HRP20210965T1 - Derivati pirazolilaminobenzimidazola kao jak inhibitori - Google Patents
Derivati pirazolilaminobenzimidazola kao jak inhibitori Download PDFInfo
- Publication number
- HRP20210965T1 HRP20210965T1 HRP20210965TT HRP20210965T HRP20210965T1 HR P20210965 T1 HRP20210965 T1 HR P20210965T1 HR P20210965T T HRP20210965T T HR P20210965TT HR P20210965 T HRP20210965 T HR P20210965T HR P20210965 T1 HRP20210965 T1 HR P20210965T1
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- Croatia
- Prior art keywords
- compound according
- pharmaceutically acceptable
- image
- acceptable salt
- amino
- Prior art date
Links
- 229940122245 Janus kinase inhibitor Drugs 0.000 title 1
- DHHDAEXWDQTBIJ-UHFFFAOYSA-N n-(1h-pyrazol-5-yl)-1h-benzimidazol-2-amine Chemical class N=1C2=CC=CC=C2NC=1NC1=CC=NN1 DHHDAEXWDQTBIJ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 11
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 229910016523 CuKa Inorganic materials 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 2
- 238000001228 spectrum Methods 0.000 claims 2
- YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (19)
1. Spoj formule, ili njegova farmaceutski prihvatljiva sol
[image]
gdje R je izabran između: H, -C1-3 alkil, -CH2CH(OH)CH3, -C2-3 alkil-O-CH3,
[image]
R1 je izabran između: H, -CH3, i -OCH3;
R2 je -CHF2 ili -CF3; i
R3 je H ili -CH3;
uz uvjet da kada R2 je -CF3 i R3 je H, ili R ili R1 mogu biti -CH3, ali ne oba.
2. Spoj prema zahtjevu 1 formule, ili njegova farmaceutski prihvatljiva sol,
[image]
gdje:
R je izabran između: H, -C1-3 alkil, -CH2CH(OH)CH3, -C2-3 alkil-O-CH3,
[image]
i
[image]
R1 je izabran između: H, -CH3, i -OCH3;
R2 je -CHF2 ili -CF3; i
R3 je H ili -CH3;
uz uvjet da kad R2 je -CF3, i R3 je H, ili R ili R1 mogu biti -CH3, ali ne oba.
3. Spoj prema zahtjevu 1 ili 2 gdje R je izabran između: -CH3, -CH2CH3, i
[image]
ili njegova farmaceutski prihvatljiva sol.
4. Spoj prema bilo kojem od zahtjeva 1 do 3 gdje R je -CH3, ili -CH2CH3, ili njegova farmaceutski prihvatljiva sol.
5. Spoj prema bilo kojem od zahtjeva 1 do 3 gdje R je
[image]
ili njegova farmaceutski prihvatljiva sol.
6. Spoj prema bilo kojem od zahtjeva 1 do 5 gdje R2 je -CF3, ili njegova farmaceutski prihvatljiva sol.
7. Spoj prema bilo kojem od zahtjeva 1 do 6 gdje R3 je -CH3, ili njegova farmaceutski prihvatljiva sol.
8. Spoj prema bilo kojem od zahtjeva 1 do 4 koje je
[image]
ili njegova farmaceutski prihvatljiva sol.
9. Spoj prema bilo kojem od zahtjeva 1 do 4 koje je
[image]
ili njegova farmaceutski prihvatljiva sol.
10. Spoj prema zahtjevu 1 ili 2 koje je
[image]
ili njegova farmaceutski prihvatljiva sol.
11. Spoj prema bilo kojem od zahtjeva 1 do 3, ili 5 koje je
[image]
ili njegova farmaceutski prihvatljiva sol.
12. Spoj prema bilo kojem od zahtjeva 1 do 3, ili 5 koje je (2R)-1,1,1-trifluoro-3-({cis-4-[(1-metil-4-{[1-(piridin-2-il)-1H-pirazol-3-il]amino}-1H-benzimidazol-6-il)oksi]cikloheksil}amino)propan-2-ol2-hidroksipropan-1,2,3-trikarboksilat hidrat.
13. Spoj prema bilo kojem od zahtjeva 1 do 3, ili 5 koje je (2R)-1,1,1-trifluoro-3-({cis-4-[(1-metil-4-{[1-(piridin-2-il)-1H-pirazol-3-il]amino}-1H-benzimidazol-6-il)oksi]cikloheksil}amino)propan-2-ol u kristalnom obliku karakteriziranom spektrom difrakcije X-zraka na prahu dobivenom sa CuKa izvorom (λ=1.54060 Å), koji ima signal na 20.5 u kombinaciji sa jednim ili više signala izabranih iz grupe koju čine 15.5, 18.1, 18.3, 18.5, 22.9 i 23.6; sa odstupanjem difrakcijskih uglova od 0.2 stupnjeva.
14. Spoj prema bilo kojem od zahtjeva 1 do 3, ili 5 koje je (2R)-1,1,1-trifluoro-3-({cis-4-[(1-metil-4-{[1-(piridin-2-il)-1H-pirazol-3-il]amino}-1H-benzimidazol-6-il)oksi]cikloheksil}amino)propan-2-ol 2-hidroksipropan-1,2,3-trikarboksilat hidrat u kristalnom obliku karakteriziranom spektrom difrakcije X-zraka na prahu dobivenom pomoću CuKa izvora (λ=1.54060 Å), koji ima signal na 17.9 u kombinaciji sa jednim ili više signala izabranih iz grupe koju čine 26.1, 26.6 i 22.7; sa odstupanjem difrakcijskih uglova od 0.2 stupnjeva.
15. Farmaceutski sastav koji sadrži spoj prema bilo kojem od zahtjeva 1 do 14 i farmaceutski prihvatljiv nositelj, razblaživač ili ekscipijent.
16. Farmaceutski sastav prema zahtjevu 15 koji sadrži više od 80% m/m spoja koji je (2R)-1,1,1-trifluoro-3-({cis-4-[(1-metil-4-{[1-(piridin-2-il)-1H-pirazol-3-il]amino}-1H-benzimidazol-6-il)oksi]cikloheksil}amino)propan-2-ol2-hidroksipropan-1,2,3-trikarboksilat hidrat u kristalnom obliku.
17. Farmaceutski sastav prema zahtjevu 15 koja sadrži više od 90 % m/m spoja koji je (2R)-1,1,1-trifluoro-3-({cis-4-[(1-metil-4-{[1-(piridin-2-il)-1H-pirazol-3-il]amino}-1H-benzimidazol-6-il)oksi]cikloheksil}amino)propan-2-ol2-hidroksipropan-1,2,3-trikarboksilat hidrat u kristalnom obliku.
18. Spoj prema bilo kojem od zahtjeva 1 do 14 za upotrebu u liječenju.
19. Spoj prema bilo kojem od zahtjeva 1 do 14 za upotrebu u liječenju artritisa.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201662362208P | 2016-07-14 | 2016-07-14 | |
PCT/US2017/041388 WO2018013486A1 (en) | 2016-07-14 | 2017-07-10 | Pyrazolylaminobenzimidazole derivatives as jak inhibitors |
EP17740885.3A EP3484875B1 (en) | 2016-07-14 | 2017-07-10 | Pyrazolylaminobenzimidazole derivatives as jak inhibitors |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20210965T1 true HRP20210965T1 (hr) | 2021-09-17 |
Family
ID=59366549
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20210965TT HRP20210965T1 (hr) | 2016-07-14 | 2021-06-17 | Derivati pirazolilaminobenzimidazola kao jak inhibitori |
Country Status (22)
Country | Link |
---|---|
US (2) | US10323019B2 (hr) |
EP (1) | EP3484875B1 (hr) |
JP (1) | JP6712331B2 (hr) |
KR (1) | KR102225840B1 (hr) |
CN (1) | CN109476643B (hr) |
AU (1) | AU2017296026B2 (hr) |
BR (1) | BR112018075086B1 (hr) |
CA (1) | CA3030697C (hr) |
CY (1) | CY1124308T1 (hr) |
DK (1) | DK3484875T3 (hr) |
EA (1) | EA038129B1 (hr) |
ES (1) | ES2877198T3 (hr) |
HR (1) | HRP20210965T1 (hr) |
HU (1) | HUE054912T2 (hr) |
LT (1) | LT3484875T (hr) |
MX (1) | MX2019000542A (hr) |
NZ (1) | NZ748942A (hr) |
PL (1) | PL3484875T3 (hr) |
PT (1) | PT3484875T (hr) |
RS (1) | RS61991B1 (hr) |
SI (1) | SI3484875T1 (hr) |
WO (1) | WO2018013486A1 (hr) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20230141115A (ko) | 2022-03-31 | 2023-10-10 | 한림대학교 산학협력단 | 신규한 2-아릴-1H-벤조[d]이미다졸 유도체, 이의 제조 방법 및 이의 항암제로서의 용도 |
KR102582097B1 (ko) | 2022-12-28 | 2023-09-25 | (주)메디언스 | 야누스키나아제 표적 억제제 및 이의 용도 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2155742A1 (en) * | 2007-04-18 | 2010-02-24 | AstraZeneca AB | 5-aminopyrazol-3-yl-3h-imidazo [4,5-b]pyridine derivatives and their use for the treatment of cancer |
CN102245610B (zh) * | 2008-10-08 | 2014-04-30 | 百时美施贵宝公司 | 吡咯并三嗪激酶抑制剂 |
WO2010068806A1 (en) * | 2008-12-10 | 2010-06-17 | Cgi Pharmaceuticals, Inc. | Amide derivatives as btk inhibitors in the treatment of allergic, autoimmune and inflammatory disorders as well as cancer |
KR20140015162A (ko) * | 2010-01-12 | 2014-02-06 | 에프. 호프만-라 로슈 아게 | 트라이사이클릭 헤테로사이클릭 화합물, 조성물 및 이의 사용 방법 |
SG190839A1 (en) * | 2010-11-19 | 2013-07-31 | Incyte Corp | Cyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as jak inhibitors |
US9328099B2 (en) * | 2011-09-22 | 2016-05-03 | Merck Sharp & Dohme Corp. | Cyanomethylpyrazole carboxamides as janus kinase inhibitors |
GB201401086D0 (en) * | 2014-01-23 | 2014-03-12 | Galapagos Nv | Novel compounds and pharmaceutical compositions thereof for the treatment of inflammatory disorders |
AU2015335788B2 (en) * | 2014-10-22 | 2020-07-30 | Dana-Farber Cancer Institute, Inc. | Thiazolyl-containing compounds for treating proliferative diseases |
AR105400A1 (es) * | 2015-08-04 | 2017-09-27 | Lilly Co Eli | Inhibidores de jak1 |
-
2017
- 2017-07-10 NZ NZ748942A patent/NZ748942A/en unknown
- 2017-07-10 CN CN201780043606.5A patent/CN109476643B/zh active Active
- 2017-07-10 CA CA3030697A patent/CA3030697C/en active Active
- 2017-07-10 MX MX2019000542A patent/MX2019000542A/es unknown
- 2017-07-10 BR BR112018075086-7A patent/BR112018075086B1/pt active IP Right Grant
- 2017-07-10 HU HUE17740885A patent/HUE054912T2/hu unknown
- 2017-07-10 EA EA201892698A patent/EA038129B1/ru not_active IP Right Cessation
- 2017-07-10 WO PCT/US2017/041388 patent/WO2018013486A1/en active Application Filing
- 2017-07-10 LT LTEP17740885.3T patent/LT3484875T/lt unknown
- 2017-07-10 KR KR1020197000782A patent/KR102225840B1/ko active IP Right Grant
- 2017-07-10 RS RS20210756A patent/RS61991B1/sr unknown
- 2017-07-10 US US15/775,990 patent/US10323019B2/en active Active
- 2017-07-10 ES ES17740885T patent/ES2877198T3/es active Active
- 2017-07-10 JP JP2018567741A patent/JP6712331B2/ja active Active
- 2017-07-10 EP EP17740885.3A patent/EP3484875B1/en active Active
- 2017-07-10 PL PL17740885T patent/PL3484875T3/pl unknown
- 2017-07-10 AU AU2017296026A patent/AU2017296026B2/en active Active
- 2017-07-10 DK DK17740885.3T patent/DK3484875T3/da active
- 2017-07-10 SI SI201730827T patent/SI3484875T1/sl unknown
- 2017-07-10 PT PT177408853T patent/PT3484875T/pt unknown
-
2019
- 2019-02-12 US US16/273,706 patent/US10344018B2/en active Active
-
2021
- 2021-06-17 HR HRP20210965TT patent/HRP20210965T1/hr unknown
- 2021-07-02 CY CY20211100588T patent/CY1124308T1/el unknown
Also Published As
Publication number | Publication date |
---|---|
AU2017296026A1 (en) | 2018-12-20 |
CA3030697C (en) | 2021-02-23 |
DK3484875T3 (da) | 2021-06-28 |
CN109476643A (zh) | 2019-03-15 |
HUE054912T2 (hu) | 2021-10-28 |
KR102225840B1 (ko) | 2021-03-11 |
CN109476643B (zh) | 2021-06-08 |
MX2019000542A (es) | 2019-07-04 |
US10344018B2 (en) | 2019-07-09 |
EA038129B1 (ru) | 2021-07-09 |
JP2019525908A (ja) | 2019-09-12 |
CY1124308T1 (el) | 2022-07-22 |
KR20190015561A (ko) | 2019-02-13 |
BR112018075086B1 (pt) | 2024-02-27 |
EA201892698A1 (ru) | 2019-06-28 |
LT3484875T (lt) | 2021-07-26 |
PL3484875T3 (pl) | 2021-11-02 |
JP6712331B2 (ja) | 2020-06-17 |
WO2018013486A1 (en) | 2018-01-18 |
AU2017296026B2 (en) | 2019-11-21 |
EP3484875B1 (en) | 2021-04-07 |
PT3484875T (pt) | 2021-07-05 |
US20180325873A1 (en) | 2018-11-15 |
CA3030697A1 (en) | 2018-01-18 |
US20190177300A1 (en) | 2019-06-13 |
RS61991B1 (sr) | 2021-07-30 |
ES2877198T3 (es) | 2021-11-16 |
US10323019B2 (en) | 2019-06-18 |
EP3484875A1 (en) | 2019-05-22 |
BR112018075086A2 (pt) | 2019-03-12 |
SI3484875T1 (sl) | 2021-08-31 |
NZ748942A (en) | 2020-08-28 |
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