HRP20120464T1 - Antitumorski spojevi - Google Patents
Antitumorski spojevi Download PDFInfo
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- HRP20120464T1 HRP20120464T1 HRP20120464AT HRP20120464T HRP20120464T1 HR P20120464 T1 HRP20120464 T1 HR P20120464T1 HR P20120464A T HRP20120464A T HR P20120464AT HR P20120464 T HRP20120464 T HR P20120464T HR P20120464 T1 HRP20120464 T1 HR P20120464T1
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- 150000001875 compounds Chemical class 0.000 title claims abstract 31
- 230000000259 anti-tumor effect Effects 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 23
- 239000001257 hydrogen Substances 0.000 claims 23
- 150000002431 hydrogen Chemical class 0.000 claims 13
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 11
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 241000689227 Cora <basidiomycete fungus> Species 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 229910003827 NRaRb Inorganic materials 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000012634 fragment Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 238000005304 joining Methods 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 101150073096 NRAS gene Proteins 0.000 claims 1
- -1 SO2NRaRb Inorganic materials 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- MPVDXIMFBOLMNW-UHFFFAOYSA-N chembl1615565 Chemical group OC1=CC=C2C=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1N=NC1=CC=CC=C1 MPVDXIMFBOLMNW-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
Classifications
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- 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
- A61K31/695—Silicon compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/51—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/351—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom not condensed with another ring
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
-
- 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
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/30—Oxygen atoms, e.g. delta-lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Peptides Or Proteins (AREA)
- Dermatology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Compounds Of Unknown Constitution (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Spoj opće formule I
Claims (27)
1. Spoj opće formule I
[image]
u kojem je Y izabran od -CHRay-, -CHRay-CHRby-, -CRay=CRby-, -C≡C-, -CHRay-CHRby-CHRCy-, -CHRay-CRby=CRCy- i -CHRay-C≡C-;
svako Ray, Rby i RCy je nezavisno izabrano od vodika, supstituiranog ili nesupstituiranog C1-C12 alkila, supstituiranog ili nesupstituiranog C2-C12 alkenila i supstituiranog ili nesupstituiranog C2-C12 alkinila;
svako R1, R2, R3, R4 i R5 je nezavisno izabrano od vodika, supstituiranog ili nesupstituiranog C1-C12 alkila, supstituiranog ili nesupstituiranog C2-C12 alkenila i supstituiranog ili nesupstituiranog C2-C12 alkinila;
R6 je izabran od NR8R9 i OR10;
W je izabran od O i NR7;
R7 je izabran od vodika, CORa, COORa, supstituiranog ili nesupstituiranog C1-C12 alkila, supstituiranog ili nesupstituiranog C2-C12 alkenila i supstituiranog ili nesupstituiranog C2-C12 alkinila, ili R7 i R5 zajedno sa odgovarajućim N atomom i C atomom za koji su vezani formiraju supstituiranu ili nesupstituiranu heterocikličnu grupu;
R8 je izabran od vodika, CORa, COORa, supstituiranog ili nesupstituiranog C2-C12 alkenila, supstituiranog ili nesupstituiranog C2-C12 alkinila i supstituiranog ili nesupstituiranog C4-C12 alkeninila;
R10 je izabran od vodika, supstituiranog ili nesupstituiranog C2-C12 alkenila i supstituiranog ili nesupstituiranog C2-C12 alkinila;
svaka isprekidana linija predstavlja izbornu dodatnu vezu uz uvjet da su prisutne jedna ili više dodatnih veza, ali kada trostruka veza postoji između C atoma za koje su vezani R1 i R2, tada su R1 i R2 odsutni, i kada trostruka veza postoji između C atoma za koje su vezani R3 i R4, tada su R3 i R4 odsutni;
R9 je izabran od vodika, CORa, COORa, supstituiranog ili nesupstituiranog C2-C12 alkenila, supstituiranog ili nesupstituiranog C2-C12 alkinila i supstituiranog ili nesupstituiranog C4-C12 alkeninila;
svaki R11, R12, R13, R14 i R15 nezavisno su izabrani od vodika, halogena, ORa, CORa, COORa, OCORa, OCOORa, OCONRaRb, CONRaRb, OS(O)Ra, OSO2Ra, OP(O)(Ra)ORb, OSiRaRbRC, NRaRb, NRaCORb, NRaCONRaRb, NRaS(O)Rb, NRaSO2Rb, NRaC(=NRa)NRaRb, SRa, S(O)Ra, SO2Ra, S(O)NRaRb, SO2NRaRb, S(O)ORa, SO2ORa, supstituiranog ili nesupstituiranog C1-C12 alkila, supstituiranog ili nesupstituiranog C2-C12 alkenila i supstituiranog ili nesupstituiranog C2-C12 alkinila; i
svaki Ra, Rb i RC nezavisno su izabrani od vodika, supstituiranog ili nesupstituiranog C1-C12 alkila, supstituiranog ili nesupstituiranog C2-C12 alkenila, supstituiranog ili nesupstituiranog C2-C12 alkinila, supstituiranog ili nesupstituiranog arila i supstituirane ili nesupstituirane heterociklične grupe; ili njegova farmaceutski prihvatljiva sol, tautomer ili stereoizomer.
2. Spoj prema patentnom zahtjevu 1, naznačen time što su R1, R2, R3 i R4 nezavisno izabrani od vodika i supstituiranog ili nesupstituiranog C1-C6 alkila.
3. Spoj prema patentnom zahtjevu 2, naznačen time što su R1, R2, R3 i R4 jednaki vodik.
4. Spoj prema bilo kojem prethodnom patentnom zahtjevu, naznačen time što su R11, R14 i R15 jednaki vodik.
5. Spoj prema bilo kojem prethodnom patentnom zahtjevu, naznačen time što je Y izabran od -CHRay-, -CRay=CRby- i -CHRay-CRby=CRCy-, i što su Ray, Rby i RCy nezavisno izabrani od vodika i supstituiranog ili nesupstituiranog C1-C6 alkila.
6. Spoj prema patentnom zahtjevu 5, naznačen time što su Ray, Rby i RCy nezavisno izabrani od vodika i metila.
7. Spoj prema bilo kojem prethodnom patentnom zahtjevu, naznačen time što su R12 i R13 nezavisno izabrani od vodika, ORa, OCORa i OSiRaRbRC, i što su Ra, Rb i RC nezavisno izabrani od vodika i supstituiranog ili nesupstituiranog C1-C6 alkila.
8. Spoj prema patentnom zahtjevu 7, naznačen time što je R12 izabran od vodika i ORa.
9. Spoj prema patentnom zahtjevu 7 ili 8, naznačen time što je R13 izabran od vodika, ORa i OSiRaRbRC.
10. Spoj prema bilo kojem od patentnih zahtjeva 7 do 9, naznačen time što su Ra, Rb i RC nezavisno izabrani od vodika, supstituiranog ili nesupstituiranog metila, supstituiranog ili nesupstituiranog etila, supstituiranog ili nesupstituiranog propila, supstituiranog ili nesupstituiranog izopropila, supstituiranog ili nesupstituiranog terc-butila.
11. Spoj prema bilo kojem prethodnom patentnom zahtjevu, naznačen time što je R5 izabran od vodika i supstituiranog ili nesupstituiranog C1-C6 alkila.
12. Spoj prema patentnom zahtjevu 11, naznačen time što je R5 izabran od metila, izopropila i terc-butila.
13. Spoj prema bilo kojem prethodnom patentnom zahtjevu, naznačen time što, W je NR7 i R7 je kao što je definiran u patentnom zahtjevu 1.
14. Spoj prema patentnom zahtjevu 13, naznačen time što, R7 je vodik.
15. Spoj prema bilo kojem od patentnih zahtjeva 1 do 10, naznačen time što, W je NR7 i što R7 i R5 zajedno sa odgovarajućim N atomom i C atomom za koji su vezani formiraju supstituiranu ili nesupstituiranu pirolidin grupu.
16. Spoj prema bilo kojem prethodnom patentnom zahtjevu, naznačen time što, R6 je NR8R9 i što, R8 je vodik i R9 je izabran od vodika, supstituiranog ili nesupstituiranog C2-C12 alkenila, supstituiranog ili nesupstituiranog C2-C12 alkinila i supstituiranog ili nesupstituiranog C4-C12 alkeninila.
17. Spoj prema patentnom zahtjevu 16, naznačen time što je R9 supstituirani C2-C12 alkenil koji je supstituiran na jednom ili više položaja sa halogenom, OR', =O, OCOR', OCONHR', OCONR'R', CONHR', CONR'R' i zaštićenim OH, pri čemu je svaka od R' grupa nezavisno izabrana od vodika, supstituiranog ili nesupstituiranog C1-C12 alkila, supstituiranog ili nesupstituiranog C2-C12 alkenila, supstituiranog ili nesupstituiranog C2-C12 alkinila i supstituiranog ili nesupstituiranog arila.
18. Spoj prema bilo kojem prethodnom patentnom zahtjevu, naznačen time što je jedna dodatna veza prisutna između C atoma za koje su vezani R1 i R2 i druga dodatna veza je prisutna između C atoma za koje su vezani R3 i R4.
19. Spoj prema patentnom zahtjevu 1, koji ima slijedeću formulu
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ili njegova farmaceutski prihvatljiva sol, tautomer ili stereoizomer.
20. Farmaceutska kompozicija koja sadrži spoj prema bilo kojem prethodnom patentnom zahtjevu, ili njegovu farmaceutski prihvatljivu sol, tautomer ili stereoizomer, i farmaceutski prihvatljiv razblaživač ili nosač.
21. Spoj ili kompozicija prema bilo kojem od patentnih zahtjeva 1 do 20, ili njegova farmaceutski prihvatljiva sol, tautomer ili stereoizomer, za upotrebu kao lijek.
22. Spoj ili kompozicija prema bilo kojem od patentnih zahtjeva 1 do 20, ili njegova farmaceutski prihvatljiva sol, tautomer ili stereoizomer, za upotrebu u liječenju kancera.
23. Spoj ili kompozicija prema bilo kojem od patentnih zahtjeva 1 do 20, ili njegova farmaceutski prihvatljiva sol, tautomer ili stereoizomer, u proizvodnji lijeka za liječenje kancera.
24. Postupak za pripremu spojeva prema formuli I
[image]
kao što je definirano u bilo kojem od patentnih zahtjeva 1 do 19, pri čemu su Y, W i R1, R2, R3, R4, R5, R6, R11, R12, R13, R14 i R15 također kao što su definirani u bilo kojem od patentnih zahtjeva 1 do 19
koji sadrži spajanje fragmenata C i D
[image]
pri čemu, R1, R2, R3, R4, R5, R6, R11, R12, R13, R14, R15, Y i W su željene grupe ili odgovarajuća zaštitna grupa prema potrebi, i L i M su odgovarajuće reaktivne ili odlazeće grupe.
25. Postupak prema patentnom zahtjevu 24, naznačen time što je spoj formule I – bilo koji spoj definiran u patentnom zahtjevu 19.
26. Postupak za pripremu spojeva prema formuli I
[image]
kao što je definirano u bilo kojem od patentnih zahtjeva 1 do 19, pri čemu, Y, W i R1, R2, R3, R4, R5, R6, R11, R12, R13, R14 i R15 su također kao što su definirani u bilo kojem od patentnih zahtjeva 1 do 19
koji sadrži spajanje fragmenata A i B
[image]
pri čemu, R1, R2, R3, R4, R5, R6, R11, R12, R13, R14, R15 i Y su željene grupe ili odgovarajuća zaštitna grupa prema potrebi, i J i K su odgovarajuće reaktivne ili odlazeće grupe.
27. Postupak prema patentnom zahtjevu 26, naznačen time što je spoj formule I bilo koji spoj definiran u patentnom zahtjevu 19.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP07123882 | 2007-12-20 | ||
PCT/EP2008/068065 WO2009080769A1 (en) | 2007-12-20 | 2008-12-19 | Antitumoral compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20120464T1 true HRP20120464T1 (hr) | 2012-07-31 |
Family
ID=40580474
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20120464AT HRP20120464T1 (hr) | 2007-12-20 | 2012-06-01 | Antitumorski spojevi |
HRP20140015AT HRP20140015T1 (hr) | 2007-12-20 | 2014-01-08 | Antitumorski spojevi |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20140015AT HRP20140015T1 (hr) | 2007-12-20 | 2014-01-08 | Antitumorski spojevi |
Country Status (27)
Country | Link |
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US (4) | US8710264B2 (hr) |
EP (3) | EP2231633B1 (hr) |
JP (3) | JP5529038B2 (hr) |
KR (3) | KR101639772B1 (hr) |
CN (4) | CN101903337B (hr) |
AT (1) | ATE549313T1 (hr) |
AU (2) | AU2008341670B2 (hr) |
BR (2) | BRPI0821116B8 (hr) |
CA (2) | CA2710087C (hr) |
CY (1) | CY1117245T1 (hr) |
DK (2) | DK2231633T3 (hr) |
ES (3) | ES2578606T3 (hr) |
HK (3) | HK1147990A1 (hr) |
HR (2) | HRP20120464T1 (hr) |
IL (3) | IL206396A (hr) |
MX (2) | MX2010006795A (hr) |
MY (3) | MY148651A (hr) |
NZ (3) | NZ586013A (hr) |
PL (2) | PL2231633T3 (hr) |
PT (2) | PT2231633E (hr) |
RS (2) | RS53140B (hr) |
RU (3) | RU2528393C9 (hr) |
SG (2) | SG170779A1 (hr) |
SI (2) | SI2231590T1 (hr) |
UA (3) | UA104281C2 (hr) |
WO (2) | WO2009080761A1 (hr) |
ZA (3) | ZA201004017B (hr) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NZ586013A (en) | 2007-12-20 | 2012-02-24 | Pharma Mar Sa | Antitumoral compounds |
EP2800559B1 (en) * | 2012-01-05 | 2018-09-05 | Kao Corporation | Agent for reduction of sensory irritation |
AU2014255326B2 (en) | 2013-04-16 | 2018-09-13 | Idorsia Pharmaceuticals Ltd | Antibacterial biaromatic derivatives |
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