JP2008546767A - Ｎｋ３受容体のモジュレーターとしてのキノリン３−スルホン酸エステル - Google Patents
Ｎｋ３受容体のモジュレーターとしてのキノリン３−スルホン酸エステル Download PDFInfo
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- JP2008546767A JP2008546767A JP2008518080A JP2008518080A JP2008546767A JP 2008546767 A JP2008546767 A JP 2008546767A JP 2008518080 A JP2008518080 A JP 2008518080A JP 2008518080 A JP2008518080 A JP 2008518080A JP 2008546767 A JP2008546767 A JP 2008546767A
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- Prior art keywords
- alkyl
- phenyl
- cycloalkyl
- alkoxy
- 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
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- 102100029409 Neuromedin-K receptor Human genes 0.000 title claims description 30
- 101001125071 Homo sapiens Neuromedin-K receptor Proteins 0.000 title claims description 14
- ITXXHPLNLYEVQT-UHFFFAOYSA-N quinoline-3-sulfonic acid Chemical compound 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
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 32
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 124
- 125000003545 alkoxy group Chemical group 0.000 claims description 56
- 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 55
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000005842 heteroatom Chemical group 0.000 claims description 24
- 125000004433 nitrogen atom Chemical group N* 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
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 201000010099 disease Diseases 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 16
- 238000001727 in vivo Methods 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 16
- 239000002243 precursor Substances 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- 208000035475 disorder Diseases 0.000 claims description 14
- 239000011593 sulfur Chemical group 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 208000008589 Obesity Diseases 0.000 claims description 11
- 235000020824 obesity Nutrition 0.000 claims description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- 208000019901 Anxiety disease Diseases 0.000 claims description 10
- 230000036506 anxiety Effects 0.000 claims description 10
- 201000000980 schizophrenia Diseases 0.000 claims description 10
- 125000004434 sulfur atom Chemical group 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
- 208000028698 Cognitive impairment Diseases 0.000 claims description 8
- 108010086677 Gonadotropins Proteins 0.000 claims description 8
- 102000006771 Gonadotropins Human genes 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
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 239000003098 androgen Substances 0.000 claims description 8
- 125000002837 carbocyclic group Chemical group 0.000 claims description 8
- 208000010877 cognitive disease Diseases 0.000 claims description 8
- 239000002622 gonadotropin Substances 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
- 201000003120 testicular cancer Diseases 0.000 claims description 8
- 230000008673 vomiting Effects 0.000 claims description 8
- 208000005171 Dysmenorrhea Diseases 0.000 claims description 7
- 206010013935 Dysmenorrhoea Diseases 0.000 claims description 7
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 7
- 230000009286 beneficial effect Effects 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 229940094892 gonadotropins Drugs 0.000 claims description 7
- -1 sulfonate ester Chemical class 0.000 claims description 7
- 229940030486 androgens Drugs 0.000 claims description 6
- 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
- 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
- 239000000460 chlorine Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000000314 lubricant Substances 0.000 claims description 3
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical class OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 claims description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 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
- DTCHSUWUAMDDQE-NRFANRHFSA-N [2-(3-fluorophenyl)-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(F)=C1 DTCHSUWUAMDDQE-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
- BLWLOUSTXZIEHT-UHFFFAOYSA-N [2-phenyl-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=C1 BLWLOUSTXZIEHT-UHFFFAOYSA-N 0.000 claims description 2
- FEKSXRXVEBQTRA-UHFFFAOYSA-N [2-phenyl-4-(1-phenylpropylcarbamoyl)quinolin-3-yl] propane-1-sulfonate Chemical compound CCCS(=O)(=O)OC1=C(C=2C=CC=CC=2)N=C2C=CC=CC2=C1C(=O)NC(CC)C1=CC=CC=C1 FEKSXRXVEBQTRA-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
- 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 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
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- 231100001231 less toxic Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007762 localization of cell Effects 0.000 description 1
- 238000000464 low-speed centrifugation Methods 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000005906 menstruation Effects 0.000 description 1
- 108020004999 messenger RNA Proteins 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-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
- MZQVNJVHTPLBCU-QHCPKHFHSA-N n-[(s)-cyclopropyl-(3-fluorophenyl)methyl]-3-hydroxy-2-phenylquinoline-4-carboxamide Chemical compound C1([C@H](NC(=O)C2=C3C=CC=CC3=NC(=C2O)C=2C=CC=CC=2)C=2C=C(F)C=CC=2)CC1 MZQVNJVHTPLBCU-QHCPKHFHSA-N 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 210000002569 neuron Anatomy 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
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-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
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960004838 phosphoric acid Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 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
- 230000012121 regulation of immune response Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 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
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- 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
- 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
- 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
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- 210000005166 vasculature Anatomy 0.000 description 1
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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
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- 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
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- 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
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- 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
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- 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
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- 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
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- 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]
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Hospice & Palliative Care (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Otolaryngology (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Child & Adolescent Psychology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69328105P | 2005-06-23 | 2005-06-23 | |
| PCT/SE2006/000758 WO2006137789A1 (en) | 2005-06-23 | 2006-06-21 | Quinoline 3 -sulfonate esters as NK3 receptor modulators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008546767A true JP2008546767A (ja) | 2008-12-25 |
| JP2008546767A5 JP2008546767A5 (enExample) | 2009-06-25 |
Family
ID=37570727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008518080A Abandoned JP2008546767A (ja) | 2005-06-23 | 2006-06-21 | Ｎｋ３受容体のモジュレーターとしてのキノリン３−スルホン酸エステル |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20080194622A1 (enExample) |
| EP (1) | EP1896418A1 (enExample) |
| JP (1) | JP2008546767A (enExample) |
| KR (1) | KR20080031871A (enExample) |
| CN (1) | CN101208304A (enExample) |
| AU (1) | AU2006259890A1 (enExample) |
| CA (1) | CA2613001A1 (enExample) |
| IL (1) | IL188034A0 (enExample) |
| MX (1) | MX2007015607A (enExample) |
| NO (1) | NO20080446L (enExample) |
| WO (1) | WO2006137789A1 (enExample) |
| ZA (1) | ZA200710723B (enExample) |
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 |
| TW201018662A (en) | 2005-12-12 | 2010-05-16 | Astrazeneca Ab | Alkylsulphonamide quinolines |
| AR073891A1 (es) * | 2008-10-20 | 2010-12-09 | Lundbeck & Co As H | Derivados de isoquinolinona antagonistas de receptores nk3, composiciones farmaceuticas que los contienen y uso de los mismos en el tratamiento de psicosis, alzheimer y otras enfermedades. |
| PE20141360A1 (es) | 2011-02-07 | 2014-10-13 | Plexxikon Inc | Compuestos y metodos para la modulacion de quinasas e indicaciones para los mismos. |
| BR112015026519A2 (pt) | 2013-04-19 | 2017-07-25 | Astrazeneca Ab | composto antagonista do receptor nk3 (nk3ra) para uso em um método destinado ao tratamento de síndrome do ovário policístico (sop) |
| 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 |
|---|---|---|---|---|
| DE69531458T2 (de) * | 1994-05-27 | 2004-08-05 | Glaxosmithkline S.P.A. | Chinolinderivate als tachykinin nk3 rezeptor antagonisten |
| 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 |
| EP1385839B1 (en) * | 2001-04-11 | 2006-02-22 | GlaxoSmithKline S.p.A. | 3-substituted quinoline-4-carboxamide derivatives as nk-3 and nk-2 receptor antagonists |
| GB0318727D0 (en) * | 2003-08-08 | 2003-09-10 | Smithkline Beecham Corp | Novel compounds |
-
2006
- 2006-06-21 WO PCT/SE2006/000758 patent/WO2006137789A1/en not_active Ceased
- 2006-06-21 AU AU2006259890A patent/AU2006259890A1/en not_active Abandoned
- 2006-06-21 JP JP2008518080A patent/JP2008546767A/ja not_active Abandoned
- 2006-06-21 CN CNA2006800228098A patent/CN101208304A/zh active Pending
- 2006-06-21 EP EP06747947A patent/EP1896418A1/en not_active Withdrawn
- 2006-06-21 CA CA002613001A patent/CA2613001A1/en not_active Abandoned
- 2006-06-21 US US11/917,820 patent/US20080194622A1/en not_active Abandoned
- 2006-06-21 KR KR1020077029959A patent/KR20080031871A/ko not_active Withdrawn
- 2006-06-21 MX MX2007015607A patent/MX2007015607A/es not_active Application Discontinuation
-
2007
- 2007-12-10 IL IL188034A patent/IL188034A0/en unknown
- 2007-12-10 ZA ZA200710723A patent/ZA200710723B/xx unknown
-
2008
- 2008-01-23 NO NO20080446A patent/NO20080446L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2006259890A1 (en) | 2006-12-28 |
| WO2006137789A8 (en) | 2008-01-17 |
| KR20080031871A (ko) | 2008-04-11 |
| CN101208304A (zh) | 2008-06-25 |
| US20080194622A1 (en) | 2008-08-14 |
| CA2613001A1 (en) | 2006-12-28 |
| MX2007015607A (es) | 2008-02-25 |
| IL188034A0 (en) | 2008-03-20 |
| NO20080446L (no) | 2008-01-23 |
| ZA200710723B (en) | 2008-12-31 |
| WO2006137789A1 (en) | 2006-12-28 |
| EP1896418A1 (en) | 2008-03-12 |
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