HRP20160178T1 - Novi oblici i soli dihidropirolo[1,2-c]imidazolil inhibitora aldosteron sintaze ili aromataze - Google Patents
Novi oblici i soli dihidropirolo[1,2-c]imidazolil inhibitora aldosteron sintaze ili aromataze Download PDFInfo
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- HRP20160178T1 HRP20160178T1 HRP20160178T HRP20160178T HRP20160178T1 HR P20160178 T1 HRP20160178 T1 HR P20160178T1 HR P20160178 T HRP20160178 T HR P20160178T HR P20160178 T HRP20160178 T HR P20160178T HR P20160178 T1 HRP20160178 T1 HR P20160178T1
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- Prior art keywords
- crystalline form
- salt
- phosphate salt
- degrees
- benzonitrile
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims 7
- 229940123338 Aldosterone synthase inhibitor Drugs 0.000 title 1
- 229940122815 Aromatase inhibitor Drugs 0.000 title 1
- 108010009911 Cytochrome P-450 CYP11B2 Proteins 0.000 title 1
- 102100024329 Cytochrome P450 11B2, mitochondrial Human genes 0.000 title 1
- 239000003886 aromatase inhibitor Substances 0.000 title 1
- 125000002883 imidazolyl group Chemical group 0.000 title 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 13
- 238000000634 powder X-ray diffraction Methods 0.000 claims 10
- 230000001419 dependent effect Effects 0.000 claims 4
- 238000002844 melting Methods 0.000 claims 3
- 230000008018 melting Effects 0.000 claims 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 238000010586 diagram Methods 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 150000002823 nitrates Chemical class 0.000 claims 2
- 208000014311 Cushing syndrome Diseases 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 208000010067 Pituitary ACTH Hypersecretion Diseases 0.000 claims 1
- 208000020627 Pituitary-dependent Cushing syndrome Diseases 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 238000004455 differential thermal analysis Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 201000009395 primary hyperaldosteronism Diseases 0.000 claims 1
- 238000002411 thermogravimetry Methods 0.000 claims 1
Classifications
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- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
- A61P5/46—Drugs for disorders of the endocrine system of the suprarenal hormones for decreasing, blocking or antagonising the activity of glucocorticosteroids
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (15)
1. Fosfatna sol 4-(R)-(6,7-dihidro-5H-pirolo[1,2-c]imidazol-5-il)-3-fluoro-benzonitrila u kristaliničnom obliku A čija rendgenska difrakcija praha (engl. X-ray powder diffraction, XRPD) pokazuje barem jedan ili sve od sljedećih vrhova (pikova), danih kao kut refrakcije 2-theta (θ) vrijednosti, gdje svaki vrh može varirati za ± 0.5 stupnja: 12.9, 16.3 i 20.4 stupnja; gdje se XRPD može utvrditi uporabom sljedećih parametara i uređaja:
[image]
2. Fosfatna sol 4-(R)-(6,7-dihidro-5H-pirolo[1,2-c]imidazol-5-il)-3-fluoro-benzonitrila u kristaliničnom obliku prema zahtjevu 1, s molarnim omjerom 4-(R)-(6,7-dihidro-5H-pirolo[1,2-c]imidazol-5-il)-3-fluoro-benzonitrila prema fosfatu od oko 1:1.
3. Fosfatna sol u kristaliničnom obliku A prema zahtjevu 2 čije je talište barem 50°C više od onoga slobodne baze.
4. Fosfatna sol u kristaliničnom obliku A prema zahtjevu 3 čije je talište, uporabom termogravimetrijske/diferencijalne termalne analize (TG/DTA), između 209 i 212°C.
5. Kristalinični oblik A fosfatne soli prema zahtjevu 1 ili bilo kojem od o njemu ovisnih zahtjeva čije je talište 210±0.5°C, utvrđeno putem TG/DTA.
6. Kristalinični oblik A fosfatne soli prema zahtjevu 1 ili bilo kojem od o njemu ovisnih zahtjeva čiji XRPD pokazuje barem jedan ili sve od sljedećih vrhova, danih kao kut refrakcije 2-theta (θ) vrijednosti, gdje svaki vrh može varirati za ± 0.2 stupnja: 12.9, 16.3 i 20.4 stupnja.
7. Kristalinični oblik A fosfatne soli prema zahtjevu 1 ili bilo kojem od zahtjeva 2 do 5 čiji XRPD pokazuje barem 4, 5, 6, 7, 8, 9 ili sve od sljedećih vrhova, danih kao kut refrakcije 2-theta (θ) vrijednosti, gdje svaki vrh može varirati za ± 0.5, posebno ± 0.2 stupnja: 6.0, 12.9, 15.5, 16.0, 16.3, 19.7, 20.4, 22.1, 24.3 i 29.2 stupnja.
8. Kristalinični oblik A fosfatne soli prema zahtjevu 1 ili bilo kojem od zahtjeva 2 do 5 čiji XRPD pokazuje barem 7, 9, 11, 13, 15, 17 ili sve od sljedećih vrhova, gdje svaki vrh može varirati za ± 0.5, posebno ± 0.2 stupnja: 6.0, 10.0, 12.1, 12.9, 14.0, 14.5, 15.5, 16.0, 16.3, 17.5, 18.2, 18.4, 19.7, 20.4, 22.1, 24.3, 29.2.
9. Kristalinični oblik A fosfatne soli prema zahtjevu 1 ili bilo kojem od o njemu ovisnih zahtjeva 2 do 5, 7 ili 8, gdje dva najveća vrha u XRPD dijagramu imaju relativni intenzitet od 1 do 0.5 do 0.7, posebno od 1 do 0,55 do 0.65, još posebnije od 0.57 do 0.61, npr. od 1 do 0.59 (može se dobiti integracijom svakog od vrhova u XRPD dijagramima), posebno je veći vrh na 2-theta (θ) vrijednosti od 6.0 ± 0.5, posebno ± 0.2 stupnja i manji vrh na 2-theta (θ) vrijednosti od 19.7 ± 0.5, odnosno posebno ± 0.2 stupnja.
10. Kristalinični oblik A fosfatne soli prema zahtjevu 1 ili bilo kojem od o njemu ovisnih zahtjeva čiji je XRPD kako je prikazan na Slici 1-A.
11. Nitratna sol 4-(R)-6,7-dihidro-5H-pirolo[1,2-c]imidazol-5-il-3-fluoro-benzonitrila.
12. Postupak pripreme nitratne ili fosfatne soli u kristaliničnom obliku A, kako je definirano u zahtjevu 1, 4-(R)-6,7-dihidro-5Hpirolo[1,2-c]imidazol-5-il-3-fluoro-benzonitrila, postupak obuhvaća:
(a) uporaba otopine 4-(R)-6,7-dihidro-5H-pirolo[1,2-c]imidazol-5-il-3-fluoro-benzonitrila u ili protonskom ili aprotonskom polarnom otapalu;
(b) dodavanje nitratne kiseline ili posebno fosforne kiseline; i
(c) izoliranje nastalog kristaliničnog oblika nitratne soli ili posebno fosfatne soli 4-(R)-6,7-dihidro-5Hpirolo[1,2-c]imidazol-5-il-3-fluoro-benzonitrila.
13. Sol ili oblik soli prema bilo kojem od zahtjeva 1 do 11 za uporabu u proizvodnji lijeka za liječenje Cushingovog sindroma.
14. Sol ili oblik soli prema bilo kojem od zahtjeva 1 do 11 ili farmaceutski pripravak koji sadrži tu sol ili oblik soli za uporabu u liječenju Cushingove bolesti.
15. Farmaceutski pripravak koji sadrži fosfatnu sol 4-(R)-(6,7-dihidro-5H-pirolo[1,2-c]imidazol-5-il)-3-fluoro-benzonitrila u kristaliničnom obliku prema bilo kojem od zahtjeva 1 do 10 i jednu ili više farmaceutski prikladnih pomoćnih tvari.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201261587280P | 2012-01-17 | 2012-01-17 | |
EP13701194.6A EP2804863B1 (en) | 2012-01-17 | 2013-01-15 | New forms and salts of a dihydropyrrolo[1,2-c]imidazolyl aldosterone synthase or aromatase inhibitor |
PCT/US2013/021521 WO2013109514A1 (en) | 2012-01-17 | 2013-01-15 | New forms and salts of a dihydropyrrolo[1,2-c]imidazolyl aldosterone synthase or aromatase inhibitor |
Publications (1)
Publication Number | Publication Date |
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HRP20160178T1 true HRP20160178T1 (hr) | 2016-03-25 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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HRP20160178T HRP20160178T1 (hr) | 2012-01-17 | 2016-02-19 | Novi oblici i soli dihidropirolo[1,2-c]imidazolil inhibitora aldosteron sintaze ili aromataze |
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Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101412206B1 (ko) * | 2010-01-14 | 2014-06-25 | 노파르티스 아게 | 부신 호르몬 조절제의 용도 |
EP2815749A1 (en) | 2013-06-20 | 2014-12-24 | IP Gesellschaft für Management mbH | Solid form of 4-amino-2-(2,6-dioxopiperidine-3-yl)isoindoline-1,3-dione having specified X-ray diffraction pattern |
JP6731136B2 (ja) | 2014-07-07 | 2020-07-29 | レコルダティ アーゲー | 医薬製剤 |
HUE054248T2 (hu) | 2015-01-29 | 2021-08-30 | Recordati Ag | Eljárás kondenzált imidazo-származékok elõállítására |
US20160287565A1 (en) * | 2015-04-06 | 2016-10-06 | Millendo Therapeutics, Inc. | Combination therapy for treating disorders associated with excess cortisol production |
WO2018078049A1 (en) * | 2016-10-27 | 2018-05-03 | Damian Pharma Ag | Aldosterone synthase inhibitor |
KR102506380B1 (ko) * | 2016-10-27 | 2023-03-03 | 다미안 파르마 에이쥐 | 알도스테론 합성효소 저해제 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
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US1315449A (en) * | 1918-11-15 | 1919-09-09 | Frank B Yingling | Shaper-feed. |
US4617307A (en) * | 1984-06-20 | 1986-10-14 | Ciba-Geigy Corporation | Substituted imidazo[1,5-A]pyridine derivatives as aromatase inhibitors |
US5066656A (en) | 1989-11-01 | 1991-11-19 | Janssen Pharmaceutica N.V. | Pharmacologically active (6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)- and (5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl) substituted 1H-benzotriazole derivatives |
MTP1076B (en) * | 1990-01-12 | 1991-09-30 | Ciba Geigy Ag | Hemihydrate |
AU668708B2 (en) | 1992-01-27 | 1996-05-16 | Janssen Pharmaceutica N.V. | Pyrroloimidazolyl and imidazopyridinyl substituted 1H-benzimidazole derivatives |
JP2006508970A (ja) * | 2002-11-18 | 2006-03-16 | ノバルティス アクチエンゲゼルシャフト | イミダゾ[1,5a]ピリジン誘導体およびアルデステロンにより仲介される疾患の処置方法 |
GT200600381A (es) | 2005-08-25 | 2007-03-28 | Compuestos organicos | |
WO2008076862A2 (en) | 2006-12-18 | 2008-06-26 | Novartis Ag | 1-substituted imidazole derivatives and their use as aldosterone synthase inhibitors |
JP5575913B2 (ja) | 2009-11-30 | 2014-08-20 | ノバルティス アーゲー | アルドステロン合成酵素阻害剤としてのイミダゾール誘導体 |
KR101412206B1 (ko) * | 2010-01-14 | 2014-06-25 | 노파르티스 아게 | 부신 호르몬 조절제의 용도 |
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