HRP20140015T1 - Antitumorski spojevi - Google Patents
Antitumorski spojevi Download PDFInfo
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- HRP20140015T1 HRP20140015T1 HRP20140015AT HRP20140015T HRP20140015T1 HR P20140015 T1 HRP20140015 T1 HR P20140015T1 HR P20140015A T HRP20140015A T HR P20140015AT HR P20140015 T HRP20140015 T HR P20140015T HR P20140015 T1 HRP20140015 T1 HR P20140015T1
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- 150000001875 compounds Chemical class 0.000 title claims abstract 34
- 230000000259 anti-tumor effect Effects 0.000 title 1
- 206010028980 Neoplasm Diseases 0.000 claims abstract 3
- 201000011510 cancer Diseases 0.000 claims abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 239000001257 hydrogen Substances 0.000 claims 21
- 150000002431 hydrogen Chemical class 0.000 claims 12
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 11
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 10
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 238000000034 method Methods 0.000 claims 8
- 239000012634 fragment Substances 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 241000689227 Cora <basidiomycete fungus> Species 0.000 claims 3
- 229910003827 NRaRb Inorganic materials 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- 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
- A61K31/695—Silicon compounds
-
- 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
-
- 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)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Dermatology (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compounds Of Unknown Constitution (AREA)
- Steroid Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (33)
1. Spoj opće formule I
[image]
,
naznačen time, što se
Y bira između -CHRay-, -CHRay-CHRby-, -CRay=CRby-, -C≡C-, -CHRay-CHRby-CHRCy-, -CHRay-CRby=CRCy-, i -CHRay-C≡C-;
svaki Ray, Rby, i Rcy se neovisno bira između vodika, supstituiranog ili nesupstituiranog C1-C12 alkila, supstituiranog ili nesupstituiranog C2-C12 alkenila, i supstituiranog ili nesupstituiranog C2-C12 alkinila;
svaki R1, R2, R3, R4, i R5 se neovisno bira između vodika, supstituiranog ili nesupstituiranog C1-C12 alkila, supstituiranog ili nesupstituiranog C2-C12 alkenila, i supstituiranog ili nesupstituiranog C2-C12 alkinila;
R6 se bira između NR8R9, i OR10;
A je
[image]
W se bira između O i NR7;
R7 se bira između 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 skupa sa odgovarajućim N atomom i C atomom za koje su pričvršćeni mogu da formiraju supstituiranu ili nesupstituiranu heterocikličnu grupu;
R8 se bira između vodika, CORa, COORa supstituiranog ili nesupstituiranog C1-C12 alkila, supstituiranog ili nesupstituiranog C2-C12 alkenila, supstituiranog ili nesupstituiranog C2-C12 alkinila, i supstituiranog ili nesupstituiranog C4-C12 alkeninila;
R10 se bira između vodika, supstituiranog ili nesupstituiranog C1-C12 alkila, supstituiranog ili nesupstituiranog C2-C12 alkenila, i supstituiranog ili nesupstituiranog C2-C12 alkinila; svaka isprekidana linija predstavlja opcijsku dodatnu vezu ali, kada postoji troguba veza između C atoma za koje su prikačeni R1 i R2, R1 i R2 su odsutni, i kada postoji troguba veza između C atoma za koje su prikačeni R3 i R4. R3 i R4 su odsutni;
R9 se bira između vodika, CORa, COORa, supstituiranog ili nesupstituiranog C1-C12 alkila, supstituiranog ili nesupstituiranog C2-C12 alkenila, supstituiranog ili nesupstituiranog C2-C12 alkinila, i supstituiranog ili nesupstituiranog C4-C12 alkeninila, uz uvjet da kada je Y - CHRay-CHRby-CHRCy- ili -CHRay-CRby=CRCy- i postoji jednoguba ili dvoguba veza između C atoma za koje su prikačeni R3 i R4, onda je R9 supstituirani ili nesupstituiraniC4-C12 alkeninil;
R16, R17 i R18 se neovisno biraju između vodika, ORa, OCORa, OCOORa, NRaRb, NRaCORb, i NRaC(=NRa)NRaRb, supstituiranog ili nesupstituiranog C1-C12 alkila, supstituiranog ili nesupstituiranog C2-C12 alkenila i supstituiranog ili nesupstituiranog C2-C12 alkinila;
svaki Ra, i Rb, se neovisno bira između vodika, supstituirane ili nesupstituirane C1-C12 alkil, supstituirane ili nesupstituirane C2-C12 alkenil i supstituirane ili nesupstituirane C2-C12 alkinil, supstituirane ili nesupstituirane aril i supstituirane ili nesupstituirane heterociklične grupe; ili
farmaceutski prihvatljiva sol, tautomer ili stereoizomer istoga.
2. Spoj prema zahtjevu 1, naznačen time, što se R16 bira između vodika, ORa i OCORa, gde se Ra bira između vodika i supstituiranog ili nesupstituiranog C1-C6 alkila.
3. Spoj prema zahtjevu 2, naznačen time, što se R16 bira između vodika, OH i metoksi.
4. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time, što je jedna dodatna veza prisutna između C atoma za koje su prikačeni R16 i R17.
5. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time, što su R17 i R18 vodik.
6. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time, što se R1, R2, R3 i R4 neovisno biraju između vodika i supstituiranog ili nesupstituiranog C1-C6 alkila.
7. Spoj prema zahtjevu 6, naznačen time, što su R1, R2, R3 i R4 vodik.
8. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time, što se Y bira između -CHRay-, -CRay=CRby- i -CHRay-CRby=CRCy-, i gdje se Ray, Rby i RCy neovisno biraju između vodika i supstituiranog ili nesupstituiranog C1-C6 alkila.
9. Spoj prema zahtjevu 8, naznačen time, što se Ray, Rby i Rcy neovisno biraju između vodika i metila.
10. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time, što se R5 bira između vodika i supstituiranog ili nesupstituiranog C1-C6 alkila.
11. Spoj prema zahtjevu 10, naznačen time, što se R5 bira između metila, izopropila i tert-butila.
12. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time, što je W NR7 i gdje je R7 kako je definirano u zahtjevu 1.
13. Spoj prema zahtjevu 12, naznačen time, što je R7 vodik.
14. Spoj prema bilo kojem od zahtjeva 1 do 9, naznačen time, što je W NR7 i gdje R7 i R5 skupa sa odgovarajućim N atomom i C atomom za koje su prikačeni formiraju supstituiranu ili nesupstituiranu pirolidinsku grupu.
15. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time, što je R6 NR8R9 i gdje je R8 vodik i R9 se bira između vodika, supstituiranog ili nesupstituiranog C1-C12 alkila, supstituiranog ili nesupstituiranog C2-C12 alkenila, supstituiranog ili nesupstituiranog C2-C12 alkinila i supstituiranog ili nesupstituiranog C4-C12 alkeninila.
16. Spoj prema zahtjevu 15, naznačen time, što se R9 bira između supstituiranog C2-C12 alkenila i supstituiranog C4-C12 alkeninila koji su na jednoj ili više pozicija supstituirani halogenom, OR’, =O, OCOR’, OCONHR’, OCONR’R’, CONHR’, CONR’R’ i protektiranom OH grupom, gdje se svaka od R' grupa neovisno bira između vodika, supstituiranog ili nesupstituiranog C1-C12 alkila, supstituiranog ili nesupstituiranog C2-C12 alkenila, supstituiranog ili nesupstituiranog C2-C12 alkinila i supstituiranog ili nesupstituiranog arila.
17. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time, što je jedna dodatna veza prisutna između C atoma za koje su prikačeni R1 i R2 i jedna ili dvije dodatne veze su prisutne između C atoma za koje su prikačeni R3 i R4.
18. Spoj prema zahtjevu 1, naznačen time, što ima formulu:
[image]
[image]
[image]
[image]
[image]
ili farmaceutski prihvatljiva sol, tautomer ili stereoizomer istoga.
19. Farmaceutska smjesa, naznačena time, što sadrži spoj prema bilo kojem od prethodnih zahtjeva, ili farmaceutski prihvatljivu sol, tautomer ili stereoizomer istoga,
i farmaceutski prihvatljivi razblaživač ili nosač.
20. Spoj ili smjesa prema bilo kojem od zahtjeva 1 do 19, ili farmaceutski prihvatljiva sol, tautomer ili stereoizomer istoga, naznačeni time, što se upotrebljavaju kao lijek.
21. Spoj ili smjesa prema bilo kojem od zahtjeva 1 do 19, ili farmaceutski prihvatljiva sol, tautomer ili stereoizomer istoga, naznačeni time, što se upotrebljavaju u liječenju kancera.
22. Upotreba spojeva ili smijese prema bilo kojem od zahtjeva 1 do 19, ili farmaceutski prihvatljive soli, tautomera ili stereoizomera istoga, naznačena time, što se koristi za izradu lijeka za liječenje kancera.
23. Postupak za pripremanje spoja prema formuli I
[image]
kako je definirano u zahtjevima 1 do 18, gdje su A, Y, W, R1, R2, R3, R4, R5 i R6 također kako je definirano u bilo kojem od zahtjeva 1 do 18, naznačen time, što uključuje kuplovanje fragmenata C i D
[image]
gdje su R1, R2, R3, R4, R5, R6, A, Y i W željene grupe kako je definirano u spoju formule I ili pogodna protektivna grupa po potrebi, i L i M su pogodna reaktivna ili odlazeća grupa.
24. Postupak prema zahtjevu 23, naznačen time, što je spoj formule I bilo koji spoj definiran u zahtjevu 18.
25. Postupak prema bilo kojem od zahtjeva 23 do 24, naznačen time, što je odlazeća grupa "L" jodid.
26. Postupak prema bilo kojem od zahtjeva 23 do 25, naznačen time, što je reaktivna grupa "M" tributil kalaj.
27. Postupak prema bilo kojem od zahtjeva 23 do 26, naznačen time, što je fragment D:
[image]
28. Postupak prema bilo kojem od zahtjeva 23 do 26, naznačen time, što je fragment D:
[image]
29. Spoj prema definiciji fragmenta D zahtjeva 23, naznačen time, što je
[image]
30. Spoj prema definiciji fragmenta D zahtjeva 23, naznačen time, što je
[image]
31. Spoj prema definiciji fragmenta D zahtjeva 23, naznačen time, što je
[image]
32. Postupak za pripremanje spoja prema formuli I
[image]
kako je definirano u bilo kojem od zahtjeva 1 do 18, gdje su A, Y, W, R1, R2, R3, R4, R5 i R6 također kako je definirano u bilo kojem od zahtjeva 1 do 18, naznačen time, što uključuje kuplovanje fragmenata A i B
[image]
gdje su R1, R2, R3, R4, R5, R6, A, i Y željene grupe ili pogodna protektivna grupa po potrebi, i J i K su pogodna reaktivna ili odlazeća grupa.
33. Postupak prema zahtjevu 32, naznačen time, što je spoj formule I bilo koji spoj definiran u zahtjevu 18.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07123882 | 2007-12-20 | ||
| PCT/EP2008/068049 WO2009080761A1 (en) | 2007-12-20 | 2008-12-19 | Antitumoral compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20140015T1 true HRP20140015T1 (hr) | 2014-02-14 |
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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 Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20120464AT HRP20120464T1 (hr) | 2007-12-20 | 2012-06-01 | Antitumorski spojevi |
Country Status (27)
| Country | Link |
|---|---|
| US (4) | US9187445B2 (hr) |
| EP (3) | EP2597091B1 (hr) |
| JP (3) | JP5529038B2 (hr) |
| KR (3) | KR101579553B1 (hr) |
| CN (4) | CN102174058A (hr) |
| AT (1) | ATE549313T1 (hr) |
| AU (2) | AU2008341670B2 (hr) |
| BR (2) | BRPI0821114B8 (hr) |
| CA (2) | CA2710087C (hr) |
| CY (1) | CY1117245T1 (hr) |
| DK (2) | DK2231590T3 (hr) |
| ES (3) | ES2578606T3 (hr) |
| HK (3) | HK1147998A1 (hr) |
| HR (2) | HRP20120464T1 (hr) |
| IL (3) | IL206397A (hr) |
| MX (2) | MX2010006796A (hr) |
| MY (3) | MY155342A (hr) |
| NZ (3) | NZ597526A (hr) |
| PL (2) | PL2231590T3 (hr) |
| PT (2) | PT2231590E (hr) |
| RS (2) | RS53140B (hr) |
| RU (3) | RU2489429C2 (hr) |
| SG (2) | SG170778A1 (hr) |
| SI (2) | SI2231590T1 (hr) |
| UA (3) | UA104281C2 (hr) |
| WO (2) | WO2009080761A1 (hr) |
| ZA (3) | ZA201004017B (hr) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA104281C2 (ru) | 2007-12-20 | 2014-01-27 | Фарма Мар, С.А. | Противоопухолевые аналоги пептидов, способ их получения и фармацевтическая композиция на них основе |
| WO2013103155A1 (en) * | 2012-01-05 | 2013-07-11 | Kao Corporation | Agent for reduction of sensory irritation |
| BR112015026261A8 (pt) | 2013-04-16 | 2017-12-26 | Actelion Pharmaceuticals Ltd | Derivados biaromáticos antibacterianos |
| GB201309807D0 (en) | 2013-05-31 | 2013-07-17 | Pharma Mar Sau | Antibody drug conjugates |
| CN108467378A (zh) * | 2017-02-23 | 2018-08-31 | 复旦大学 | 一种二氢吡喃酮类化合物及其制备方法和用途 |
| JOP20190254A1 (ar) | 2017-04-27 | 2019-10-27 | Pharma Mar Sa | مركبات مضادة للأورام |
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