HRP20150576T1 - Postupak za pripremu supstituiranih derivata pirimidina - Google Patents
Postupak za pripremu supstituiranih derivata pirimidina Download PDFInfo
- Publication number
- 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
- Authority
- HR
- Croatia
- Prior art keywords
- formula
- compound
- group
- image
- alkyl
- Prior art date
Links
- 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
Landscapes
- 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)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (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 |
|---|---|---|---|---|
| ES2348829T3 (es) | 2006-03-31 | 2010-12-15 | Janssen Pharmaceutica Nv | Benzimidazol-2-il-pirimidinas y pirazinas moduladoras del receptor h4 de histamina. |
| US9371311B2 (en) | 2008-06-30 | 2016-06-21 | Janssen Pharmaceutica Nv | Benzoimidazol-2-yl pyrimidine derivatives |
| NZ590170A (en) | 2008-06-30 | 2012-04-27 | Janssen Pharmaceutica Nv | Process for the preparation of substituted pyrimidine derivatives |
| JP5574294B2 (ja) * | 2010-11-04 | 2014-08-20 | 独立行政法人科学技術振興機構 | 光磁気記録媒体及び光磁気記録方法 |
| EA201591648A1 (ru) | 2013-03-06 | 2016-02-29 | Янссен Фармацевтика Нв | Бензимидазол-2-ил-пиримидиновые модуляторы рецептора гистамина h4 |
| SG11201608114QA (en) * | 2014-03-28 | 2016-11-29 | Kaneka Corp | Method for producing tri-carbobenzoxy-arginine |
| SG11201903871TA (en) | 2016-11-03 | 2019-05-30 | Bristol Myers Squibb Co | Substituted bicycle heterocyclic derivatives useful as romk channel inhibitors |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3005852A (en) | 1959-12-22 | 1961-10-24 | Gen Aniline & Film Corp | Production of sulfoxides and sulfones |
| US3931195A (en) * | 1971-03-03 | 1976-01-06 | Mead Johnson & Company | Substituted piperidines |
| US4191828A (en) * | 1976-04-14 | 1980-03-04 | Richardson-Merrell Inc. | Process for preparing 2-(2,2-dicyclohexylethyl)piperidine |
| US4190601A (en) * | 1978-05-31 | 1980-02-26 | Union Carbide Corporation | Production of tertiary amines by reductive alkylation |
| JPS5942396A (ja) * | 1982-09-02 | 1984-03-08 | Ishihara Sangyo Kaisha Ltd | リン酸アミド誘導体およびそれらを含有する殺虫、殺ダニ、殺線虫剤 |
| JPS6130576A (ja) | 1984-07-24 | 1986-02-12 | Ube Ind Ltd | ２−アミノ−５−シアノピリミジンの製法 |
| CA2144762A1 (en) * | 1992-10-14 | 1994-04-28 | George D. Hartman | Fibrinogen receptor antagonists |
| GB9422391D0 (en) | 1994-11-05 | 1995-01-04 | Solvay Interox Ltd | Oxidation of organosulphur compounds |
| CA2321153A1 (en) | 1998-02-17 | 1999-08-19 | Timothy D. Cushing | Anti-viral pyrimidine derivatives |
| GB9914258D0 (en) * | 1999-06-18 | 1999-08-18 | Celltech Therapeutics Ltd | Chemical compounds |
| CA2379585C (en) * | 1999-09-30 | 2006-06-20 | James W. Darrow | Certain alkylene diamine-substituted pyrazolo[1,5,-a]-1,5-pyrimidines and pyrazolo[1,5-a]-1,3,5-triazines |
| BR0112712A (pt) | 2000-07-21 | 2003-05-20 | Syngenta Partcipations Ag | Processo para preparação de 4,6-dimetóxi-2-(metilsulfonil)-1,3-pirimidina |
| PE20020506A1 (es) * | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
| US20030130264A1 (en) | 2001-02-16 | 2003-07-10 | Tularik Inc. | Methods of using pyrimidine-based antiviral agents |
| EP1372642A1 (en) * | 2001-03-30 | 2004-01-02 | SmithKline Beecham Corporation | Use of pyrazolopyridines as therapeutic compounds |
| DE60210819T2 (de) * | 2001-12-17 | 2007-04-19 | Smithkline Beecham Corp. | Pyrazolopyridazinderivate |
| TWI270542B (en) | 2002-02-07 | 2007-01-11 | Sumitomo Chemical Co | Method for preparing sulfone or sulfoxide compound |
| JP2006509014A (ja) * | 2002-12-04 | 2006-03-16 | ジーン ロジック インコーポレイテッド | メラノコルチンレセプターの調節因子 |
| RU2328497C2 (ru) | 2003-05-05 | 2008-07-10 | Ф.Хоффманн-Ля Рош Аг | Конденсированные производные пиримидина и лекарственное средство, обладающее активностью в отношении crf |
| KR20070083828A (ko) | 2004-10-27 | 2007-08-24 | 쉐링 코포레이션 | Ｎａｖ１．８의 짧은 간섭 핵산 억제를 위한 조성물 및방법 |
| EP1890703B1 (en) | 2005-06-14 | 2016-05-11 | Taigen Biotechnology | Pyrimidine compounds as chemokine receptors inhibitors |
| AU2006266529B2 (en) * | 2005-07-06 | 2010-12-16 | Cytiva Bioprocess R&D Ab | Method of preparing a separation matrix |
| TW200800201A (en) * | 2005-11-18 | 2008-01-01 | Lilly Co Eli | Pyrimidinyl benzothiophene compounds |
| CN101032483B (zh) * | 2006-03-09 | 2011-05-04 | 陈德桂 | 调节雄激素受体活性的乙内酰脲衍生物及其应用 |
| ES2348829T3 (es) * | 2006-03-31 | 2010-12-15 | Janssen Pharmaceutica Nv | Benzimidazol-2-il-pirimidinas y pirazinas moduladoras del receptor h4 de histamina. |
| ATE479678T1 (de) * | 2006-03-31 | 2010-09-15 | Janssen Pharmaceutica Nv | Benzoimidazol-2-yl pyridine als modulatoren des histamin-h4-rezeptors |
| KR20110022721A (ko) * | 2008-06-30 | 2011-03-07 | 얀센 파마슈티카 엔.브이. | 벤조이미다졸-2-일 피리미딘 유도체의 제조 방법 |
| NZ590170A (en) | 2008-06-30 | 2012-04-27 | Janssen Pharmaceutica Nv | Process for the preparation of substituted pyrimidine derivatives |
-
2009
- 2009-06-29 NZ NZ590170A patent/NZ590170A/en not_active IP Right Cessation
- 2009-06-29 EP EP15157463.9A patent/EP2924025A1/en not_active Withdrawn
- 2009-06-29 JO JOP/2009/0240A patent/JO3043B1/ar active
- 2009-06-29 JP JP2011516757A patent/JP5416768B2/ja not_active Expired - Fee Related
- 2009-06-29 EP EP15157453.0A patent/EP2924023A1/en not_active Withdrawn
- 2009-06-29 PL PL09774225T patent/PL2310012T3/pl unknown
- 2009-06-29 DK DK09774225T patent/DK2310012T3/da active
- 2009-06-29 HU HUE09774225A patent/HUE024949T2/en unknown
- 2009-06-29 TW TW098121755A patent/TWI498326B/zh not_active IP Right Cessation
- 2009-06-29 PT PT97742258T patent/PT2310012E/pt unknown
- 2009-06-29 CN CN200980134933.7A patent/CN102137672B/zh not_active Expired - Fee Related
- 2009-06-29 AU AU2009267156A patent/AU2009267156B2/en not_active Ceased
- 2009-06-29 SI SI200931188T patent/SI2310012T1/sl unknown
- 2009-06-29 EA EA201170113A patent/EA019361B1/ru not_active IP Right Cessation
- 2009-06-29 EP EP15157445.6A patent/EP2924035A1/en not_active Withdrawn
- 2009-06-29 RS RS20150287A patent/RS53985B1/en unknown
- 2009-06-29 AR ARP090102405 patent/AR072396A1/es not_active Application Discontinuation
- 2009-06-29 PE PE2010001216A patent/PE20110163A1/es not_active Application Discontinuation
- 2009-06-29 TW TW103118001A patent/TW201433568A/zh unknown
- 2009-06-29 ES ES09774225.8T patent/ES2538135T3/es active Active
- 2009-06-29 EP EP20140161564 patent/EP2769721A3/en not_active Withdrawn
- 2009-06-29 WO PCT/US2009/049027 patent/WO2010002774A1/en active Application Filing
- 2009-06-29 BR BRPI0913644A patent/BRPI0913644A2/pt not_active Application Discontinuation
- 2009-06-29 KR KR1020117001991A patent/KR101675354B1/ko active IP Right Grant
- 2009-06-29 MY MYPI2010006258A patent/MY150601A/en unknown
- 2009-06-29 US US12/459,229 patent/US8309720B2/en active Active
- 2009-06-29 TW TW103104509A patent/TWI481603B/zh not_active IP Right Cessation
- 2009-06-29 UA UAA201100983A patent/UA106724C2/uk unknown
- 2009-06-29 EP EP20090774225 patent/EP2310012B1/en active Active
- 2009-06-29 MX MX2011000080A patent/MX2011000080A/es active IP Right Grant
- 2009-06-29 CA CA2729733A patent/CA2729733C/en not_active Expired - Fee Related
- 2009-06-29 ME MEP-2015-79A patent/ME02154B/me unknown
- 2009-06-30 UY UY31949A patent/UY31949A/es unknown
-
2010
- 2010-12-23 NI NI201000232A patent/NI201000232A/es unknown
- 2010-12-23 IL IL210214A patent/IL210214A/en active IP Right Grant
-
2011
- 2011-01-03 SV SV2011003788A patent/SV2011003788A/es unknown
- 2011-01-04 CO CO11000461A patent/CO6341560A2/es not_active Application Discontinuation
- 2011-01-05 EC ECSP11010745 patent/ECSP11010745A/es unknown
- 2011-01-28 ZA ZA2011/00759A patent/ZA201100759B/en unknown
- 2011-10-19 HK HK11111216.2A patent/HK1156857A1/xx not_active IP Right Cessation
-
2012
- 2012-10-29 US US13/663,233 patent/US9079882B2/en not_active Expired - Fee Related
-
2013
- 2013-03-15 US US13/844,227 patent/US9079883B2/en not_active Expired - Fee Related
- 2013-11-11 US US14/076,955 patent/US9079884B2/en not_active Expired - Fee Related
- 2013-11-12 US US14/078,153 patent/US9006432B2/en not_active Expired - Fee Related
- 2013-11-13 US US14/079,358 patent/US9359327B2/en not_active Expired - Fee Related
-
2014
- 2014-11-09 IL IL235571A patent/IL235571A/en active IP Right Grant
- 2014-11-09 IL IL235572A patent/IL235572A/en active IP Right Grant
- 2014-11-09 IL IL235570A patent/IL235570A/en active IP Right Grant
-
2015
- 2015-02-26 HK HK15101911.7A patent/HK1201441A1/xx unknown
- 2015-03-23 CY CY20151100293T patent/CY1116134T1/el unknown
- 2015-05-29 HR HRP20150576TT patent/HRP20150576T1/hr unknown
-
2016
- 2016-03-03 HK HK16102449.5A patent/HK1214590A1/zh unknown
- 2016-03-23 HK HK16103405.5A patent/HK1215434A1/zh unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HRP20150576T1 (hr) | Postupak za pripremu supstituiranih derivata pirimidina | |
| JP5604424B2 (ja) | アポトーシス促進剤ａｂｔ−２６３の調製のための方法 | |
| CA2861150C (en) | Morphinan derivative | |
| US6506738B1 (en) | Benzimidazolone antiviral agents | |
| KR101914606B1 (ko) | 호흡기 세포융합 바이러스 항바이러스제로서의 인돌 | |
| CN104903313B (zh) | Rsv抗病毒化合物 | |
| HRP20171914T1 (hr) | Postupak za dobivanje spojeva koji su korisni kao inhibitori sglt | |
| AU2018204086A1 (en) | Processes and intermediates for preparing a medicament | |
| AU2018200461B2 (en) | Process methods for phosphatidylinositol 3-kinase inhibitors | |
| AU2004298460B2 (en) | Morpholinyl containing benzimidazoles as inhibitors of respiratory syncytial virus replication | |
| HRP20170621T1 (hr) | Postupak za pripremanje derivata piperazinil i diazepanil benzamida | |
| CN107108519A (zh) | 制备ask1抑制剂的方法 | |
| PL174909B1 (pl) | Podstawione 4-azacykliczne pochodne fenylo-5-amidometylo-oksazolidynonu | |
| JP2021536468A (ja) | メチル６−（２，４−ジクロロフェニル）−５−［４−［（３ｓ）−１−（３−フルオロプロピル）ピロリジン−３−イル］オキシフェニル］−８，９−ジヒドロ−７ｈ−ベンゾ［７］アヌレン−２−カルボキシレートの調製方法 | |
| HRP20100420T1 (hr) | Postupak za pripravu nebivolola | |
| EP0788498A1 (en) | Phenyloxazolidinone antimicrobials | |
| MXPA06009132A (es) | Inhibidores de integrasa de vih. | |
| HRP20121068T1 (hr) | Inhibitori ciklopropil polimeraze | |
| TW200922937A (en) | Process for the synthesis of E1 activating enzyme inhibitors | |
| CA2824519C (en) | Process of making gyrase and topoisomerase inhibitors | |
| JP2023022230A (ja) | Ｅｈｍｔ２阻害剤としての置換された融合二環式または三環式複素環化合物 | |
| CN114514233A (zh) | 用于单酰基甘油脂肪酶(magl)的荧光探针 | |
| JP7218005B2 (ja) | 新規な４－ベンゾアゾニン誘導体の製造方法 | |
| RU2410382C2 (ru) | 1, 3-дигидробензимидазол-2-илиденовые амины в качестве ингибиторов репликации респираторного синцитиального вируса | |
| CN101646659A (zh) | 坎地沙坦西酯的制备方法及其中间体 |