ZA200308783B - Quinoline derivatives as ligands for the neuropeptide Y receptor. - Google Patents
Quinoline derivatives as ligands for the neuropeptide Y receptor. Download PDFInfo
- Publication number
- ZA200308783B ZA200308783B ZA200308783A ZA200308783A ZA200308783B ZA 200308783 B ZA200308783 B ZA 200308783B ZA 200308783 A ZA200308783 A ZA 200308783A ZA 200308783 A ZA200308783 A ZA 200308783A ZA 200308783 B ZA200308783 B ZA 200308783B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- pyrrolidin
- alkyl
- quinolin
- hydrogen
- Prior art date
Links
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title claims description 6
- 239000003446 ligand Substances 0.000 title description 3
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 2
- 108050002826 Neuropeptide Y Receptor Proteins 0.000 title 1
- 102000012301 Neuropeptide Y receptor Human genes 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 89
- -1 aryl-SO2-O-alkyl Chemical group 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 239000001257 hydrogen Substances 0.000 claims description 50
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 19
- 229940086609 Lipase inhibitor Drugs 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 208000008589 Obesity Diseases 0.000 claims description 13
- 125000006193 alkinyl group Chemical group 0.000 claims description 13
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 13
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 13
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 13
- 235000020824 obesity Nutrition 0.000 claims description 13
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical group CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 claims description 13
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 229960001243 orlistat Drugs 0.000 claims description 12
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 238000011321 prophylaxis Methods 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 8
- 208000030814 Eating disease Diseases 0.000 claims description 7
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 7
- 206010003246 arthritis Diseases 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 206010012601 diabetes mellitus Diseases 0.000 claims description 7
- 235000014632 disordered eating Nutrition 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 101710151321 Melanostatin Proteins 0.000 claims description 5
- 125000003725 azepanyl group Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 5
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 5
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 5
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 4
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- HFVCWXRIRISOEA-UHFFFAOYSA-N 2-[(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)oxymethyl]benzonitrile Chemical compound C=12C=CC(OCC=3C(=CC=CC=3)C#N)=CC2=NC(C)=CC=1N1CCCC1 HFVCWXRIRISOEA-UHFFFAOYSA-N 0.000 claims description 2
- HTWNTQBDROIOEZ-UHFFFAOYSA-N 2-methyl-4-pyrrolidin-1-ylquinolin-7-ol Chemical compound C=12C=CC(O)=CC2=NC(C)=CC=1N1CCCC1 HTWNTQBDROIOEZ-UHFFFAOYSA-N 0.000 claims description 2
- SRCYQRXUBMEAPQ-UHFFFAOYSA-N 3-[[4-(azepan-1-yl)-2-methylquinolin-7-yl]oxymethyl]benzonitrile Chemical compound C=12C=CC(OCC=3C=C(C=CC=3)C#N)=CC2=NC(C)=CC=1N1CCCCCC1 SRCYQRXUBMEAPQ-UHFFFAOYSA-N 0.000 claims description 2
- DPMAQIWJJZJKLV-UHFFFAOYSA-N 4-(azepan-1-yl)-2-methyl-7-(pyridin-4-ylmethoxy)quinoline Chemical compound C=12C=CC(OCC=3C=CN=CC=3)=CC2=NC(C)=CC=1N1CCCCCC1 DPMAQIWJJZJKLV-UHFFFAOYSA-N 0.000 claims description 2
- NHZYJKKSOGTTMR-UHFFFAOYSA-N 4-[(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)oxymethyl]benzonitrile Chemical compound C=12C=CC(OCC=3C=CC(=CC=3)C#N)=CC2=NC(C)=CC=1N1CCCC1 NHZYJKKSOGTTMR-UHFFFAOYSA-N 0.000 claims description 2
- XFBKURUTJJKCKP-UHFFFAOYSA-N 4-[(6-butyl-4-pyrrolidin-1-ylquinolin-7-yl)oxymethyl]benzonitrile Chemical compound CCCCC1=CC2=C(N3CCCC3)C=CN=C2C=C1OCC1=CC=C(C#N)C=C1 XFBKURUTJJKCKP-UHFFFAOYSA-N 0.000 claims description 2
- NXANOKNNJGBJJU-UHFFFAOYSA-N 4-[(6-fluoro-2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)oxymethyl]benzonitrile Chemical compound C=12C=C(F)C(OCC=3C=CC(=CC=3)C#N)=CC2=NC(C)=CC=1N1CCCC1 NXANOKNNJGBJJU-UHFFFAOYSA-N 0.000 claims description 2
- ZLJRLUWCTUDGGW-UHFFFAOYSA-N 4-[[4-(azepan-1-yl)-2-methylquinolin-7-yl]oxymethyl]benzonitrile Chemical compound C=12C=CC(OCC=3C=CC(=CC=3)C#N)=CC2=NC(C)=CC=1N1CCCCCC1 ZLJRLUWCTUDGGW-UHFFFAOYSA-N 0.000 claims description 2
- JAGFRBPZTHOFHK-IBGZPJMESA-N 4-[[4-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]-2-methylquinolin-7-yl]oxymethyl]benzonitrile Chemical compound C=12C=CC(OCC=3C=CC(=CC=3)C#N)=CC2=NC(C)=CC=1N1CCC[C@H]1CO JAGFRBPZTHOFHK-IBGZPJMESA-N 0.000 claims description 2
- OVIOWFMKGQXDFO-SFHVURJKSA-N 4-[[4-[(3s)-3-hydroxypyrrolidin-1-yl]-2-methylquinolin-7-yl]oxymethyl]benzonitrile Chemical compound C=12C=CC(OCC=3C=CC(=CC=3)C#N)=CC2=NC(C)=CC=1N1CC[C@H](O)C1 OVIOWFMKGQXDFO-SFHVURJKSA-N 0.000 claims description 2
- CILNSTLMXGWWKH-UHFFFAOYSA-N 6-butyl-4-pyrrolidin-1-ylquinolin-7-ol Chemical compound C1=CN=C2C=C(O)C(CCCC)=CC2=C1N1CCCC1 CILNSTLMXGWWKH-UHFFFAOYSA-N 0.000 claims description 2
- XHQZQRBRMJGODJ-UHFFFAOYSA-N 6-fluoro-7-[(2-fluoropyridin-3-yl)methoxy]-2-methyl-4-pyrrolidin-1-ylquinoline Chemical compound C=12C=C(F)C(OCC=3C(=NC=CC=3)F)=CC2=NC(C)=CC=1N1CCCC1 XHQZQRBRMJGODJ-UHFFFAOYSA-N 0.000 claims description 2
- PBVJXDHCRUNAMA-UHFFFAOYSA-N 7-[(2-chloropyridin-3-yl)methoxy]-2-methyl-4-pyrrolidin-1-ylquinoline Chemical compound C=12C=CC(OCC=3C(=NC=CC=3)Cl)=CC2=NC(C)=CC=1N1CCCC1 PBVJXDHCRUNAMA-UHFFFAOYSA-N 0.000 claims description 2
- NHXYFTFKSJDZSH-SFHVURJKSA-N 7-[(2-chloropyridin-3-yl)methoxy]-4-[(3s)-3-ethoxypyrrolidin-1-yl]-2-methylquinoline Chemical compound C1[C@@H](OCC)CCN1C1=CC(C)=NC2=CC(OCC=3C(=NC=CC=3)Cl)=CC=C12 NHXYFTFKSJDZSH-SFHVURJKSA-N 0.000 claims description 2
- TYTFNCKBHQNAFN-UHFFFAOYSA-N 7-[(2-chloropyridin-3-yl)methoxy]-6-fluoro-2-methyl-4-pyrrolidin-1-ylquinoline Chemical compound C=12C=C(F)C(OCC=3C(=NC=CC=3)Cl)=CC2=NC(C)=CC=1N1CCCC1 TYTFNCKBHQNAFN-UHFFFAOYSA-N 0.000 claims description 2
- NFLYDVKEEWHEKP-UHFFFAOYSA-N 7-[(3-chlorophenyl)methoxy]-2-methyl-4-pyrrolidin-1-ylquinoline Chemical compound C=12C=CC(OCC=3C=C(Cl)C=CC=3)=CC2=NC(C)=CC=1N1CCCC1 NFLYDVKEEWHEKP-UHFFFAOYSA-N 0.000 claims description 2
- AGTMGARQEGRFBT-UHFFFAOYSA-N 7-[(3-methoxyphenyl)methoxy]-2-methyl-4-pyrrolidin-1-ylquinoline Chemical compound COC1=CC=CC(COC=2C=C3N=C(C)C=C(C3=CC=2)N2CCCC2)=C1 AGTMGARQEGRFBT-UHFFFAOYSA-N 0.000 claims description 2
- NUXDJOBRDWPOTK-UHFFFAOYSA-N 7-[(4-chlorophenyl)methoxy]-2-methyl-4-pyrrolidin-1-ylquinoline Chemical compound C=12C=CC(OCC=3C=CC(Cl)=CC=3)=CC2=NC(C)=CC=1N1CCCC1 NUXDJOBRDWPOTK-UHFFFAOYSA-N 0.000 claims description 2
- AJOLWRGXBPZAIK-INIZCTEOSA-N [(2s)-1-[7-[(2-chloropyridin-3-yl)methoxy]-2-methylquinolin-4-yl]pyrrolidin-2-yl]methanol Chemical compound C=12C=CC(OCC=3C(=NC=CC=3)Cl)=CC2=NC(C)=CC=1N1CCC[C@H]1CO AJOLWRGXBPZAIK-INIZCTEOSA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 claims 2
- OVIOWFMKGQXDFO-GOSISDBHSA-N 4-[[4-[(3r)-3-hydroxypyrrolidin-1-yl]-2-methylquinolin-7-yl]oxymethyl]benzonitrile Chemical compound C=12C=CC(OCC=3C=CC(=CC=3)C#N)=CC2=NC(C)=CC=1N1CC[C@@H](O)C1 OVIOWFMKGQXDFO-GOSISDBHSA-N 0.000 claims 1
- QJPGZZBMFWSTCX-FQEVSTJZSA-N 4-[[4-[(3s)-3-methoxypyrrolidin-1-yl]-2-methylquinolin-7-yl]oxymethyl]benzonitrile Chemical compound C1[C@@H](OC)CCN1C1=CC(C)=NC2=CC(OCC=3C=CC(=CC=3)C#N)=CC=C12 QJPGZZBMFWSTCX-FQEVSTJZSA-N 0.000 claims 1
- HOVZPQYOIGUXKT-INIZCTEOSA-N [(2s)-1-[7-[(2-fluoropyridin-3-yl)methoxy]-2-methylquinolin-4-yl]pyrrolidin-2-yl]methanol Chemical compound C=12C=CC(OCC=3C(=NC=CC=3)F)=CC2=NC(C)=CC=1N1CCC[C@H]1CO HOVZPQYOIGUXKT-INIZCTEOSA-N 0.000 claims 1
- 238000006664 bond formation reaction Methods 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 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 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 230000037406 food intake Effects 0.000 description 5
- 125000002757 morpholinyl group Chemical group 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 208000024172 Cardiovascular disease Diseases 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 208000001647 Renal Insufficiency Diseases 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 235000012631 food intake Nutrition 0.000 description 4
- 201000006370 kidney failure Diseases 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 206010020710 Hyperphagia Diseases 0.000 description 3
- 102000004882 Lipase Human genes 0.000 description 3
- 108090001060 Lipase Proteins 0.000 description 3
- 239000004367 Lipase Substances 0.000 description 3
- SIKWOTFNWURSAY-UHFFFAOYSA-N Lipstatin Natural products CCCCCCC1C(CC(CC=CCC=CCCCCC)C(=O)OC(CC(C)C)NC=O)OC1=O SIKWOTFNWURSAY-UHFFFAOYSA-N 0.000 description 3
- 102400000064 Neuropeptide Y Human genes 0.000 description 3
- 102100029549 Neuropeptide Y receptor type 5 Human genes 0.000 description 3
- 101710198055 Neuropeptide Y receptor type 5 Proteins 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 235000019421 lipase Nutrition 0.000 description 3
- OQMAKWGYQLJJIA-CUOOPAIESA-N lipstatin Chemical compound CCCCCC[C@H]1[C@H](C[C@H](C\C=C/C\C=C/CCCCC)OC(=O)[C@H](CC(C)C)NC=O)OC1=O OQMAKWGYQLJJIA-CUOOPAIESA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- BPGXUIVWLQTVLZ-OFGSCBOVSA-N neuropeptide y(npy) Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 BPGXUIVWLQTVLZ-OFGSCBOVSA-N 0.000 description 3
- URPYMXQQVHTUDU-OFGSCBOVSA-N nucleopeptide y Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 URPYMXQQVHTUDU-OFGSCBOVSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 230000004584 weight gain Effects 0.000 description 3
- 235000019786 weight gain Nutrition 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 229940127470 Lipase Inhibitors Drugs 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- 108090000189 Neuropeptides Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000021407 appetite control Nutrition 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- JUPQABFQNIZLHE-UHFFFAOYSA-N (2-methyl-4-pyrrolidin-1-ylquinolin-7-yl) methanesulfonate Chemical compound C=12C=CC(OS(C)(=O)=O)=CC2=NC(C)=CC=1N1CCCC1 JUPQABFQNIZLHE-UHFFFAOYSA-N 0.000 description 1
- LLNKHPAEPMGSIY-UHFFFAOYSA-N (2-methyl-4-pyrrolidin-1-ylquinolin-7-yl) n,n-dimethylsulfamate Chemical compound C=1C(C)=NC2=CC(OS(=O)(=O)N(C)C)=CC=C2C=1N1CCCC1 LLNKHPAEPMGSIY-UHFFFAOYSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- DOGYZJVTBGICNB-QGZVFWFLSA-N (3r)-1-(2-methyl-7-phenylmethoxyquinolin-4-yl)pyrrolidin-3-ol Chemical compound C=12C=CC(OCC=3C=CC=CC=3)=CC2=NC(C)=CC=1N1CC[C@@H](O)C1 DOGYZJVTBGICNB-QGZVFWFLSA-N 0.000 description 1
- DOGYZJVTBGICNB-KRWDZBQOSA-N (3s)-1-(2-methyl-7-phenylmethoxyquinolin-4-yl)pyrrolidin-3-ol Chemical compound C=12C=CC(OCC=3C=CC=CC=3)=CC2=NC(C)=CC=1N1CC[C@H](O)C1 DOGYZJVTBGICNB-KRWDZBQOSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- KGKBYUMMVCIGKX-UHFFFAOYSA-N 2-(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)oxyethanol Chemical compound C=12C=CC(OCCO)=CC2=NC(C)=CC=1N1CCCC1 KGKBYUMMVCIGKX-UHFFFAOYSA-N 0.000 description 1
- GNNSGZZRRLGZNC-UHFFFAOYSA-N 2-[(6-fluoro-2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)oxymethyl]benzonitrile Chemical compound C=12C=C(F)C(OCC=3C(=CC=CC=3)C#N)=CC2=NC(C)=CC=1N1CCCC1 GNNSGZZRRLGZNC-UHFFFAOYSA-N 0.000 description 1
- ATYFGIJMLSUHHO-UHFFFAOYSA-N 2-[[4-(azepan-1-yl)-2-methylquinolin-7-yl]oxymethyl]benzonitrile Chemical compound C=12C=CC(OCC=3C(=CC=CC=3)C#N)=CC2=NC(C)=CC=1N1CCCCCC1 ATYFGIJMLSUHHO-UHFFFAOYSA-N 0.000 description 1
- GQYNPZQREXFPHJ-IBGZPJMESA-N 2-[[4-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]-2-methylquinolin-7-yl]oxymethyl]benzonitrile Chemical compound C=12C=CC(OCC=3C(=CC=CC=3)C#N)=CC2=NC(C)=CC=1N1CCC[C@H]1CO GQYNPZQREXFPHJ-IBGZPJMESA-N 0.000 description 1
- JOSSSUIHWOPXBO-NRFANRHFSA-N 2-[[4-[(3s)-3-ethoxypyrrolidin-1-yl]-2-methylquinolin-7-yl]oxymethyl]benzonitrile Chemical compound C1[C@@H](OCC)CCN1C1=CC(C)=NC2=CC(OCC=3C(=CC=CC=3)C#N)=CC=C12 JOSSSUIHWOPXBO-NRFANRHFSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- BPNMARONMYYRAB-PBVYKCSPSA-N 2-methyl-4-[(3S)-3-[2-(oxan-2-yloxy)ethoxy]pyrrolidin-1-yl]quinolin-7-ol Chemical compound O([C@H]1CCN(C1)C=1C=C(N=C2C=C(O)C=CC2=1)C)CCOC1CCCCO1 BPNMARONMYYRAB-PBVYKCSPSA-N 0.000 description 1
- OYIZBZHNRUNJKY-UHFFFAOYSA-N 2-methyl-4-pyrrolidin-1-yl-7-(thiophen-3-ylmethoxy)quinoline Chemical compound C=12C=CC(OCC3=CSC=C3)=CC2=NC(C)=CC=1N1CCCC1 OYIZBZHNRUNJKY-UHFFFAOYSA-N 0.000 description 1
- BKKAVMPVRGYDSB-UHFFFAOYSA-N 2-methyl-4-pyrrolidin-1-yl-7-[(6-pyrrolidin-1-ylpyridin-3-yl)methoxy]quinoline Chemical compound C=12C=CC(OCC=3C=NC(=CC=3)N3CCCC3)=CC2=NC(C)=CC=1N1CCCC1 BKKAVMPVRGYDSB-UHFFFAOYSA-N 0.000 description 1
- BWYBSQOTKSEORL-UHFFFAOYSA-N 2-methyl-4-pyrrolidin-1-yl-7-[[3-(trifluoromethyl)phenyl]methoxy]quinoline Chemical compound C=12C=CC(OCC=3C=C(C=CC=3)C(F)(F)F)=CC2=NC(C)=CC=1N1CCCC1 BWYBSQOTKSEORL-UHFFFAOYSA-N 0.000 description 1
- KBQVWLSVDGKWGD-UHFFFAOYSA-N 2-methyl-4-pyrrolidin-1-yl-7-[[4-(trifluoromethyl)phenyl]methoxy]quinoline Chemical compound C=12C=CC(OCC=3C=CC(=CC=3)C(F)(F)F)=CC2=NC(C)=CC=1N1CCCC1 KBQVWLSVDGKWGD-UHFFFAOYSA-N 0.000 description 1
- RSBOAGFOAIVADH-UHFFFAOYSA-N 2-methyl-7-(1-methylpiperidin-4-yl)oxy-4-pyrrolidin-1-ylquinoline Chemical compound C1CN(C)CCC1OC1=CC=C(C(=CC(C)=N2)N3CCCC3)C2=C1 RSBOAGFOAIVADH-UHFFFAOYSA-N 0.000 description 1
- DWNQBLQNRHZONO-UHFFFAOYSA-N 2-methyl-7-(2-methylpropoxy)-4-pyrrolidin-1-ylquinoline Chemical compound C=1C(C)=NC2=CC(OCC(C)C)=CC=C2C=1N1CCCC1 DWNQBLQNRHZONO-UHFFFAOYSA-N 0.000 description 1
- BRPQWOQWAACAMK-UHFFFAOYSA-N 2-methyl-7-(3-pyridin-2-ylpropoxy)-4-pyrrolidin-1-ylquinoline Chemical compound C=12C=CC(OCCCC=3N=CC=CC=3)=CC2=NC(C)=CC=1N1CCCC1 BRPQWOQWAACAMK-UHFFFAOYSA-N 0.000 description 1
- IDPAQJLOLYZOTG-UHFFFAOYSA-N 2-methyl-7-(oxolan-2-ylmethoxy)-4-pyrrolidin-1-ylquinoline Chemical compound C=12C=CC(OCC3OCCC3)=CC2=NC(C)=CC=1N1CCCC1 IDPAQJLOLYZOTG-UHFFFAOYSA-N 0.000 description 1
- VLAWRLXBRWVOHA-UHFFFAOYSA-N 2-methyl-7-(oxolan-3-yloxy)-4-pyrrolidin-1-ylquinoline Chemical compound C=12C=CC(OC3COCC3)=CC2=NC(C)=CC=1N1CCCC1 VLAWRLXBRWVOHA-UHFFFAOYSA-N 0.000 description 1
- UDXYZQHPSKBSOU-UHFFFAOYSA-N 2-methyl-7-(pyridin-2-ylmethoxy)-4-pyrrolidin-1-ylquinoline Chemical compound C=12C=CC(OCC=3N=CC=CC=3)=CC2=NC(C)=CC=1N1CCCC1 UDXYZQHPSKBSOU-UHFFFAOYSA-N 0.000 description 1
- XSRMUWXBTOQFMX-UHFFFAOYSA-N 2-methyl-7-(pyridin-3-ylmethoxy)-4-pyrrolidin-1-ylquinoline Chemical compound C=12C=CC(OCC=3C=NC=CC=3)=CC2=NC(C)=CC=1N1CCCC1 XSRMUWXBTOQFMX-UHFFFAOYSA-N 0.000 description 1
- XHCVPQALAKCWNA-UHFFFAOYSA-N 2-methyl-7-(pyridin-4-ylmethoxy)-4-pyrrolidin-1-ylquinoline Chemical compound C=12C=CC(OCC=3C=CN=CC=3)=CC2=NC(C)=CC=1N1CCCC1 XHCVPQALAKCWNA-UHFFFAOYSA-N 0.000 description 1
- JGKRQRGWKSAYMG-UHFFFAOYSA-N 2-methyl-7-[(1-methylpiperidin-4-yl)methoxy]-4-pyrrolidin-1-ylquinoline Chemical compound C1CN(C)CCC1COC1=CC=C(C(=CC(C)=N2)N3CCCC3)C2=C1 JGKRQRGWKSAYMG-UHFFFAOYSA-N 0.000 description 1
- LMBIJXFFBMNBNC-UHFFFAOYSA-N 2-methyl-7-[(2-methylpyridin-3-yl)methoxy]-4-pyrrolidin-1-ylquinoline Chemical compound C=12C=CC(OCC=3C(=NC=CC=3)C)=CC2=NC(C)=CC=1N1CCCC1 LMBIJXFFBMNBNC-UHFFFAOYSA-N 0.000 description 1
- DAEIAGGNKVFXFY-UHFFFAOYSA-N 2-methyl-7-[(6-methylpyridin-3-yl)methoxy]-4-pyrrolidin-1-ylquinoline Chemical compound C1=NC(C)=CC=C1COC1=CC=C(C(=CC(C)=N2)N3CCCC3)C2=C1 DAEIAGGNKVFXFY-UHFFFAOYSA-N 0.000 description 1
- XNABVCNTZBHDAW-UHFFFAOYSA-N 2-methyl-7-phenylmethoxy-4-pyrrolidin-1-ylquinoline Chemical compound C=12C=CC(OCC=3C=CC=CC=3)=CC2=NC(C)=CC=1N1CCCC1 XNABVCNTZBHDAW-UHFFFAOYSA-N 0.000 description 1
- QRNWQIDZFDTHPW-UHFFFAOYSA-N 2-methyl-7-propan-2-yloxy-4-pyrrolidin-1-ylquinoline Chemical compound C=1C(C)=NC2=CC(OC(C)C)=CC=C2C=1N1CCCC1 QRNWQIDZFDTHPW-UHFFFAOYSA-N 0.000 description 1
- 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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- HWGPFDNEFUUCKN-UHFFFAOYSA-N 3-[(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)oxymethyl]benzonitrile Chemical compound C=12C=CC(OCC=3C=C(C=CC=3)C#N)=CC2=NC(C)=CC=1N1CCCC1 HWGPFDNEFUUCKN-UHFFFAOYSA-N 0.000 description 1
- FMPGODFZPXPQMZ-UHFFFAOYSA-N 3-[(6-fluoro-2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)oxymethyl]benzonitrile Chemical compound C=12C=C(F)C(OCC=3C=C(C=CC=3)C#N)=CC2=NC(C)=CC=1N1CCCC1 FMPGODFZPXPQMZ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- HPVQPASUKDEBHL-UHFFFAOYSA-N 4-(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)oxybenzonitrile Chemical compound C=12C=CC(OC=3C=CC(=CC=3)C#N)=CC2=NC(C)=CC=1N1CCCC1 HPVQPASUKDEBHL-UHFFFAOYSA-N 0.000 description 1
- VJZKLTWJQIHBSP-UHFFFAOYSA-N 4-(2-methyl-7-phenylmethoxyquinolin-4-yl)morpholine Chemical compound C=12C=CC(OCC=3C=CC=CC=3)=CC2=NC(C)=CC=1N1CCOCC1 VJZKLTWJQIHBSP-UHFFFAOYSA-N 0.000 description 1
- OTUSZHWTKGSXDO-UHFFFAOYSA-N 4-(azepan-1-yl)-2-methyl-7-(pyridin-2-ylmethoxy)quinoline Chemical compound C=12C=CC(OCC=3N=CC=CC=3)=CC2=NC(C)=CC=1N1CCCCCC1 OTUSZHWTKGSXDO-UHFFFAOYSA-N 0.000 description 1
- DKCGXHRVPGAORG-UHFFFAOYSA-N 4-(azepan-1-yl)-2-methyl-7-phenylmethoxyquinoline Chemical compound C=12C=CC(OCC=3C=CC=CC=3)=CC2=NC(C)=CC=1N1CCCCCC1 DKCGXHRVPGAORG-UHFFFAOYSA-N 0.000 description 1
- XJMVLECIPJHGTF-UHFFFAOYSA-N 4-(azepan-1-yl)-2-methylquinolin-7-ol Chemical compound C=12C=CC(O)=CC2=NC(C)=CC=1N1CCCCCC1 XJMVLECIPJHGTF-UHFFFAOYSA-N 0.000 description 1
- LOYOMZVAFWLDOJ-UHFFFAOYSA-N 4-(azepan-1-yl)-7-[(3-chlorophenyl)methoxy]-2-methylquinoline Chemical compound C=12C=CC(OCC=3C=C(Cl)C=CC=3)=CC2=NC(C)=CC=1N1CCCCCC1 LOYOMZVAFWLDOJ-UHFFFAOYSA-N 0.000 description 1
- IECZTNLHFOJASS-UHFFFAOYSA-N 4-(azepan-1-yl)-7-[(3-methoxyphenyl)methoxy]-2-methylquinoline Chemical compound COC1=CC=CC(COC=2C=C3N=C(C)C=C(C3=CC=2)N2CCCCCC2)=C1 IECZTNLHFOJASS-UHFFFAOYSA-N 0.000 description 1
- RVKGSXOEUPQYAT-UHFFFAOYSA-N 4-(azepan-1-yl)-7-[(4-chlorophenyl)methoxy]-2-methylquinoline Chemical compound C=12C=CC(OCC=3C=CC(Cl)=CC=3)=CC2=NC(C)=CC=1N1CCCCCC1 RVKGSXOEUPQYAT-UHFFFAOYSA-N 0.000 description 1
- NREPAKQQAKWSBU-IBGZPJMESA-N 4-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]-2-methyl-7-phenylmethoxyquinoline Chemical compound COC[C@@H]1CCCN1C1=CC(C)=NC2=CC(OCC=3C=CC=CC=3)=CC=C12 NREPAKQQAKWSBU-IBGZPJMESA-N 0.000 description 1
- JUQPUEXSALIBJW-AWEZNQCLSA-N 4-[(3S)-3-(2-methoxyethoxy)pyrrolidin-1-yl]-2-methylquinolin-7-ol Chemical compound C1[C@@H](OCCOC)CCN1C1=CC(C)=NC2=CC(O)=CC=C12 JUQPUEXSALIBJW-AWEZNQCLSA-N 0.000 description 1
- QYQCYZAXJUSEJT-HNNXBMFYSA-N 4-[(3S)-3-(3-methoxypropoxy)pyrrolidin-1-yl]-2-methylquinolin-7-ol Chemical compound C1[C@@H](OCCCOC)CCN1C1=CC(C)=NC2=CC(O)=CC=C12 QYQCYZAXJUSEJT-HNNXBMFYSA-N 0.000 description 1
- GCBNADYDPAFXII-HNNXBMFYSA-N 4-[(3S)-3-(cyclopropylmethoxy)pyrrolidin-1-yl]-2-methylquinolin-7-ol Chemical compound O([C@H]1CCN(C1)C=1C=C(N=C2C=C(O)C=CC2=1)C)CC1CC1 GCBNADYDPAFXII-HNNXBMFYSA-N 0.000 description 1
- BSZYCCBUYXDANU-ZDUSSCGKSA-N 4-[(3S)-3-ethoxypyrrolidin-1-yl]-2-methylquinolin-7-ol Chemical compound C1[C@@H](OCC)CCN1C1=CC(C)=NC2=CC(O)=CC=C12 BSZYCCBUYXDANU-ZDUSSCGKSA-N 0.000 description 1
- KJYDTXYTHVCRLY-LBPRGKRZSA-N 4-[(3S)-3-methoxypyrrolidin-1-yl]-2-methylquinolin-7-ol Chemical compound C1[C@@H](OC)CCN1C1=CC(C)=NC2=CC(O)=CC=C12 KJYDTXYTHVCRLY-LBPRGKRZSA-N 0.000 description 1
- ARHAUJBDNJGAPQ-LJQANCHMSA-N 4-[(3r)-3-methoxypyrrolidin-1-yl]-2-methyl-7-phenylmethoxyquinoline Chemical compound C1[C@H](OC)CCN1C1=CC(C)=NC2=CC(OCC=3C=CC=CC=3)=CC=C12 ARHAUJBDNJGAPQ-LJQANCHMSA-N 0.000 description 1
- CBYSWKDGALCATF-NRFANRHFSA-N 4-[(3s)-3-(2-methoxyethoxy)pyrrolidin-1-yl]-2-methyl-7-phenylmethoxyquinoline Chemical compound C1[C@@H](OCCOC)CCN1C1=CC(C)=NC2=CC(OCC=3C=CC=CC=3)=CC=C12 CBYSWKDGALCATF-NRFANRHFSA-N 0.000 description 1
- PVNADSHSDFLKHQ-QFIPXVFZSA-N 4-[(3s)-3-(3-methoxypropoxy)pyrrolidin-1-yl]-2-methyl-7-phenylmethoxyquinoline Chemical compound C1[C@@H](OCCCOC)CCN1C1=CC(C)=NC2=CC(OCC=3C=CC=CC=3)=CC=C12 PVNADSHSDFLKHQ-QFIPXVFZSA-N 0.000 description 1
- KKLYYULYKZVYPL-QFIPXVFZSA-N 4-[(3s)-3-(cyclopropylmethoxy)pyrrolidin-1-yl]-2-methyl-7-phenylmethoxyquinoline Chemical compound O([C@H]1CCN(C1)C=1C=C(N=C2C=C(OCC=3C=CC=CC=3)C=CC2=1)C)CC1CC1 KKLYYULYKZVYPL-QFIPXVFZSA-N 0.000 description 1
- ABZTXQUYNILQIK-IBGZPJMESA-N 4-[(3s)-3-ethoxypyrrolidin-1-yl]-2-methyl-7-(pyridin-3-ylmethoxy)quinoline Chemical compound C1[C@@H](OCC)CCN1C1=CC(C)=NC2=CC(OCC=3C=NC=CC=3)=CC=C12 ABZTXQUYNILQIK-IBGZPJMESA-N 0.000 description 1
- ABWAKVYQYSRJEF-SFHVURJKSA-N 4-[(3s)-3-ethoxypyrrolidin-1-yl]-7-[(2-fluoropyridin-3-yl)methoxy]-2-methylquinoline Chemical compound C1[C@@H](OCC)CCN1C1=CC(C)=NC2=CC(OCC=3C(=NC=CC=3)F)=CC=C12 ABWAKVYQYSRJEF-SFHVURJKSA-N 0.000 description 1
- ARHAUJBDNJGAPQ-IBGZPJMESA-N 4-[(3s)-3-methoxypyrrolidin-1-yl]-2-methyl-7-phenylmethoxyquinoline Chemical compound C1[C@@H](OC)CCN1C1=CC(C)=NC2=CC(OCC=3C=CC=CC=3)=CC=C12 ARHAUJBDNJGAPQ-IBGZPJMESA-N 0.000 description 1
- NXYXRNQBYSNQPR-UHFFFAOYSA-N 4-[(6-bromo-2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)oxymethyl]benzonitrile Chemical compound C=12C=C(Br)C(OCC=3C=CC(=CC=3)C#N)=CC2=NC(C)=CC=1N1CCCC1 NXYXRNQBYSNQPR-UHFFFAOYSA-N 0.000 description 1
- SVSNAAOBHMAMHA-UHFFFAOYSA-N 4-[2-(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)oxyethyl]morpholine Chemical compound C=12C=CC(OCCN3CCOCC3)=CC2=NC(C)=CC=1N1CCCC1 SVSNAAOBHMAMHA-UHFFFAOYSA-N 0.000 description 1
- GOCYAMJDBSCJEW-UHFFFAOYSA-N 4-[3-(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)oxypropyl]morpholine Chemical compound C=12C=CC(OCCCN3CCOCC3)=CC2=NC(C)=CC=1N1CCCC1 GOCYAMJDBSCJEW-UHFFFAOYSA-N 0.000 description 1
- MAZPPISNMYXNSY-UHFFFAOYSA-N 4-[5-[(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)oxymethyl]pyridin-2-yl]morpholine Chemical compound C=12C=CC(OCC=3C=NC(=CC=3)N3CCOCC3)=CC2=NC(C)=CC=1N1CCCC1 MAZPPISNMYXNSY-UHFFFAOYSA-N 0.000 description 1
- JAGFRBPZTHOFHK-LJQANCHMSA-N 4-[[4-[(2r)-2-(hydroxymethyl)pyrrolidin-1-yl]-2-methylquinolin-7-yl]oxymethyl]benzonitrile Chemical compound C=12C=CC(OCC=3C=CC(=CC=3)C#N)=CC2=NC(C)=CC=1N1CCC[C@@H]1CO JAGFRBPZTHOFHK-LJQANCHMSA-N 0.000 description 1
- IDDKJADQZPZLMR-HXUWFJFHSA-N 4-[[4-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]-2-methylquinolin-7-yl]oxymethyl]benzonitrile Chemical compound C1[C@H](N(C)C)CCN1C1=CC(C)=NC2=CC(OCC=3C=CC(=CC=3)C#N)=CC=C12 IDDKJADQZPZLMR-HXUWFJFHSA-N 0.000 description 1
- MJSVCBVXUQHWLZ-NRFANRHFSA-N 4-[[4-[(3s)-3-(2-hydroxyethoxy)pyrrolidin-1-yl]-2-methylquinolin-7-yl]oxymethyl]benzonitrile Chemical compound C=12C=CC(OCC=3C=CC(=CC=3)C#N)=CC2=NC(C)=CC=1N1CC[C@H](OCCO)C1 MJSVCBVXUQHWLZ-NRFANRHFSA-N 0.000 description 1
- OPRTZDVTKDZBCY-QFIPXVFZSA-N 4-[[4-[(3s)-3-(2-methoxyethoxy)pyrrolidin-1-yl]-2-methylquinolin-7-yl]oxymethyl]benzonitrile Chemical compound C1[C@@H](OCCOC)CCN1C1=CC(C)=NC2=CC(OCC=3C=CC(=CC=3)C#N)=CC=C12 OPRTZDVTKDZBCY-QFIPXVFZSA-N 0.000 description 1
- RDJNXCKGLTZUPB-QHCPKHFHSA-N 4-[[4-[(3s)-3-(3-methoxypropoxy)pyrrolidin-1-yl]-2-methylquinolin-7-yl]oxymethyl]benzonitrile Chemical compound C1[C@@H](OCCCOC)CCN1C1=CC(C)=NC2=CC(OCC=3C=CC(=CC=3)C#N)=CC=C12 RDJNXCKGLTZUPB-QHCPKHFHSA-N 0.000 description 1
- VYDMPQALSDIXIQ-QHCPKHFHSA-N 4-[[4-[(3s)-3-(cyclopropylmethoxy)pyrrolidin-1-yl]-2-methylquinolin-7-yl]oxymethyl]benzonitrile Chemical compound O([C@H]1CCN(C1)C=1C=C(N=C2C=C(OCC=3C=CC(=CC=3)C#N)C=CC2=1)C)CC1CC1 VYDMPQALSDIXIQ-QHCPKHFHSA-N 0.000 description 1
- DNCNFUQWEFNIKJ-NRFANRHFSA-N 4-[[4-[(3s)-3-ethoxypyrrolidin-1-yl]-2-methylquinolin-7-yl]oxymethyl]benzonitrile Chemical compound C1[C@@H](OCC)CCN1C1=CC(C)=NC2=CC(OCC=3C=CC(=CC=3)C#N)=CC=C12 DNCNFUQWEFNIKJ-NRFANRHFSA-N 0.000 description 1
- SZCZIXJRKAXDPV-SFHVURJKSA-N 4-[[6-fluoro-4-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]-2-methylquinolin-7-yl]oxymethyl]benzonitrile Chemical compound C=12C=C(F)C(OCC=3C=CC(=CC=3)C#N)=CC2=NC(C)=CC=1N1CCC[C@H]1CO SZCZIXJRKAXDPV-SFHVURJKSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- QUFHJNPLHBOKRG-UHFFFAOYSA-N 4-pyrrolidin-1-ylquinolin-7-ol Chemical compound C=1C=NC2=CC(O)=CC=C2C=1N1CCCC1 QUFHJNPLHBOKRG-UHFFFAOYSA-N 0.000 description 1
- HFRRVIZAIBEVDL-UHFFFAOYSA-N 5-[(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)oxymethyl]pyridine-2-carbonitrile Chemical compound C=12C=CC(OCC=3C=NC(=CC=3)C#N)=CC2=NC(C)=CC=1N1CCCC1 HFRRVIZAIBEVDL-UHFFFAOYSA-N 0.000 description 1
- ZTVZIMAZBBAGCK-UHFFFAOYSA-N 5-[(6-fluoro-2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)oxymethyl]pyridine-2-carbonitrile Chemical compound C=12C=C(F)C(OCC=3C=NC(=CC=3)C#N)=CC2=NC(C)=CC=1N1CCCC1 ZTVZIMAZBBAGCK-UHFFFAOYSA-N 0.000 description 1
- FFZVNTCWZPMHGM-SFHVURJKSA-N 5-[[4-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]-2-methylquinolin-7-yl]oxymethyl]pyridine-2-carbonitrile Chemical compound C=12C=CC(OCC=3C=NC(=CC=3)C#N)=CC2=NC(C)=CC=1N1CCC[C@H]1CO FFZVNTCWZPMHGM-SFHVURJKSA-N 0.000 description 1
- HHHACGGZAGVVOZ-FQEVSTJZSA-N 5-[[4-[(3s)-3-ethoxypyrrolidin-1-yl]-2-methylquinolin-7-yl]oxymethyl]pyridine-2-carbonitrile Chemical compound C1[C@@H](OCC)CCN1C1=CC(C)=NC2=CC(OCC=3C=NC(=CC=3)C#N)=CC=C12 HHHACGGZAGVVOZ-FQEVSTJZSA-N 0.000 description 1
- IUZDXTKOCBBWIT-KRWDZBQOSA-N 5-[[6-fluoro-4-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]-2-methylquinolin-7-yl]oxymethyl]pyridine-2-carbonitrile Chemical compound C=12C=C(F)C(OCC=3C=NC(=CC=3)C#N)=CC2=NC(C)=CC=1N1CCC[C@H]1CO IUZDXTKOCBBWIT-KRWDZBQOSA-N 0.000 description 1
- RKCBBZIIIDKJKF-UHFFFAOYSA-N 6-bromo-2-methyl-4-pyrrolidin-1-ylquinolin-7-ol Chemical compound C=12C=C(Br)C(O)=CC2=NC(C)=CC=1N1CCCC1 RKCBBZIIIDKJKF-UHFFFAOYSA-N 0.000 description 1
- HCBYNCXRCQRUFM-UHFFFAOYSA-N 6-bromo-7-methoxy-2-methyl-4-pyrrolidin-1-ylquinoline Chemical compound C=12C=C(Br)C(OC)=CC2=NC(C)=CC=1N1CCCC1 HCBYNCXRCQRUFM-UHFFFAOYSA-N 0.000 description 1
- FFEPQUFWSPUQOV-UHFFFAOYSA-N 6-butyl-7-(cyclopropylmethoxy)-4-pyrrolidin-1-ylquinoline Chemical compound CCCCC1=CC2=C(N3CCCC3)C=CN=C2C=C1OCC1CC1 FFEPQUFWSPUQOV-UHFFFAOYSA-N 0.000 description 1
- WLVZMCMVZHTPRU-UHFFFAOYSA-N 6-butyl-7-ethoxy-4-pyrrolidin-1-ylquinoline Chemical compound C1=CN=C2C=C(OCC)C(CCCC)=CC2=C1N1CCCC1 WLVZMCMVZHTPRU-UHFFFAOYSA-N 0.000 description 1
- QBAPNEQKYOOKSM-UHFFFAOYSA-N 6-butyl-7-methoxy-4-pyrrolidin-1-ylquinoline Chemical compound C1=CN=C2C=C(OC)C(CCCC)=CC2=C1N1CCCC1 QBAPNEQKYOOKSM-UHFFFAOYSA-N 0.000 description 1
- WFBCKOGMOVLURH-UHFFFAOYSA-N 6-butyl-7-phenylmethoxy-4-pyrrolidin-1-ylquinoline Chemical compound CCCCC1=CC2=C(N3CCCC3)C=CN=C2C=C1OCC1=CC=CC=C1 WFBCKOGMOVLURH-UHFFFAOYSA-N 0.000 description 1
- OVZLPAGKKXUGNE-UHFFFAOYSA-N 6-fluoro-2-methyl-4-pyrrolidin-1-ylquinolin-7-ol Chemical compound C=12C=C(F)C(O)=CC2=NC(C)=CC=1N1CCCC1 OVZLPAGKKXUGNE-UHFFFAOYSA-N 0.000 description 1
- ZFJLTHIOPSXQNB-UHFFFAOYSA-N 6-fluoro-2-methyl-7-[(2-methylpyridin-3-yl)methoxy]-4-pyrrolidin-1-ylquinoline Chemical compound C=12C=C(F)C(OCC=3C(=NC=CC=3)C)=CC2=NC(C)=CC=1N1CCCC1 ZFJLTHIOPSXQNB-UHFFFAOYSA-N 0.000 description 1
- OXOQUVHYQRFEGV-UHFFFAOYSA-N 6-fluoro-2-methyl-7-phenylmethoxy-4-pyrrolidin-1-ylquinoline Chemical compound C=12C=C(F)C(OCC=3C=CC=CC=3)=CC2=NC(C)=CC=1N1CCCC1 OXOQUVHYQRFEGV-UHFFFAOYSA-N 0.000 description 1
- HHEOOKPSFHYFOD-JTQLQIEISA-N 6-fluoro-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-2-methylquinolin-7-ol Chemical compound C=12C=C(F)C(O)=CC2=NC(C)=CC=1N1CCC[C@H]1CO HHEOOKPSFHYFOD-JTQLQIEISA-N 0.000 description 1
- YAOWZIXHVQXXCM-UHFFFAOYSA-N 7-(2-methoxyethoxy)-2-methyl-4-pyrrolidin-1-ylquinoline Chemical compound C=1C(C)=NC2=CC(OCCOC)=CC=C2C=1N1CCCC1 YAOWZIXHVQXXCM-UHFFFAOYSA-N 0.000 description 1
- CPCZGHBEHUIWFK-UHFFFAOYSA-N 7-(cyclopropylmethoxy)-2-methyl-4-pyrrolidin-1-ylquinoline Chemical compound C=12C=CC(OCC3CC3)=CC2=NC(C)=CC=1N1CCCC1 CPCZGHBEHUIWFK-UHFFFAOYSA-N 0.000 description 1
- REYRSAIXWIZEQH-INIZCTEOSA-N 7-(cyclopropylmethoxy)-4-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]-2-methylquinoline Chemical compound COC[C@@H]1CCCN1C1=CC(C)=NC2=CC(OCC3CC3)=CC=C12 REYRSAIXWIZEQH-INIZCTEOSA-N 0.000 description 1
- DMZGGEABZIJPTL-UHFFFAOYSA-N 7-[(2-chloro-6-methylpyridin-3-yl)methoxy]-2-methyl-4-pyrrolidin-1-ylquinoline Chemical compound ClC1=NC(C)=CC=C1COC1=CC=C(C(=CC(C)=N2)N3CCCC3)C2=C1 DMZGGEABZIJPTL-UHFFFAOYSA-N 0.000 description 1
- QOZPZKXKYRFRQJ-UHFFFAOYSA-N 7-[(2-chlorophenyl)methoxy]-2-methyl-4-pyrrolidin-1-ylquinoline Chemical compound C=12C=CC(OCC=3C(=CC=CC=3)Cl)=CC2=NC(C)=CC=1N1CCCC1 QOZPZKXKYRFRQJ-UHFFFAOYSA-N 0.000 description 1
- XEMQCFMQGTYNOP-UHFFFAOYSA-N 7-[(2-fluoropyridin-3-yl)methoxy]-2-methyl-4-pyrrolidin-1-ylquinoline Chemical compound C=12C=CC(OCC=3C(=NC=CC=3)F)=CC2=NC(C)=CC=1N1CCCC1 XEMQCFMQGTYNOP-UHFFFAOYSA-N 0.000 description 1
- DHELLFMTWRQAKJ-KRWDZBQOSA-N 7-[(2-fluoropyridin-3-yl)methoxy]-4-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]-2-methylquinoline Chemical compound COC[C@@H]1CCCN1C1=CC(C)=NC2=CC(OCC=3C(=NC=CC=3)F)=CC=C12 DHELLFMTWRQAKJ-KRWDZBQOSA-N 0.000 description 1
- DUBHFUCWBUVNHO-UHFFFAOYSA-N 7-[(2-methoxyphenyl)methoxy]-2-methyl-4-pyrrolidin-1-ylquinoline Chemical compound COC1=CC=CC=C1COC1=CC=C(C(=CC(C)=N2)N3CCCC3)C2=C1 DUBHFUCWBUVNHO-UHFFFAOYSA-N 0.000 description 1
- JJTUVMXXIZYZHL-UHFFFAOYSA-N 7-[(3,4-dimethoxyphenyl)methoxy]-2-methyl-4-pyrrolidin-1-ylquinoline Chemical compound C1=C(OC)C(OC)=CC=C1COC1=CC=C(C(=CC(C)=N2)N3CCCC3)C2=C1 JJTUVMXXIZYZHL-UHFFFAOYSA-N 0.000 description 1
- IDFXLNBGDSLJEN-UHFFFAOYSA-N 7-[(3,5-dimethoxyphenyl)methoxy]-2-methyl-4-pyrrolidin-1-ylquinoline Chemical compound COC1=CC(OC)=CC(COC=2C=C3N=C(C)C=C(C3=CC=2)N2CCCC2)=C1 IDFXLNBGDSLJEN-UHFFFAOYSA-N 0.000 description 1
- XLFYXISBJPDSCK-UHFFFAOYSA-N 7-[(4-methoxyphenyl)methoxy]-2-methyl-4-pyrrolidin-1-ylquinoline Chemical compound C1=CC(OC)=CC=C1COC1=CC=C(C(=CC(C)=N2)N3CCCC3)C2=C1 XLFYXISBJPDSCK-UHFFFAOYSA-N 0.000 description 1
- FTECBAFEXPMOTO-UHFFFAOYSA-N 7-[(5-chlorothiophen-2-yl)methoxy]-2-methyl-4-pyrrolidin-1-ylquinoline Chemical compound C=12C=CC(OCC=3SC(Cl)=CC=3)=CC2=NC(C)=CC=1N1CCCC1 FTECBAFEXPMOTO-UHFFFAOYSA-N 0.000 description 1
- DPSPLSHURCVOLO-UHFFFAOYSA-N 7-[(6-chloropyridin-3-yl)methoxy]-2-methyl-4-pyrrolidin-1-ylquinoline Chemical compound C=12C=CC(OCC=3C=NC(Cl)=CC=3)=CC2=NC(C)=CC=1N1CCCC1 DPSPLSHURCVOLO-UHFFFAOYSA-N 0.000 description 1
- PNOUWQOKJBWQCM-UHFFFAOYSA-N 7-ethoxy-2-methyl-4-pyrrolidin-1-ylquinoline Chemical compound C=1C(C)=NC2=CC(OCC)=CC=C2C=1N1CCCC1 PNOUWQOKJBWQCM-UHFFFAOYSA-N 0.000 description 1
- IMCGSRKRWIILQY-UHFFFAOYSA-N 7-methoxy-2-methyl-4-pyrrolidin-1-ylquinoline Chemical compound C=1C(C)=NC2=CC(OC)=CC=C2C=1N1CCCC1 IMCGSRKRWIILQY-UHFFFAOYSA-N 0.000 description 1
- LFRBEHIMBYETAP-UHFFFAOYSA-N 7-methoxy-4-pyrrolidin-1-ylquinolin-2-amine Chemical compound C=1C(N)=NC2=CC(OC)=CC=C2C=1N1CCCC1 LFRBEHIMBYETAP-UHFFFAOYSA-N 0.000 description 1
- HWCVAOLZJIPSPV-UHFFFAOYSA-N 7-methoxy-4-pyrrolidin-1-ylquinoline Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1N1CCCC1 HWCVAOLZJIPSPV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- QYOVMAREBTZLBT-KTKRTIGZSA-N CCCCCCCC\C=C/CCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO QYOVMAREBTZLBT-KTKRTIGZSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 102100031416 Gastric triacylglycerol lipase Human genes 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- 239000005913 Maltodextrin Substances 0.000 description 1
- 229920002774 Maltodextrin Polymers 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- 229940116685 Neuropeptide receptor antagonist Drugs 0.000 description 1
- 102000003797 Neuropeptides Human genes 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 206010033307 Overweight Diseases 0.000 description 1
- 108050006759 Pancreatic lipases Proteins 0.000 description 1
- 102000019280 Pancreatic lipases Human genes 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- SGJOBMSHODRWLJ-SFHVURJKSA-N [(2s)-1-(2-methyl-7-phenylmethoxyquinolin-4-yl)pyrrolidin-2-yl]methanol Chemical compound C=12C=CC(OCC=3C=CC=CC=3)=CC2=NC(C)=CC=1N1CCC[C@H]1CO SGJOBMSHODRWLJ-SFHVURJKSA-N 0.000 description 1
- SCVUAYSRWBVKJK-KRWDZBQOSA-N [(2s)-1-(6-fluoro-2-methyl-7-phenylmethoxyquinolin-4-yl)pyrrolidin-2-yl]methanol Chemical compound C=12C=C(F)C(OCC=3C=CC=CC=3)=CC2=NC(C)=CC=1N1CCC[C@H]1CO SCVUAYSRWBVKJK-KRWDZBQOSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229960000913 crospovidone Drugs 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- JQNNQJXVFCCBSL-UHFFFAOYSA-N ethyl 2-(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)oxyacetate Chemical compound C=1C(C)=NC2=CC(OCC(=O)OCC)=CC=C2C=1N1CCCC1 JQNNQJXVFCCBSL-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 108010091264 gastric triacylglycerol lipase Proteins 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 210000003016 hypothalamus Anatomy 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940035034 maltodextrin Drugs 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- JJIBACXWJHRORI-UHFFFAOYSA-N n,n,2,2-tetramethyl-3-(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)oxypropan-1-amine Chemical compound C=1C(C)=NC2=CC(OCC(C)(C)CN(C)C)=CC=C2C=1N1CCCC1 JJIBACXWJHRORI-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000000369 oxido group Chemical group [*]=O 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000035924 thermogenesis Effects 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Endocrinology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01112370 | 2001-05-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200308783B true ZA200308783B (en) | 2005-02-11 |
Family
ID=8177497
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200308783A ZA200308783B (en) | 2001-05-21 | 2003-11-11 | Quinoline derivatives as ligands for the neuropeptide Y receptor. |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US6818767B2 (zh) |
| EP (1) | EP1395564B1 (zh) |
| JP (1) | JP3715280B2 (zh) |
| KR (1) | KR100621287B1 (zh) |
| CN (1) | CN100376557C (zh) |
| AR (1) | AR035979A1 (zh) |
| AT (1) | ATE387428T1 (zh) |
| AU (1) | AU2002338896B2 (zh) |
| BR (1) | BR0209957A (zh) |
| CA (1) | CA2446324A1 (zh) |
| DE (1) | DE60225274T2 (zh) |
| ES (1) | ES2300478T3 (zh) |
| GT (1) | GT200200090A (zh) |
| MX (1) | MXPA03010565A (zh) |
| PA (1) | PA8545301A1 (zh) |
| PE (1) | PE20021155A1 (zh) |
| UY (1) | UY27300A1 (zh) |
| WO (1) | WO2002094789A1 (zh) |
| ZA (1) | ZA200308783B (zh) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6900226B2 (en) * | 2000-09-06 | 2005-05-31 | Hoffman-La Roche Inc. | Neuropeptide Y antagonists |
| AU2002352878B2 (en) * | 2001-11-27 | 2007-11-22 | Merck Sharp & Dohme Corp. | 2-Aminoquinoline compounds |
| JP4216196B2 (ja) * | 2002-02-04 | 2009-01-28 | エフ．ホフマン−ラ ロシュ アーゲー | Ｎｐｙアンタゴニストとしてのキノリン誘導体 |
| US7105526B2 (en) | 2002-06-28 | 2006-09-12 | Banyu Pharmaceuticals Co., Ltd. | Benzimidazole derivatives |
| JP2005535648A (ja) | 2002-07-05 | 2005-11-24 | エフ．ホフマン−ラ ロシュ アーゲー | キナゾリン誘導体 |
| MXPA05001328A (es) | 2002-08-07 | 2005-04-28 | Hoffmann La Roche | Derivados de tiazol. |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| MXPA05009722A (es) * | 2003-03-10 | 2006-03-09 | Schering Corp | Inhibidores heterociclicos de cinasa: metodos de uso y sintesis. |
| ATE547404T1 (de) | 2003-09-22 | 2012-03-15 | Msd Kk | Piperidinderivate |
| AU2004289303A1 (en) | 2003-11-10 | 2005-05-26 | Synta Pharmaceuticals, Corp. | Fused heterocyclic compounds |
| US20080125403A1 (en) | 2004-04-02 | 2008-05-29 | Merck & Co., Inc. | Method of Treating Men with Metabolic and Anthropometric Disorders |
| US20060183763A1 (en) * | 2004-12-31 | 2006-08-17 | Pfizer Inc | Novel pyrrolidyl derivatives of heteroaromatic compounds |
| US8138206B2 (en) | 2005-05-30 | 2012-03-20 | Msd. K.K. | Piperidine derivative |
| WO2007018248A1 (ja) | 2005-08-10 | 2007-02-15 | Banyu Pharmaceutical Co., Ltd. | ピリドン化合物 |
| US7875633B2 (en) | 2005-08-24 | 2011-01-25 | Banyu Pharmaceutical Co., Ltd. | Phenylpyridone derivative |
| WO2007029847A1 (ja) | 2005-09-07 | 2007-03-15 | Banyu Pharmaceutical Co., Ltd. | 二環性芳香族置換ピリドン誘導体 |
| WO2007049798A1 (ja) | 2005-10-27 | 2007-05-03 | Banyu Pharmaceutical Co., Ltd. | 新規ベンゾオキサチイン誘導体 |
| AU2006312557B2 (en) | 2005-11-10 | 2011-12-08 | Msd K.K. | Aza-substituted spiro derivative |
| WO2008020302A2 (en) * | 2006-08-17 | 2008-02-21 | Pfizer Products Inc. | Heteroaromatic quinoline-based compounds as phosphodiesterase (pde) inhibitors |
| AU2007301126A1 (en) | 2006-09-28 | 2008-04-03 | Banyu Pharmaceutical Co., Ltd. | Diaryl ketimine derivative |
| JP5319518B2 (ja) | 2007-04-02 | 2013-10-16 | Ｍｓｄ株式会社 | インドールジオン誘導体 |
| WO2008141077A1 (en) * | 2007-05-10 | 2008-11-20 | Janssen Pharmaceutica N.V. | Process for the preparation of tetrahydroquinolinyl, benzoxazine and benzothiazine derivatives |
| BRPI0811745B1 (pt) | 2007-05-17 | 2019-06-04 | Helperby Therapeutics Limited | Compostos de 4-(pirrolidin-1-il)quinolina, uso e processo para a preparação dos mesmos, formulação farmacêutica -- |
| US20080303428A1 (en) * | 2007-06-01 | 2008-12-11 | Vsevolod Rostovtsev | Chrysenes for green luminescent applications |
| WO2008151257A2 (en) | 2007-06-04 | 2008-12-11 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| 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 |
| CA2705318C (en) * | 2007-11-15 | 2013-12-31 | Boehringer Ingelheim International Gmbh | Inhibitors of human immunodeficiency virus replication |
| EA019259B1 (ru) | 2007-11-16 | 2014-02-28 | Джилид Сайенсиз, Инк. | Ингибиторы репликации вируса иммунодефицита человека |
| US20110015181A1 (en) | 2008-03-06 | 2011-01-20 | Makoto Ando | Alkylaminopyridine derivative |
| US20110015198A1 (en) | 2008-03-28 | 2011-01-20 | Banyu Pharmaceutical Co., Inc. | Diarylmethylamide derivative having melanin-concentrating hormone receptor antagonism |
| EP2328910B1 (en) | 2008-06-04 | 2014-08-06 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| CA2727914A1 (en) | 2008-06-19 | 2009-12-23 | Banyu Pharmaceutical Co., Ltd. | Spirodiamine-diaryl ketoxime derivative technical field |
| AU2009270833B2 (en) | 2008-07-16 | 2015-02-19 | Bausch Health Ireland Limited | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
| AU2009277736A1 (en) | 2008-07-30 | 2010-02-04 | Banyu Pharmaceutical Co., Ltd. | (5-membered)-(5-membered) or (5-membered)-(6-membered) fused ring cycloalkylamine derivative |
| CA2741125A1 (en) | 2008-10-22 | 2010-04-29 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| WO2010051206A1 (en) | 2008-10-31 | 2010-05-06 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| CA2786314A1 (en) | 2010-02-25 | 2011-09-01 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| PE20140859A1 (es) | 2011-02-25 | 2014-07-25 | Merck Sharp & Dohme | Novedosos derivados de azabencimidazol ciclico utiles como agentes antidiabeticos |
| BR112015002080A2 (pt) | 2012-08-02 | 2017-07-04 | Merck Sharp & Dohme | composto, composição farmacêutica, uso de um composto, e, método de tratamento ou de prevenção de um transtorno, de uma condição ou de uma doença |
| EP2958562A4 (en) | 2013-02-22 | 2016-08-10 | Merck Sharp & Dohme | BICYCLIC ANTIDIABETIC COMPOUNDS |
| US9650375B2 (en) | 2013-03-14 | 2017-05-16 | Merck Sharp & Dohme Corp. | Indole derivatives useful as anti-diabetic agents |
| CA2905438A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| EP2968439A2 (en) | 2013-03-15 | 2016-01-20 | Synergy Pharmaceuticals Inc. | Compositions useful for the treatment of gastrointestinal disorders |
| US10011637B2 (en) | 2013-06-05 | 2018-07-03 | Synergy Pharmaceuticals, Inc. | Ultra-pure agonists of guanylate cyclase C, method of making and using same |
| WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| EP3551176A4 (en) | 2016-12-06 | 2020-06-24 | Merck Sharp & Dohme Corp. | ANTIDIABETIC HETEROCYCLIC COMPOUNDS |
| WO2018118670A1 (en) | 2016-12-20 | 2018-06-28 | Merck Sharp & Dohme Corp. | Antidiabetic spirochroman compounds |
| CA3069524A1 (en) | 2017-07-14 | 2019-01-17 | Innate Tumor Immunity, Inc. | Nlrp3 modulators |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU43730A1 (zh) * | 1962-06-14 | 1963-07-13 | ||
| US3272824A (en) * | 1962-12-06 | 1966-09-13 | Norwich Pharma Co | 4-amino-6, 7-di(lower) alkoxyquinolines |
| US3812127A (en) * | 1966-10-31 | 1974-05-21 | Pfizer | 4-(quinolin-4-yl)piperazine-1-carboxylic acid esters |
| US4035367A (en) * | 1974-09-09 | 1977-07-12 | Sandoz, Inc. | Hydroxyalkyl-substituted-amino-quinolines |
| CA1247547A (en) | 1983-06-22 | 1988-12-28 | Paul Hadvary | Leucine derivatives |
| CA1328881C (en) | 1984-12-21 | 1994-04-26 | Pierre Barbier | Process for the manufacture of oxetanones |
| CA1270837A (en) | 1984-12-21 | 1990-06-26 | Hoffmann-La Roche Limited | Oxetanones |
| CA2035917C (en) | 1990-02-13 | 2001-10-02 | John L. Krstenansky | Stabilized sulfonate, sulfate, phosphonate and phosphate derivatives of hirudin |
| US5274143A (en) | 1991-07-23 | 1993-12-28 | Hoffmann-La Roche Inc. | Process for the preparation of (R)-3-hexyl-5,6-dihydro-4-hydroxy-6-undecyl-2H-pyran-2-one and (R)-5,6-dihydro-6-undecyl-2H-pyran-2,4(3H)-dione |
| ATE480521T1 (de) * | 1996-10-01 | 2010-09-15 | Kyowa Hakko Kirin Co Ltd | Stickstoff enthaltende heterocyclische verbindungen |
| US6004996A (en) | 1997-02-05 | 1999-12-21 | Hoffman-La Roche Inc. | Tetrahydrolipstatin containing compositions |
| US6267952B1 (en) | 1998-01-09 | 2001-07-31 | Geltex Pharmaceuticals, Inc. | Lipase inhibiting polymers |
| WO2000009122A1 (en) | 1998-08-14 | 2000-02-24 | F. Hoffmann-La Roche Ag | Pharmaceutical compositions containing lipase inhibitors |
| CN1152680C (zh) | 1998-08-14 | 2004-06-09 | 霍夫曼-拉罗奇有限公司 | 含有脂酶抑制剂和壳聚糖的药物组合物 |
| AU1047401A (en) * | 1999-11-08 | 2001-06-06 | Cytion Sa | Apparatus and methods for positioning and analyzing biological membranous objects |
| US6900226B2 (en) * | 2000-09-06 | 2005-05-31 | Hoffman-La Roche Inc. | Neuropeptide Y antagonists |
-
2002
- 2002-05-08 MX MXPA03010565A patent/MXPA03010565A/es active IP Right Grant
- 2002-05-08 JP JP2002591462A patent/JP3715280B2/ja not_active Expired - Fee Related
- 2002-05-08 CN CNB028104013A patent/CN100376557C/zh not_active Expired - Fee Related
- 2002-05-08 DE DE60225274T patent/DE60225274T2/de not_active Expired - Fee Related
- 2002-05-08 WO PCT/EP2002/005120 patent/WO2002094789A1/en active IP Right Grant
- 2002-05-08 BR BR0209957-8A patent/BR0209957A/pt not_active IP Right Cessation
- 2002-05-08 AT AT02771639T patent/ATE387428T1/de not_active IP Right Cessation
- 2002-05-08 EP EP02771639A patent/EP1395564B1/en not_active Expired - Lifetime
- 2002-05-08 KR KR1020037015121A patent/KR100621287B1/ko not_active IP Right Cessation
- 2002-05-08 AU AU2002338896A patent/AU2002338896B2/en not_active Ceased
- 2002-05-08 ES ES02771639T patent/ES2300478T3/es not_active Expired - Lifetime
- 2002-05-08 CA CA002446324A patent/CA2446324A1/en not_active Abandoned
- 2002-05-16 PA PA20028545301A patent/PA8545301A1/es unknown
- 2002-05-17 PE PE2002000425A patent/PE20021155A1/es not_active Application Discontinuation
- 2002-05-17 AR ARP020101836A patent/AR035979A1/es not_active Application Discontinuation
- 2002-05-20 GT GT200200090A patent/GT200200090A/es unknown
- 2002-05-20 US US10/151,505 patent/US6818767B2/en not_active Expired - Fee Related
- 2002-05-21 UY UY27300A patent/UY27300A1/es not_active Application Discontinuation
-
2003
- 2003-11-11 ZA ZA200308783A patent/ZA200308783B/en unknown
-
2004
- 2004-05-24 US US10/852,509 patent/US20050049413A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| BR0209957A (pt) | 2004-03-30 |
| ATE387428T1 (de) | 2008-03-15 |
| MXPA03010565A (es) | 2004-03-02 |
| UY27300A1 (es) | 2002-11-29 |
| AR035979A1 (es) | 2004-07-28 |
| PE20021155A1 (es) | 2002-12-17 |
| US20050049413A1 (en) | 2005-03-03 |
| JP3715280B2 (ja) | 2005-11-09 |
| EP1395564A1 (en) | 2004-03-10 |
| WO2002094789A1 (en) | 2002-11-28 |
| DE60225274D1 (de) | 2008-04-10 |
| AU2002338896B2 (en) | 2006-04-27 |
| US20020198194A1 (en) | 2002-12-26 |
| US6818767B2 (en) | 2004-11-16 |
| KR100621287B1 (ko) | 2006-09-13 |
| PA8545301A1 (es) | 2003-01-24 |
| CA2446324A1 (en) | 2002-11-28 |
| DE60225274T2 (de) | 2009-03-26 |
| JP2004536066A (ja) | 2004-12-02 |
| EP1395564B1 (en) | 2008-02-27 |
| GT200200090A (es) | 2003-06-19 |
| ES2300478T3 (es) | 2008-06-16 |
| KR20030096416A (ko) | 2003-12-24 |
| CN100376557C (zh) | 2008-03-26 |
| CN1522249A (zh) | 2004-08-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200308783B (en) | Quinoline derivatives as ligands for the neuropeptide Y receptor. | |
| EP1689721B1 (en) | Aminopyrazole derivatives as gsk-3 inhibitors | |
| RU2298002C2 (ru) | Производные хинолина в качестве антагонистов npy | |
| JP5075832B2 (ja) | 肺高血圧を処置するためのジアリールウレア | |
| RU2300531C2 (ru) | Хинолиновые производные в качестве антагонистов нейропептида y | |
| JP2004536066A5 (zh) | ||
| EP1072266B1 (en) | Thienylazolylalcoxyethanamines, their preparation and their application as medicaments | |
| CN101686952A (zh) | 新型钙离子通道调节剂 | |
| JP2007533687A (ja) | 月経前の及び他の女性の性的障害の治療におけるフリバンセリンの使用 | |
| AU2002338896A1 (en) | Quinoline derivatives as ligands for the neuropeptide Y receptor | |
| CN108864151A (zh) | 杂环胺及其用途 | |
| JP2008539195A (ja) | 新規のオキサジアゾール誘導体及びそれらの医学的使用 | |
| JP2008511569A (ja) | 注意欠如活動過多障害の治療方法 | |
| JP2007508336A (ja) | モノアミン神経伝達物質再取り込みインヒビター及びアセチルコリンエステラーゼインヒビターを含む医薬組成物 | |
| CN107567454A (zh) | 用于治疗cns障碍的稠合二氢‑4h‑吡唑并[5,1‑c][1,4]噁嗪基化合物及其类似物 | |
| TW200407147A (en) | Use of inhibitors of the EGFR-mediated signal transduction for the treatment of benign prostatic hyperplasia (BPH) / prostatic hypertrophy | |
| JP2007516170A (ja) | ＧＳＫ−３阻害剤としてのピラゾロ［３，４−ｂ］ピリジン−６−オン | |
| CA3188751A1 (en) | Combination of an alpha2-adrenoceptor subtype c (alpha-2c) antagonist with a task1/3 channel blocker for the treatment of sleep apnea | |
| KR102639048B1 (ko) | 히스타민-3 수용체 역작용제에 의한 치료 방법 | |
| Wang et al. | Synthesis and immunosuppressant activity of pyrazole carboxamides | |
| IL275817B1 (en) | Tricyclic compounds, preparations and their medical applications | |
| JPH07149647A (ja) | 抗真菌物質の抗真菌作用増強剤 | |
| US20040029901A1 (en) | Quinazoline derivatives | |
| JP3919272B2 (ja) | キナゾリン系化合物 | |
| WO2007034778A1 (ja) | 睡眠障害予防治療剤 |