OA12926A - Novel oxazole and thiazole compounds as transforming growth factor (TGF) inhibitors. - Google Patents

Novel oxazole and thiazole compounds as transforming growth factor (TGF) inhibitors. Download PDF

Info

Publication number: OA12926A
Authority: OA; OAPI
Prior art keywords: alkyl; cio; phenyl; methyl; compound
Prior art date: 2002-09-18

Application number

OA1200500075A

Other languages

English (en)

Inventor

Laura Cook Blumberg

Michael John Munchhof

Original Assignee

Pfizer Prod Inc

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.)

2002-09-18

Filing date

2003-09-08

Publication date

2006-10-13

2003-09-08 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2006-10-13 Publication of OA12926A publication Critical patent/OA12926A/en

Links

102000009618 Transforming Growth Factors Human genes 0.000 title abstract description 16
108010009583 Transforming Growth Factors Proteins 0.000 title abstract description 16
239000003112 inhibitor Substances 0.000 title abstract description 9
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 title description 5
150000003557 thiazoles Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 165
201000010099 disease Diseases 0.000 claims abstract description 20
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 20
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
206010028980 Neoplasm Diseases 0.000 claims abstract description 5
201000011510 cancer Diseases 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims description 96
-1 hydroxy, oxo, mercapto Chemical class 0.000 claims description 64
125000003545 alkoxy group Chemical group 0.000 claims description 35
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
239000000651 prodrug Substances 0.000 claims description 19
229940002612 prodrug Drugs 0.000 claims description 19
125000003118 aryl group Chemical group 0.000 claims description 18
125000001072 heteroaryl group Chemical group 0.000 claims description 16
125000000623 heterocyclic group Chemical group 0.000 claims description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
125000005842 heteroatom Chemical group 0.000 claims description 14
229910052760 oxygen Inorganic materials 0.000 claims description 14
125000004122 cyclic group Chemical group 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 13
125000003282 alkyl amino group Chemical group 0.000 claims description 12
125000000304 alkynyl group Chemical group 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
125000003342 alkenyl group Chemical group 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
229920006395 saturated elastomer Polymers 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
241001465754 Metazoa Species 0.000 claims description 7
125000001624 naphthyl group Chemical group 0.000 claims description 7
125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
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 5
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
125000003368 amide group Chemical group 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
125000003367 polycyclic group Chemical group 0.000 claims description 4
125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
125000004104 aryloxy group Chemical group 0.000 claims description 3
125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
208000007342 Diabetic Nephropathies Diseases 0.000 claims description 2
206010019668 Hepatic fibrosis Diseases 0.000 claims description 2
206010039710 Scleroderma Diseases 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
208000033679 diabetic kidney disease Diseases 0.000 claims description 2
230000002500 effect on skin Effects 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
206010020718 hyperplasia Diseases 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
208000005069 pulmonary fibrosis Diseases 0.000 claims description 2
208000037803 restenosis Diseases 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 10
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
206010018364 Glomerulonephritis Diseases 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
230000037390 scarring Effects 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 9
238000002360 preparation method Methods 0.000 abstract description 5
230000003176 fibrotic effect Effects 0.000 abstract description 3
230000003389 potentiating effect Effects 0.000 abstract description 3
230000037361 pathway Effects 0.000 abstract description 2
150000007979 thiazole derivatives Chemical class 0.000 abstract 1
238000000034 method Methods 0.000 description 65
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 45
238000006243 chemical reaction Methods 0.000 description 32
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
150000003839 salts Chemical class 0.000 description 29
239000000243 solution Substances 0.000 description 29
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 28
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
239000002585 base Substances 0.000 description 26
239000002253 acid Substances 0.000 description 24
239000000203 mixture Substances 0.000 description 23
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 18
125000005843 halogen group Chemical group 0.000 description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
239000002904 solvent Substances 0.000 description 15
229940073584 methylene chloride Drugs 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
102000004887 Transforming Growth Factor beta Human genes 0.000 description 8
108090001012 Transforming Growth Factor beta Proteins 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
239000007787 solid Substances 0.000 description 8
ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
239000003814 drug Substances 0.000 description 7
239000007788 liquid Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
125000005605 benzo group Chemical group 0.000 description 6
150000001768 cations Chemical class 0.000 description 6
229940079593 drug Drugs 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
238000009472 formulation Methods 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
231100000252 nontoxic Toxicity 0.000 description 5
230000003000 nontoxic effect Effects 0.000 description 5
239000002798 polar solvent Substances 0.000 description 5
230000019491 signal transduction Effects 0.000 description 5
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-Lutidine Substances CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 4
KISWVXRQTGLFGD-UHFFFAOYSA-N 2-[[2-[[6-amino-2-[[2-[[2-[[5-amino-2-[[2-[[1-[2-[[6-amino-2-[(2,5-diamino-5-oxopentanoyl)amino]hexanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-(diaminomethylideneamino)p Chemical compound C1CCN(C(=O)C(CCCN=C(N)N)NC(=O)C(CCCCN)NC(=O)C(N)CCC(N)=O)C1C(=O)NC(CO)C(=O)NC(CCC(N)=O)C(=O)NC(CCCN=C(N)N)C(=O)NC(CO)C(=O)NC(CCCCN)C(=O)NC(C(=O)NC(CC(C)C)C(O)=O)CC1=CC=C(O)C=C1 KISWVXRQTGLFGD-UHFFFAOYSA-N 0.000 description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
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 4
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
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UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000012964 benzotriazole Substances 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
150000004677 hydrates Chemical class 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 4
229940011051 isopropyl acetate Drugs 0.000 description 4
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 4
238000000021 kinase assay Methods 0.000 description 4
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
239000012071 phase Substances 0.000 description 4
239000003880 polar aprotic solvent Substances 0.000 description 4
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
239000003586 protic polar solvent Substances 0.000 description 4
230000002441 reversible effect Effects 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
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239000011734 sodium Substances 0.000 description 4
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239000000758 substrate Substances 0.000 description 4
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229910019142 PO4 Inorganic materials 0.000 description 3
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FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical class C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
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239000010410 layer Substances 0.000 description 3
BDGDWWGTAFXEEW-UHFFFAOYSA-N methylsulfinylmethane;oxalyl dichloride Chemical compound CS(C)=O.ClC(=O)C(Cl)=O BDGDWWGTAFXEEW-UHFFFAOYSA-N 0.000 description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
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MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 2
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
ZEMZPXWZVTUONV-UHFFFAOYSA-N 2-(2-dicyclohexylphosphanylphenyl)-n,n-dimethylaniline Chemical group CN(C)C1=CC=CC=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 ZEMZPXWZVTUONV-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 2
XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 2
XIZXADDGOCJZAL-UHFFFAOYSA-N 3h-dioxole-5-carboxylic acid Chemical compound OC(=O)C1=CCOO1 XIZXADDGOCJZAL-UHFFFAOYSA-N 0.000 description 2
AHISYUZBWDSPQL-UHFFFAOYSA-N 6-methylpyridine-2-carbaldehyde Chemical compound CC1=CC=CC(C=O)=N1 AHISYUZBWDSPQL-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
229910014585 C2-Ce Inorganic materials 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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Animal Behavior & Ethology (AREA)
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OA1200500075A 2002-09-18 2003-09-08 Novel oxazole and thiazole compounds as transforming growth factor (TGF) inhibitors. OA12926A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date
US41212002P	2002-09-18	2002-09-18
US47126503P	2003-05-16	2003-05-16
US48458103P	2003-07-02	2003-07-02

Publications (1)

Publication Number	Publication Date
OA12926A true OA12926A (en)	2006-10-13

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ID=32034216

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200500075A OA12926A (en)	2002-09-18	2003-09-08	Novel oxazole and thiazole compounds as transforming growth factor (TGF) inhibitors.

Country Status (28)

Country	Link
US (1)	US7273936B2 (es)
EP (1)	EP1542994B1 (es)
JP (1)	JP4518956B2 (es)
KR (1)	KR20050057415A (es)
CN (1)	CN1681810A (es)
AP (1)	AP2005003261A0 (es)
AR (1)	AR041273A1 (es)
AT (1)	ATE430147T1 (es)
AU (1)	AU2003256003A1 (es)
BR (1)	BR0314383A (es)
CA (1)	CA2499429C (es)
CO (1)	CO5550473A2 (es)
CR (1)	CR7743A (es)
DE (1)	DE60327443D1 (es)
EA (1)	EA200500354A1 (es)
ES (1)	ES2323421T3 (es)
HR (1)	HRP20050250A2 (es)
IS (1)	IS7711A (es)
MA (1)	MA27443A1 (es)
MX (1)	MXPA05002332A (es)
NO (1)	NO20051838L (es)
OA (1)	OA12926A (es)
PA (1)	PA8582701A1 (es)
PE (1)	PE20040987A1 (es)
PL (1)	PL375975A1 (es)
TW (1)	TW200413362A (es)
UY (1)	UY27978A1 (es)
WO (1)	WO2004026863A1 (es)

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2003
- 2003-09-08 MX MXPA05002332A patent/MXPA05002332A/es active IP Right Grant
- 2003-09-08 CN CNA038222205A patent/CN1681810A/zh active Pending
- 2003-09-08 HR HR20050250A patent/HRP20050250A2/xx not_active Application Discontinuation
- 2003-09-08 OA OA1200500075A patent/OA12926A/en unknown
- 2003-09-08 EP EP03797426A patent/EP1542994B1/en not_active Expired - Lifetime
- 2003-09-08 DE DE60327443T patent/DE60327443D1/de not_active Expired - Lifetime
- 2003-09-08 AT AT03797426T patent/ATE430147T1/de not_active IP Right Cessation
- 2003-09-08 AP AP2005003261A patent/AP2005003261A0/xx unknown
- 2003-09-08 ES ES03797426T patent/ES2323421T3/es not_active Expired - Lifetime
- 2003-09-08 BR BR0314383-0A patent/BR0314383A/pt not_active IP Right Cessation
- 2003-09-08 AU AU2003256003A patent/AU2003256003A1/en not_active Abandoned
- 2003-09-08 JP JP2004568899A patent/JP4518956B2/ja not_active Expired - Fee Related
- 2003-09-08 KR KR1020057004611A patent/KR20050057415A/ko not_active Ceased
- 2003-09-08 WO PCT/IB2003/003823 patent/WO2004026863A1/en not_active Ceased
- 2003-09-08 CA CA2499429A patent/CA2499429C/en not_active Expired - Fee Related
- 2003-09-08 PL PL03375975A patent/PL375975A1/xx not_active Application Discontinuation
- 2003-09-08 EA EA200500354A patent/EA200500354A1/ru unknown
- 2003-09-15 PA PA20038582701A patent/PA8582701A1/es unknown
- 2003-09-15 PE PE2003000939A patent/PE20040987A1/es not_active Application Discontinuation
- 2003-09-15 UY UY27978A patent/UY27978A1/es not_active Application Discontinuation
- 2003-09-16 AR ARP030103357A patent/AR041273A1/es unknown
- 2003-09-17 US US10/667,187 patent/US7273936B2/en not_active Expired - Fee Related
- 2003-09-17 TW TW092125637A patent/TW200413362A/zh unknown
2005
- 2005-02-24 IS IS7711A patent/IS7711A/is unknown
- 2005-03-15 CR CR7743A patent/CR7743A/es not_active Application Discontinuation
- 2005-03-16 CO CO05024531A patent/CO5550473A2/es not_active Application Discontinuation
- 2005-03-18 MA MA28157A patent/MA27443A1/fr unknown
- 2005-04-15 NO NO20051838A patent/NO20051838L/no unknown

Also Published As

Publication number	Publication date
IS7711A (is)	2005-02-24
PA8582701A1 (es)	2004-04-23
US7273936B2 (en)	2007-09-25
CA2499429C (en)	2010-09-21
NO20051838L (no)	2005-04-15
CA2499429A1 (en)	2004-04-01
ATE430147T1 (de)	2009-05-15
EP1542994B1 (en)	2009-04-29
TW200413362A (en)	2004-08-01
AR041273A1 (es)	2005-05-11
JP4518956B2 (ja)	2010-08-04
AU2003256003A1 (en)	2004-04-08
WO2004026863A8 (en)	2005-04-21
CR7743A (es)	2005-06-15
MA27443A1 (fr)	2005-07-01
CO5550473A2 (es)	2005-08-31
ES2323421T3 (es)	2009-07-15
WO2004026863A1 (en)	2004-04-01
UY27978A1 (es)	2004-04-30
BR0314383A (pt)	2005-07-19
DE60327443D1 (de)	2009-06-10
AP2005003261A0 (en)	2005-03-31
EP1542994A1 (en)	2005-06-22
PE20040987A1 (es)	2004-12-27
CN1681810A (zh)	2005-10-12
HRP20050250A2 (en)	2005-10-31
EA200500354A1 (ru)	2005-10-27
PL375975A1 (en)	2005-12-12
JP2006502235A (ja)	2006-01-19
MXPA05002332A (es)	2005-06-08
KR20050057415A (ko)	2005-06-16
US20040110797A1 (en)	2004-06-10

Publication	Publication Date	Title
OA12926A (en)	2006-10-13	Novel oxazole and thiazole compounds as transforming growth factor (TGF) inhibitors.
CA2498047C (en)	2009-05-19	Novel imidazole compounds as transforming growth factor (tgf) inhibitors
EP1606267B1 (en)	2008-07-30	Pyrazine compounds as transforming growth factor (tgf) inhibitors
CA2496295C (en)	2010-11-23	Novels pyrazole compounds as transforming growth factor (tgf) inhibitors
US7053095B2 (en)	2006-05-30	Triazole compounds as transforming growth factor (TGF) inhibitors
US7030125B2 (en)	2006-04-18	Isothiazole and isoxazole compounds as transforming growth factor (TGF) inhibitors
US20040176390A1 (en)	2004-09-09	Novel fused heteroaromatic compounds as transforming growth factor (TGF) inhibitors
ZA200502277B (en)	2006-02-22	Novel isothiazole and isoxazole compounds as transforming growth factor (TGF) inhibitors.