HRP20140558T1 - Novi postupci za proizvodnju derivata benzofenona - Google Patents
Novi postupci za proizvodnju derivata benzofenona Download PDFInfo
- Publication number
- HRP20140558T1 HRP20140558T1 HRP20140558AT HRP20140558T HRP20140558T1 HR P20140558 T1 HRP20140558 T1 HR P20140558T1 HR P20140558A T HRP20140558A T HR P20140558AT HR P20140558 T HRP20140558 T HR P20140558T HR P20140558 T1 HRP20140558 T1 HR P20140558T1
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- HR
- Croatia
- Prior art keywords
- compound
- formula
- preparation
- followed
- iii
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 30
- 150000008366 benzophenones Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 18
- 238000002360 preparation method Methods 0.000 claims 10
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims 3
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- -1 quaternary ammonium halide Chemical class 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 229910003074 TiCl4 Inorganic materials 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000005587 carbonate group Chemical group 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 150000002148 esters Chemical group 0.000 claims 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000004128 high performance liquid chromatography Methods 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910001507 metal halide Inorganic materials 0.000 claims 1
- 150000005309 metal halides Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 235000009518 sodium iodide Nutrition 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
-
- 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
- A61P15/12—Drugs for genital or sexual disorders; Contraceptives for climacteric disorders
-
- 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
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/30—Oestrogens
-
- 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
- C07C45/68—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 by increase in the number of carbon atoms
- C07C45/72—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 by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
Claims (15)
1. Postupak za pripravu spoja formule I,
[image]
gdje:
X predstavlja halo ili -OH;
R1 predstavlja H ili C1-6 alkil nesupstituiran ili supstituiran sa jednom ili više -OH skupina; svaki R2a, R2b, R2c, R2d, R2e, R3a, R3b, R3c, R3d i R3e nezavisno predstavlja H ili -OH;
koji postupak sadrži reakciju spoja formule II,
[image]
gdje R1 i R3a, R3b, R3c, R3d i R30 su kao gore definirani, sa spojem formule III,
[image]
gdje X i R2a, R2b, R2c, R2di R2e su kao gore definirani.
2. Postupak prema patentnom zahtjevu 1, gdje:
X predstavlja klor; i/ili
R2 predstavlja H, i/ili R2a, R2b, R2c, R2d, R2B, R3e, R3b, R3c, R3d i R3' svi predstavljaju H.
3. Postupak prema bilo kojem od patentnih zahtjeva 1 ili 2, gdje:
spoj formule I ima Z:E omjer geometrijskih izomera veći od 4:1; postupak se provodi u odsustvu otapala ili u prisutnosti 2-metiltetrahidrofurana; i/ili postupak se provodi u prisutnosti spoja titanij klorida i reducirajućeg agensa, opcionalno pri čemu su spoj titanij klorida i reducirajući agens TiCl4 i cink.
4. Postupak prema bilo kojem od prethodnih patentnih zahtjeva, pri čemu je molarni omjer spojeva formula II i III u postupku izuma je oko 1:1 i/ili molarni ekvivalent spoja titanij klorida prema spoju formule II ili III je 1.3:1.
5. Postupak za izolaciju/ pročišćavanje spoja formule I, kao što je definiran u patentnom zahtjevu 1, koji postupak sadrži pripremu spoja formule 1 postupkom prema bilo kojem od patentnih zahtjeva 1 do 4, nakon čega slijedi kristalizacija ili precipitacija spoja, u sustavu otapala.
6. Postupak prema patentnom zahtjevu 5, pri čemu sustav otapala sadrži alkohol, opcionalno pomiješan s vodom.
7. Postupak prema patentnom zahtjevu 5 ili 6, pri čemu je spoj formule 1 dobiven u Z:E omjeru većem od 10:1 i/ili sa HPLC čistoćom većom od 95%.
8. Postupak za pripravu spoja formule I u kojem R1 predstavlja H prema bilo kojem od patentnih zahtjeva 1 do 7, koji prvo sadrži pripremu spoja formula II kao što je definiran u patentnom zahtjevu 1 ali u kojem R1 predstavlja H, koji sadrži reakciju spoja formule IV,
[image]
gdje R3a do R3e su kao što je definirano u patentnom zahtjevu 1 ili 2, sa etilen karbonatom, u prisutnosti katalizatora, i naznačen time da se reakcija provodi u prisutnosti manje od 1 grama otapala po gramu etilen karbonata.
9. Postupak prema patentnom zahtjevu 8, koji se provodi u prisutnosti toluena ili ksilena.
10. Postupak prema patentnom zahtjevu 8 ili 9, pri čemu je katalizator karbonat, metalni halid, kvarterni amonij halid ili kvarterni fosfor halid, ili njihove smjese.
11. Postupak prema patentnom zahtjevu 10, pri čemu je katalizator natrij ili kalij jodid.
12. Postupak za pripravu spoja formule 1 kao što je definiran u bilo kojem od patentnih zahtjeva 1 ili 2, koji postupak sadrži:
(i) postupak za pripravu spoja formule II prema bilo kojem od patentnih zahtjeva 8 do 11;
(ii) postupak za pripravu spoja formule I prema bilo kojem od patentnih zahtjeva 1 do 4, pri čemu je spoj formule II dobiven postupkom gore opisanog koraka (i); i, opcionalno,
(iii) izoliranje spoja formule I dobivenog gornjim korakom (ii) prema postupku opisanom u patentnom zahtjevu 5, 6 ili 7.
13. Postupak za pripravu spoja formule I kao što je definiran u patentnom zahtjevu 1 ali u kojem R1 predstavlja C1-6 alkil terminalno supstituiran sa -OH skupinom, koji sadrži pripremu spoja formule I u kojem R1 predstavlja H nakon čega slijedi reakcija spoja formule VII,
X3-R1b-C(O)OR1c VII
gdje X3 predstavlja prikladnu odlaznu skupinu, R1b predstavlja C1-5 alkil, te R1c predstavlja opcionalno supstituirani C1-6 alkil, nakon čega slijedi redukcija esternog dijela u -CH2-OH dio.
14. Postupak za pripravu farmaceutskog pripravka koji sadrži spoj formule I, ili njegovu sol, koji proces je naznačen time da uključuje kao korak postupak prema bilo kojem od patentnih zahtjeva 1 do 9 ili 13.
15. Postupak za pripravu farmaceutskog pripravka prema patentnom zahtjevu 14, pri čemu nakon postupka slijedi korak spajanja spoja formule I ili njegove soli nastalog postupkom, sa jednim ili više farmaceutski prihvatljivih ekscipijensa, adjuvansa, razrjeđivača ili nosača.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29609610P | 2010-01-19 | 2010-01-19 | |
| PCT/GB2011/000058 WO2011089385A1 (en) | 2010-01-19 | 2011-01-19 | New processes for producing benzophenone derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20140558T1 true HRP20140558T1 (hr) | 2014-08-01 |
Family
ID=43827282
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20140558AT HRP20140558T1 (hr) | 2010-01-19 | 2014-06-11 | Novi postupci za proizvodnju derivata benzofenona |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US9085519B2 (hr) |
| EP (1) | EP2526080B1 (hr) |
| JP (1) | JP5850857B2 (hr) |
| CN (1) | CN102770402B (hr) |
| BR (1) | BR112012017845A2 (hr) |
| DK (1) | DK2526080T3 (hr) |
| ES (1) | ES2460022T3 (hr) |
| HK (1) | HK1179244A1 (hr) |
| HR (1) | HRP20140558T1 (hr) |
| PL (1) | PL2526080T3 (hr) |
| PT (1) | PT2526080E (hr) |
| RS (1) | RS53353B (hr) |
| SI (1) | SI2526080T1 (hr) |
| WO (1) | WO2011089385A1 (hr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150321983A1 (en) * | 2012-10-19 | 2015-11-12 | Fermion Oy | A process for the preparation of ospemifene |
| WO2014060639A1 (en) | 2012-10-19 | 2014-04-24 | Fermion Oy | A process for the preparation of ospemifene |
| CN104030896A (zh) * | 2013-03-07 | 2014-09-10 | 天津药物研究院 | 一种简易去除欧司哌米芬特异杂质的方法 |
| CN107074722A (zh) * | 2014-09-16 | 2017-08-18 | 盐野义制药株式会社 | 三苯基丁烯衍生物的制造方法 |
| EP3240771B1 (en) | 2014-12-29 | 2019-02-20 | OLON S.p.A. | Process for the preparation of ospemifene and fispemifene |
| US10138190B2 (en) | 2015-01-09 | 2018-11-27 | Glenmark Pharmaceuticals Limited | Process for preparation of ospemifene |
| EP3390338A1 (de) * | 2015-12-15 | 2018-10-24 | Basf Se | Verfahren zur herstellung von hydroxybenzophenonpolyglykolether-(meth)acrylat |
| EP3835285A1 (en) | 2016-03-15 | 2021-06-16 | Shionogi & Co., Ltd | Method for producing phenoxyethanol derivative |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2182786A (en) | 1938-09-14 | 1939-12-12 | Dow Chemical Co | Hydroxy-alkyl ethers of benzophenone |
| US2831768A (en) | 1956-01-19 | 1958-04-22 | Eastman Kodak Co | Polymeric light-sensitive photographic elements |
| CS196471B1 (cs) | 1977-11-28 | 1980-03-31 | Ivan Lukac | Nové p-acylované fenoxyetanoly |
| DE3272723D1 (en) | 1981-08-17 | 1986-09-25 | Hoffmann La Roche | Carbamic esters, preparation thereof, pesticidal compositions on the basis of these compounds and their use in combating pests |
| GB2126576B (en) | 1982-06-25 | 1985-06-19 | Farmos Group Limited | Alkane and alkene derivatives |
| US4625048A (en) | 1982-08-13 | 1986-11-25 | Hoffmann-La Roche Inc. | Carbamic acid esters |
| DE3814781A1 (de) * | 1988-04-30 | 1989-11-09 | Basf Ag | Verfahren zur herstellung von 2-hydroxy-4-(2'-hydroxyethoxy)-benzophenonen |
| DE3936592A1 (de) * | 1989-11-03 | 1991-05-08 | Basf Ag | Verfahren zur herstellung und reinigung von 2-hydroxy-4-(2'-hydroxy-ethoxy)phenylarylketonen |
| GB9418067D0 (en) * | 1994-09-07 | 1994-10-26 | Orion Yhtymae Oy | Triphenylethylenes for the prevention and treatment of osteoporosis |
| GB9803521D0 (en) | 1998-02-19 | 1998-04-15 | Orion Yhtymo Oy | New compounds and pharmaceutical compositions thereof |
| TW593256B (en) * | 1999-11-16 | 2004-06-21 | Hormos Medical Oy Ltd | Triphenylalkene derivatives and their use as selective estrogen receptor modulators |
| ATE272600T1 (de) | 2000-02-17 | 2004-08-15 | Appleton Paper Inc | Verfahren zur herstellung von alkoxy- oder arylmethoxy-aroxyethanen |
| WO2008099060A2 (en) | 2007-02-14 | 2008-08-21 | Hormos Medical Ltd | Methods for the preparation of fispemifene from ospemifene |
| CN101636372B (zh) * | 2007-02-14 | 2013-03-27 | 霍尔莫斯医疗有限公司 | 有治疗价值的三苯基丁烯衍生物的制备方法 |
-
2011
- 2011-01-19 DK DK11702677.3T patent/DK2526080T3/da active
- 2011-01-19 JP JP2012549409A patent/JP5850857B2/ja not_active Expired - Fee Related
- 2011-01-19 RS RS20140242A patent/RS53353B/en unknown
- 2011-01-19 ES ES11702677.3T patent/ES2460022T3/es active Active
- 2011-01-19 CN CN201180006347.1A patent/CN102770402B/zh not_active Expired - Fee Related
- 2011-01-19 WO PCT/GB2011/000058 patent/WO2011089385A1/en active Application Filing
- 2011-01-19 US US13/521,910 patent/US9085519B2/en not_active Expired - Fee Related
- 2011-01-19 BR BR112012017845A patent/BR112012017845A2/pt not_active IP Right Cessation
- 2011-01-19 PT PT117026773T patent/PT2526080E/pt unknown
- 2011-01-19 PL PL11702677T patent/PL2526080T3/pl unknown
- 2011-01-19 EP EP11702677.3A patent/EP2526080B1/en active Active
- 2011-01-19 SI SI201130174T patent/SI2526080T1/sl unknown
-
2013
- 2013-05-28 HK HK13106352.4A patent/HK1179244A1/xx not_active IP Right Cessation
-
2014
- 2014-06-11 HR HRP20140558AT patent/HRP20140558T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN102770402B (zh) | 2016-01-20 |
| BR112012017845A2 (pt) | 2016-03-29 |
| PT2526080E (pt) | 2014-05-06 |
| WO2011089385A1 (en) | 2011-07-28 |
| EP2526080A1 (en) | 2012-11-28 |
| US9085519B2 (en) | 2015-07-21 |
| EP2526080B1 (en) | 2014-03-26 |
| US20130035514A1 (en) | 2013-02-07 |
| RS53353B (en) | 2014-10-31 |
| SI2526080T1 (sl) | 2014-07-31 |
| CN102770402A (zh) | 2012-11-07 |
| DK2526080T3 (da) | 2014-04-28 |
| JP2013517320A (ja) | 2013-05-16 |
| ES2460022T3 (es) | 2014-05-13 |
| PL2526080T3 (pl) | 2014-08-29 |
| HK1179244A1 (en) | 2013-09-27 |
| JP5850857B2 (ja) | 2016-02-03 |
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