HRP20210508T1 - Biciklički derivati piridina, pirazina i pirimidina kao inhibitori pi3k beta - Google Patents
Biciklički derivati piridina, pirazina i pirimidina kao inhibitori pi3k beta Download PDFInfo
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- HRP20210508T1 HRP20210508T1 HRP20210508TT HRP20210508T HRP20210508T1 HR P20210508 T1 HRP20210508 T1 HR P20210508T1 HR P20210508T T HRP20210508T T HR P20210508TT HR P20210508 T HRP20210508 T HR P20210508T HR P20210508 T1 HRP20210508 T1 HR P20210508T1
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- Prior art keywords
- 4alkyl
- het1
- membered saturated
- substituents
- saturated heterocyclyl
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- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 title 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 title 1
- 125000002619 bicyclic group Chemical group 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title 1
- 150000003230 pyrimidines Chemical class 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 19
- 125000000623 heterocyclic group Chemical group 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000001424 substituent group Chemical group 0.000 claims 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 10
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- 125000005843 halogen group Chemical group 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 7
- 125000005842 heteroatom Chemical group 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 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 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 5
- 150000002431 hydrogen Chemical group 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- -1 C1-4alkyloxy Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 206010052779 Transplant rejections Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000003566 oxetanyl group Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 208000004852 Lung Injury Diseases 0.000 claims 1
- 208000034486 Multi-organ failure Diseases 0.000 claims 1
- 208000010718 Multiple Organ Failure Diseases 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- 206010033645 Pancreatitis Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 206010069363 Traumatic lung injury Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 230000007815 allergy Effects 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 231100000515 lung injury Toxicity 0.000 claims 1
- 208000029744 multiple organ dysfunction syndrome Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 230000019100 sperm motility Effects 0.000 claims 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims 1
Classifications
-
- 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
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Claims (15)
1. Spoj s formulom (I)
[image]
njegov tautomer ili stereoizomerni oblik, naznačen time što
X1 predstavlja CH ili N;
X2 predstavlja CR1 ili N;
uz uvjet da maksimalno jedan od X1 i X2 predstavlja N;
R1 predstavlja vodik, -C(=O)OH, -C(=O)NH2, -NH2, -CH2OH,
[image]
Y predstavlja -CH2- ili -NH-;
R2 predstavlja
[image]
R3 predstavlja C1-4alkil; -C(=O)-O-C1-4alkil; -C(=O)-Het1; -CH(OH)-CH2-Rq; C1-4alkil supstituiran na istom ugljikovom atomu s jednim -OH i s jednim Het1; ili C1-4alkil supstituiran s jednim supstituentom odabranim iz skupine koju čine halo, -OH, -NH2, -O-(C=O)-C1-4alkil, -(C=O)-O-C1-4alkil, -NH-(C=O)-C1-4alkil, -NH-(SO2)-C1-4alkil, -N(CH3)-C1-4alkil-SO2-CH3, -NH-C1-4alkil-SO2-CH3, -N(CH3)-C1-4alkil-OH, -N(C=O-C1-4alkil)-C1-4alkil-OH, -(C=O)-NH-C1-4alkil-OH, -O-(C=O)-CH(NH2)-C1-4alkil, -O-(C=O)-CH(NH2)-C1-4alkil-Ar,
[image]
-NH-C1-4alkil-OH, Het1, -O-C(=O)-C1-4alkil-Het1, -C(=O)-Het1, i -NH-C(=O)-Het1;
Rq predstavlja Het1, halo, -OH, -NH2, -O-(C=O)-C1-4alkil, -NH-(C=O)-C1-4alkil, -NH-(SO2)-C1-4alkil, -N(CH3)-C1-4alkil-SO2-CH3, -NH-C1-4alkil-SO2-CH3, -N(CH3)-C1-4alkil-OH, -O-(C=O)-CH(NH2)-C1-4alkil, -O-(C=O)-CH(NH2)-C1-4alkil-Ar,
[image]
ili -NH-C1-4alkil-OH;
Ar predstavlja fenil po izboru supstituiran s jednim hidroksi;
R4a predstavlja vodik, C1-4alkil, Heta, ili C1-4alkil supstituiran s jednim ili više supstituenata koji su neovisno odabrani iz skupine koju čine-OH, -NR5R6 i Heta;
R4b predstavlja vodik, halo, C1-4alkil, ili C1-4alkil supstituiran s jednim ili više halogenih supstituenata;
ili R4a i R4b se uzimaju zajedno da tvore zajedno s fenilnim prstenom na koji su vezani strukturu formule (a-1), (a-2), (a-3), (a-4) ili (a-5):
[image]
[image]
X predstavlja -NH-, -O-, -N(C1-3alkil)-, ili -N(hidroksiC1-3alkil)-;
oba R7 supstituenta su isti i odabrani su iz skupine koju čine vodik, fluor i metil; ili oba R7 supstituenta se uzimaju zajedno da tvore zajedno sa zajedničkim atomom ugljika na koji su vezani ciklopropil, ciklobutil ili oksetanil;
oba R8 supstituenta su isti i odabrani su iz skupine koju čine vodik i metil; ili oba R8 supstituenta se uzimaju zajedno da tvore zajedno sa zajedničkim atomom ugljika na koji su vezani ciklopropil, ciklobutil ili oksetanil;
R5 predstavlja vodik, C1-6alkil, ili C1-6alkil supstituiran s jednim -OH;
R6 predstavlja vodik, C1-6alkil, ili C1-6alkil supstituiran s jednim -OH;
Het1 predstavlja 4-, 5- ili 6-eročlani zasićeni heterociklil koji sadrži najmanje jedan heteroatom svaki neovisno odabran od O, S, S(=O)p i N; navedeni 4-, 5- ili 6-eročlani zasićeni heterociklil je po izboru supstituiran s jednim ili dva supstituenta koji su svaki neovisno odabrani iz skupine koju čine halo, -NH2, C1-4alkil,
-S(=O)2-C1-6alkil, -C1-4alkil-S(=O)2-C1-6alkil, hidroksil, C1-4alkiloksi, fluor, cijano i C1-4alkil supstituiran s jednim hidroksi; ili dva supstituenta na istom ugljikovom atomu navedenog 4-, 5- ili 6-eročlanog zasićenog heterociklila uzimaju se zajedno da tvore zajedno sa zajedničkim ugljikovim atomom na koji su spojeni prsten A;
Prsten A predstavlja ciklobutil, ciklopentil, cikloheksil ili 4-, 5- ili 6-eročlani zasićeni heterociklil koji sadrži najmanje jedan heteroatom svaki neovisno odabran od O, S, S(=O)p i N; navedeni ciklobutil, ciklopentil, cikloheksil ili 4-, 5- ili 6-eročlani zasićeni heterociklil je po izboru supstituiran s jednim ili dva C1-4alkil supstituenta, s jednim C1-4alkilom i jednim hidroksi supstituentom, ili s jednim hidroksi supstituentom;
svaki Heta neovisno predstavlja 4-, 5- ili 6-eročlani zasićeni heterociklil koji sadrži najmanje jedan heteroatom svaki neovisno odabran od O, S, S(=O)p i N; navedeni 4-, 5- ili 6-eročlani zasićeni heterociklil je po izboru supstituiran s jednim ili dva supstituenta koji su svaki neovisno odabrani iz skupine koju čine C1-4alkil, -S(=O)2-C1-6alkil, hidroksi, -C1-4alkil-S(=O)2-C1-6alkil, i C1-4alkil supstituiran s jednim hidroksi; ili dva supstituenta na istom ugljikovom atomu navedenog 4-, 5- ili 6-eročlanog zasićenog heterociklila uzimaju se zajedno da tvore zajedno sa zajedničkim ugljikovim atomom na koji su spojeni prsten B;
Prsten B predstavlja ciklobutil, ciklopentil, cikloheksil ili 4-, 5- ili 6-eročlani zasićeni heterociklil koji sadrži najmanje jedan heteroatom svaki neovisno odabran od O, S, S(=O)p i N; navedeni ciklobutil, ciklopentil, cikloheksil ili 4-, 5- ili 6-eročlani zasićeni heterociklil je po izboru supstituiran s jednim ili dva C1-4alkil supstituenta, s jednim C1-4alkilom i jednim hidroksi supstituentom, ili s jednim hidroksi supstituentom;
p predstavlja 1 ili 2;
ili N-oksid, njegova farmaceutski prihvatljiva adicijska sol ili njegov solvat .
2. Spoj prema patentnom zahtjevu 1, naznačen time što
R3 predstavlja C1-4alkil; -C(=O)-Het1; C1-4alkil supstituiran na istom ugljikovom atomu s jednim -OH i s jednim Het1; ili C1-4alkil supstituiran s jednim supstituentom odabranim iz skupine koju čine halo, -OH, -NH2, -O-(C=O)-C1-4alkil, -(C=O)-O-C1-4alkil, -NH-(C=O)-C1-4alkil, -NH-(SO2)-C1-4alkil, -N(CH3)-C1-4alkil-SO2-CH3, -NH-C1-4alkil-SO2-CH3, -N(CH3)-C1-4alkil-OH, -N(C=O-C1-4alkil)-C1-4alkil-OH, -(C=O)-NH-C1-4alkil-OH, -O-(C=O)-CH(NH2)-C1-4alkil,
[image]
-NH-C1-4alkil-OH, Het1, -O-C(=O)-C1-4alkil-Het1, -C(=O)-Het1, i -NH-C(=O)-Het1;
svaki Heta neovisno predstavlja 4-, 5- ili 6-eročlani zasićeni heterociklil koji sadrži najmanje jedan heteroatom svaki neovisno odabran od O, S, S(=O)p i N; navedeni 4-, 5- ili 6-eročlani zasićeni heterociklil je po izboru supstituiran s jednim ili dva supstituenta koji su svaki neovisno odabrani iz skupine koju čine C1-4alkil, -S(=O)2-C1-6alkil, hidroksi, -C1-4alkil-S(=O)2-C1-6alkil, i C1-4alkil supstituiran s jednim hidroksilom.
3. Spoj prema patentnom zahtjevu 1, naznačen time što
R1 predstavlja vodik, -C(=O)OH, -C(=O)NH2, -NH2, -CH2OH,
[image]
R2 predstavlja
[image]
R3 predstavlja C1-4alkil; ili C1-4alkil supstituiran s jednim supstituentom odabranim iz skupine koju čine halo, -OH, -O-(C=O)-C1-4alkil, -(C=O)-O-C1-4alkil, -N(CH3)-C1-4alkil-OH, -N(C=O-C1-4alkil)-C1-4alkil-OH, -NH-C1-4alkil-OH, Het1, i -C(=O)-Het1;
R4a predstavlja C1-4alkil, ili Heta;
R4b predstavlja halo, ili C1-4alkil supstituiran s jednim ili više halogenih supstituenata;
Het1 predstavlja 4-, 5- ili 6-eročlani zasićeni heterociklil koji sadrži najmanje jedan heteroatom svaki neovisno odabran od S(=O)p i N; navedeni 4-, 5- ili 6-eročlani zasićeni heterociklil je po izboru supstituiran s jednim ili dva supstituenta koji su neovisno odabrani iz skupine koju čine C1-4alkil, i C1-4alkil supstituiran s jednim hidroksi; ili dva supstituenta na istom ugljikovom atomu u navedenom 4-, 5- ili 6-eročlanom zasićenom heterociklilu uzimaju se zajedno da tvore zajedno sa zajedničkim ugljikovim atomom na koji su spojeni prsten A;
prsten A predstavlja ciklobutil, ciklopentil, cikloheksil ili 4-, 5- ili 6-eročlani zasićeni heterociklil koji sadrži najmanje jedan heteroatom svaki neovisno odabran od S(=O)p i N;
svaki Heta neovisno predstavlja 4-, 5- ili 6-eročlani zasićeni heterociklil koji sadrži najmanje jedan N-atom; navedeni 4-, 5- ili 6-eročlani zasićeni heterociklil je po izboru supstituiran s jednim ili dva C1-4alkil supstituenta
p predstavlja 2.
4. Spoj prema patentnom zahtjevu 1, naznačen time što
R1 predstavlja
[image]
5. Spoj prema patentnom zahtjevu 1, naznačen time što
X2 predstavlja CH.
6. Spoj prema patentnom zahtjevu 1, naznačen time što
X1 predstavlja CH, i X2 predstavlja CR1.
7. Spoj prema patentnom zahtjevu 1, naznačen time što
X1 predstavlja CH, i X2 predstavlja N.
8. Spoj prema patentnom zahtjevu 1, naznačen time što
X1 predstavlja N, i X2 predstavlja CR1.
9. Spoj prema patentnom zahtjevu 1, naznačen time što
R2 predstavlja
[image]
10. Spoj prema patentnom zahtjevu 1, naznačen time što Y predstavlja -CH2-.
11. Farmaceutski pripravak, naznačen time što sadrži farmaceutski prihvatljivi nosač i, kao aktivni sastojak, terapeutski učinkovitu količinu spoja prema bilo kojem od patentnih zahtjeva 1 do 10.
12. Spoj kao što je definiran u bilo kojem od patentnih zahtjeva 1 do 10 naznačen time što je za uporabu kao lijek.
13. Spoj kao što je definiran u bilo kojem od patentnih zahtjeva 1 do 10 naznačen time što je za uporabu za liječenje ili sprječavanje bolesti ili stanja odabranog od raka, autoimunih poremećaja, kardiovaskularnih bolesti, upalnih bolesti, neurodegenerativnih bolesti, alergije, pankreatitisa, astme, zatajenja više organa, bolesti bubrega, agregacije trombocita, pokretljivosti sperme, odbacivanja transplantata, odbacivanja presatka i ozljeda pluća.
14. Spoj za uporabu prema patentnom zahtjevu 13 naznačen time što bolest ili stanje je rak.
15. Spoj za uporabu prema patentnom zahtjevu 14 naznačen time što bolest ili stanje je rak prostate.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP16174715 | 2016-06-16 | ||
| EP17732059.5A EP3472160B1 (en) | 2016-06-16 | 2017-06-15 | Bicyclic pyridine, pyrazine, and pyrimidine derivatives as pi3k beta inhibitors |
| PCT/EP2017/064671 WO2017216292A1 (en) | 2016-06-16 | 2017-06-15 | Bicyclic pyridine, pyrazine, and pyrimidine derivatives as pi3k beta inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20210508T1 true HRP20210508T1 (hr) | 2021-05-28 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20210508TT HRP20210508T1 (hr) | 2016-06-16 | 2021-03-30 | Biciklički derivati piridina, pirazina i pirimidina kao inhibitori pi3k beta |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US10894793B2 (hr) |
| EP (1) | EP3472160B1 (hr) |
| JP (1) | JP7149854B2 (hr) |
| KR (1) | KR102472453B1 (hr) |
| CN (1) | CN109311875A (hr) |
| AU (1) | AU2017286379B2 (hr) |
| BR (1) | BR112018075999A2 (hr) |
| CA (1) | CA3025594A1 (hr) |
| DK (1) | DK3472160T3 (hr) |
| EA (1) | EA037361B1 (hr) |
| ES (1) | ES2871140T3 (hr) |
| HR (1) | HRP20210508T1 (hr) |
| HU (1) | HUE054118T2 (hr) |
| IL (1) | IL263652A (hr) |
| LT (1) | LT3472160T (hr) |
| MX (1) | MX2018015707A (hr) |
| SI (1) | SI3472160T1 (hr) |
| WO (1) | WO2017216292A1 (hr) |
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| HUE061898T2 (hu) * | 2017-09-08 | 2023-08-28 | Beigene Ltd | Imidazo[1,5-a]pirazin-származékok mint PI3Kdelta inhibitorok |
| CN111039946A (zh) * | 2018-10-15 | 2020-04-21 | 上海轶诺药业有限公司 | 一类咪唑并芳环类化合物的制备和应用 |
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| JP2009528385A (ja) | 2006-03-02 | 2009-08-06 | スミスクライン・ビーチャム・コーポレイション | Ｐｉ３キナーゼ阻害剤として用いるためのチアゾロン |
| US20090215818A1 (en) | 2006-07-24 | 2009-08-27 | Smithkline Beecham Corporation | Thiozolidinedione derivatives as pi3 kinase inhibitors |
| JP5508027B2 (ja) | 2007-02-22 | 2014-05-28 | メルク セローノ ソシエテ アノニム | キノキサリン化合物及びその使用 |
| JP2010535804A (ja) | 2007-08-09 | 2010-11-25 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニー | Ｐｉ３キナーゼ阻害薬としてのキノキサリン誘導体 |
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| US9096605B2 (en) | 2011-08-24 | 2015-08-04 | Glaxosmithkline Llc | Pyrazolopyrimidine derivatives as PI3 kinase inhibitors |
| US8778937B2 (en) | 2011-12-20 | 2014-07-15 | Glaxosmithkline Llc | Benzimidazole boronic acid derivatives as PI3 kinase inhibitors |
| US8906910B2 (en) * | 2011-12-20 | 2014-12-09 | Glaxosmithkline Llc | Imidazopyridine derivatives as PI3 kinase |
| WO2014009295A1 (en) | 2012-07-13 | 2014-01-16 | Ucb Pharma S.A. | Imidazopyridine derivatives as modulators of tnf activity |
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-
2017
- 2017-06-15 SI SI201730708T patent/SI3472160T1/sl unknown
- 2017-06-15 JP JP2018564783A patent/JP7149854B2/ja active Active
- 2017-06-15 HU HUE17732059A patent/HUE054118T2/hu unknown
- 2017-06-15 LT LTEP17732059.5T patent/LT3472160T/lt unknown
- 2017-06-15 KR KR1020187035198A patent/KR102472453B1/ko active IP Right Grant
- 2017-06-15 WO PCT/EP2017/064671 patent/WO2017216292A1/en unknown
- 2017-06-15 MX MX2018015707A patent/MX2018015707A/es active IP Right Grant
- 2017-06-15 ES ES17732059T patent/ES2871140T3/es active Active
- 2017-06-15 CN CN201780037269.9A patent/CN109311875A/zh active Pending
- 2017-06-15 US US16/309,999 patent/US10894793B2/en active Active
- 2017-06-15 AU AU2017286379A patent/AU2017286379B2/en active Active
- 2017-06-15 BR BR112018075999A patent/BR112018075999A2/pt unknown
- 2017-06-15 DK DK17732059.5T patent/DK3472160T3/da active
- 2017-06-15 EP EP17732059.5A patent/EP3472160B1/en active Active
- 2017-06-15 CA CA3025594A patent/CA3025594A1/en active Pending
- 2017-06-15 EA EA201990046A patent/EA037361B1/ru not_active IP Right Cessation
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- 2018-12-11 IL IL263652A patent/IL263652A/en active IP Right Grant
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Also Published As
| Publication number | Publication date |
|---|---|
| CN109311875A (zh) | 2019-02-05 |
| BR112018075999A2 (pt) | 2019-04-02 |
| ES2871140T3 (es) | 2021-10-28 |
| MX2018015707A (es) | 2019-03-21 |
| HUE054118T2 (hu) | 2021-08-30 |
| IL263652A (en) | 2019-01-31 |
| JP2019518032A (ja) | 2019-06-27 |
| AU2017286379A1 (en) | 2018-12-06 |
| CA3025594A1 (en) | 2017-12-21 |
| LT3472160T (lt) | 2021-04-26 |
| EP3472160A1 (en) | 2019-04-24 |
| US10894793B2 (en) | 2021-01-19 |
| EA037361B1 (ru) | 2021-03-18 |
| US20190169199A1 (en) | 2019-06-06 |
| DK3472160T3 (da) | 2021-05-10 |
| EP3472160B1 (en) | 2021-02-24 |
| SI3472160T1 (sl) | 2021-07-30 |
| JP7149854B2 (ja) | 2022-10-07 |
| KR102472453B1 (ko) | 2022-11-29 |
| AU2017286379B2 (en) | 2021-07-01 |
| EA201990046A1 (ru) | 2019-05-31 |
| KR20190016954A (ko) | 2019-02-19 |
| WO2017216292A1 (en) | 2017-12-21 |
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