HRP20150576T1 - Postupak za pripremu supstituiranih derivata pirimidina - Google Patents
Postupak za pripremu supstituiranih derivata pirimidina Download PDFInfo
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- HRP20150576T1 HRP20150576T1 HRP20150576TT HRP20150576T HRP20150576T1 HR P20150576 T1 HRP20150576 T1 HR P20150576T1 HR P20150576T T HRP20150576T T HR P20150576TT HR P20150576 T HRP20150576 T HR P20150576T HR P20150576 T1 HRP20150576 T1 HR P20150576T1
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- alkyl
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- 238000000034 method Methods 0.000 title claims 29
- 238000002360 preparation method Methods 0.000 title claims 5
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title 1
- 150000003230 pyrimidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 57
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000003960 organic solvent Substances 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 239000007822 coupling agent Substances 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 238000010511 deprotection reaction Methods 0.000 claims 4
- -1 ethyl propyl Chemical group 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 claims 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
- C07D401/02—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
-
- 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
- A61K31/495—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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/20—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
- C07C211/22—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton containing at least two amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Claims (30)
1. Postupak za pripremu spoja formule (I)
[image]
pri čemu
L1 je CN;
Rc je izabran iz grupe koja se sastoji od H, metila, etila propila, izopropila, -CF3, ciklopropila, i ciklobutila;
R6 je vodik;
R8 je izabran iz grupe koja se sastoji od vodika i C1-4alkila;
Z je izabran iz grupe koja se sastoji od N i CH;
n je 1 ili 2;
R9, R10 i R11 su svaki nezavisno izabrani iz grupe koja se sastoji od vodika i C1-4alkila;
i njihovih farmaceutski prihvatljivih soli; sadržavajući
[image]
reagiranje spoja formule (V) pri čemu PG1 i PG2 su svaki nezavisno dušikova zaštitna grupa, sa spojem formule (VI), pri čemu je LG1 odlazeća grupa, u prvom organskom otapalu; i kada LG1 je OH, u prisustvu sustava sredstva za spajanje; da se dobije odgovarajući spoj formule (VII);
[image]
uklanjanje zaštite spoja formule (VII), da se dobije odgovarajući spoj formule (VIII); i
[image]
reagiranje spoja formule (VIII) sa spojem formule (IX), u drugom organskom otapalu, da se dobije odgovarajući spoj formule (I), pri čemu je X izabran iz grupe koja se sastoji od -N(R20)2, i -OR21; pri čemu je svaki R20 nezavisno izabran iz grupe koja se sastoji od C1-4alkila; alternativno dvije R20 grupe su uzete zajedno sa atomom dušika na koji su vezane da formiraju zasićenu prstenastu strukturu izabranu iz grupe koja se sastoji od piperidinila, pirolidinila i morfolinila; i pri čemu R21 je izabran od grupe koja se sastoji od C1-4alkila i benzila.
2. Postupak za pripremu spoja formule (I-S)
[image]
koji sadrži
[image]
reagiranje spoja formule (V) pri čemu PG1 i PG2 su svaki nezavisno dušikna zaštitna grupa, sa spojem formule (VI-S), pri čemu LG1 je odlazeća grupa, u prvom organskom otapalu; i kada LG1 je OH, u prisustvu sustava sredstva za spajanje; da se dobije odgovarajuće spoje formule (VII-S);
[image]
uklanjanje zaštite spoja formule (VII-S ), da se dobije odgovarajuće spoje formule (VIII-S ); i
[image]
reagiranje spoja formule (VIII-S) sa spojem formule (IX-S), u drugom organskom otapalu, da se dobije odgovarajući spoj formule (I-S), pri čemu je X izabran iz grupe koja se sastoji od -N(R20)2, i -OR21; pri čemu je svaki R20 nezavisno izabran iz grupe koja se sastoji od C1-4alkila; alternativno dvije R20 grupe su uzete zajedno sa atomom dušika na koji su vezane da formiraju zasićenu prstenastu strukturu izabranu iz grupe koja se sastoji od piperidinila, pirolidinila i morfolinila; i pri čemu je R21 izabran iz grupe koja se sastoji od C1-4alkila i benzila.
3. Postupak kao u Zahtjevu 2, pri čemu su PG1 i PG2 svaki CBz.
4. Postupak kao u Zahtjevu 2, pri čemu spoj formule (VI-S) LG1 je hidroksi.
5. Postupak kao u Zahtjevu 2, pri čemu je spoj formule (VI-S) prisutan u količini od oko 1.0 molarna ekvivalenta.
6. Postupak kao u Zahtjevu 2, pri čemu je sustav sredstva za spajanje DIAD i PPh3; i pri čemu je sustav sredstva za spajanje prisutan u količini od oko 1.2 molarna ekvivalenta.
7. Postupak kao u Zahtjevu 2, pri čemu je prvo organsko otapalo 2-metil-THF.
8. Postupak kao u Zahtjevu 2, pri čemu spoj formule (V-S) reagira sa spojem formule (VI-S) pri oko 5°C.
9. Postupak kao u Zahtjevu 2, pri čemu se spoju formule (VII-S) uklanja zaštitna grupa reagiranjem spoja formule (VII-S) sa plinovitim vodikom u prisustvu Pd/C katalizatora.
10. Postupak kao u Zahtjevu 2, pri čemu spoj formule (IX-S), X je -N(CH3)2
11. Postupak kao u Zahtjevu 2, pri čemu spoj formule (IX-S) je prisutan u količini od oko 1.5 molarna ekvivalenta.
12. Postupak kao u Zahtjevu 2, pri čemu je drugo organsko otapalo etanol.
13. Postupak kao u Zahtjevu 2, pri čemu spoj formule (VIII-S) reagira sa spojem formule (IX-S) pri otprilike temperaturi refluksa.
14. Spoj pripremljen prema postupku kao u Zahtjevu 2.
15. Postupak za pripremu spoja formule (I)
[image]
pri čemu
L1 is CN;
Rc je izabran iz grupe koja se sastoji od H, metila, etila, propila, izopropila, -CF3, ciklopropila, i ciklobutila;
R6 je vodik;
R8 je izabran iz grupe koja se sastoji od vodika i C1-4alkila;
Z je izabran iz grupe koja se sastoji od N i CH;
n je 1 ili 2;
R9, R10 i R11 su svaki nezavisno izabrani iz grupe koja se sastoji od vodika i C1-4alkila;
i njihove farmaceutski prihvatljive soli; sadržavajući
[image]
reagiranje spoja formule (IX) pri čemu je X izabran iz grupe koja se sastoji od -N(R20)2, i -OR21; pri čemu je svaki R20 nezavisno izabran iz grupe koja se sastoji od C1-4alkila; alternativno dvije R20 grupe su uzete zajedno sa atomom dušika na koji su vezane da formiraju zasićenu prstenastu strukturu izabranu iz grupe koja se sastoji od piperidinila, pirolidinila i morfolinila; i pri čemu je R21 izabran iz grupe koja se sastoji od C1-4alkila i benzila; sa spojem formule (X), pri čemu je PG3 dušikova zaštitna grupa, u prvom organskom otapalu, da se dobije odgovarajući spoj formule (XI);
[image]
reagiranje spoja formule (XI) sa spojem formule (VIA), u prisustvu sustava sredstva za spajanje, u drugom organskom otapalu, da se dobije odgovarajući spoj formule (XII); i
[image]
uklanjanje zaštite spoja formule (XII), da se dobije odgovarajući spoj formule (I).
16. Postupak za pripremu spoja formule (I-S)
[image]
koji sadrži
[image]
reagiranje spoja formule (IX-S) pri čemu je X izabran iz grupe koja se sastoji od -N(R20)2, i -OR21; pri čemu je svaki R20 nezavisno izabran iz grupe koja se sastoji od C1-4alkila; alternativno dvije R20 grupe su uzete zajedno sa atomom dušika na koji su vezane da formiraju zasićenu prstenastu strukturu izabranu iz grupe koja se sastoji od piperidinila, pirolidinila i morfolinila; i pri čemu je R21 izabran iz grupe koja se sastoji od C1-4alkila i benzila; sa spojem formule (X), pri čemu je PG3 dušikova zaštitna grupa, u prvom organskom otapalu, da se dobije odgovarajući spoj formule (XI-S);
[image]
reagiranje spoja formule (XI-S) sa spojem formule (VI-B), u prisustvu sustava sredstva za spajanje, u drugom organskom otapalu, da se dobije odgovarajući spoj formule (XII-S); i
[image]
uklanjanje zaštite spoja formule (XII-S), da se dobije odgovarajući spoj formule (I-S).
17. Postupak kao u Zahtjevu 16, pri čemu je PG3 izabran iz grupe koja se sastoji od -C(O)CH3, -C(O)OCH2CH3, -C(O)O-t-butil, -CHO, -C(O)OCH3, -C(O)O-CH2-fenil, -C(O)-fenil, -C(O)OCH2CCl3, -C(O)-(4-nitrofenil),-C(O)CCl3, -C(O)CF3, -SO2CH3, -SO2-fenil, -SO2-(4-nitrofenil) i – SO2CF3.
18. Postupak kao u Zahtjevu 16, pri čemu je PG3 izabran iz grupe koja se sastoji od -C(O)CH3, -C(O)OCH2CH3 i -C(O)O-t-butila.
19. Postupak kao u Zahtjevu 16, pri čemu je PG3 izabran iz grupe koja se sastoji od -C(O)OCH2CH3 i -C(O)O-t-butila.
20. Postupak kao u Zahtjevu 16, pri čemu spoj formule (IX-S), X je -N(CH3)2.
21. Postupak kao u Zahtjevu 16, pri čemu spoj formule (IX-S) je prisutan u količini od oko 1.5 molarna ekvivalenta.
22. Postupak kao u Zahtjevu 16, pri čemu je prvo organsko otapalo 2-metil-THF.
23. Postupak kao u Zahtjevu 16, pri čemu spoj formule (IX-S) reagira sa spojem formule (X) pri oko 80°C.
24. Postupak kao u Zahtjevu 16, pri čemu je spoj formule (VI-B) prisutno u količini od oko 1.5 molarna ekvivalenta.
25. Postupak kao u Zahtjevu 16, pri čemu je sustav sredstva za spajanje DIAD i PPh3; i pri čemu je sustav sredstva za spajanje prisutan u količini od oko 1.2 molarna ekvivalenta.
26. Postupak kao u Zahtjevu 16, pri čemu je drugo organsko otapalo 2-metil-THF.
27. Postupak kao u Zahtjevu 16, pri čemu spoje formule (XI-S) reagira sa spojem formule (VI-B)
na temperaturi pri oko 5°C.
28. Spoj pripremljen prema postupku iz Zahtjeva 16.
29. Spoj formule (I)
[image]
pri čemu
L1 je CN;
Rc je izabran iz grupe koja se sastoji od H, metila, etila, propila, izopropila, -CF3, ciklopropila, i ciklobutila;
R6 je vodik;
R8 je izabran iz grupe koja se sastoji od vodika i C1-4alkila;
Z je izabran iz grupe koja se sastoji od N i CH;
n je 1 ili 2;
R9, R10 i R11 su svaki nezavisno izabrani iz grupe koja se sastoji od vodika i C1-4alkila;
ili njihove farmaceutski prihvatljive soli.
30. Spoj formule (I-S)
[image]
ili njegove farmaceutski prihvatljive soli.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7675208P | 2008-06-30 | 2008-06-30 | |
| PCT/US2009/049027 WO2010002774A1 (en) | 2008-06-30 | 2009-06-29 | Process for the preparation of substituted pyrimidine derivatives |
| EP20090774225 EP2310012B1 (en) | 2008-06-30 | 2009-06-29 | Process for the preparation of substituted pyrimidine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20150576T1 true HRP20150576T1 (hr) | 2015-09-11 |
Family
ID=41464882
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20150576TT HRP20150576T1 (hr) | 2008-06-30 | 2015-05-29 | Postupak za pripremu supstituiranih derivata pirimidina |
Country Status (36)
| Country | Link |
|---|---|
| US (6) | US8309720B2 (hr) |
| EP (5) | EP2924025A1 (hr) |
| JP (1) | JP5416768B2 (hr) |
| KR (1) | KR101675354B1 (hr) |
| CN (1) | CN102137672B (hr) |
| AR (1) | AR072396A1 (hr) |
| AU (1) | AU2009267156B2 (hr) |
| BR (1) | BRPI0913644A2 (hr) |
| CA (1) | CA2729733C (hr) |
| CO (1) | CO6341560A2 (hr) |
| CY (1) | CY1116134T1 (hr) |
| DK (1) | DK2310012T3 (hr) |
| EA (1) | EA019361B1 (hr) |
| EC (1) | ECSP11010745A (hr) |
| ES (1) | ES2538135T3 (hr) |
| HK (4) | HK1156857A1 (hr) |
| HR (1) | HRP20150576T1 (hr) |
| HU (1) | HUE024949T2 (hr) |
| IL (4) | IL210214A (hr) |
| JO (1) | JO3043B1 (hr) |
| ME (1) | ME02154B (hr) |
| MX (1) | MX2011000080A (hr) |
| MY (1) | MY150601A (hr) |
| NI (1) | NI201000232A (hr) |
| NZ (1) | NZ590170A (hr) |
| PE (1) | PE20110163A1 (hr) |
| PL (1) | PL2310012T3 (hr) |
| PT (1) | PT2310012E (hr) |
| RS (1) | RS53985B1 (hr) |
| SI (1) | SI2310012T1 (hr) |
| SV (1) | SV2011003788A (hr) |
| TW (3) | TWI498326B (hr) |
| UA (1) | UA106724C2 (hr) |
| UY (1) | UY31949A (hr) |
| WO (1) | WO2010002774A1 (hr) |
| ZA (1) | ZA201100759B (hr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101054325B1 (ko) | 2006-03-31 | 2011-08-04 | 얀센 파마슈티카 엔.브이. | 히스타민 ｈ４ 수용체 조절제로서의 벤조이미다졸―２―일 피리미딘 및 피라진 |
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