NO322818B1 - Imidazo(1,2-A)pyridin og pyrazolo(2,3-A)pyridin derivater, anvendelse og fremstilling derav, samt farmasoytisk preparat. - Google Patents

Imidazo(1,2-A)pyridin og pyrazolo(2,3-A)pyridin derivater, anvendelse og fremstilling derav, samt farmasoytisk preparat. Download PDF

Info

Publication number: NO322818B1
Authority: NO; Norway
Prior art keywords: sulfamoyl; formula; alkyl; compound; pharmaceutically acceptable
Prior art date: 1999-08-21

Application number

NO20020832A

Other languages

English (en)

Norwegian (no)

Other versions

NO20020832L (no

NO20020832D0 (no

Inventor

Andrew Peter Thomas

Phillip John Jewsbury

John Franklin Beattie

Gloria Anne Breault

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

2002-02-20

Publication date

2006-12-11

2002-02-20 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2002-02-20 Publication of NO20020832D0 publication Critical patent/NO20020832D0/no

2002-04-12 Publication of NO20020832L publication Critical patent/NO20020832L/no

2006-12-11 Publication of NO322818B1 publication Critical patent/NO322818B1/no

Links

238000002360 preparation method Methods 0.000 title claims description 14
UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 title claims description 8
239000000825 pharmaceutical preparation Substances 0.000 title claims description 5
DVUBDHRTVYLIPA-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine Chemical class C1=CC=CN2N=CC=C21 DVUBDHRTVYLIPA-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 168
-1 cyano, hydroxy Chemical group 0.000 claims description 113
238000000034 method Methods 0.000 claims description 110
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 89
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 65
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 63
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 60
125000000217 alkyl group Chemical group 0.000 claims description 53
150000002148 esters Chemical class 0.000 claims description 49
238000001727 in vivo Methods 0.000 claims description 47
150000003839 salts Chemical class 0.000 claims description 46
229910052757 nitrogen Inorganic materials 0.000 claims description 40
206010028980 Neoplasm Diseases 0.000 claims description 31
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 27
125000000623 heterocyclic group Chemical group 0.000 claims description 25
238000011282 treatment Methods 0.000 claims description 23
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 19
229910052799 carbon Inorganic materials 0.000 claims description 19
230000002401 inhibitory effect Effects 0.000 claims description 19
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 17
230000000694 effects Effects 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
239000003814 drug Substances 0.000 claims description 16
230000022131 cell cycle Effects 0.000 claims description 15
241001465754 Metazoa Species 0.000 claims description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 13
201000011510 cancer Diseases 0.000 claims description 12
230000035755 proliferation Effects 0.000 claims description 12
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
241000282414 Homo sapiens Species 0.000 claims description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
229910052794 bromium Inorganic materials 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
239000000460 chlorine Substances 0.000 claims description 9
208000032839 leukemia Diseases 0.000 claims description 9
210000002307 prostate Anatomy 0.000 claims description 9
125000006239 protecting group Chemical group 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 9
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 8
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
229920006395 saturated elastomer Polymers 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 7
210000000481 breast Anatomy 0.000 claims description 7
210000004072 lung Anatomy 0.000 claims description 7
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
229940079593 drug Drugs 0.000 claims description 6
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201000001320 Atherosclerosis Diseases 0.000 claims description 5
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230000001154 acute effect Effects 0.000 claims description 5
208000038016 acute inflammation Diseases 0.000 claims description 5
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125000003342 alkenyl group Chemical group 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
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239000003153 chemical reaction reagent Substances 0.000 claims description 5
230000001684 chronic effect Effects 0.000 claims description 5
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201000011066 hemangioma Diseases 0.000 claims description 5
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
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206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
125000004434 sulfur atom Chemical group 0.000 claims description 5
208000023275 Autoimmune disease Diseases 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
125000002619 bicyclic group Chemical group 0.000 claims description 4
230000004663 cell proliferation Effects 0.000 claims description 4
230000001419 dependent effect Effects 0.000 claims description 4
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
230000000893 fibroproliferative effect Effects 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
125000002950 monocyclic group Chemical group 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
210000000496 pancreas Anatomy 0.000 claims description 4
230000000306 recurrent effect Effects 0.000 claims description 4
210000003491 skin Anatomy 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 3
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 3
206010005003 Bladder cancer Diseases 0.000 claims description 3
206010006187 Breast cancer Diseases 0.000 claims description 3
208000026310 Breast neoplasm Diseases 0.000 claims description 3
201000003741 Gastrointestinal carcinoma Diseases 0.000 claims description 3
206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
206010033128 Ovarian cancer Diseases 0.000 claims description 3
206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
206010061902 Pancreatic neoplasm Diseases 0.000 claims description 3
206010060862 Prostate cancer Diseases 0.000 claims description 3
208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
208000015634 Rectal Neoplasms Diseases 0.000 claims description 3
208000005718 Stomach Neoplasms Diseases 0.000 claims description 3
208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
125000001589 carboacyl group Chemical group 0.000 claims description 3
125000006125 ethylsulfonyl group Chemical group 0.000 claims description 3
206010017758 gastric cancer Diseases 0.000 claims description 3
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208000020816 lung neoplasm Diseases 0.000 claims description 3
208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 3
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UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 3
206010038038 rectal cancer Diseases 0.000 claims description 3
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238000002560 therapeutic procedure Methods 0.000 claims description 3
210000001519 tissue Anatomy 0.000 claims description 3
210000003932 urinary bladder Anatomy 0.000 claims description 3
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125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
201000009030 Carcinoma Diseases 0.000 claims description 2
150000001204 N-oxides Chemical class 0.000 claims description 2
206010039491 Sarcoma Diseases 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
210000003734 kidney Anatomy 0.000 claims description 2
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125000004043 oxo group Chemical group O=* 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
210000001957 retinal vein Anatomy 0.000 claims description 2
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
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210000000936 intestine Anatomy 0.000 claims 1
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 138
239000000203 mixture Substances 0.000 description 105
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 66
238000005481 NMR spectroscopy Methods 0.000 description 61
238000001704 evaporation Methods 0.000 description 51
230000008020 evaporation Effects 0.000 description 51
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
239000000243 solution Substances 0.000 description 45
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
238000010992 reflux Methods 0.000 description 34
239000003039 volatile agent Substances 0.000 description 33
238000004587 chromatography analysis Methods 0.000 description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
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ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 11
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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239000000284 extract Substances 0.000 description 9
108090000623 proteins and genes Proteins 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
125000001424 substituent group Chemical group 0.000 description 9
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REULQIKBNNDNDX-UHFFFAOYSA-M sodium;2,3-dihydroxypropyl hydrogen phosphate Chemical compound [Na+].OCC(O)COP(O)([O-])=O REULQIKBNNDNDX-UHFFFAOYSA-M 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000010186 staining Methods 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
231100000338 sulforhodamine B assay Toxicity 0.000 description 1
238000003210 sulforhodamine B staining Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
229960001603 tamoxifen Drugs 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 1
229960001278 teniposide Drugs 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
POHWAQLZBIMPRN-UHFFFAOYSA-N tert-butyl n-(3-aminopropyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCN POHWAQLZBIMPRN-UHFFFAOYSA-N 0.000 description 1
229960003604 testosterone Drugs 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
PCZOZSATUTWXIC-UHFFFAOYSA-N tetraethylazanium;cyanide Chemical compound N#[C-].CC[N+](CC)(CC)CC PCZOZSATUTWXIC-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 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
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
125000005505 thiomorpholino group Chemical group 0.000 description 1
229960001196 thiotepa Drugs 0.000 description 1
229960004072 thrombin Drugs 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
229940044693 topoisomerase inhibitor Drugs 0.000 description 1
UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
229960000303 topotecan Drugs 0.000 description 1
XFCLJVABOIYOMF-QPLCGJKRSA-N toremifene Chemical compound C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 XFCLJVABOIYOMF-QPLCGJKRSA-N 0.000 description 1
229960005026 toremifene Drugs 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
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125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
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230000003827 upregulation Effects 0.000 description 1
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125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000001262 western blot Methods 0.000 description 1
229910000166 zirconium phosphate Inorganic materials 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A—HUMAN NECESSITIES
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P17/06—Antipsoriatics
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
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- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

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Health & Medical Sciences (AREA)
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Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Pharmacology & Pharmacy (AREA)
Public Health (AREA)
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Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Urology & Nephrology (AREA)
Physical Education & Sports Medicine (AREA)
Cardiology (AREA)
Rheumatology (AREA)
Immunology (AREA)
Heart & Thoracic Surgery (AREA)
Orthopedic Medicine & Surgery (AREA)
Vascular Medicine (AREA)
Pain & Pain Management (AREA)
Ophthalmology & Optometry (AREA)
Hematology (AREA)
Oncology (AREA)
Pulmonology (AREA)
Dermatology (AREA)
Neurology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO20020832A 1999-08-21 2002-02-20 Imidazo(1,2-A)pyridin og pyrazolo(2,3-A)pyridin derivater, anvendelse og fremstilling derav, samt farmasoytisk preparat. NO322818B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9919778.2A GB9919778D0 (en)	1999-08-21	1999-08-21	Chemical compounds
PCT/GB2000/003139 WO2001014375A1 (en)	1999-08-21	2000-08-15	Imidazo[1,2-a]pyridine and pyrazolo[2,3-a]pyridine derivatives

Publications (3)

Publication Number	Publication Date
NO20020832D0 NO20020832D0 (no)	2002-02-20
NO20020832L NO20020832L (no)	2002-04-12
NO322818B1 true NO322818B1 (no)	2006-12-11

Family

ID=10859538

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20020832A NO322818B1 (no)	1999-08-21	2002-02-20	Imidazo(1,2-A)pyridin og pyrazolo(2,3-A)pyridin derivater, anvendelse og fremstilling derav, samt farmasoytisk preparat.

Country Status (33)

Country	Link
US (1)	US6855719B1 (es)
EP (1)	EP1214318B1 (es)
JP (1)	JP4280442B2 (es)
KR (1)	KR100737259B1 (es)
CN (1)	CN1174981C (es)
AR (1)	AR031075A1 (es)
AT (1)	ATE251623T1 (es)
AU (1)	AU757639B2 (es)
BG (1)	BG65566B1 (es)
BR (1)	BR0013476A (es)
CA (1)	CA2376293A1 (es)
CO (1)	CO5460265A1 (es)
CZ (1)	CZ2002617A3 (es)
DE (1)	DE60005850T2 (es)
DK (1)	DK1214318T3 (es)
EE (1)	EE04964B1 (es)
ES (1)	ES2208397T3 (es)
GB (1)	GB9919778D0 (es)
HK (1)	HK1045510B (es)
HU (1)	HUP0202494A3 (es)
IL (2)	IL147752A0 (es)
IS (1)	IS2068B (es)
MX (1)	MXPA02001674A (es)
MY (1)	MY123390A (es)
NO (1)	NO322818B1 (es)
NZ (1)	NZ516740A (es)
PL (1)	PL199615B1 (es)
PT (1)	PT1214318E (es)
RU (1)	RU2248976C2 (es)
SK (1)	SK287033B6 (es)
UA (1)	UA73522C2 (es)
WO (1)	WO2001014375A1 (es)
ZA (1)	ZA200200028B (es)

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- 2000-08-15 WO PCT/GB2000/003139 patent/WO2001014375A1/en not_active Ceased
- 2000-08-15 AU AU65833/00A patent/AU757639B2/en not_active Ceased
- 2000-08-15 PL PL364722A patent/PL199615B1/pl not_active IP Right Cessation
- 2000-08-15 EP EP00953319A patent/EP1214318B1/en not_active Expired - Lifetime
- 2000-08-15 CZ CZ2002617A patent/CZ2002617A3/cs unknown
- 2000-08-15 DE DE60005850T patent/DE60005850T2/de not_active Expired - Lifetime
- 2000-08-15 NZ NZ516740A patent/NZ516740A/en unknown
- 2000-08-15 HU HU0202494A patent/HUP0202494A3/hu unknown
- 2000-08-15 PT PT00953319T patent/PT1214318E/pt unknown
- 2000-08-15 HK HK02107002.9A patent/HK1045510B/en not_active IP Right Cessation
- 2000-08-15 RU RU2002107128/04A patent/RU2248976C2/ru not_active IP Right Cessation
- 2000-08-15 IL IL14775200A patent/IL147752A0/xx active IP Right Grant
- 2000-08-17 CO CO00061949A patent/CO5460265A1/es not_active Application Discontinuation
- 2000-08-18 AR ARP000104309A patent/AR031075A1/es not_active Application Discontinuation
- 2000-08-18 MY MYPI20003812 patent/MY123390A/en unknown
2002
- 2002-01-02 ZA ZA200200028A patent/ZA200200028B/en unknown
- 2002-01-21 IL IL147752A patent/IL147752A/en not_active IP Right Cessation
- 2002-02-04 BG BG106383A patent/BG65566B1/bg unknown
- 2002-02-15 IS IS6274A patent/IS2068B/xx unknown
- 2002-02-20 NO NO20020832A patent/NO322818B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
CO5460265A1 (es)	2004-11-30
US6855719B1 (en)	2005-02-15
BR0013476A (pt)	2002-04-30
EE200200080A (et)	2003-06-16
IS2068B (is)	2005-11-15
AR031075A1 (es)	2003-09-10
HK1045510A1 (en)	2002-11-29
RU2248976C2 (ru)	2005-03-27
CZ2002617A3 (cs)	2002-06-12
MXPA02001674A (es)	2002-08-06
AU757639B2 (en)	2003-02-27
CN1174981C (zh)	2004-11-10
PT1214318E (pt)	2004-02-27
SK287033B6 (sk)	2009-10-07
IL147752A0 (en)	2002-08-14
SK2402002A3 (en)	2002-09-10
EP1214318A1 (en)	2002-06-19
DE60005850D1 (de)	2003-11-13
EE04964B1 (et)	2008-02-15
ZA200200028B (en)	2003-04-02
DK1214318T3 (da)	2004-02-09
ES2208397T3 (es)	2004-06-16
KR100737259B1 (ko)	2007-07-10
WO2001014375A1 (en)	2001-03-01
ATE251623T1 (de)	2003-10-15
JP2003507478A (ja)	2003-02-25
HUP0202494A3 (en)	2003-10-28
IS6274A (is)	2002-02-15
PL364722A1 (en)	2004-12-13
EP1214318B1 (en)	2003-10-08
PL199615B1 (pl)	2008-10-31
IL147752A (en)	2006-06-11
UA73522C2 (en)	2005-08-15
MY123390A (en)	2006-05-31
GB9919778D0 (en)	1999-10-27
KR20020021411A (ko)	2002-03-20
NO20020832L (no)	2002-04-12
BG65566B1 (bg)	2008-12-30
NZ516740A (en)	2004-09-24
AU6583300A (en)	2001-03-19
NO20020832D0 (no)	2002-02-20
HK1045510B (en)	2004-03-19
HUP0202494A2 (en)	2002-10-28
CN1370163A (zh)	2002-09-18
JP4280442B2 (ja)	2009-06-17
CA2376293A1 (en)	2001-03-01
DE60005850T2 (de)	2005-03-24
BG106383A (en)	2002-09-30

Publication	Publication Date	Title
NO322818B1 (no)	2006-12-11	Imidazo(1,2-A)pyridin og pyrazolo(2,3-A)pyridin derivater, anvendelse og fremstilling derav, samt farmasoytisk preparat.
JP4913305B2 (ja)	2012-04-11	ピリミジン化合物
AU2001239414B2 (en)	2004-09-02	4-amino-5-cyano-2-anilino-pyrimidine derivatives and their use as inhibitors of cell-cycle kinases
KR100663773B1 (ko)	2007-01-03	피리미딘 화합물
KR100683512B1 (ko)	2007-02-16	피리미딘 화합물
NO325280B1 (no)	2008-03-17	Pyrimidin-derivater, fremgangsmate for fremstilling av slike, farmasoytisk preparat inneholdende slike, slike forbindelser for anvendelse som medikament samt anvendelse av slike forbindelser for fremstilling av medikament for behandling av sykdommer
NO326831B1 (no)	2009-02-23	Pyrimidinderivater samt anvendelse og fremgangsmate for fremstilling derav, og farmasoytisk preparat
EP2044058A1 (en)	2009-04-08	Chemical compounds
MXPA01006575A (es)	2002-03-26	Compuesto de 2,4-diamino pirimidina que tiene actividades contra la proliferación de celulas

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