ZA200200028B - Imidazo[1,2-A]pyridine and pyrazolo[2,3-A]pyridine devatives. - Google Patents

Imidazo[1,2-A]pyridine and pyrazolo[2,3-A]pyridine devatives. Download PDF

Info

Publication number: ZA200200028B
Authority: ZA; South Africa
Prior art keywords: sulphamoyl; formula; compound; carbamoyl; salkyl
Prior art date: 1999-08-21

Application number

ZA200200028A

Other languages

English (en)

Inventor

Andrew Peter Thomas

Gloria Anne Breault

John Franklin Beattie

Phillip John Jewsbury

Original Assignee

Astrazeneca Ab

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.)

1999-08-21

Filing date

2002-01-02

Publication date

2003-04-02

2002-01-02 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2003-04-02 Publication of ZA200200028B publication Critical patent/ZA200200028B/en

Links

DVUBDHRTVYLIPA-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine Chemical compound C1=CC=CN2N=CC=C21 DVUBDHRTVYLIPA-UHFFFAOYSA-N 0.000 title description 2
UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 title 1
-1 cyano, hydroxy Chemical group 0.000 claims description 161
125000000217 alkyl group Chemical group 0.000 claims description 48
150000001875 compounds Chemical class 0.000 claims description 40
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 34
125000000623 heterocyclic group Chemical group 0.000 claims description 31
150000002148 esters Chemical class 0.000 claims description 29
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 28
229910052799 carbon Inorganic materials 0.000 claims description 28
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
150000003839 salts Chemical class 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 23
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 22
238000001727 in vivo Methods 0.000 claims description 22
229910052757 nitrogen Inorganic materials 0.000 claims description 21
125000005843 halogen group Chemical group 0.000 claims description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
125000003342 alkenyl group Chemical group 0.000 claims description 12
238000000034 method Methods 0.000 claims description 10
206010028980 Neoplasm Diseases 0.000 claims description 9
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
241001465754 Metazoa Species 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 5
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000001589 carboacyl group Chemical group 0.000 claims description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
230000035755 proliferation Effects 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
206010051113 Arterial restenosis Diseases 0.000 claims description 3
201000001320 Atherosclerosis Diseases 0.000 claims description 3
208000023275 Autoimmune disease Diseases 0.000 claims description 3
208000020084 Bone disease Diseases 0.000 claims description 3
208000022873 Ocular disease Diseases 0.000 claims description 3
201000004681 Psoriasis Diseases 0.000 claims description 3
230000001154 acute effect Effects 0.000 claims description 3
208000038016 acute inflammation Diseases 0.000 claims description 3
230000006022 acute inflammation Effects 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 3
230000001684 chronic effect Effects 0.000 claims description 3
208000037976 chronic inflammation Diseases 0.000 claims description 3
230000006020 chronic inflammation Effects 0.000 claims description 3
208000035475 disorder Diseases 0.000 claims description 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
230000000893 fibroproliferative effect Effects 0.000 claims description 3
201000011066 hemangioma Diseases 0.000 claims description 3
208000017169 kidney disease Diseases 0.000 claims description 3
208000032839 leukemia Diseases 0.000 claims description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
125000004043 oxo group Chemical group O=* 0.000 claims description 3
206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
208000007766 Kaposi sarcoma Diseases 0.000 claims description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 10
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 7
239000000203 mixture Substances 0.000 claims 7
239000000126 substance Substances 0.000 claims 5
210000001210 retinal vessel Anatomy 0.000 claims 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
NKORVPQBJCGYEC-UHFFFAOYSA-N 4-[(4-imidazo[1,2-a]pyridin-3-ylpyrimidin-2-yl)amino]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC1=NC=CC(C=2N3C=CC=CC3=NC=2)=N1 NKORVPQBJCGYEC-UHFFFAOYSA-N 0.000 claims 1
206010003210 Arteriosclerosis Diseases 0.000 claims 1
208000037260 Atherosclerotic Plaque Diseases 0.000 claims 1
206010039491 Sarcoma Diseases 0.000 claims 1
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
150000001412 amines Chemical class 0.000 claims 1
239000003153 chemical reaction reagent Substances 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
125000006239 protecting group Chemical group 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
108091007914 CDKs Proteins 0.000 description 8
230000022131 cell cycle Effects 0.000 description 8
230000000694 effects Effects 0.000 description 6
239000011575 calcium Substances 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
102000016736 Cyclin Human genes 0.000 description 4
108050006400 Cyclin Proteins 0.000 description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
125000005236 alkanoylamino group Chemical group 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 description 3
108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 description 3
102100036239 Cyclin-dependent kinase 2 Human genes 0.000 description 3
102100036252 Cyclin-dependent kinase 4 Human genes 0.000 description 3
125000004423 acyloxy group Chemical group 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
150000003230 pyrimidines Chemical class 0.000 description 3
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
150000001204 N-oxides Chemical class 0.000 description 2
108700020796 Oncogene Proteins 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
239000005864 Sulphur Substances 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
125000002619 bicyclic group Chemical group 0.000 description 2
230000004663 cell proliferation Effects 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
125000002950 monocyclic group Chemical group 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
229940002612 prodrug Drugs 0.000 description 2
239000000651 prodrug Substances 0.000 description 2
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 2
230000019491 signal transduction Effects 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
125000005871 1,3-benzodioxolyl group Chemical group 0.000 description 1
NOLHRFLIXVQPSZ-UHFFFAOYSA-N 1,3-thiazolidin-4-one Chemical compound O=C1CSCN1 NOLHRFLIXVQPSZ-UHFFFAOYSA-N 0.000 description 1
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000006017 1-propenyl group Chemical group 0.000 description 1
125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 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
GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 description 1
PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
108010025468 Cyclin-Dependent Kinase 6 Proteins 0.000 description 1
102100032857 Cyclin-dependent kinase 1 Human genes 0.000 description 1
101710106279 Cyclin-dependent kinase 1 Proteins 0.000 description 1
102100026804 Cyclin-dependent kinase 6 Human genes 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
108091000080 Phosphotransferase Proteins 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
102000001253 Protein Kinase Human genes 0.000 description 1
GIIWGCBLYNDKBO-UHFFFAOYSA-N Quinoline 1-oxide Chemical compound C1=CC=C2[N+]([O-])=CC=CC2=C1 GIIWGCBLYNDKBO-UHFFFAOYSA-N 0.000 description 1
230000018199 S phase Effects 0.000 description 1
229940124639 Selective inhibitor Drugs 0.000 description 1
102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
108700025695 Suppressor Genes Proteins 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
230000001594 aberrant effect Effects 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000001093 anti-cancer Effects 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
125000001721 carboxyacetyl group Chemical group 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
230000026374 cyclin catabolic process Effects 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
238000012217 deletion Methods 0.000 description 1
230000037430 deletion Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
125000005117 dialkylcarbamoyl group Chemical group 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
201000010099 disease Diseases 0.000 description 1
125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
150000002485 inorganic esters Chemical class 0.000 description 1
230000003834 intracellular effect Effects 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical compound C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
159000000003 magnesium salts Chemical class 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
125000006626 methoxycarbonylamino group Chemical group 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 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
230000002297 mitogenic effect Effects 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
102000020233 phosphotransferase Human genes 0.000 description 1
125000005633 phthalidyl group Chemical group 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
108060006633 protein kinase Proteins 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000001422 pyrrolinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
230000002207 retinal effect Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000005505 thiomorpholino group Chemical group 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
230000003827 upregulation Effects 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 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
- 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
- A61P13/00—Drugs for disorders of the urinary system
- 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
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A—HUMAN NECESSITIES
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ZA200200028A 1999-08-21 2002-01-02 Imidazo[1,2-A]pyridine and pyrazolo[2,3-A]pyridine devatives. ZA200200028B (en)

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GBGB9919778.2A GB9919778D0 (en)	1999-08-21	1999-08-21	Chemical compounds

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CN (1)	CN1174981C (de)
AR (1)	AR031075A1 (de)
AT (1)	ATE251623T1 (de)
AU (1)	AU757639B2 (de)
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Publication number	Publication date
CN1370163A (zh)	2002-09-18
DE60005850T2 (de)	2005-03-24
ATE251623T1 (de)	2003-10-15
EE200200080A (et)	2003-06-16
EP1214318B1 (de)	2003-10-08
CN1174981C (zh)	2004-11-10
PL199615B1 (pl)	2008-10-31
KR20020021411A (ko)	2002-03-20
MY123390A (en)	2006-05-31
SK287033B6 (sk)	2009-10-07
DE60005850D1 (de)	2003-11-13
JP2003507478A (ja)	2003-02-25
WO2001014375A1 (en)	2001-03-01
AU6583300A (en)	2001-03-19
US6855719B1 (en)	2005-02-15
GB9919778D0 (en)	1999-10-27
ES2208397T3 (es)	2004-06-16
HK1045510A1 (en)	2002-11-29
EP1214318A1 (de)	2002-06-19
IL147752A (en)	2006-06-11
PL364722A1 (en)	2004-12-13
MXPA02001674A (es)	2002-08-06
NO20020832D0 (no)	2002-02-20
IS6274A (is)	2002-02-15
NO20020832L (no)	2002-04-12
IL147752A0 (en)	2002-08-14
KR100737259B1 (ko)	2007-07-10
PT1214318E (pt)	2004-02-27
BG106383A (en)	2002-09-30
CO5460265A1 (es)	2004-11-30
NO322818B1 (no)	2006-12-11
BG65566B1 (bg)	2008-12-30
RU2248976C2 (ru)	2005-03-27
SK2402002A3 (en)	2002-09-10
IS2068B (is)	2005-11-15
UA73522C2 (en)	2005-08-15
JP4280442B2 (ja)	2009-06-17
HUP0202494A2 (en)	2002-10-28
CZ2002617A3 (cs)	2002-06-12
HUP0202494A3 (en)	2003-10-28
DK1214318T3 (da)	2004-02-09
CA2376293A1 (en)	2001-03-01
BR0013476A (pt)	2002-04-30
NZ516740A (en)	2004-09-24
HK1045510B (en)	2004-03-19
EE04964B1 (et)	2008-02-15
AR031075A1 (es)	2003-09-10
AU757639B2 (en)	2003-02-27

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