ZA200601552B - Imidazopyridine-derivatives as inducible no-synthase inhibitors - Google Patents

Imidazopyridine-derivatives as inducible no-synthase inhibitors Download PDF

Info

Publication number: ZA200601552B
Authority: ZA; South Africa
Prior art keywords: compounds; pyridin; oxides; salts; alkyl
Prior art date: 2003-10-01

Application number

ZA200601552A

Other languages

English (en)

Inventor

Fuchss Thomas

Boer Rainer

Eltze Manfrid

Marx Degenhard

Martin Thomas

Strub Andreas

Lehner Martin

Ulrich Wolf-Ruediger

Original Assignee

Altana Pharma Ag

Priority date (The priority date 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 date listed.)

2003-10-01

Filing date

2006-02-22

Publication date

2007-04-25

2006-02-22 Application filed by Altana Pharma Ag filed Critical Altana Pharma Ag

2007-04-25 Publication of ZA200601552B publication Critical patent/ZA200601552B/en

Links

102100029438 Nitric oxide synthase, inducible Human genes 0.000 title abstract description 3
101710089543 Nitric oxide synthase, inducible Proteins 0.000 title abstract description 3
239000003112 inhibitor Substances 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 109
-1 1-4C-alkylcarbonyl Chemical group 0.000 claims description 127
150000003839 salts Chemical class 0.000 claims description 72
150000001204 N-oxides Chemical class 0.000 claims description 63
229910052736 halogen Inorganic materials 0.000 claims description 41
150000002367 halogens Chemical group 0.000 claims description 41
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 36
229910052739 hydrogen Inorganic materials 0.000 claims description 33
239000001257 hydrogen Substances 0.000 claims description 33
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 30
239000005977 Ethylene Substances 0.000 claims description 30
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 30
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
239000000460 chlorine Chemical group 0.000 claims description 21
229910052801 chlorine Inorganic materials 0.000 claims description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
229910052757 nitrogen Inorganic materials 0.000 claims description 17
125000004076 pyridyl group Chemical group 0.000 claims description 17
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
125000005842 heteroatom Chemical group 0.000 claims description 16
229910052760 oxygen Inorganic materials 0.000 claims description 16
239000001301 oxygen Substances 0.000 claims description 16
239000011593 sulfur Substances 0.000 claims description 16
229910052717 sulfur Inorganic materials 0.000 claims description 16
125000004093 cyano group Chemical group *C#N 0.000 claims description 15
125000002619 bicyclic group Chemical group 0.000 claims description 14
125000001041 indolyl group Chemical group 0.000 claims description 14
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 13
125000002950 monocyclic group Chemical group 0.000 claims description 13
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 4
125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
208000027866 inflammatory disease Diseases 0.000 claims 2
208000031229 Cardiomyopathies Diseases 0.000 claims 1
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
102000004127 Cytokines Human genes 0.000 claims 1
108090000695 Cytokines Proteins 0.000 claims 1
208000032456 Hemorrhagic Shock Diseases 0.000 claims 1
208000009525 Myocarditis Diseases 0.000 claims 1
206010040047 Sepsis Diseases 0.000 claims 1
206010040070 Septic Shock Diseases 0.000 claims 1
206010049771 Shock haemorrhagic Diseases 0.000 claims 1
230000001154 acute effect Effects 0.000 claims 1
208000006673 asthma Diseases 0.000 claims 1
125000004532 benzofuran-3-yl group Chemical group O1C=C(C2=C1C=CC=C2)* 0.000 claims 1
208000037976 chronic inflammation Diseases 0.000 claims 1
208000037893 chronic inflammatory disorder Diseases 0.000 claims 1
201000010099 disease Diseases 0.000 claims 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
208000019622 heart disease Diseases 0.000 claims 1
210000004072 lung Anatomy 0.000 claims 1
210000000056 organ Anatomy 0.000 claims 1
230000002093 peripheral effect Effects 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
230000036303 septic shock Effects 0.000 claims 1
230000035939 shock Effects 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
125000001072 heteroaryl group Chemical group 0.000 description 13
125000005493 quinolyl group Chemical group 0.000 description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
229910052731 fluorine Inorganic materials 0.000 description 6
239000011737 fluorine Substances 0.000 description 6
150000002431 hydrogen Chemical group 0.000 description 6
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
125000002541 furyl group Chemical group 0.000 description 4
125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 3
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 3
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
238000006243 chemical reaction Methods 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
125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 3
125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
125000005956 isoquinolyl group Chemical group 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
125000001544 thienyl group Chemical group 0.000 description 3
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-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
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
125000005620 boronic acid group Chemical class 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
125000001309 chloro group Chemical group Cl* 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
150000004677 hydrates Chemical class 0.000 description 2
125000002883 imidazolyl group Chemical group 0.000 description 2
150000005232 imidazopyridines Chemical class 0.000 description 2
125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 2
125000004552 isoquinolin-4-yl group Chemical group C1=NC=C(C2=CC=CC=C12)* 0.000 description 2
238000000034 method Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 2
125000000714 pyrimidinyl group Chemical group 0.000 description 2
125000000168 pyrrolyl group Chemical group 0.000 description 2
125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 description 2
125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000012453 solvate Substances 0.000 description 2
238000006467 substitution reaction Methods 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
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
YGTUPRIZNBMOFV-UHFFFAOYSA-N 2-(4-hydroxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(O)C=C1 YGTUPRIZNBMOFV-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
ZHHLLWPSTIDRGT-UHFFFAOYSA-N 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-pyridin-3-yl-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=NC=CC=2)=C1 ZHHLLWPSTIDRGT-UHFFFAOYSA-N 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-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
150000005240 3H-imidazo[4,5-b]pyridines Chemical class 0.000 description 1
YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 1
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-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
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical class NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
IVDFJHOHABJVEH-UHFFFAOYSA-N HOCMe2CMe2OH Natural products CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 1
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 1
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
239000005639 Lauric acid Substances 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
238000006069 Suzuki reaction reaction Methods 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
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000000767 anti-ulcer Effects 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
150000001642 boronic acid derivatives Chemical class 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
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
235000015165 citric acid Nutrition 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
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
229950006191 gluconic acid Drugs 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 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
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960003194 meglumine Drugs 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910017604 nitric acid Inorganic materials 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
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
150000007519 polyprotic acids Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 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
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- 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
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ZA200601552A 2003-10-01 2006-02-22 Imidazopyridine-derivatives as inducible no-synthase inhibitors ZA200601552B (en)

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Application Number	Priority Date	Filing Date	Title
EP03022064		2003-10-01

Publications (1)

Publication Number	Publication Date
ZA200601552B true ZA200601552B (en)	2007-04-25

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Application Number	Title	Priority Date	Filing Date
ZA200601552A ZA200601552B (en)	2003-10-01	2006-02-22	Imidazopyridine-derivatives as inducible no-synthase inhibitors

Country Status (17)

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US (1)	US20080125460A1 (ru)
EP (1)	EP1673371B1 (ru)
JP (1)	JP2007507465A (ru)
KR (1)	KR20060092222A (ru)
CN (1)	CN1856494A (ru)
AT (1)	ATE403655T1 (ru)
AU (1)	AU2004276013A1 (ru)
BR (1)	BRPI0414873A (ru)
CA (1)	CA2540242A1 (ru)
DE (1)	DE602004015628D1 (ru)
EA (1)	EA200600609A1 (ru)
IL (1)	IL173809A0 (ru)
MX (1)	MXPA06003554A (ru)
NO (1)	NO20061316L (ru)
RS (1)	RS20060195A (ru)
WO (1)	WO2005030769A1 (ru)
ZA (1)	ZA200601552B (ru)

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* Cited by examiner, † Cited by third party
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ES2308260T3 (es)	2003-10-01	2008-12-01	Nycomed Gmbh	Derivados de imidazopiridinas como inhibidores de no-sintasa inducible.
RS20060206A (en)	2003-10-01	2008-08-07	Altana Pharma Ag.,	Aminopyridine-derivatives as inducible no-synthase inhibitors
BRPI0414972A (pt)	2003-10-01	2006-11-07	Altana Pharma Ag	derivados de imidazopiridinas como inibidores de no-sintase induzìvel
AU2004276012A1 (en)	2003-10-01	2005-04-07	Altana Pharma Ag	Imidazo(4,5-b)pyridine-derivatives as inducible no-synthase inhibitors
WO2009029625A1 (en) *	2007-08-27	2009-03-05	Kalypsys, Inc.	4- [heterocyclyl-methyl] -8-fluoro-quinolin-2-ones useful as nitric oxide synthase inhibitors
CN103038229B (zh) *	2010-05-26	2016-05-11	桑诺维恩药品公司	杂芳基化合物及其使用方法
US9670230B2 (en) *	2012-11-29	2017-06-06	Sunovion Pharmaceuticals Inc.	Heteroaryl compounds and methods of use thereof
GB201512635D0 (en)	2015-07-17	2015-08-26	Ucl Business Plc	Uses of therapeutic compounds

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US4045564A (en) *	1974-02-18	1977-08-30	Ab Hassle	Benzimidazole derivatives useful as gastric acid secretion inhibitors
SE418966B (sv) *	1974-02-18	1981-07-06	Haessle Ab	Analogiforfarande for framstellning av foreningar med magsyrasekretionsinhiberande verkan
GB8307865D0 (en) *	1983-03-22	1983-04-27	Fujisawa Pharmaceutical Co	Benzimidazole derivatives
AUPP873799A0 (en) *	1999-02-17	1999-03-11	Fujisawa Pharmaceutical Co., Ltd.	Pyridine compounds
MXPA04009283A (es) *	2002-03-27	2005-01-25	Altana Pharma Ag	Nuevos derivados de alcoxipiridina.

2004
- 2004-09-30 AU AU2004276013A patent/AU2004276013A1/en not_active Abandoned
- 2004-09-30 DE DE602004015628T patent/DE602004015628D1/de not_active Expired - Fee Related
- 2004-09-30 AT AT04787261T patent/ATE403655T1/de not_active IP Right Cessation
- 2004-09-30 BR BRPI0414873-8A patent/BRPI0414873A/pt not_active IP Right Cessation
- 2004-09-30 MX MXPA06003554A patent/MXPA06003554A/es not_active Application Discontinuation
- 2004-09-30 EA EA200600609A patent/EA200600609A1/ru unknown
- 2004-09-30 CN CNA2004800278191A patent/CN1856494A/zh active Pending
- 2004-09-30 EP EP04787261A patent/EP1673371B1/en active Active
- 2004-09-30 CA CA002540242A patent/CA2540242A1/en not_active Abandoned
- 2004-09-30 US US10/573,525 patent/US20080125460A1/en not_active Abandoned
- 2004-09-30 JP JP2006530262A patent/JP2007507465A/ja not_active Withdrawn
- 2004-09-30 RS YUP-2006/0195A patent/RS20060195A/sr unknown
- 2004-09-30 KR KR1020067005900A patent/KR20060092222A/ko not_active Application Discontinuation
- 2004-09-30 WO PCT/EP2004/052376 patent/WO2005030769A1/en active IP Right Grant
2006
- 2006-02-19 IL IL173809A patent/IL173809A0/en unknown
- 2006-02-22 ZA ZA200601552A patent/ZA200601552B/en unknown
- 2006-03-23 NO NO20061316A patent/NO20061316L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
NO20061316L (no)	2006-03-23
ATE403655T1 (de)	2008-08-15
IL173809A0 (en)	2006-07-05
CN1856494A (zh)	2006-11-01
BRPI0414873A (pt)	2006-12-12
EP1673371A1 (en)	2006-06-28
AU2004276013A1 (en)	2005-04-07
RS20060195A (en)	2008-08-07
DE602004015628D1 (de)	2008-09-18
US20080125460A1 (en)	2008-05-29
WO2005030769A1 (en)	2005-04-07
JP2007507465A (ja)	2007-03-29
EP1673371B1 (en)	2008-08-06
MXPA06003554A (es)	2006-06-05
EA200600609A1 (ru)	2006-10-27
KR20060092222A (ko)	2006-08-22
CA2540242A1 (en)	2005-04-07

Publication	Publication Date	Title
ZA200601552B (en)	2007-04-25	Imidazopyridine-derivatives as inducible no-synthase inhibitors
AU2002230618B2 (en)	2006-11-02	Heterocyclic ether substituted imidazoquinolines
AU2003252011B2 (en)	2007-11-22	Substituted 2-alkylamine nicotinic amide derivatives and use there of
TW202309025A (zh)	2023-03-01	Parp1抑制劑及其用途
JP2020147575A (ja)	2020-09-17	治療用阻害化合物
TWI460177B (zh)	2014-11-11	An azabicyclo compound or a salt thereof
JP6151919B2 (ja)	2017-06-21	ヘタリールアミノナフチリジン
JP2018505207A (ja)	2018-02-22	置換モノおよびポリアザナフタレン誘導体およびその使用
MX2013000617A (es)	2013-06-13	Derivados sustituidos de imidazoquinolina como inhibidores de quinasa.
JP2006502164A5 (ru)	2006-10-19
JP2006502164A (ja)	2006-01-19	イミダゾロピリジンならびにその生成および使用方法
EP4304720A1 (en)	2024-01-17	Mta-cooperative prmt5 inhibitors
AU2002230618A1 (en)	2002-08-22	Heterocyclic ether substituted imidazoquinolines
JP2013536193A (ja)	2013-09-19	ヘテロアリール類およびその使用
OA12428A (en)	2006-04-19	Quinolinone derivatives as tyrosine kinase inhibitors.
KR20080026654A (ko)	2008-03-25	헤테로시클릭 야누스 키나제 3 억제제
NZ569815A (en)	2011-11-25	Aurora kinase modulators and method of use
JP2009511439A (ja)	2009-03-19	タンパク質キナーゼ阻害剤としてのチエノ［２，３−ｂ］ピリジン−５−カルボニトリル
TW201018682A (en)	2010-05-16	Heterocyclic biaryl derivative, and pde inhibitor comprising same as active ingredient
US7790710B2 (en)	2010-09-07	Imidazopyridine derivatives useful as iNOS inhibitors