NO325443B1 - Pyrimidinderivater, fremgangsmate for fremstilling av slike, farmasoytiske preparater inneholdende disse, disse forbindelsene anvendt i terapeutisk behandling samt anvendelse av disse for fremstilling av medikament for behandling av sykdommer - Google Patents

Pyrimidinderivater, fremgangsmate for fremstilling av slike, farmasoytiske preparater inneholdende disse, disse forbindelsene anvendt i terapeutisk behandling samt anvendelse av disse for fremstilling av medikament for behandling av sykdommer Download PDF

Info

Publication number: NO325443B1
Authority: NO; Norway
Prior art keywords: alkyl; 4alkyl; substituted; group; amino
Prior art date: 2000-03-01

Application number

NO20024126A

Other languages

English (en)

Norwegian (no)

Other versions

NO20024126L (no

NO20024126D0 (no

Inventor

Robert Hugh Bradbury

Stuart Eric Pearson

Elizabeth Janet Pease

Emma Jane Williams

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.)

2000-03-01

Filing date

2002-08-29

Publication date

2008-05-05

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=9886703&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NO325443(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2002-08-29 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2002-08-29 Publication of NO20024126L publication Critical patent/NO20024126L/no

2002-08-29 Publication of NO20024126D0 publication Critical patent/NO20024126D0/no

2008-05-05 Publication of NO325443B1 publication Critical patent/NO325443B1/no

Links

238000000034 method Methods 0.000 title claims abstract description 102
150000003230 pyrimidines Chemical class 0.000 title claims abstract description 41
230000008569 process Effects 0.000 title claims abstract description 9
238000004519 manufacturing process Methods 0.000 title claims abstract description 6
150000001875 compounds Chemical class 0.000 title claims description 73
238000011282 treatment Methods 0.000 title claims description 21
238000002360 preparation method Methods 0.000 title claims description 12
239000003814 drug Substances 0.000 title claims description 9
230000001225 therapeutic effect Effects 0.000 title claims description 7
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title abstract description 4
239000008194 pharmaceutical composition Substances 0.000 title abstract 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 11
201000010099 disease Diseases 0.000 title description 9
150000003839 salts Chemical class 0.000 claims abstract description 42
150000002148 esters Chemical class 0.000 claims abstract description 37
238000001727 in vivo Methods 0.000 claims abstract description 37
-1 hydroxy, mercapto Chemical class 0.000 claims description 150
125000000217 alkyl group Chemical group 0.000 claims description 59
125000000623 heterocyclic group Chemical group 0.000 claims description 41
125000001424 substituent group Chemical group 0.000 claims description 34
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 33
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 25
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 23
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 22
229910052757 nitrogen Inorganic materials 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 20
229910052799 carbon Inorganic materials 0.000 claims description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
125000003545 alkoxy group Chemical group 0.000 claims description 18
230000000694 effects Effects 0.000 claims description 18
230000002401 inhibitory effect Effects 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
229910052736 halogen Inorganic materials 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 13
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
125000000304 alkynyl group Chemical group 0.000 claims description 12
230000022131 cell cycle Effects 0.000 claims description 12
241001465754 Metazoa Species 0.000 claims description 10
125000005236 alkanoylamino group Chemical group 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 9
239000001257 hydrogen Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
230000035755 proliferation Effects 0.000 claims description 9
125000006239 protecting group Chemical group 0.000 claims description 9
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
230000015572 biosynthetic process Effects 0.000 claims description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
230000001093 anti-cancer Effects 0.000 claims description 6
230000006907 apoptotic process Effects 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
230000001939 inductive effect Effects 0.000 claims description 5
238000013508 migration Methods 0.000 claims description 5
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
239000000825 pharmaceutical preparation Substances 0.000 claims description 5
241000282412 Homo Species 0.000 claims description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
230000005012 migration Effects 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000005133 alkynyloxy group Chemical group 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000002619 bicyclic group Chemical group 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims description 3
125000002950 monocyclic group Chemical group 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
230000000069 prophylactic effect Effects 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
125000003302 alkenyloxy group Chemical group 0.000 claims description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
PIEMJWXGWDBCMN-UHFFFAOYSA-N 2-[4-[(4-anilino-5-bromopyrimidin-2-yl)amino]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1NC1=NC=C(Br)C(NC=2C=CC=CC=2)=N1 PIEMJWXGWDBCMN-UHFFFAOYSA-N 0.000 claims 1
DUPNQUDKGLFCEW-UHFFFAOYSA-N 5-bromo-2-n-[4-(1-methylpiperidin-4-yl)oxyphenyl]-4-n-phenylpyrimidine-2,4-diamine Chemical compound C1CN(C)CCC1OC(C=C1)=CC=C1NC1=NC=C(Br)C(NC=2C=CC=CC=2)=N1 DUPNQUDKGLFCEW-UHFFFAOYSA-N 0.000 claims 1
FLYWDADPUYSEFG-UHFFFAOYSA-N 5-bromo-2-n-[4-[2-(dimethylamino)ethoxy]phenyl]-4-n-phenylpyrimidine-2,4-diamine Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NC=C(Br)C(NC=2C=CC=CC=2)=N1 FLYWDADPUYSEFG-UHFFFAOYSA-N 0.000 claims 1
ARBYNWNBIKVNNJ-UHFFFAOYSA-N 5-bromo-2-n-[4-[3-(methylamino)prop-1-ynyl]phenyl]-4-n-phenylpyrimidine-2,4-diamine Chemical compound C1=CC(C#CCNC)=CC=C1NC1=NC=C(Br)C(NC=2C=CC=CC=2)=N1 ARBYNWNBIKVNNJ-UHFFFAOYSA-N 0.000 claims 1
VGDBUSCPHQFLTB-UHFFFAOYSA-N 5-bromo-4-n-phenyl-2-n-[4-[2-(propan-2-ylamino)ethylamino]phenyl]pyrimidine-2,4-diamine Chemical compound C1=CC(NCCNC(C)C)=CC=C1NC1=NC=C(Br)C(NC=2C=CC=CC=2)=N1 VGDBUSCPHQFLTB-UHFFFAOYSA-N 0.000 claims 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
108010067715 Focal Adhesion Protein-Tyrosine Kinases Proteins 0.000 abstract description 27
102000016621 Focal Adhesion Protein-Tyrosine Kinases Human genes 0.000 abstract description 27
239000003112 inhibitor Substances 0.000 abstract description 17
102000016736 Cyclin Human genes 0.000 abstract description 5
108050006400 Cyclin Proteins 0.000 abstract description 5
230000001419 dependent effect Effects 0.000 abstract description 4
101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 abstract description 3
102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 abstract description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
210000004027 cell Anatomy 0.000 description 37
239000000047 product Substances 0.000 description 36
239000000243 solution Substances 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
238000004949 mass spectrometry Methods 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
238000001704 evaporation Methods 0.000 description 20
230000008020 evaporation Effects 0.000 description 20
239000000203 mixture Substances 0.000 description 20
108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 description 18
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FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
206010028980 Neoplasm Diseases 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 14
125000002252 acyl group Chemical group 0.000 description 13
235000011114 ammonium hydroxide Nutrition 0.000 description 13
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NKUZAJOBLJQQPW-UHFFFAOYSA-N 5-bromo-2-chloro-n-phenylpyrimidin-4-amine Chemical compound ClC1=NC=C(Br)C(NC=2C=CC=CC=2)=N1 NKUZAJOBLJQQPW-UHFFFAOYSA-N 0.000 description 11
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
238000010828 elution Methods 0.000 description 9
239000007787 solid Substances 0.000 description 9
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 8
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
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KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
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PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 8
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239000000284 extract Substances 0.000 description 7
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238000010561 standard procedure Methods 0.000 description 7
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238000012360 testing method Methods 0.000 description 7
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229960001456 adenosine triphosphate Drugs 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 6
238000002474 experimental method Methods 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
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108060006633 protein kinase Proteins 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
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125000002098 pyridazinyl group Chemical group 0.000 description 1
125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 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
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
238000001959 radiotherapy Methods 0.000 description 1
229960004622 raloxifene Drugs 0.000 description 1
GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 description 1
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238000012163 sequencing technique Methods 0.000 description 1
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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
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000000527 sonication Methods 0.000 description 1
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HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
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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
229940063683 taxotere Drugs 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
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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101150061166 tetR gene Proteins 0.000 description 1
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229930101283 tetracycline Natural products 0.000 description 1
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
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238000002560 therapeutic procedure Methods 0.000 description 1
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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
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
- C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
- C04B35/632—Organic additives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Ceramic Engineering (AREA)
Manufacturing & Machinery (AREA)
Health & Medical Sciences (AREA)
Inorganic Chemistry (AREA)
Structural Engineering (AREA)
Materials Engineering (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Saccharide Compounds (AREA)
Hydrogenated Pyridines (AREA)

NO20024126A 2000-03-01 2002-08-29 Pyrimidinderivater, fremgangsmate for fremstilling av slike, farmasoytiske preparater inneholdende disse, disse forbindelsene anvendt i terapeutisk behandling samt anvendelse av disse for fremstilling av medikament for behandling av sykdommer NO325443B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB0004887.6A GB0004887D0 (en)	2000-03-01	2000-03-01	Chemical compounds
PCT/GB2001/000829 WO2001064656A1 (en)	2000-03-01	2001-02-26	2,4,di(hetero-)arylamino(-oxy)-5-substituted pyrimidines as antineoplastic agents

Publications (3)

Publication Number	Publication Date
NO20024126L NO20024126L (no)	2002-08-29
NO20024126D0 NO20024126D0 (no)	2002-08-29
NO325443B1 true NO325443B1 (no)	2008-05-05

Family

ID=9886703

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NO20024126A NO325443B1 (no)	2000-03-01	2002-08-29	Pyrimidinderivater, fremgangsmate for fremstilling av slike, farmasoytiske preparater inneholdende disse, disse forbindelsene anvendt i terapeutisk behandling samt anvendelse av disse for fremstilling av medikament for behandling av sykdommer
NO2021008C NO2021008I1 (no)	2000-03-01	2021-02-22	fedratinib eller et farmasøytisk akseptabelt salt derav

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
NO2021008C NO2021008I1 (no)	2000-03-01	2021-02-22	fedratinib eller et farmasøytisk akseptabelt salt derav

Country Status (25)

Country	Link
US (2)	US6838464B2 (cs)
EP (1)	EP1278735B1 (cs)
JP (2)	JP2003525279A (cs)
KR (2)	KR20020075463A (cs)
CN (1)	CN1220684C (cs)
AT (1)	ATE472537T1 (cs)
AU (2)	AU2001233979B2 (cs)
BE (1)	BE2021C507I2 (cs)
BR (1)	BR0108879A (cs)
CA (1)	CA2398887C (cs)
CY (2)	CY1111093T1 (cs)
DE (1)	DE60142469D1 (cs)
DK (1)	DK1278735T3 (cs)
ES (1)	ES2346288T3 (cs)
FR (1)	FR21C1010I2 (cs)
GB (1)	GB0004887D0 (cs)
HK (1)	HK1053111B (cs)
IL (2)	IL150920A0 (cs)
LU (1)	LUC00197I2 (cs)
MX (1)	MXPA02007581A (cs)
NO (2)	NO325443B1 (cs)
NZ (1)	NZ520502A (cs)
PT (1)	PT1278735E (cs)
WO (1)	WO2001064656A1 (cs)
ZA (1)	ZA200206192B (cs)

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US8853266B2 (en) *	2001-12-06	2014-10-07	University Of Tennessee Research Foundation	Selective androgen receptor modulators for treating diabetes
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GB0205690D0 (en)	2002-03-09	2002-04-24	Astrazeneca Ab	Chemical compounds
JP2005524672A (ja)	2002-03-09	2005-08-18	アストラゼネカアクチボラグ	Ｃｄｋ阻害活性を有するイミダゾリル置換ピリミジン誘導体
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2000
- 2000-03-01 GB GBGB0004887.6A patent/GB0004887D0/en not_active Ceased
2001
- 2001-02-26 PT PT01906021T patent/PT1278735E/pt unknown
- 2001-02-26 AT AT01906021T patent/ATE472537T1/de active
- 2001-02-26 CA CA002398887A patent/CA2398887C/en not_active Expired - Lifetime
- 2001-02-26 CN CNB018058469A patent/CN1220684C/zh not_active Expired - Lifetime
- 2001-02-26 NZ NZ520502A patent/NZ520502A/en not_active IP Right Cessation
- 2001-02-26 KR KR1020027011409A patent/KR20020075463A/ko not_active Withdrawn
- 2001-02-26 WO PCT/GB2001/000829 patent/WO2001064656A1/en not_active Ceased
- 2001-02-26 BR BR0108879-3A patent/BR0108879A/pt not_active IP Right Cessation
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- 2001-02-26 JP JP2001563498A patent/JP2003525279A/ja active Pending
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- 2001-02-26 DE DE60142469T patent/DE60142469D1/de not_active Expired - Lifetime
- 2001-02-26 AU AU2001233979A patent/AU2001233979B2/en not_active Expired
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- 2001-02-26 DK DK01906021.9T patent/DK1278735T3/da active
- 2001-02-26 MX MXPA02007581A patent/MXPA02007581A/es active IP Right Grant
- 2001-02-26 KR KR1020077023656A patent/KR100855258B1/ko not_active Expired - Lifetime
- 2001-02-26 AU AU3397901A patent/AU3397901A/xx active Pending
- 2001-02-26 EP EP01906021A patent/EP1278735B1/en not_active Expired - Lifetime
- 2001-02-26 ES ES01906021T patent/ES2346288T3/es not_active Expired - Lifetime
2002
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- 2002-08-29 NO NO20024126A patent/NO325443B1/no active Protection Beyond IP Right Term
2004
- 2004-08-25 JP JP2004245381A patent/JP4801335B2/ja not_active Expired - Lifetime
- 2004-11-24 US US10/995,931 patent/US7067522B2/en not_active Expired - Lifetime
2010
- 2010-08-26 CY CY20101100784T patent/CY1111093T1/el unknown
2021
- 2021-02-22 NO NO2021008C patent/NO2021008I1/no unknown
- 2021-02-22 BE BE2021C507C patent/BE2021C507I2/nl unknown
- 2021-02-23 FR FR21C1010C patent/FR21C1010I2/fr active Active
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Also Published As

Publication number	Publication date
US7067522B2 (en)	2006-06-27
CA2398887C (en)	2008-12-16
ES2346288T3 (es)	2010-10-14
HK1053111A1 (en)	2003-10-10
JP4801335B2 (ja)	2011-10-26
CN1416423A (zh)	2003-05-07
CY2021005I1 (el)	2021-05-05
CN1220684C (zh)	2005-09-28
JP2005041878A (ja)	2005-02-17
WO2001064656A1 (en)	2001-09-07
GB0004887D0 (en)	2000-04-19
NO20024126L (no)	2002-08-29
NO20024126D0 (no)	2002-08-29
BR0108879A (pt)	2003-04-29
US20030181474A1 (en)	2003-09-25
BE2021C507I2 (cs)	2021-02-26
FR21C1010I1 (cs)	2021-05-07
CY2021005I2 (el)	2021-06-25
US20050090515A1 (en)	2005-04-28
FR21C1010I2 (fr)	2022-02-11
AU3397901A (en)	2001-09-12
AU2001233979B2 (en)	2004-11-11
ATE472537T1 (de)	2010-07-15
US6838464B2 (en)	2005-01-04
LUC00197I1 (cs)	2021-02-23
EP1278735A1 (en)	2003-01-29
NO2021008I1 (no)	2021-02-22
PT1278735E (pt)	2010-08-12
CA2398887A1 (en)	2001-09-07
KR20070106806A (ko)	2007-11-05
MXPA02007581A (es)	2002-12-13
KR20020075463A (ko)	2002-10-04
JP2003525279A (ja)	2003-08-26
DE60142469D1 (de)	2010-08-12
CY1111093T1 (el)	2015-06-11
KR100855258B1 (ko)	2008-08-29
HK1053111B (en)	2011-02-18
LUC00197I2 (cs)	2021-07-05
DK1278735T3 (da)	2010-08-30
ZA200206192B (en)	2003-11-26
EP1278735B1 (en)	2010-06-30
IL150920A (en)	2009-08-03
IL150920A0 (en)	2003-02-12
NZ520502A (en)	2004-05-28

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