCWVBU-UHFFFAOYSA-N ethyl 2-methoxy-3-[4-[2-[methyl-(3-phenyl-9-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl)amino]ethoxy]phenyl]propanoate Chemical compound C12=CC(CCC)=CC=C2CCC2=CC(C=3C=CC=CC=3)=CC=C2C1N(C)CCOC1=CC=C(CC(OC)C(=O)OCC)C=C1 MCGKNKTYRCWVBU-UHFFFAOYSA-N 0.000 claims description 2
- YAPSQCMOLHOGHK-UHFFFAOYSA-N ethyl 2-methoxy-3-[4-[2-[methyl-(9-phenyl-3-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl)amino]ethoxy]phenyl]propanoate Chemical compound C12=CC(C=3C=CC=CC=3)=CC=C2CCC2=CC(CCC)=CC=C2C1N(C)CCOC1=CC=C(CC(OC)C(=O)OCC)C=C1 YAPSQCMOLHOGHK-UHFFFAOYSA-N 0.000 claims description 2
- OHRQBIUDEUQWMT-UHFFFAOYSA-N ethyl 3-[4-[2-[(2-benzyl-6,11-dihydro-5h-dibenzo[1,3-e:1',2'-f][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-methoxypropanoate Chemical compound C1=CC(CC(C(=O)OCC)OC)=CC=C1OCCN(C)C1C2=CC(CC=3C=CC=CC=3)=CC=C2CCC2=CC=CC=C21 OHRQBIUDEUQWMT-UHFFFAOYSA-N 0.000 claims description 2
- FVWYYBQUOPKRKV-UHFFFAOYSA-N ethyl 3-[4-[2-[(3-benzyl-6,11-dihydro-5h-dibenzo[1,2-a:1',3'-e][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-methoxypropanoate Chemical compound C1=CC(CC(C(=O)OCC)OC)=CC=C1OCCN(C)C1C2=CC=C(CC=3C=CC=CC=3)C=C2CCC2=CC=CC=C21 FVWYYBQUOPKRKV-UHFFFAOYSA-N 0.000 claims description 2
- NDQVFMKWLGRJLQ-UHFFFAOYSA-N ethyl 3-[4-[2-[(9-benzyl-3-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-ethoxypropanoate Chemical compound C12=CC(CC=3C=CC=CC=3)=CC=C2CCC2=CC(CCC)=CC=C2C1N(C)CCOC1=CC=C(CC(OCC)C(=O)OCC)C=C1 NDQVFMKWLGRJLQ-UHFFFAOYSA-N 0.000 claims description 2
- HHIROLPTLJHIAC-UHFFFAOYSA-N ethyl 3-[4-[2-[(9-benzyl-3-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-methoxypropanoate Chemical compound C12=CC(CC=3C=CC=CC=3)=CC=C2CCC2=CC(CCC)=CC=C2C1N(C)CCOC1=CC=C(CC(OC)C(=O)OCC)C=C1 HHIROLPTLJHIAC-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 238000007911 parenteral administration Methods 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
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- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000005979 2-naphthyloxy group Chemical group 0.000 description 1
- 125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 description 1
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- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- LQHNZFGFVMOGEU-UHFFFAOYSA-N 3-(5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-ylidene)propyl methanesulfonate Chemical compound C1CC2=CC=CC=C2C(=CCCOS(=O)(=O)C)C2=CC=CC=C21 LQHNZFGFVMOGEU-UHFFFAOYSA-N 0.000 description 1
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- ZXGDJKAFUIWWRU-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[(2-methyl-5,10-dihydro-4h-benzo[1,2]cyclohepta[3,4-c][1,3]oxazol-10-yl)oxy]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCOC1C2=CC=CC=C2CCC2=C1N=C(C)O2 ZXGDJKAFUIWWRU-UHFFFAOYSA-N 0.000 description 1
- RYXQWAPXCULYMP-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[(3-ethyl-9-phenyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl)-methylamino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN(C)C1C2=CC(C=3C=CC=CC=3)=CC=C2CCC2=CC(CC)=CC=C21 RYXQWAPXCULYMP-UHFFFAOYSA-N 0.000 description 1
- STJWWWWDFIYLIZ-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[(3-ethyl-9-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl)-methylamino]ethoxy]phenyl]propanoate Chemical compound C12=CC(CCC)=CC=C2CCC2=CC(CC)=CC=C2C1N(C)CCOC1=CC=C(CC(OCC)C(=O)OCC)C=C1 STJWWWWDFIYLIZ-UHFFFAOYSA-N 0.000 description 1
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- FPSBPIZUWQRTQM-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[(9-ethyl-3-methyl-6,11-dihydro-5h-dibenzo[1,3-e:1',2'-f][7]annulen-11-yl)-methylamino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN(C)C1C2=CC(CC)=CC=C2CCC2=CC(C)=CC=C21 FPSBPIZUWQRTQM-UHFFFAOYSA-N 0.000 description 1
- KVROLQYGTGNNCA-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[(9-ethyl-3-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl)-methylamino]ethoxy]phenyl]propanoate Chemical compound C12=CC(CC)=CC=C2CCC2=CC(CCC)=CC=C2C1N(C)CCOC1=CC=C(CC(OCC)C(=O)OCC)C=C1 KVROLQYGTGNNCA-UHFFFAOYSA-N 0.000 description 1
- KAZWQZPLCVGNJW-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[[2-ethyl-7-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl]-methylamino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN(C)C1C2=CC(CC)=CC=C2CCC2=C(CCC=3C=CC=CC=3)C=CC=C21 KAZWQZPLCVGNJW-UHFFFAOYSA-N 0.000 description 1
- JWTCJACWHOYNFU-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[[3-ethyl-7-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl]-methylamino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN(C)C1C2=CC=CC(CCC=3C=CC=CC=3)=C2CCC2=CC(CC)=CC=C21 JWTCJACWHOYNFU-UHFFFAOYSA-N 0.000 description 1
- UAVJKIAOXWZNKP-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[[3-ethyl-9-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl]-methylamino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN(C)C1C2=CC(CCC=3C=CC=CC=3)=CC=C2CCC2=CC(CC)=CC=C21 UAVJKIAOXWZNKP-UHFFFAOYSA-N 0.000 description 1
- MDHYHTMRSIIYLW-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[[8-ethyl-3-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,3-a:1',3'-e][7]annulen-11-yl]-methylamino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN(C)C1C2=CC=C(CCC=3C=CC=CC=3)C=C2CCC2=CC(CC)=CC=C21 MDHYHTMRSIIYLW-UHFFFAOYSA-N 0.000 description 1
- OUADRVQKYSTBPQ-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[methyl-(3-methyl-9-phenyl-6,11-dihydro-5h-dibenzo[1,3-e:1',2'-f][7]annulen-11-yl)amino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN(C)C1C2=CC(C=3C=CC=CC=3)=CC=C2CCC2=CC(C)=CC=C21 OUADRVQKYSTBPQ-UHFFFAOYSA-N 0.000 description 1
- JNIAVIAAMLYBPN-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[methyl-(3-methyl-9-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',2'-f][7]annulen-11-yl)amino]ethoxy]phenyl]propanoate Chemical compound C12=CC(CCC)=CC=C2CCC2=CC(C)=CC=C2C1N(C)CCOC1=CC=C(CC(OCC)C(=O)OCC)C=C1 JNIAVIAAMLYBPN-UHFFFAOYSA-N 0.000 description 1
- VQTZJHOUVVERQN-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[methyl-(8-methyl-3-phenyl-6,11-dihydro-5h-dibenzo[1,2-a:1',3'-e][7]annulen-11-yl)amino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN(C)C1C2=CC=C(C=3C=CC=CC=3)C=C2CCC2=CC(C)=CC=C21 VQTZJHOUVVERQN-UHFFFAOYSA-N 0.000 description 1
- ZDRXBMRRPIPBTQ-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[methyl-(8-methyl-3-propyl-6,11-dihydro-5h-dibenzo[1,2-a:1',3'-e][7]annulen-11-yl)amino]ethoxy]phenyl]propanoate Chemical compound C12=CC=C(C)C=C2CCC2=CC(CCC)=CC=C2C1N(C)CCOC1=CC=C(CC(OCC)C(=O)OCC)C=C1 ZDRXBMRRPIPBTQ-UHFFFAOYSA-N 0.000 description 1
- IHFNHAHICLXBNV-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[methyl-(9-methyl-3-propyl-6,11-dihydro-5h-dibenzo[1,2-e:1',3'-f][7]annulen-11-yl)amino]ethoxy]phenyl]propanoate Chemical compound C12=CC(C)=CC=C2CCC2=CC(CCC)=CC=C2C1N(C)CCOC1=CC=C(CC(OCC)C(=O)OCC)C=C1 IHFNHAHICLXBNV-UHFFFAOYSA-N 0.000 description 1
- YIHLGXGGLVLTSF-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[methyl-[2-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,3-e:1',2'-f][7]annulen-11-yl]amino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN(C)C1C2=CC(CCC=3C=CC=CC=3)=CC=C2CCC2=CC=CC=C21 YIHLGXGGLVLTSF-UHFFFAOYSA-N 0.000 description 1
- RKDXFBZOJLBLQT-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[methyl-[2-methyl-7-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,2-e:1',3'-f][7]annulen-11-yl]amino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN(C)C1C2=CC(C)=CC=C2CCC2=C(CCC=3C=CC=CC=3)C=CC=C21 RKDXFBZOJLBLQT-UHFFFAOYSA-N 0.000 description 1
- PCLAXAFZXUYDGJ-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[methyl-[3-methyl-7-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,2-e:1',3'-f][7]annulen-11-yl]amino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN(C)C1C2=CC=CC(CCC=3C=CC=CC=3)=C2CCC2=CC(C)=CC=C21 PCLAXAFZXUYDGJ-UHFFFAOYSA-N 0.000 description 1
- VMRVZHMJTYZTMZ-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[methyl-[3-methyl-9-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,3-e:1',2'-f][7]annulen-11-yl]amino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN(C)C1C2=CC(CCC=3C=CC=CC=3)=CC=C2CCC2=CC(C)=CC=C21 VMRVZHMJTYZTMZ-UHFFFAOYSA-N 0.000 description 1
- BWOGVRALBFMVTP-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[methyl-[3-phenyl-8-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,3-a:1',3'-e][7]annulen-11-yl]amino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN(C)C1C2=CC=C(C=3C=CC=CC=3)C=C2CCC2=CC(CCC=3C=CC=CC=3)=CC=C21 BWOGVRALBFMVTP-UHFFFAOYSA-N 0.000 description 1
- KBSAHKNIOFPTOQ-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[methyl-[3-phenyl-9-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl]amino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN(C)C1C2=CC(CCC=3C=CC=CC=3)=CC=C2CCC2=CC(C=3C=CC=CC=3)=CC=C21 KBSAHKNIOFPTOQ-UHFFFAOYSA-N 0.000 description 1
- YRCPVRCWGJKIPR-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[methyl-[4-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,2-a:1',3'-e][7]annulen-11-yl]amino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN(C)C1C2=CC=CC(CCC=3C=CC=CC=3)=C2CCC2=CC=CC=C21 YRCPVRCWGJKIPR-UHFFFAOYSA-N 0.000 description 1
- JJXYVZATTMGQJV-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[methyl-[7-(2-phenylethyl)-2-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl]amino]ethoxy]phenyl]propanoate Chemical compound C1=CC=C2C(N(C)CCOC=3C=CC(CC(OCC)C(=O)OCC)=CC=3)C3=CC(CCC)=CC=C3CCC2=C1CCC1=CC=CC=C1 JJXYVZATTMGQJV-UHFFFAOYSA-N 0.000 description 1
- SQDDVYLQGVQUAY-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[methyl-[7-(2-phenylethyl)-3-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl]amino]ethoxy]phenyl]propanoate Chemical compound C12=CC=CC(CCC=3C=CC=CC=3)=C2CCC2=CC(CCC)=CC=C2C1N(C)CCOC1=CC=C(CC(OCC)C(=O)OCC)C=C1 SQDDVYLQGVQUAY-UHFFFAOYSA-N 0.000 description 1
- ONLCEKRFHVGNSH-UHFFFAOYSA-N ethyl 2-ethoxy-3-[4-[2-[methyl-[8-methyl-3-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,2-a:1',3'-e][7]annulen-11-yl]amino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN(C)C1C2=CC=C(CCC=3C=CC=CC=3)C=C2CCC2=CC(C)=CC=C21 ONLCEKRFHVGNSH-UHFFFAOYSA-N 0.000 description 1
- OEEXFFRDIHKMNK-UHFFFAOYSA-N ethyl 2-methoxy-3-[4-[2-[methyl-(3-methyl-9-phenyl-6,11-dihydro-5h-dibenzo[1,3-e:1',2'-f][7]annulen-11-yl)amino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(C(=O)OCC)OC)=CC=C1OCCN(C)C1C2=CC(C=3C=CC=CC=3)=CC=C2CCC2=CC(C)=CC=C21 OEEXFFRDIHKMNK-UHFFFAOYSA-N 0.000 description 1
- CMYHRGIBSMTLIU-UHFFFAOYSA-N ethyl 2-methoxy-3-[4-[2-[methyl-(3-methyl-9-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',2'-f][7]annulen-11-yl)amino]ethoxy]phenyl]propanoate Chemical compound C12=CC(CCC)=CC=C2CCC2=CC(C)=CC=C2C1N(C)CCOC1=CC=C(CC(OC)C(=O)OCC)C=C1 CMYHRGIBSMTLIU-UHFFFAOYSA-N 0.000 description 1
- TUGXWMZGPUDQJE-UHFFFAOYSA-N ethyl 2-methoxy-3-[4-[2-[methyl-(8-methyl-3-phenyl-6,11-dihydro-5h-dibenzo[1,2-a:1',3'-e][7]annulen-11-yl)amino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(C(=O)OCC)OC)=CC=C1OCCN(C)C1C2=CC=C(C=3C=CC=CC=3)C=C2CCC2=CC(C)=CC=C21 TUGXWMZGPUDQJE-UHFFFAOYSA-N 0.000 description 1
- DWSKVLQTBRCNMO-UHFFFAOYSA-N ethyl 2-methoxy-3-[4-[2-[methyl-(9-methyl-3-propyl-6,11-dihydro-5h-dibenzo[1,2-e:1',3'-f][7]annulen-11-yl)amino]ethoxy]phenyl]propanoate Chemical compound C12=CC(C)=CC=C2CCC2=CC(CCC)=CC=C2C1N(C)CCOC1=CC=C(CC(OC)C(=O)OCC)C=C1 DWSKVLQTBRCNMO-UHFFFAOYSA-N 0.000 description 1
- ZRJXDKFEFYGCKB-UHFFFAOYSA-N ethyl 2-methoxy-3-[4-[2-[methyl-[2-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,3-e:1',2'-f][7]annulen-11-yl]amino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(C(=O)OCC)OC)=CC=C1OCCN(C)C1C2=CC(CCC=3C=CC=CC=3)=CC=C2CCC2=CC=CC=C21 ZRJXDKFEFYGCKB-UHFFFAOYSA-N 0.000 description 1
- GIMIFXUFHSUSLD-UHFFFAOYSA-N ethyl 2-methoxy-3-[4-[2-[methyl-[2-methyl-7-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,2-e:1',3'-f][7]annulen-11-yl]amino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(C(=O)OCC)OC)=CC=C1OCCN(C)C1C2=CC=CC(CCC=3C=CC=CC=3)=C2CCC2=CC=C(C)C=C21 GIMIFXUFHSUSLD-UHFFFAOYSA-N 0.000 description 1
- WAGZIHPGGUXHCL-UHFFFAOYSA-N ethyl 2-methoxy-3-[4-[2-[methyl-[3-methyl-7-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,2-e:1',3'-f][7]annulen-11-yl]amino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(C(=O)OCC)OC)=CC=C1OCCN(C)C1C2=CC=CC(CCC=3C=CC=CC=3)=C2CCC2=CC(C)=CC=C21 WAGZIHPGGUXHCL-UHFFFAOYSA-N 0.000 description 1
- KEMBLTBTTHPXGE-UHFFFAOYSA-N ethyl 2-methoxy-3-[4-[2-[methyl-[3-methyl-9-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,3-e:1',2'-f][7]annulen-11-yl]amino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(C(=O)OCC)OC)=CC=C1OCCN(C)C1C2=CC(CCC=3C=CC=CC=3)=CC=C2CCC2=CC(C)=CC=C21 KEMBLTBTTHPXGE-UHFFFAOYSA-N 0.000 description 1
- JNKGXOQFWWYMDL-UHFFFAOYSA-N ethyl 2-methoxy-3-[4-[2-[methyl-[3-phenyl-8-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,3-a:1',3'-e][7]annulen-11-yl]amino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(C(=O)OCC)OC)=CC=C1OCCN(C)C1C2=CC=C(C=3C=CC=CC=3)C=C2CCC2=CC(CCC=3C=CC=CC=3)=CC=C21 JNKGXOQFWWYMDL-UHFFFAOYSA-N 0.000 description 1
- CEIFQFOIBZAAIS-UHFFFAOYSA-N ethyl 2-methoxy-3-[4-[2-[methyl-[3-phenyl-9-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl]amino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(C(=O)OCC)OC)=CC=C1OCCN(C)C1C2=CC(CCC=3C=CC=CC=3)=CC=C2CCC2=CC(C=3C=CC=CC=3)=CC=C21 CEIFQFOIBZAAIS-UHFFFAOYSA-N 0.000 description 1
- NHVZPGGPFOTNPG-UHFFFAOYSA-N ethyl 2-methoxy-3-[4-[2-[methyl-[4-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,2-a:1',3'-e][7]annulen-11-yl]amino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(C(=O)OCC)OC)=CC=C1OCCN(C)C1C2=CC=CC(CCC=3C=CC=CC=3)=C2CCC2=CC=CC=C21 NHVZPGGPFOTNPG-UHFFFAOYSA-N 0.000 description 1
- ZFVLHDXHJDWOKK-UHFFFAOYSA-N ethyl 2-methoxy-3-[4-[2-[methyl-[7-(2-phenylethyl)-2-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl]amino]ethoxy]phenyl]propanoate Chemical compound C1=CC=C2C(N(C)CCOC=3C=CC(CC(OC)C(=O)OCC)=CC=3)C3=CC(CCC)=CC=C3CCC2=C1CCC1=CC=CC=C1 ZFVLHDXHJDWOKK-UHFFFAOYSA-N 0.000 description 1
- JZHHLYDZQCNTBE-UHFFFAOYSA-N ethyl 2-methoxy-3-[4-[2-[methyl-[7-(2-phenylethyl)-3-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl]amino]ethoxy]phenyl]propanoate Chemical compound C12=CC=CC(CCC=3C=CC=CC=3)=C2CCC2=CC(CCC)=CC=C2C1N(C)CCOC1=CC=C(CC(OC)C(=O)OCC)C=C1 JZHHLYDZQCNTBE-UHFFFAOYSA-N 0.000 description 1
- YGQMPSCCZIPJLJ-UHFFFAOYSA-N ethyl 2-methoxy-3-[4-[2-[methyl-[8-methyl-3-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,2-a:1',3'-e][7]annulen-11-yl]amino]ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(C(=O)OCC)OC)=CC=C1OCCN(C)C1C2=CC=C(CCC=3C=CC=CC=3)C=C2CCC2=CC(C)=CC=C21 YGQMPSCCZIPJLJ-UHFFFAOYSA-N 0.000 description 1
- NSKMGRJJCCVBSH-UHFFFAOYSA-N ethyl 3-[4-(2-bromoethoxy)phenyl]-2-ethoxypropanoate Chemical compound CCOC(=O)C(OCC)CC1=CC=C(OCCBr)C=C1 NSKMGRJJCCVBSH-UHFFFAOYSA-N 0.000 description 1
- LFNFOONLTSECEH-UHFFFAOYSA-N ethyl 3-[4-[2-(11h-dibenzo[1,2-a:1',2'-e][7]annulen-11-yloxy)ethoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCOC1C2=CC=CC=C2C=CC2=CC=CC=C21 LFNFOONLTSECEH-UHFFFAOYSA-N 0.000 description 1
- SUTDFDKTEDJWJO-UHFFFAOYSA-N ethyl 3-[4-[2-(6,11-dihydro-5h-dibenzo[1,2-a:1',2'-e][7]annulen-11-yloxy)ethoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCOC1C2=CC=CC=C2CCC2=CC=CC=C21 SUTDFDKTEDJWJO-UHFFFAOYSA-N 0.000 description 1
- SIZSMIWJJKRZJG-UHFFFAOYSA-N ethyl 3-[4-[2-[(2-benzyl-6,11-dihydro-5h-dibenzo[1,3-e:1',2'-f][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN(C)C1C2=CC(CC=3C=CC=CC=3)=CC=C2CCC2=CC=CC=C21 SIZSMIWJJKRZJG-UHFFFAOYSA-N 0.000 description 1
- OBJVDGALDHVOQJ-UHFFFAOYSA-N ethyl 3-[4-[2-[(3,9-diphenyl-11h-dibenzo[1,3-e:1',2'-f][7]annulen-11-yl)oxy]ethoxy]phenyl]-2-methoxypropanoate Chemical compound C1=CC(CC(C(=O)OCC)OC)=CC=C1OCCOC1C2=CC(C=3C=CC=CC=3)=CC=C2C=CC2=CC(C=3C=CC=CC=3)=CC=C21 OBJVDGALDHVOQJ-UHFFFAOYSA-N 0.000 description 1
- OEJAAMJYTDWQSK-UHFFFAOYSA-N ethyl 3-[4-[2-[(3-benzyl-6,11-dihydro-5h-dibenzo[1,2-a:1',3'-e][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN(C)C1C2=CC=C(CC=3C=CC=CC=3)C=C2CCC2=CC=CC=C21 OEJAAMJYTDWQSK-UHFFFAOYSA-N 0.000 description 1
- VFYMGEYTSDAKCM-UHFFFAOYSA-N ethyl 3-[4-[2-[(3-benzyl-8-methyl-6,11-dihydro-5h-dibenzo[1,2-a:1',3'-e][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN(C)C1C2=CC=C(CC=3C=CC=CC=3)C=C2CCC2=CC(C)=CC=C21 VFYMGEYTSDAKCM-UHFFFAOYSA-N 0.000 description 1
- KYGUIHDXJPBIGF-UHFFFAOYSA-N ethyl 3-[4-[2-[(3-benzyl-8-methyl-6,11-dihydro-5h-dibenzo[1,2-a:1',3'-e][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-methoxypropanoate Chemical compound C1=CC(CC(C(=O)OCC)OC)=CC=C1OCCN(C)C1C2=CC=C(CC=3C=CC=CC=3)C=C2CCC2=CC(C)=CC=C21 KYGUIHDXJPBIGF-UHFFFAOYSA-N 0.000 description 1
- RKPHQUJCBPJPAF-UHFFFAOYSA-N ethyl 3-[4-[2-[(3-benzyl-9-ethyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN(C)C1C2=CC(CC)=CC=C2CCC2=CC(CC=3C=CC=CC=3)=CC=C21 RKPHQUJCBPJPAF-UHFFFAOYSA-N 0.000 description 1
- OJJFQKXKXPOKIK-UHFFFAOYSA-N ethyl 3-[4-[2-[(3-benzyl-9-ethyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-methoxypropanoate Chemical compound C1=CC(CC(C(=O)OCC)OC)=CC=C1OCCN(C)C1C2=CC(CC)=CC=C2CCC2=CC(CC=3C=CC=CC=3)=CC=C21 OJJFQKXKXPOKIK-UHFFFAOYSA-N 0.000 description 1
- FJYGXIHXWFRXIC-UHFFFAOYSA-N ethyl 3-[4-[2-[(3-benzyl-9-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-ethoxypropanoate Chemical compound C=1C=C2C(N(C)CCOC=3C=CC(CC(OCC)C(=O)OCC)=CC=3)C3=CC(CCC)=CC=C3CCC2=CC=1CC1=CC=CC=C1 FJYGXIHXWFRXIC-UHFFFAOYSA-N 0.000 description 1
- HZPWXLGPFNFIHZ-UHFFFAOYSA-N ethyl 3-[4-[2-[(3-benzyl-9-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-methoxypropanoate Chemical compound C=1C=C2C(N(C)CCOC=3C=CC(CC(OC)C(=O)OCC)=CC=3)C3=CC(CCC)=CC=C3CCC2=CC=1CC1=CC=CC=C1 HZPWXLGPFNFIHZ-UHFFFAOYSA-N 0.000 description 1
- HNNNXHLDLQASON-UHFFFAOYSA-N ethyl 3-[4-[2-[(3-ethyl-9-phenyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-methoxypropanoate Chemical compound C1=CC(CC(C(=O)OCC)OC)=CC=C1OCCN(C)C1C2=CC(C=3C=CC=CC=3)=CC=C2CCC2=CC(CC)=CC=C21 HNNNXHLDLQASON-UHFFFAOYSA-N 0.000 description 1
- XRAAKBIDGJGQAH-UHFFFAOYSA-N ethyl 3-[4-[2-[(3-ethyl-9-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-methoxypropanoate Chemical compound C12=CC(CCC)=CC=C2CCC2=CC(CC)=CC=C2C1N(C)CCOC1=CC=C(CC(OC)C(=O)OCC)C=C1 XRAAKBIDGJGQAH-UHFFFAOYSA-N 0.000 description 1
- LOEJTSCGIFRKQK-UHFFFAOYSA-N ethyl 3-[4-[2-[(8-ethyl-3-phenyl-6,11-dihydro-5h-dibenzo[1,3-a:1',3'-e][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-methoxypropanoate Chemical compound C1=CC(CC(C(=O)OCC)OC)=CC=C1OCCN(C)C1C2=CC=C(C=3C=CC=CC=3)C=C2CCC2=CC(CC)=CC=C21 LOEJTSCGIFRKQK-UHFFFAOYSA-N 0.000 description 1
- VZTOOHHBHKKWFM-UHFFFAOYSA-N ethyl 3-[4-[2-[(9-benzyl-3-ethyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN(C)C1C2=CC(CC=3C=CC=CC=3)=CC=C2CCC2=CC(CC)=CC=C21 VZTOOHHBHKKWFM-UHFFFAOYSA-N 0.000 description 1
- AWHGEYUVADNQCG-UHFFFAOYSA-N ethyl 3-[4-[2-[(9-benzyl-3-ethyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-methoxypropanoate Chemical compound C1=CC(CC(C(=O)OCC)OC)=CC=C1OCCN(C)C1C2=CC(CC=3C=CC=CC=3)=CC=C2CCC2=CC(CC)=CC=C21 AWHGEYUVADNQCG-UHFFFAOYSA-N 0.000 description 1
- ZPTZBORTKWIQCA-UHFFFAOYSA-N ethyl 3-[4-[2-[(9-benzyl-3-methyl-6,11-dihydro-5h-dibenzo[1,3-e:1',2'-f][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN(C)C1C2=CC(CC=3C=CC=CC=3)=CC=C2CCC2=CC(C)=CC=C21 ZPTZBORTKWIQCA-UHFFFAOYSA-N 0.000 description 1
- XSJDXEPFWFATTI-UHFFFAOYSA-N ethyl 3-[4-[2-[(9-benzyl-3-methyl-6,11-dihydro-5h-dibenzo[1,3-e:1',2'-f][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-methoxypropanoate Chemical compound C1=CC(CC(C(=O)OCC)OC)=CC=C1OCCN(C)C1C2=CC(CC=3C=CC=CC=3)=CC=C2CCC2=CC(C)=CC=C21 XSJDXEPFWFATTI-UHFFFAOYSA-N 0.000 description 1
- LIRYOQNNWNJUAY-UHFFFAOYSA-N ethyl 3-[4-[2-[(9-ethyl-3-methyl-6,11-dihydro-5h-dibenzo[1,3-e:1',2'-f][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-methoxypropanoate Chemical compound C1=CC(CC(C(=O)OCC)OC)=CC=C1OCCN(C)C1C2=CC(CC)=CC=C2CCC2=CC(C)=CC=C21 LIRYOQNNWNJUAY-UHFFFAOYSA-N 0.000 description 1
- VKEDWMDSBFQIGT-UHFFFAOYSA-N ethyl 3-[4-[2-[(9-ethyl-3-propyl-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl)-methylamino]ethoxy]phenyl]-2-methoxypropanoate Chemical compound C12=CC(CC)=CC=C2CCC2=CC(CCC)=CC=C2C1N(C)CCOC1=CC=C(CC(OC)C(=O)OCC)C=C1 VKEDWMDSBFQIGT-UHFFFAOYSA-N 0.000 description 1
- UGJJRDPFGDMKLI-UHFFFAOYSA-N ethyl 3-[4-[2-[[2-butyl-7-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl]-methylamino]ethoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC=C2C(N(C)CCOC=3C=CC(CC(OCC)C(=O)OCC)=CC=3)C3=CC(CCCC)=CC=C3CCC2=C1CCC1=CC=CC=C1 UGJJRDPFGDMKLI-UHFFFAOYSA-N 0.000 description 1
- JBCBUYZYZBMKCA-UHFFFAOYSA-N ethyl 3-[4-[2-[[2-butyl-7-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl]-methylamino]ethoxy]phenyl]-2-methoxypropanoate Chemical compound C1=CC=C2C(N(C)CCOC=3C=CC(CC(OC)C(=O)OCC)=CC=3)C3=CC(CCCC)=CC=C3CCC2=C1CCC1=CC=CC=C1 JBCBUYZYZBMKCA-UHFFFAOYSA-N 0.000 description 1
- POEBIRAEMODBCM-UHFFFAOYSA-N ethyl 3-[4-[2-[[2-ethyl-7-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl]-methylamino]ethoxy]phenyl]-2-methoxypropanoate Chemical compound C1=CC(CC(C(=O)OCC)OC)=CC=C1OCCN(C)C1C2=CC=CC(CCC=3C=CC=CC=3)=C2CCC2=CC=C(CC)C=C21 POEBIRAEMODBCM-UHFFFAOYSA-N 0.000 description 1
- ULXSAUKPMWOBRN-UHFFFAOYSA-N ethyl 3-[4-[2-[[3-benzyl-8-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,3-a:1',3'-e][7]annulen-11-yl]-methylamino]ethoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN(C)C1C2=CC=C(CC=3C=CC=CC=3)C=C2CCC2=CC(CCC=3C=CC=CC=3)=CC=C21 ULXSAUKPMWOBRN-UHFFFAOYSA-N 0.000 description 1
- PQOFLXNLPIAXGT-UHFFFAOYSA-N ethyl 3-[4-[2-[[3-benzyl-8-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,3-a:1',3'-e][7]annulen-11-yl]-methylamino]ethoxy]phenyl]-2-methoxypropanoate Chemical compound C1=CC(CC(C(=O)OCC)OC)=CC=C1OCCN(C)C1C2=CC=C(CC=3C=CC=CC=3)C=C2CCC2=CC(CCC=3C=CC=CC=3)=CC=C21 PQOFLXNLPIAXGT-UHFFFAOYSA-N 0.000 description 1
- GTYXDBQLWXDRSY-UHFFFAOYSA-N ethyl 3-[4-[2-[[3-benzyl-9-(2-phenylethyl)-6,11-dihydro-5h-dibenzo[1,3-e:1',3'-f][7]annulen-11-yl]-methylamino]ethoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(CC(OCC)C(=O)OCC)=CC=C1OCCN(C)C1C2=CC(CCC=3C=CC=CC=3)=CC=C2CCC2=CC(CC=3C=CC=CC=3)=CC=C21 GTYXDBQLWXDRSY-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
- C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
- C07C217/22—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by carbon atoms having at least two bonds to oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D313/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D313/12—[b,e]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
- C07D321/12—Eight-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D337/12—[b,e]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/30—Ortho- or ortho- and peri-condensed systems containing three rings containing seven-membered rings
- C07C2603/32—Dibenzocycloheptenes; Hydrogenated dibenzocycloheptenes
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Obesity (AREA)
- Neurology (AREA)
- Urology & Nephrology (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurosurgery (AREA)
- Endocrinology (AREA)
- Biomedical Technology (AREA)
- Child & Adolescent Psychology (AREA)
- Reproductive Health (AREA)
- Emergency Medicine (AREA)
- Psychiatry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK199801356 | 1998-10-21 | ||
DKPA199801356 | 1998-10-21 | ||
PCT/DK1999/000574 WO2000023417A1 (fr) | 1998-10-21 | 1999-10-19 | Nouveaux composes, leur preparation et leur utilisation |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2002527503A true JP2002527503A (ja) | 2002-08-27 |
Family
ID=8103962
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2000577145A Pending JP2002527503A (ja) | 1998-10-21 | 1999-10-19 | 新規化合物類、それらの調製及び使用 |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP1123269A1 (fr) |
JP (1) | JP2002527503A (fr) |
AU (1) | AU6325899A (fr) |
WO (1) | WO2000023417A1 (fr) |
Families Citing this family (65)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002532416A (ja) * | 1998-12-17 | 2002-10-02 | マインドセット・バイオファーマシューティカルズ・(ユーエスエイ)・インコーポレイテッド | 脳のグルコース利用の増進 |
WO2001066135A1 (fr) | 2000-03-08 | 2001-09-13 | Novo Nordisk A/S | Reduction des lipides seriques |
US6987123B2 (en) | 2001-07-26 | 2006-01-17 | Cadila Healthcare Limited | Heterocyclic compounds, their preparation, pharmaceutical compositions containing them and their use in medicine |
WO2003031432A1 (fr) | 2001-10-12 | 2003-04-17 | Novo Nordisk A/S | Nouvelles piperidines substituees |
CA2471049A1 (fr) | 2001-12-21 | 2003-07-10 | Novo Nordisk A/S | Derives amide utiles en tant qu'activateurs de la glucokinase |
US7015345B2 (en) | 2002-02-21 | 2006-03-21 | Asahi Kasei Pharma Corporation | Propionic acid derivatives |
PL215132B1 (pl) | 2002-06-27 | 2013-10-31 | Novo Nordisk As | Pochodna arylokarbonylowa jako srodek terapeutyczny, jej zastosowanie i kompozycja farmaceutyczna ja zawierajaca |
JP2007503453A (ja) | 2003-05-14 | 2007-02-22 | ノボ ノルディスク アクティーゼルスカブ | 肥満症を治療するための新規化合物 |
CN101497654A (zh) | 2003-09-30 | 2009-08-05 | 诺沃挪第克公司 | 黑皮素受体激动剂 |
EP1694356B1 (fr) | 2003-12-09 | 2011-02-16 | Novo Nordisk A/S | Regulation d'une preference alimentaire au moyen d'agonistes de glp-1 |
KR101196313B1 (ko) | 2004-01-06 | 2012-11-07 | 노보 노르디스크 에이/에스 | 헤테로아릴-유리아 및 글루코키나아제 활성제로서의 그들의사용 |
US20080125403A1 (en) | 2004-04-02 | 2008-05-29 | Merck & Co., Inc. | Method of Treating Men with Metabolic and Anthropometric Disorders |
JP2007536344A (ja) | 2004-05-04 | 2007-12-13 | ノボ ノルディスク アクティーゼルスカブ | 新規のインドール誘導体 |
US8410047B2 (en) | 2004-06-11 | 2013-04-02 | Novo Nordisk A/S | Counteracting drug-induced obesity using GLP-1 agonists |
US8263551B2 (en) | 2004-11-22 | 2012-09-11 | Novo Nordisk A/S | Soluble, stable insulin-containing formulations with a protamine salt |
JP2008521864A (ja) | 2004-12-03 | 2008-06-26 | トランステック・ファーマ、インコーポレイテッド | ヘテロ芳香族グルコキナーゼ活性化剤 |
RU2499795C2 (ru) | 2005-07-04 | 2013-11-27 | Хай Пойнт Фармасьютикалс, ЛЛС | Антагонисты гистаминовых н3-рецепторов |
CA2615938C (fr) | 2005-07-14 | 2014-04-29 | Novo-Nordisk A/S | Activateurs de l'uree glucokinase |
WO2007015805A1 (fr) | 2005-07-20 | 2007-02-08 | Eli Lilly And Company | Composés joints en position 1-amino |
AU2006342449B2 (en) | 2005-11-17 | 2012-03-01 | Eli Lilly And Company | Glucagon receptor antagonists, preparation and therapeutic uses |
AU2007229492B2 (en) | 2006-03-28 | 2011-11-03 | High Point Pharmaceuticals, Llc | Benzothiazoles having histamine H3 receptor activity |
EP2079732B9 (fr) | 2006-05-29 | 2012-03-21 | High Point Pharmaceuticals, LLC | 3-(1,3-benzodioxol-5-yl)-6-(4-cyclopropylpiperazin-1-yl)-pyradine, ses sels et solvates et son utilisation comme antagoniste du recepteur d'histamin h3 |
CA2669884A1 (fr) | 2006-11-15 | 2008-05-22 | High Point Pharmaceuticals, Llc | Nouveaux 2-(2-hydroxyphenyl)benzimidazoles utilises pour traiter l'obesite et le diabete |
ATE538109T1 (de) | 2006-11-15 | 2012-01-15 | High Point Pharmaceuticals Llc | Neue für die behandlung von obesitas und diabetes geeignete 2-(2-hydroxyphenyl)benzothiadiazine |
JP5226008B2 (ja) | 2007-01-11 | 2013-07-03 | ノボ・ノルデイスク・エー/エス | ウレアグルコキナーゼアクチベーター |
EP2154131A4 (fr) * | 2007-04-26 | 2011-09-21 | Pharmafrontier Co Ltd | Inhibiteur du récepteur couplé à protéine g et produit pharmaceutique |
US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
CN101772513B (zh) | 2007-06-04 | 2013-11-13 | 协同医药品公司 | 有效用于胃肠功能紊乱、炎症、癌症和其他疾病治疗的鸟苷酸环化酶激动剂 |
EP2328910B1 (fr) | 2008-06-04 | 2014-08-06 | Synergy Pharmaceuticals Inc. | Agonistes de guanylate cyclase utile dans le traitement de troubles gastro-intestinaux, d'une inflammation, d'un cancer et d'autres troubles |
EP3241839B1 (fr) | 2008-07-16 | 2019-09-04 | Bausch Health Ireland Limited | Agonistes de guanylate cyclase utiles pour le traitement de troubles gastro-intestinaux, inflammatoires, cancéreux et autres |
US8410284B2 (en) | 2008-10-22 | 2013-04-02 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
AU2009309037A1 (en) | 2008-10-31 | 2010-05-06 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
EP2538784B1 (fr) | 2010-02-25 | 2015-09-09 | Merck Sharp & Dohme Corp. | Dérivés de benzimidazole utiles comme agents antidiabétiques |
WO2011104378A1 (fr) | 2010-02-26 | 2011-09-01 | Novo Nordisk A/S | Peptides de traitement de l'obésité |
BR112012021231A2 (pt) | 2010-02-26 | 2015-09-08 | Basf Plant Science Co Gmbh | método para acentuar o rendimento em plantas, planta, construto, uso de um construto, método para a produção de uma planta transgênica, partes coletáveis de uma planta, produtos derivados de uma planta, uso de um ácido nucleíco e método para a produção de um produto |
AU2011231503C1 (en) | 2010-03-26 | 2016-03-03 | Novo Nordisk A/S | Novel glucagon analogues |
WO2012027331A1 (fr) | 2010-08-27 | 2012-03-01 | Ironwood Pharmaceuticals, Inc. | Compositions et procédés pour traiter ou prévenir un syndrome métabolique et des maladies et troubles associés |
US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
ES2569248T3 (es) | 2011-01-31 | 2016-05-09 | Cadila Healthcare Limited | Tratamiento para la lipodistrofia |
WO2012104834A1 (fr) | 2011-02-03 | 2012-08-09 | Pharmedica Ltd. | Nouveaux films à dissolution orale pour administration d'insuline, pour traitement du diabète |
BR112013021236B1 (pt) | 2011-02-25 | 2021-05-25 | Merck Sharp & Dohme Corp | composto derivado de benzimidazol, e, composição |
BR112013024076A2 (pt) | 2011-03-28 | 2016-12-06 | Novo Nordisk As | análogos de glucagon |
AR088161A1 (es) | 2011-09-23 | 2014-05-14 | Novo Nordisk As | Analogos de glucagon |
WO2013082106A1 (fr) | 2011-12-02 | 2013-06-06 | The General Hospital Corporation | Différenciation en adipocytes bruns |
MX2015001500A (es) | 2012-08-02 | 2015-04-08 | Merck Sharp & Dohme | Compuestos antidiabeticos triciclicos. |
US9840512B2 (en) | 2013-02-22 | 2017-12-12 | Merck Sharp & Dohme Corp. | Antidiabetic bicyclic compounds |
US9650375B2 (en) | 2013-03-14 | 2017-05-16 | Merck Sharp & Dohme Corp. | Indole derivatives useful as anti-diabetic agents |
JP2016514670A (ja) | 2013-03-15 | 2016-05-23 | シナジー ファーマシューティカルズ インコーポレイテッド | 他の薬物と組み合わせたグアニル酸シクラーゼ受容体アゴニスト |
WO2014151206A1 (fr) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonistes de la guanylate cyclase et leurs utilisations |
JP6594856B2 (ja) | 2013-04-18 | 2019-10-23 | ノヴォ ノルディスク アー/エス | 医療用の安定な遷延性glp−1/グルカゴン受容体コアゴニスト |
MX346943B (es) | 2013-04-22 | 2017-04-06 | Cadila Healthcare Ltd | Una nueva composición para esteatosis hepática no alcohólica (nafld). |
ES2889916T3 (es) | 2013-05-30 | 2022-01-14 | Cadila Healthcare Ltd | Un procedimiento para la preparación de pirroles con actividades hipolipidémicas e hipocolesterémicas |
CA2913737A1 (fr) | 2013-06-05 | 2014-12-11 | Synergy Pharmaceuticals, Inc. | Agonistes ultra-purs de guanylate cyclase c, leur procede de production et d'utilisation |
TW201636015A (zh) | 2013-07-05 | 2016-10-16 | 卡地拉保健有限公司 | 協同性組成物 |
IN2013MU02470A (fr) | 2013-07-25 | 2015-06-26 | Cadila Healthcare Ltd | |
IN2013MU02905A (fr) | 2013-09-06 | 2015-07-03 | Cadila Healthcare Ltd | |
WO2015051496A1 (fr) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Composés tricycliques antidiabétiques |
EP3151852A1 (fr) | 2014-06-04 | 2017-04-12 | Novo Nordisk A/S | Co-agonistes de récepteur du glucagon/glp-1 à usage médical |
WO2017064635A2 (fr) | 2015-10-14 | 2017-04-20 | Cadila Healthcare Limited | Composé pyrrole, compositions et procédé de préparation associé |
WO2018106518A1 (fr) | 2016-12-06 | 2018-06-14 | Merck Sharp & Dohme Corp. | Composés hétérocycliques antidiabétiques |
JP6840853B2 (ja) | 2016-12-09 | 2021-03-10 | カディラ・ヘルスケア・リミテッド | 原発性胆汁性胆管炎の治療 |
US10968232B2 (en) | 2016-12-20 | 2021-04-06 | Merck Sharp & Dohme Corp. | Antidiabetic spirochroman compounds |
MA49883A (fr) | 2017-03-15 | 2021-04-21 | Novo Nordisk As | Composés bicycliques aptes à se lier au récepteur de mélanocortine 4 |
US20210221867A1 (en) | 2018-05-15 | 2021-07-22 | Novo Nordisk A/S | Compounds Capable of Binding to Melanocortin 4 Receptor |
WO2020053414A1 (fr) | 2018-09-14 | 2020-03-19 | Novo Nordisk A/S | Composés bicycliques aptes à se lier aux agonistes du récepteur de la mélanocortine 4 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR9508468A (pt) * | 1994-07-29 | 1997-11-25 | Smithkline Beecham Plc | Composto processo para a preparação do mesmo composição farmacéutica processos para o tratamento e/ou profilaxia de hiperglicemia em um mamifero humano ou não humano e para o tratamento de hiperlípidemia hipertensão doença cardiovascular alguns distúrbios de alimentação o tratamento e/ou profilaxia de doença renal a prevenção revers o estabilização ou retardo da progressão de microalbuminuria em um mamifero humano ou não humano uso do composto e composto intermediário |
GB9600464D0 (en) * | 1996-01-09 | 1996-03-13 | Smithkline Beecham Plc | Novel method |
GB9606805D0 (en) * | 1996-03-30 | 1996-06-05 | Glaxo Wellcome Inc | Medicaments |
JPH10182550A (ja) * | 1996-12-25 | 1998-07-07 | Mitsui Chem Inc | ヒドロキシ安息香酸誘導体およびそれを有効成分として含有する医薬品 |
WO1999019313A1 (fr) * | 1997-10-27 | 1999-04-22 | Dr. Reddy's Research Foundation | Nouveaux composes tricycliques et leur utilisation en medecine, procede de preparation de ces derniers et compositions pharmaceutiques les contenant |
-
1999
- 1999-10-19 EP EP99950504A patent/EP1123269A1/fr not_active Withdrawn
- 1999-10-19 WO PCT/DK1999/000574 patent/WO2000023417A1/fr not_active Application Discontinuation
- 1999-10-19 AU AU63258/99A patent/AU6325899A/en not_active Abandoned
- 1999-10-19 JP JP2000577145A patent/JP2002527503A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
EP1123269A1 (fr) | 2001-08-16 |
AU6325899A (en) | 2000-05-08 |
WO2000023417A1 (fr) | 2000-04-27 |
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