ME00376B - DIHIDROPTERIDINONI, POSTUPAK ZA NJlHOVO PRIPREMANJE I NJlHOVA PRIMJENA KAO LIJEK - Google Patents
DIHIDROPTERIDINONI, POSTUPAK ZA NJlHOVO PRIPREMANJE I NJlHOVA PRIMJENA KAO LIJEKInfo
- Publication number
- ME00376B ME00376B MEP-2008-588A MEP58808A ME00376B ME 00376 B ME00376 B ME 00376B ME P58808 A MEP58808 A ME P58808A ME 00376 B ME00376 B ME 00376B
- Authority
- ME
- Montenegro
- Prior art keywords
- group
- alkyl
- denotes
- aryl
- given case
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims abstract 5
- 238000000034 method Methods 0.000 title claims abstract 3
- 229940079593 drug Drugs 0.000 title claims 3
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- 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 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000005647 linker group Chemical group 0.000 claims 3
- -1 piperazinylcarbonyl Chemical group 0.000 claims 3
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 claims 2
- 229910003204 NH2 Inorganic materials 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 125000006217 methyl sulfide group Chemical group [H]C([H])([H])S* 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 150000002829 nitrogen Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 230000001028 anti-proliverative effect Effects 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000005592 polycycloalkyl group Polymers 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Ovaj pronalazak odnosi se, na nove dihidropteridinone, opšte formule (I), pri čemu ostaci L, R 1 , R 2 , R 3 , R 4 i R 5 imaju značenja navedena u patentnim zahtevima i u opisu, na njihove izomere, na postupak za pripremanje ovih dihidropteridinona, kao i na njihovu primenu kao lekova.
Claims (12)
1.Jedinjenja opšte formule (I), u kojoj R1, R2, koji mogu biti isti ili različiti, označavaju vodonik ili, u datom slučaju, supstituisanu C1-C6-alkil grupu, ili R1 i R2, zajedno označavaju, 2- do 5-člani alkil most, koji može da sadrži 1 do 2 heteroatoma, R3 označava vodonik ili ostatak odabran iz grupe koju čine, u datom slučaju, supstituisana C1-C12-alkil, C1-C12-alkenil, C1-C12-alkinil i C6-C14-aril grupa, ili ostatak odabran iz grupe koju čine, u datom slučaju, supstituisana i/ili premošćavajuća C3-C12-cikloalkil, C3-C12-cikloalkenil, C7-C 12-policikloalkil, C7-C12-policikloalkenil, C5-C12-spirocikloalkil grupa, C3-C12-heterocikloalkil grupa koja sadrži 1 do 2 heteroatoma, i C3-C12-heterocikloalkenil grupa koja sadrži 1 do 2 heteroatoma, ili R1 i R3, ili R2 i R3, zajedno, označavaju zasićen ili nezasićen C3-C4-alkil most, koji može da sadrži 1 heteroatom, R4 označava ostatak odabran od, vodonika, -CN, hidroksi, -NR6R7 grupe i halogena, ili ostatak odabran iz grupe koju čine, u datom slučaju, supstituisana C1-C6-alkil, C2-C6-alkenil, C2-C6-alkinil, C1-C5-alkiloksi, C2-C5-alkeniloksi, C2-C5-alkiniloksi, C1-C6-alkiltio, C1-C6-alkilsulfokso i C1-C6-alkilsulfonil grupa, L označava veznu grupu odabranu iz grupe koju čine, u datom slučaju, supstituisana C2-C10-alkil, C2-C10-alkenil, C6-C14-aril, -C2-C4-alkil-C6-C14-aril, -C6-C14-aril-C1-C4-alkil, u datom slučaju, premošćavajuća C3-C12-cikloalkil grupa i heteroaril grupa, koja sadrži 1 ili 2 atoma azota, n označava 0 ili 1 m označava 1 ili 2 R5 označava ostatak odabran iz grupe koju čine, u datom slučaju, supstituiana morfolinil, piperidinil, piperazinil, piperazinilkarbonil, pirolidinil, tropenil, R8-diketo-metilpiperazinil, sulfoksomorfolinil, sulfonilmorfolinil, tiomorfolinil, -NR8R9 i azacikloheptil grupa, R6, R7, koji mogu biti isti ili različiti, označavaju vodonik ili C1-C4-alkil grupu, a R8, R9 označavaju nesupstituisane azotne supstituente na R5, koji mogu biti isti ili različiti, ili vodonik ili ostatak odabran iz grupe koju čine C1 -C6-alkil, -C1 -C4-alkil-C3-C10-cikloalkil, C3-C10-cikloalkil, C6 -C14-aril,-C1 -C4-alkil-C6-C14-aril, piranil, piridinil, pirimidinil, C1 -C4-alkiloksikarbonil, C6 -C14- alkilkarbonil, C1 -C4-alkilkarbonil, C6-C14-arilmetiloksikarbonil, C6-C14-arilsulfonil, C1 -C4-alkilsulfonil- i C6-C14-aril-C1 -C4-alkilsulfonil- grupa, u datom slučaju, u obliku svojih tautomera, svojih racemata, svojih enantiomera, svojih dijastereomera i svojih smeša, kao i, u datom slučaju, svojih farmakološki prihvatljivih adicionih soli sa kiselinom. 1.Jedinjenja opšte formule (I), u kojoj R1 do R4, R6 i R7 imaju prethodno navedena značenja, a L označava veznu grupu, odabranu iz grupe koju čine, u datom slučaju, supstitui-sana C2-C10-alkil, C2-C10-alkenil, C6-C14-aril, -C2-C4-alkil-C6-C14aril, -C6-C14-aril-C1-C4-alkil grupa, u datom slučaju, premošćavajuća C3-C12-cikloalkil grupa i heteroaril grupa, koja sadrži 1 ili 2 atoma azota, n označava 1 m označava 1 ili 2 R5 označava ostatak koji je preko atoma azota vezan za L, odabran iz grupe koju čine, u datom slučaju, supstituisana morfolinil, piperidinil, R8-piperazinil, pirolidinil, tropenil, R8-diketometilpiperazinil, sulfoksomorfolinil, sulfonilmorfolinil, tiomorfolinil, -NR8R9 i azacikloheptil grupa, R8, R9 označavaju nesupstituisane azotne supstituente na R5, koji mogu biti isti ili različiti, vodonik ili ostatak izabran iz grupe koju čine, C1-C6-alkil, -C1-C4-alkil-C3-C10-cikloalkil, C3-C10-cikloalkil, C6-C14-aril, -C1-C4-alkil-C6-C14-aril, piranil, piridinil, pirimidinil, C1-C4-alkiloksikarbonil, C6-C14-arilkarbonil, C1-C4-alkilkarbonil, C6-C14-arilmetiloksikarbonil, C6-C14-arilsulfo-nil, C1-C4-alkilsulfonil i C6-C14-aril-C1-C4-alkilsulfonil grupa, u datom slučaju, u obliku svojih tautomera, svojih racemata, svojih enantiomera, svojih dijastereomera i svojih smeša, kao i, u datom slučaju, svojih farmakološki prihvatljivih adicionih soli sa kiselinom.
2. Jedinjenja prema zahtevu 1, u kojima R1 do R4, R6 i R7 imaju prethodno navedena značenja, L označava veznu grupu, odabranu iz grupe koju čine, u datom slučaju, supstitui-sana C2-C10-alkil, C2-C10-alkenil, C6-C14-aril, -C2-C4-alkil-C6-C14-aril, -C6-C14-aril-C1-C4-alkil, u datom slučaju, premošćavajuća C3-C12-cikloalkil grupa i heteroaril grupa koja sadrži 1 ili 2 atoma azota, n označava 0 ili 1 m označava 1 ili 2 R5 označava grupu koja je preko atoma ugljenika vezana za L, odabranu iz grupe koju čine, R -piperidinil, R R -piperazinil, R -pirolidinil, R -piperazinilkarboml, R -trope-nil, R8-morfolinil i R8-azacikloheptil grupa, a R8, R9 označavaju nesupstituisane azotne supstituente na R5, iste ili različite, vodonik ili ostatak odabran iz grupe koju čine C1-C6-alkil, -C1 -C4-alkil-C3-C10-cikloalkil, C3-C10-cikloalkil, C6-C14-aril, -C1 -C4-alkil-C6-C14-aril, piranil, piridinil, pirimidinil, C1 -C4-alkiloksikarbonil, C6-C14-arilkarbonil, C1-C4-alkilkarbonil, C6-C14-arilmetiloksikarbonil, C6-C14-arilsulfo-nil, C1-C4-alkilsulfonil i C6-C14-aril-C1-C4-alkilsulfonil grupa, u datom slučaju, u obliku svojih tautomera, svojih racemata, svojih enantiomera, svojih dijastereomera i svojih smeša, kao i, u datom slučaju, svojih farmakološki prihvatljivih adicionih soli sa kiselinom.
3. Jedinjenja, prema nekom od zahteva 1 do 3, u kojima L, m, n i R3 do R9 imaju prethodno navedena značenja, a R1, R2, isti ili različiti, označavaju ostatak izabran iz grupe koju čine, vodonik, Me, Et, Pr, ili R1 i R2 zajedno obrazuju C2-C4-alkil most, u datom slučaju, svojih tautomera, svojih racemata, svojih enantiomera, svojih dijastereomera, i svojih smeša, kao i, u datom slučaju, svojih farmakološki prihvatljivih adicionih soli sa kiselinom.
4.Jedinjenja, prema nekom od zahteva 1 do 4, u kojima R1, R2, m, n i R5 do R8, imaju prethodno navedena značenja, a R3 označava ostatak izabran iz grupe koju čine, u datom slučaju, supstituisana C1-C10-alkil, C3-C7-cikloalkil, C3-C6-heterocikloalkil i C6-C14-aril grupa, ili R1 i R3, ili R2 i R3, zajedno označavaju zasićen ili nezasićen C3-C4-alkil most, koji može da sadrži 1 do 2 heteroatoma, R4 označava ostatak izabran iz grupe koju čine, vodonik, OMe, OH, Me, Et, Pr, OEt, NHMe, NH2, F, Cl, Br, O-propargil, O-butinil, CN, SMe, NMe2, CONH2, etinil, propinil, butinil i alil grupa, a L označava veznu grupu odabranu iz grupe koju čine, u datom slučaju, supstituisana fenil, fenilmetil, cikloheksil i razgranata C1-C6-alkil grupa, u datom slučaju, u obliku svojih tautomera, svojih racemata, svojih enantiomera, svojih dijastereomera i svojih smeša, kao i, u datom slučaju, svojih farmakološki prihvatljivih adicionih soli sa kiselinom.
5. Jedinjenja, prema nekom od zahteva 1 do 4, u kojima R1, R2, m, n i R5 do R8, imaju prethodno navedena značenja, a R3 označava ostatak izabran iz grupe koju čine, u datom slučaju, supstituisana C1-C10-alkil, C3-C7-cikloalkil, C3-C6-heterocikloalkil i C6-C14-aril grupa, ili R1 i R3, ili R2 i R3, zajedno označavaju zasićen ili nezasićen C3-C4-alkil most, koji može da sadrži 1 do 2 heteroatoma, R4 označava ostatak izabran iz grupe koju čine, vodonik, OMe, OH, Me, Et, Pr, OEt, NHMe, NH2, F, Cl, Br, O-propargil, O-butinil, CN, SMe, NMe2, CONH2, etinil, propinil, butinil i alil grupa, a L označava veznu grupu odabranu iz grupe koju čine, u datom slučaju, supstituisana fenil, fenilmetil, cikloheksil i razgranata C1-C6-alkil grupa, u datom slučaju, u obliku svojih tautomera, svojih racemata, svojih enantiomera, svojih dijastereomera i svojih smeša, kao i, u datom slučaju, svojih farmakološki prihvatljivih adicionih soli sa kiselinom.
6. Jedinjenje formule I, prema nekom od zahteva 1 do 5, koje se koristi kao lek.
7. Jedinjenje formule I, prema nekom od zahteva 1 do 5, koje se koristi kao lek sa antiproliferativnim dejstvom.
8. Upotreba jedinjenja formule I, prema nekom od zahteva 1 do 5, za pripremanje leka za lečenje i/ili prevenciju raka, infekcija, zapaljenskih i autoimunskih oboljenja.
9. Postupak za lečenje i/ili prevenciju, raka, infekcija, zapaljenskih i autoimunskih oboljenja, naznačen time, što se pacijentu daje efikasna količina jedinjenja formule I, prema zahtevu 1 do 4.
10. Farmaceutski preparat, koji sadrži kao delotvornu supstancu jedno ili više jedinjenja, opšte formule (I), prema nekom od zahteva 1 do 4, ili njihovih farmakološki podnošljivih soli, u datom slučaju, sa uobičajenim pomoćnim sredstvima i/ili nosačima.
11. Postupak za pripremanje jedinjenja opšte formule (I), u kojoj R1-R5, m, n i L imaju značenje navedeno u zahtevima 1 do 5, naznačen time, što jedinjenje opšte formule (II) u kojoj R1-R3 imaju značenje navedeno u zahtevima 1 do 4, a A je grupa koja se odvaja, reaguje sa, u datom slučaju, supstituisanim jedinjenjem opšte formule (III), u kojoj R4 ima značenje navedeno u zahtevima 1 do 5, a R10 označava, OH, NH-L-R5, -O-metil, -O-etil grupu, pa zatim, u datom slučaju, proizvod opšte formule (IV) u kojoj R1 do R4 imaju značenje navedeno u zahtevima 1 do 5, a R10 označava OH, -NH-L-R5, -O-metil ili -O-etil grupu, u datom slučaju, posle prethodne hidrolize estarske grupe -COR10, reaguje sa nekim aminom, opšte formule (V) NH2-L-R5m (V) u kojoj R5 ima značenje navedeno u zahtevima 1 do 5.
12. Jedinjenje formule (II) u kojoj R1-R3 imaju značenje navedeno u zahtevima 1 do 5, a A je grupa koja se odvaja.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP2003/001935 WO2004076454A1 (de) | 2003-02-26 | 2003-02-26 | Dihydropteridinone, verfahren zu deren herstellung und deren verwendung als arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MEP58808A MEP58808A (en) | 2011-05-10 |
| ME00376B true ME00376B (me) | 2011-10-10 |
Family
ID=32921552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MEP-2008-588A ME00376B (me) | 2003-02-26 | 2003-02-26 | DIHIDROPTERIDINONI, POSTUPAK ZA NJlHOVO PRIPREMANJE I NJlHOVA PRIMJENA KAO LIJEK |
Country Status (26)
| Country | Link |
|---|---|
| EP (1) | EP1599478B1 (me) |
| JP (1) | JP3876265B2 (me) |
| KR (1) | KR100983462B1 (me) |
| CN (2) | CN101200457A (me) |
| AT (1) | ATE361924T1 (me) |
| AU (1) | AU2003215591B2 (me) |
| BR (1) | BR0318145A (me) |
| CA (1) | CA2517020C (me) |
| CY (1) | CY1106752T1 (me) |
| DE (1) | DE50307267D1 (me) |
| DK (1) | DK1599478T3 (me) |
| EA (1) | EA008778B1 (me) |
| ES (1) | ES2287583T3 (me) |
| HR (1) | HRP20050735B1 (me) |
| IL (1) | IL170419A (me) |
| ME (1) | ME00376B (me) |
| MX (1) | MXPA05009068A (me) |
| NO (1) | NO332538B1 (me) |
| NZ (1) | NZ542498A (me) |
| PL (1) | PL226417B1 (me) |
| PT (1) | PT1599478E (me) |
| RS (1) | RS52386B (me) |
| SI (1) | SI1599478T1 (me) |
| TW (1) | TWI313600B (me) |
| UA (1) | UA80743C2 (me) |
| WO (1) | WO2004076454A1 (me) |
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- 2003-02-26 KR KR1020057015805A patent/KR100983462B1/ko not_active Expired - Fee Related
- 2003-02-26 HR HRP20050735AA patent/HRP20050735B1/hr not_active IP Right Cessation
- 2003-02-26 ME MEP-2008-588A patent/ME00376B/me unknown
- 2003-03-03 TW TW092104404A patent/TWI313600B/zh not_active IP Right Cessation
-
2005
- 2005-08-22 IL IL170419A patent/IL170419A/en not_active IP Right Cessation
- 2005-09-23 NO NO20054414A patent/NO332538B1/no not_active IP Right Cessation
-
2007
- 2007-07-24 CY CY20071100981T patent/CY1106752T1/el unknown
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