DK3019482T3 - Trisubstituerede benzoetriazolderivater som dihydrooro-tatoxygenaseinhibitorer - Google Patents
Trisubstituerede benzoetriazolderivater som dihydrooro-tatoxygenaseinhibitorer Download PDFInfo
- Publication number
- DK3019482T3 DK3019482T3 DK14754772.3T DK14754772T DK3019482T3 DK 3019482 T3 DK3019482 T3 DK 3019482T3 DK 14754772 T DK14754772 T DK 14754772T DK 3019482 T3 DK3019482 T3 DK 3019482T3
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- DK
- Denmark
- Prior art keywords
- compound
- pharmaceutically acceptable
- acceptable salt
- compound according
- structural formula
- Prior art date
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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- BLJHLOLVEXWHFS-UHFFFAOYSA-N methyl 2,3-diaminobenzoate Chemical compound COC(=O)C1=CC=CC(N)=C1N BLJHLOLVEXWHFS-UHFFFAOYSA-N 0.000 description 1
- WBTZDZSHLVPNLU-UHFFFAOYSA-N methyl 6-bromo-2h-benzotriazole-4-carboxylate Chemical compound COC(=O)C1=CC(Br)=CC2=NNN=C12 WBTZDZSHLVPNLU-UHFFFAOYSA-N 0.000 description 1
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
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- 230000003285 pharmacodynamic effect Effects 0.000 description 1
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- 150000003904 phospholipids Chemical class 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
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- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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- 230000002265 prevention Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
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- 150000003230 pyrimidines Chemical class 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- NPCOQXAVBJJZBQ-UHFFFAOYSA-N reduced coenzyme Q9 Natural products COC1=C(O)C(C)=C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C(O)=C1OC NPCOQXAVBJJZBQ-UHFFFAOYSA-N 0.000 description 1
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- 235000019204 saccharin Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
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- 238000007789 sealing Methods 0.000 description 1
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- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
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- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
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- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
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- 239000003765 sweetening agent Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
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- 239000005061 synthetic rubber Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 229940100611 topical cream Drugs 0.000 description 1
- 229940100615 topical ointment Drugs 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
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- 239000008215 water for injection Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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- 229940082509 xanthan gum Drugs 0.000 description 1
- 229930195724 β-lactose Natural products 0.000 description 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
- A61K31/41—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
- A61K31/4192—1,2,3-Triazoles
-
- 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
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- 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
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
-
- 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
- C07D403/10—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 carbon chain containing aromatic rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (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)
Claims (20)
1. Forbindelse med strukturformlen (I)
eller et farmaceutisk acceptabelt salt heraf, hvor de stiplede linjer [....] i ringen repræsenterer en eventuel binding, som kan være til stede i en hvilken som helst stabil kombination; Ri er valgt blandt hydrogen og alkylgruppe; R2 er valgt blandt
R3 er valgt blandt hydroxygruppe og aminogruppe; R4 er valgt blandt aryl- og heteroarylgruppe, hvor begge grupper eventuelt kan være substitueret, og hvor de eventuelle substituenter er valgt blandt en eller flere R5. R5 er valgt blandt alkylgruppe og -(CH2)nN(Ra)Rb; Ra og Rb er uafhængigt valgt blandt hydrogen, alkylgruppe og -C(O)alkyl; alternativt kan Ra og Rb sammen med nitrogenatomet, som de begge er forbundet til, udgøre en eventuelT substitueret 4- til 6-leddet heterocyklylgruppe indeholdende yderligere 0-2 heteroatomer, som uafhængigt er valgt blandt O og N; hvor den eventuelle substituent er en alkylgruppe; og 'n' er et heltal valgt blandt 0 og 1.
2. Forbindelse ifølge krav 1 eller et farmaceutisk acceptabelt salt heraf, hvor Ri er en methylgruppe.
3. Forbindelse ifølge krav 1 eller et farmaceutisk acceptabelt salt heraf, hvor R4 er en eventuelt substitueret phenyl.
4. Forbindelse ifølge krav 1 eller et farmaceutisk acceptabelt salt heraf, hvor R5 er valgt blandt methyl, acetylamino, isopropylaminomethyl, methylaminomethyl, dimethylaminomethyl,
og
5. Forbindelse ifølge krav 1 eller et farmaceutisk acceptabelt salt heraf, hvor R4 er 2,5-dimethyl-lH-pyrrol.
6. Forbindelse ifølge krav 1 eller et farmaceutisk acceptabelt salt heraf, hvor R3 er hydroxy.
7. Forbindelse ifølge krav 1 eller et farmaceutisk acceptabelt salt heraf, hvor forbindelsen er en forbindelse med strukturformlen (la)
hvor den stiplede linje [---], Ri, R3 og R4 er de samme som beskrevet i krav 1.
8. Forbindelse ifølge krav 1 eller et farmaceutisk acceptabelt salt heraf, hvor forbindelsen er en forbindelse med strukturformlen (Ib)
, hvor den stiplede linje [---], Ri, R3 og R4 er de samme som beskrevet i krav 1.
9. Forbindelse ifølge krav 1, hvor forbindelsen er valgt fra gruppen bestående af
eller et farmaceutisk acceptabelt salt heraf.
10. Forbindelse ifølge krav 1, hvor forbindelsen er en forbindelse med den følgende strukturformel
eller et farmaceutisk acceptabelt salt heraf.
11. Forbindelse ifølge krav 1, hvor forbindelsen er en forbindelse med den følgende strukturformel
eller et farmaceutisk acceptabelt salt heraf.
12. Forbindelse ifølge krav 1, hvor forbindelsen er en forbindelse med den følgende strukturformel
eller et farmaceutisk acceptabelt salt heraf.
13. Forbindelse ifølge krav 1, hvor forbindelsen er en forbindelse med den følgende strukturformel
eller et farmaceutisk acceptabelt salt heraf.
14. Forbindelse ifølge krav 1, hvor forbindelsen er en forbindelse med den følgende strukturformel
eller et farmaceutisk acceptabelt salt heraf.
15. Forbindelse ifølge krav 1, hvor forbindelsen er en forbindelse med den følgende strukturformel
eller et farmaceutisk acceptabelt salt heraf.
16. Farmaceutisk sammensætning omfattende i det mindste én forbindelse ifølge et hvilket som helst af kravene 1-15 eller et farmaceutisk acceptabelt salt heraf, i en blanding med i det mindste ét farmaceutisk acceptabelt bærestof eller excipiens, hvor blandinger heraf i alle forhold er inkluderet, til brug som lægemiddel.
17. Farmaceutisk sammensætning omfattende i det mindste én forbindelse ifølge et hvilket som helst af kravene 1-15 eller et farmaceutisk acceptabelt salt heraf, og i det mindste én yderligere aktiv ingrediens.
18. Forbindelse ifølge et hvilket som helst af kravene 1-15 eller et farmaceutisk acceptabelt salt heraf, til anvendelse i behandling eller profylakse af dissemineret sklerose eller reumatoid artritis.
19. Forbindelse ifølge et hvilket som helst af kravene 1-15 eller et farmaceutisk acceptabelt salt heraf til anvendelse i behandling og profylakse af kræftsygdomme, inflammatorisk tarmsygdom og reumatoid artritis.
20. Forbindelsen til anvendelse ifølge krav 19 til behandling af kræft.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN825CH2013 | 2013-02-25 | ||
| PCT/IB2014/059204 WO2014128669A2 (en) | 2013-02-25 | 2014-02-24 | Trisubstituted benzotriazole derivatives as dihydroorotate oxygenase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK3019482T3 true DK3019482T3 (da) | 2018-11-12 |
Family
ID=51391932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK14754772.3T DK3019482T3 (da) | 2013-02-25 | 2014-02-24 | Trisubstituerede benzoetriazolderivater som dihydrooro-tatoxygenaseinhibitorer |
Country Status (13)
| Country | Link |
|---|---|
| US (4) | US9630932B2 (da) |
| EP (2) | EP3019482B1 (da) |
| CY (1) | CY1120826T1 (da) |
| DK (1) | DK3019482T3 (da) |
| ES (1) | ES2694829T3 (da) |
| HR (1) | HRP20181908T1 (da) |
| HU (1) | HUE042032T2 (da) |
| LT (1) | LT3019482T (da) |
| PL (1) | PL3019482T3 (da) |
| PT (1) | PT3019482T (da) |
| RS (1) | RS57962B1 (da) |
| SI (1) | SI3019482T1 (da) |
| WO (1) | WO2014128669A2 (da) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI3019482T1 (sl) | 2013-02-25 | 2018-12-31 | Aurigene Discovery Technologies Limited | Derivati trisubstituiranega benzotriazola kot inhibitorji dihidroorotat oksigenaze |
| US20190192501A1 (en) * | 2016-08-23 | 2019-06-27 | Icahn School Of Medicine At Mount Sinai | Methods for treating pten-mutant tumors |
| JP2019535689A (ja) | 2016-10-27 | 2019-12-12 | バイエル アクチェンゲゼルシャフトＢａｙｅｒ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | ４，５−縮環１，２，４−トリアゾロン |
| CN110325514B (zh) | 2017-02-24 | 2023-06-13 | 默克专利有限责任公司 | 作为二氢乳清酸加氧酶抑制剂的1,4,6-三取代的-2-烷基-1H-苯并[d]咪唑衍生物 |
| US20180369206A1 (en) * | 2017-04-24 | 2018-12-27 | Aurigene Discovery Technologies Limited | Methods of Use for Trisubstituted Benzotriazole Derivatives as Dihydroorotate Oxygenase Inhibitors |
| CN110662539B (zh) * | 2017-04-24 | 2023-08-15 | 奥里吉恩探索技术有限公司 | 三取代的苯并三唑衍生物作为二氢乳清酸加氧酶抑制剂的使用方法 |
| MX2020008678A (es) * | 2018-02-20 | 2020-09-25 | Servier Lab | Metodos de uso para derivados de benzotriazol trisustituidos. |
| CN112672744B (zh) | 2018-06-22 | 2022-10-14 | 俄亥俄州国家创新基金会 | 抑制二氢乳清酸脱氢酶的方法和组合物 |
| EP3856176A4 (en) * | 2018-09-28 | 2022-05-04 | Acucela Inc. | VAP-1 INHIBITORS |
| CA3124401A1 (en) * | 2018-12-21 | 2020-06-25 | Les Laboratoires Servier | Crystalline and salt forms of an organic compound and pharmaceutical compositions thereof |
| BR112022026519A2 (pt) | 2020-06-24 | 2023-03-07 | Servier Lab | Uso de um composto inibidor de dhodh em terapia de câncer de combinação |
| WO2021262874A1 (en) | 2020-06-24 | 2021-12-30 | Servier Pharmaceuticals , Llc | Use of a dhodh inhibitor compound in combination cancer therapy |
| EP4203950A1 (en) | 2020-08-27 | 2023-07-05 | Servier Pharmaceuticals LLC | Use of a dhodh inhibitor compound in combination cancer therapy |
| WO2022167402A1 (en) | 2021-02-02 | 2022-08-11 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods of therapy comprising administering a therapeutically effective combination comprising a dhodh inhibitor and an idh inhibitor |
| CN117616026A (zh) * | 2021-07-05 | 2024-02-27 | 微境生物医药科技(上海)有限公司 | 用作dhodh抑制剂的1,2,4-三唑酮衍生物及其制备方法和用途 |
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|---|---|---|---|---|
| HU222234B1 (hu) | 1990-05-18 | 2003-05-28 | Aventis Pharma Deutschland Gmbh. | Eljárás izoxazol-4-karbonsav-amidok és hidroxi-alkilidén-cián-ecetsav-amidok, a vegyületeket tartalmazó gyógyászati készítmények és az ismert vegyületeket tartalmazó rákellenes hatású gyógyszerkészítmények előállítására |
| US5904937A (en) | 1997-10-03 | 1999-05-18 | Fmc Corporation | Taste masked pharmaceutical compositions |
| US6841561B1 (en) | 1999-10-01 | 2005-01-11 | Institute Of Molecular And Cell Biology | Dihydroorotate dehydrogenase inhibitors for the treatment of viral-mediated diseases |
| DE102005049953A1 (de) * | 2005-10-19 | 2007-04-26 | Sanofi-Aventis Deutschland Gmbh | Carbamoylbenzotriazol-derivate als Inhibitoren von Lipasen und Phospholipasen |
| AU2007293917B2 (en) * | 2006-09-08 | 2013-01-31 | F. Hoffmann-La Roche Ag | Benzotriazole kinase modulators |
| JP2012515191A (ja) * | 2009-01-19 | 2012-07-05 | ノイロサーチ アクティーゼルスカブ | Ｃｎｓ障害の治療に有用な新規なベンゾトリアゾール誘導体 |
| SG10201401169QA (en) * | 2009-04-02 | 2014-05-29 | Merck Serono Sa | Dihydroorotate dehydrogenase inhibitors |
| SI3019482T1 (sl) | 2013-02-25 | 2018-12-31 | Aurigene Discovery Technologies Limited | Derivati trisubstituiranega benzotriazola kot inhibitorji dihidroorotat oksigenaze |
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2014
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- 2014-02-24 ES ES14754772.3T patent/ES2694829T3/es active Active
- 2014-02-24 US US14/784,708 patent/US9630932B2/en active Active
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- 2014-02-24 LT LTEP14754772.3T patent/LT3019482T/lt unknown
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- 2014-02-24 DK DK14754772.3T patent/DK3019482T3/da active
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Also Published As
| Publication number | Publication date |
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| LT3019482T (lt) | 2018-11-26 |
| PT3019482T (pt) | 2018-11-28 |
| EP3019482B1 (en) | 2018-08-15 |
| ES2694829T3 (es) | 2018-12-27 |
| EP3417850A1 (en) | 2018-12-26 |
| US9937155B2 (en) | 2018-04-10 |
| US10080740B2 (en) | 2018-09-25 |
| US20190105304A1 (en) | 2019-04-11 |
| PL3019482T3 (pl) | 2019-02-28 |
| US20160200693A1 (en) | 2016-07-14 |
| US20170224663A1 (en) | 2017-08-10 |
| HRP20181908T1 (hr) | 2019-01-11 |
| EP3019482A4 (en) | 2017-05-10 |
| EP3019482A2 (en) | 2016-05-18 |
| CY1120826T1 (el) | 2019-12-11 |
| RS57962B1 (sr) | 2019-01-31 |
| US9630932B2 (en) | 2017-04-25 |
| HUE042032T2 (hu) | 2019-06-28 |
| WO2014128669A3 (en) | 2017-01-12 |
| SI3019482T1 (sl) | 2018-12-31 |
| WO2014128669A2 (en) | 2014-08-28 |
| US20180021311A1 (en) | 2018-01-25 |
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