HRP20120504T1 - Novi postupak izomeriziranja kondenziranih bicikličkih i dobivanja analoga vitamina d koji ih sadrže - Google Patents
Novi postupak izomeriziranja kondenziranih bicikličkih i dobivanja analoga vitamina d koji ih sadrže Download PDFInfo
- Publication number
- HRP20120504T1 HRP20120504T1 HRP20120504AT HRP20120504T HRP20120504T1 HR P20120504 T1 HRP20120504 T1 HR P20120504T1 HR P20120504A T HRP20120504A T HR P20120504AT HR P20120504 T HRP20120504 T HR P20120504T HR P20120504 T1 HRP20120504 T1 HR P20120504T1
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- derivative
- cis
- condensed bicyclic
- same
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 19
- 125000002619 bicyclic group Chemical group 0.000 title claims abstract 12
- 229940046008 vitamin d Drugs 0.000 title claims 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract 6
- 125000003118 aryl group Chemical group 0.000 claims abstract 2
- 229910052805 deuterium Inorganic materials 0.000 claims abstract 2
- 125000004431 deuterium atom Chemical group 0.000 claims abstract 2
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- 125000005842 heteroatom Chemical group 0.000 claims abstract 2
- 150000004678 hydrides Chemical class 0.000 claims abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 150000003338 secosteroids Chemical class 0.000 claims 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 238000000746 purification Methods 0.000 claims 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 229930003316 Vitamin D Natural products 0.000 claims 1
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 claims 1
- 238000007239 Wittig reaction Methods 0.000 claims 1
- 125000005024 alkenyl aryl group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 238000004440 column chromatography Methods 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 150000001934 cyclohexanes Chemical class 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 239000012156 elution solvent Substances 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- BUDPDEVHCQIFNU-PUBYVPDWSA-N inecalcitol Chemical compound C1(/[C@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CC#CC(C)(C)O)C)=C/C=C1/C[C@@H](O)C[C@H](O)C1=C BUDPDEVHCQIFNU-PUBYVPDWSA-N 0.000 claims 1
- 229950003028 inecalcitol Drugs 0.000 claims 1
- 238000006317 isomerization reaction Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 229910052710 silicon Inorganic materials 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 150000003431 steroids Chemical class 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- -1 vinyl halide Chemical class 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 235000019166 vitamin D Nutrition 0.000 claims 1
- 239000011710 vitamin D Substances 0.000 claims 1
- 150000003710 vitamin D derivatives Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C401/00—Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/613—Unsaturated compounds containing a keto groups being part of a ring polycyclic
- C07C49/617—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system
- C07C49/623—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system having two rings
- C07C49/633—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system having two rings the condensed ring system containing eight or nine carbon atoms
-
- 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
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/24—All rings being cycloaliphatic the ring system containing nine carbon atoms, e.g. perhydroindane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
Postupak dobivanja cis kondenziranog bicikličkog derivata iz odgovarajućeg trans kondenziranog bicikličkog derivata gdje se navedeni postupak sastoji u koraku reakcije navedenog trans kondenziranog bicikličkog derivat s hidridnom bazom naznačen time što navedene trans i cis kondenzirane bicikličke strukture imaju formulu I odnosno II gdjeR predstavlja H ili C C alkilnu skupinu R predstavlja H ili D gdje D predstavlja atom deuterija R predstavlja C C alkil koji izborno sadrži jednu ili više dvostrukih ili trostrukih vezai ili izborno sadrži jedan ili više heteroatoma koje se bira između O N S Si m je cijeli broj kojeg se bira između n je cijeli broj kojeg se bira između ili kada su prisutni svaki od Ri i Rj bilo da su isti ili različiti predstavlja do m odnosno do n skupina koje su bilo iste ili međusobno različite i neovisno ih se bira između atoma halogena C C alkila C C alkenila OR NRR CN NO perhalogen C C alkila COR COOR CONRR alkilarila alkenilarila gdje se R R bilo da su isti ili različitibira između H alkila i arila Patent sadrži još patentnih zahtjeva
Claims (13)
1. Postupak dobivanja cis kondenziranog bicikličkog derivata iz odgovarajućeg trans kondenziranog bicikličkog derivata, gdje se navedeni postupak sastoji u koraku reakcije navedenog trans kondenziranog bicikličkog derivat s hidridnom bazom, naznačen time što navedene trans i cis kondenzirane bicikličke strukture imaju formulu (I) odnosno (II):
[image]
gdje:
– R1 predstavlja H ili C1-C6 alkilnu skupinu;
– R2 predstavlja H ili D;
gdje D predstavlja atom deuterija;
– R3 predstavlja C1-C20 alkil, koji izborno sadrži jednu ili više dvostrukih ili trostrukih veza i/ili izborno sadrži jedan ili više heteroatoma, koje se bira između O, N, S, Si;
– m je cijeli broj, kojeg se bira između 0, 1, 2, 3;
– n je cijeli broj, kojeg se bira između 0, 1 ili 2;
– kada su prisutni, svaki od Ri i Rj, bilo da su isti ili različiti, predstavlja 1 do m odnosno 1 do n skupina, koje su bilo iste ili međusobno različite, i neovisno ih se bira između atoma halogena, C1-C6 alkila, C2-C6 alkenila, OR, NRR', CN, NO2, perhalogen(C1-C6)alkila, COR, COOR, CONRR', alkilarila, alkenilarila, gdje se R, R', bilo da su isti ili različiti, bira između H, alkila i arila.
2. Postupak u skladu s patentnim zahtjevom 1, naznačen time što m = n = 0, R1 = metil, R2 = H; i/ili R3 ima formulu:
[image]
gdje X je H, ili je X zaštitna skupina za funkcionalnu skupinu OH, a prekinuta veza
[image]
je veza na ciklopentilnu jezgru.
3. Postupak u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što je navedena baza formule M-H, gdje je M atom iz skupine IA.
4. Postupak u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što je navedena baza NaH.
5. Postupak u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što se navedeni korak provodi u otapalu, kojeg se bira između THF ili alkiliranog THF.
6. Postupak u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što se dodatno sastoji u koraku hidrolize, kojeg se provodi nakon gore navedenog koraka izomeriziranja.
7. Postupak u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što se dodatno sastoji u pročišćavanju dobivenog cis kondenzirani biciklički derivat.
8. Postupak u skladu s patentnim zahtjevom 7, naznačen time što se navedeno pročišćavanje provodi kromatografijom na stupcu.
9. Postupak u skladu s patentnim zahtjevom 8, naznačen time što je elucijsko otapalo smjesa heptana i etil-acetata.
10. Postupak dobivanja steroidnog ili sekosteroidnog derivata koji sadrži cis spregu između prstena C i D, naznačen time što se navedeni postupak sastoji u postupku dobivanja cis kondenziranog bicikličkog derivata iz odgovarajućeg trans kondenziranog bicikličkog derivata u skladu s bilo kojim od prethodnih patentnih zahtjeva.
11. Postupak u skladu s patentnim zahtjevom 10, naznačen time što je navedeni sekosteroid analog vitamina D, formule (III):
[image]
.
12. Postupak u skladu s patentnim zahtjevom 10 ili 11, naznačen time što je navedeni sekosteroid inekalcitol formule:
[image]
.
13. Postupak u skladu s patentnim zahtjevom 10, 11 ili 12, naznačen time što se dodatno sastoji u koracima:
– provođenja Wittigove reakcije, čime se dobiva vinil-halogenidni derivat;
– kondenzacije dobivenog spoja s odgovarajućim cikloheksanskim derivatom ili njegovim pretečom; i izborno
– hidrolize dobivenog spoja.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10305088A EP2360145B1 (en) | 2010-01-26 | 2010-01-26 | New process for isomerizing fused bicyclic structures and preparation of vitamin D analogs comprising the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20120504T1 true HRP20120504T1 (hr) | 2012-07-31 |
Family
ID=41733123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20120504AT HRP20120504T1 (hr) | 2010-01-26 | 2012-06-18 | Novi postupak izomeriziranja kondenziranih bicikličkih i dobivanja analoga vitamina d koji ih sadrže |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US9315455B2 (hr) |
| EP (2) | EP2360145B1 (hr) |
| JP (1) | JP5730591B2 (hr) |
| KR (1) | KR101707016B1 (hr) |
| CN (1) | CN102190570B (hr) |
| AR (1) | AR081799A1 (hr) |
| AT (1) | ATE550318T1 (hr) |
| AU (1) | AU2011200154B2 (hr) |
| BR (1) | BRPI1100778A2 (hr) |
| CA (1) | CA2729360C (hr) |
| DK (1) | DK2360145T3 (hr) |
| ES (1) | ES2384700T3 (hr) |
| HR (1) | HRP20120504T1 (hr) |
| IL (1) | IL210672A0 (hr) |
| NZ (1) | NZ590702A (hr) |
| PL (1) | PL2360145T3 (hr) |
| PT (1) | PT2360145E (hr) |
| RU (1) | RU2560184C2 (hr) |
| SG (1) | SG173291A1 (hr) |
| SI (1) | SI2360145T1 (hr) |
| TW (1) | TWI494298B (hr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT2360145E (pt) | 2010-01-26 | 2012-06-27 | Hybrigenics Sa | Novo processo para isomerização de estruturas bicíclicas condensadas e preparação de análogos de vitamina d que as contêm |
| CN110330522A (zh) * | 2019-07-29 | 2019-10-15 | 南京海融医药科技股份有限公司 | 一种帕立骨化醇异构体杂质py5的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69433220T2 (de) * | 1993-07-09 | 2004-08-19 | Laboratoire Theramex | Neue strukturelle Vitamin D Derivate |
| GB9611603D0 (en) * | 1996-06-04 | 1996-08-07 | Leo Pharm Prod Ltd | Chemical compounds |
| US6191292B1 (en) | 1999-12-08 | 2001-02-20 | Laboratoire Theramex | Precursors of the A-ring of vitamin D and method and intermediates for the preparation thereof |
| GB0423091D0 (en) * | 2004-10-19 | 2004-11-17 | Leuven K U Res & Dev | Bioactive vitamin d analogues |
| US7414158B2 (en) | 2006-07-24 | 2008-08-19 | The Procter & Gamble Company | Process for epimerising cyclohexenyl ketones and its application in Aldol condensation process |
| MX2011012330A (es) | 2009-05-20 | 2011-12-16 | Hybrigenics Sa | Nuevos usos terapeuticos de inecalcitol. |
| PT2360145E (pt) | 2010-01-26 | 2012-06-27 | Hybrigenics Sa | Novo processo para isomerização de estruturas bicíclicas condensadas e preparação de análogos de vitamina d que as contêm |
-
2010
- 2010-01-26 PT PT10305088T patent/PT2360145E/pt unknown
- 2010-01-26 PL PL10305088T patent/PL2360145T3/pl unknown
- 2010-01-26 DK DK10305088.6T patent/DK2360145T3/da active
- 2010-01-26 ES ES10305088T patent/ES2384700T3/es active Active
- 2010-01-26 AT AT10305088T patent/ATE550318T1/de active
- 2010-01-26 EP EP10305088A patent/EP2360145B1/en not_active Not-in-force
- 2010-01-26 SI SI201030042T patent/SI2360145T1/sl unknown
-
2011
- 2011-01-14 AU AU2011200154A patent/AU2011200154B2/en not_active Ceased
- 2011-01-16 IL IL210672A patent/IL210672A0/en active IP Right Grant
- 2011-01-20 CA CA2729360A patent/CA2729360C/en not_active Expired - Fee Related
- 2011-01-24 BR BRPI1100778-8A patent/BRPI1100778A2/pt not_active Application Discontinuation
- 2011-01-24 KR KR1020110006777A patent/KR101707016B1/ko not_active Expired - Fee Related
- 2011-01-24 US US13/012,084 patent/US9315455B2/en not_active Expired - Fee Related
- 2011-01-25 NZ NZ590702A patent/NZ590702A/en not_active IP Right Cessation
- 2011-01-25 AR ARP110100229A patent/AR081799A1/es not_active Application Discontinuation
- 2011-01-25 JP JP2011012797A patent/JP5730591B2/ja not_active Expired - Fee Related
- 2011-01-25 TW TW100102697A patent/TWI494298B/zh not_active IP Right Cessation
- 2011-01-25 SG SG2011005386A patent/SG173291A1/en unknown
- 2011-01-25 RU RU2011102734/04A patent/RU2560184C2/ru not_active IP Right Cessation
- 2011-01-25 EP EP11151947A patent/EP2360146A1/en not_active Ceased
- 2011-01-26 CN CN201110051111.1A patent/CN102190570B/zh not_active Expired - Fee Related
-
2012
- 2012-06-18 HR HRP20120504AT patent/HRP20120504T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2360145A1 (en) | 2011-08-24 |
| EP2360145B1 (en) | 2012-03-21 |
| TW201141825A (en) | 2011-12-01 |
| DK2360145T3 (da) | 2012-07-09 |
| BRPI1100778A2 (pt) | 2012-07-24 |
| RU2011102734A (ru) | 2012-07-27 |
| ATE550318T1 (de) | 2012-04-15 |
| KR20110088406A (ko) | 2011-08-03 |
| AR081799A1 (es) | 2012-10-24 |
| TWI494298B (zh) | 2015-08-01 |
| JP5730591B2 (ja) | 2015-06-10 |
| SI2360145T1 (sl) | 2012-08-31 |
| EP2360146A1 (en) | 2011-08-24 |
| US9315455B2 (en) | 2016-04-19 |
| US20110184198A1 (en) | 2011-07-28 |
| AU2011200154A1 (en) | 2011-08-11 |
| RU2560184C2 (ru) | 2015-08-20 |
| SG173291A1 (en) | 2011-08-29 |
| PL2360145T3 (pl) | 2012-08-31 |
| CA2729360C (en) | 2018-01-02 |
| PT2360145E (pt) | 2012-06-27 |
| NZ590702A (en) | 2012-06-29 |
| CA2729360A1 (en) | 2011-07-26 |
| CN102190570B (zh) | 2014-10-15 |
| IL210672A0 (en) | 2011-08-01 |
| CN102190570A (zh) | 2011-09-21 |
| KR101707016B1 (ko) | 2017-02-15 |
| ES2384700T3 (es) | 2012-07-11 |
| AU2011200154B2 (en) | 2015-09-17 |
| JP2011153140A (ja) | 2011-08-11 |
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