HRP20211379T1 - Kristalni oblik antagonista gnrh receptora i postupak njegovog dobivanja - Google Patents
Kristalni oblik antagonista gnrh receptora i postupak njegovog dobivanja Download PDFInfo
- Publication number
- HRP20211379T1 HRP20211379T1 HRP20211379TT HRP20211379T HRP20211379T1 HR P20211379 T1 HRP20211379 T1 HR P20211379T1 HR P20211379T T HRP20211379T T HR P20211379TT HR P20211379 T HRP20211379 T HR P20211379T HR P20211379 T1 HRP20211379 T1 HR P20211379T1
- Authority
- HR
- Croatia
- Prior art keywords
- solvent
- crystal form
- ketone
- ether
- water
- Prior art date
Links
- 239000002464 receptor antagonist Substances 0.000 title claims 2
- 229940044551 receptor antagonist Drugs 0.000 title claims 2
- 102000008238 LHRH Receptors Human genes 0.000 title 1
- 108010021290 LHRH Receptors Proteins 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 14
- 239000013078 crystal Substances 0.000 claims 12
- 239000002904 solvent Substances 0.000 claims 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 8
- 150000002576 ketones Chemical class 0.000 claims 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 5
- 238000000034 method Methods 0.000 claims 4
- 239000012046 mixed solvent Substances 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 3
- 239000000579 Gonadotropin-Releasing Hormone Substances 0.000 claims 2
- 101000857870 Squalus acanthias Gonadoliberin Proteins 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 2
- 238000001035 drying Methods 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims 2
- 238000001914 filtration Methods 0.000 claims 2
- XLXSAKCOAKORKW-AQJXLSMYSA-N gonadorelin Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)NCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 XLXSAKCOAKORKW-AQJXLSMYSA-N 0.000 claims 2
- 229940035638 gonadotropin-releasing hormone Drugs 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 238000001228 spectrum Methods 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002124 endocrine Effects 0.000 claims 1
- 210000000750 endocrine system Anatomy 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000000634 powder X-ray diffraction Methods 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 238000004537 pulping Methods 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- 210000004994 reproductive system Anatomy 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/28—Oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Claims (7)
1. Kristalni oblik I spoja formule (I), naznačen time što: taj kristalni oblik I ima spektar rendgenske difrakcije praha, koji je dobiven uporabom Cu-Kα zračenja i predstavljen kutom difrakcije 2θ kuta, pri čemu postoje karakteristične maksimalne vrijednosti na 5,56, 9,15, 9,79, 11,08, 19,59, 20,25 i 22,16, pri čemu opseg pogreške za 2θ kut svake karakteristične maksimalne vrijednosti je ±0,2,
[image]
2. Kristalni oblik I sukladno patentnom zahtjevu 1, naznačen time što taj kristalni oblik I ima karakteristične maksimalne vrijednosti na 5,56, 9,15, 9,79, 10,29, 11,08, 14,21, 16,61, 19,59, 20,25, 22,16 i 25,69, pri čemu opseg pogreške za 2θ kut svake karakteristične maksimalne vrijednosti je ±0,2.
3. Kristalni oblik I sukladno patentnom zahtjevu 2, naznačen time što taj kristalni oblik I ima karakteristične maksimalne vrijednosti na 5,22, 5,56, 9,15, 9,79, 10,29, 11,08, 13,38, 13,81, 14,21, 14,89, 16,61, 17,19, 18,47, 19,59, 20,25, 22,16, 23,32, 24,67, 25,69, 26,72, 28,73, 29,38, 31,78, 34,02 i 36,95, pri čemu opseg greške za 2θ kut svake karakteristične maksimalne vrijednosti je ±0,2.
4. Postupak dobivanja kristalnog oblika I spoja formule (I) sukladno bilo kojem od patentnih zahtjeva 1 do 3, naznačen time što taj postupak obuhvaća slijedeće korake:
1) postupak I, otapanja spoja iz formule (I) u organskom otapalu da bi se istaložio kristal, filtriranje, pranje i sušenje kristala da bi se dobio željeni kristalni oblik I, pri čemu je organski otapalo izabrano iz skupine koja obuhvaća alkohol, keton, ester, eter, mješovito otapalo etera i alkohola, i mješovito otapalo ketona i vode, alkoholni otapalo se izabire iz skupine koja obuhvaća metanol, etanol i izopropanol, ketonski otapalo je poželjno aceton, estersko otapalo je poželjno etil acetat, etersko otapalo je poželjno tetrahidrofuran/etanol ili tetrahidrofuran/izopropanol, i mješovito otapalo ketona i vode je poželjno aceton/voda;
2) postupak II, dodavanja spoja formule (I) u otapalo, pulpiranje te mješavine, filtriranje i sušenje kristala da bi se dobio željeni kristalni oblik I, pri čemu se organsko otapalo izabire iz skupine koja obuhvaća alkohol, keton, ester, eter, mješovito otapalo etra i alkohola, i mješovito otapalo ketona i vode, alkoholno otapalo se bira iz skupine koja obuhvaća metanol, etanol i izopropanol, ketonsko otapalo je poželjno aceton, estersko otapalo je poželjno etil acetat, etersko otapalo je poželjno tetrahidrofuran, mješovito otapalo etera i alkohola je otapalo ketona i vode je poželjno aceton/voda.
5. Kristalni oblik I sukladno bilo kojem od patentnih zahtjeva 1 do 3, naznačen time što vrijednost maksimalne vrijednosti endotermnog otapanja DSC spektra je od 160°C do 175°C, poželjno od 165°C do 170°C, i još poželjnije 168,17°C.
6. Farmaceutski pripravak koji obuhvaća kristalni oblik I sukladno bilo kojem od patentnih zahtjeva 1 do 3, naznačena time što obuhvaća jedan ili više farmaceutski prihvatljivih nosača, otapala ili ekscipijenasa.
7. Kristalni oblik I spoja formule (I) sukladno bilo kojem od patentnih zahtjeva 1 do 3 ili farmaceutskog pripravka koji obuhvaća kristalni oblik I sukladno patentnom zahtjevu 6 za uporabu u liječenje i/ili sprečavanje bolesti povezane s antagonistom receptora gonadotropin oslobađajućeg hormona (GnRH), pri čemu ta bolest je bolest endokrinog i reproduktivnog sustava.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610999743 | 2016-11-14 | ||
| EP17869463.4A EP3539545B1 (en) | 2016-11-14 | 2017-11-13 | Crystalline form of gnrh receptor antagonist and preparation method therefor |
| PCT/CN2017/110685 WO2018086608A1 (zh) | 2016-11-14 | 2017-11-13 | 一种GnRH受体拮抗剂的结晶形式及其制备方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20211379T1 true HRP20211379T1 (hr) | 2021-12-10 |
Family
ID=62109467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20211379TT HRP20211379T1 (hr) | 2016-11-14 | 2021-08-30 | Kristalni oblik antagonista gnrh receptora i postupak njegovog dobivanja |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US10787451B2 (hr) |
| EP (1) | EP3539545B1 (hr) |
| JP (1) | JP2019535712A (hr) |
| KR (1) | KR102516017B1 (hr) |
| CN (1) | CN108778282B (hr) |
| AU (1) | AU2017357332B2 (hr) |
| BR (1) | BR112019009455A2 (hr) |
| CA (1) | CA3040026A1 (hr) |
| DK (1) | DK3539545T3 (hr) |
| ES (1) | ES2887018T3 (hr) |
| HR (1) | HRP20211379T1 (hr) |
| HU (1) | HUE055891T2 (hr) |
| PL (1) | PL3539545T3 (hr) |
| PT (1) | PT3539545T (hr) |
| TW (1) | TWI774704B (hr) |
| WO (1) | WO2018086608A1 (hr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113993858B (zh) * | 2019-04-30 | 2024-05-28 | 北京泰德制药股份有限公司 | 二氨基嘧啶类化合物或其水合物的固体形式及其制备方法和用途 |
| TW202302592A (zh) * | 2021-04-02 | 2023-01-16 | 大陸商江蘇恒瑞醫藥股份有限公司 | GnRH受體拮抗劑的結晶形式及其製備方法 |
| TW202315622A (zh) * | 2021-08-30 | 2023-04-16 | 大陸商江蘇恆瑞醫藥股份有限公司 | 一種GnRH受體拮抗劑的結晶工藝 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2006220559A1 (en) | 2005-03-07 | 2006-09-14 | Wyeth | Quinoxaline dihydrohalide dihydrates and synthetic methods therefor |
| EP2329823A4 (en) | 2008-09-03 | 2013-04-03 | Takeda Pharmaceutical | METHOD FOR IMPROVING CAPACITY OF PREPARATION TO BE ABSORBED AND PREPARATION WHICH CAPACITY TO BE ABSORBED IS IMPROVED |
| TW201130854A (en) | 2009-12-22 | 2011-09-16 | Bayer Schering Pharma Ag | Pyridinone derivatives and pharmaceutical compositions thereof |
| WO2012175514A1 (en) | 2011-06-21 | 2012-12-27 | Bayer Intellectual Property Gmbh | Pyridinone derivatives and pharmaceutical compositions thereof |
| SI2900675T1 (sl) * | 2012-09-28 | 2019-06-28 | Takeda Pharmaceutical Company Limited | Postopek za pridobivanje tienopirimidin derivata |
| JP6412563B2 (ja) * | 2013-10-30 | 2018-10-24 | シャンハイ ヘンルイ ファーマスーティカル カンパニー リミテッドＳｈａｎｇｈａｉ Ｈｅｎｇｒｕｉ Ｐｈａｒｍａｃｅｕｔｉｃａｌ Ｃｏ．， Ｌｔｄ． | ピラゾロピリミドンまたはピロロトリアゾン誘導体、その製造方法、およびそれらの医薬適用 |
| CN104788435A (zh) * | 2014-01-16 | 2015-07-22 | 江苏恒瑞医药股份有限公司 | 一种蛋白酪氨酸激酶抑制剂的二苯磺酸盐的i型结晶 |
-
2017
- 2017-11-13 KR KR1020197015658A patent/KR102516017B1/ko active IP Right Grant
- 2017-11-13 PL PL17869463T patent/PL3539545T3/pl unknown
- 2017-11-13 CA CA3040026A patent/CA3040026A1/en active Pending
- 2017-11-13 US US16/348,932 patent/US10787451B2/en not_active Expired - Fee Related
- 2017-11-13 CN CN201780017902.8A patent/CN108778282B/zh active Active
- 2017-11-13 BR BR112019009455A patent/BR112019009455A2/pt active Search and Examination
- 2017-11-13 JP JP2019525785A patent/JP2019535712A/ja active Pending
- 2017-11-13 AU AU2017357332A patent/AU2017357332B2/en not_active Ceased
- 2017-11-13 HU HUE17869463A patent/HUE055891T2/hu unknown
- 2017-11-13 EP EP17869463.4A patent/EP3539545B1/en active Active
- 2017-11-13 PT PT178694634T patent/PT3539545T/pt unknown
- 2017-11-13 DK DK17869463.4T patent/DK3539545T3/da active
- 2017-11-13 TW TW106139177A patent/TWI774704B/zh not_active IP Right Cessation
- 2017-11-13 ES ES17869463T patent/ES2887018T3/es active Active
- 2017-11-13 WO PCT/CN2017/110685 patent/WO2018086608A1/zh active Application Filing
-
2021
- 2021-08-30 HR HRP20211379TT patent/HRP20211379T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN108778282A (zh) | 2018-11-09 |
| AU2017357332B2 (en) | 2021-10-28 |
| CN108778282B (zh) | 2021-07-27 |
| WO2018086608A1 (zh) | 2018-05-17 |
| EP3539545A1 (en) | 2019-09-18 |
| EP3539545A4 (en) | 2020-07-01 |
| KR102516017B1 (ko) | 2023-03-30 |
| US10787451B2 (en) | 2020-09-29 |
| AU2017357332A1 (en) | 2019-05-09 |
| TW201817734A (zh) | 2018-05-16 |
| BR112019009455A2 (pt) | 2019-07-30 |
| PL3539545T3 (pl) | 2022-01-10 |
| KR20190080915A (ko) | 2019-07-08 |
| US20190276455A1 (en) | 2019-09-12 |
| TWI774704B (zh) | 2022-08-21 |
| JP2019535712A (ja) | 2019-12-12 |
| DK3539545T3 (da) | 2021-09-27 |
| HUE055891T2 (hu) | 2022-01-28 |
| PT3539545T (pt) | 2021-09-06 |
| CA3040026A1 (en) | 2018-05-17 |
| EP3539545B1 (en) | 2021-08-11 |
| ES2887018T3 (es) | 2021-12-21 |
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