HRP20100102T1 - 17alfa-CIJANOMETIL-17beta-HIDROKSI-ESTRA-4,9-DIEN-3-ON VISOKE ČISTOĆE I POSTUPAK NJEGOVE SINTEZE - Google Patents
17alfa-CIJANOMETIL-17beta-HIDROKSI-ESTRA-4,9-DIEN-3-ON VISOKE ČISTOĆE I POSTUPAK NJEGOVE SINTEZE Download PDFInfo
- Publication number
- HRP20100102T1 HRP20100102T1 HR20100102T HRP20100102T HRP20100102T1 HR P20100102 T1 HRP20100102 T1 HR P20100102T1 HR 20100102 T HR20100102 T HR 20100102T HR P20100102 T HRP20100102 T HR P20100102T HR P20100102 T1 HRP20100102 T1 HR P20100102T1
- Authority
- HR
- Croatia
- Prior art keywords
- formula
- accordance
- above requirements
- reaction
- carried out
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 16
- 230000015572 biosynthetic process Effects 0.000 title claims abstract 3
- 238000003786 synthesis reaction Methods 0.000 title claims abstract 3
- 238000006243 chemical reaction Methods 0.000 claims abstract 10
- AZFLJNIPTRTECV-FUMNGEBKSA-N dienogest Chemical compound C1CC(=O)C=C2CC[C@@H]([C@H]3[C@@](C)([C@](CC3)(O)CC#N)CC3)C3=C21 AZFLJNIPTRTECV-FUMNGEBKSA-N 0.000 claims abstract 7
- 229960003309 dienogest Drugs 0.000 claims abstract 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims abstract 6
- JQRYUMGHOUYJFW-UHFFFAOYSA-N pyridine;trihydrobromide Chemical compound [Br-].[Br-].[Br-].C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1 JQRYUMGHOUYJFW-UHFFFAOYSA-N 0.000 claims abstract 5
- XFFZLECPCHQJIR-BBCBXFPWSA-N (8r,9s,13s,14s)-3-methoxy-13-methyl-1,4,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-ol Chemical compound C1C[C@@H]2C(CC=C(C3)OC)=C3CC[C@H]2[C@@H]2CCC(O)[C@]21C XFFZLECPCHQJIR-BBCBXFPWSA-N 0.000 claims abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract 4
- 150000007524 organic acids Chemical class 0.000 claims abstract 3
- 238000002953 preparative HPLC Methods 0.000 claims abstract 3
- 238000000746 purification Methods 0.000 claims abstract 3
- 238000001953 recrystallisation Methods 0.000 claims abstract 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract 3
- NSUVCVKCWGOYPV-VXNCWWDNSA-N (8r,9s,13s,14s)-3-methoxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C1C[C@@H]2C(CC=C(C3)OC)=C3CC[C@H]2[C@@H]2CCC(=O)[C@]21C NSUVCVKCWGOYPV-VXNCWWDNSA-N 0.000 claims abstract 2
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000010438 heat treatment Methods 0.000 claims abstract 2
- 239000003960 organic solvent Substances 0.000 claims abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- OFIPMSSTKFSADG-UHFFFAOYSA-N [Li]CC#N Chemical compound [Li]CC#N OFIPMSSTKFSADG-UHFFFAOYSA-N 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 238000010306 acid treatment Methods 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 238000006215 cyanomethylation reaction Methods 0.000 claims 2
- 238000004128 high performance liquid chromatography Methods 0.000 claims 2
- 239000004135 Bone phosphate Substances 0.000 claims 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- 239000003463 adsorbent Substances 0.000 claims 1
- 239000003480 eluent Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 239000000741 silica gel Substances 0.000 claims 1
- 229910002027 silica gel Inorganic materials 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
-
- 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
-
- 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
- A61P15/18—Feminine contraceptives
-
- 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
- A61P5/34—Gestagens
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0501132A HUP0501132A2 (en) | 2005-12-05 | 2005-12-05 | 17-alpha-cyanomethyl-17betha-hydroxyestra-4,9-diene-3-one of high purity and process for its production |
| PCT/HU2006/000091 WO2007066158A2 (fr) | 2005-12-05 | 2006-10-11 | 17α-CYANOMETHYL-17β-HYDROXY-ESTRA-4,9-DIENE-3-ONE DE PURETE ELEVEE ET SON PROCEDE DE SYNTHESE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20100102T1 true HRP20100102T1 (hr) | 2010-04-30 |
Family
ID=89986433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20100102T HRP20100102T1 (hr) | 2005-12-05 | 2010-02-26 | 17alfa-CIJANOMETIL-17beta-HIDROKSI-ESTRA-4,9-DIEN-3-ON VISOKE ČISTOĆE I POSTUPAK NJEGOVE SINTEZE |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US8314145B2 (fr) |
| EP (1) | EP1963354B1 (fr) |
| JP (1) | JP5399711B2 (fr) |
| CN (1) | CN101360757B (fr) |
| AT (1) | ATE451383T1 (fr) |
| AU (1) | AU2006323005B2 (fr) |
| BR (1) | BRPI0619428B8 (fr) |
| CA (1) | CA2631748C (fr) |
| CY (1) | CY1110063T1 (fr) |
| DE (1) | DE602006011052D1 (fr) |
| DK (1) | DK1963354T3 (fr) |
| EA (1) | EA014558B1 (fr) |
| ES (1) | ES2338047T3 (fr) |
| HR (1) | HRP20100102T1 (fr) |
| HU (1) | HUP0501132A2 (fr) |
| IL (1) | IL191915A (fr) |
| MX (1) | MX2008007243A (fr) |
| PL (1) | PL1963354T3 (fr) |
| PT (1) | PT1963354E (fr) |
| SI (1) | SI1963354T1 (fr) |
| UA (1) | UA91390C2 (fr) |
| WO (1) | WO2007066158A2 (fr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE536362T1 (de) | 2009-05-22 | 2011-12-15 | Heyl Chem Pharm | Verfahren zur synthese von dienogest aus estron-3-methylether |
| EP2560984B1 (fr) | 2010-04-20 | 2015-04-01 | Lupin Limited | Procédé de préparation de dienogest sensiblement dépourvu d'impuretés |
| CN101863947A (zh) * | 2010-06-29 | 2010-10-20 | 沈阳药科大学 | 一种地诺孕素的合成方法 |
| CN103304619B (zh) * | 2013-06-08 | 2015-12-02 | 西藏海思科药业集团股份有限公司 | 一种地诺孕素化合物 |
| HU230788B1 (en) * | 2013-12-16 | 2018-05-02 | Richter Gedeon Nyrt | Norsteroid intermediates and process for their preparation |
| WO2017064814A1 (fr) * | 2015-10-16 | 2017-04-20 | 持田製薬株式会社 | Comprimé contenant du diénogest |
| JP6002870B1 (ja) * | 2015-10-16 | 2016-10-05 | 持田製薬株式会社 | 低用量薬物を含有する口腔内崩壊錠 |
| CN110357937A (zh) * | 2018-03-26 | 2019-10-22 | 华润紫竹药业有限公司 | 一种地诺孕素化合物 |
| CN110655551A (zh) * | 2019-09-23 | 2020-01-07 | 华润紫竹药业有限公司 | 一种地诺孕素药物单一新晶型及其制备方法 |
| CN114736261A (zh) * | 2022-05-17 | 2022-07-12 | 梯尔希（南京）药物研发有限公司 | 8,11-二烯地塞米松的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3391165A (en) * | 1966-04-07 | 1968-07-02 | Smith | Synthesis of gon-5(10)-enes |
| DE2718872A1 (de) * | 1976-06-14 | 1977-12-22 | Jenapharm Veb | Verfahren zur herstellung von neuen gona-4,9(10)-dienen |
| DD160418A1 (de) * | 1979-05-22 | 1983-07-27 | Kurt Ponsold | Verfahren zur herstellung von 17alpha-substituierten gona-4,9-dienen |
| US5438134A (en) * | 1990-07-09 | 1995-08-01 | Jenapharm Gmbh | Process for the production of unsaturated 17 α-cyanomethyl-17 β-h |
| IL119649A (en) | 1995-11-30 | 2002-03-10 | Akzo Nobel Nv | Preparation of Cyclic Kills of History - 3 keto- (5) 10, (-9) 11 steroidadians |
| IT1318491B1 (it) * | 2000-04-21 | 2003-08-25 | Ind Chimica Srl | Processo per la preparazione di un precursore di tibolone e diestradiol derivati strutturalmente correlati. |
| JP5230450B2 (ja) * | 2006-02-17 | 2013-07-10 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | プロゲステロン受容体モジュレーターとして有用な１７−燐ステロイド誘導体 |
-
2005
- 2005-12-05 HU HU0501132A patent/HUP0501132A2/hu unknown
-
2006
- 2006-10-11 US US12/096,209 patent/US8314145B2/en active Active
- 2006-10-11 MX MX2008007243A patent/MX2008007243A/es active IP Right Grant
- 2006-10-11 AU AU2006323005A patent/AU2006323005B2/en active Active
- 2006-10-11 CN CN2006800515980A patent/CN101360757B/zh active Active
- 2006-10-11 ES ES06808800T patent/ES2338047T3/es active Active
- 2006-10-11 PL PL06808800T patent/PL1963354T3/pl unknown
- 2006-10-11 DK DK06808800.4T patent/DK1963354T3/da active
- 2006-10-11 UA UAA200808851A patent/UA91390C2/ru unknown
- 2006-10-11 JP JP2008543921A patent/JP5399711B2/ja active Active
- 2006-10-11 EP EP06808800A patent/EP1963354B1/fr active Active
- 2006-10-11 AT AT06808800T patent/ATE451383T1/de active
- 2006-10-11 BR BRPI0619428A patent/BRPI0619428B8/pt active IP Right Grant
- 2006-10-11 WO PCT/HU2006/000091 patent/WO2007066158A2/fr active Application Filing
- 2006-10-11 CA CA2631748A patent/CA2631748C/fr active Active
- 2006-10-11 SI SI200630561T patent/SI1963354T1/sl unknown
- 2006-10-11 DE DE602006011052T patent/DE602006011052D1/de active Active
- 2006-10-11 EA EA200801508A patent/EA014558B1/ru unknown
- 2006-10-11 PT PT06808800T patent/PT1963354E/pt unknown
-
2008
- 2008-06-03 IL IL191915A patent/IL191915A/en active IP Right Grant
-
2010
- 2010-01-29 CY CY20101100088T patent/CY1110063T1/el unknown
- 2010-02-26 HR HR20100102T patent/HRP20100102T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2006323005A1 (en) | 2007-06-14 |
| JP5399711B2 (ja) | 2014-01-29 |
| ATE451383T1 (de) | 2009-12-15 |
| SI1963354T1 (sl) | 2010-03-31 |
| BRPI0619428A2 (pt) | 2011-10-04 |
| IL191915A0 (en) | 2008-12-29 |
| MX2008007243A (es) | 2008-10-22 |
| BRPI0619428B8 (pt) | 2021-05-25 |
| WO2007066158A2 (fr) | 2007-06-14 |
| BRPI0619428B1 (pt) | 2021-02-17 |
| PL1963354T3 (pl) | 2010-05-31 |
| IL191915A (en) | 2016-04-21 |
| HUP0501132A2 (en) | 2007-06-28 |
| DE602006011052D1 (de) | 2010-01-21 |
| CA2631748C (fr) | 2013-12-03 |
| CN101360757B (zh) | 2011-07-20 |
| CN101360757A (zh) | 2009-02-04 |
| PT1963354E (pt) | 2010-01-06 |
| CA2631748A1 (fr) | 2007-06-14 |
| CY1110063T1 (el) | 2015-01-14 |
| JP2009518377A (ja) | 2009-05-07 |
| HU0501132D0 (en) | 2006-01-30 |
| AU2006323005B2 (en) | 2013-05-30 |
| EP1963354B1 (fr) | 2009-12-09 |
| EP1963354A2 (fr) | 2008-09-03 |
| UA91390C2 (en) | 2010-07-26 |
| US20080287404A1 (en) | 2008-11-20 |
| EA014558B1 (ru) | 2010-12-30 |
| EA200801508A1 (ru) | 2008-10-30 |
| US8314145B2 (en) | 2012-11-20 |
| WO2007066158A3 (fr) | 2007-08-09 |
| DK1963354T3 (da) | 2010-04-12 |
| ES2338047T3 (es) | 2010-05-03 |
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