HRP20192301T1 - Postupak dobivanja spoja n-(3,5-dimetilfenil)-n'-(2-trifluormetilfenil)gvanidina - Google Patents
Postupak dobivanja spoja n-(3,5-dimetilfenil)-n'-(2-trifluormetilfenil)gvanidina Download PDFInfo
- Publication number
- HRP20192301T1 HRP20192301T1 HRP20192301TT HRP20192301T HRP20192301T1 HR P20192301 T1 HRP20192301 T1 HR P20192301T1 HR P20192301T T HRP20192301T T HR P20192301TT HR P20192301 T HRP20192301 T HR P20192301T HR P20192301 T1 HRP20192301 T1 HR P20192301T1
- Authority
- HR
- Croatia
- Prior art keywords
- compound
- formula
- trifluoromethylphenyl
- dimethylphenyl
- guanidine
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 14
- 238000000034 method Methods 0.000 title claims 10
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 title 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 title 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 title 1
- DVIJFJSZZNOTLP-UHFFFAOYSA-N 1-(3,5-dimethylphenyl)-2-[2-(trifluoromethyl)phenyl]guanidine Chemical compound CC1=CC(C)=CC(NC(=N)NC=2C(=CC=CC=2)C(F)(F)F)=C1 DVIJFJSZZNOTLP-UHFFFAOYSA-N 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- 239000007787 solid Substances 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 3
- -1 cyanamide compound Chemical class 0.000 claims 2
- 239000003495 polar organic solvent Substances 0.000 claims 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- 230000001413 cellular effect Effects 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 102000004169 proteins and genes Human genes 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C277/02—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of guanidine from cyanamide, calcium cyanamide or dicyandiamides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C277/06—Purification or separation of guanidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C277/08—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of substituted guanidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/18—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of six-membered aromatic rings
-
- 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)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Analytical Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (13)
1. Postupak dobivanja spoja N-(3,5-dimetilfenil)-N′-(2-trifluormetilfenil) gvanidina formule (I),
,
naznačen time što se sastoji u reakciji soli spoja formule (II) ili smjese soli spoja formule (II) i spoja formule (II)
s cijanamidnim spojem formule (III)
,
u prisutnosti polarnog organskog otapala.
2. Postupak u skladu s patentnim zahtjevom 1, naznačen time što se postupak provodi reakcijom smjese spoja formule (II) i soli spoja formule (II) s cijanamidnim spojem formule (III).
3. Postupak u skladu s bilo kojim od patentnih zahtjeva 1-2, naznačen time što je sol spoja formule (II) klorhidratna sol spoja formule (II).
4. Postupak u skladu s bilo kojim od patentnih zahtjeva 1-3, naznačen time što je polarno organsko otapalo (C1-C3) alkohol.
5. Postupak u skladu s patentnim zahtjevom 4, naznačen time što je (C1-C3) alkohol etanol.
6. Postupak u skladu s bilo kojim od patentnih zahtjeva 1-5, naznačen time što se reakciju provodi na temperaturi koja se kreće 60 °C do 75 °C.
7. Postupak u skladu s bilo kojim od patentnih zahtjeva 1-6, naznačen time što dodatno uključuje dodatni korak kristaliziranja spoja formule (I).
8. Postupak u skladu s patentnim zahtjevom 7, naznačen time što se kristaliziranje provodi u prisutnosti smjese (C1-C3) alkohola i vode.
9. Kristalni čvrsti oblik A spoja N-(3,5-dimetilfenil)-N′-(2-trifluormetilfenil) gvanidina formule (I), naznačen time što pokazuje talište od 131.5 °C.
10. Kristalni čvrsti oblik A formule (I) u skladu s patentnim zahtjevom 9, naznačen time što pokazuje DSC od 132.4 °C.
11. Farmaceutski pripravak, naznačen time što sadrži terapijski djelotvornu količinu kristalnog čvrstog oblika spoja N-(3,5-dimetilfenil)-N′-(2-trifluormetilfenil) gvanidina formule (I) u skladu s bilo kojim od patentnih zahtjeva 9-10, uz jedan ili više farmaceutski prihvatljivih pomoćnih tvari ili nosača.
12. Kristalni čvrsti oblik A spoja N-(3,5-dimetilfenil)-N′-(2-trifluormetilfenil) gvanidina formule (I) u skladu s bilo kojim od patentnih zahtjeva 9-10, naznačen time što je namijenjen upotrebi kao lijek.
13. Kristalni čvrsti oblik A spoja N-(3,5-dimetilfenil)-N′-(2-trifluormetilfenil)gvanidina formule (I) u skladu s bilo kojim od patentnih zahtjeva 9-10, naznačen time što je namijenjen upotrebi u liječenju stanja posredovanog staničnim proteinima tipa ro-GTPaza.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ARP150102582A AR101498A1 (es) | 2015-08-11 | 2015-08-11 | Procedimiento para la preparación del compuesto n-(3,5-dimetilfenil)-n-(2-trifluorometilfenil)guanidina y su forma cristalina a |
| EP15382424 | 2015-08-11 | ||
| PCT/EP2016/069033 WO2017025560A1 (en) | 2015-08-11 | 2016-08-10 | A process for the preparation of the compound n-(3,5-dimethylphenyl)-n'-(2-trifluoromethylphenyl) guanidine |
| EP16756641.3A EP3334707B1 (en) | 2015-08-11 | 2016-08-10 | A process for the preparation of the compound n-(3,5-dimethylphenyl)-n'-(2-trifluoromethylphenyl) guanidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20192301T1 true HRP20192301T1 (hr) | 2020-03-20 |
Family
ID=56799434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20192301TT HRP20192301T1 (hr) | 2015-08-11 | 2019-12-20 | Postupak dobivanja spoja n-(3,5-dimetilfenil)-n'-(2-trifluormetilfenil)gvanidina |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US10343984B2 (hr) |
| EP (1) | EP3334707B1 (hr) |
| JP (1) | JP6748188B2 (hr) |
| CN (1) | CN107922322B (hr) |
| AR (1) | AR101498A1 (hr) |
| BR (1) | BR112018002614B1 (hr) |
| CA (1) | CA2994781A1 (hr) |
| CY (1) | CY1122481T1 (hr) |
| DK (1) | DK3334707T3 (hr) |
| ES (1) | ES2756580T3 (hr) |
| HK (1) | HK1256253A1 (hr) |
| HR (1) | HRP20192301T1 (hr) |
| HU (1) | HUE046959T2 (hr) |
| LT (1) | LT3334707T (hr) |
| MX (1) | MX2018001548A (hr) |
| PL (1) | PL3334707T3 (hr) |
| PT (1) | PT3334707T (hr) |
| RS (1) | RS59759B1 (hr) |
| RU (1) | RU2737430C2 (hr) |
| SI (1) | SI3334707T1 (hr) |
| WO (1) | WO2017025560A1 (hr) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN172842B (hr) * | 1990-05-17 | 1993-12-11 | Boots Pharmaceuticals Limited | |
| AU2962297A (en) * | 1996-05-24 | 1998-01-05 | Neurosearch A/S | Phenyl derivatives useful as blockers of chloride channels |
| US8283370B2 (en) * | 2008-10-03 | 2012-10-09 | The United States Of America As Represented By The Secretary Of The Army | Imidazolidinedione derivatives as antimalarial agents, preparation thereof, and methods of use |
| DK2766342T3 (en) * | 2011-10-11 | 2016-05-02 | Univ Nac Quilmes | PHENYL-guanidine derivatives |
-
2015
- 2015-08-11 AR ARP150102582A patent/AR101498A1/es unknown
-
2016
- 2016-08-10 LT LTEP16756641.3T patent/LT3334707T/lt unknown
- 2016-08-10 SI SI201630561T patent/SI3334707T1/sl unknown
- 2016-08-10 MX MX2018001548A patent/MX2018001548A/es unknown
- 2016-08-10 PT PT167566413T patent/PT3334707T/pt unknown
- 2016-08-10 DK DK16756641.3T patent/DK3334707T3/da active
- 2016-08-10 US US15/751,437 patent/US10343984B2/en active Active
- 2016-08-10 HU HUE16756641A patent/HUE046959T2/hu unknown
- 2016-08-10 ES ES16756641T patent/ES2756580T3/es active Active
- 2016-08-10 RU RU2018107840A patent/RU2737430C2/ru active
- 2016-08-10 CA CA2994781A patent/CA2994781A1/en active Pending
- 2016-08-10 BR BR112018002614-0A patent/BR112018002614B1/pt active IP Right Grant
- 2016-08-10 EP EP16756641.3A patent/EP3334707B1/en active Active
- 2016-08-10 JP JP2018506997A patent/JP6748188B2/ja active Active
- 2016-08-10 PL PL16756641T patent/PL3334707T3/pl unknown
- 2016-08-10 RS RS20191669A patent/RS59759B1/sr unknown
- 2016-08-10 WO PCT/EP2016/069033 patent/WO2017025560A1/en active Application Filing
- 2016-08-10 CN CN201680045772.4A patent/CN107922322B/zh active Active
-
2018
- 2018-11-29 HK HK18115310.1A patent/HK1256253A1/zh unknown
-
2019
- 2019-12-20 HR HRP20192301TT patent/HRP20192301T1/hr unknown
- 2019-12-27 CY CY20191101359T patent/CY1122481T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN107922322A (zh) | 2018-04-17 |
| JP6748188B2 (ja) | 2020-08-26 |
| RU2018107840A (ru) | 2019-09-12 |
| DK3334707T3 (da) | 2020-01-06 |
| US20180244608A1 (en) | 2018-08-30 |
| CA2994781A1 (en) | 2017-02-16 |
| AR101498A1 (es) | 2016-12-21 |
| JP2018525393A (ja) | 2018-09-06 |
| PL3334707T3 (pl) | 2020-05-18 |
| PT3334707T (pt) | 2020-01-14 |
| EP3334707B1 (en) | 2019-10-09 |
| LT3334707T (lt) | 2020-01-27 |
| RU2018107840A3 (hr) | 2019-12-18 |
| CY1122481T1 (el) | 2021-01-27 |
| SI3334707T1 (sl) | 2020-03-31 |
| HK1256253A1 (zh) | 2019-09-20 |
| CN107922322B (zh) | 2023-11-03 |
| US10343984B2 (en) | 2019-07-09 |
| BR112018002614A2 (hr) | 2018-10-02 |
| RS59759B1 (sr) | 2020-02-28 |
| WO2017025560A1 (en) | 2017-02-16 |
| HUE046959T2 (hu) | 2020-04-28 |
| RU2737430C2 (ru) | 2020-11-30 |
| ES2756580T3 (es) | 2020-04-27 |
| BR112018002614B1 (pt) | 2023-04-11 |
| EP3334707A1 (en) | 2018-06-20 |
| MX2018001548A (es) | 2018-06-22 |
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