HRP20110047T1 - Novi derivati 5-supstituiranog 7-amino-[1,3]tiazolo[4,5-d]pirimidina - Google Patents
Novi derivati 5-supstituiranog 7-amino-[1,3]tiazolo[4,5-d]pirimidina Download PDFInfo
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- HRP20110047T1 HRP20110047T1 HR20110047T HRP20110047T HRP20110047T1 HR P20110047 T1 HRP20110047 T1 HR P20110047T1 HR 20110047 T HR20110047 T HR 20110047T HR P20110047 T HRP20110047 T HR P20110047T HR P20110047 T1 HRP20110047 T1 HR P20110047T1
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- -1 5-substituted 7-amino-[1,3]thiazolo[4,5-d]pyrimidine Chemical class 0.000 title 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 32
- 150000003839 salts Chemical class 0.000 claims abstract 13
- 239000003814 drug Substances 0.000 claims 6
- 229940079593 drug Drugs 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- 238000011321 prophylaxis Methods 0.000 claims 5
- 238000011282 treatment Methods 0.000 claims 5
- 201000001320 Atherosclerosis Diseases 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 238000000034 method Methods 0.000 claims 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 230000003902 lesion Effects 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
- PDKBAEAFZLXVQK-AWKYBWMHSA-N (2r)-2-[[2-amino-5-(1-phenylethylsulfanyl)-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]-methylamino]-4-methylpentan-1-ol Chemical compound N=1C=2N=C(N)SC=2C(N(C)[C@@H](CO)CC(C)C)=NC=1SC(C)C1=CC=CC=C1 PDKBAEAFZLXVQK-AWKYBWMHSA-N 0.000 claims 1
- ZMQSLMZOWVGBSM-TYZXPVIJSA-N (2r)-2-[[2-amino-5-(1-phenylethylsulfanyl)-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-methylpentan-1-ol Chemical compound N=1C=2N=C(N)SC=2C(N[C@@H](CO)CC(C)C)=NC=1SC(C)C1=CC=CC=C1 ZMQSLMZOWVGBSM-TYZXPVIJSA-N 0.000 claims 1
- SZCVFEVNVFBNBL-GICMACPYSA-N (2r)-2-[[2-amino-5-(1-phenylpropylsulfanyl)-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-methylpentan-1-ol Chemical compound N=1C(N[C@@H](CO)CC(C)C)=C2SC(N)=NC2=NC=1SC(CC)C1=CC=CC=C1 SZCVFEVNVFBNBL-GICMACPYSA-N 0.000 claims 1
- LBAMGFHXEZOCSA-WDEREUQCSA-N (2r)-2-[[2-amino-5-[(1s)-1-(2-fluorophenyl)ethyl]sulfanyl-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-fluoro-4-methylpentan-1-ol Chemical compound C1([C@@H](SC=2N=C3N=C(N)SC3=C(N[C@@H](CO)CC(C)(C)F)N=2)C)=CC=CC=C1F LBAMGFHXEZOCSA-WDEREUQCSA-N 0.000 claims 1
- PQYZCJMYDYNLKP-NWDGAFQWSA-N (2r)-2-[[2-amino-5-[(1s)-1-(2-fluorophenyl)ethyl]sulfanyl-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-methylpentan-1-ol Chemical compound C1([C@H](C)SC=2N=C(C=3SC(N)=NC=3N=2)N[C@@H](CO)CC(C)C)=CC=CC=C1F PQYZCJMYDYNLKP-NWDGAFQWSA-N 0.000 claims 1
- HNGCDCABVYTVAE-WDEREUQCSA-N (2r)-2-[[2-amino-5-[(1s)-1-(2-fluorophenyl)ethyl]sulfanyl-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]pentan-1-ol Chemical compound C1([C@H](C)SC=2N=C(C=3SC(N)=NC=3N=2)N[C@@H](CO)CCC)=CC=CC=C1F HNGCDCABVYTVAE-WDEREUQCSA-N 0.000 claims 1
- GDKZGPOPQDQWKT-SMDDNHRTSA-N (2r)-2-[[2-amino-5-[(1s)-1-(3-fluorophenyl)ethyl]sulfanyl-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-methylpentan-1-ol Chemical compound C1([C@H](C)SC=2N=C(C=3SC(N)=NC=3N=2)N[C@@H](CO)CC(C)C)=CC=CC(F)=C1 GDKZGPOPQDQWKT-SMDDNHRTSA-N 0.000 claims 1
- ZJTOCCMPRIUOGK-GXTWGEPZSA-N (2r)-2-[[2-amino-5-[(1s)-1-(3-methylsulfonylphenyl)ethyl]sulfanyl-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-methylpentan-1-ol Chemical compound C1([C@H](C)SC=2N=C(C=3SC(N)=NC=3N=2)N[C@@H](CO)CC(C)C)=CC=CC(S(C)(=O)=O)=C1 ZJTOCCMPRIUOGK-GXTWGEPZSA-N 0.000 claims 1
- SQLWCNPRGCHCDW-WCQYABFASA-N (2r)-2-[[2-amino-5-[(1s)-1-phenylethyl]sulfanyl-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-fluoro-4-methylpentan-1-ol Chemical compound C1([C@@H](SC=2N=C3N=C(N)SC3=C(N[C@@H](CO)CC(C)(C)F)N=2)C)=CC=CC=C1 SQLWCNPRGCHCDW-WCQYABFASA-N 0.000 claims 1
- ZMQSLMZOWVGBSM-GXTWGEPZSA-N (2r)-2-[[2-amino-5-[(1s)-1-phenylethyl]sulfanyl-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-methylpentan-1-ol Chemical compound C1([C@H](C)SC=2N=C(C=3SC(N)=NC=3N=2)N[C@@H](CO)CC(C)C)=CC=CC=C1 ZMQSLMZOWVGBSM-GXTWGEPZSA-N 0.000 claims 1
- OBTCRZSOJNBQII-WCQYABFASA-N (2r)-2-[[2-amino-5-[(1s)-1-phenylethyl]sulfanyl-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]pentan-1-ol Chemical compound C1([C@H](C)SC=2N=C(C=3SC(N)=NC=3N=2)N[C@@H](CO)CCC)=CC=CC=C1 OBTCRZSOJNBQII-WCQYABFASA-N 0.000 claims 1
- BVIAWIVOFOEULB-PIJUOVFKSA-N (2r)-2-[[2-amino-5-[1-(2-chlorophenyl)ethylsulfanyl]-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-methylpentan-1-ol Chemical compound N=1C=2N=C(N)SC=2C(N[C@@H](CO)CC(C)C)=NC=1SC(C)C1=CC=CC=C1Cl BVIAWIVOFOEULB-PIJUOVFKSA-N 0.000 claims 1
- ZMMDDWBVYKJHNY-TYZXPVIJSA-N (2r)-2-[[2-amino-5-[1-(3-methoxyphenyl)ethylsulfanyl]-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-methylpentan-1-ol Chemical compound COC1=CC=CC(C(C)SC=2N=C3N=C(N)SC3=C(N[C@@H](CO)CC(C)C)N=2)=C1 ZMMDDWBVYKJHNY-TYZXPVIJSA-N 0.000 claims 1
- BGLLFCTTXBNCFY-SBXXRYSUSA-N (2r)-2-[[2-amino-5-[1-[3-(trifluoromethyl)phenyl]ethylsulfanyl]-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-methylpentan-1-ol Chemical compound N=1C=2N=C(N)SC=2C(N[C@@H](CO)CC(C)C)=NC=1SC(C)C1=CC=CC(C(F)(F)F)=C1 BGLLFCTTXBNCFY-SBXXRYSUSA-N 0.000 claims 1
- PNKYTKPWPKRAKI-SMDDNHRTSA-N 3-[(1s)-1-[[2-amino-7-[[(2r)-1-hydroxypentan-2-yl]amino]-[1,3]thiazolo[4,5-d]pyrimidin-5-yl]sulfanyl]ethyl]benzonitrile Chemical compound C1([C@H](C)SC=2N=C(C=3SC(N)=NC=3N=2)N[C@@H](CO)CCC)=CC=CC(C#N)=C1 PNKYTKPWPKRAKI-SMDDNHRTSA-N 0.000 claims 1
- XQHOYGCLIKGICN-SBXXRYSUSA-N 3-[1-[[2-amino-7-[[(2r)-1-hydroxy-4-methylpentan-2-yl]amino]-[1,3]thiazolo[4,5-d]pyrimidin-5-yl]sulfanyl]ethyl]benzamide Chemical compound N=1C=2N=C(N)SC=2C(N[C@@H](CO)CC(C)C)=NC=1SC(C)C1=CC=CC(C(N)=O)=C1 XQHOYGCLIKGICN-SBXXRYSUSA-N 0.000 claims 1
- 108090000835 CX3C Chemokine Receptor 1 Proteins 0.000 claims 1
- 102100039196 CX3C chemokine receptor 1 Human genes 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 208000016192 Demyelinating disease Diseases 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 230000008485 antagonism Effects 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 230000007214 atherothrombosis Effects 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 208000030613 peripheral artery disease Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—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
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- A—HUMAN NECESSITIES
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Abstract
Spoj, naznačen time, da je prikazan formulom (I) R1 predstavlja CH3 ili CH3CH2;R2 predstavlja H, 2-F, 2-Cl, 3-F, 3-OCH3, 3-CN, 3-CF3, 3-CONH2 ili 3-SO2CH3;R3 predstavlja H ili CH3;R4 predstavlja H ili CH3; iR5 predstavlja H; ili kada R4 je CH3, R5 predstavlja H ili F; i njegove farmaceutski prihvatljive soli. Patent sadrži još 17 patentnih zahtjeva.
Claims (18)
1. Spoj, naznačen time, da je prikazan formulom (I)
[image]
R1 predstavlja CH3 ili CH3CH2;
R2 predstavlja H, 2-F, 2-Cl, 3-F, 3-OCH3, 3-CN, 3-CF3, 3-CONH2 ili 3-SO2CH3;
R3 predstavlja H ili CH3;
R4 predstavlja H ili CH3; i
R5 predstavlja H; ili kada R4 je CH3, R5 predstavlja H ili F;
i njegove farmaceutski prihvatljive soli.
2. Spoj prema zahtjevu 1, naznačen time, da R3 predstavlja H.
3. Spoj prema zahtjevu 1 ili zahtjevu 2, naznačen time, da R1 predstavlja CH3.
4. Spoj prema bilo kojem zahtjevu 1 do 3, naznačen time, da R2 predstavlja H, 2-F ili 3-CN.
5. Spoj prema bilo kojem zahtjevu 1 do 4, naznačen time, da R4 predstavlja H.
6. Spoj prema bilo kojem zahtjevu 1 do 4, naznačen time, da R4 predstavlja CH3.
7. Spoj prema zahtjevu 6, naznačen time, da R5 predstavlja F.
8. Spoj prema zahtjevu 6, naznačen time, da R5 predstavlja H.
9. Spoj prema zahtjevu 1, naznačen time, da R1 predstavlja CH3; R2 predstavlja H, 2-F ili 3-CN; R3 predstavlja H; R4 predstavlja H ili CH3; a R5 predstavlja H.
10. Spoj formule (I) prema zahtjevu 1, naznačen time, da je:
(2R)-2-[(2-amino-5-{[(1S)-1-(2-fluorofenil)etil]tio}[1,3]tiazolo[4,5-d]pirimidin-7-il)amino]pentan-1-ol;
(2R)-2-[(2-amino-5-{[(1S)-1-(2-fluorofenil)etil]tio}[1,3]tiazolo[4,5-d]pirimidin-7-il)amino]-4-metilpentan-1-ol;
(2R)-2-({2-amino-5-[(1-feniletil)tio][1,3]tiazolo[4,5-d]pirimidin-7-il}amino)-4-metilpentan-1-ol;
(2R)-2-[(2-amino-5-{[(1R)-1-feniletil]tio[1,3]tiazolo[4,5-d]pirimidin-7-il)amino]-4-metilpentan-1-ol;
3-{(1S)-1-[(2-amino-7-{[(1R)-1-(hidroksimetil)butil]amino}[1,3]tiazolo[4,5-d]pirimidin-5-il)tio]etil}benzonitril;
(2R)-2-{[2-amino-5-({(1S)-1-[3-(metilsulfonil)fenil]etil}tio)[1,3]tiazolo[4,5-d]pirimidin-7-il]amino}-4-metilpentan-1-ol;
(2R)-2-[(2-amino-5-{[(1S)-1-feniletil]tio}[1,3]tiazolo[4,5-d]pirimidin-7-il)amino]pentan-1-ol;
3-{(1S)-1-[(2-amino-7-{[(1R)-1-(hidroksimetil)-3-metilbutil]amino[1,3]tiazolo[4,5-d]pirimidin-5-il)tio]etil}benzonitril;
(2R)-2-({2-amino-5-[(1-fenilpropil)tio][1,3]tiazolo[4,5-d]pirimidin-7-il}amino)-4-metilpentan-1-ol;
3-{1-[(2-amino-7-{[(1R)-1-(hidroksimetil)-3-metilbutil]amino}[1,3]tiazolo[4,5-d]pirimidin-5-il)tio]etil}benzamid;
(2R)-2-{[2-amino-5-({1-[3-(trifluorometil)fenil]etil}tio)[1,3]tiazolo[4,5-d]pirimidin-7-il]amino}-4-metilpentan-1-ol;
(2R)-2-[{2-amino-5-[(1-feniletil)tio][1,3]tiazolo[4,5-d]pirimidin-7-il}(metil)amino]-4-metilpentan-1-ol;
(2R)-2-[(2-amino-5-{[1-(2-hlorofenil)etil]tio}[1,3]tiazolo[4,5-d]pirimidin-7-il)amino]-4-metilpentan-1-ol;
(2R)-2-[(2-amino-5-{[1-(3-metoksifenil)etil]tio}[1,3]tiazolo[4,5-d]pirimidin-7-il)amino]-4-metilpentan-1-ol;
(2R)-2-[(2-amino-5-{[(1S)-1-feniletil]tio}[1,3]tiazolo[4,5-d]pirimidin-7-il)amino]-4-metilpentan-1-ol;
(2R)-2-[(2-amino-5-{[(1S)-1-feniletil]tio}[1,3]tiazolo[4,5-d]pirimidin-7-il)amino]-4-fluoro-4-metilpentan-1-ol;
(2R)-2-[(2-amino-5-{[(1S)-1-(2-fluorofenil)etil]tio}[1,3]tiazolo[4,5-d]pirimidin-7-il)amino]-4-fluoro-4-metilpentan-1-ol;
(2R)-2-[(2-amino-5-{[(1S)-1-(3-fluorofenil)etil]tio}[1,3]tiazolo[4,5-d]pirimidin-7-il)amino]-4-metilpentan-1-ol;
ili njegova farmaceutski prihvatljiva sol.
11. Spoj formule (I), prema bilo kojem zahtjevu 1 do 10, ili njegova farmaceutski prihvatljiva sol, naznačen time, da se upotrebljava kao lijek.
12. Farmaceutska formulacija, naznačena time, da sadrži spoj formule (I), kako je definirano u bilo kojem zahtjevu 1 do 10, ili njegovu farmaceutski prihvatljivu sol u smjesi sa farmaceutski prihvatljivim otapalom ili nosačem.
13. Upotreba spoja formule (I) kako je definirano u bilo kojem zahtjevu 1 do 10, ili njegove farmaceutski prihvatljive soli, naznačena time, da se navedeni spoj upotrebljava kod proizvodnje lijeka za liječenje ili profilaksu humanih bolesti ili stanja u kojima se koristi antagonizam CX3CR1 receptora.
14. Upotreba spoja formule (I) kako je definirano u bilo kojem zahtjevu 1 do 10, ili njegove farmaceutski prihvatljive soli, naznačena time, da se navedeni spoj upotrebljava za proizvodnju lijeka za liječenje ili profilaksu neurodegenerativnih poremećaja, bolesti demijelinacije, kardio- i cerebrovaskularnih ateroskleroznih poremećaja, bolesti perifernih arterija, reumatoidnog artritisa, plućnih bolesti poput COPD, astme ili boli.
15. Upotreba spoja formule (I) kako je definirano u bilo kojem zahtjevu 1 do 10, ili njegove farmaceutski prihvatljive soli, naznačena time, da se navedeni spoj upotrebljava za proizvodnju lijeka za liječenje ili profilaksu multiple skleroze.
16. Upotreba spoja formule (I) kako je definirano u bilo kojem zahtjevu 1 do 10, ili njegove farmaceutski prihvatljive soli, naznačena time, da se navedeni spoj upotrebljava za proizvodnju lijeka za liječenje ili profilaksu ateroskleroze pomoću promjene sastava plakova, u svrhu smanjenja rizika od pucanja plaka i pojave aterotrombotskih događaja.
17. Upotreba spoja formule (I) kako je definirano u bilo kojem zahtjevu 1 do 10, ili njegove farmaceutski prihvatljive soli, naznačena time, da se navedeni spoj upotrebljava za proizvodnju lijeka za liječenje ili profilaksu ateroskleroze pomoću prevencije i/ili smanjenja postupka stvaranja novih ateroskleroznih lezija ili plakova i/ili pomoću prevencije ili usporavanja napredovanja postojećih lezija i plakova.
18. Postupak za pripremu spoja formule (I), kako je definirano u bilo kojem zahtjevu 1 do 10, ili njegove farmaceutski prihvatljive soli, naznačen time, da navedeni postupak uključuje:
a) reakciju spoja formule (II):
[image]
pri čemu R3, R4 i R5 su kako je definirano u formuli (I);
sa nekim spojem formule (III):
[image]
pri čemu R1 i R2 su kako je definirano u formuli (I), i L1 predstavlja odlaznu skupinu; ili
b) reakciju spoja formule (IV)
[image]
pri čemu R1 i R2 su kako je definirano u formuli (I), i L2 predstavlja odlaznu skupinu; sa spojem formule (V)
[image]
pri čemu R3, R4 i R5 su kako je definirano u formuli (I);
i, gdje je potrebno, pretvorbu tako dobivenog spoja formule (I), ili druge njegove soli, u njegovu farmaceutski prihvatljivu sol; ili pretvorbu tako dobivenog spoja formule (I) u drugi spoj formule (I); i po potrebi, pretvorbe tako dobivenog spoja formule (I) u njegov optički izomer.
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| PCT/SE2006/000399 WO2006107258A1 (en) | 2005-04-06 | 2006-04-03 | Novel 5-substituted 7-amino-[1,3]thiazolo[4,5-d]pyrimidine derivatives |
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| HRP20110047T1 true HRP20110047T1 (hr) | 2011-03-31 |
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| WO2006046739A1 (ja) | 2004-10-29 | 2006-05-04 | Eisai R & D Management Co., Ltd. | 炎症性疾患治療剤 |
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| KR20090057075A (ko) * | 2006-09-29 | 2009-06-03 | 아스트라제네카 아베 | 신규한 5,7-이치환된 [1,3]티아졸로[4,5-ｄ]피리미딘-2(3ｈ)-아민 유도체 및 요법에서 그의 용도 |
| TW200820973A (en) | 2006-09-29 | 2008-05-16 | Astrazeneca Ab | Novel compounds 480 |
| CA2715065C (en) | 2008-03-07 | 2017-06-27 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. | Novel 1-benzyl-3-hydroxymethylindazole derivatives and use thereof in the treatment of diseases based on the expression mcp-1 and cx3cr1 |
| KR101581828B1 (ko) | 2008-03-07 | 2015-12-31 | 아지엔드 키미쉐 리유나이트 안젤리니 프란체스코 에이.씨.알.에이.에프. 에스.피.에이 | 신규한 1-벤질-3-하이드록시메틸인다졸 유도체들 및 ｍｃｐ-1, ｃｘ3ｃｒ1 및 ｐ40의 발현을 기초로 한 질환들의 치료에서 이의 용도 |
| KR101640844B1 (ko) | 2008-03-07 | 2016-07-19 | 아지엔드 키미쉐 리유나이트 안젤리니 프란체스코 에이.씨.알.에이.에프. 에스.피.에이 | 1-벤질-3-하이드록시메틸인다졸 유도체들 및 ｍｃｐ-1, ｃｘ3ｃｒ1 및 ｐ40의 발현을 기초로 한 질환들의 치료에서 이의 용도 |
| WO2010132999A1 (en) | 2009-05-21 | 2010-11-25 | Chlorion Pharma, Inc. | Methyl sulfanyl pyrmidmes useful as antiinflammatories, analgesics, and antiepileptics |
| JO3437B1 (ar) | 2009-10-30 | 2019-10-20 | Esai R & D Man Co Ltd | أجسام مضادة محسنة مضادة للفراكتالكين البشري واستخداماتها |
| US8435993B2 (en) | 2010-12-07 | 2013-05-07 | Philadelphia Health And Education Corporation | Methods of inhibiting metastasis from cancer |
| US8476301B2 (en) | 2011-09-13 | 2013-07-02 | Eisai R&D Management Co., Ltd. | Pyrrolidin-3-ylacetic acid derivative |
| TWI543975B (zh) | 2011-09-13 | 2016-08-01 | Eisai R&D Man Co Ltd | Pyrrolidin-3-yl acetic acid derivatives |
| JP5872105B2 (ja) | 2013-03-12 | 2016-03-01 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ピロリジン−３−イル酢酸誘導体の塩およびその結晶 |
| JP2016531870A (ja) * | 2013-09-27 | 2016-10-13 | ニンバス アイリス， インコーポレイテッド | Ｉｒａｋ阻害剤およびその使用 |
| WO2016200939A1 (en) * | 2015-06-08 | 2016-12-15 | The Johns Hopkins University | Radiofluorinated 7-amino-5-thio-thiazolo[4,5-d]pyrimidines for imaging fractalkine receptor (cx3cr1) |
| US11267817B2 (en) | 2017-05-02 | 2022-03-08 | Drexel University | Substituted pyrrolo[1,2-a]quinoxalin-4(5H)-ones as CX3CR1 antagonists |
| GB201807898D0 (en) * | 2018-05-15 | 2018-06-27 | Kancera Ab | New processes and products with increased chiral purity |
| GB201811169D0 (en) | 2018-07-06 | 2018-08-29 | Kancera Ab | New compounds |
| GB202006849D0 (en) | 2020-05-08 | 2020-06-24 | Kancera Ab | New use |
| WO2024083933A1 (en) | 2022-10-19 | 2024-04-25 | Astrazeneca Ab | 2,4,6-trisubstituted 1,3,5-triazines as modulators of cx 3cr1 |
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| BE543978A (hr) | 1955-01-03 | |||
| US4698327A (en) | 1985-04-25 | 1987-10-06 | Eli Lilly And Company | Novel glycopeptide derivatives |
| US4639433A (en) | 1985-08-14 | 1987-01-27 | Eli Lilly And Company | Glycopeptide derivatives |
| US4643987A (en) | 1985-08-14 | 1987-02-17 | Eli Lilly And Company | Modified glycopeptides |
| ZA909847B (en) | 1989-12-13 | 1992-08-26 | Lilly Co Eli | Glycopeptide derivatives |
| US5202328A (en) | 1991-03-06 | 1993-04-13 | Merck & Co., Inc. | Substituted fused pyrimidinones |
| US5840684A (en) | 1994-01-28 | 1998-11-24 | Eli Lilly And Company | Glycopeptide antibiotic derivatives |
| CA2326884A1 (en) | 1998-04-03 | 1999-10-14 | Dupont Pharmaceuticals Company | Thiazolo¬4,5-d|pyrimidines and pyridines as corticotropin releasing factor (crf) antagonists |
| DK1073447T3 (da) | 1998-05-01 | 2007-09-03 | Lilly Co Eli | N1-modificerede glycopeptider |
| SE9802729D0 (sv) * | 1998-08-13 | 1998-08-13 | Astra Pharma Prod | Novel Compounds |
| SE9903544D0 (sv) | 1999-10-01 | 1999-10-01 | Astra Pharma Prod | Novel compounds |
| ATE255584T1 (de) * | 2000-02-11 | 2003-12-15 | Astrazeneca Ab | Pyrimidinverbindungen und ihre verwendung als modulatoren der chemokin-rezeptor-aktivität |
| GB2359081A (en) * | 2000-02-11 | 2001-08-15 | Astrazeneca Uk Ltd | Pharmaceutically active thiazolopyrimidines |
| GB2359551A (en) | 2000-02-23 | 2001-08-29 | Astrazeneca Uk Ltd | Pharmaceutically active pyrimidine derivatives |
| SE0004110L (sv) | 2000-11-10 | 2002-05-11 | Forsheda Ab | Tätningsring |
| SE0101082D0 (sv) | 2001-03-27 | 2001-03-27 | Astrazeneca Ab | Novel use |
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| GB0221829D0 (en) | 2002-09-20 | 2002-10-30 | Astrazeneca Ab | Novel compound |
| GB0221828D0 (en) | 2002-09-20 | 2002-10-30 | Astrazeneca Ab | Novel compound |
| AU2003299795A1 (en) * | 2002-12-20 | 2004-07-22 | Xeris Pharmaceuticals, Inc. | Intracutaneous injection |
| AU2004278276B2 (en) * | 2003-10-07 | 2007-10-18 | Astrazeneca Ab | New 2-substituted, 4-amino-thiazolo(4,5-d) pyrimidines, useful as chemokine receptor antagonists, esp. CX3CR1 |
| WO2006064228A2 (en) * | 2004-12-17 | 2006-06-22 | Astrazeneca Ab | Thiazolopyramidine compounds for the modulation of chemokine receptor activity |
| AR053347A1 (es) * | 2005-04-06 | 2007-05-02 | Astrazeneca Ab | Derivados de [1,3]tiazolo[4,5-d]pirimidin-2(3h)-ona 5,7-sustituidos |
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