HRP20210820T1 - Inovativna priprema i kristalizacija iosimenola - Google Patents
Inovativna priprema i kristalizacija iosimenola Download PDFInfo
- Publication number
- HRP20210820T1 HRP20210820T1 HRP20210820TT HRP20210820T HRP20210820T1 HR P20210820 T1 HRP20210820 T1 HR P20210820T1 HR P20210820T T HRP20210820T T HR P20210820TT HR P20210820 T HRP20210820 T HR P20210820T HR P20210820 T1 HRP20210820 T1 HR P20210820T1
- Authority
- HR
- Croatia
- Prior art keywords
- iosimenol
- crystal
- group
- butanol
- hydroxide
- Prior art date
Links
- DLPPIGPJCKKVBA-UHFFFAOYSA-N Iosimenol Chemical compound OCC(O)CNC(=O)C1=C(I)C(C(=O)N)=C(I)C(N(CC(O)CO)C(=O)CC(=O)N(CC(O)CO)C=2C(=C(C(=O)NCC(O)CO)C(I)=C(C(N)=O)C=2I)I)=C1I DLPPIGPJCKKVBA-UHFFFAOYSA-N 0.000 title claims 9
- 229950004246 iosimenol Drugs 0.000 title claims 9
- 238000002360 preparation method Methods 0.000 title claims 4
- 238000002425 crystallisation Methods 0.000 title claims 3
- 230000008025 crystallization Effects 0.000 title claims 3
- 238000000034 method Methods 0.000 claims 15
- 239000013078 crystal Substances 0.000 claims 7
- 150000007529 inorganic bases Chemical class 0.000 claims 5
- -1 2,3-dihydroxypropyl group Chemical group 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 238000010438 heat treatment Methods 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
- 239000002168 alkylating agent Substances 0.000 claims 2
- 229940100198 alkylating agent Drugs 0.000 claims 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 2
- 238000005259 measurement Methods 0.000 claims 2
- 229910001507 metal halide Inorganic materials 0.000 claims 2
- 150000005309 metal halides Chemical class 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- 239000011877 solvent mixture Substances 0.000 claims 2
- 238000000527 sonication Methods 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims 1
- 229940093475 2-ethoxyethanol Drugs 0.000 claims 1
- HCGFUIQPSOCUHI-UHFFFAOYSA-N 2-propan-2-yloxyethanol Chemical compound CC(C)OCCO HCGFUIQPSOCUHI-UHFFFAOYSA-N 0.000 claims 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
- 239000001110 calcium chloride Substances 0.000 claims 1
- 229910001628 calcium chloride Inorganic materials 0.000 claims 1
- 235000011148 calcium chloride Nutrition 0.000 claims 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims 1
- 239000000920 calcium hydroxide Substances 0.000 claims 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 150000004292 cyclic ethers Chemical class 0.000 claims 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical class CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 1
- 229910001629 magnesium chloride Inorganic materials 0.000 claims 1
- 235000011147 magnesium chloride Nutrition 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims 1
- 229960000281 trometamol Drugs 0.000 claims 1
- 239000011592 zinc chloride Substances 0.000 claims 1
- 235000005074 zinc chloride Nutrition 0.000 claims 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having carbon atoms of carboxamide groups, amino groups and at least three atoms of bromine or iodine, bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/005—Selection of auxiliary, e.g. for control of crystallisation nuclei, of crystal growth, of adherence to walls; Arrangements for introduction thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/0081—Use of vibrations, e.g. ultrasound
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
- B01J19/10—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing sonic or ultrasonic vibrations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/08—Preparation of carboxylic acid amides from amides by reaction at nitrogen atoms of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D2009/0086—Processes or apparatus therefor
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00139—Controlling the temperature using electromagnetic heating
- B01J2219/00141—Microwaves
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Saccharide Compounds (AREA)
Claims (15)
1. Kristal iosimenol naznačen time što
(i) uzorak difrakcije rendgenskih zraka u prahu koji ima četiri ili više 2θ ± 0.2 pika i odabran između 8.1°, 9.6°, 9.9°, 10.0°, 10.7°, 15.4°, 16.9°, 18.0°, 18.6°, 18.9°, 20.1°, 20.4°, 21.9°, 22.2°, 22.5°, 24.8°, 26.1°, 26.8°, 27.5°, 28.9°, 29.4°, 29.7°, 30.5°, 34.1° i 34.6°, pri čemu je mjerenje navedenog kristala na temperaturi od 293 K; ili
(ii) parametri jedinične stanice pri T = 293K jednaki sljedećim: a = 21.8919(16) A, b = 9.8210(9) Å, c = 20.0233(12) A, α = 90°, β = 94.955(1)°, γ = 90°, volumen 4289(6) Å3 i monoklinička P21/prostorna skupina.
2. Kristal iosimenola prema zahtjevu 1 naznačen time što uzorak difrakcije rendgenskih zraka u prahu ima četiri ili više 2θ ± 0.2 pika i odabran između 8.1°, 20.4°, 21.9°, 22.2°, 22.5°, 26.8° i 30.5°, pri čemu mjerenje navedenog kristala je na temperaturi od 293 K.
3. Postupak za pripremu iosimenola formule:
[image]
sadrži reakcijski CVI formule:
[image]
s alkilirajućim sredstvom koje uvodi 2,3-dihidroksipropilnu skupinu u prisutnosti anorganske baze u otapalu koje sadrži 2-metoksietanol.
4. Postupak prema zahtjevu 3, naznačen time što alkilirajuće sredstvo uvodi 2,3-dihidroksipropilnu skupinu
(i) je odabrano iz skupine koju čine 3-halo-1,2-propandiol i glicidol; i/ili
(ii) je 3-halo-1,2-propandiol.
5. Postupak prema bilo kojem od zahtjeva 3 do 4, naznačen time što anorganska baza
(i) je odabrana iz skupine koju čine hidroksid alkalijskog metala i hidroksid zemnoalkalijskog metala; i/ili
(ii) je litijev hidroksid, kalcijev hidroksid, natrijev hidroksid, kalijev hidroksid ili njihova mješavina.
6. Postupak prema bilo kojem od zahtjeva 3 do 5, naznačen time što se reakcija za pripremu iosimenola provodi u prisutnosti metalhalogenida pored anorganske baze.
7. Postupak prema zahtjevu 6, naznačen time što je metalhalogenid odabran iz skupine koju čine CaCl2, ZnCl2 i MgCl2.
8. Postupak za pripremu kristalnog iosimenola iz zasićene ili prezasićene otopine navedenog spoja, sadrži:
korak 1: suspendiranje deioniziranog iosimenola u mješavini otapala koja sadrži (i) jedno ili više organskih otapala odabranih između C1-C6 linearnih ili razgranatih alkanola, alkoksialkanola, C2-C8 alifatskih i C4-C6 cikličkih etera, i (ii) vodu,
korak 2: podvrgavanje mješavine zagrijavanju i/ili ultrazvuku kako bi se mješavina potpuno otopila,
korak 3: nastavak podvrgavanja otopine istom ili različitom zagrijavanju i/ili ultrazvuku kako bi se taložio kristal, i
korak 4: prikupljanje rezultirajućeg kristala na filtru.
9. Postupak prema patentnom zahtjevu 8, naznačen time što se zagrijavanje u koraku 2 i/ili koraku 3 vrši mikrovalnom pećnicom.
10. Postupak prema zahtjevu 8 ili 9, naznačen time što organsko otapalo(a) u koraku 1 je/su odabrano iz skupine koja sadrži metanol, etanol, n-propanol, 2-propanol, n-butanol, i-butanol, sec-butanol , terc-butanol, pentanole uključujući izoamilalkohole, heksanole, 2-metoksietanol, 2-etoksietanol, 1-metoksi-2-propanol i 2-izopropoksietanol.
11. Postupak prema bilo kojem od zahtjeva 8 do 10, naznačen time što
mješavina otapala u koraku 1 sadrži do 20% vode.
12. Postupak prema bilo kojem od zahtjeva 8 do 11, naznačen time što
koncentracija iosimenola kao početnog materijala u koraku 1 je 10 w/v % - 60 w/v %.
13. Postupak prema bilo kojem od zahtjeva 8 do 12, naznačen time što se postupak kristalizacije u koraku 3 može započeti dodavanjem sjemena kristala iosimenola za vrijeme ili nakon povišenja temperature.
14. Postupak prema bilo kojem od zahtjeva 8 do 13, naznačen time što se trometamol koristi za puferiranje pH tijekom postupka kristalizacije.
15. Postupak prema bilo kojem od zahtjeva 8 do 14, naznačen time što se koraci 2 i 3 izvode na 70° C - 140° C.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562250720P | 2015-11-04 | 2015-11-04 | |
| EP16798573.8A EP3371147B1 (en) | 2015-11-04 | 2016-11-02 | Innovative preparation and crystallization of iosimenol |
| PCT/JP2016/004798 WO2017077710A1 (en) | 2015-11-04 | 2016-11-02 | Innovative preparation and crystallization of iosimenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20210820T1 true HRP20210820T1 (hr) | 2021-06-25 |
Family
ID=57354423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20210820TT HRP20210820T1 (hr) | 2015-11-04 | 2021-05-21 | Inovativna priprema i kristalizacija iosimenola |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US10544089B2 (hr) |
| EP (1) | EP3371147B1 (hr) |
| JP (1) | JP6778746B2 (hr) |
| KR (1) | KR20180077198A (hr) |
| CN (1) | CN108368031B (hr) |
| AU (2) | AU2016350219B2 (hr) |
| CA (1) | CA3002502A1 (hr) |
| CY (1) | CY1124164T1 (hr) |
| DK (1) | DK3371147T3 (hr) |
| ES (1) | ES2873828T3 (hr) |
| HK (1) | HK1257821A1 (hr) |
| HR (1) | HRP20210820T1 (hr) |
| HU (1) | HUE054876T2 (hr) |
| LT (1) | LT3371147T (hr) |
| MY (1) | MY186399A (hr) |
| NZ (1) | NZ742104A (hr) |
| PH (1) | PH12018500872A1 (hr) |
| PL (1) | PL3371147T3 (hr) |
| PT (1) | PT3371147T (hr) |
| SA (1) | SA518391413B1 (hr) |
| SG (1) | SG11201803241YA (hr) |
| SI (1) | SI3371147T1 (hr) |
| TW (1) | TWI724049B (hr) |
| WO (1) | WO2017077710A1 (hr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102128423B1 (ko) * | 2018-09-17 | 2020-07-01 | (주)유케이케미팜 | 조영제 이오메프롤의 제조방법 |
| CN111777525B (zh) * | 2019-04-04 | 2021-08-27 | 成都西岭源药业有限公司 | 一种碘克沙醇的精制方法 |
| KR102179649B1 (ko) * | 2019-10-11 | 2020-11-18 | (주)에이에스텍 | 디에틸아미노하이드록시벤조일헥실벤조에이트의 제조 방법 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5698739A (en) | 1989-07-05 | 1997-12-16 | Schering Aktiengesellschaft | Carboxamide non-ionic contrast media |
| US6072069A (en) * | 1998-11-04 | 2000-06-06 | Biophysica, Inc. | Biodegradable nonionic contrast media |
| NO20053687D0 (no) * | 2005-07-29 | 2005-07-29 | Amersham Health As | Crystallisation Process. |
| WO2009091758A1 (en) * | 2008-01-14 | 2009-07-23 | Mallinckrodt Inc. | Process for the preparation of iosimenol |
-
2016
- 2016-11-02 PT PT167985738T patent/PT3371147T/pt unknown
- 2016-11-02 KR KR1020187014635A patent/KR20180077198A/ko unknown
- 2016-11-02 US US15/772,710 patent/US10544089B2/en not_active Expired - Fee Related
- 2016-11-02 CA CA3002502A patent/CA3002502A1/en not_active Abandoned
- 2016-11-02 TW TW105135469A patent/TWI724049B/zh not_active IP Right Cessation
- 2016-11-02 HU HUE16798573A patent/HUE054876T2/hu unknown
- 2016-11-02 MY MYPI2018701574A patent/MY186399A/en unknown
- 2016-11-02 JP JP2018522702A patent/JP6778746B2/ja active Active
- 2016-11-02 EP EP16798573.8A patent/EP3371147B1/en active Active
- 2016-11-02 ES ES16798573T patent/ES2873828T3/es active Active
- 2016-11-02 DK DK16798573.8T patent/DK3371147T3/da active
- 2016-11-02 LT LTEP16798573.8T patent/LT3371147T/lt unknown
- 2016-11-02 AU AU2016350219A patent/AU2016350219B2/en not_active Ceased
- 2016-11-02 WO PCT/JP2016/004798 patent/WO2017077710A1/en active Application Filing
- 2016-11-02 SG SG11201803241YA patent/SG11201803241YA/en unknown
- 2016-11-02 CN CN201680066838.8A patent/CN108368031B/zh active Active
- 2016-11-02 NZ NZ742104A patent/NZ742104A/en unknown
- 2016-11-02 SI SI201631172T patent/SI3371147T1/sl unknown
- 2016-11-02 PL PL16798573T patent/PL3371147T3/pl unknown
-
2018
- 2018-04-22 SA SA518391413A patent/SA518391413B1/ar unknown
- 2018-04-23 PH PH12018500872A patent/PH12018500872A1/en unknown
-
2019
- 2019-01-04 HK HK19100172.9A patent/HK1257821A1/zh unknown
-
2021
- 2021-05-18 CY CY20211100428T patent/CY1124164T1/el unknown
- 2021-05-21 HR HRP20210820TT patent/HRP20210820T1/hr unknown
- 2021-07-16 AU AU2021205101A patent/AU2021205101B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2017077710A1 (en) | 2017-05-11 |
| LT3371147T (lt) | 2021-08-10 |
| DK3371147T3 (da) | 2021-05-25 |
| PH12018500872A1 (en) | 2018-11-05 |
| KR20180077198A (ko) | 2018-07-06 |
| AU2021205101A1 (en) | 2021-08-19 |
| TW201722906A (zh) | 2017-07-01 |
| JP2018536654A (ja) | 2018-12-13 |
| PT3371147T (pt) | 2021-05-24 |
| AU2016350219A1 (en) | 2018-05-17 |
| MY186399A (en) | 2021-07-22 |
| PL3371147T3 (pl) | 2021-10-25 |
| SG11201803241YA (en) | 2018-05-30 |
| NZ742104A (en) | 2023-01-27 |
| US20190177266A1 (en) | 2019-06-13 |
| AU2021205101B2 (en) | 2022-11-24 |
| AU2016350219B2 (en) | 2021-04-29 |
| CY1124164T1 (el) | 2022-05-27 |
| EP3371147B1 (en) | 2021-04-07 |
| US10544089B2 (en) | 2020-01-28 |
| JP6778746B2 (ja) | 2020-11-04 |
| TWI724049B (zh) | 2021-04-11 |
| SI3371147T1 (sl) | 2021-08-31 |
| EP3371147A1 (en) | 2018-09-12 |
| HUE054876T2 (hu) | 2021-10-28 |
| CA3002502A1 (en) | 2017-05-11 |
| SA518391413B1 (ar) | 2022-03-06 |
| HK1257821A1 (zh) | 2019-11-01 |
| CN108368031B (zh) | 2022-05-03 |
| CN108368031A (zh) | 2018-08-03 |
| ES2873828T3 (es) | 2021-11-04 |
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