JP2007527908A5 - - Google Patents
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- Publication number
- JP2007527908A5 JP2007527908A5 JP2007502926A JP2007502926A JP2007527908A5 JP 2007527908 A5 JP2007527908 A5 JP 2007527908A5 JP 2007502926 A JP2007502926 A JP 2007502926A JP 2007502926 A JP2007502926 A JP 2007502926A JP 2007527908 A5 JP2007527908 A5 JP 2007527908A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridine
- imidazo
- group
- carboxamidine
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 238000000034 method Methods 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 239000008194 pharmaceutical composition Substances 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims 9
- 125000003107 substituted aryl group Chemical group 0.000 claims 9
- 239000011541 reaction mixture Substances 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 6
- 229920006395 saturated elastomer Polymers 0.000 claims 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 5
- -1 alkoxycycloalkyl Chemical group 0.000 claims 5
- 239000003054 catalyst Substances 0.000 claims 5
- 208000015181 infectious disease Diseases 0.000 claims 5
- KMHCTFSFWQRZTR-UHFFFAOYSA-N 3-aminopyridine-2-carbonitrile Chemical compound NC1=CC=CN=C1C#N KMHCTFSFWQRZTR-UHFFFAOYSA-N 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 claims 4
- 239000003586 protic polar solvent Substances 0.000 claims 4
- YDTLZSQZMCRIER-UHFFFAOYSA-N 2-[(z)-n'-hydroxycarbamimidoyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=CC=CN2C(C(=O)N)=C(C(N)=NO)N=C21 YDTLZSQZMCRIER-UHFFFAOYSA-N 0.000 claims 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- DUADCMJZEJDULX-UHFFFAOYSA-N C1=CC=CN2C(C(N)=N)=C(C(=N)N)N=C21 Chemical class C1=CC=CN2C(C(N)=N)=C(C(=N)N)N=C21 DUADCMJZEJDULX-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 125000004423 acyloxy group Chemical group 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 125000005350 hydroxycycloalkyl group Chemical group 0.000 claims 3
- 230000000813 microbial effect Effects 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- IUXFKUNLXPVYIV-UHFFFAOYSA-N 2-[3-(4-carbamimidoylphenyl)phenyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6-carboximidamide Chemical compound C=1N2CC(C(=N)N)CCC2=NC=1C(C=1)=CC=CC=1C1=CC=C(C(N)=N)C=C1 IUXFKUNLXPVYIV-UHFFFAOYSA-N 0.000 claims 2
- QWEUWPVGJHUPTI-UHFFFAOYSA-N 2-[3-(4-carbamimidoylphenyl)phenyl]-8-methylimidazo[1,2-a]pyridine-6-carboximidamide Chemical compound N1=C2C(C)=CC(C(N)=N)=CN2C=C1C(C=1)=CC=CC=1C1=CC=C(C(N)=N)C=C1 QWEUWPVGJHUPTI-UHFFFAOYSA-N 0.000 claims 2
- UTMXCUWVXRZXPO-UHFFFAOYSA-N 2-[3-(4-carbamimidoylphenyl)phenyl]imidazo[1,2-a]pyridine-6-carboximidamide Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC=CC(C=2N=C3C=CC(=CN3C=2)C(N)=N)=C1 UTMXCUWVXRZXPO-UHFFFAOYSA-N 0.000 claims 2
- AUDUAIQWVZGFHX-UHFFFAOYSA-N 2-[4-(4-carbamimidoylphenyl)phenyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6-carboximidamide Chemical compound C=1N2CC(C(=N)N)CCC2=NC=1C(C=C1)=CC=C1C1=CC=C(C(N)=N)C=C1 AUDUAIQWVZGFHX-UHFFFAOYSA-N 0.000 claims 2
- OTQBRWYINPWMAY-UHFFFAOYSA-N 2-[4-(4-carbamimidoylphenyl)phenyl]imidazo[1,2-a]pyridine-6-carboximidamide Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC=C(C=2N=C3C=CC(=CN3C=2)C(N)=N)C=C1 OTQBRWYINPWMAY-UHFFFAOYSA-N 0.000 claims 2
- JXYYCJXMMMWGJM-UHFFFAOYSA-N 2-[5-(4-carbamimidoylphenyl)furan-2-yl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6-carboximidamide Chemical compound C=1N2CC(C(=N)N)CCC2=NC=1C(O1)=CC=C1C1=CC=C(C(N)=N)C=C1 JXYYCJXMMMWGJM-UHFFFAOYSA-N 0.000 claims 2
- BPRKMPXUHWFKSO-UHFFFAOYSA-N 2-[5-(4-carbamimidoylphenyl)furan-2-yl]-8-methylimidazo[1,2-a]pyridine-6-carboximidamide Chemical compound N1=C2C(C)=CC(C(N)=N)=CN2C=C1C(O1)=CC=C1C1=CC=C(C(N)=N)C=C1 BPRKMPXUHWFKSO-UHFFFAOYSA-N 0.000 claims 2
- SPCAOBGQKXEQHK-UHFFFAOYSA-N 2-[5-(4-carbamimidoylphenyl)furan-2-yl]imidazo[1,2-a]pyridine-6-carboximidamide Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC=C(C=2N=C3C=CC(=CN3C=2)C(N)=N)O1 SPCAOBGQKXEQHK-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical group Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 125000005907 alkyl ester group Chemical group 0.000 claims 2
- 125000005233 alkylalcohol group Chemical group 0.000 claims 2
- 239000002168 alkylating agent Substances 0.000 claims 2
- 229940100198 alkylating agent Drugs 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- ZXZBMGGWHWRHPS-UHFFFAOYSA-N cyanato(phenyl)borinic acid Chemical compound N#COB(O)C1=CC=CC=C1 ZXZBMGGWHWRHPS-UHFFFAOYSA-N 0.000 claims 2
- 125000004802 cyanophenyl group Chemical group 0.000 claims 2
- IZEYIAVFSOQZCD-UHFFFAOYSA-N n'-hydroxy-2-[3-[4-(n'-hydroxycarbamimidoyl)phenyl]phenyl]-8-methylimidazo[1,2-a]pyridine-6-carboximidamide Chemical compound N1=C2C(C)=CC(C(=N)NO)=CN2C=C1C(C=1)=CC=CC=1C1=CC=C(C(=N)NO)C=C1 IZEYIAVFSOQZCD-UHFFFAOYSA-N 0.000 claims 2
- AKEXDYLCIVUTSU-UHFFFAOYSA-N n'-hydroxy-2-[3-[4-[(e)-n'-hydroxycarbamimidoyl]phenyl]phenyl]imidazo[1,2-a]pyridine-6-carboximidamide Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=CC(C=2N=C3C=CC(=CN3C=2)C(=N)NO)=C1 AKEXDYLCIVUTSU-UHFFFAOYSA-N 0.000 claims 2
- SMXXOXWUDRKNFL-UHFFFAOYSA-N n'-hydroxy-2-[4-[4-[(e)-n'-hydroxycarbamimidoyl]phenyl]phenyl]imidazo[1,2-a]pyridine-6-carboximidamide Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2N=C3C=CC(=CN3C=2)C(=N)NO)C=C1 SMXXOXWUDRKNFL-UHFFFAOYSA-N 0.000 claims 2
- ONWNNQXNIDRZNB-UHFFFAOYSA-N n'-hydroxy-2-[5-[4-[(e)-n'-hydroxycarbamimidoyl]phenyl]furan-2-yl]-8-methylimidazo[1,2-a]pyridine-6-carboximidamide Chemical compound N1=C2C(C)=CC(C(=N)NO)=CN2C=C1C(O1)=CC=C1C1=CC=C(C(=N)NO)C=C1 ONWNNQXNIDRZNB-UHFFFAOYSA-N 0.000 claims 2
- JBKBGFMARUWNDU-UHFFFAOYSA-N n'-hydroxy-2-[5-[4-[(e)-n'-hydroxycarbamimidoyl]phenyl]furan-2-yl]imidazo[1,2-a]pyridine-6-carboximidamide Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2N=C3C=CC(=CN3C=2)C(=N)NO)O1 JBKBGFMARUWNDU-UHFFFAOYSA-N 0.000 claims 2
- TVIBDWKPVCACMM-UHFFFAOYSA-N n'-methoxy-2-[4-[4-[(e)-n'-methoxycarbamimidoyl]phenyl]phenyl]imidazo[1,2-a]pyridine-6-carboximidamide Chemical compound C1=CC(C(=N)NOC)=CC=C1C1=CC=C(C=2N=C3C=CC(=CN3C=2)C(=N)NOC)C=C1 TVIBDWKPVCACMM-UHFFFAOYSA-N 0.000 claims 2
- VQTUZOCVRYCMAL-UHFFFAOYSA-N n'-methoxy-2-[5-[4-[(e)-n'-methoxycarbamimidoyl]phenyl]furan-2-yl]imidazo[1,2-a]pyridine-6-carboximidamide Chemical compound C1=CC(C(=N)NOC)=CC=C1C1=CC=C(C=2N=C3C=CC(=CN3C=2)C(=N)NOC)O1 VQTUZOCVRYCMAL-UHFFFAOYSA-N 0.000 claims 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical group [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 2
- XDBHWPLGGBLUHH-UHFFFAOYSA-N (3-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C#N)=C1 XDBHWPLGGBLUHH-UHFFFAOYSA-N 0.000 claims 1
- CEBAHYWORUOILU-UHFFFAOYSA-N (4-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=C(C#N)C=C1 CEBAHYWORUOILU-UHFFFAOYSA-N 0.000 claims 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 1
- MZBXSQBQPJWECM-UHFFFAOYSA-N 2-bromo-1-(3-bromophenyl)ethanone Chemical compound BrCC(=O)C1=CC=CC(Br)=C1 MZBXSQBQPJWECM-UHFFFAOYSA-N 0.000 claims 1
- FKJSFKCZZIXQIP-UHFFFAOYSA-N 2-bromo-1-(4-bromophenyl)ethanone Chemical compound BrCC(=O)C1=CC=C(Br)C=C1 FKJSFKCZZIXQIP-UHFFFAOYSA-N 0.000 claims 1
- WTFKIDCAQZPAHP-UHFFFAOYSA-N 2-bromo-1-(5-bromofuran-2-yl)ethanone Chemical group BrCC(=O)C1=CC=C(Br)O1 WTFKIDCAQZPAHP-UHFFFAOYSA-N 0.000 claims 1
- LJANCPRIUMHGJE-UHFFFAOYSA-N 4-(2-bromoacetyl)benzonitrile Chemical compound BrCC(=O)C1=CC=C(C#N)C=C1 LJANCPRIUMHGJE-UHFFFAOYSA-N 0.000 claims 1
- KBLGGRWUEVCNPY-UHFFFAOYSA-N 5-bromo-3-methylpyridin-2-amine Chemical compound CC1=CC(Br)=CN=C1N KBLGGRWUEVCNPY-UHFFFAOYSA-N 0.000 claims 1
- WGOLHUGPTDEKCF-UHFFFAOYSA-N 5-bromopyridin-2-amine Chemical compound NC1=CC=C(Br)C=N1 WGOLHUGPTDEKCF-UHFFFAOYSA-N 0.000 claims 1
- SLOISJVQLUVVSD-UHFFFAOYSA-N 6-amino-5-methylpyridine-3-carbonitrile Chemical group CC1=CC(C#N)=CN=C1N SLOISJVQLUVVSD-UHFFFAOYSA-N 0.000 claims 1
- KDVBYUUGYXUXNL-UHFFFAOYSA-N 6-aminopyridine-3-carbonitrile Chemical group NC1=CC=C(C#N)C=N1 KDVBYUUGYXUXNL-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 241000223960 Plasmodium falciparum Species 0.000 claims 1
- 241000223104 Trypanosoma Species 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 150000003927 aminopyridines Chemical class 0.000 claims 1
- 150000008050 dialkyl sulfates Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical group C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 0 CC1=CC=C(C)*1 Chemical compound CC1=CC=C(C)*1 0.000 description 3
- GNVAHRNNOJKIIK-UHFFFAOYSA-N CC(CC=C1)C1S Chemical compound CC(CC=C1)C1S GNVAHRNNOJKIIK-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55109104P | 2004-03-08 | 2004-03-08 | |
| PCT/US2005/007566 WO2005086808A2 (en) | 2004-03-08 | 2005-03-08 | NOVEL DICATIONIC IMIDAZO[1,2-a]PYRIDINES AND 5,6,7,8-TETRAHYDRO-IMIDAZO[1,2a]PYRIDINES AS ANTIPROTOZOAL AGENTS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007527908A JP2007527908A (ja) | 2007-10-04 |
| JP2007527908A5 true JP2007527908A5 (enExample) | 2008-04-03 |
Family
ID=34976160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007502926A Pending JP2007527908A (ja) | 2004-03-08 | 2005-03-08 | 抗原虫薬としての新規ジカチオン性イミダゾ［１，２−ａ］ピリジン、及び５，６，７，８−テトラヒドロ−イミダゾ［１，２−ａ］ピリジン |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7432278B2 (enExample) |
| EP (1) | EP1745045A4 (enExample) |
| JP (1) | JP2007527908A (enExample) |
| CN (1) | CN1930159A (enExample) |
| AU (1) | AU2005220882A1 (enExample) |
| CA (1) | CA2554554A1 (enExample) |
| WO (1) | WO2005086808A2 (enExample) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2906250B1 (fr) * | 2006-09-22 | 2008-10-31 | Sanofi Aventis Sa | Derives de 2-aryl-6phenyl-imidazo(1,2-a) pyridines, leur preparation et leur application en therapeutique |
| CA2669522A1 (en) * | 2006-11-17 | 2008-05-22 | Nihon Medi-Physics Co., Ltd. | Novel compounds with affinity for amyloid |
| EP1964840A1 (en) | 2007-02-28 | 2008-09-03 | sanofi-aventis | Imidazo[1,2-a]pyridines and their use as pharmaceuticals |
| KR20100101576A (ko) * | 2007-10-30 | 2010-09-17 | 니혼 메디피직스 가부시키가이샤 | 신규 아밀로이드 친화성 화합물의 사용 및 제조 방법 |
| US9186361B2 (en) * | 2013-03-15 | 2015-11-17 | Novartis Ag | Compounds and compositions for the treatment of parasitic diseases |
| US9296754B2 (en) | 2013-03-15 | 2016-03-29 | Novartis Ag | Compounds and compositions for the treatment of parasitic diseases |
| WO2014151630A2 (en) | 2013-03-15 | 2014-09-25 | Irm Llc | Compounds and compositions for the treatment of parasitic diseases |
| PE20160865A1 (es) | 2013-12-19 | 2016-09-03 | Novartis Ag | Derivados de [1,2,4] triazolo [1,5-a]pirimidina como inhibidores de proteasoma para el tratamiento de enfermedades parasitarias tales como leishmaniasis |
| KR20170137165A (ko) | 2015-04-10 | 2017-12-12 | 베이진 엘티디 | 인돌아민 및/또는 트립토판 2,3-디옥시게나아제로서 신규한 5 또는 8-치환된 이미다조[1,5-a]피리딘 |
| ES2928164T3 (es) | 2015-10-19 | 2022-11-15 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| HUE060680T2 (hu) | 2015-11-19 | 2023-04-28 | Incyte Corp | Heterociklusos vegyületek mint immunmodulátorok |
| DK3394033T3 (da) | 2015-12-22 | 2021-01-04 | Incyte Corp | Heterocykliske forbindelser som immunmodulatorer |
| MA44860A (fr) | 2016-05-06 | 2019-03-13 | Incyte Holdings Corp | Composés hétérocycliques utilisés comme immunomodulateurs |
| WO2017205464A1 (en) | 2016-05-26 | 2017-11-30 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| SG11201811414TA (en) | 2016-06-20 | 2019-01-30 | Incyte Corp | Heterocyclic compounds as immunomodulators |
| ES2930092T3 (es) | 2016-07-14 | 2022-12-07 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| EP3504198B1 (en) | 2016-08-29 | 2023-01-25 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| EP3515914A4 (en) * | 2016-09-24 | 2020-04-15 | BeiGene, Ltd. | NEW IMIDAZO [1,5-A] PYRIDINES SUBSTITUTED IN POSITION 5 OR 8 AS INDOLEAMINE AND / OR TRYPTOPHANE 2,3-DIOXYGENASES |
| US20180179179A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| EP3558989B1 (en) | 2016-12-22 | 2021-04-14 | Incyte Corporation | Triazolo[1,5-a]pyridine derivatives as immunomodulators |
| MD3558990T2 (ro) | 2016-12-22 | 2023-02-28 | Incyte Corp | Derivați tetrahidro imidazo[4,5-c]piridină ca inductori de internalizare a PD-L1 |
| MA47123A (fr) | 2016-12-22 | 2021-03-17 | Incyte Corp | Dérivés de benzooxazole en tant qu'mmunomodulateurs |
| CA3047991A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Bicyclic heteroaromatic compounds as immunomodulators |
| US11472788B2 (en) | 2017-11-25 | 2022-10-18 | Beigene, Ltd. | Benzoimidazoles as selective inhibitors of indoleamine 2,3-dioxygenases |
| KR102708681B1 (ko) | 2018-02-13 | 2024-09-26 | 길리애드 사이언시즈, 인코포레이티드 | Pd-1/pd-l1 억제제 |
| US10669271B2 (en) | 2018-03-30 | 2020-06-02 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| EP3781556B1 (en) | 2018-04-19 | 2025-06-18 | Gilead Sciences, Inc. | Pd-1/pd-l1 inhibitors |
| LT3790877T (lt) | 2018-05-11 | 2023-05-10 | Incyte Corporation | Tetrahidro-imidazo[4,5-c]piridino dariniai kaip pd-l1 imunomoduliatoriai |
| CN118221646A (zh) | 2018-07-13 | 2024-06-21 | 吉利德科学公司 | Pd-1/pd-l1抑制剂 |
| KR102635333B1 (ko) | 2018-10-24 | 2024-02-15 | 길리애드 사이언시즈, 인코포레이티드 | Pd-1/pd-l1 억제제 |
| AU2019416589B2 (en) * | 2018-12-29 | 2023-04-06 | Wuhan Ll Science And Technology Development Co., Ltd. | Heterocyclic compound intermediate, preparation method therefor and application thereof |
| TW202115059A (zh) | 2019-08-09 | 2021-04-16 | 美商英塞特公司 | Ｐｄ—１／ｐｄ—ｌ１抑制劑之鹽 |
| EP4037773A1 (en) | 2019-09-30 | 2022-08-10 | Incyte Corporation | Pyrido[3,2-d]pyrimidine compounds as immunomodulators |
| PE20230407A1 (es) | 2019-11-11 | 2023-03-07 | Incyte Corp | Sales y formas cristalinas de un inhibidor de pd-1/pd-l1 |
| EP4603484A2 (en) | 2019-12-19 | 2025-08-20 | Georgia State University Research Foundation, Inc. | Compounds for the treatment of bacterial infections and potentiation of antibiotics |
| WO2022099071A1 (en) | 2020-11-06 | 2022-05-12 | Incyte Corporation | Process for making a pd-1/pd-l1 inhibitor and salts and crystalline forms thereof |
| US11780836B2 (en) | 2020-11-06 | 2023-10-10 | Incyte Corporation | Process of preparing a PD-1/PD-L1 inhibitor |
| WO2022099075A1 (en) | 2020-11-06 | 2022-05-12 | Incyte Corporation | Crystalline form of a pd-1/pd-l1 inhibitor |
| CN118440080B (zh) * | 2024-05-08 | 2024-12-20 | 广东省科学院微生物研究所(广东省微生物分析检测中心) | 三苯胺类阳离子化合物及其制备方法和应用 |
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| US5204352A (en) * | 1987-09-29 | 1993-04-20 | The United States Of America As Represented By The Secretary Of The Army | Compounds exhibiting anti-parasitic activity and a method for their use |
| AU6168296A (en) | 1995-06-07 | 1996-12-30 | The Administrators Of The Tulane Eductional Fund | Chloroquine analogs and methods of preventing and treating p lasmodial disease |
| JP4041624B2 (ja) * | 1999-07-21 | 2008-01-30 | 三井化学株式会社 | 有機電界発光素子 |
| ITMI20031754A1 (it) | 2003-09-12 | 2005-03-13 | Fabrizio Marcucci | Composizione microbicida. |
-
2005
- 2005-03-08 AU AU2005220882A patent/AU2005220882A1/en not_active Abandoned
- 2005-03-08 WO PCT/US2005/007566 patent/WO2005086808A2/en not_active Ceased
- 2005-03-08 EP EP05733801A patent/EP1745045A4/en not_active Withdrawn
- 2005-03-08 CN CNA2005800073247A patent/CN1930159A/zh active Pending
- 2005-03-08 CA CA002554554A patent/CA2554554A1/en not_active Abandoned
- 2005-03-08 JP JP2007502926A patent/JP2007527908A/ja active Pending
- 2005-03-08 US US11/074,565 patent/US7432278B2/en not_active Expired - Fee Related
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