HUP0004967A2 - New crystalline form of nestorone and process for the preparation thereof - Google Patents
New crystalline form of nestorone and process for the preparation thereof Download PDFInfo
- Publication number
- HUP0004967A2 HUP0004967A2 HU0004967A HUP0004967A HUP0004967A2 HU P0004967 A2 HUP0004967 A2 HU P0004967A2 HU 0004967 A HU0004967 A HU 0004967A HU P0004967 A HUP0004967 A HU P0004967A HU P0004967 A2 HUP0004967 A2 HU P0004967A2
- Authority
- HU
- Hungary
- Prior art keywords
- water
- nestorone
- modification
- organic solvent
- nesztoron
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 229950007611 elcometrine Drugs 0.000 title claims description 33
- CKFBRGLGTWAVLG-GOMYTPFNSA-N elcometrine Chemical compound C1CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC(=C)[C@](OC(=O)C)(C(C)=O)[C@@]1(C)CC2 CKFBRGLGTWAVLG-GOMYTPFNSA-N 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 15
- 239000013078 crystal Substances 0.000 claims abstract description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 4
- 239000007787 solid Substances 0.000 claims abstract description 3
- 230000004048 modification Effects 0.000 claims description 62
- 238000012986 modification Methods 0.000 claims description 62
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 11
- 239000000725 suspension Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 7
- 238000002329 infrared spectrum Methods 0.000 claims description 7
- 230000008018 melting Effects 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 238000001237 Raman spectrum Methods 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- -1 aliphatic nitrile Chemical class 0.000 claims description 2
- 238000001938 differential scanning calorimetry curve Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 230000000877 morphologic effect Effects 0.000 claims 2
- 238000010521 absorption reaction Methods 0.000 claims 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 239000006071 cream Substances 0.000 abstract description 3
- 238000002425 crystallisation Methods 0.000 abstract description 3
- 239000000499 gel Substances 0.000 abstract description 3
- 238000009826 distribution Methods 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract description 2
- 238000009472 formulation Methods 0.000 abstract 1
- SFLXYFZGKSGFKA-XUDSTZEESA-N (8r,9s,10r,13s,14s,17r)-17-acetyl-17-hydroxy-13-methyl-16-methylidene-2,6,7,8,9,10,11,12,14,15-decahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC(=C)[C@@](C(=O)C)(O)[C@@]1(C)CC2 SFLXYFZGKSGFKA-XUDSTZEESA-N 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N Methyl ethyl ketone Natural products CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000002178 crystalline material Substances 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- 230000035558 fertility Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000001931 thermography Methods 0.000 description 2
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 1
- 238000004438 BET method Methods 0.000 description 1
- 238000005079 FT-Raman Methods 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003433 contraceptive agent Substances 0.000 description 1
- 230000002254 contraceptive effect Effects 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000757 progestagenic effect Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Landscapes
- Medicinal Preparation (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0004967A HUP0004967A2 (en) | 2000-12-18 | 2000-12-18 | New crystalline form of nestorone and process for the preparation thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0004967A HUP0004967A2 (en) | 2000-12-18 | 2000-12-18 | New crystalline form of nestorone and process for the preparation thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HU0004967D0 HU0004967D0 (enrdf_load_stackoverflow) | 2001-02-28 |
| HUP0004967A2 true HUP0004967A2 (en) | 2002-09-28 |
Family
ID=89978862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0004967A HUP0004967A2 (en) | 2000-12-18 | 2000-12-18 | New crystalline form of nestorone and process for the preparation thereof |
Country Status (1)
| Country | Link |
|---|---|
| HU (1) | HUP0004967A2 (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10632066B1 (en) | 2019-02-01 | 2020-04-28 | The Population Council, Inc. | Method of providing birth control |
| WO2020257544A1 (en) | 2019-06-21 | 2020-12-24 | The Population Council, Inc. | System for providing birth control |
| WO2022236045A1 (en) | 2021-05-07 | 2022-11-10 | The Population Council, Inc. | Methods of providing birth control |
| US11529308B2 (en) | 2019-06-21 | 2022-12-20 | The Population Council, Inc. | System for providing birth control |
-
2000
- 2000-12-18 HU HU0004967A patent/HUP0004967A2/hu unknown
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10632066B1 (en) | 2019-02-01 | 2020-04-28 | The Population Council, Inc. | Method of providing birth control |
| US10765628B2 (en) | 2019-02-01 | 2020-09-08 | The Population Council, Inc. | Method of providing birth control |
| US10780047B2 (en) | 2019-02-01 | 2020-09-22 | The Population Council, Inc. | Method of providing birth control |
| WO2020257544A1 (en) | 2019-06-21 | 2020-12-24 | The Population Council, Inc. | System for providing birth control |
| US10918649B2 (en) | 2019-06-21 | 2021-02-16 | The Population Council, Inc. | System for providing birth control |
| US10925882B2 (en) | 2019-06-21 | 2021-02-23 | The Population Council, Inc. | System for providing birth control |
| US10940157B2 (en) | 2019-06-21 | 2021-03-09 | The Population Council, Inc. | System for providing birth control |
| US11529308B2 (en) | 2019-06-21 | 2022-12-20 | The Population Council, Inc. | System for providing birth control |
| US12303518B2 (en) | 2019-06-21 | 2025-05-20 | The Population Council, Inc. | System for providing birth control |
| WO2022236045A1 (en) | 2021-05-07 | 2022-11-10 | The Population Council, Inc. | Methods of providing birth control |
Also Published As
| Publication number | Publication date |
|---|---|
| HU0004967D0 (enrdf_load_stackoverflow) | 2001-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HC9A | Change of name, address |
Owner name: RICHTER GEDEON NYRT., HU Free format text: FORMER OWNER(S): RICHTER GEDEON VEGYESZETI GYAR RT., HU |
|
| FA9A | Lapse of provisional patent protection due to relinquishment or protection considered relinquished |