ES2259707T3 - Oxazolo y furopirimidinas y su uso en medicamentos contra tumores. - Google Patents
Oxazolo y furopirimidinas y su uso en medicamentos contra tumores.Info
- Publication number
- ES2259707T3 ES2259707T3 ES02740590T ES02740590T ES2259707T3 ES 2259707 T3 ES2259707 T3 ES 2259707T3 ES 02740590 T ES02740590 T ES 02740590T ES 02740590 T ES02740590 T ES 02740590T ES 2259707 T3 ES2259707 T3 ES 2259707T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- formula
- aryl
- compound
- substituted
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- 239000003814 drug Substances 0.000 title description 12
- 229940079593 drug Drugs 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 185
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 84
- 150000003839 salts Chemical class 0.000 claims description 79
- -1 phenyloxy Chemical group 0.000 claims description 72
- 229910052757 nitrogen Inorganic materials 0.000 claims description 59
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 57
- 150000003254 radicals Chemical class 0.000 claims description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 43
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 36
- 125000003545 alkoxy group Chemical group 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 29
- 238000011282 treatment Methods 0.000 claims description 29
- 201000010099 disease Diseases 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 239000000460 chlorine Substances 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000003282 alkyl amino group Chemical group 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
- 125000006239 protecting group Chemical group 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 15
- 229910052740 iodine Inorganic materials 0.000 claims description 15
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 14
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 14
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 241001465754 Metazoa Species 0.000 claims description 12
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000004423 acyloxy group Chemical group 0.000 claims description 8
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 230000001225 therapeutic effect Effects 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 4
- 125000006392 alkylpyrimidinyl group Chemical group 0.000 claims description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 125000005111 carboxyalkoxy group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 4
- 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 description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 3
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 3
- 125000006542 morpholinylalkyl group Chemical group 0.000 claims description 3
- DTTFRMNZXXENIL-UHFFFAOYSA-N n-(4-chloro-2-fluorophenyl)-6-(4-nitrophenyl)furo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(OC1=NC=N2)=CC1=C2NC1=CC=C(Cl)C=C1F DTTFRMNZXXENIL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 2
- 230000003211 malignant effect Effects 0.000 claims description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- GSTJBBSRLNLTKK-UHFFFAOYSA-N 2-methoxy-5-[[6-(4-nitrophenyl)furo[2,3-d]pyrimidin-4-yl]amino]phenol Chemical compound C1=C(O)C(OC)=CC=C1NC1=NC=NC2=C1C=C(C=1C=CC(=CC=1)[N+]([O-])=O)O2 GSTJBBSRLNLTKK-UHFFFAOYSA-N 0.000 claims 1
- UUXZECBYDSQGLX-UHFFFAOYSA-N 2-methyl-5-[[6-(4-nitrophenyl)furo[2,3-d]pyrimidin-4-yl]amino]phenol Chemical compound C1=C(O)C(C)=CC=C1NC1=NC=NC2=C1C=C(C=1C=CC(=CC=1)[N+]([O-])=O)O2 UUXZECBYDSQGLX-UHFFFAOYSA-N 0.000 claims 1
- PQARUYUDPNVJBQ-UHFFFAOYSA-N 3-n-[6-(4-aminophenyl)furo[2,3-d]pyrimidin-4-yl]benzene-1,3-diamine Chemical compound C1=CC(N)=CC=C1C(OC1=NC=N2)=CC1=C2NC1=CC=CC(N)=C1 PQARUYUDPNVJBQ-UHFFFAOYSA-N 0.000 claims 1
- XWVBJTPNSNOTEI-UHFFFAOYSA-N 3-n-[6-(4-nitrophenyl)furo[2,3-d]pyrimidin-4-yl]benzene-1,3-diamine Chemical compound NC1=CC=CC(NC=2C=3C=C(OC=3N=CN=2)C=2C=CC(=CC=2)[N+]([O-])=O)=C1 XWVBJTPNSNOTEI-UHFFFAOYSA-N 0.000 claims 1
- AMRYRYMYUDVMAM-UHFFFAOYSA-N 5-[[6-(4-aminophenyl)furo[2,3-d]pyrimidin-4-yl]amino]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1NC1=NC=NC2=C1C=C(C=1C=CC(N)=CC=1)O2 AMRYRYMYUDVMAM-UHFFFAOYSA-N 0.000 claims 1
- AYRQJDRCBAQZCZ-UHFFFAOYSA-N 5-[[6-(4-aminophenyl)furo[2,3-d]pyrimidin-4-yl]amino]-2-methylphenol Chemical compound C1=C(O)C(C)=CC=C1NC1=NC=NC2=C1C=C(C=1C=CC(N)=CC=1)O2 AYRQJDRCBAQZCZ-UHFFFAOYSA-N 0.000 claims 1
- JXUCYSZHENOIEH-UHFFFAOYSA-N 6-(4-aminophenyl)-n-(3-chlorophenyl)furo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(N)=CC=C1C(OC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 JXUCYSZHENOIEH-UHFFFAOYSA-N 0.000 claims 1
- PGMTWCVXWQKSIQ-UHFFFAOYSA-N 6-(4-aminophenyl)-n-(4-chloro-2-fluorophenyl)furo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(N)=CC=C1C(OC1=NC=N2)=CC1=C2NC1=CC=C(Cl)C=C1F PGMTWCVXWQKSIQ-UHFFFAOYSA-N 0.000 claims 1
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims 1
- 238000003745 diagnosis Methods 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
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- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 230000001228 trophic effect Effects 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
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- 230000002792 vascular Effects 0.000 description 1
- 229950000578 vatalanib Drugs 0.000 description 1
- YCOYDOIWSSHVCK-UHFFFAOYSA-N vatalanib Chemical compound C1=CC(Cl)=CC=C1NC(C1=CC=CC=C11)=NN=C1CC1=CC=NC=C1 YCOYDOIWSSHVCK-UHFFFAOYSA-N 0.000 description 1
- 230000007998 vessel formation Effects 0.000 description 1
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- 239000002699 waste material Substances 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
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- XRASPMIURGNCCH-UHFFFAOYSA-N zoledronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CN1C=CN=C1 XRASPMIURGNCCH-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—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
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH87301/01 | 2001-05-14 | ||
| CH8732001 | 2001-05-14 |
Publications (1)
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|---|---|
| ES2259707T3 true ES2259707T3 (es) | 2006-10-16 |
Family
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| Application Number | Title | Priority Date | Filing Date |
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| ES02740590T Expired - Lifetime ES2259707T3 (es) | 2001-05-14 | 2002-05-13 | Oxazolo y furopirimidinas y su uso en medicamentos contra tumores. |
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|---|---|
| US (1) | US7294633B2 (cg-RX-API-DMAC10.html) |
| EP (1) | EP1390371B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JP4155827B2 (cg-RX-API-DMAC10.html) |
| CN (1) | CN100378107C (cg-RX-API-DMAC10.html) |
| AT (1) | ATE319718T1 (cg-RX-API-DMAC10.html) |
| BR (1) | BR0209645A (cg-RX-API-DMAC10.html) |
| CA (1) | CA2449188A1 (cg-RX-API-DMAC10.html) |
| DE (1) | DE60209721T2 (cg-RX-API-DMAC10.html) |
| DK (1) | DK1390371T3 (cg-RX-API-DMAC10.html) |
| ES (1) | ES2259707T3 (cg-RX-API-DMAC10.html) |
| PT (1) | PT1390371E (cg-RX-API-DMAC10.html) |
| WO (1) | WO2002092603A1 (cg-RX-API-DMAC10.html) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP1689753A4 (en) * | 2003-12-04 | 2010-07-07 | Glaxosmithkline Llc | NEW CHEMICAL COMPOUNDS |
| KR20050091462A (ko) * | 2004-03-12 | 2005-09-15 | 한국과학기술연구원 | 푸로피리미딘 화합물 및 이를 포함하는 ｄｄｒ2 티로신키나아제 활성 저해제 |
| JPWO2005095419A1 (ja) * | 2004-04-01 | 2008-02-21 | 武田薬品工業株式会社 | チアゾロピリミジン誘導体 |
| EP1874769B1 (de) | 2005-04-25 | 2011-09-14 | Merck Patent GmbH | Neuartige aza-heterozyklen als kinase-inhibitoren |
| DE102005061170A1 (de) | 2005-12-21 | 2007-07-05 | Bayer Healthcare Ag | Neue, acyclisch substituierte Furopyrimidin-Derivate und ihre Verwendung |
| DE102005061171A1 (de) | 2005-12-21 | 2007-07-05 | Bayer Healthcare Ag | Neue, cyclisch substituierte Furopyrimidin-Derivate und ihre Verwendung |
| EP3219319A1 (en) * | 2006-06-22 | 2017-09-20 | Nippon Chemiphar Co., Ltd. | Agent for overcoming resistance to anti-cancer agent |
| DE102007019691A1 (de) | 2007-04-26 | 2008-10-30 | Bayer Healthcare Ag | Verwendung von acyclisch substituierten Furopyrimidin-Derivaten zur Behandlung der pulmonalen arteriellen Hypertonie |
| DE102007019690A1 (de) | 2007-04-26 | 2008-10-30 | Bayer Healthcare Ag | Verwendung von cyclisch substituierten Furopyrimidin-Derivaten zur Behandlung der pulmonalen arteriellen Hypertonie |
| DE102007027799A1 (de) | 2007-06-16 | 2008-12-18 | Bayer Healthcare Ag | Substituierte Furopyrimidine und ihre Verwendung |
| DE102007027800A1 (de) | 2007-06-16 | 2008-12-18 | Bayer Healthcare Ag | Substituierte bicyclische Heteroaryl-Verbindungen und ihre Verwendung |
| RU2345996C1 (ru) * | 2007-07-17 | 2009-02-10 | Андрей Александрович Иващенко | Аннелированные азагетероциклические амиды, включающие пиримидиновый фрагмент, способ их получения и применения |
| EP2318415B1 (en) * | 2008-07-15 | 2013-02-20 | Sanofi | Oxazolopyrimidines as edg-1 receptor agonists |
| UY32240A (es) | 2008-11-14 | 2010-06-30 | Boeringer Ingelheim Kg | Nuevas 2,4-diaminopirimidinas, sus sales farmacéuticamente aceptables, composiciones conteniéndolas y aplicaciones. |
| CN101899057A (zh) * | 2010-07-21 | 2010-12-01 | 中国药科大学 | 嘧啶并噁唑衍生物的一种制备方法及其在医学上的用途 |
| US8907093B2 (en) * | 2011-07-07 | 2014-12-09 | Sanofi | Carboxylic acid derivatives having an oxazolo[4,5-c]pyridine ring |
| US8580816B2 (en) * | 2011-07-07 | 2013-11-12 | Sanofi | Carboxylic acid derivatives having an oxazolo[5,4-b]pyridine ring |
| CN103087077B (zh) * | 2011-11-03 | 2016-05-18 | 上海希迈医药科技有限公司 | 噻吩并嘧啶和呋喃并嘧啶类衍生物、其制备方法及其在医药上的应用 |
| CN103360407B (zh) * | 2012-04-10 | 2016-06-22 | 上海希迈医药科技有限公司 | 一种噻吩并嘧啶类衍生物、其制备方法及其在医药上的应用 |
| WO2015162518A1 (en) | 2014-04-25 | 2015-10-29 | Pfizer Inc. | Heteroaromatic compounds and their use as dopamine d1 ligands |
| CN104650111A (zh) * | 2015-01-14 | 2015-05-27 | 中国药科大学 | 芳基脲及芳基酰胺取代的噁唑并嘧啶类化合物及其制备和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5137879A (en) | 1990-03-30 | 1992-08-11 | Dowelanco | Furopyrimidin-4-imine derivatives |
| US5227387A (en) * | 1991-09-03 | 1993-07-13 | Dowelanco | Quinoline nematicidal method |
| ES2109796T3 (es) | 1994-05-03 | 1998-01-16 | Ciba Geigy Ag | Derivados de pirrolopirimidilo con efecto antiproliferante. |
| JPH1184248A (ja) * | 1997-09-12 | 1999-03-26 | Nikon Corp | 反射屈折縮小光学系 |
| KR100600550B1 (ko) * | 2000-10-20 | 2006-07-13 | 에자이 가부시키가이샤 | 질소 함유 방향환 유도체 |
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2002
- 2002-05-13 CA CA002449188A patent/CA2449188A1/en not_active Abandoned
- 2002-05-13 BR BR0209645-5A patent/BR0209645A/pt not_active IP Right Cessation
- 2002-05-13 AT AT02740590T patent/ATE319718T1/de active
- 2002-05-13 ES ES02740590T patent/ES2259707T3/es not_active Expired - Lifetime
- 2002-05-13 DE DE60209721T patent/DE60209721T2/de not_active Expired - Lifetime
- 2002-05-13 EP EP02740590A patent/EP1390371B1/en not_active Expired - Lifetime
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- 2002-05-13 US US10/476,818 patent/US7294633B2/en not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| US20040152892A1 (en) | 2004-08-05 |
| CN1509291A (zh) | 2004-06-30 |
| DK1390371T3 (da) | 2006-06-19 |
| WO2002092603A1 (en) | 2002-11-21 |
| JP4155827B2 (ja) | 2008-09-24 |
| BR0209645A (pt) | 2004-07-06 |
| EP1390371B1 (en) | 2006-03-08 |
| PT1390371E (pt) | 2006-07-31 |
| DE60209721D1 (de) | 2006-05-04 |
| JP2005508855A (ja) | 2005-04-07 |
| CA2449188A1 (en) | 2002-11-21 |
| US7294633B2 (en) | 2007-11-13 |
| ATE319718T1 (de) | 2006-03-15 |
| EP1390371A1 (en) | 2004-02-25 |
| DE60209721T2 (de) | 2006-09-07 |
| CN100378107C (zh) | 2008-04-02 |
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