OA12227A - 5-AlkylpyridoÄ2,3-DÜpyrimidines tyrosine kinase inhibitors. - Google Patents

5-AlkylpyridoÄ2,3-DÜpyrimidines tyrosine kinase inhibitors. Download PDF

Info

Publication number: OA12227A
Authority: OA; OAPI
Prior art keywords: compound; pyrido; methyl; pyrimidin; cyclopentyl
Prior art date: 2000-03-06

Application number

OA1200200281A

Other languages

English (en)

Inventor

Richard John Booth

Ellen Myra Dobrusin

Peter Laurence Toogood

Scott Norman Vanderwel

Original Assignee

Warner Lambert Co

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.)

2000-03-06

Filing date

2001-01-29

Publication date

2004-03-18

2001-01-29 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

2004-03-18 Publication of OA12227A publication Critical patent/OA12227A/en

Links

229940121358 tyrosine kinase inhibitor Drugs 0.000 title description 2
239000005483 tyrosine kinase inhibitor Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 412
125000000217 alkyl group Chemical group 0.000 claims abstract description 81
229910052736 halogen Inorganic materials 0.000 claims abstract description 48
150000002367 halogens Chemical class 0.000 claims abstract description 48
125000003545 alkoxy group Chemical group 0.000 claims abstract description 43
239000001257 hydrogen Substances 0.000 claims abstract description 39
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 39
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 36
150000002431 hydrogen Chemical class 0.000 claims abstract description 32
125000003118 aryl group Chemical group 0.000 claims abstract description 31
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 27
150000002825 nitriles Chemical class 0.000 claims abstract description 20
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 20
206010028980 Neoplasm Diseases 0.000 claims abstract description 18
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
125000003342 alkenyl group Chemical group 0.000 claims abstract description 16
201000011510 cancer Diseases 0.000 claims abstract description 14
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 12
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
102000003903 Cyclin-dependent kinases Human genes 0.000 claims abstract description 9
108090000266 Cyclin-dependent kinases Proteins 0.000 claims abstract description 9
208000037803 restenosis Diseases 0.000 claims abstract description 9
125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
201000001320 Atherosclerosis Diseases 0.000 claims abstract description 5
239000003102 growth factor Substances 0.000 claims abstract description 5
230000001404 mediated effect Effects 0.000 claims abstract description 5
-1 aîkylcarbonyl Chemical group 0.000 claims description 80
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 55
229910052717 sulfur Inorganic materials 0.000 claims description 41
229910052760 oxygen Inorganic materials 0.000 claims description 40
125000002837 carbocyclic group Chemical group 0.000 claims description 34
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 32
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 32
239000000203 mixture Substances 0.000 claims description 31
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 27
239000001301 oxygen Substances 0.000 claims description 27
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 25
239000011593 sulfur Substances 0.000 claims description 25
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
125000001072 heteroaryl group Chemical group 0.000 claims description 23
229960001171 acetohydroxamic acid Drugs 0.000 claims description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 19
229910020008 S(O) Inorganic materials 0.000 claims description 18
125000004663 dialkyl amino group Chemical group 0.000 claims description 18
125000005842 heteroatom Chemical group 0.000 claims description 18
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 18
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 17
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 16
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
150000001408 amides Chemical class 0.000 claims description 16
125000004103 aminoalkyl group Chemical group 0.000 claims description 16
150000002148 esters Chemical class 0.000 claims description 16
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 16
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 13
RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 claims description 12
201000010099 disease Diseases 0.000 claims description 11
239000000651 prodrug Substances 0.000 claims description 11
229940002612 prodrug Drugs 0.000 claims description 11
WDHAAJIGSXNPFO-UHFFFAOYSA-N 8h-pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=CN=C2NC(=O)C=CC2=C1 WDHAAJIGSXNPFO-UHFFFAOYSA-N 0.000 claims description 10
LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 claims description 10
TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 claims description 9
125000005843 halogen group Chemical group 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000005936 piperidyl group Chemical group 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
150000001450 anions Chemical class 0.000 claims description 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
101100295741 Gallus gallus COR4 gene Proteins 0.000 claims description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
PMFXXHFUSDMPRP-UHFFFAOYSA-N 2-(4-fluoro-3-methylanilino)-5-methyl-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C(C)=CC(=O)N(C(C)C)C2=NC=1NC1=CC=C(F)C(C)=C1 PMFXXHFUSDMPRP-UHFFFAOYSA-N 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
229940125904 compound 1 Drugs 0.000 claims description 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
208000035475 disorder Diseases 0.000 claims description 5
230000002401 inhibitory effect Effects 0.000 claims description 5
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims description 4
VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 claims description 4
201000004681 Psoriasis Diseases 0.000 claims description 4
241000700605 Viruses Species 0.000 claims description 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
229940125797 compound 12 Drugs 0.000 claims description 4
229940126214 compound 3 Drugs 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 claims description 3
SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 claims description 3
241000124008 Mammalia Species 0.000 claims description 3
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 3
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 3
SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
229940127573 compound 38 Drugs 0.000 claims description 3
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 claims description 3
229940080818 propionamide Drugs 0.000 claims description 3
UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 claims description 2
AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 claims description 2
ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 claims description 2
GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims description 2
GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 claims description 2
IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 claims description 2
YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 claims description 2
VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 claims description 2
WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 claims description 2
STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 claims description 2
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims description 2
FNHHVPPSBFQMEL-KQHDFZBMSA-N (3S)-5-N-[(1S,5R)-3-hydroxy-6-bicyclo[3.1.0]hexanyl]-7-N,3-dimethyl-3-phenyl-2H-1-benzofuran-5,7-dicarboxamide Chemical compound CNC(=O)c1cc(cc2c1OC[C@@]2(C)c1ccccc1)C(=O)NC1[C@H]2CC(O)C[C@@H]12 FNHHVPPSBFQMEL-KQHDFZBMSA-N 0.000 claims description 2
IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 claims description 2
UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 claims description 2
OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 claims description 2
HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 claims description 2
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YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 claims description 2
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231100000588 tumorigenic Toxicity 0.000 description 1
230000000381 tumorigenic effect Effects 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
208000010576 undifferentiated carcinoma Diseases 0.000 description 1
241000701447 unidentified baculovirus Species 0.000 description 1
241001529453 unidentified herpesvirus Species 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
239000008215 water for injection Substances 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
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- 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)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

OA1200200281A 2000-03-06 2001-01-29 5-AlkylpyridoÄ2,3-DÜpyrimidines tyrosine kinase inhibitors. OA12227A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US18712400P	2000-03-06	2000-03-06

Publications (1)

Publication Number	Publication Date
OA12227A true OA12227A (en)	2004-03-18

Family

ID=22687699

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200200281A OA12227A (en)	2000-03-06	2001-01-29	5-AlkylpyridoÄ2,3-DÜpyrimidines tyrosine kinase inhibitors.

Country Status (36)

Country	Link
EP (1)	EP1268476A1 (no)
JP (1)	JP2003528101A (no)
KR (1)	KR20020075805A (no)
CN (1)	CN1422268A (no)
AP (1)	AP2002002643A0 (no)
AR (1)	AR034119A1 (no)
AU (1)	AU2001233028A1 (no)
BG (1)	BG107161A (no)
BR (1)	BR0109056A (no)
CA (1)	CA2401368A1 (no)
CO (1)	CO5280200A1 (no)
CR (1)	CR6736A (no)
CZ (1)	CZ20022929A3 (no)
DZ (1)	DZ3308A1 (no)
EA (1)	EA200200802A1 (no)
EE (1)	EE200200506A (no)
GT (1)	GT200100037A (no)
HN (1)	HN2001000040A (no)
HR (1)	HRP20020798A2 (no)
HU (1)	HUP0300136A2 (no)
IL (1)	IL151480A0 (no)
IS (1)	IS6524A (no)
MA (1)	MA26881A1 (no)
MX (1)	MXPA02008535A (no)
NO (1)	NO20024235L (no)
NZ (1)	NZ520962A (no)
OA (1)	OA12227A (no)
PA (1)	PA8513201A1 (no)
PE (1)	PE20011177A1 (no)
PL (1)	PL358271A1 (no)
SK (1)	SK12472002A3 (no)
SV (1)	SV2001000338A (no)
TN (1)	TNSN01036A1 (no)
WO (1)	WO2001070741A1 (no)
YU (1)	YU66502A (no)
ZA (1)	ZA200207110B (no)

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2001
- 2001-01-29 OA OA1200200281A patent/OA12227A/en unknown
- 2001-01-29 NZ NZ520962A patent/NZ520962A/en unknown
- 2001-01-29 KR KR1020027011627A patent/KR20020075805A/ko not_active Withdrawn
- 2001-01-29 EA EA200200802A patent/EA200200802A1/ru unknown
- 2001-01-29 HR HR20020798A patent/HRP20020798A2/xx not_active Application Discontinuation
- 2001-01-29 IL IL15148001A patent/IL151480A0/xx unknown
- 2001-01-29 MX MXPA02008535A patent/MXPA02008535A/es not_active Application Discontinuation
- 2001-01-29 CA CA002401368A patent/CA2401368A1/en not_active Abandoned
- 2001-01-29 HU HU0300136A patent/HUP0300136A2/hu unknown
- 2001-01-29 DZ DZ013308A patent/DZ3308A1/fr active
- 2001-01-29 PL PL01358271A patent/PL358271A1/xx not_active Application Discontinuation
- 2001-01-29 EP EP01905114A patent/EP1268476A1/en not_active Withdrawn
- 2001-01-29 WO PCT/US2001/002657 patent/WO2001070741A1/en not_active Ceased
- 2001-01-29 YU YU66502A patent/YU66502A/sh unknown
- 2001-01-29 AP APAP/P/2002/002643A patent/AP2002002643A0/en unknown
- 2001-01-29 AU AU2001233028A patent/AU2001233028A1/en not_active Abandoned
- 2001-01-29 CN CN01807590A patent/CN1422268A/zh active Pending
- 2001-01-29 EE EEP200200506A patent/EE200200506A/xx unknown
- 2001-01-29 CZ CZ20022929A patent/CZ20022929A3/cs unknown
- 2001-01-29 JP JP2001568942A patent/JP2003528101A/ja not_active Abandoned
- 2001-01-29 BR BR0109056-9A patent/BR0109056A/pt not_active IP Right Cessation
- 2001-01-29 SK SK1247-2002A patent/SK12472002A3/sk unknown
- 2001-03-02 TN TNTNSN01036A patent/TNSN01036A1/en unknown
- 2001-03-05 PA PA20018513201A patent/PA8513201A1/es unknown
- 2001-03-05 PE PE2001000216A patent/PE20011177A1/es not_active Application Discontinuation
- 2001-03-05 CO CO01017398A patent/CO5280200A1/es not_active Application Discontinuation
- 2001-03-05 SV SV2001000338A patent/SV2001000338A/es not_active Application Discontinuation
- 2001-03-05 AR ARP010101039A patent/AR034119A1/es unknown
- 2001-03-05 HN HN2001000040A patent/HN2001000040A/es unknown
- 2001-03-05 GT GT200100037A patent/GT200100037A/es unknown
2002
- 2002-08-23 IS IS6524A patent/IS6524A/is unknown
- 2002-08-23 CR CR6736A patent/CR6736A/es not_active Application Discontinuation
- 2002-09-04 MA MA26801A patent/MA26881A1/fr unknown
- 2002-09-04 ZA ZA200207110A patent/ZA200207110B/en unknown
- 2002-09-05 NO NO20024235A patent/NO20024235L/no not_active Application Discontinuation
- 2002-10-02 BG BG107161A patent/BG107161A/xx unknown

Also Published As

Publication number	Publication date
YU66502A (sh)	2005-09-19
TNSN01036A1 (en)	2005-11-10
AR034119A1 (es)	2004-02-04
SK12472002A3 (sk)	2003-04-01
AU2001233028A1 (en)	2001-10-03
HUP0300136A2 (en)	2003-05-28
SV2001000338A (es)	2001-11-30
NO20024235D0 (no)	2002-09-05
IL151480A0 (en)	2003-04-10
CN1422268A (zh)	2003-06-04
PL358271A1 (en)	2004-08-09
BR0109056A (pt)	2003-06-03
EE200200506A (et)	2004-02-16
MA26881A1 (fr)	2004-12-20
HRP20020798A2 (en)	2004-02-29
EP1268476A1 (en)	2003-01-02
NZ520962A (en)	2003-09-26
CA2401368A1 (en)	2001-09-27
GT200100037A (es)	2002-03-04
ZA200207110B (en)	2003-12-04
NO20024235L (no)	2002-11-05
WO2001070741A1 (en)	2001-09-27
KR20020075805A (ko)	2002-10-05
PA8513201A1 (es)	2003-06-30
CR6736A (es)	2004-03-10
CZ20022929A3 (cs)	2003-02-12
JP2003528101A (ja)	2003-09-24
CO5280200A1 (es)	2003-05-30
PE20011177A1 (es)	2001-11-23
HN2001000040A (es)	2001-09-06
DZ3308A1 (fr)	2001-09-27
BG107161A (en)	2003-06-30
AP2002002643A0 (en)	2002-12-31
IS6524A (is)	2002-08-23
EA200200802A1 (ru)	2003-02-27
MXPA02008535A (es)	2002-12-13

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