HRP20192109T1 - Novi spoj i proces - Google Patents
Novi spoj i proces Download PDFInfo
- Publication number
- HRP20192109T1 HRP20192109T1 HRP20192109TT HRP20192109T HRP20192109T1 HR P20192109 T1 HRP20192109 T1 HR P20192109T1 HR P20192109T T HRP20192109T T HR P20192109TT HR P20192109 T HRP20192109 T HR P20192109T HR P20192109 T1 HRP20192109 T1 HR P20192109T1
- Authority
- HR
- Croatia
- Prior art keywords
- compound
- formula
- reaction
- process according
- hydrogen
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 35
- 238000000034 method Methods 0.000 title claims 22
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 238000006243 chemical reaction Methods 0.000 claims 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 7
- -1 nitrile compound Chemical class 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 238000005755 formation reaction Methods 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical group [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims 2
- 229910052808 lithium carbonate Inorganic materials 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229910052763 palladium Inorganic materials 0.000 claims 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000001632 sodium acetate Substances 0.000 claims 2
- 235000017281 sodium acetate Nutrition 0.000 claims 2
- 150000003672 ureas Chemical class 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- 101100439663 Arabidopsis thaliana CHR7 gene Proteins 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 239000007868 Raney catalyst Substances 0.000 claims 1
- 229910000564 Raney nickel Inorganic materials 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims 1
- 229910000024 caesium carbonate Inorganic materials 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- ZTQSADJAYQOCDD-UHFFFAOYSA-N ginsenoside-Rd2 Natural products C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O ZTQSADJAYQOCDD-UHFFFAOYSA-N 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000002823 nitrates Chemical class 0.000 claims 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 claims 1
- 239000003880 polar aprotic solvent Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 235000011056 potassium acetate Nutrition 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Claims (15)
1. Spoj nitrila ili njegova sol, pri čemu je spoj nitrila spoj formule (A):
naznačeno time, što:
• R1 i R2 su jednaki ili različiti i svaki je zasebno C1-C6 alkilna grupa ili C2-C7 acilna grupa ili R1 i R2 zajedno formiraju C1-C6 alkilensku grupu;
• R3 i R4 su jednaki ili različiti i svaki je zasebno vodik, halogen ili C1-C6 alkilna grupa;
• R5 i R6 su jednaki ili različiti i svaki je zasebno vodik, halogen ili C1-C6 alkilna grupa;
• X je CHR7, O ili NR7, a R7 je vodik ili C1-C6 alkilna grupa; i
• Ar je C6-C10 arilna grupa supstituirana s 0 do 4 supstituienta, od kojih je svaki supstituent zasebno halogen ili C1-C6 alkilna grupa.
2. Spoj nitrila prema patentnom zahtjevu 1 ili njegova sol, naznačeno time, što je spoj nitrila spoj formule (D):
3. Proces za proizvodnju spoja nitrila formule (A) kako je definirano u patentnom zahtjevu 1 ili 2, pri čemu se proces sastoji od izazivanja reakcije između spoja formule (I) i spoja formule (II):
naznačen time, što su R1, R2, R3, R4, R5, R6, X i Ar onakvi kako je definirano u patentnom zahtjevu 1, a Y je odlazeća grupa.
4. Proces prema patentnom zahtjevu 3, naznačen time, što:
• R1 i R2 su metil;
• R3 i R4 su vodik;
• R5 i R6 su vodik;
• X je CH2; i
• Ar je 2,4,6-trimetilfenil.
5. Proces prema patentnom zahtjevu 3 ili 4, naznačen time, što je Y odlazeća grupa koja je Cl, Br, I, -OC(O)RY i -S(O)2RY, pri čemu je RY vodik, C1-C6 alkilna grupa, C1-C6 alkoksi grupa ili C6-C10 arilna grupa, pri čemu je alkilna, alkoksi ili arilna grupa opcionalno supstituirana s 1 do 6 grupa odabranih iz nitrata i halida, poželjno naznačeno time, što je Y odlazeća grupa koja je Br, I, OMs, OTs, ONs,OAc ili OTf, poželjnije naznačeno time, što je Y odlazeća grupa koja je Br.
6. Proces prema bilo kojem patentnom zahtjevu od 3 do 5, naznačen time, što količina spoja formule (II) iznosi od 0,5 do 10,0 ekvivalenata spoja formula (I), poželjno naznačen time, što količina spoja formule (II) iznosi od 1,0 do 2,5 ekvivalenata spoja formule (I).
7. Proces prema bilo kojem patentnom zahtjevu od 3 do 6, naznačen time, što se proces sastoji od izazivanja reakcije između spoja formule (I) i spoja formule (II) u prisutnosti baze, poželjno naznačen time, što baza sadrži karbonat, hidrogenkarbonat, alkoksid, karboksilat ili amin, poželjnije naznačen time, što je baza litijev karbonat, natrijev karbonat, kalijev karbonat, cezijev karbonat, litijev acetat, natrijev acetat ili kalijev acetat, najpoželjnije naznačen time, što je baza litijev karbonat ili natrijev acetat.
8. Proces prema patentnom zahtjevu 7, naznačen time, što količina baze iznosi od 1,0 do 10,0 ekvivalenata spoja formule (I), poželjno naznačen time, što količina baze iznosi od 1,5 do 3,0 ekvivalenata spoja formule (I).
9. Proces prema bilo kojem patentnom zahtjevu od 3 do 8, naznačen time, što se proces sastoji od:
izazivanja reakcije između spoja formule (I) i spoja formule (II) u prisutnosti otapala, poželjno naznačeno time, što otapalo sadrži polarno aprotično otapalo, poželjnije naznačeno time, što otapalo sadrži acetonitril, tetrahidrofuran ili dioksan; i/ili
izazivanja reakcije između spoja formule (I) i spoja formule (II) tijekom najmanje 5 sata; i/ili
izazivanja reakcije između spoja formule (I) i spoja formule (II) na temperaturi od 50 do 100 °C, poželjno naznačeno time, što se proces sastoji od izazivanja reakcije između spoja formule (I) i spoja formule (II) u prisutnosti otapala pri refluksu.
10. Proces za proizvodnju spoja formule (B):
pri čemu se proces sastoji od smanjenja spoja formule (A) kako je definirano u patentnom zahtjevu 1 ili 2, naznačeno time, što su u R1, R2, R3, R4, R5, R6, X i Ar onakvi kako je definirano u bilo kojem patentnom zahtjevu od 1 do 4.
11. Proces prema patentnom zahtjevu 10, naznačen time, što se smanjenje spoja formule (A) sastoji od hidrogenacije spoja formule (A) u prisutnosti nikla, Raneyevog nikla, paladija, crnog paladija, paladijevog hidroksida, dioksida platine, poželjno Raneyevog nikla.
12. Proces prema patentnom zahtjevu 10 ili 11, koji se dodatno sastoji od proizvodnje spoja formule (A) pomoću procesa definiranog u bilo kojem patentnom zahtjevu od 3 do 9.
13. Proces za proizvodnju spoja formule (C):
naznačen time, što su R1, R2, R3, R4, R5, R6, X i Ar onakvi kako je definirano u bilo kojem patentnom zahtjevu od 1 do 4, a Q je O, NR8 ili CR8 i R8 je vodik ili C1-C6 alkilna grupa,
pri čemu se proces sastoji od:
(i) procesa za proizvodnju spoja formule (A), kako je definirano u bilo kojem patentnom zahtjevu do 3 do 9; i/ili
(ii) procesa za pripremanje spoja formule (B) smanjenjem spoja formule (A), kako je definirano u bilo kojem patentnom zahtjevu od 10 do 12.
14. Proces prema patentnom zahtjevu 13, koji se sastoji od:
(a) pripremanja spoja formule (B) smanjenjem spoja formule (A), ako je definirano u bilo kojem patentnom zahtjevu od 13 do 15; i
(b) izazivanja dodatne reakcije spoja formule (B) radi dobivanja spoja formule (C),
opcionalno naznačeno time, što je korak (b) reakcija formiranja derivata uree, poželjno naznačeno time, što se reakcija formiranja derivata uree izvodi izazivanjem reakcije između spoja formule (B) sa spojem O=C=N– Z+, pri čemu je Z+ kation metala, poželjnije naznačeno time, što je Z+ natrij ili kalij.
15. Proces prema patentnom zahtjevu 13 ili 14, naznačen time, što
• R1 i R2 su metil;
• R3 i R4 su vodik;
• R5 i R6 su vodik;
• X je CH2;
• Ar je 2,4,6-trimetilfenil; i
• Q je O.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1613054.4A GB201613054D0 (en) | 2016-07-28 | 2016-07-28 | New compound and process |
| PCT/GB2017/052190 WO2018020249A1 (en) | 2016-07-28 | 2017-07-27 | New compound and process |
| EP17748880.6A EP3490988B1 (en) | 2016-07-28 | 2017-07-27 | New compound and process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20192109T1 true HRP20192109T1 (hr) | 2020-02-21 |
Family
ID=56936838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20192109TT HRP20192109T1 (hr) | 2016-07-28 | 2019-11-22 | Novi spoj i proces |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US10710998B2 (hr) |
| EP (1) | EP3490988B1 (hr) |
| JP (1) | JP6985367B2 (hr) |
| KR (1) | KR102396059B1 (hr) |
| CN (1) | CN109641891B (hr) |
| CY (1) | CY1122138T1 (hr) |
| DK (1) | DK3490988T3 (hr) |
| ES (1) | ES2751948T3 (hr) |
| GB (1) | GB201613054D0 (hr) |
| HR (1) | HRP20192109T1 (hr) |
| HU (1) | HUE046509T2 (hr) |
| LT (1) | LT3490988T (hr) |
| PL (1) | PL3490988T3 (hr) |
| PT (1) | PT3490988T (hr) |
| RS (1) | RS59566B1 (hr) |
| SI (1) | SI3490988T1 (hr) |
| TW (1) | TWI739871B (hr) |
| WO (1) | WO2018020249A1 (hr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10864213B2 (en) | 2014-05-12 | 2020-12-15 | Verona Pharma Plc | Treatment |
| GB201502260D0 (en) | 2015-02-11 | 2015-04-01 | Verona Pharma Plc | Salt of Pyrimido[6,1-A]Isoquinolin-4-one compound |
| CA3211820A1 (en) | 2021-04-29 | 2022-11-03 | Zhiya LI | Isoquinolone compound and use thereof |
| WO2023109802A1 (zh) * | 2021-12-14 | 2023-06-22 | 海思科医药集团股份有限公司 | 三环稠杂环类pde3/4双重抑制及其用途 |
| EP4378942A1 (en) | 2022-12-02 | 2024-06-05 | Sandoz AG | Crystal form of a pde3/4 inhibitor |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ185900A (en) | 1976-12-10 | 1981-04-24 | Hoechst Ag | Pyrimido (6,1-a) isoquinolin-4-ones medicaments intermediate isoquinolines |
| FI64370C (fi) | 1977-05-05 | 1983-11-10 | Hoechst Ag | Foerfarande foer framstaellning av terapeutiskt anvaendbara pyimido-(6,1-a)isokinolin-2-imino-4-onderivat |
| DE2847693A1 (de) | 1978-11-03 | 1980-05-22 | Hoechst Ag | Verfahren zur herstellung von pyrimido-(6,1-a)-isochinolin-2-onen |
| DE3135831A1 (de) | 1981-09-10 | 1983-04-28 | Hoechst Ag, 6230 Frankfurt | 9,10-substituierte 2-mesitylimino-3-alkyl-3,4,6,7-tetrahydro-2h-pyrimido(6,1-a)isochinolin-4-one, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| ZW6284A1 (en) | 1983-05-05 | 1985-10-30 | Hoffmann La Roche | Novel pyrimidone derivatives |
| DE60005493T2 (de) | 1999-03-31 | 2004-07-01 | Vernalis Ltd., Wokingham | Pyrimido[6,1-a]isochinolinonderivate |
| PL2603509T3 (pl) | 2010-08-09 | 2014-11-28 | Verona Pharma Plc | Krystaliczna postać związku pirymidio[6,1-a]izochinolin-4-onowego |
| PL2968312T3 (pl) | 2013-03-15 | 2018-08-31 | Verona Pharma Plc | Kombinacja leków |
| US10864213B2 (en) | 2014-05-12 | 2020-12-15 | Verona Pharma Plc | Treatment |
| RS58897B1 (sr) | 2014-09-15 | 2019-08-30 | Verona Pharma Plc | Tečna inhalaciona formulacija koja sadrži rpl554 |
| GB201502260D0 (en) | 2015-02-11 | 2015-04-01 | Verona Pharma Plc | Salt of Pyrimido[6,1-A]Isoquinolin-4-one compound |
-
2016
- 2016-07-28 GB GBGB1613054.4A patent/GB201613054D0/en not_active Ceased
-
2017
- 2017-07-27 RS RS20191474A patent/RS59566B1/sr unknown
- 2017-07-27 PT PT177488806T patent/PT3490988T/pt unknown
- 2017-07-27 PL PL17748880T patent/PL3490988T3/pl unknown
- 2017-07-27 KR KR1020197004436A patent/KR102396059B1/ko active IP Right Grant
- 2017-07-27 CN CN201780046788.1A patent/CN109641891B/zh active Active
- 2017-07-27 LT LTEP17748880.6T patent/LT3490988T/lt unknown
- 2017-07-27 EP EP17748880.6A patent/EP3490988B1/en active Active
- 2017-07-27 DK DK17748880T patent/DK3490988T3/da active
- 2017-07-27 TW TW106125312A patent/TWI739871B/zh active
- 2017-07-27 ES ES17748880T patent/ES2751948T3/es active Active
- 2017-07-27 WO PCT/GB2017/052190 patent/WO2018020249A1/en unknown
- 2017-07-27 HU HUE17748880A patent/HUE046509T2/hu unknown
- 2017-07-27 SI SI201730098T patent/SI3490988T1/sl unknown
- 2017-07-27 JP JP2019503748A patent/JP6985367B2/ja active Active
- 2017-07-27 US US16/309,435 patent/US10710998B2/en active Active
-
2019
- 2019-10-04 CY CY20191101046T patent/CY1122138T1/el unknown
- 2019-11-22 HR HRP20192109TT patent/HRP20192109T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP3490988B1 (en) | 2019-08-28 |
| WO2018020249A1 (en) | 2018-02-01 |
| KR20190034231A (ko) | 2019-04-01 |
| CY1122138T1 (el) | 2020-11-25 |
| US10710998B2 (en) | 2020-07-14 |
| PT3490988T (pt) | 2019-10-28 |
| US20190330206A1 (en) | 2019-10-31 |
| TWI739871B (zh) | 2021-09-21 |
| CN109641891B (zh) | 2021-05-04 |
| GB201613054D0 (en) | 2016-09-14 |
| SI3490988T1 (sl) | 2019-11-29 |
| JP6985367B2 (ja) | 2021-12-22 |
| ES2751948T3 (es) | 2020-04-02 |
| KR102396059B1 (ko) | 2022-05-10 |
| TW201806951A (zh) | 2018-03-01 |
| JP2019527228A (ja) | 2019-09-26 |
| RS59566B1 (sr) | 2019-12-31 |
| PL3490988T3 (pl) | 2020-02-28 |
| CN109641891A (zh) | 2019-04-16 |
| EP3490988A1 (en) | 2019-06-05 |
| DK3490988T3 (da) | 2019-10-28 |
| LT3490988T (lt) | 2019-10-10 |
| HUE046509T2 (hu) | 2020-03-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HRP20192109T1 (hr) | Novi spoj i proces | |
| HRP20191932T1 (hr) | Sinteza boronatnih soli i njihove uporabe | |
| ES2579175T3 (es) | Proceso para la producción de intermediarios de estetrol | |
| HRP20201847T2 (hr) | Postupak za pripremu spoja diariltiohidantoina | |
| HRP20211770T1 (hr) | 2-(morfolin-4-il)-1,7-naftiridini | |
| TW201542499A (zh) | 螺槳烷（ｐｒｏｐｅｌｌａｎｅ）衍生物及合成 | |
| TWI645901B (zh) | 雙環烷基化合物及合成 | |
| PH12016502334A1 (en) | Method for producing fused heterocyclic compound | |
| JP2019527228A5 (hr) | ||
| HRP20220129T1 (hr) | Postupak za pripremu uglavnom dijastereomerno čistog fosforodiamidatnog oligomera, fosforodiamidatni oligomer dobiven takvim postupkom i farmaceutski pripravak koji sadrži takav fosforodiamidatni oligomer | |
| JP2015509939A5 (hr) | ||
| RU2015143637A (ru) | Способы получения апоптоз агента | |
| PE20080109A1 (es) | N-sulfonilacion selectiva de alcoholes sustituidos con 2-aminotrifluoralquilo | |
| RU2014137470A (ru) | Способы и соединения, которые можно использовать для синтеза антагонистов рецепторов орексина-2 | |
| HRP20171167T1 (hr) | Priprava intermedijera pirimidina koji služe za proizvodnju macitentana | |
| EP3398952A1 (en) | Synthesis process of ruxolitinib | |
| PH12018500582A1 (en) | Crosslinked nucleic acid guna, method for producing same, and intermediate compound | |
| HRP20170711T1 (hr) | Kontinuirani postupak za alkilaciju cikličnih tercijarnih amina | |
| RU2012116208A (ru) | Способ получения n-ацилбифенилаланина | |
| NZ730843A (en) | Synthesis of copanlisib and its dihydrochloride salt | |
| RU2015129994A (ru) | Способ получения 1-(4-(4-(3, 4-дихлор-2-фторфениламино)-7-метоксихиназолин-6-илокси)пиперидин-1-ил)проп-2-ен-1-она | |
| EA201990237A1 (ru) | Новые способы получения стимуляторов растворимой гуанилатциклазы | |
| RU2015106018A (ru) | Фторпиколиноилфториды и способы их получения | |
| ES2702193T3 (es) | Proceso para la preparación de compuestos de isoxazolina ópticamente activos | |
| JP2016516809A5 (hr) |