HRP20230948T1 - Postupak za proizvodnju (s)-2-((2-((s)-4-(difluorometil)-2-oksooksazolidin-3-il)-5,6-dihidrobenzo[f]imidazo[1,2−d][1,4]oksazepin-9-il)amino) propanamida - Google Patents
Postupak za proizvodnju (s)-2-((2-((s)-4-(difluorometil)-2-oksooksazolidin-3-il)-5,6-dihidrobenzo[f]imidazo[1,2−d][1,4]oksazepin-9-il)amino) propanamida Download PDFInfo
- Publication number
- HRP20230948T1 HRP20230948T1 HRP20230948TT HRP20230948T HRP20230948T1 HR P20230948 T1 HRP20230948 T1 HR P20230948T1 HR P20230948T T HRP20230948T T HR P20230948TT HR P20230948 T HRP20230948 T HR P20230948T HR P20230948 T1 HRP20230948 T1 HR P20230948T1
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- Prior art keywords
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- copper
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- 238000000034 method Methods 0.000 title claims 14
- SGEUNORSOZVTOL-CABZTGNLSA-N (2S)-2-[[2-[(4S)-4-(difluoromethyl)-2-oxo-1,3-oxazolidin-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]amino]propanamide Chemical compound FC([C@H]1N(C(OC1)=O)C=1N=C2N(CCOC3=C2C=CC(=C3)N[C@H](C(=O)N)C)C=1)F SGEUNORSOZVTOL-CABZTGNLSA-N 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 7
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 claims 3
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims 3
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 claims 3
- 229940126657 Compound 17 Drugs 0.000 claims 3
- 229940125773 compound 10 Drugs 0.000 claims 3
- 229940125758 compound 15 Drugs 0.000 claims 3
- 229940126142 compound 16 Drugs 0.000 claims 3
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims 3
- 239000003446 ligand Substances 0.000 claims 3
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 claims 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 claims 2
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 229940126543 compound 14 Drugs 0.000 claims 2
- 150000001879 copper Chemical class 0.000 claims 2
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(i) oxide Chemical group [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 claims 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical group [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims 2
- FRDZGSBXKJXGNR-HTQZYQBOSA-N (1r,2r)-2-n,2-n-dimethylcyclohexane-1,2-diamine Chemical compound CN(C)[C@@H]1CCCC[C@H]1N FRDZGSBXKJXGNR-HTQZYQBOSA-N 0.000 claims 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims 1
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 claims 1
- NPAXPTHCUCUHPT-UHFFFAOYSA-N 3,4,7,8-tetramethyl-1,10-phenanthroline Chemical compound CC1=CN=C2C3=NC=C(C)C(C)=C3C=CC2=C1C NPAXPTHCUCUHPT-UHFFFAOYSA-N 0.000 claims 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 229940125797 compound 12 Drugs 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 claims 1
- 239000012026 peptide coupling reagents Substances 0.000 claims 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 claims 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/553—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (9)
1. Postupak za proizvodnju spoja 18 koji ima strukturu:
[image]
naznačen time, da obuhvaća reakciju spoja 17 koji ima strukturu:
[image]
s amonijakom i reagensom za spajanje peptida koji je N-(3-dimetilaminopropil)-N'-etil karbodiimid hidroklorid/N-hidroksi sukcinimid, u svrhu tvorbe spoja 18.
2. Postupak prema patentnom zahtjevu 1, naznačen time, da se spoj 17 proizvodi putem postupka koji obuhvaća reakciju spoja 16 koji ima strukturu:
[image]
sa (S)-2-aminopropanskom kiselinom i katalizatorom bakar (I), u svrhu dobivanja spoja 17.
3. Postupak prema patentnom zahtjevu 2, naznačen time, da katalizator bakar (I) je bakar(I) oksid.
4. Postupak prema patentnom zahtjevu 2, naznačen time, da se spoj 16 proizvodi putem postupka koji obuhvaća reakciju spoja 15 koji ima strukturu:
[image]
sa spojem 10 koji ima strukturu:
[image]
bakrenom soli i ligandom, u svrhu tvorbe spoja 16.
5. Postupak prema patentnom zahtjevu 4, naznačen time, da bakrena sol je bakar(II) acetat.
6. Postupak prema patentnom zahtjevu 5, naznačen time, da ligand je trans-N,N- dimetilcikloheksan-1,2-diamin.
7. Postupak prema patentnom zahtjevu 4, naznačen time, da ligand je 3,4,7,8- tetrametil-1,10-fenantrolin.
8. Postupak prema patentnom zahtjevu 4, naznačen time, da se spoj 10 proizvodi putem postupka koji obuhvaća:
(a) reakciju spoja 6 koji ima strukturu:
[image]
s kalijevim ftalimidom u svrhu tvorbe spoja 7 koji ima strukturu:
[image]
(b) reakciju spoja 7 s hidrazinom u vodi, u svrhu tvorbe spoja 8 koji ima strukturu:
[image]
(c) reakciju spoja 8 s klorovodičnom kiselinom, u svrhu tvorbe spoja 9 koji ima strukturu:
[image]
(d) reakciju spoja 9 s trifosgenom, u svrhu tvorbe spoja 10.
9. Postupak prema patentnom zahtjevu 4, naznačen time, da se spoj 15 proizvodi putem postupka koji obuhvaća:
(a) reakciju spoja 12 koji ima strukturu:
[image]
s kloroacetaldehidom, u svrhu tvorbe spoja 13 koji ima strukturu:
[image]
(b) reakciju spoja 13 s N-jodosukcinimidom, u svrhu tvorbe spoja 14 koji ima strukturu:
[image]
(c) reakciju spoja 14 s etilmagnezijevim bromidom, u svrhu tvorbe spoja 15.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662434836P | 2016-12-15 | 2016-12-15 | |
| EP20209166.6A EP3851441B1 (en) | 2016-12-15 | 2017-12-15 | Process for the preparation of (s)-2-((2-((s)-4-(difluoromethyl)-2-oxooxazolidin-3-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-9-yl)amino) propanamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20230948T1 true HRP20230948T1 (hr) | 2023-11-24 |
Family
ID=61027659
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20230948TT HRP20230948T1 (hr) | 2016-12-15 | 2017-12-15 | Postupak za proizvodnju (s)-2-((2-((s)-4-(difluorometil)-2-oksooksazolidin-3-il)-5,6-dihidrobenzo[f]imidazo[1,2−d][1,4]oksazepin-9-il)amino) propanamida |
| HRP20210592TT HRP20210592T1 (hr) | 2016-12-15 | 2021-04-13 | Postupak za pripravu (s)-2-((2-((s)-4-(difluorometil)-2-oksooksazolidin-3-il)-5,6-dihidrobenzo[f]imidazo[1,2-d][1,4]oksazepin-9-il)amino) propanamida |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20210592TT HRP20210592T1 (hr) | 2016-12-15 | 2021-04-13 | Postupak za pripravu (s)-2-((2-((s)-4-(difluorometil)-2-oksooksazolidin-3-il)-5,6-dihidrobenzo[f]imidazo[1,2-d][1,4]oksazepin-9-il)amino) propanamida |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US10781219B2 (hr) |
| EP (2) | EP3555107B1 (hr) |
| JP (1) | JP7004720B2 (hr) |
| KR (1) | KR102537048B1 (hr) |
| CN (1) | CN110088111B (hr) |
| AR (1) | AR110527A1 (hr) |
| AU (2) | AU2017378188B2 (hr) |
| BR (1) | BR112019010481A2 (hr) |
| CA (1) | CA3044500A1 (hr) |
| ES (2) | ES2953833T3 (hr) |
| HR (2) | HRP20230948T1 (hr) |
| HU (1) | HUE062517T2 (hr) |
| IL (2) | IL267265B (hr) |
| MX (2) | MX2019006958A (hr) |
| PL (2) | PL3555107T3 (hr) |
| SG (1) | SG10201913961PA (hr) |
| SI (1) | SI3555107T1 (hr) |
| TW (1) | TWI770093B (hr) |
| WO (1) | WO2018109204A1 (hr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9650393B2 (en) | 2015-07-02 | 2017-05-16 | Genentech, Inc. | Benzoxazepin oxazolidinone compounds and methods of use |
| CN110650963B (zh) * | 2017-04-28 | 2022-09-27 | 豪夫迈·罗氏有限公司 | Gdc-0077的多晶型物和固体形式及其制备方法 |
| TW202120515A (zh) * | 2019-11-25 | 2021-06-01 | 大陸商上海翰森生物醫藥科技有限公司 | 含三并環類衍生物的鹽或晶型及其醫藥組成物 |
| EP4114567A1 (en) | 2020-03-03 | 2023-01-11 | Momentive Performance Materials Inc. | Catalyst composition |
| TW202313563A (zh) | 2021-05-28 | 2023-04-01 | 美商建南德克公司 | 苯并氧氮呯噁唑啶酮化合物之製備方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ597833A (en) | 2009-09-28 | 2014-01-31 | Hoffmann La Roche | Benzoxazepin pi3k inhibitor compounds and methods of use |
| EP2688891B1 (en) * | 2011-03-21 | 2017-11-15 | F. Hoffmann-La Roche AG | Benzoxazepin compounds selective for pi3k p110 delta and methods of use |
| AU2014230812B2 (en) | 2013-03-13 | 2016-04-07 | F. Hoffmann-La Roche Ag | Process for making benzoxazepin compounds |
| US9650393B2 (en) * | 2015-07-02 | 2017-05-16 | Genentech, Inc. | Benzoxazepin oxazolidinone compounds and methods of use |
| CN110650963B (zh) | 2017-04-28 | 2022-09-27 | 豪夫迈·罗氏有限公司 | Gdc-0077的多晶型物和固体形式及其制备方法 |
-
2017
- 2017-12-15 WO PCT/EP2017/083143 patent/WO2018109204A1/en unknown
- 2017-12-15 CN CN201780078083.8A patent/CN110088111B/zh active Active
- 2017-12-15 BR BR112019010481A patent/BR112019010481A2/pt active Search and Examination
- 2017-12-15 HU HUE20209166A patent/HUE062517T2/hu unknown
- 2017-12-15 JP JP2019531931A patent/JP7004720B2/ja active Active
- 2017-12-15 PL PL17835634T patent/PL3555107T3/pl unknown
- 2017-12-15 EP EP17835634.1A patent/EP3555107B1/en active Active
- 2017-12-15 PL PL20209166.6T patent/PL3851441T3/pl unknown
- 2017-12-15 ES ES20209166T patent/ES2953833T3/es active Active
- 2017-12-15 CA CA3044500A patent/CA3044500A1/en active Pending
- 2017-12-15 TW TW106144193A patent/TWI770093B/zh active
- 2017-12-15 SG SG10201913961PA patent/SG10201913961PA/en unknown
- 2017-12-15 AR ARP170103528A patent/AR110527A1/es unknown
- 2017-12-15 MX MX2019006958A patent/MX2019006958A/es unknown
- 2017-12-15 EP EP20209166.6A patent/EP3851441B1/en active Active
- 2017-12-15 AU AU2017378188A patent/AU2017378188B2/en active Active
- 2017-12-15 KR KR1020197020323A patent/KR102537048B1/ko active IP Right Grant
- 2017-12-15 HR HRP20230948TT patent/HRP20230948T1/hr unknown
- 2017-12-15 SI SI201730711T patent/SI3555107T1/sl unknown
- 2017-12-15 ES ES17835634T patent/ES2867389T3/es active Active
-
2019
- 2019-06-12 IL IL267265A patent/IL267265B/en active IP Right Grant
- 2019-06-13 MX MX2020010948A patent/MX2020010948A/es unknown
- 2019-06-14 US US16/441,765 patent/US10781219B2/en active Active
-
2021
- 2021-02-17 AU AU2021201046A patent/AU2021201046A1/en not_active Abandoned
- 2021-02-24 IL IL281087A patent/IL281087A/en unknown
- 2021-04-13 HR HRP20210592TT patent/HRP20210592T1/hr unknown
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