HRP20221289T1 - Supstituirani alkoksipiridinil indolsulfonamidi - Google Patents
Supstituirani alkoksipiridinil indolsulfonamidi Download PDFInfo
- Publication number
- HRP20221289T1 HRP20221289T1 HRP20221289TT HRP20221289T HRP20221289T1 HR P20221289 T1 HRP20221289 T1 HR P20221289T1 HR P20221289T T HRP20221289T T HR P20221289TT HR P20221289 T HRP20221289 T HR P20221289T HR P20221289 T1 HRP20221289 T1 HR P20221289T1
- Authority
- HR
- Croatia
- Prior art keywords
- sulfonamide
- indole
- fluoro
- chloro
- compound according
- Prior art date
Links
- 150000005248 indolsulfonamides Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 20
- -1 chloro, cyclopropyl Chemical group 0.000 claims 17
- 229910052731 fluorine Inorganic materials 0.000 claims 11
- 239000011737 fluorine Substances 0.000 claims 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 125000001153 fluoro group Chemical group F* 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- 239000000460 chlorine Substances 0.000 claims 6
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims 5
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 239000013078 crystal Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- POIMTPYVVVXCTL-UHFFFAOYSA-N 6-chloro-7-cyclopropyloxy-N-[3,6-difluoro-5-(2-fluoroethoxy)pyridin-2-yl]-1H-indole-3-sulfonamide Chemical compound ClC1=CC=C2C(=CNC2=C1OC1CC1)S(=O)(=O)NC1=NC(=C(C=C1F)OCCF)F POIMTPYVVVXCTL-UHFFFAOYSA-N 0.000 claims 1
- DEEFSKOIKOVAJK-UHFFFAOYSA-N 6-chloro-N-[5-[2-(difluoromethoxy)ethoxy]-3-fluoro-6-methoxypyridin-2-yl]-7-fluoro-1H-indole-3-sulfonamide Chemical compound ClC1=CC=C2C(=CNC2=C1F)S(=O)(=O)NC1=NC(=C(C=C1F)OCCOC(F)F)OC DEEFSKOIKOVAJK-UHFFFAOYSA-N 0.000 claims 1
- 208000016192 Demyelinating disease Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Claims (17)
1. Spoj koji ima formulu I
[image]
naznačen time što
R6 je odabran od klora, fluora, fluorometil i fluorometoksi,
R7 je odabran od fluora, klora, ciklopropila, ciklopropiloksi, fluorometila, i fluorometoksi,
R8 je fluor ili metoksi,
R11 je vodik, fluor ili metoksi,
L je veza, ili poveznica odabrana od -CH2- i -CH2-CH2-O- ,
X1 i X2 su neovisno odabrani od vodika i fluora,
i njihove farmaceutski prihvatljive soli, solvati, izotopi i kokristali.
2. Spoj prema zahtjevu 1, naznačen time što R6 je klor.
3. Spoj prema zahtjevu 1, naznačen time što R6 je fluorometil, poželjno difluorometil.
4. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time što je R7 odabran od fluorometila, ciklopropiloksi, fluora i klora.
5. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time što X1 je vodik.
6. Spoj prema patentnim zahtjevima 1 do 5, naznačen time što R8 je fluor i pri čemu je L odabran od (a) veze (b) -CH2- i (c) -CH2-CH2-O-, takav spoj stoga ima strukturu prema formulama IIa, IIb ili IIc,
[image]
pri čemu su svi ostali supstituenti kao što je opisano u zahtjevima 1 do 5.
7. Spoj prema zahtjevu 6,
naznačen time što
R6 je odabran od klora i fluorometila, poželjno od klora i difluorometila,
R7 je odabran od fluora, klora, ciklopropila, ciklopropiloksi, fluorometila i fluorometoksi,
R11 je odabran od vodika, metoksi i fluora,
X1 i X2 su neovisno odabrani od vodika i fluora.
8. Spoj prema bilo kojem od patentnih zahtjeva 1 do 5, naznačen time što R8 i R11 su oba fluor i pri čemu je L odabran od (a) veze (b) -CH2- i (c) -CH2-CH2-O-, takav spoj stoga ima strukturu prema formuli IIIa, IIIb, ili IIIc,
[image]
pri čemu su svi ostali supstituenti kao što je opisano u zahtjevima 1 do 5.
9. Spoj prema bilo kojem od patentnih zahtjeva 1 do 5, naznačen time što, R11 je metoksi i pri čemu je L odabran od (a) veze (b) -CH2- i (c) -CH2-CH2-O-, takav spoj stoga ima strukturu prema formuli Va, Vb ili Vc:
[image]
pri čemu su svi ostali supstituenti kao što je ranije opisano.
10. Spoj prema zahtjevu 9, naznačen time što
R6 je odabran od fluora, klora, fluorometila i fluorometoksi,
R7 je odabran od fluora, klora, ciklopropila, ciklopropiloksi, fluorometila, i fluorometoksi,
R8 je fluor, i
X1 i X2 su neovisno odabrani od vodika i fluora.
11. Spoj prema bilo kojem od patentnih zahtjeva 1, 4 i 6 do 10, naznačen time što
R6 i R7 su neovisno odabrani od klora i difluorometila
i pri čemu X1 je vodik, i X2 je vodik ili fluor.
12. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time što X1 je vodik i X2 je fluor.
13. Spoj prema zahtjevu 1, naznačen time što je odabran iz niza koji sadrži:
6,7-diklor-N-[5-(2,2-difluoretoksi)-3-metoksipiridin-2-il]-1H-indol-3-sulfonamid
7-klor-N-[5-(2,2-difluoretoksi)-3-fluor-6-metoksipiridin-2-il]-6-(difluorometil)-1H-indol-3-sulfonamid
6-klor-N-[5-[2-(difluorometoksi)etoksi]-3-fluor-6-metoksipiridin-2-il]-7-fluor-1H-indol-3-sulfonamid
6-klor-N-[5-(2,2-difluoretoksi)-3-fluor-6-metoksipiridin-2-il]-7-fluor-1H-indol-3-sulfonamid
N-[5-(2,2-difluoretoksi)-3-fluorpiridin-2-il]-6-(difluorometil)-7-fluor-1H-indol-3-sulfonamid
6-klor-N-[3,6-difluor-5-(2-fluoretoksi)piridin-2-il]-7-(trifluorometoksi)-1H-indol-3-sulfonamid
6-klor-N-[5-(difluorometoksi)-3-metoksipiridin-2-il]-7-(difluorometil)-1H-indol-3-sulfonamid
6,7-diklor-N-[5-(difluorometoksi)-3-metoksipiridin-2-il]-1H-indol-3-sulfonamid
6-klor-N-[5-(2,2-difluoretoksi)-3-fluor-6-metoksipiridin-2-il]-7-(difluorometil)-1H-indol-3-sulfonamid
6-klor-N-[5-(2,2-difluoretoksi)-3-fluorpiridin-2-il]-7-(difluorometil)-1H-indol-3-sulfonamid
7-klor-N-[3-fluor-5-(2-fluoretoksi)piridin-2-il]-6-(difluorometil)-1H-indol-3-sulfonamid
6-(difluorometil)-7-fluor-N-[3-fluor-5-(2-fluoretoksi)piridin-2-il]-1H-indol-3-sulfonamid
6-klor-7-(difluorometil)-N-[3-fluor-5-(2-fluoretoksi)piridin-2-il]-1H-indol-3-sulfonamid
6,7-diklor-N-[5-(2,2-difluoretoksi)-3-fluorpiridin-2-il]-1H-indol-3-sulfonamid 6,7-diklor-N-[3-fluor-5-(2-fluoretoksi)piridin-2-il]-1H-indol-3-sulfonamid 6-klor-N-[3,6-difluor-5-(2-fluoretoksi)piridin-2-il]-7-fluor-1H-indol-3-sulfonamid
6-klor-N-[5-(2,2-difluoretoksi)-3,6-difluorpiridin-2-il]-7-fluor-1H-indol-3-sulfonamid
6-klor-7-ciklopropil-N-[3,6-difluor-5-(2-fluoretoksi)piridin-2-il]-1H-indol-3-sulfonamid
6-klor-N-[3,6-difluor-5-(2-fluoretoksi)piridin-2-il]-7-(difluorometil)-1H-indol-3-sulfonamid
6-klor-7-ciklopropiloksi-N-[3,6-difluor-5-(2-fluoretoksi)piridin-2-il]-1H-indol-3-sulfonamid,
i njihove farmaceutski prihvatljive soli, solvati, izotopi i kokristali.
14. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time što se koristi u terapiji.
15. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time što je za upotrebu u liječenju ili ublažavanju poremećaja demijelinizacije.
16. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time što se koristi u liječenju ili ublažavanju multiple skleroze.
17. Terapeutski pripravak, naznačen time što sadrži spoj prema bilo kojem od prethodnih zahtjeva i farmaceutski prihvatljiv nosač.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP18178773.0A EP3584244A1 (en) | 2018-06-20 | 2018-06-20 | Substituted alkoxypyridinyl indolsulfonamides |
| EP19731283.8A EP3810587B1 (en) | 2018-06-20 | 2019-06-19 | Substituted alkoxypyridinyl indolsulfonamides |
| PCT/EP2019/066148 WO2019243398A1 (en) | 2018-06-20 | 2019-06-19 | Substituted alkoxypyridinyl indolsulfonamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20221289T1 true HRP20221289T1 (hr) | 2022-12-23 |
Family
ID=62715911
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20221289TT HRP20221289T1 (hr) | 2018-06-20 | 2019-06-19 | Supstituirani alkoksipiridinil indolsulfonamidi |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US11976056B2 (hr) |
| EP (3) | EP3584244A1 (hr) |
| JP (1) | JP7371031B2 (hr) |
| CN (1) | CN112292375B (hr) |
| CA (1) | CA3101086A1 (hr) |
| DK (1) | DK3810587T3 (hr) |
| ES (1) | ES2929829T3 (hr) |
| HR (1) | HRP20221289T1 (hr) |
| HU (1) | HUE060181T2 (hr) |
| LT (1) | LT3810587T (hr) |
| MX (1) | MX2020012823A (hr) |
| PL (1) | PL3810587T3 (hr) |
| PT (1) | PT3810587T (hr) |
| WO (1) | WO2019243398A1 (hr) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3983384B1 (en) * | 2019-06-17 | 2023-10-11 | UCB Pharma GmbH | N-(phenyl)-indole-3-sulfonamide derivatives and related compounds as gpr17 modulators for treating cns disorders such as multiple sclerosis |
| CN112375027B (zh) * | 2020-12-07 | 2023-03-31 | 中国药科大学 | 吲哚磺酰胺类衍生物及其医药用途 |
| JP2024507176A (ja) * | 2021-02-26 | 2024-02-16 | エフ． ホフマン－ラ ロシュ アーゲー | 新規なピリミジン－２－イルスルホンアミド誘導体 |
| WO2023241960A1 (en) * | 2022-06-15 | 2023-12-21 | Basf Se | A process for the photolytic chlorination of 3-halopyridine with molecular chlorine |
| EP4311828A1 (en) * | 2022-07-26 | 2024-01-31 | Basf Se | A process for the photolytic chlorination of 3-halopyridine with molecular chlorine |
| WO2024017863A1 (en) * | 2022-07-20 | 2024-01-25 | F. Hoffmann-La Roche Ag | Novel pyrimidinyl and triazinyl sulfonamide derivatives |
| WO2024017855A1 (en) * | 2022-07-20 | 2024-01-25 | F. Hoffmann-La Roche Ag | Novel isothiazol-3-yl and isoxazol-3-yl sulfonamide compounds |
| WO2024017856A1 (en) | 2022-07-20 | 2024-01-25 | F. Hoffmann-La Roche Ag | Novel isoquinolinone, pyrrolopyridinone and thienopyridinone sulfonamide derivatives |
| WO2024017858A1 (en) * | 2022-07-20 | 2024-01-25 | F. Hoffmann-La Roche Ag | Novel naphthyl and isoquinoline sulfonamide derivatives |
| WO2024017857A1 (en) | 2022-07-20 | 2024-01-25 | F. Hoffmann-La Roche Ag | Novel imidazopyridine and pyrazolopyridine sulfonamide derivatives |
| WO2024023128A1 (en) * | 2022-07-28 | 2024-02-01 | F. Hoffmann-La Roche Ag | Novel 7-substituted indole sulfonamide derivatives |
| WO2024023129A1 (en) * | 2022-07-28 | 2024-02-01 | F. Hoffmann-La Roche Ag | Novel 7-substituted indole sulfonamide derivatives |
| WO2024042147A2 (en) * | 2022-08-26 | 2024-02-29 | F. Hoffmann-La Roche Ag | Novel deuterated pyrimidin-2-yl sulfonamide derivatives |
| WO2024115733A1 (en) * | 2022-12-02 | 2024-06-06 | Rewind Therapeutics Nv | Fused pyrrolyl-sulfonamide compounds |
| WO2024153233A1 (en) * | 2023-01-19 | 2024-07-25 | Nanjing Immunophage Biotech Co., Ltd | Compounds and their uses as gpr17 antagonists |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19814084B4 (de) | 1998-03-30 | 2005-12-22 | Lts Lohmann Therapie-Systeme Ag | D2-Agonist enthaltendes transdermales therapeutisches System zur Behandlung des Parkinson-Syndroms und Verfahren zu seiner Herstellung |
| SE9904750D0 (sv) | 1999-12-23 | 1999-12-23 | Pharmacia & Upjohn Ab | New formulation, use and method |
| WO2005103291A1 (ja) | 2004-04-27 | 2005-11-03 | Takeda Pharmaceutical Company Limited | Ｇタンパク質共役型レセプタータンパク質の新規リガンドとその用途 |
| ITMI20042007A1 (it) | 2004-10-21 | 2005-01-21 | Consiglio Nazionale Ricerche | "modulatori del ricettore gpr17 e loro impieghi terapeutici" |
| CA2633588A1 (en) | 2005-12-20 | 2007-08-23 | Teikoku Pharma Usa, Inc. | Methods of transdermally administering an indole serotonin receptor agonist and transdermal compositions for use in the same |
| WO2009000262A1 (de) | 2007-06-25 | 2008-12-31 | Acino Ag | Elektrophoretisches transdermales applikationssystem |
| EP2355826A1 (en) * | 2008-11-07 | 2011-08-17 | The Cleveland Clinic Foundation | Compounds and methods of promoting oligodendrocyte precursor differentiation |
| WO2011113032A2 (en) | 2010-03-11 | 2011-09-15 | Swinford Jerry L | Method and apparatus for washing dowhole tubulars and equipment |
| EP2567698B1 (en) * | 2011-09-07 | 2014-02-12 | Rheinische Friedrich-Wilhelms-Universität Bonn | GPR 17 agonists and screening assay |
| JP6082457B2 (ja) | 2012-05-09 | 2017-02-15 | ウニヴェルスィタ デッリ ストゥディ ディ ミラノ | Ｇｐｒ１７受容体調節因子 |
| EP3515426A1 (en) | 2016-09-24 | 2019-07-31 | Washington University | INHIBITORS OF SARM1 NADase ACTIVITY AND USES THEREOF |
| TWI754702B (zh) * | 2016-12-28 | 2022-02-11 | 德商Ｕｃｂ製藥有限公司 | （氮雜）吲哚－和苯並呋喃－３－磺醯胺類 |
-
2018
- 2018-06-20 EP EP18178773.0A patent/EP3584244A1/en not_active Ceased
-
2019
- 2019-06-19 PL PL19731283.8T patent/PL3810587T3/pl unknown
- 2019-06-19 CA CA3101086A patent/CA3101086A1/en active Pending
- 2019-06-19 DK DK19731283.8T patent/DK3810587T3/da active
- 2019-06-19 LT LTEPPCT/EP2019/066148T patent/LT3810587T/lt unknown
- 2019-06-19 ES ES19731283T patent/ES2929829T3/es active Active
- 2019-06-19 WO PCT/EP2019/066148 patent/WO2019243398A1/en unknown
- 2019-06-19 HU HUE19731283A patent/HUE060181T2/hu unknown
- 2019-06-19 EP EP22174561.5A patent/EP4086248A1/en not_active Withdrawn
- 2019-06-19 HR HRP20221289TT patent/HRP20221289T1/hr unknown
- 2019-06-19 US US17/058,567 patent/US11976056B2/en active Active
- 2019-06-19 JP JP2020570978A patent/JP7371031B2/ja active Active
- 2019-06-19 EP EP19731283.8A patent/EP3810587B1/en active Active
- 2019-06-19 PT PT197312838T patent/PT3810587T/pt unknown
- 2019-06-19 CN CN201980039867.9A patent/CN112292375B/zh active Active
- 2019-06-19 MX MX2020012823A patent/MX2020012823A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US11976056B2 (en) | 2024-05-07 |
| WO2019243398A1 (en) | 2019-12-26 |
| EP3810587A1 (en) | 2021-04-28 |
| JP7371031B2 (ja) | 2023-10-30 |
| PL3810587T3 (pl) | 2023-02-06 |
| EP3584244A1 (en) | 2019-12-25 |
| LT3810587T (lt) | 2022-11-25 |
| EP3810587B1 (en) | 2022-08-10 |
| ES2929829T3 (es) | 2022-12-01 |
| HUE060181T2 (hu) | 2023-02-28 |
| EP4086248A1 (en) | 2022-11-09 |
| JP2021527696A (ja) | 2021-10-14 |
| CN112292375B (zh) | 2023-12-05 |
| DK3810587T3 (da) | 2022-10-31 |
| PT3810587T (pt) | 2022-11-14 |
| CA3101086A1 (en) | 2019-12-26 |
| MX2020012823A (es) | 2021-02-15 |
| CN112292375A (zh) | 2021-01-29 |
| US20210214337A1 (en) | 2021-07-15 |
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