HRP20120202T1 - AMIDOFENOKSIINDAZOLI, KORISNI KAO INHIBITORI c-MET - Google Patents
AMIDOFENOKSIINDAZOLI, KORISNI KAO INHIBITORI c-MET Download PDFInfo
- Publication number
- HRP20120202T1 HRP20120202T1 HR20120202T HRP20120202T HRP20120202T1 HR P20120202 T1 HRP20120202 T1 HR P20120202T1 HR 20120202 T HR20120202 T HR 20120202T HR P20120202 T HRP20120202 T HR P20120202T HR P20120202 T1 HRP20120202 T1 HR P20120202T1
- Authority
- HR
- Croatia
- Prior art keywords
- pharmaceutically acceptable
- acceptable salt
- methyl
- compound according
- cancer
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title 1
- -1 2-methoxypyrimidin-5-yl Chemical group 0.000 claims abstract 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 17
- 150000001875 compounds Chemical class 0.000 claims abstract 16
- 150000003839 salts Chemical class 0.000 claims abstract 15
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 4
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 201000009030 Carcinoma Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000011654 childhood malignant neoplasm Diseases 0.000 claims 1
- YKGMKSIHIVVYKY-UHFFFAOYSA-N dabrafenib mesylate Chemical group CS(O)(=O)=O.S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 YKGMKSIHIVVYKY-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 1
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 208000026037 malignant tumor of neck Diseases 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- QHADVLVFMKEIIP-UHFFFAOYSA-N n-[3-fluoro-4-[1-methyl-6-(1h-pyrazol-4-yl)indazol-5-yl]oxyphenyl]-1-(4-fluorophenyl)-6-methyl-2-oxopyridine-3-carboxamide Chemical compound O=C1N(C=2C=CC(F)=CC=2)C(C)=CC=C1C(=O)NC(C=C1F)=CC=C1OC1=CC=2C=NN(C)C=2C=C1C=1C=NNC=1 QHADVLVFMKEIIP-UHFFFAOYSA-N 0.000 claims 1
- XCPSZMLNENDLKG-UHFFFAOYSA-N n-[3-fluoro-4-[1-methyl-6-(1h-pyrazol-4-yl)indazol-5-yl]oxyphenyl]-6-methyl-2-oxo-1-phenylpyridine-3-carboxamide Chemical compound O=C1N(C=2C=CC=CC=2)C(C)=CC=C1C(=O)NC(C=C1F)=CC=C1OC1=CC=2C=NN(C)C=2C=C1C=1C=NNC=1 XCPSZMLNENDLKG-UHFFFAOYSA-N 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 239000002245 particle Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- IWUCHFKAVLZIBD-UHFFFAOYSA-N NCN(C)F Chemical compound NCN(C)F IWUCHFKAVLZIBD-UHFFFAOYSA-N 0.000 abstract 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D403/12—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 chain containing hetero atoms as chain links
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Spoj formule: naznačen time što: R1 je H ili metil; R2 je amino, dimetilamino, fluor, ciklopropilni, piridilni, izborno supstituiran s amino supstituentom ili 1-2 metilna supstituenta, pirazolilni, izborno supstituiran s dva metilna supstituenta, 2-metoksipirimidin-5-ilni, 4-metilsulfonilfenilni, tetrahidro-2H-piran-4-ilamino, (tetrahidro-2H-piran-4-il)aminokarbonilni ili morfolin-4-ilni supstituent: gdje se Ra, Rb i Rc neovisno bira između H ili metila; R3 je H ili F; R4 je H, metil, piperidin-1-ilmetil, morfolin-4-ilmetil ili pirazol-1-ilmetil; R5 je H ili F; iX je CH=N, CH=CH, CH=C(CH3), C(CH3)=CH, C(CH3)=N, N(CH3) ili C(morfolin-4-ilmetil)=CH; ili njegova farmaceutski prihvatljiva sol.Patent sadrži još 14 patentnih zahtjeva.
Claims (15)
1. Spoj formule:
[image]
naznačen time što:
R1 je H ili metil;
R2 je amino, dimetilamino, fluor, ciklopropilni, piridilni, izborno supstituiran s amino supstituentom ili 1-2 metilna supstituenta, pirazolilni, izborno supstituiran s dva metilna supstituenta, 2-metoksipirimidin-5-ilni, 4-metilsulfonilfenilni, tetrahidro-2H-piran-4-ilamino, (tetrahidro-2H-piran-4-il)aminokarbonilni ili morfolin-4-ilni supstituent:
[image]
gdje se Ra, Rb i Rc neovisno bira između H ili metila;
R3 je H ili F;
R4 je H, metil, piperidin-1-ilmetil, morfolin-4-ilmetil ili pirazol-1-ilmetil;
R5 je H ili F; i
X je CH=N, CH=CH, CH=C(CH3), C(CH3)=CH, C(CH3)=N, N(CH3) ili C(morfolin-4-ilmetil)=CH;
ili njegova farmaceutski prihvatljiva sol.
2. Spoj u skladu s patentnim zahtjevom 1, ili njegova farmaceutski prihvatljiva sol, naznačen time što R2 je amino, dimetilamino, ciklopropil, piridil, izborno supstituiran s amino supstituentom ili 1-2 metilna supstituenta, pirazol-4-il ili morfolin-4-il.
3. Spoj u skladu s patentnim zahtjevom 1, ili njegova farmaceutski prihvatljiva sol, naznačen time što R2 je amino, dimetilamino, pirazol-4-il ili morfolin-4-il.
4. Spoj u skladu s patentnim zahtjevom 1, ili njegova farmaceutski prihvatljiva sol, naznačen time što R2 je pirazol-4-il.
5. Spoj u skladu s patentnim zahtjevima 1-4, ili njegova farmaceutski prihvatljiva sol, naznačen time što R4 je H, metil ili morfolin-4-ilmetil.
6. Spoj u skladu s patentnim zahtjevima 1-4, ili njegova farmaceutski prihvatljiva sol, naznačen time što R4 je H.
7. Spoj u skladu s patentnim zahtjevima 1-6, ili njegova farmaceutski prihvatljiva sol, naznačen time što X je CH=CH ili CH=C(CH3).
8. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je N-(3-fluor-4-(1-metil-6-(1H-pirazol-4-il)-1H-indazol-5-iloksi)fenil)-1-(4-fluorfenil)-6-metil-2-okso-1,2-dihidropiridin-3-karboksamid, ili njegova farmaceutski prihvatljiva sol.
9. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je N-(3-fluor-4-(1-metil-6-(1H-pirazol-4-il)-1H-indazol-5-iloksi)fenil)-6-metil-2-okso-1-fenil-1,2-dihidropiridin-3-karboksamid, ili njegova farmaceutski prihvatljiva sol.
10. Spoj u skladu s patentnim zahtjevima 1-9, naznačen time što farmaceutski prihvatljiva sol je metansulfonatna sol.
11. Spoj u skladu s patentnim zahtjevima 1-10, naznačen time što veličina čestica je manja od 10 µm.
12. Farmaceutski pripravak, naznačen time što sadrži spoj u skladu s patentnim zahtjevima 1-11, ili njegovu farmaceutski prihvatljivu sol, i farmaceutski prihvatljivu podlogu, razrjeđivač ili pomoćnu tvar.
13. Spoj u skladu s bilo kojim od patentnih zahtjeva 1-11, ili njegova farmaceutski prihvatljiva sol, naznačen time što je namijenjen upotrebi kao medikament.
14. Spoj, ili njegova farmaceutski prihvatljiva sol, u skladu s bilo kojim od patentnih zahtjeva 1-11, naznačen time što je namijenjen upotrebi u liječenju raka.
15. Spoj, ili njegova farmaceutski prihvatljiva sol, namijenjen upotrebi u skladu s patentnim zahtjevom 14, naznačen time što rak se bira iz skupine koju čine rak pluća, rak dojke, kolorektalni rak, rak bubrega, rak gušterače, rak glave, rak vrata, nasljedni karcinom papilarnih stanica bubrega, hepatocelularni karcinom u dječjoj dobi, te rak želuca.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8329408P | 2008-07-24 | 2008-07-24 | |
| US8508208P | 2008-07-31 | 2008-07-31 | |
| US10865908P | 2008-10-27 | 2008-10-27 | |
| PCT/US2009/050640 WO2010011538A1 (en) | 2008-07-24 | 2009-07-15 | Amidophenoxyindazoles useful as inhibitors of c-met |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20120202T1 true HRP20120202T1 (hr) | 2012-03-31 |
Family
ID=41010247
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20120202T HRP20120202T1 (hr) | 2008-07-24 | 2012-03-01 | AMIDOFENOKSIINDAZOLI, KORISNI KAO INHIBITORI c-MET |
Country Status (36)
| Country | Link |
|---|---|
| US (2) | US8030302B2 (hr) |
| EP (1) | EP2310382B1 (hr) |
| JP (1) | JP5414794B2 (hr) |
| KR (1) | KR101334456B1 (hr) |
| CN (1) | CN102105462B (hr) |
| AR (1) | AR074632A1 (hr) |
| AT (1) | ATE546444T1 (hr) |
| AU (1) | AU2009274256B2 (hr) |
| BR (1) | BRPI0916286B8 (hr) |
| CA (1) | CA2731773C (hr) |
| CL (1) | CL2011000134A1 (hr) |
| CO (1) | CO6351737A2 (hr) |
| CR (1) | CR20110046A (hr) |
| CY (1) | CY1112595T1 (hr) |
| DK (1) | DK2310382T3 (hr) |
| DO (1) | DOP2011000009A (hr) |
| EA (1) | EA018385B1 (hr) |
| EC (1) | ECSP11010778A (hr) |
| ES (1) | ES2379587T3 (hr) |
| HK (1) | HK1155172A1 (hr) |
| HR (1) | HRP20120202T1 (hr) |
| IL (1) | IL210490A (hr) |
| JO (1) | JO2788B1 (hr) |
| MA (1) | MA32594B1 (hr) |
| MX (1) | MX2011000925A (hr) |
| MY (1) | MY163852A (hr) |
| NZ (1) | NZ590013A (hr) |
| PE (1) | PE20110150A1 (hr) |
| PL (1) | PL2310382T3 (hr) |
| PT (1) | PT2310382E (hr) |
| RS (1) | RS52261B (hr) |
| SI (1) | SI2310382T1 (hr) |
| SV (1) | SV2011003816A (hr) |
| TW (1) | TWI365185B (hr) |
| WO (1) | WO2010011538A1 (hr) |
| ZA (1) | ZA201100219B (hr) |
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|---|---|---|---|---|
| AU2009303602B2 (en) | 2008-10-14 | 2012-06-14 | Sunshine Lake Pharma Co., Ltd. | Compounds and methods of use |
| KR20110133048A (ko) | 2009-03-21 | 2011-12-09 | 닝 시 | 아미노 에스테르 유도체, 그의 염 및 이용 방법 |
| EP2680886B1 (en) | 2011-02-28 | 2016-08-10 | Calitor Sciences, LLC | Substituted quinoline compounds |
| US8962623B2 (en) * | 2011-03-04 | 2015-02-24 | Locus Pharmaceuticals, Inc. | Aminopyrazine compounds |
| KR20130118612A (ko) * | 2012-04-20 | 2013-10-30 | (주)네오믹스 | 신규한 아미노피리딘 유도체 및 이의 용도 |
| US9260531B2 (en) * | 2012-05-09 | 2016-02-16 | Eli Lilly And Company | Anti-c-met antibodies |
| WO2014134313A1 (en) * | 2013-02-27 | 2014-09-04 | Array Biopharma Inc. | Intermediates for use in the preparation of indazole derivatives and processes for the preparation thereof |
| CN104140393B (zh) * | 2013-12-10 | 2016-09-21 | 郑州泰基鸿诺医药股份有限公司 | 一种芳环/芳杂环叔丁醇酯类化合物的制备方法 |
| JP6500037B2 (ja) | 2014-04-22 | 2019-04-10 | キャリター・サイエンシーズ・リミテッド・ライアビリティ・カンパニーＣａｌｉｔｏｒ Ｓｃｉｅｎｃｅｓ， Ｌｌｃ | 二環式ピラゾロン化合物および使用方法 |
| TW201716085A (zh) * | 2015-08-12 | 2017-05-16 | 應克隆公司 | 癌症之組合療法 |
| EP3442573A1 (en) | 2016-04-15 | 2019-02-20 | Eli Lilly and Company | Combination of ramucirumab and merestinib for use in treatment of colorectal cancer |
| BR112018074748A2 (pt) | 2016-06-02 | 2019-03-06 | Immunocore Limited | composição terapêutica biespecífica de redirecionamento de células t, e método de tratamento de câncer gp100 positivo em um paciente |
| EP3490676A1 (en) * | 2016-07-29 | 2019-06-05 | Eli Lilly and Company | Combination therapy with merestinib and anti-pd-l1 or anti-pd-1 inhibitors for use in the treatment of cancer |
| CN108069938A (zh) * | 2016-11-15 | 2018-05-25 | 中国药科大学 | 2,4-二取代吡啶类化合物及其制备方法和应用 |
| CN109982700A (zh) * | 2016-11-16 | 2019-07-05 | 伊莱利利公司 | 具有外显子14跳跃突变或外显子14跳跃表型的癌症的治疗 |
| CN109963562A (zh) | 2016-11-16 | 2019-07-02 | 伊莱利利公司 | 用于具有外显子14跳读突变或外显子14跳读表型的癌症的组合疗法 |
| CN107382968A (zh) * | 2017-07-06 | 2017-11-24 | 北京万全德众医药生物技术有限公司 | 一种吲哚类c‑Met抑制剂的制备方法 |
| CN107311983A (zh) * | 2017-07-06 | 2017-11-03 | 北京万全德众医药生物技术有限公司 | 吲哚类小分子c‑met抑制剂 |
| US10180422B1 (en) | 2017-08-22 | 2019-01-15 | Scripps Health | Methods of treating a neuroendocrine tumor |
| EP3480201A1 (en) | 2017-11-06 | 2019-05-08 | Oncostellae, S.L. | New analogs as androgen receptor and glucocorticoid receptor modulators |
| JP7377798B2 (ja) | 2017-11-24 | 2023-11-10 | 南京明徳新薬研発有限公司 | ｃ－ＭＥＴ／ＡＸＬ阻害剤としてのウラシル系化合物 |
| WO2019141202A1 (zh) * | 2018-01-17 | 2019-07-25 | 南京药捷安康生物科技有限公司 | Tam家族激酶/和csf1r激酶抑制剂及其用途 |
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| US5747577A (en) * | 1995-12-27 | 1998-05-05 | Xerox Corporation | Conductive particles containing carbon black and processes for the preparation thereof |
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