ES2648233T3 - Derivados de triazol bicíclico para el tratamiento de tumores - Google Patents
Derivados de triazol bicíclico para el tratamiento de tumores Download PDFInfo
- Publication number
- ES2648233T3 ES2648233T3 ES09777234.7T ES09777234T ES2648233T3 ES 2648233 T3 ES2648233 T3 ES 2648233T3 ES 09777234 T ES09777234 T ES 09777234T ES 2648233 T3 ES2648233 T3 ES 2648233T3
- Authority
- ES
- Spain
- Prior art keywords
- pyrimidin
- triazolo
- benzyl
- bromo
- pyrazin
- 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.)
- Active
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- 206010028980 Neoplasm Diseases 0.000 title description 4
- 238000011282 treatment Methods 0.000 title description 4
- 125000002619 bicyclic group Chemical group 0.000 title 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- -1 p iridinyl Chemical group 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims description 32
- 238000002360 preparation method Methods 0.000 claims description 8
- AQNDPWVEOIINEC-UHFFFAOYSA-N 2-[3-[[5-(1-methylpyrazol-4-yl)triazolo[4,5-b]pyrazin-3-yl]methyl]phenyl]pyrimidin-5-ol Chemical compound C1=NN(C)C=C1C1=CN=C(N=NN2CC=3C=C(C=CC=3)C=3N=CC(O)=CN=3)C2=N1 AQNDPWVEOIINEC-UHFFFAOYSA-N 0.000 claims description 2
- NWCOAJYSIYJCTB-UHFFFAOYSA-N 2-[3-[[3-(1-hydroxy-2h-pyrimidin-2-yl)phenyl]methyl]triazolo[4,5-b]pyrazin-5-yl]benzonitrile Chemical compound ON1C=CC=NC1C1=CC=CC(CN2C3=NC(=CN=C3N=N2)C=2C(=CC=CC=2)C#N)=C1 NWCOAJYSIYJCTB-UHFFFAOYSA-N 0.000 claims 1
- LBIUUHQFAWPVSB-UHFFFAOYSA-N 2-[3-[[5-(1-methylpyrazol-4-yl)oxytriazolo[4,5-b]pyrazin-3-yl]methyl]phenyl]pyrimidin-5-ol Chemical compound C1=NN(C)C=C1OC1=CN=C(N=NN2CC=3C=C(C=CC=3)C=3N=CC(O)=CN=3)C2=N1 LBIUUHQFAWPVSB-UHFFFAOYSA-N 0.000 claims 1
- CBCAPJKYNKWEBB-UHFFFAOYSA-N 2-[3-[[5-(3,5-difluorophenoxy)triazolo[4,5-b]pyrazin-3-yl]methyl]phenyl]pyrimidin-5-ol Chemical compound N1=CC(O)=CN=C1C1=CC=CC(CN2C3=NC(OC=4C=C(F)C=C(F)C=4)=CN=C3N=N2)=C1 CBCAPJKYNKWEBB-UHFFFAOYSA-N 0.000 claims 1
- OFGOWOFZYLUAJS-UHFFFAOYSA-N 2-[3-[[5-(3,5-difluorophenyl)triazolo[4,5-b]pyrazin-3-yl]methyl]phenyl]pyrimidin-5-ol Chemical compound N1=CC(O)=CN=C1C1=CC=CC(CN2C3=NC(=CN=C3N=N2)C=2C=C(F)C=C(F)C=2)=C1 OFGOWOFZYLUAJS-UHFFFAOYSA-N 0.000 claims 1
- DTQDASOUQDSZMN-UHFFFAOYSA-N 3-[3-[[3-(5-bromopyrimidin-2-yl)phenyl]methyl]triazolo[4,5-b]pyrazin-5-yl]benzonitrile Chemical compound N1=CC(Br)=CN=C1C1=CC=CC(CN2C3=NC(=CN=C3N=N2)C=2C=C(C=CC=2)C#N)=C1 DTQDASOUQDSZMN-UHFFFAOYSA-N 0.000 claims 1
- BTKHQZZEWJCYID-UHFFFAOYSA-N 3-[3-[[3-(5-hydroxypyrimidin-2-yl)phenyl]methyl]triazolo[4,5-b]pyrazin-5-yl]oxybenzonitrile Chemical compound N1=CC(O)=CN=C1C1=CC=CC(CN2C3=NC(OC=4C=C(C=CC=4)C#N)=CN=C3N=N2)=C1 BTKHQZZEWJCYID-UHFFFAOYSA-N 0.000 claims 1
- AUSMZAZQBSXZSK-UHFFFAOYSA-N 3-[[3-(5-bromopyrimidin-2-yl)phenyl]methyl]-5-(1-methylpyrazol-4-yl)oxytriazolo[4,5-b]pyrazine Chemical compound C1=NN(C)C=C1OC1=CN=C(N=NN2CC=3C=C(C=CC=3)C=3N=CC(Br)=CN=3)C2=N1 AUSMZAZQBSXZSK-UHFFFAOYSA-N 0.000 claims 1
- YDAJFHUEBTVWQC-UHFFFAOYSA-N 3-[[3-(5-bromopyrimidin-2-yl)phenyl]methyl]-5-(1-methylpyrazol-4-yl)triazolo[4,5-b]pyrazine Chemical compound C1=NN(C)C=C1C1=CN=C(N=NN2CC=3C=C(C=CC=3)C=3N=CC(Br)=CN=3)C2=N1 YDAJFHUEBTVWQC-UHFFFAOYSA-N 0.000 claims 1
- DUENYEDKUCQZOQ-UHFFFAOYSA-N 3-[[3-(5-bromopyrimidin-2-yl)phenyl]methyl]-5-(3,5-difluorophenoxy)triazolo[4,5-b]pyrazine Chemical compound FC1=CC(F)=CC(OC=2N=C3N(CC=4C=C(C=CC=4)C=4N=CC(Br)=CN=4)N=NC3=NC=2)=C1 DUENYEDKUCQZOQ-UHFFFAOYSA-N 0.000 claims 1
- FBRVBVVFNGBBAG-UHFFFAOYSA-N 3-[[3-(5-bromopyrimidin-2-yl)phenyl]methyl]-5-(3,5-difluorophenyl)triazolo[4,5-b]pyrazine Chemical compound FC1=CC(F)=CC(C=2N=C3N(CC=4C=C(C=CC=4)C=4N=CC(Br)=CN=4)N=NC3=NC=2)=C1 FBRVBVVFNGBBAG-UHFFFAOYSA-N 0.000 claims 1
- VMCNQFWMNVMRFQ-UHFFFAOYSA-N 4-[2-[2-[3-(benzotriazol-1-ylmethyl)phenyl]pyrimidin-5-yl]oxyethyl]morpholine Chemical compound C=1N=C(C=2C=C(CN3C4=CC=CC=C4N=N3)C=CC=2)N=CC=1OCCN1CCOCC1 VMCNQFWMNVMRFQ-UHFFFAOYSA-N 0.000 claims 1
- BQBBWSZGJSLDNL-UHFFFAOYSA-N 4-[2-[2-[3-(triazolo[4,5-b]pyridin-3-ylmethyl)phenyl]pyrimidin-5-yl]oxyethyl]morpholine Chemical compound C=1N=C(C=2C=C(CN3C4=NC=CC=C4N=N3)C=CC=2)N=CC=1OCCN1CCOCC1 BQBBWSZGJSLDNL-UHFFFAOYSA-N 0.000 claims 1
- WOCUYUZTBJPIBZ-UHFFFAOYSA-N 4-[2-[2-[3-[(5-bromotriazolo[4,5-b]pyrazin-3-yl)methyl]phenyl]pyrimidin-5-yl]oxyethyl]morpholine Chemical compound C12=NC(Br)=CN=C2N=NN1CC(C=1)=CC=CC=1C(N=C1)=NC=C1OCCN1CCOCC1 WOCUYUZTBJPIBZ-UHFFFAOYSA-N 0.000 claims 1
- VOXDGMYBKBCNRG-UHFFFAOYSA-N 4-[2-[2-[3-[(5-chlorobenzotriazol-1-yl)methyl]phenyl]pyrimidin-5-yl]oxyethyl]morpholine Chemical compound N1=NC2=CC(Cl)=CC=C2N1CC(C=1)=CC=CC=1C(N=C1)=NC=C1OCCN1CCOCC1 VOXDGMYBKBCNRG-UHFFFAOYSA-N 0.000 claims 1
- AORAPHGNWOPUBR-UHFFFAOYSA-N 4-[2-[2-[3-[[5-(1-methylpyrazol-4-yl)triazolo[4,5-b]pyrazin-3-yl]methyl]phenyl]pyrimidin-5-yl]oxyethyl]morpholine Chemical compound C1=NN(C)C=C1C1=CN=C(N=NN2CC=3C=C(C=CC=3)C=3N=CC(OCCN4CCOCC4)=CN=3)C2=N1 AORAPHGNWOPUBR-UHFFFAOYSA-N 0.000 claims 1
- AAADVTBBRYVXBN-UHFFFAOYSA-N 5-bromo-3-[[3-(5-bromopyrimidin-2-yl)phenyl]methyl]triazolo[4,5-b]pyrazine Chemical compound N1=CC(Br)=CN=C1C1=CC=CC(CN2C3=NC(Br)=CN=C3N=N2)=C1 AAADVTBBRYVXBN-UHFFFAOYSA-N 0.000 claims 1
- VJPDMATUILSPLZ-UHFFFAOYSA-N 5-bromo-n-[[3-[5-(2-morpholin-4-ylethoxy)pyrimidin-2-yl]phenyl]methyl]-2-nitroaniline Chemical compound [O-][N+](=O)C1=CC=C(Br)C=C1NCC1=CC=CC(C=2N=CC(OCCN3CCOCC3)=CN=2)=C1 VJPDMATUILSPLZ-UHFFFAOYSA-N 0.000 claims 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- KMUXNURNSDREAM-UHFFFAOYSA-N n,n-dimethyl-2-[2-[3-[[5-(1-methylpyrazol-4-yl)triazolo[4,5-b]pyrazin-3-yl]methyl]phenyl]pyrimidin-5-yl]oxyethanamine Chemical compound N1=CC(OCCN(C)C)=CN=C1C1=CC=CC(CN2C3=NC(=CN=C3N=N2)C2=CN(C)N=C2)=C1 KMUXNURNSDREAM-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 125000002632 imidazolidinyl group Chemical group 0.000 abstract 2
- 125000002757 morpholinyl group Chemical group 0.000 abstract 2
- 125000000160 oxazolidinyl group Chemical group 0.000 abstract 2
- 125000004193 piperazinyl group Chemical group 0.000 abstract 2
- 125000003386 piperidinyl group Chemical group 0.000 abstract 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 2
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- 125000000842 isoxazolyl group Chemical group 0.000 abstract 1
- 125000001715 oxadiazolyl group Chemical group 0.000 abstract 1
- 125000002971 oxazolyl group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000003226 pyrazolyl group Chemical group 0.000 abstract 1
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- 125000001544 thienyl group Chemical group 0.000 abstract 1
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- FBTUMDXHSRTGRV-ALTNURHMSA-N zorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(\C)=N\NC(=O)C=1C=CC=CC=1)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 FBTUMDXHSRTGRV-ALTNURHMSA-N 0.000 description 1
- 229960000641 zorubicin Drugs 0.000 description 1
- ZPFVQKPWGDRLHL-ZLYBXYBFSA-N zosuquidar trihydrochloride Chemical compound Cl.Cl.Cl.C([C@H](COC=1C2=CC=CN=C2C=CC=1)O)N(CC1)CCN1C1C2=CC=CC=C2[C@H]2C(F)(F)[C@H]2C2=CC=CC=C12 ZPFVQKPWGDRLHL-ZLYBXYBFSA-N 0.000 description 1
- 229930195724 β-lactose Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- 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
- A61P35/02—Antineoplastic agents specific for leukemia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102008037790A DE102008037790A1 (de) | 2008-08-14 | 2008-08-14 | Bicyclische Triazolderivate |
| DE102008037790 | 2008-08-14 | ||
| PCT/EP2009/005172 WO2010017870A1 (de) | 2008-08-14 | 2009-07-16 | Bicyclische triazolderivate zur behandlung von tumoren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2648233T3 true ES2648233T3 (es) | 2017-12-29 |
Family
ID=41138729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09777234.7T Active ES2648233T3 (es) | 2008-08-14 | 2009-07-16 | Derivados de triazol bicíclico para el tratamiento de tumores |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8435986B2 (https=) |
| EP (1) | EP2310013B1 (https=) |
| JP (1) | JP5475778B2 (https=) |
| KR (1) | KR20110051243A (https=) |
| CN (1) | CN102123710B (https=) |
| AR (1) | AR073055A1 (https=) |
| AU (1) | AU2009281491B2 (https=) |
| BR (1) | BRPI0914555A2 (https=) |
| CA (1) | CA2733941C (https=) |
| DE (1) | DE102008037790A1 (https=) |
| EA (1) | EA201100334A1 (https=) |
| ES (1) | ES2648233T3 (https=) |
| IL (1) | IL211193A0 (https=) |
| MX (1) | MX2011001511A (https=) |
| WO (1) | WO2010017870A1 (https=) |
| ZA (1) | ZA201101899B (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102014631A (zh) * | 2008-03-03 | 2011-04-13 | 泰格尔医药科技公司 | 酪氨酸激酶抑制剂 |
| EP3795573B1 (en) | 2009-12-31 | 2022-07-06 | Hutchison Medipharma Limited | Certain triazolopyrazines, compositions thereof and methods of use therefor |
| JP5960688B2 (ja) | 2010-05-17 | 2016-08-02 | インコゼン セラピューティクス プライベート リミテッド | プロテインキナーゼ調節物質としての新規３，５−二置換−３ｈ−［１，２，３］トリアゾロ［４，５−ｂ］ピリジン化合物 |
| PH12013500545A1 (en) * | 2010-09-23 | 2013-05-06 | Boehringer Ingelheim Int | Oxadiazole inhibitors of leukotriene production |
| DK3053923T3 (en) * | 2013-09-30 | 2018-07-23 | Korea Res Inst Chemical Tech | TRIAZOLOPYRAZINE DERIVATIVES AS TYROSIN KINASE INHIBITORS |
| EP3052107B1 (en) | 2013-10-04 | 2018-05-02 | Novartis AG | Organic compounds to treat hepatitis b virus |
| JP6694811B2 (ja) | 2013-10-04 | 2020-05-20 | ノバルティス アーゲー | ＲＮＡ干渉に使用するためのＲＮＡｉ剤用の３’末端キャップ |
| GB201321740D0 (en) * | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
| KR102379517B1 (ko) * | 2013-12-30 | 2022-03-25 | 제넨테크, 인크. | 세린/트레오닌 키나아제 억제제 |
| MA44007A (fr) | 2016-02-05 | 2018-12-19 | Denali Therapeutics Inc | Inhibiteurs du récepteur interagissant avec protéine kinase 1 |
| HRP20220636T1 (hr) | 2016-12-09 | 2022-07-22 | Denali Therapeutics Inc. | Spojevi korisni kao inhibitori ripk1 |
| KR20180092096A (ko) | 2017-02-08 | 2018-08-17 | 에이비온 주식회사 | 트리아졸로 피라진 유도체의 신규한 다형체 및 이의 제조 방법 |
| CN108570053A (zh) * | 2017-03-13 | 2018-09-25 | 中国科学院上海药物研究所 | 五元并六元杂环化合物、制备方法、中间体、组合和应用 |
| BR102018007822A2 (pt) | 2017-04-20 | 2018-11-06 | Gilead Sciences, Inc. | composto, métodos para inibir pd-1, pd-l1 e/ou interação de pd-1/pd-l1 e para tratamento de câncer, composição farmacêutica, e, kit para tratamento de ou prevenção de câncer ou uma doença ou condição |
| TWI707849B (zh) | 2018-02-13 | 2020-10-21 | 美商基利科學股份有限公司 | Pd‐1/pd‐l1抑制劑 |
| KR102591947B1 (ko) | 2018-04-19 | 2023-10-25 | 길리애드 사이언시즈, 인코포레이티드 | Pd-1/pd-l1 억제제 |
| EP3820572B1 (en) | 2018-07-13 | 2023-08-16 | Gilead Sciences, Inc. | Pd-1/pd-l1 inhibitors |
| US11236085B2 (en) | 2018-10-24 | 2022-02-01 | Gilead Sciences, Inc. | PD-1/PD-L1 inhibitors |
| IL314082A (en) | 2022-01-12 | 2024-09-01 | Denali Therapeutics Inc | Crystal forms of (S)-5-benzyl-N-(5-methyl-4-oxo-2,3,4,5-tetrahydropyrido[3,2-b][1,4]oxazapin-3-yl)- H4- 1,2,4-triazole-3-carboxamide |
Family Cites Families (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9624482D0 (en) | 1995-12-18 | 1997-01-15 | Zeneca Phaema S A | Chemical compounds |
| DE19604388A1 (de) | 1996-02-07 | 1997-08-14 | Merck Patent Gmbh | Arylalkyl-diazinone |
| BR9707495A (pt) | 1996-02-13 | 1999-07-27 | Zeneca Ltd | Derivado de quinazolina processo para a preparação do mesmo composição farmacêutica e processo para a produç o de um efeito antiangiogênico e/ou de redução de permeabilidade vascular em um animal de sangue quente |
| US6291455B1 (en) | 1996-03-05 | 2001-09-18 | Zeneca Limited | 4-anilinoquinazoline derivatives |
| GB9718972D0 (en) | 1996-09-25 | 1997-11-12 | Zeneca Ltd | Chemical compounds |
| JPH10259176A (ja) | 1997-03-17 | 1998-09-29 | Japan Tobacco Inc | 血管新生阻害作用を有する新規アミド誘導体及びその用途 |
| GB9714249D0 (en) | 1997-07-08 | 1997-09-10 | Angiogene Pharm Ltd | Vascular damaging agents |
| TWI241295B (en) * | 1998-03-02 | 2005-10-11 | Kowa Co | Pyridazine derivative and medicine containing the same as effect component |
| GB9900334D0 (en) | 1999-01-07 | 1999-02-24 | Angiogene Pharm Ltd | Tricylic vascular damaging agents |
| GB9900752D0 (en) | 1999-01-15 | 1999-03-03 | Angiogene Pharm Ltd | Benzimidazole vascular damaging agents |
| AUPQ462299A0 (en) | 1999-12-13 | 2000-01-13 | Fujisawa Pharmaceutical Co., Ltd. | Pyrazolopyridine compound and pharmaceutical use thereof |
| US6242461B1 (en) * | 2000-01-25 | 2001-06-05 | Pfizer Inc. | Use of aryl substituted azabenzimidazoles in the treatment of HIV and AIDS related diseases |
| NZ522074A (en) | 2000-05-31 | 2004-06-25 | Astrazeneca Ab | Indole derivatives with vascular damaging activity |
| IL153484A0 (en) | 2000-07-07 | 2003-07-06 | Angiogene Pharm Ltd | Colchinol derivatives as angiogenesis inhibitors |
| CN1255392C (zh) | 2000-07-07 | 2006-05-10 | 安吉奥金尼药品有限公司 | 作为血管生成抑制剂的秋水仙醇衍生物 |
| EP1463509A1 (en) | 2001-10-31 | 2004-10-06 | MERCK PATENT GmbH | Type 4 phosphodiesterase inhibitors and uses thereof |
| DE10228103A1 (de) | 2002-06-24 | 2004-01-15 | Bayer Cropscience Ag | Fungizide Wirkstoffkombinationen |
| CN1747949A (zh) * | 2002-12-20 | 2006-03-15 | 法马西亚公司 | 无环吡唑化合物 |
| US7563748B2 (en) | 2003-06-23 | 2009-07-21 | Cognis Ip Management Gmbh | Alcohol alkoxylate carriers for pesticide active ingredients |
| BRPI0412003A (pt) | 2003-07-02 | 2006-08-15 | Sugen Inc | arilmetil triazol e imidazopirazinas como inibidores de c-met |
| US7959919B2 (en) * | 2003-11-19 | 2011-06-14 | Novelmed Therapeutics, Inc. | Method of inhibiting factor B-mediated complement activation |
| RU2346996C2 (ru) | 2004-06-29 | 2009-02-20 | ЮРОПИЭН НИКЕЛЬ ПиЭлСи | Усовершенствованное выщелачивание основных металлов |
| US20070043057A1 (en) * | 2005-02-09 | 2007-02-22 | Threshold Pharmaceuticals, Inc. | Lonidamine analogs |
| WO2006015263A2 (en) * | 2004-07-29 | 2006-02-09 | Threshold Pharmaceuticals, Inc. | Lonidamine analogs |
| US20070015771A1 (en) * | 2004-07-29 | 2007-01-18 | Threshold Pharmaceuticals, Inc. | Lonidamine analogs |
| KR101280096B1 (ko) | 2005-06-29 | 2013-06-28 | 컴퓨메딕스 리미티드 | 전도성 브리지를 포함하는 센서 어셈블리 |
| KR20080080584A (ko) | 2005-11-30 | 2008-09-04 | 버텍스 파마슈티칼스 인코포레이티드 | ｃ-Ｍｅｔ의 억제제 및 이의 용도 |
| DE102005057924A1 (de) * | 2005-12-05 | 2007-06-06 | Merck Patent Gmbh | Pyridazinonderivate |
| HUE030390T2 (en) * | 2005-12-21 | 2017-05-29 | Janssen Pharmaceutica Nv | Triazolopyridazines as tyrosine kinase modulators |
| NL2000613C2 (nl) | 2006-05-11 | 2007-11-20 | Pfizer Prod Inc | Triazoolpyrazinederivaten. |
| JP2009538899A (ja) | 2006-05-30 | 2009-11-12 | ファイザー・プロダクツ・インク | トリアゾロピリダジン誘導体 |
| TW200801513A (en) | 2006-06-29 | 2008-01-01 | Fermiscan Australia Pty Ltd | Improved process |
| PE20080403A1 (es) | 2006-07-14 | 2008-04-25 | Amgen Inc | Derivados heterociclicos fusionados y metodos de uso |
| WO2008033455A2 (en) * | 2006-09-13 | 2008-03-20 | The Institutes For Pharmaceutical Discovery, Llc | Biphenyl and heteroaryl phenyl derivatives as protein tyrosine phosphatases inhibitors |
| CA2667453A1 (en) | 2006-10-23 | 2008-05-02 | Sgx Pharmaceuticals, Inc. | Triazolo-pyridazine protein kinase modulators |
| DE102007026341A1 (de) * | 2007-06-06 | 2008-12-11 | Merck Patent Gmbh | Benzoxazolonderivate |
| DE102007032507A1 (de) * | 2007-07-12 | 2009-04-02 | Merck Patent Gmbh | Pyridazinonderivate |
| RU2010121763A (ru) * | 2007-10-31 | 2011-12-10 | Ниссан Кемикал Индастриз, Лтд. (Jp) | Производные пиридазинона и ингибиторы р2х7 рецептора |
| DE102007061963A1 (de) * | 2007-12-21 | 2009-06-25 | Merck Patent Gmbh | Pyridazinonderivate |
| CN101538245B (zh) * | 2008-03-18 | 2011-02-16 | 中国科学院上海药物研究所 | 一类哒嗪酮类化合物及其制备方法和制备药物的用途 |
| DE102008019907A1 (de) * | 2008-04-21 | 2009-10-22 | Merck Patent Gmbh | Pyridazinonderivate |
| WO2009142732A2 (en) * | 2008-05-20 | 2009-11-26 | Cephalon, Inc. | Substituted pyridazinone derivatives as histamine-3 (h3) receptor ligands |
| DE102008028905A1 (de) * | 2008-06-18 | 2009-12-24 | Merck Patent Gmbh | 3-(3-Pyrimidin-2-yl-benzyl)-[1,2,4]triazolo[4,3-b]pyridazinderivate |
| CN102105454A (zh) * | 2008-07-25 | 2011-06-22 | 贝林格尔.英格海姆国际有限公司 | 合成1型11β-羟基类固醇脱氢酶的抑制剂 |
| WO2010113986A1 (ja) * | 2009-03-30 | 2010-10-07 | 住友化学株式会社 | ピリダジノン化合物の有害節足動物防除用途 |
| AR082590A1 (es) * | 2010-08-12 | 2012-12-19 | Hoffmann La Roche | Inhibidores de la tirosina-quinasa de bruton |
-
2008
- 2008-08-14 DE DE102008037790A patent/DE102008037790A1/de not_active Withdrawn
-
2009
- 2009-07-16 CN CN2009801314380A patent/CN102123710B/zh not_active Expired - Fee Related
- 2009-07-16 EA EA201100334A patent/EA201100334A1/ru unknown
- 2009-07-16 MX MX2011001511A patent/MX2011001511A/es not_active Application Discontinuation
- 2009-07-16 WO PCT/EP2009/005172 patent/WO2010017870A1/de not_active Ceased
- 2009-07-16 EP EP09777234.7A patent/EP2310013B1/de active Active
- 2009-07-16 AU AU2009281491A patent/AU2009281491B2/en not_active Ceased
- 2009-07-16 US US13/059,016 patent/US8435986B2/en not_active Expired - Fee Related
- 2009-07-16 JP JP2011522392A patent/JP5475778B2/ja not_active Expired - Fee Related
- 2009-07-16 KR KR1020117005525A patent/KR20110051243A/ko not_active Withdrawn
- 2009-07-16 CA CA2733941A patent/CA2733941C/en active Active
- 2009-07-16 ES ES09777234.7T patent/ES2648233T3/es active Active
- 2009-07-16 BR BRPI0914555A patent/BRPI0914555A2/pt not_active IP Right Cessation
- 2009-08-14 AR ARP090103142A patent/AR073055A1/es unknown
-
2011
- 2011-02-10 IL IL211193A patent/IL211193A0/en active IP Right Grant
- 2011-03-11 ZA ZA2011/01899A patent/ZA201101899B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2009281491A1 (en) | 2010-02-18 |
| KR20110051243A (ko) | 2011-05-17 |
| DE102008037790A1 (de) | 2010-02-18 |
| MX2011001511A (es) | 2011-03-15 |
| JP2011530545A (ja) | 2011-12-22 |
| HK1159989A1 (en) | 2012-08-10 |
| US20110135600A1 (en) | 2011-06-09 |
| EP2310013B1 (de) | 2017-08-23 |
| AR073055A1 (es) | 2010-10-13 |
| ZA201101899B (en) | 2011-11-30 |
| IL211193A0 (en) | 2011-04-28 |
| AU2009281491B2 (en) | 2014-02-20 |
| BRPI0914555A2 (pt) | 2015-12-15 |
| CN102123710B (zh) | 2012-11-07 |
| CN102123710A (zh) | 2011-07-13 |
| CA2733941C (en) | 2016-10-04 |
| EP2310013A1 (de) | 2011-04-20 |
| WO2010017870A1 (de) | 2010-02-18 |
| US8435986B2 (en) | 2013-05-07 |
| JP5475778B2 (ja) | 2014-04-16 |
| EA201100334A1 (ru) | 2011-08-30 |
| CA2733941A1 (en) | 2010-02-18 |
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