JP2008546767A5 - - Google Patents
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- Publication number
- JP2008546767A5 JP2008546767A5 JP2008518080A JP2008518080A JP2008546767A5 JP 2008546767 A5 JP2008546767 A5 JP 2008546767A5 JP 2008518080 A JP2008518080 A JP 2008518080A JP 2008518080 A JP2008518080 A JP 2008518080A JP 2008546767 A5 JP2008546767 A5 JP 2008546767A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- alkyl
- cycloalkyl
- alkoxy
- ester
- 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
- 125000000217 alkyl group Chemical group 0.000 claims 61
- 125000004093 cyano group Chemical group *C#N 0.000 claims 28
- 125000003545 alkoxy group Chemical group 0.000 claims 26
- 229910052736 halogen Inorganic materials 0.000 claims 26
- 150000002367 halogens Chemical class 0.000 claims 26
- 125000003118 aryl group Chemical group 0.000 claims 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
- 125000005842 heteroatom Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 229910052717 sulfur Inorganic materials 0.000 claims 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 8
- 125000003342 alkenyl group Chemical group 0.000 claims 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 8
- 125000001624 naphthyl group Chemical group 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 239000001301 oxygen Substances 0.000 claims 8
- 239000011593 sulfur Chemical group 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 7
- 238000001727 in vivo Methods 0.000 claims 7
- 239000002243 precursor Substances 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 4
- 125000002837 carbocyclic group Chemical group 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 125000004434 sulfur atom Chemical group 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 208000005171 Dysmenorrhea Diseases 0.000 claims 1
- 206010013935 Dysmenorrhoea Diseases 0.000 claims 1
- 102000006771 Gonadotropins Human genes 0.000 claims 1
- 108010086677 Gonadotropins Proteins 0.000 claims 1
- 101001125071 Homo sapiens Neuromedin-K receptor Proteins 0.000 claims 1
- 102100029409 Neuromedin-K receptor Human genes 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 208000024313 Testicular Neoplasms Diseases 0.000 claims 1
- 206010057644 Testis cancer Diseases 0.000 claims 1
- 206010047700 Vomiting Diseases 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000003098 androgen Substances 0.000 claims 1
- 229940030486 androgens Drugs 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 239000002622 gonadotropin Substances 0.000 claims 1
- 229940094892 gonadotropins Drugs 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- 239000000314 lubricant Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 201000011461 pre-eclampsia Diseases 0.000 claims 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical class OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- -1 sulfonate ester Chemical class 0.000 claims 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 1
- 201000003120 testicular cancer Diseases 0.000 claims 1
- 230000008673 vomiting Effects 0.000 claims 1
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 JP2008546767A (ja) | 2008-12-25 |
| JP2008546767A5 true JP2008546767A5 (https=) | 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 (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
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