CA2613001A1 - Quinoline 3 -sulfonate esters as nk3 receptor modulators - Google Patents
Quinoline 3 -sulfonate esters as nk3 receptor modulators Download PDFInfo
- Publication number
- CA2613001A1 CA2613001A1 CA002613001A CA2613001A CA2613001A1 CA 2613001 A1 CA2613001 A1 CA 2613001A1 CA 002613001 A CA002613001 A CA 002613001A CA 2613001 A CA2613001 A CA 2613001A CA 2613001 A1 CA2613001 A1 CA 2613001A1
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- 6alkyl
- independently selected
- occurrence
- halogen
- 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.)
- Abandoned
Links
- 108010040716 Neurokinin-3 Receptors Proteins 0.000 title description 19
- 102000002003 Neurokinin-3 Receptors Human genes 0.000 title description 19
- ITXXHPLNLYEVQT-UHFFFAOYSA-N quinoline-3-sulfonic acid Chemical class C1=CC=CC2=CC(S(=O)(=O)O)=CN=C21 ITXXHPLNLYEVQT-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 84
- 238000000034 method Methods 0.000 claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 56
- 229910052736 halogen Inorganic materials 0.000 claims description 55
- 150000002367 halogens Chemical class 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 37
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 24
- 125000005842 heteroatom Chemical group 0.000 claims description 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 125000004434 sulfur atom Chemical group 0.000 claims description 24
- 201000010099 disease Diseases 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- -1 sulfonate ester Chemical class 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 16
- 239000002243 precursor Substances 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 14
- 101001125071 Homo sapiens Neuromedin-K receptor Proteins 0.000 claims description 13
- 102100029409 Neuromedin-K receptor Human genes 0.000 claims description 12
- 208000008589 Obesity Diseases 0.000 claims description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 11
- 235000020824 obesity Nutrition 0.000 claims description 11
- 208000019901 Anxiety disease Diseases 0.000 claims description 10
- 230000036506 anxiety Effects 0.000 claims description 10
- 238000011321 prophylaxis Methods 0.000 claims description 10
- 201000000980 schizophrenia Diseases 0.000 claims description 10
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 8
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 8
- 208000005171 Dysmenorrhea Diseases 0.000 claims description 8
- 206010013935 Dysmenorrhoea Diseases 0.000 claims description 8
- 206010060862 Prostate cancer Diseases 0.000 claims description 8
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 8
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 8
- 208000028017 Psychotic disease Diseases 0.000 claims description 8
- 208000024313 Testicular Neoplasms Diseases 0.000 claims description 8
- 206010057644 Testis cancer Diseases 0.000 claims description 8
- 206010047700 Vomiting Diseases 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 239000003098 androgen Substances 0.000 claims description 8
- 229940030486 androgens Drugs 0.000 claims description 8
- 208000010877 cognitive disease Diseases 0.000 claims description 8
- 208000027866 inflammatory disease Diseases 0.000 claims description 8
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 8
- 201000011461 pre-eclampsia Diseases 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 201000003120 testicular cancer Diseases 0.000 claims description 8
- 230000009286 beneficial effect Effects 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- BLWLOUSTXZIEHT-NRFANRHFSA-N [2-phenyl-4-[[(1s)-1-phenylpropyl]carbamoyl]quinolin-3-yl] methanesulfonate Chemical compound N([C@@H](CC)C=1C=CC=CC=1)C(=O)C(C1=CC=CC=C1N=1)=C(OS(C)(=O)=O)C=1C1=CC=CC=C1 BLWLOUSTXZIEHT-NRFANRHFSA-N 0.000 claims description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000000314 lubricant Substances 0.000 claims description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 3
- DTCHSUWUAMDDQE-UHFFFAOYSA-N [2-(3-fluorophenyl)-4-(1-phenylpropylcarbamoyl)quinolin-3-yl] methanesulfonate Chemical compound C=1C=CC=CC=1C(CC)NC(=O)C(C1=CC=CC=C1N=1)=C(OS(C)(=O)=O)C=1C1=CC=CC(F)=C1 DTCHSUWUAMDDQE-UHFFFAOYSA-N 0.000 claims description 2
- UIMBINDRAFQBBF-UHFFFAOYSA-N [2-(3-fluorophenyl)-4-[1-(3-fluorophenyl)propylcarbamoyl]quinolin-3-yl] methanesulfonate Chemical compound C=1C=CC(F)=CC=1C(CC)NC(=O)C(C1=CC=CC=C1N=1)=C(OS(C)(=O)=O)C=1C1=CC=CC(F)=C1 UIMBINDRAFQBBF-UHFFFAOYSA-N 0.000 claims description 2
- UIMBINDRAFQBBF-NRFANRHFSA-N [2-(3-fluorophenyl)-4-[[(1s)-1-(3-fluorophenyl)propyl]carbamoyl]quinolin-3-yl] methanesulfonate Chemical compound N([C@@H](CC)C=1C=C(F)C=CC=1)C(=O)C(C1=CC=CC=C1N=1)=C(OS(C)(=O)=O)C=1C1=CC=CC(F)=C1 UIMBINDRAFQBBF-NRFANRHFSA-N 0.000 claims description 2
- GSNAKJOHZLOXGL-UHFFFAOYSA-N [2-phenyl-4-(1-phenylpropylcarbamoyl)quinolin-3-yl] 2,2,2-trifluoroethanesulfonate Chemical compound C=1C=CC=CC=1C(CC)NC(=O)C(C1=CC=CC=C1N=1)=C(OS(=O)(=O)CC(F)(F)F)C=1C1=CC=CC=C1 GSNAKJOHZLOXGL-UHFFFAOYSA-N 0.000 claims description 2
- QCAHEHRIDFGTGA-UHFFFAOYSA-N [2-phenyl-4-(1-phenylpropylcarbamoyl)quinolin-3-yl] 3,3,3-trifluoropropane-1-sulfonate Chemical compound C=1C=CC=CC=1C(CC)NC(=O)C(C1=CC=CC=C1N=1)=C(OS(=O)(=O)CCC(F)(F)F)C=1C1=CC=CC=C1 QCAHEHRIDFGTGA-UHFFFAOYSA-N 0.000 claims description 2
- IVBLZTMRPBCUOW-UHFFFAOYSA-N [2-phenyl-4-(1-phenylpropylcarbamoyl)quinolin-3-yl] cyclopropanesulfonate Chemical compound C=1C=CC=CC=1C(CC)NC(=O)C(C1=CC=CC=C1N=C1C=2C=CC=CC=2)=C1OS(=O)(=O)C1CC1 IVBLZTMRPBCUOW-UHFFFAOYSA-N 0.000 claims description 2
- AZNUQIWEPSDBGA-UHFFFAOYSA-N [2-phenyl-4-(1-phenylpropylcarbamoyl)quinolin-3-yl] ethanesulfonate Chemical compound C=1C=CC=CC=1C(CC)NC(=O)C(C1=CC=CC=C1N=1)=C(OS(=O)(=O)CC)C=1C1=CC=CC=C1 AZNUQIWEPSDBGA-UHFFFAOYSA-N 0.000 claims description 2
- VRRJAJRQBMCIIO-UHFFFAOYSA-N [2-phenyl-4-(1-phenylpropylcarbamoyl)quinolin-3-yl] trifluoromethanesulfonate Chemical compound C=1C=CC=CC=1C(CC)NC(=O)C(C1=CC=CC=C1N=1)=C(OS(=O)(=O)C(F)(F)F)C=1C1=CC=CC=C1 VRRJAJRQBMCIIO-UHFFFAOYSA-N 0.000 claims description 2
- GSNAKJOHZLOXGL-NRFANRHFSA-N [2-phenyl-4-[[(1s)-1-phenylpropyl]carbamoyl]quinolin-3-yl] 2,2,2-trifluoroethanesulfonate Chemical compound N([C@@H](CC)C=1C=CC=CC=1)C(=O)C(C1=CC=CC=C1N=1)=C(OS(=O)(=O)CC(F)(F)F)C=1C1=CC=CC=C1 GSNAKJOHZLOXGL-NRFANRHFSA-N 0.000 claims description 2
- QCAHEHRIDFGTGA-QFIPXVFZSA-N [2-phenyl-4-[[(1s)-1-phenylpropyl]carbamoyl]quinolin-3-yl] 3,3,3-trifluoropropane-1-sulfonate Chemical compound N([C@@H](CC)C=1C=CC=CC=1)C(=O)C(C1=CC=CC=C1N=1)=C(OS(=O)(=O)CCC(F)(F)F)C=1C1=CC=CC=C1 QCAHEHRIDFGTGA-QFIPXVFZSA-N 0.000 claims description 2
- IVBLZTMRPBCUOW-QHCPKHFHSA-N [2-phenyl-4-[[(1s)-1-phenylpropyl]carbamoyl]quinolin-3-yl] cyclopropanesulfonate Chemical compound N([C@@H](CC)C=1C=CC=CC=1)C(=O)C(C1=CC=CC=C1N=C1C=2C=CC=CC=2)=C1OS(=O)(=O)C1CC1 IVBLZTMRPBCUOW-QHCPKHFHSA-N 0.000 claims description 2
- AZNUQIWEPSDBGA-QFIPXVFZSA-N [2-phenyl-4-[[(1s)-1-phenylpropyl]carbamoyl]quinolin-3-yl] ethanesulfonate Chemical compound N([C@@H](CC)C=1C=CC=CC=1)C(=O)C(C1=CC=CC=C1N=1)=C(OS(=O)(=O)CC)C=1C1=CC=CC=C1 AZNUQIWEPSDBGA-QFIPXVFZSA-N 0.000 claims description 2
- FEKSXRXVEBQTRA-QHCPKHFHSA-N [2-phenyl-4-[[(1s)-1-phenylpropyl]carbamoyl]quinolin-3-yl] propane-1-sulfonate Chemical compound C1([C@H](CC)NC(=O)C2=C3C=CC=CC3=NC(=C2OS(=O)(=O)CCC)C=2C=CC=CC=2)=CC=CC=C1 FEKSXRXVEBQTRA-QHCPKHFHSA-N 0.000 claims description 2
- VRRJAJRQBMCIIO-FQEVSTJZSA-N [2-phenyl-4-[[(1s)-1-phenylpropyl]carbamoyl]quinolin-3-yl] trifluoromethanesulfonate Chemical compound N([C@@H](CC)C=1C=CC=CC=1)C(=O)C(C1=CC=CC=C1N=1)=C(OS(=O)(=O)C(F)(F)F)C=1C1=CC=CC=C1 VRRJAJRQBMCIIO-FQEVSTJZSA-N 0.000 claims description 2
- LVVHCWFNJMEOIH-UHFFFAOYSA-N [4-[1-(3-fluorophenyl)propylcarbamoyl]-2-phenylquinolin-3-yl] methanesulfonate Chemical compound C=1C=CC(F)=CC=1C(CC)NC(=O)C(C1=CC=CC=C1N=1)=C(OS(C)(=O)=O)C=1C1=CC=CC=C1 LVVHCWFNJMEOIH-UHFFFAOYSA-N 0.000 claims description 2
- LVVHCWFNJMEOIH-NRFANRHFSA-N [4-[[(1s)-1-(3-fluorophenyl)propyl]carbamoyl]-2-phenylquinolin-3-yl] methanesulfonate Chemical compound N([C@@H](CC)C=1C=C(F)C=CC=1)C(=O)C(C1=CC=CC=C1N=1)=C(OS(C)(=O)=O)C=1C1=CC=CC=C1 LVVHCWFNJMEOIH-NRFANRHFSA-N 0.000 claims description 2
- ILADJMBEWLGVNR-XMMPIXPASA-N [4-[[(s)-cyclopropyl(phenyl)methyl]carbamoyl]-2-(3-fluorophenyl)quinolin-3-yl] methanesulfonate Chemical compound C1([C@H](NC(=O)C2=C3C=CC=CC3=NC(=C2OS(=O)(=O)C)C=2C=C(F)C=CC=2)C=2C=CC=CC=2)CC1 ILADJMBEWLGVNR-XMMPIXPASA-N 0.000 claims description 2
- DDGMGRUSOBNKNR-XMMPIXPASA-N [4-[[(s)-cyclopropyl(phenyl)methyl]carbamoyl]-2-phenylquinolin-3-yl] methanesulfonate Chemical compound C1([C@H](NC(=O)C2=C3C=CC=CC3=NC(=C2OS(=O)(=O)C)C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 DDGMGRUSOBNKNR-XMMPIXPASA-N 0.000 claims description 2
- IOYGXJGJDLUJJE-DEOSSOPVSA-N [4-[[(s)-cyclopropyl-(3-fluorophenyl)methyl]carbamoyl]-2-(3-fluorophenyl)quinolin-3-yl] methanesulfonate Chemical compound C1([C@H](NC(=O)C2=C3C=CC=CC3=NC(=C2OS(=O)(=O)C)C=2C=C(F)C=CC=2)C=2C=C(F)C=CC=2)CC1 IOYGXJGJDLUJJE-DEOSSOPVSA-N 0.000 claims description 2
- ZKZLQRBJBGOWNI-DEOSSOPVSA-N [4-[[(s)-cyclopropyl-(3-fluorophenyl)methyl]carbamoyl]-2-phenylquinolin-3-yl] methanesulfonate Chemical compound C1([C@H](NC(=O)C2=C3C=CC=CC3=NC(=C2OS(=O)(=O)C)C=2C=CC=CC=2)C=2C=C(F)C=CC=2)CC1 ZKZLQRBJBGOWNI-DEOSSOPVSA-N 0.000 claims description 2
- ILADJMBEWLGVNR-UHFFFAOYSA-N [4-[[cyclopropyl(phenyl)methyl]carbamoyl]-2-(3-fluorophenyl)quinolin-3-yl] methanesulfonate Chemical compound CS(=O)(=O)OC1=C(C=2C=C(F)C=CC=2)N=C2C=CC=CC2=C1C(=O)NC(C=1C=CC=CC=1)C1CC1 ILADJMBEWLGVNR-UHFFFAOYSA-N 0.000 claims description 2
- DDGMGRUSOBNKNR-UHFFFAOYSA-N [4-[[cyclopropyl(phenyl)methyl]carbamoyl]-2-phenylquinolin-3-yl] methanesulfonate Chemical compound CS(=O)(=O)OC1=C(C=2C=CC=CC=2)N=C2C=CC=CC2=C1C(=O)NC(C=1C=CC=CC=1)C1CC1 DDGMGRUSOBNKNR-UHFFFAOYSA-N 0.000 claims description 2
- IOYGXJGJDLUJJE-UHFFFAOYSA-N [4-[[cyclopropyl-(3-fluorophenyl)methyl]carbamoyl]-2-(3-fluorophenyl)quinolin-3-yl] methanesulfonate Chemical compound CS(=O)(=O)OC1=C(C=2C=C(F)C=CC=2)N=C2C=CC=CC2=C1C(=O)NC(C=1C=C(F)C=CC=1)C1CC1 IOYGXJGJDLUJJE-UHFFFAOYSA-N 0.000 claims description 2
- ZKZLQRBJBGOWNI-UHFFFAOYSA-N [4-[[cyclopropyl-(3-fluorophenyl)methyl]carbamoyl]-2-phenylquinolin-3-yl] methanesulfonate Chemical compound CS(=O)(=O)OC1=C(C=2C=CC=CC=2)N=C2C=CC=CC2=C1C(=O)NC(C=1C=C(F)C=CC=1)C1CC1 ZKZLQRBJBGOWNI-UHFFFAOYSA-N 0.000 claims description 2
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- XOZKRDXYTIOWSL-QFIPXVFZSA-N n-[(1s)-2-cyano-1-phenylethyl]-2-phenylquinoline-4-carboxamide Chemical compound C1([C@H](CC#N)NC(=O)C=2C3=CC=CC=C3N=C(C=2)C=2C=CC=CC=2)=CC=CC=C1 XOZKRDXYTIOWSL-QFIPXVFZSA-N 0.000 description 1
- CTNHIQIYRHVMKJ-FQEVSTJZSA-N n-[(1s)-2-cyano-1-phenylethyl]-3-hydroxy-2-phenylquinoline-4-carboxamide Chemical compound C1([C@H](CC#N)NC(=O)C2=C3C=CC=CC3=NC(=C2O)C=2C=CC=CC=2)=CC=CC=C1 CTNHIQIYRHVMKJ-FQEVSTJZSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 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
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- XAPRFLSJBSXESP-UHFFFAOYSA-N oxycinchophen Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=C(O)C=1C1=CC=CC=C1 XAPRFLSJBSXESP-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000008019 pharmaceutical lubricant Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 1
- 229960003081 probenecid Drugs 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- RDZTWEVXRGYCFV-UHFFFAOYSA-M sodium 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonate Chemical compound [Na+].OCCN1CCN(CCS([O-])(=O)=O)CC1 RDZTWEVXRGYCFV-UHFFFAOYSA-M 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000003104 tissue culture media Substances 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
- C07D215/52—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
- A61P13/06—Anti-spasmodics
-
- 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
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Psychiatry (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Reproductive Health (AREA)
- Diabetes (AREA)
- Gynecology & Obstetrics (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Pregnancy & Childbirth (AREA)
- Child & Adolescent Psychology (AREA)
- Otolaryngology (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69328105P | 2005-06-23 | 2005-06-23 | |
| US60/693,281 | 2005-06-23 | ||
| PCT/SE2006/000758 WO2006137789A1 (en) | 2005-06-23 | 2006-06-21 | Quinoline 3 -sulfonate esters as NK3 receptor modulators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2613001A1 true CA2613001A1 (en) | 2006-12-28 |
Family
ID=37570727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002613001A Abandoned CA2613001A1 (en) | 2005-06-23 | 2006-06-21 | Quinoline 3 -sulfonate esters as nk3 receptor modulators |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20080194622A1 (https=) |
| EP (1) | EP1896418A1 (https=) |
| JP (1) | JP2008546767A (https=) |
| KR (1) | KR20080031871A (https=) |
| CN (1) | CN101208304A (https=) |
| AU (1) | AU2006259890A1 (https=) |
| CA (1) | CA2613001A1 (https=) |
| IL (1) | IL188034A0 (https=) |
| MX (1) | MX2007015607A (https=) |
| NO (1) | NO20080446L (https=) |
| WO (1) | WO2006137789A1 (https=) |
| ZA (1) | ZA200710723B (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR057130A1 (es) | 2005-09-21 | 2007-11-14 | Astrazeneca Ab | Quinolinas de alquilsulfoxido y una composicion farmaceutica |
| TW200804288A (en) | 2005-12-12 | 2008-01-16 | Astrazeneca Ab | Alkylsulphonamide quinolines |
| TW201016688A (en) * | 2008-10-20 | 2010-05-01 | Lundbeck & Co As H | Isoquinolinone derivatives as NK3 antagonists |
| US9624213B2 (en) | 2011-02-07 | 2017-04-18 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| WO2014170648A1 (en) | 2013-04-19 | 2014-10-23 | Astrazeneca Ab | A nk3 receptor antagonist compound (nk3ra) for use in a method for the treatment of polycystic ovary syndrome (pcos) |
| WO2017072629A1 (en) | 2015-10-29 | 2017-05-04 | Cadila Healthcare Limited | Pharmaceutical combination of nk3 receptor antagonist and biguanides |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SK282721B6 (sk) * | 1994-05-27 | 2002-11-06 | Smithkline Beecham S.P.A. | Nepeptidové NK3 antagonistické látky, spôsob ich výroby, farmaceutické prostriedky s ich obsahom a ich použitie |
| AR004735A1 (es) * | 1995-11-24 | 1999-03-10 | Smithkline Beecham Spa | Quinoleina 4-amido sustituida, un procedimiento para su preparacion, una composicion farmaceutica que los contiene y el uso de los mismos para lapreparacion de un medicamento. |
| GB0027701D0 (en) * | 2000-11-13 | 2000-12-27 | Smithkline Beecham Spa | Novel compounds |
| DE60209362T2 (de) * | 2001-04-11 | 2006-10-26 | Glaxosmithkline S.P.A. | 3-substituierte chinolin-4-carbonsäureamidderivate als nk-3- und nk-2-rezeptorantagonisten |
| GB0318727D0 (en) * | 2003-08-08 | 2003-09-10 | Smithkline Beecham Corp | Novel compounds |
-
2006
- 2006-06-21 JP JP2008518080A patent/JP2008546767A/ja not_active Abandoned
- 2006-06-21 CA CA002613001A patent/CA2613001A1/en not_active Abandoned
- 2006-06-21 KR KR1020077029959A patent/KR20080031871A/ko not_active Withdrawn
- 2006-06-21 US US11/917,820 patent/US20080194622A1/en not_active Abandoned
- 2006-06-21 AU AU2006259890A patent/AU2006259890A1/en not_active Abandoned
- 2006-06-21 WO PCT/SE2006/000758 patent/WO2006137789A1/en not_active Ceased
- 2006-06-21 EP EP06747947A patent/EP1896418A1/en not_active Withdrawn
- 2006-06-21 CN CNA2006800228098A patent/CN101208304A/zh active Pending
- 2006-06-21 MX MX2007015607A patent/MX2007015607A/es not_active Application Discontinuation
-
2007
- 2007-12-10 ZA ZA200710723A patent/ZA200710723B/xx unknown
- 2007-12-10 IL IL188034A patent/IL188034A0/en unknown
-
2008
- 2008-01-23 NO NO20080446A patent/NO20080446L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CN101208304A (zh) | 2008-06-25 |
| ZA200710723B (en) | 2008-12-31 |
| IL188034A0 (en) | 2008-03-20 |
| KR20080031871A (ko) | 2008-04-11 |
| MX2007015607A (es) | 2008-02-25 |
| AU2006259890A1 (en) | 2006-12-28 |
| NO20080446L (no) | 2008-01-23 |
| WO2006137789A1 (en) | 2006-12-28 |
| EP1896418A1 (en) | 2008-03-12 |
| JP2008546767A (ja) | 2008-12-25 |
| US20080194622A1 (en) | 2008-08-14 |
| WO2006137789A8 (en) | 2008-01-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 20100621 |