HRP20110550T1 - Derivati 7-alkinil-1,8-naftiridinona, njihovo dobivanje i njihova upotreba u terapiji - Google Patents
Derivati 7-alkinil-1,8-naftiridinona, njihovo dobivanje i njihova upotreba u terapiji Download PDFInfo
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- HRP20110550T1 HRP20110550T1 HR20110550T HRP20110550T HRP20110550T1 HR P20110550 T1 HRP20110550 T1 HR P20110550T1 HR 20110550 T HR20110550 T HR 20110550T HR P20110550 T HRP20110550 T HR P20110550T HR P20110550 T1 HRP20110550 T1 HR P20110550T1
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- 239000003814 drug Substances 0.000 title claims 8
- 238000002360 preparation method Methods 0.000 title claims 8
- 150000001875 compounds Chemical class 0.000 claims abstract 29
- 239000000203 mixture Substances 0.000 claims abstract 7
- 150000003839 salts Chemical class 0.000 claims abstract 7
- 239000002253 acid Substances 0.000 claims abstract 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 5
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims abstract 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 229940079593 drug Drugs 0.000 claims 7
- 206010028980 Neoplasm Diseases 0.000 claims 5
- 230000002265 prevention Effects 0.000 claims 5
- 102000016663 Vascular Endothelial Growth Factor Receptor-3 Human genes 0.000 claims 3
- 108010053100 Vascular Endothelial Growth Factor Receptor-3 Proteins 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 230000033115 angiogenesis Effects 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 230000035168 lymphangiogenesis Effects 0.000 claims 2
- GGUGSPQHCDIQJH-UHFFFAOYSA-N 2-amino-1-ethyl-7-(3-methoxyprop-1-ynyl)-n-methyl-4-oxo-1,8-naphthyridine-3-carboxamide Chemical compound C1=C(C#CCOC)N=C2N(CC)C(N)=C(C(=O)NC)C(=O)C2=C1 GGUGSPQHCDIQJH-UHFFFAOYSA-N 0.000 claims 1
- OZBUUUZXZXKCJL-UHFFFAOYSA-N 2-amino-7-(3,4-dimethoxy-3-methylbut-1-ynyl)-1-ethyl-n-methyl-4-oxo-1,8-naphthyridine-3-carboxamide Chemical compound C1=C(C#CC(C)(COC)OC)N=C2N(CC)C(N)=C(C(=O)NC)C(=O)C2=C1 OZBUUUZXZXKCJL-UHFFFAOYSA-N 0.000 claims 1
- IRJLUJDWHXZXMO-UHFFFAOYSA-N 2-amino-7-(3-amino-3-methylbut-1-ynyl)-1-ethyl-n-methyl-4-oxo-1,8-naphthyridine-3-carboxamide;hydrochloride Chemical compound Cl.C1=C(C#CC(C)(C)N)N=C2N(CC)C(N)=C(C(=O)NC)C(=O)C2=C1 IRJLUJDWHXZXMO-UHFFFAOYSA-N 0.000 claims 1
- AFYLSMVZLRKGFB-UHFFFAOYSA-N 2-amino-7-[3-(2-amino-2-oxoethoxy)-3-methylbut-1-ynyl]-1-ethyl-n-methyl-4-oxo-1,8-naphthyridine-3-carboxamide Chemical compound C1=C(C#CC(C)(C)OCC(N)=O)N=C2N(CC)C(N)=C(C(=O)NC)C(=O)C2=C1 AFYLSMVZLRKGFB-UHFFFAOYSA-N 0.000 claims 1
- 201000003076 Angiosarcoma Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
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- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
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- 208000001258 Hemangiosarcoma Diseases 0.000 claims 1
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- 206010027476 Metastases Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
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- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 208000034038 Pathologic Neovascularization Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 208000035977 Rare disease Diseases 0.000 claims 1
- 208000034541 Rare lymphatic malformation Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 230000001548 androgenic effect Effects 0.000 claims 1
- 239000004037 angiogenesis inhibitor Substances 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 230000000340 anti-metabolite Effects 0.000 claims 1
- 229940044684 anti-microtubule agent Drugs 0.000 claims 1
- 230000001028 anti-proliverative effect Effects 0.000 claims 1
- 229940088710 antibiotic agent Drugs 0.000 claims 1
- 229940100197 antimetabolite Drugs 0.000 claims 1
- 239000002256 antimetabolite Substances 0.000 claims 1
- 239000003080 antimitotic agent Substances 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 210000000038 chest Anatomy 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 208000019425 cirrhosis of liver Diseases 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- 208000033679 diabetic kidney disease Diseases 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 230000001076 estrogenic effect Effects 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 201000010536 head and neck cancer Diseases 0.000 claims 1
- 208000014829 head and neck neoplasm Diseases 0.000 claims 1
- 201000011066 hemangioma Diseases 0.000 claims 1
- 239000005556 hormone Substances 0.000 claims 1
- 229940088597 hormone Drugs 0.000 claims 1
- 239000002955 immunomodulating agent Substances 0.000 claims 1
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- 230000004054 inflammatory process Effects 0.000 claims 1
- 230000002687 intercalation Effects 0.000 claims 1
- 238000009830 intercalation Methods 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 229940043355 kinase inhibitor Drugs 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm 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
- 229940126601 medicinal product Drugs 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- VKBNTNMCHPHTHP-UHFFFAOYSA-N methyl n-[3-[7-amino-8-ethyl-6-(methylcarbamoyl)-5-oxo-1,8-naphthyridin-2-yl]prop-2-ynyl]carbamate Chemical compound C1=C(C#CCNC(=O)OC)N=C2N(CC)C(N)=C(C(=O)NC)C(=O)C2=C1 VKBNTNMCHPHTHP-UHFFFAOYSA-N 0.000 claims 1
- 244000005700 microbiome Species 0.000 claims 1
- 201000009925 nephrosclerosis Diseases 0.000 claims 1
- 230000000771 oncological effect Effects 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 210000002345 respiratory system Anatomy 0.000 claims 1
- 208000037803 restenosis Diseases 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 230000001732 thrombotic effect Effects 0.000 claims 1
- 239000004066 vascular targeting agent Substances 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- 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
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Abstract
Spoj formule (I): naznačen time što: R1 i R2, međusobno neovisno, predstavljaju:• atom vodika, • C1-C7 alkilnu skupinu, izborno supstituiranu s jednom ili više alkoksi skupina, R3 predstavlja C1-C7 alkilnu skupinu, R4 predstavlja atom vodika ili C1-C4 alkilnu skupinu, Y predstavlja C1-C4 alkoksi skupinu ili skupinu -NRR' ili -O(CH2)n-C(O)-NRR', gdje su R i R' kao što je definirano niže, a n je cijeli broj, koji je 1 ili 2, R'' predstavlja C1-C4 alkilnu skupinu, iR i R', međusobno neovisno, predstavljaju atom vodika, -CO-(C1-C4 alkil) skupinu ili skupinu -COOR'', gdje R'' je kao što je definirano gore, u obliku baze ili adicijske soli s kiselinom, te enantiomera ili dijastereoizomera, uključujući njihovu smjesu. Patent sadrži još 15 patentnih zahtjeva.
Claims (16)
1. Spoj formule (I):
[image]
naznačen time što:
R1 i R2, međusobno neovisno, predstavljaju:
• atom vodika,
• C1-C7 alkilnu skupinu, izborno supstituiranu s jednom ili više alkoksi skupina,
R3 predstavlja C1-C7 alkilnu skupinu,
R4 predstavlja atom vodika ili C1-C4 alkilnu skupinu,
Y predstavlja C1-C4 alkoksi skupinu ili skupinu -NRR' ili -O(CH2)n-C(O)-NRR', gdje su R i R' kao što je definirano niže, a n je cijeli broj, koji je 1 ili 2,
R'' predstavlja C1-C4 alkilnu skupinu, i
R i R', međusobno neovisno, predstavljaju atom vodika, -CO-(C1-C4 alkil) skupinu ili skupinu -COOR'', gdje R'' je kao što je definirano gore,
u obliku baze ili adicijske soli s kiselinom, te enantiomera ili dijastereoizomera, uključujući njihovu smjesu.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time što Y predstavlja C1-C4-alkoksi skupinu,
u obliku baze ili adicijske soli s kiselinom, te enantiomera ili dijastereoizomera, uključujući njihovu smjesu.
3. Spoj u skladu s patentnim zahtjevom 1, naznačen time što Y predstavlja skupinu -NRR', gdje su R i R' kao u patentnom zahtjevu 1, u obliku baze ili adicijske soli s kiselinom, te enantiomera ili dijastereoizomera, uključujući njihovu smjesu.
4. Spoj u skladu s patentnim zahtjevom 1, naznačen time što Y predstavlja skupinu -O(CH2)n-C(O)-NRR', gdje su R i R' kao u patentnom zahtjevu 1, a n je cijeli broj, koji je 1 ili 2, u obliku baze ili adicijske soli s kiselinom, te enantiomera ili dijastereoizomera, uključujući njihovu smjesu.
5. Spoj u skladu s patentnim zahtjevom 1, naznačen time što ga se bira između:
■ metil-{3-[7-amino-8-etil-6-(metilkarbamoil)-5-okso-5,8-dihidro-1,8-naftiridin-2-il]prop-2-in-1-il}karbamata
■ 2-amino-7-(3-amino-3-metilbut-1-in-1-il)-1-etil-N-metil-4-okso-1,4-dihidro-1,8-naftiridin-3-karboksamid-hidroklorida
■ (±)-2-amino-7-(3,4-dimetoksi-3-metilbut-1-in-1-il)-1-etil-N-metil-4-okso-1,4-dihidro-1,8-naftiridin-3-karboksamida
■ 2-amino-7-[3-(2-amino-2-oksoetoksi)-3-metilbut-1-in-1-il]-1-etil-N-metil-4-okso-1,4-dihidro-1,8-naftiridin-3-karboksamida i
■ 2-amino-1-etil-7-(3-metoksiprop-1-in-1-il)-N-metil-4-okso-1,4-dihidro-1,8-naftiridin-3-karboksamida.
6. Postupak dobivanja spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 5, naznačen time što se sastoji u reakciji spoja formule (VII)
[image]
gdje X je atom halogena, a R3 i R4 su kao što je definirano u bilo kojem od prethodnih patentnih zahtjeva,
sa spojem formule (VIII)
[image]
gdje Y, R1 i R2 su kao što je definirano u bilo kojem od prethodnih patentnih zahtjeva.
7. Medikament, naznačen time što sadrži spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 5, ili adicijsku sol tog spoja s farmaceutski prihvatljivom kiselinom, ili enantiomer, dijastereoizomer, ili njihovu smjesu, spoja formule (I).
8. Farmaceutski pripravak, naznačen time što sadrži spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 5, ili farmaceutski prihvatljivu sol, ili enantiomer, dijastereoizomer, ili njihovu smjesu, tog spoja, a također i najmanje jednu farmaceutski prihvatljivu pomoćnu tvar.
9. Kombinacija najmanje jednog spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 5 s najmanje jednim kemoterapijskim sredstvom, naznačena time što se navedeno sredstvo bira između:
• alkilacijskih sredstava,
• interkalacijskih sredstava,
• antimikrotubulskih sredstava,
• antimitotskih sredstava,
• antimetabolita,
• antiproliferativna sredstva,
• antibiotika,
• imunomodulacijskih sredstava,
• protuupalnih sredstava,
• inhibitora kinaza,
• antiangiogenih sredstava,
• antivaskularnih sredstava,
• estrogenih i androgenih hormona.
10. Upotreba spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 5, naznačena time što je navedeni spoj namijenen pripravi medikamenta namijenjenog liječenju bilo koje bolesti kod koje je uključen VEGFR-3.
11. Upotreba spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 5, naznačena time što je navedeni spoj namijenen pripravi medikamenta za liječenje i/ili sprječavanje raka i njegovih metastaza.
12. Upotreba spoja formule (I) u skladu s patentnim zahtjevom 11, naznačena time što je navedeni spoj namijenen pripravi medikamenta za liječenje i/ili sprječavanje glioblastoma, multiplih mijeloma, mijelodisplazičnih sindroma, Kaposijevih sarkoma, kožnih angiosarkoma, čvrstih tumora, limfoma, melanoma, raka dojke, kolorektalnog raka, raka pluća, uključujući rak velikih stanica, raka gušterače, raka prostate, raka bubrega, raka glave i vrata, raka jetre, raka jajnika, raka dišnog sustava i prsnog koša, drugih tumora koji eksprimiraju VEGFR-3 ili uključuju proces angiogeneze ili limfangiogeneze.
13. Upotreba spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 5, naznačena time što je navedeni spoj namijenen pripravi medikamenta za liječenje i/ili sprječavanje neonkoloških proliferativnih bolesti i patološke angiogeneze povezane s VEGFR-3.
14. Upotreba spoja formule (I) u skladu s patentnim zahtjevom 13, naznačena time što je navedeni spoj namijenen pripravi medikamenta za liječenje i/ili sprječavanje bolesti, poput: artroza, restenoza, psorijaze, hemangioma, limfangioma, glaukoma, glomerulonefritisa, dijabetičnih nefropatija, nefroskleroze, trombotičkih mikroangiopatskih sindroma, ciroze jetre, ateroskleroze, odbacivanja presađenog organa, ili bolesti oka koje uključuju proces angiogeneze ili limfangiogeneze.
15. Upotreba spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 5, naznačena time što je navedeni spoj namijenen pripravi medikamenta za liječenje i/ili sprječavanje kronične ili nekronične upale, infekcije mikroorganizmima i autoimunih bolesti, poput reumatoidnog artritisa.
16. Upotreba spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 5, naznačena time što je navedeni spoj namijenen pripravi medikamenta za liječenje i/ili sprječavanje rijetkih bolesti, poput limfangiolejomiomatoze.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
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| FR0704193A FR2917413B1 (fr) | 2007-06-13 | 2007-06-13 | Derives de 7-alkynyl-1,8-naphthyridones, leur preparation et leur application en therapeutique |
| PCT/FR2008/000794 WO2009007536A2 (fr) | 2007-06-13 | 2008-06-11 | Dérivés de 7 -alkynyl-1,8-naphthyridones, leur préparation et leur application en thérapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110550T1 true HRP20110550T1 (hr) | 2011-09-30 |
Family
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Family Applications (1)
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| HR20110550T HRP20110550T1 (hr) | 2007-06-13 | 2011-07-25 | Derivati 7-alkinil-1,8-naftiridinona, njihovo dobivanje i njihova upotreba u terapiji |
Country Status (29)
| Country | Link |
|---|---|
| US (2) | US8263614B2 (hr) |
| EP (1) | EP2158194B1 (hr) |
| JP (1) | JP5346337B2 (hr) |
| KR (1) | KR20100019507A (hr) |
| CN (1) | CN101815715B (hr) |
| AR (1) | AR066955A1 (hr) |
| AT (1) | ATE509923T1 (hr) |
| AU (1) | AU2008274100B2 (hr) |
| BR (1) | BRPI0813809B1 (hr) |
| CA (1) | CA2690349C (hr) |
| CO (1) | CO6150157A2 (hr) |
| CY (1) | CY1111748T1 (hr) |
| DK (1) | DK2158194T3 (hr) |
| EA (1) | EA016552B1 (hr) |
| ES (1) | ES2366629T3 (hr) |
| FR (1) | FR2917413B1 (hr) |
| HK (1) | HK1143590A1 (hr) |
| HR (1) | HRP20110550T1 (hr) |
| IL (1) | IL202677A (hr) |
| IN (1) | IN2009KN04279A (hr) |
| MA (1) | MA31674B1 (hr) |
| ME (1) | ME00957B (hr) |
| MX (1) | MX2009013514A (hr) |
| MY (1) | MY146939A (hr) |
| NZ (1) | NZ581883A (hr) |
| PL (1) | PL2158194T3 (hr) |
| PT (1) | PT2158194E (hr) |
| SI (1) | SI2158194T1 (hr) |
| WO (1) | WO2009007536A2 (hr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2917412B1 (fr) * | 2007-06-13 | 2009-08-21 | Sanofi Aventis Sa | Derives de 7-alkynyl, 1,8-naphthyridones, leur preparation et leur application en therapeutique |
| CA2708264C (en) | 2007-12-10 | 2018-07-03 | Sunesis Pharmaceuticals, Inc. | Methods of using (+)-1,4-dihydro-7-[(3s,4s)-3-methoxy-4-(methylamino)-1-pyrrolidinyl]-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid for treatment of antecedent hematologic disorders |
| FR2933700B1 (fr) | 2008-07-08 | 2010-07-30 | Sanofi Aventis | Derives de pyridino-pyridinones, leur preparation et leur application en therapeutique |
| FR2952934B1 (fr) | 2009-11-23 | 2012-06-22 | Sanofi Aventis | Derives de pyridino-pyridinones, leur preparation et leur application en therapeutique |
| FR2954943B1 (fr) * | 2010-01-07 | 2013-03-01 | Sanofi Aventis | Derives de pyridino-pyridinones arylsulfonamides, leur preparation et leur application en therapeutique |
| FR2955109B1 (fr) * | 2010-01-08 | 2012-09-07 | Sanofi Aventis | Derives de 5-oxo-5,8-dihydro-pyrido[2, 3-d]pyrimidine, leur preparation et leur application en therapeutique |
| WO2012009097A1 (en) * | 2010-06-17 | 2012-01-19 | Cytokinetics, Inc. | Methods of treating lung disease |
| WO2013072882A1 (en) * | 2011-11-18 | 2013-05-23 | Actelion Pharmaceuticals Ltd | 2 -amino- 1, 8 -naphthyridine-3 -carboxamide derivatives as antimicrobial agents |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE258437T1 (de) | 1995-08-02 | 2004-02-15 | Darwin Discovery Ltd | Chinolone und deren therapeutische verwendung |
| AU763636C (en) | 1998-01-29 | 2004-05-27 | Daiichi Asubio Pharma Co., Ltd. | 1-cycloalkyl-1,8-naphthyridin-4-one derivatives with phosphodiesterase IV inhibitory activity |
| DE19826050A1 (de) * | 1998-06-12 | 1999-12-16 | Bayer Ag | Verfahren zur Herstellung von Chinolon- und Naphthyridoncarbonsäuren und deren Ester |
| WO2002090352A2 (de) | 2001-05-08 | 2002-11-14 | Schering Aktiengesellschaft | Selektive anthranylamidpyridinamide als vegfr-2 und vegfr-3 inhibitoren |
| JP4460221B2 (ja) | 2001-05-24 | 2010-05-12 | メルク フロスト カナダ リミテツド | １−ビアリール−１，８−ナフチリジン−４−オン系ホスホジエステラーゼ−４阻害薬 |
| US7148357B2 (en) | 2002-07-31 | 2006-12-12 | Schering Ag | VEGFR-2 and VEGFR-3 inhibitory anthranilamide pyridines |
| WO2005118587A1 (en) * | 2004-06-02 | 2005-12-15 | Takeda Pharmaceutical Company Limited | Indole derivative and use for treatment of cancer |
| FR2917412B1 (fr) * | 2007-06-13 | 2009-08-21 | Sanofi Aventis Sa | Derives de 7-alkynyl, 1,8-naphthyridones, leur preparation et leur application en therapeutique |
-
2007
- 2007-06-13 FR FR0704193A patent/FR2917413B1/fr not_active Expired - Fee Related
-
2008
- 2008-06-11 ES ES08826271T patent/ES2366629T3/es active Active
- 2008-06-11 AU AU2008274100A patent/AU2008274100B2/en active Active
- 2008-06-11 KR KR1020097025902A patent/KR20100019507A/ko active IP Right Grant
- 2008-06-11 PT PT08826271T patent/PT2158194E/pt unknown
- 2008-06-11 DK DK08826271.2T patent/DK2158194T3/da active
- 2008-06-11 BR BRPI0813809-5A patent/BRPI0813809B1/pt active IP Right Grant
- 2008-06-11 PL PL08826271T patent/PL2158194T3/pl unknown
- 2008-06-11 JP JP2010511681A patent/JP5346337B2/ja active Active
- 2008-06-11 EA EA201070010A patent/EA016552B1/ru not_active IP Right Cessation
- 2008-06-11 MY MYPI20095317A patent/MY146939A/en unknown
- 2008-06-11 EP EP08826271A patent/EP2158194B1/fr active Active
- 2008-06-11 WO PCT/FR2008/000794 patent/WO2009007536A2/fr active Application Filing
- 2008-06-11 ME MEP-2009-334A patent/ME00957B/me unknown
- 2008-06-11 IN IN4279KON2009 patent/IN2009KN04279A/en unknown
- 2008-06-11 MX MX2009013514A patent/MX2009013514A/es active IP Right Grant
- 2008-06-11 AR ARP080102478A patent/AR066955A1/es unknown
- 2008-06-11 AT AT08826271T patent/ATE509923T1/de active
- 2008-06-11 CN CN200880020155.4A patent/CN101815715B/zh active Active
- 2008-06-11 CA CA2690349A patent/CA2690349C/fr active Active
- 2008-06-11 SI SI200830319T patent/SI2158194T1/sl unknown
- 2008-06-11 NZ NZ581883A patent/NZ581883A/en not_active IP Right Cessation
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2009
- 2009-12-04 US US12/631,130 patent/US8263614B2/en active Active
- 2009-12-10 IL IL202677A patent/IL202677A/en not_active IP Right Cessation
- 2009-12-11 CO CO09142107A patent/CO6150157A2/es unknown
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- 2010-01-12 MA MA32509A patent/MA31674B1/fr unknown
- 2010-10-28 HK HK10110153.0A patent/HK1143590A1/xx not_active IP Right Cessation
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- 2011-07-25 HR HR20110550T patent/HRP20110550T1/hr unknown
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