ME02407B - Soli i solvati derivata tetrahidroizohinolina - Google Patents
Soli i solvati derivata tetrahidroizohinolinaInfo
- Publication number
- ME02407B ME02407B MEP-2016-98A MEP9816A ME02407B ME 02407 B ME02407 B ME 02407B ME P9816 A MEP9816 A ME P9816A ME 02407 B ME02407 B ME 02407B
- Authority
- ME
- Montenegro
- Prior art keywords
- solvate
- degrees
- sodium salt
- crystalline
- phenylmethoxy
- Prior art date
Links
- 239000002904 solvent Substances 0.000 title claims 2
- 150000003839 salts Chemical class 0.000 title 1
- 150000003526 tetrahydroisoquinolines Chemical class 0.000 title 1
- 239000012453 solvate Substances 0.000 claims 34
- 159000000000 sodium salts Chemical class 0.000 claims 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 10
- 238000000034 method Methods 0.000 claims 8
- GHBCIXGRCZIPNQ-MHZLTWQESA-N (3s)-2-(2,2-diphenylacetyl)-6-methoxy-5-phenylmethoxy-3,4-dihydro-1h-isoquinoline-3-carboxylic acid Chemical compound C([C@H](N(CC1=CC=C2OC)C(=O)C(C=3C=CC=CC=3)C=3C=CC=CC=3)C(O)=O)C1=C2OCC1=CC=CC=C1 GHBCIXGRCZIPNQ-MHZLTWQESA-N 0.000 claims 7
- 229960004592 isopropanol Drugs 0.000 claims 5
- 238000000634 powder X-ray diffraction Methods 0.000 claims 5
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 claims 4
- 239000007787 solid Substances 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- -1 sodium alkoxide Chemical class 0.000 claims 2
- NASFKTWZWDYFER-UHFFFAOYSA-N sodium;hydrate Chemical compound O.[Na] NASFKTWZWDYFER-UHFFFAOYSA-N 0.000 claims 2
- ACGYQXYBZPWBLS-HNNXBMFYSA-N (3s)-6-methoxy-5-phenylmethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid Chemical compound C([C@H](NCC1=CC=C2OC)C(O)=O)C1=C2OCC1=CC=CC=C1 ACGYQXYBZPWBLS-HNNXBMFYSA-N 0.000 claims 1
- 238000002441 X-ray diffraction Methods 0.000 claims 1
- JRVORWMACMEOAD-UHFFFAOYSA-N [N].C1=NC=CC2=CC=CC=C21 Chemical group [N].C1=NC=CC2=CC=CC=C21 JRVORWMACMEOAD-UHFFFAOYSA-N 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 150000003950 cyclic amides Chemical class 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- A61K31/47—Quinolines; Isoquinolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (18)
1. Natrijumova so (S) -2- (difenilacetil) -1,2,3,4-tetrahidro-6-metoksi-5- (fenilmetoksi) -3- izohinolin karboksilne kiseline i njenih solvata, u amorfnom obliku ili u obliku kristalnog solvata.
2. Natrijumova so, prema patentnom zahtevu 1, naznačena time da je solvat etanolni solvat, izo-propanolni solvat ili hidrat koji ima 2 do 5 molekule vode.
3. Natrijumova so, prema patentnom zahtevu 2, naznačena time da je solvat etanolni solvat ili izo-propanolni solvat.
4. Natrijumova so, prema patentnom zahtevu 2, naznačena time da je solvat hidrat koji sadrži 2 molekula vode.
5. Natrijumova so, prema patentnom zahtevu 2, naznačena time da je solvat hidrat koji sadrži 3 do 5 molekula vode.
6. Hidrat natrijumove soli, prema patentnom zahtevu 4, naznačen time da kristalni solvat pokazuje rendgenogram rendgenske difrakcije praha koji sadrži signal/pik na 19. 3 stepeni 2θ ± 0.1 stepeni 2θ i opciono dalje sadrži signal/pik na 18.2 stepeni 2θ ± 0.1 stepeni 2θ, i opciono naznačen time kristalni solvat pokazuje 13C NMR spektar čvrstog stanja koji sadrži signale na 55.7, 128.2 i 151.3 ppm ± 0,2 ppm.
7. Hidrat natrijumove soli, prema patentnom zahtevu 5, naznačen time da kristalni solvat pokazuje rendgenogram difrakcije x-zraka na prahu koji sadrži signal/pik na 15.2 stepena 2θ ± 0.1 stepeni 2θ i opciono dalje sadrži najmanje dva signala/pika iz sledeće grupe koju čine 4.8, 7.3, 12.0, 12.6, 23.5, i 24.5 stepeni 2θ ± 0.1 stepeni 2θ i opciono pri čemu pomenuti kristalni solvat pokazuje 13C NMR spektar čvrstog stanja koji sadrži signale na 53,7, 122,9 i 128,1 ppm ± 0,2 ppm.
8. Etanolni solvat prema patentnom zahtevu 3, naznačen time da kristalni solvat pokazuje rendgenogram rendgenske difrakcije praha koji sadrži pik na 14.3 stepeni 2θ ± 0.1 stepena 2θ ili pokazuje rendgenogram difrakcije iks-zraka na prahu koji sadrži signal/pik na 14,7 stepeni 2θ ± 0.1 stepeni 2θ ili pokazuje rendgenogram koji sadrži najmanje dva signala/pika iz grupe koja sadrži 14.3, 14.7, 26.9, i 29.7 stepeni 2θ ± 0.1 stepen 2θ, i opciono gde navedeni kristalni solvat pokazuje 13C NMR spektar čvrstog stanja koji sadrži signale na 18.4, 139.7 i 141.4 ± 0,2 ppm.
9. Izo-propanolni solvat prema patentnom zahtevu 3, naznačen time da pokazuje rendgenogram difrakcije x-zraka praha koji sadrži najmanje jedan pik izabran iz grupe koja se sastoji od 20.6, 26.6, 27.2, 28.3 i 29.3 stepena 2θ ± 0.1 stepen 2θ i opciono dalje sadrži najmanje dva pika izabrana iz grupe koju čine 25.0, 26.0, 26.6, 27.2, 28.3 i 29.3 stepena 2θ ± 0.1 stepen 2θ ili dalje sadrži najmanje jedan signal izabran iz grupe koju čine signali
10.8, 14.0, 21.1, 21.9, i 22.5 stepeni 2θ ± 0.1 stepen 2θ, i opciono gde pomenuti kristalni solvat pokazuje spektar 13C NMR čvrstog stanja koji sadrži signale na 63.1 i 140.7 ppm ± 0,2 ppm. 10. Farmaceutski preparat koji sadrži natrijumovu so (S)-2-(difenilacetil)-1,2,3,4-tetrahidro-6-metoksi-5-(fenilmetoksi)-3-izohinolin karboksilne kiseline ili solvat natrijumove soli zajedno sa farmaceutski prihvatljivim nosačem, sredstvom za razblaživanje ili ekscipijentom, naznačen time da je natrijumova so (S)-2-(difenilacetil)-1,2,3,4-tetrahidro-6-metoksi-5-(fenilmetoksi)-3-izohinolin karboksilne kiseline u amorfnom obliku ili u obliku kristalnog solvata.
11. Farmaceutski preparat prema patentnom zahtevu 10, naznačen time, što je formulisan za oralnu primenu.
12. Postupak za dobijanje natrijumove soli (S)-2-(difenilacetil)-1,2,3,4-tetrahidro-6-metoksi-5-(fenilmetoksi)-3-izohinolin karboksilne kiseline ili solvata sastoji se iz: (i) tretiranja (S)-2-(difenilacetil)-1,2,3,4-tetrahidro-6-metoksi-5-(fenilmetoksi)-3-izohinolin karbonske kiseline sa natrijum-alkoksidom; (ii) građenja kristalnog alkoholnog solvata proizvedene natrijumove soli nagrađene postupkom (i); i(iii) rekristalizacije solvata.
13. Postupak prema patentnom zahtevu 12 naznačen time da je navedeni kristalni solvat etanolni solvat, izopropanolni solvat, ili hidrat koji sadrži 2 do 5 molekule vode.
14. Postupak prema patentnom zahtevu 12 naznačen time da se molekul alkohola kristalnog alkoholnog solvata formiran u koraku (ii) se menja sa drugim molekulom solvata pre, tokom ili nakon koraka (iii), naročito naznačen time da je formirani solvat hidrat.
15. Postupak prema bilo kojem od patentnih zahteva 12 ili 14 naznačen time da je solvat koji se prekristališe u koraku (iii) izo-propanolni solvat.
16. Postupak prema bilo kojem od patentnih zahteva 12 do 15, koji sadrži dalji korak sušenja solvata.
17. Postupak prema bilo kom od patentnih zahteva 12 do 15 koji dalje sadrži postupak acidifikacije natrijumove soli da bi se formirala (S)-2-(difenilacetil)-1,2,3,4-tetrahidro-6-metoksi-5-(fenilmetoksi)-3-izohinolin karboksilna kiselina u suštinski čistom obliku, naznačen time da suštinski čist oblik ukazuje na proizvod koji ima više od 96% hemijske čistoće i / ili više od 97% ee.
18. Postupak za dobijanje solvata natrijumove soli (S)-2-(difenilacetil)-1,2,3,4-tetrahidro-6-metoksi-5-(fenilmetoksi)-3-izohinolin karboksilne kiseline koji sadrži sledeće korake: (i) acilovanje izohinolinskog atoma azota (S)-1,2,3,4-tetrahidro-6-metoksi-5-(fenilmetoksi)-3-izohinolin karboksilne kiseline sa aktiviranim cikličnim amidom formule: naznačen time prsten A predstavlja 5-člani heterocikl koji sadrži azot; i(ii) tretiranje proizvoda iz faze (i) sa alkoksidnom soli u alkoholnom rastvaraču. 4
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36636710P | 2010-07-21 | 2010-07-21 | |
| PCT/GB2011/001096 WO2012010843A1 (en) | 2010-07-21 | 2011-07-21 | Salt and solvates of a tetrahydroisoquinoline derivative |
| EP11740973.0A EP2595960B1 (en) | 2010-07-21 | 2011-07-21 | Salt and solvates of a tetrahydroisoquinoline derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ME02407B true ME02407B (me) | 2016-09-20 |
Family
ID=44386640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MEP-2016-98A ME02407B (me) | 2010-07-21 | 2011-07-21 | Soli i solvati derivata tetrahidroizohinolina |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US8614227B2 (me) |
| EP (2) | EP3081557A1 (me) |
| JP (3) | JP5948326B2 (me) |
| CN (2) | CN105777636A (me) |
| AU (3) | AU2011281381B2 (me) |
| CA (1) | CA2803699C (me) |
| DK (1) | DK2595960T3 (me) |
| ES (1) | ES2570135T3 (me) |
| HK (1) | HK1224290A1 (me) |
| HR (1) | HRP20160540T1 (me) |
| HU (1) | HUE028620T2 (me) |
| ME (1) | ME02407B (me) |
| NZ (2) | NZ605444A (me) |
| PL (1) | PL2595960T3 (me) |
| PT (1) | PT2595960E (me) |
| SI (1) | SI2595960T1 (me) |
| SM (1) | SMT201600171B (me) |
| WO (1) | WO2012010843A1 (me) |
| ZA (1) | ZA201300169B (me) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL2595960T3 (pl) * | 2010-07-21 | 2016-09-30 | Sól i solwaty pochodnej tetrahydroizochinoliny | |
| US9320530B2 (en) * | 2013-03-13 | 2016-04-26 | The Spectranetics Corporation | Assisted cutting balloon |
| WO2015003223A1 (en) * | 2013-07-08 | 2015-01-15 | Spinifex Pharmaceuticals Pty Ltd | Heterocyclic compounds and methods of their use |
| PT3245198T (pt) | 2015-01-13 | 2020-06-16 | Novartis Ag | Derivados de pirrolidina como antagonistas de angiotensina ii tipo 2 |
| US10308628B2 (en) | 2015-03-12 | 2019-06-04 | Novartis Ag | Heterocyclic compounds and methods for their use |
| CN106478502B (zh) * | 2015-08-29 | 2021-04-27 | 上海翰森生物医药科技有限公司 | 1,2,3,4-四氢异喹啉衍生物、其制备方法和应用 |
| WO2018001997A1 (en) | 2016-06-27 | 2018-01-04 | Ratiopharm Gmbh | Crystalline calcium salt of (s)-2-(diphenylacetyl)-1,2,3,4-tetrahydro-6-methoxy-5-(phenylmethoxy)-3-isoquinoline carboxylic acid |
| JP2019514862A (ja) * | 2017-03-23 | 2019-06-06 | ノバルティス アーゲー | （ｓ）−２−（ジフェニルアセチル）−１，２，３，４−テトラヒドロ−６−メトキシ−５−（フェニルメトキシ）−３−イソキノリンカルボン酸ナトリウムの無水結晶形 |
| AU2018279669B8 (en) * | 2017-06-09 | 2020-10-15 | Shandong Danhong Pharmaceutical Co., Ltd. | Carboxylic acid derivative as at AT2R receptor antagonist |
| WO2020012266A1 (en) | 2018-07-12 | 2020-01-16 | Novartis Ag | Biocatalytic synthesis of olodanrigan (ema401) from 3-(2-(benzyloxy)-3-methoxyphenyl)propenoic acid with phenylalanine ammonia lyase |
| CN112672989A (zh) * | 2018-07-12 | 2021-04-16 | 科德克希思公司 | 工程化苯丙氨酸氨裂合酶多肽 |
| CN111620816B (zh) * | 2020-05-27 | 2023-06-02 | 上海赛默罗生物科技有限公司 | 螺桨烷类衍生物、其制备方法、药物组合物和用途 |
| GB202100352D0 (en) * | 2021-01-12 | 2021-02-24 | Balticgruppen Bio Ab | New methods |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5246943A (en) | 1992-05-19 | 1993-09-21 | Warner-Lambert Company | Substituted 1,2,3,4-tetahydroisoquinolines with angiotensin II receptor antagonist properties |
| US5236934A (en) | 1992-08-26 | 1993-08-17 | E. I. Du Pont De Nemours And Company | 1,2,3,4-tetrahydroisoquinolines useful in the treatment of CNS disorders |
| US6300356B1 (en) * | 1998-02-25 | 2001-10-09 | Merck & Co., Inc. | Method for decreasing QT dispersion or inhibiting the progression of QT dispersion with an angiotensin II receptor antagonist |
| WO2006066361A1 (en) | 2004-12-24 | 2006-06-29 | The University Of Queensland | Method of treatment or prophylaxis |
| JP5230595B2 (ja) | 2006-03-20 | 2013-07-10 | スピニフェクス ファーマシューティカルズ ピーティーワイ リミテッド | 炎症性疼痛の治療または予防の方法 |
| US9095587B2 (en) * | 2010-01-19 | 2015-08-04 | Spinifex Pharmaceuticals Pty Ltd | Methods and compositions for improved nerve conduction velocity |
| PL2595960T3 (pl) * | 2010-07-21 | 2016-09-30 | Sól i solwaty pochodnej tetrahydroizochinoliny |
-
2011
- 2011-07-21 PL PL11740973.0T patent/PL2595960T3/pl unknown
- 2011-07-21 CN CN201610152658.3A patent/CN105777636A/zh active Pending
- 2011-07-21 JP JP2013520203A patent/JP5948326B2/ja not_active Expired - Fee Related
- 2011-07-21 ES ES11740973T patent/ES2570135T3/es active Active
- 2011-07-21 HU HUE11740973A patent/HUE028620T2/en unknown
- 2011-07-21 DK DK11740973.0T patent/DK2595960T3/en active
- 2011-07-21 SI SI201130804A patent/SI2595960T1/sl unknown
- 2011-07-21 NZ NZ605444A patent/NZ605444A/en not_active IP Right Cessation
- 2011-07-21 WO PCT/GB2011/001096 patent/WO2012010843A1/en not_active Ceased
- 2011-07-21 EP EP15200360.4A patent/EP3081557A1/en not_active Withdrawn
- 2011-07-21 CA CA2803699A patent/CA2803699C/en not_active Expired - Fee Related
- 2011-07-21 CN CN201180035468.9A patent/CN103003244B/zh not_active Expired - Fee Related
- 2011-07-21 PT PT117409730T patent/PT2595960E/pt unknown
- 2011-07-21 AU AU2011281381A patent/AU2011281381B2/en not_active Ceased
- 2011-07-21 ME MEP-2016-98A patent/ME02407B/me unknown
- 2011-07-21 HR HRP20160540TT patent/HRP20160540T1/hr unknown
- 2011-07-21 EP EP11740973.0A patent/EP2595960B1/en active Active
- 2011-07-21 NZ NZ708529A patent/NZ708529A/en not_active IP Right Cessation
- 2011-07-21 US US13/187,882 patent/US8614227B2/en not_active Expired - Fee Related
-
2013
- 2013-01-08 ZA ZA2013/00169A patent/ZA201300169B/en unknown
- 2013-07-03 HK HK16112556.3A patent/HK1224290A1/en unknown
- 2013-11-18 US US14/083,391 patent/US8927575B2/en not_active Expired - Fee Related
-
2014
- 2014-12-17 US US14/573,774 patent/US9162985B2/en not_active Expired - Fee Related
-
2015
- 2015-10-06 AU AU2015238774A patent/AU2015238774A1/en not_active Abandoned
-
2016
- 2016-04-11 JP JP2016078656A patent/JP2016164178A/ja active Pending
- 2016-06-15 SM SM201600171T patent/SMT201600171B/it unknown
-
2017
- 2017-05-15 AU AU2017203236A patent/AU2017203236A1/en not_active Abandoned
- 2017-08-14 JP JP2017156436A patent/JP2017214415A/ja active Pending
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