HRP20211352T1 - Mono- ili di-supstituirani derivati indola kao inhibitori replikacije denga virusa - Google Patents
Mono- ili di-supstituirani derivati indola kao inhibitori replikacije denga virusa Download PDFInfo
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- HRP20211352T1 HRP20211352T1 HRP20211352TT HRP20211352T HRP20211352T1 HR P20211352 T1 HRP20211352 T1 HR P20211352T1 HR P20211352T T HRP20211352T T HR P20211352TT HR P20211352 T HRP20211352 T HR P20211352T HR P20211352 T1 HRP20211352 T1 HR P20211352T1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Claims (11)
1. Spoj s formulom (I)
[image]
njegov stereo-izomerni oblik, njegova farmaceutski prihvatljiva sol, solvat ili polimorf ; navedeni spoj je odabran iz skupine pri čemu:
R1 je H, R2 je F, Cl ili OCH3 i R3 je H;
R1 je H, R2 je F ili Cl i R3 je CH3;
R1 je CH3, R2 je OCH3 i R3 je H;
R1 je F, R2 je F i R3 je H;
R1 je CH3, R2 je F i R3 je H;
R1 je CF3 ili OCF3 i R2 je H i R3 je H;
R1 je OCF3, R2 je OCH3 i R3 je H ili
R1 je OCF3 , R2 je H i R3 je CH3.
2. Spoj ili njegov stereo-izomerni oblik, njegova farmaceutski prihvatljiva sol, solvat ili polimorf prema patentnom zahtjevu 1 naznačen time što je navedeni spoj odabran iz skupine:
[image]
[image]
[image]
[image]
3. Farmaceutski pripravak naznačen time što sadrži spoj s formulom (I) ili stereoizomerni oblik, njegovu farmaceutski prihvatljivu sol, solvat ili polimorf prema patentnom zahtjevu 1 ili 2 zajedno s jednim ili više farmaceutski prihvatljivih pomoćnih sastojaka, razrjeđivača ili nosača.
4. Spoj s formulom (I) ili stereoizomerni oblik, njegova farmaceutski prihvatljiva sol, solvat ili polimorf prema patentnom zahtjevu 1 ili farmaceutski pripravak prema patentnom zahtjevu 3 za upotrebu kao lijek.
5. Spoj s formulom (I) ili stereoizomerni oblik, njegova farmaceutski prihvatljiva sol, solvat ili polimorf prema patentnom zahtjevu 1 ili farmaceutski pripravak prema patentnom zahtjevu 3 za upotrebu za liječenje denga groznice.
6. Spoj predstavljen sljedećom strukturnom formulom (I)
[image]
njegov stereo-izomerni oblik, njegova farmaceutski prihvatljiva sol, solvat ili polimorf ; navedeni spoj je odabran iz skupine pri čemu:
R1 je H, R2 je F, Cl ili OCH3 i R3 je H;
R1 je H, R2 je F ili Cl i R3 je CH3;
R1 je CH3, R2 je OCH3 i R3 je H;
R1 je F, R2 je F i R3 je H;
R1 je CH3, R2 je F i R3 je H;
R1 je CF3 ili OCF3 i R2 je H i R3 je H;
R1 je OCF3, R2 je OCH3 i R3 je H ili
R1 je OCF3 , R2 je H i R3 je CH3
za uporabu u inhibiranju replikacije denga virusa u biološkom uzorku ili pacijentu.
7. Spoj za uporabu spoja prema patentnom zahtjevu 6 naznačen time što dalje obuhvaća istodobnu primjenu dodatnog terapijskog sredstva.
8. Spoj za uporabu prema patentnom zahtjevu 7 naznačen time što je navedeno dodatno terapijsko sredstvo još jedno antivirusno sredstvo.
9. Postupak sinteze spojeva formule (I) prema zahtjevu 1 ili 2 naznačen time što obuhvaća korake:
a) pretvaranje 2-(4-klor-2-(2-hidroksietoksi)fenil)octene kiseline s općom formulom (II) u derivat kiselog klorida s općom formulom (III) s klorirajućim reagensom, pri čemu je PG zaštitna skupina;
b) Friedel-Craftsovu reakciju kiselog klorida s općom formulom (III) sa supstituiranim indolom s općom formulom (IV) izvedenu uporabom reagensa Lewisove kiseline u prikladnom otapalu i pod prikladnim reakcijskim uvjetima koji obično uključuju hlađenje, da se dobije 3-acilirani indol s općom formulom (V), pri čemu R1, R2 i R3 imaju isto značenje kao u zahtjevu 1;
c) uklanjanje zaštitne skupine PG iz spojeva s općom formulom (V) da se dobiju spojevi s općom formulom (VI);
d) bromiranje (VI) s reagensom u prikladnom otapalu da se dobiju spojevi s općom formulom (VII);
e) reakciju spojeva s općom formulom (VII) s 3-metoksi-5-(metil-sulfonil)anilinom (VIII) u prikladnom otapalu i po izboru upotrebom baze da se dobiju spojevi s općom formulom I kao racemične smjese;
f) kiralno razdvajanje spojeva s općom formulom I radi dobivanja enantiomera A i B s općom formulom I
[image]
10. Postupak prema patentnom zahtjevu 9, naznačen time što se međuprodukti s općom formulom (V) pretvaraju u spojeve s općom formulom I slijedeći korake:
i) bromiranje na alfa položaju karbonilne funkcije međuprodukata s općom formulom (V) s prikladnim reagensom za bromiranje u prikladnom otapalu da se dobiju spojevi s općom formulom (IX), pri čemu PG je kako je definirano u zahtjevu 10 i R1, R2 i R3 imaju isto značenje kao u zahtjevu 1;
ii) reakciju spojeva s općom formulom (IX) s 3-metoksi-5-(metilsulfonil)anilinom (VIII) u prikladnom otapalu i po izboru korištenje baze da se dobiju spojevi s općom formulom (X);
iii) uklanjanje O-zaštitne skupine iz spojeva s općom formulom (X) u prikladnom otapalu radi dobivanja spojeva s općom formulom I kao racemičnih smjesa;
iv) kiralno razdvajanje spojeva s općom formulom I radi dobivanja enantiomera A i B s općom formulom I
[image]
11. Postupak sinteze spojeva formule (I) prema zahtjevu 1 ili 2 naznačen time što obuhvaća korake:
I) kondenzaciju 2-(2-(benziloksi)-etoksi)-4-klorobenzaldehida (XI) s 3-metoksi-5-(metilsulfonil)anilinom (VIII) ) u prikladnom otapalu da se dobije međuprodukt imin (XII);
II) dodavanje supstituiranog N-Boc-zaštićenog indol-karboksaldehida s općom formulom (XIII), u prisutnosti Umpolung katalizatora daje spojeve s općom formulom (X);
III) uklanjanje O-zaštitne skupine (PG) iz spojeva s općom formulom (X) u prikladnom otapalu radi dobivanja spojeva s općom formulom I kao racemičnih smjesa;
IV) kiralno razdvajanje spojeva s općom formulom I radi dobivanja enantiomera A i B s općom formulom I
[image]
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15185523 | 2015-09-16 | ||
| EP16163472 | 2016-04-01 | ||
| EP16766010.9A EP3350162B1 (en) | 2015-09-16 | 2016-09-15 | Mono- or di-substituted indole derivatives as dengue viral replication inhibitors |
| PCT/EP2016/071845 WO2017046255A1 (en) | 2015-09-16 | 2016-09-15 | Mono- or di-substituted indole derivatives as dengue viral replication inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20211352T1 true HRP20211352T1 (hr) | 2022-02-04 |
Family
ID=56926217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20211352TT HRP20211352T1 (hr) | 2015-09-16 | 2016-09-15 | Mono- ili di-supstituirani derivati indola kao inhibitori replikacije denga virusa |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US10765662B2 (hr) |
| EP (1) | EP3350162B1 (hr) |
| JP (2) | JP7050666B2 (hr) |
| KR (1) | KR102646174B1 (hr) |
| CN (1) | CN108473422B (hr) |
| AU (1) | AU2016324982B2 (hr) |
| CA (1) | CA2996979C (hr) |
| CL (1) | CL2018000696A1 (hr) |
| CO (1) | CO2018003471A2 (hr) |
| CR (1) | CR20180213A (hr) |
| DK (1) | DK3350162T3 (hr) |
| EA (1) | EA035663B1 (hr) |
| EC (1) | ECSP18020055A (hr) |
| ES (1) | ES2893298T3 (hr) |
| HK (1) | HK1257842A1 (hr) |
| HR (1) | HRP20211352T1 (hr) |
| HU (1) | HUE055870T2 (hr) |
| IL (1) | IL258043B (hr) |
| JO (1) | JOP20160198B1 (hr) |
| LT (1) | LT3350162T (hr) |
| MA (1) | MA42810A (hr) |
| MX (1) | MX381633B (hr) |
| NI (1) | NI201800039A (hr) |
| PE (1) | PE20181165A1 (hr) |
| PH (1) | PH12018500576A1 (hr) |
| SI (1) | SI3350162T1 (hr) |
| TW (1) | TWI758255B (hr) |
| UA (1) | UA122973C2 (hr) |
| UY (1) | UY36903A (hr) |
| WO (1) | WO2017046255A1 (hr) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201116559D0 (en) | 2011-09-26 | 2011-11-09 | Univ Leuven Kath | Novel viral replication inhibitors |
| GB201305376D0 (en) | 2013-03-25 | 2013-05-08 | Univ Leuven Kath | Novel viral replication inhibitors |
| JOP20160086B1 (ar) | 2015-05-08 | 2021-08-17 | 2 Katholieke Univ Leuven Ku Leuven Research And Development | مشتقات اندول مستبدلة احاديا او ثنائيا بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| JO3633B1 (ar) | 2015-09-16 | 2020-08-27 | Katholieke Univ Leuven Ku Leuven Research & Development | مشتقات اندول مستبدلة احاديا او ثنائيا بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| CN113636978B (zh) | 2015-12-16 | 2024-10-29 | 洛克索肿瘤学股份有限公司 | 可用作激酶抑制剂的化合物 |
| CA3013405A1 (en) | 2016-03-31 | 2017-10-05 | Janssen Pharmaceuticals, Inc. | Substituted indole derivatives as dengue viral replication inhibitors |
| ES2923771T3 (es) | 2016-03-31 | 2022-09-30 | Janssen Pharmaceuticals Inc | Derivados de indolina sustituidos como inhibidores de la replicación vírica de dengue |
| MA44502A (fr) * | 2016-04-01 | 2019-02-06 | Janssen Pharmaceuticals Inc | Dérivés d'indole substitués utilisés en tant qu'inhibiteurs de réplication du virus de la dengue |
| JOP20170069B1 (ar) | 2016-04-01 | 2021-08-17 | 1 Janssen Pharmaceuticals Inc | مشتقات اندولين مستبدلة بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| JOP20180026A1 (ar) * | 2017-03-31 | 2019-01-30 | Univ Leuven Kath | مشتقات اندولين مستبدلة بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| JOP20180025B1 (ar) * | 2017-03-31 | 2021-08-17 | Janssen Pharmaceuticals Inc | مشتقات اندولين مستبدلة بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| US11053196B2 (en) | 2017-05-22 | 2021-07-06 | Janssen Pharmaceuticals, Inc. | Substituted indoline derivatives as dengue viral replication inhibitors |
| WO2018215315A1 (en) | 2017-05-22 | 2018-11-29 | Janssen Pharmaceuticals, Inc. | Substituted indoline derivatives as dengue viral replication inhibitors |
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-
2016
- 2016-09-06 JO JOP/2016/0198A patent/JOP20160198B1/ar active
- 2016-09-13 TW TW105129689A patent/TWI758255B/zh not_active IP Right Cessation
- 2016-09-15 US US15/759,846 patent/US10765662B2/en active Active
- 2016-09-15 UA UAA201804007A patent/UA122973C2/uk unknown
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