BG107002A - Птеридинови съединения за лечение на псориазис - Google Patents

Птеридинови съединения за лечение на псориазис Download PDF

Info

Publication number: BG107002A
Authority: BG; Bulgaria
Prior art keywords: thio; amino; pteridinone; group; methyl
Prior art date: 2000-02-23

Application number

BG107002A

Other languages

Bulgarian (bg)

English (en)

Inventor

Roger Bonnert

Stewart Gardiner

Fraser Hunt

Iain Walters

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.)

2000-02-23

Filing date

2002-08-14

Publication date

2003-04-30

2002-08-14 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2003-04-30 Publication of BG107002A publication Critical patent/BG107002A/bg

Links

201000004681 Psoriasis Diseases 0.000 title claims description 10
125000001042 pteridinyl group Chemical class N1=C(N=CC2=NC=CN=C12)* 0.000 title abstract 2
238000000034 method Methods 0.000 claims abstract description 76
238000002360 preparation method Methods 0.000 claims abstract description 20
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
238000002560 therapeutic procedure Methods 0.000 claims abstract description 11
-1 2,3-difluorophenyl Chemical group 0.000 claims description 211
150000001875 compounds Chemical class 0.000 claims description 191
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 191
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 157
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 85
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 71
125000001424 substituent group Chemical group 0.000 claims description 62
125000005843 halogen group Chemical group 0.000 claims description 57
150000003839 salts Chemical class 0.000 claims description 39
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 35
239000012453 solvate Substances 0.000 claims description 32
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 29
201000010099 disease Diseases 0.000 claims description 29
238000006243 chemical reaction Methods 0.000 claims description 27
239000001257 hydrogen Substances 0.000 claims description 26
229910052739 hydrogen Inorganic materials 0.000 claims description 26
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 25
102000019034 Chemokines Human genes 0.000 claims description 18
108010012236 Chemokines Proteins 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 16
229910052757 nitrogen Inorganic materials 0.000 claims description 16
229910052760 oxygen Inorganic materials 0.000 claims description 15
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 14
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 12
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
125000002837 carbocyclic group Chemical group 0.000 claims description 11
OOIPDYWPGUHUJW-UHFFFAOYSA-N 8h-pteridin-7-one Chemical compound C1=NC=NC2=NC(O)=CN=C21 OOIPDYWPGUHUJW-UHFFFAOYSA-N 0.000 claims description 10
102000009410 Chemokine receptor Human genes 0.000 claims description 10
108050000299 Chemokine receptor Proteins 0.000 claims description 10
102000002791 Interleukin-8B Receptors Human genes 0.000 claims description 10
108010018951 Interleukin-8B Receptors Proteins 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
229910052717 sulfur Inorganic materials 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 9
239000000654 additive Substances 0.000 claims description 9
230000000996 additive effect Effects 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 9
125000004429 atom Chemical group 0.000 claims description 9
239000003085 diluting agent Substances 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 9
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
125000001072 heteroaryl group Chemical group 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 7
ALHFTXQQJSWTIT-UHFFFAOYSA-N 2-[(2,3-difluorophenyl)methylsulfanyl]-4-(2-hydroxyethylamino)-8h-pteridin-7-one Chemical compound N=1C=2NC(=O)C=NC=2C(NCCO)=NC=1SCC1=CC=CC(F)=C1F ALHFTXQQJSWTIT-UHFFFAOYSA-N 0.000 claims description 6
LUXKMKJKXOMEAN-UHFFFAOYSA-N 2-[(2,3-difluorophenyl)methylsulfanyl]-4-[[3-(dimethylamino)-2,2-dimethylpropyl]amino]-8h-pteridin-7-one Chemical compound N=1C=2NC(=O)C=NC=2C(NCC(C)(C)CN(C)C)=NC=1SCC1=CC=CC(F)=C1F LUXKMKJKXOMEAN-UHFFFAOYSA-N 0.000 claims description 6
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
125000004122 cyclic group Chemical group 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
238000011282 treatment Methods 0.000 claims description 6
125000004494 ethyl ester group Chemical group 0.000 claims description 5
230000001404 mediated effect Effects 0.000 claims description 5
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 4
JNHYIZYGISWLSL-UHFFFAOYSA-N 2-[(3-chloro-2-fluorophenyl)methylsulfanyl]-4-(1,3-dihydroxypropan-2-ylamino)-8h-pteridin-7-one Chemical compound N=1C=2NC(=O)C=NC=2C(NC(CO)CO)=NC=1SCC1=CC=CC(Cl)=C1F JNHYIZYGISWLSL-UHFFFAOYSA-N 0.000 claims description 4
SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
230000033115 angiogenesis Effects 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 4
238000002156 mixing Methods 0.000 claims description 4
RIZMZPFNCPWNAH-SNVBAGLBSA-N 2-[(2-fluoro-3-methylphenyl)methylsulfanyl]-4-[[(2r)-1-hydroxypropan-2-yl]amino]-8h-pteridin-7-one Chemical compound N=1C=2NC(=O)C=NC=2C(N[C@@H](CO)C)=NC=1SCC1=CC=CC(C)=C1F RIZMZPFNCPWNAH-SNVBAGLBSA-N 0.000 claims description 3
MPGKKVURGBVKGW-UHFFFAOYSA-N 2-[(3-chloro-2-fluorophenyl)methylsulfanyl]-4-(2-hydroxyethylamino)-8h-pteridin-7-one Chemical compound N=1C=2NC(=O)C=NC=2C(NCCO)=NC=1SCC1=CC=CC(Cl)=C1F MPGKKVURGBVKGW-UHFFFAOYSA-N 0.000 claims description 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
OKTVAUNSMLMTBE-UHFFFAOYSA-N 4-(1,3-dihydroxypropan-2-ylamino)-2-(thiophen-2-ylmethylsulfanyl)-8h-pteridin-7-one Chemical compound N=1C=2NC(=O)C=NC=2C(NC(CO)CO)=NC=1SCC1=CC=CS1 OKTVAUNSMLMTBE-UHFFFAOYSA-N 0.000 claims description 3
VODJJGQOLOEIRR-UHFFFAOYSA-N 4-(2-aminoethylamino)-2-[[2-fluoro-3-(trifluoromethyl)phenyl]methylsulfanyl]-8h-pteridin-7-one Chemical compound N=1C=2NC(=O)C=NC=2C(NCCN)=NC=1SCC1=CC=CC(C(F)(F)F)=C1F VODJJGQOLOEIRR-UHFFFAOYSA-N 0.000 claims description 3
230000015572 biosynthetic process Effects 0.000 claims description 3
208000027866 inflammatory disease Diseases 0.000 claims description 3
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 3
RXPRXSUPVUTRNH-UHFFFAOYSA-N 2-[(2,3-difluorophenyl)methylsulfanyl]-4-[(1,3-dihydroxy-2-methylpropan-2-yl)amino]-8h-pteridin-7-one Chemical compound N=1C=2NC(=O)C=NC=2C(NC(CO)(CO)C)=NC=1SCC1=CC=CC(F)=C1F RXPRXSUPVUTRNH-UHFFFAOYSA-N 0.000 claims description 2
FFWWPOSWGBRMAI-SECBINFHSA-N 2-[(2-fluorophenyl)methylsulfanyl]-4-[[(2r)-1-hydroxypropan-2-yl]amino]-8h-pteridin-7-one Chemical compound N=1C=2NC(=O)C=NC=2C(N[C@@H](CO)C)=NC=1SCC1=CC=CC=C1F FFWWPOSWGBRMAI-SECBINFHSA-N 0.000 claims description 2
QPYBUNKIFZAIGH-MRVPVSSYSA-N 2-[(3-chloro-2-fluorophenyl)methylsulfanyl]-4-[[(2r)-1-hydroxypropan-2-yl]amino]-8h-pteridin-7-one Chemical compound N=1C=2NC(=O)C=NC=2C(N[C@@H](CO)C)=NC=1SCC1=CC=CC(Cl)=C1F QPYBUNKIFZAIGH-MRVPVSSYSA-N 0.000 claims description 2
JIKISISMEWPQJK-SECBINFHSA-N 2-[(3-fluoro-2-methoxyphenyl)methylsulfanyl]-4-[[(2r)-1-hydroxypropan-2-yl]amino]-8h-pteridin-7-one Chemical compound COC1=C(F)C=CC=C1CSC1=NC(N[C@H](C)CO)=C(N=CC(=O)N2)C2=N1 JIKISISMEWPQJK-SECBINFHSA-N 0.000 claims description 2
WVNDNQWPAYCUBF-UHFFFAOYSA-N 2-[[2-fluoro-3-(trifluoromethyl)phenyl]methylsulfanyl]-4-(2-hydroxyethylamino)-8h-pteridin-7-one Chemical compound N=1C=2NC(=O)C=NC=2C(NCCO)=NC=1SCC1=CC=CC(C(F)(F)F)=C1F WVNDNQWPAYCUBF-UHFFFAOYSA-N 0.000 claims description 2
INAJFJAOCLCRBN-UHFFFAOYSA-N 4-(2-aminoethylamino)-2-[(3-chloro-4-methoxyphenyl)methylsulfanyl]-8h-pteridin-7-one Chemical compound C1=C(Cl)C(OC)=CC=C1CSC1=NC(NCCN)=C(N=CC(=O)N2)C2=N1 INAJFJAOCLCRBN-UHFFFAOYSA-N 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
150000003573 thiols Chemical class 0.000 claims description 2
238000006467 substitution reaction Methods 0.000 claims 3
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 2
108091008928 CXC chemokine receptors Proteins 0.000 claims 2
102000054900 CXCR Receptors Human genes 0.000 claims 2
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 2
ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 2
SKTGDFBTGFNMBY-UHFFFAOYSA-N 2-[(2,3-difluorophenyl)methylsulfanyl]-4-(6-hydroxyhexylamino)-8h-pteridin-7-one Chemical compound N=1C=2NC(=O)C=NC=2C(NCCCCCCO)=NC=1SCC1=CC=CC(F)=C1F SKTGDFBTGFNMBY-UHFFFAOYSA-N 0.000 claims 1
AHVAHTPEQANPQA-MRVPVSSYSA-N 2-[(2,3-difluorophenyl)methylsulfanyl]-4-[[(2r)-1-hydroxypropan-2-yl]amino]-6-methyl-8h-pteridin-7-one Chemical compound N=1C=2NC(=O)C(C)=NC=2C(N[C@@H](CO)C)=NC=1SCC1=CC=CC(F)=C1F AHVAHTPEQANPQA-MRVPVSSYSA-N 0.000 claims 1
AUCIFDXEQXEVMR-UHFFFAOYSA-N 2-[(3-chloro-4-methoxyphenyl)methylsulfanyl]-4-(1,3-dihydroxypropan-2-ylamino)-8h-pteridin-7-one;hydrochloride Chemical compound Cl.C1=C(Cl)C(OC)=CC=C1CSC1=NC(NC(CO)CO)=C(N=CC(=O)N2)C2=N1 AUCIFDXEQXEVMR-UHFFFAOYSA-N 0.000 claims 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
MEUIOCMLELSKDI-MRVPVSSYSA-N 4-[[(2r)-1-hydroxypropan-2-yl]amino]-2-[(5-methylfuran-2-yl)methylsulfanyl]-8h-pteridin-7-one Chemical compound N=1C=2NC(=O)C=NC=2C(N[C@@H](CO)C)=NC=1SCC1=CC=C(C)O1 MEUIOCMLELSKDI-MRVPVSSYSA-N 0.000 claims 1
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
ZWIFHIVJBVYSOJ-SBSPUUFOSA-N FC1=C(C=CC(=C1)OC)CSC1=NC=2NC(C=NC2C(=N1)N[C@@H](CO)C)=O.FC(C(=O)O)(F)F Chemical compound FC1=C(C=CC(=C1)OC)CSC1=NC=2NC(C=NC2C(=N1)N[C@@H](CO)C)=O.FC(C(=O)O)(F)F ZWIFHIVJBVYSOJ-SBSPUUFOSA-N 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 claims 1
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 179
238000004949 mass spectrometry Methods 0.000 description 108
239000000047 product Substances 0.000 description 76
238000005481 NMR spectroscopy Methods 0.000 description 54
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
239000000243 solution Substances 0.000 description 37
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 35
239000007787 solid Substances 0.000 description 34
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
239000000203 mixture Substances 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
239000002904 solvent Substances 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 16
238000001914 filtration Methods 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 12
206010039083 rhinitis Diseases 0.000 description 12
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
239000011734 sodium Substances 0.000 description 11
239000002585 base Substances 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
238000010992 reflux Methods 0.000 description 10
229910052708 sodium Inorganic materials 0.000 description 10
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 9
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HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 8
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208000035475 disorder Diseases 0.000 description 6
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238000003556 assay Methods 0.000 description 5
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
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Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
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Diabetes (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

BG107002A 2000-02-23 2002-08-14 Птеридинови съединения за лечение на псориазис BG107002A (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB0004128A GB2359551A (en)	2000-02-23	2000-02-23	Pharmaceutically active pyrimidine derivatives
PCT/SE2001/000374 WO2001062758A1 (en)	2000-02-23	2001-02-20	Pteridine compounds for the treatment of psoriasis

Publications (1)

Publication Number	Publication Date
BG107002A true BG107002A (bg)	2003-04-30

Family

ID=9886153

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG107002A BG107002A (bg)	2000-02-23	2002-08-14	Птеридинови съединения за лечение на псориазис

Country Status (32)

Country	Link
US (2)	US6875868B2 (xx)
EP (1)	EP1259512B1 (xx)
JP (1)	JP2003524012A (xx)
KR (1)	KR100795758B1 (xx)
CN (1)	CN1190437C (xx)
AR (1)	AR029805A1 (xx)
AT (1)	ATE250605T1 (xx)
AU (1)	AU782509B2 (xx)
BG (1)	BG107002A (xx)
BR (1)	BR0108600A (xx)
CA (1)	CA2400217C (xx)
CO (1)	CO5290258A1 (xx)
CZ (1)	CZ20022839A3 (xx)
DE (1)	DE60100851T2 (xx)
DK (1)	DK1259512T3 (xx)
EE (1)	EE200200461A (xx)
ES (1)	ES2206402T3 (xx)
GB (1)	GB2359551A (xx)
HU (1)	HUP0204399A3 (xx)
IL (2)	IL151132A0 (xx)
IS (1)	IS6491A (xx)
MX (1)	MXPA02008233A (xx)
NO (1)	NO329898B1 (xx)
NZ (1)	NZ520355A (xx)
PL (1)	PL358004A1 (xx)
PT (1)	PT1259512E (xx)
RU (1)	RU2002125451A (xx)
SK (1)	SK12152002A3 (xx)
TR (1)	TR200302214T4 (xx)
UA (1)	UA72590C2 (xx)
WO (1)	WO2001062758A1 (xx)
ZA (1)	ZA200206590B (xx)

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2000
- 2000-02-23 GB GB0004128A patent/GB2359551A/en not_active Withdrawn
2001
- 2001-02-20 UA UA2002097583A patent/UA72590C2/uk unknown
- 2001-02-20 IL IL15113201A patent/IL151132A0/xx unknown
- 2001-02-20 RU RU2002125451/04A patent/RU2002125451A/ru not_active Application Discontinuation
- 2001-02-20 DE DE60100851T patent/DE60100851T2/de not_active Expired - Lifetime
- 2001-02-20 DK DK01906493T patent/DK1259512T3/da active
- 2001-02-20 CA CA002400217A patent/CA2400217C/en not_active Expired - Fee Related
- 2001-02-20 KR KR1020027011047A patent/KR100795758B1/ko not_active Expired - Fee Related
- 2001-02-20 CZ CZ20022839A patent/CZ20022839A3/cs unknown
- 2001-02-20 BR BR0108600-6A patent/BR0108600A/pt not_active Application Discontinuation
- 2001-02-20 EP EP01906493A patent/EP1259512B1/en not_active Expired - Lifetime
- 2001-02-20 TR TR2003/02214T patent/TR200302214T4/xx unknown
- 2001-02-20 AT AT01906493T patent/ATE250605T1/de active
- 2001-02-20 EE EEP200200461A patent/EE200200461A/xx unknown
- 2001-02-20 NZ NZ520355A patent/NZ520355A/en not_active IP Right Cessation
- 2001-02-20 PT PT01906493T patent/PT1259512E/pt unknown
- 2001-02-20 WO PCT/SE2001/000374 patent/WO2001062758A1/en not_active Ceased
- 2001-02-20 SK SK1215-2002A patent/SK12152002A3/sk unknown
- 2001-02-20 HU HU0204399A patent/HUP0204399A3/hu unknown
- 2001-02-20 MX MXPA02008233A patent/MXPA02008233A/es active IP Right Grant
- 2001-02-20 CN CNB018054676A patent/CN1190437C/zh not_active Expired - Fee Related
- 2001-02-20 JP JP2001562540A patent/JP2003524012A/ja active Pending
- 2001-02-20 ES ES01906493T patent/ES2206402T3/es not_active Expired - Lifetime
- 2001-02-20 PL PL01358004A patent/PL358004A1/xx not_active Application Discontinuation
- 2001-02-20 US US10/204,814 patent/US6875868B2/en not_active Expired - Fee Related
- 2001-02-20 AU AU34316/01A patent/AU782509B2/en not_active Ceased
- 2001-02-21 AR ARP010100773A patent/AR029805A1/es not_active Application Discontinuation
- 2001-02-21 CO CO01013781A patent/CO5290258A1/es not_active Application Discontinuation
2002
- 2002-08-07 IS IS6491A patent/IS6491A/is unknown
- 2002-08-07 IL IL151132A patent/IL151132A/en not_active IP Right Cessation
- 2002-08-14 BG BG107002A patent/BG107002A/bg unknown
- 2002-08-16 ZA ZA200206590A patent/ZA200206590B/en unknown
- 2002-08-22 NO NO20024005A patent/NO329898B1/no not_active IP Right Cessation
2004
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Also Published As

Publication number	Publication date
CO5290258A1 (es)	2003-06-27
WO2001062758A1 (en)	2001-08-30
RU2002125451A (ru)	2004-01-10
EP1259512A1 (en)	2002-11-27
NO20024005D0 (no)	2002-08-22
UA72590C2 (uk)	2005-03-15
DE60100851D1 (de)	2003-10-30
HUP0204399A2 (en)	2003-05-28
EE200200461A (et)	2003-12-15
IL151132A (en)	2010-11-30
KR20030005207A (ko)	2003-01-17
US20050171345A1 (en)	2005-08-04
AU3431601A (en)	2001-09-03
HK1050899A1 (en)	2003-07-11
SK12152002A3 (sk)	2003-03-04
CA2400217A1 (en)	2001-08-30
US20030055250A1 (en)	2003-03-20
DK1259512T3 (da)	2003-12-29
PL358004A1 (en)	2004-08-09
ZA200206590B (en)	2003-11-17
AU782509B2 (en)	2005-08-04
IS6491A (is)	2002-08-07
DE60100851T2 (de)	2004-07-15
KR100795758B1 (ko)	2008-01-21
GB2359551A (en)	2001-08-29
JP2003524012A (ja)	2003-08-12
IL151132A0 (en)	2003-04-10
ATE250605T1 (de)	2003-10-15
NO20024005L (no)	2002-10-22
CA2400217C (en)	2009-02-17
NO329898B1 (no)	2011-01-24
CZ20022839A3 (cs)	2002-11-13
AR029805A1 (es)	2003-07-16
NZ520355A (en)	2005-01-28
GB0004128D0 (en)	2000-04-12
PT1259512E (pt)	2004-02-27
EP1259512B1 (en)	2003-09-24
BR0108600A (pt)	2002-11-12
US7579342B2 (en)	2009-08-25
HUP0204399A3 (en)	2004-11-29
ES2206402T3 (es)	2004-05-16
US6875868B2 (en)	2005-04-05
CN1404482A (zh)	2003-03-19
TR200302214T4 (tr)	2004-01-21
CN1190437C (zh)	2005-02-23
MXPA02008233A (es)	2004-04-05

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