JP2005532336A - 新規なエトノゲストレルエステルの使用 - Google Patents
新規なエトノゲストレルエステルの使用 Download PDFInfo
- Publication number
- JP2005532336A JP2005532336A JP2004508732A JP2004508732A JP2005532336A JP 2005532336 A JP2005532336 A JP 2005532336A JP 2004508732 A JP2004508732 A JP 2004508732A JP 2004508732 A JP2004508732 A JP 2004508732A JP 2005532336 A JP2005532336 A JP 2005532336A
- Authority
- JP
- Japan
- Prior art keywords
- etonogestrel
- contraceptive
- ester
- effective amount
- undecanoate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- GCKFUYQCUCGESZ-BPIQYHPVSA-N etonogestrel Chemical class O=C1CC[C@@H]2[C@H]3C(=C)C[C@](CC)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 GCKFUYQCUCGESZ-BPIQYHPVSA-N 0.000 title claims description 83
- 229960002941 etonogestrel Drugs 0.000 claims abstract description 113
- -1 etonogestrel ester Chemical class 0.000 claims abstract description 51
- 239000003433 contraceptive agent Substances 0.000 claims abstract description 48
- 230000002254 contraceptive effect Effects 0.000 claims abstract description 48
- 238000011282 treatment Methods 0.000 claims abstract description 20
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 claims description 65
- YSGQGNQWBLYHPE-CFUSNLFHSA-N (7r,8r,9s,10r,13s,14s,17s)-17-hydroxy-7,13-dimethyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-one Chemical group C1C[C@]2(C)[C@@H](O)CC[C@H]2[C@@H]2[C@H](C)CC3=CC(=O)CC[C@@H]3[C@H]21 YSGQGNQWBLYHPE-CFUSNLFHSA-N 0.000 claims description 50
- 150000002148 esters Chemical class 0.000 claims description 26
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 12
- 229940011871 estrogen Drugs 0.000 claims description 10
- 239000000262 estrogen Substances 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 239000003098 androgen Substances 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
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- 230000002265 prevention Effects 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 5
- 208000005171 Dysmenorrhea Diseases 0.000 claims description 4
- 206010013935 Dysmenorrhoea Diseases 0.000 claims description 4
- 201000009273 Endometriosis Diseases 0.000 claims description 4
- 206010036618 Premenstrual syndrome Diseases 0.000 claims description 4
- 206010046788 Uterine haemorrhage Diseases 0.000 claims description 4
- 208000007106 menorrhagia Diseases 0.000 claims description 4
- 239000002583 male contraceptive agent Substances 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims 1
- 238000002483 medication Methods 0.000 claims 1
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 34
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 24
- 229960003604 testosterone Drugs 0.000 description 17
- 241000283973 Oryctolagus cuniculus Species 0.000 description 15
- 238000002657 hormone replacement therapy Methods 0.000 description 15
- 235000019483 Peanut oil Nutrition 0.000 description 14
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- 239000000243 solution Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 229960002903 benzyl benzoate Drugs 0.000 description 12
- BWEZMBMJQRHPSZ-UHFFFAOYSA-N ethyl undecanoate Chemical compound CCCCCCCCCCC(=O)OCC.CCCCCCCCCCC(=O)OCC BWEZMBMJQRHPSZ-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 239000000583 progesterone congener Substances 0.000 description 11
- VOCBWIIFXDYGNZ-IXKNJLPQSA-N testosterone enanthate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CCCCCC)[C@@]1(C)CC2 VOCBWIIFXDYGNZ-IXKNJLPQSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229960003484 testosterone enanthate Drugs 0.000 description 9
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 8
- 229960000746 testosterone undecanoate Drugs 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 150000003509 tertiary alcohols Chemical class 0.000 description 6
- UDSFVOAUHKGBEK-CNQKSJKFSA-N testosterone undecanoate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CCCCCCCCCC)[C@@]1(C)CC2 UDSFVOAUHKGBEK-CNQKSJKFSA-N 0.000 description 6
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
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- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
- 230000007774 longterm Effects 0.000 description 4
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- 150000003431 steroids Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- 238000003556 assay Methods 0.000 description 3
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 3
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- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 2
- 102000012673 Follicle Stimulating Hormone Human genes 0.000 description 2
- 108010079345 Follicle Stimulating Hormone Proteins 0.000 description 2
- 102000009151 Luteinizing Hormone Human genes 0.000 description 2
- 108010073521 Luteinizing Hormone Proteins 0.000 description 2
- 206010030247 Oestrogen deficiency Diseases 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WAHQVRCNDCHDIB-QZYSPNBYSA-N [(3s,8r,9s,10r,13s,14s,17r)-17-acetyl-17-acetyloxy-6,10,13-trimethyl-1,2,3,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-yl] 3-cyclopentylpropanoate Chemical compound O([C@@H]1C=C2C(C)=C[C@H]3[C@@H]4CC[C@]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)(OC(=O)C)C(C)=O)C(=O)CCC1CCCC1 WAHQVRCNDCHDIB-QZYSPNBYSA-N 0.000 description 2
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- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- RPLCPCMSCLEKRS-BPIQYHPVSA-N desogestrel Chemical compound C1CC[C@@H]2[C@H]3C(=C)C[C@](CC)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 RPLCPCMSCLEKRS-BPIQYHPVSA-N 0.000 description 2
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- 229960005309 estradiol Drugs 0.000 description 2
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- PROQIPRRNZUXQM-ZXXIGWHRSA-N estriol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H]([C@H](O)C4)O)[C@@H]4[C@@H]3CCC2=C1 PROQIPRRNZUXQM-ZXXIGWHRSA-N 0.000 description 2
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 2
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
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- BFPYWIDHMRZLRN-UHFFFAOYSA-N 17alpha-ethynyl estradiol Natural products OC1=CC=C2C3CCC(C)(C(CC4)(O)C#C)C4C3CCC2=C1 BFPYWIDHMRZLRN-UHFFFAOYSA-N 0.000 description 1
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- QGLVWTFUWVTDEQ-UHFFFAOYSA-N 2-chloro-3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1Cl QGLVWTFUWVTDEQ-UHFFFAOYSA-N 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000006213 vaginal ring Substances 0.000 description 1
Images
Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
- A61K31/569—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone substituted in position 17 alpha, e.g. ethisterone
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
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- A—HUMAN NECESSITIES
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- A61P15/18—Feminine contraceptives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
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- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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- 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
- A61P5/18—Drugs for disorders of the endocrine system of the parathyroid hormones
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- 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
- A61P5/26—Androgens
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Reproductive Health (AREA)
- Gynecology & Obstetrics (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Pregnancy & Childbirth (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02077118 | 2002-05-30 | ||
| PCT/EP2003/050188 WO2003101374A2 (en) | 2002-05-30 | 2003-05-22 | Use of new etonogestrel esters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005532336A true JP2005532336A (ja) | 2005-10-27 |
| JP2005532336A5 JP2005532336A5 (enExample) | 2006-07-06 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004508732A Withdrawn JP2005532336A (ja) | 2002-05-30 | 2003-05-22 | 新規なエトノゲストレルエステルの使用 |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US20050222114A1 (enExample) |
| EP (1) | EP1513588B1 (enExample) |
| JP (1) | JP2005532336A (enExample) |
| KR (1) | KR20050005507A (enExample) |
| CN (1) | CN1655848A (enExample) |
| AR (1) | AR040129A1 (enExample) |
| AT (1) | ATE394140T1 (enExample) |
| AU (1) | AU2003246740B2 (enExample) |
| BR (1) | BR0311248A (enExample) |
| CA (1) | CA2487293A1 (enExample) |
| DE (1) | DE60320786D1 (enExample) |
| ES (1) | ES2305498T3 (enExample) |
| HR (1) | HRP20041127A2 (enExample) |
| IL (1) | IL165125A0 (enExample) |
| IS (1) | IS7537A (enExample) |
| MX (1) | MXPA04011798A (enExample) |
| NO (1) | NO20044903L (enExample) |
| NZ (1) | NZ536618A (enExample) |
| PE (1) | PE20040042A1 (enExample) |
| PL (1) | PL373295A1 (enExample) |
| RS (1) | RS101004A (enExample) |
| RU (1) | RU2322986C2 (enExample) |
| TW (1) | TW200400041A (enExample) |
| UA (1) | UA80703C2 (enExample) |
| WO (1) | WO2003101374A2 (enExample) |
| ZA (1) | ZA200409498B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200403065A (en) * | 2002-05-30 | 2004-03-01 | Akzo Nobel Nv | New etonogestrel esters |
| US20130123523A1 (en) * | 2011-11-10 | 2013-05-16 | Klaus Nickisch | Methods for the preparation of etonogestrel and desogestrel |
| DE102012211511A1 (de) * | 2012-07-03 | 2014-01-09 | Siemens Aktiengesellschaft | Bestimmung der Eignung einer Ressource |
| BR112020007673A2 (pt) * | 2017-10-19 | 2020-10-13 | Evestra, Inc. | contraceptivos pró-fármaco de progestina de ação prolongada |
| CN111057120B (zh) * | 2019-12-27 | 2021-04-27 | 苏州翔实医药发展有限公司 | 一种依托孕烯衍生物a及其制备方法和用途 |
| EP4164743A2 (en) * | 2020-06-11 | 2023-04-19 | The United States of America, as represented by The Secretary, Department of Health and Human Services | Monomeric and oligomeric compound embodiments as contraceptives and therapies and methods of making and using the same |
Family Cites Families (9)
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| DE4227989A1 (de) * | 1992-08-21 | 1994-06-09 | Schering Ag | Mittel zur transdermalen Applikation enthaltend 3-Keto-desogestrel |
| DE4240806A1 (de) * | 1992-12-01 | 1994-06-09 | Schering Ag | Mittel zur transdermalen Applikation enthaltend 14alpha,17alpha-Ethanoestra-1,3,5(10)-trien-3,17beta-diol |
| JPH07101884A (ja) * | 1993-10-01 | 1995-04-18 | Sanei Gen F F I Inc | 水溶性ヘミセルロースを含有する製剤 |
| CN1135716A (zh) * | 1993-12-27 | 1996-11-13 | 阿克佐诺贝尔公司 | 经皮吸收的药用制剂 |
| WO1997003709A1 (de) * | 1995-07-17 | 1997-02-06 | Schering Aktiengesellschaft | Mittel zur transdermalen applikation enthaltend ester des 3-ketodegestrel |
| TR200003743T2 (tr) * | 1998-06-19 | 2001-07-23 | Akzo Nobel N.V. | Testosteron türevi. |
| WO1999067270A1 (en) * | 1998-06-19 | 1999-12-29 | Akzo Nobel N.V. | Cycloalkyl-carboxylic acid esters of 7.alpha.methyl-estr-4-en-3-one 17.beta.-ol (19-nor 7.alpha.-methyltestosterone) |
| US6180682B1 (en) * | 1999-01-26 | 2001-01-30 | Virgil A. Place | Buccal drug delivery system for use in male contraception |
| TW200403065A (en) * | 2002-05-30 | 2004-03-01 | Akzo Nobel Nv | New etonogestrel esters |
-
2003
- 2003-05-19 TW TW092113492A patent/TW200400041A/zh unknown
- 2003-05-22 WO PCT/EP2003/050188 patent/WO2003101374A2/en not_active Ceased
- 2003-05-22 EP EP03755980A patent/EP1513588B1/en not_active Expired - Lifetime
- 2003-05-22 RU RU2004138809/15A patent/RU2322986C2/ru active
- 2003-05-22 JP JP2004508732A patent/JP2005532336A/ja not_active Withdrawn
- 2003-05-22 CN CNA038123657A patent/CN1655848A/zh active Pending
- 2003-05-22 KR KR10-2004-7019327A patent/KR20050005507A/ko not_active Withdrawn
- 2003-05-22 HR HR20041127A patent/HRP20041127A2/hr not_active Application Discontinuation
- 2003-05-22 PL PL03373295A patent/PL373295A1/xx not_active Application Discontinuation
- 2003-05-22 RS YU101004A patent/RS101004A/sr unknown
- 2003-05-22 ES ES03755980T patent/ES2305498T3/es not_active Expired - Lifetime
- 2003-05-22 UA UA20041109285A patent/UA80703C2/uk unknown
- 2003-05-22 US US10/517,362 patent/US20050222114A1/en not_active Abandoned
- 2003-05-22 MX MXPA04011798A patent/MXPA04011798A/es unknown
- 2003-05-22 DE DE60320786T patent/DE60320786D1/de not_active Expired - Fee Related
- 2003-05-22 CA CA002487293A patent/CA2487293A1/en not_active Abandoned
- 2003-05-22 AT AT03755980T patent/ATE394140T1/de not_active IP Right Cessation
- 2003-05-22 BR BR0311248-9A patent/BR0311248A/pt not_active IP Right Cessation
- 2003-05-22 AU AU2003246740A patent/AU2003246740B2/en not_active Ceased
- 2003-05-22 NZ NZ536618A patent/NZ536618A/en unknown
- 2003-05-26 PE PE2003000508A patent/PE20040042A1/es not_active Application Discontinuation
- 2003-05-28 AR ARP030101858A patent/AR040129A1/es unknown
-
2004
- 2004-11-09 IL IL16512504A patent/IL165125A0/xx unknown
- 2004-11-10 NO NO20044903A patent/NO20044903L/no not_active Application Discontinuation
- 2004-11-18 IS IS7537A patent/IS7537A/is unknown
- 2004-11-24 ZA ZA200409498A patent/ZA200409498B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ536618A (en) | 2007-06-29 |
| RU2322986C2 (ru) | 2008-04-27 |
| EP1513588A2 (en) | 2005-03-16 |
| AR040129A1 (es) | 2005-03-16 |
| RU2004138809A (ru) | 2005-06-10 |
| US20050222114A1 (en) | 2005-10-06 |
| IL165125A0 (en) | 2005-12-18 |
| PE20040042A1 (es) | 2004-01-31 |
| DE60320786D1 (de) | 2008-06-19 |
| BR0311248A (pt) | 2005-03-15 |
| UA80703C2 (en) | 2007-10-25 |
| HK1072568A1 (en) | 2005-09-02 |
| TW200400041A (en) | 2004-01-01 |
| WO2003101374A2 (en) | 2003-12-11 |
| CN1655848A (zh) | 2005-08-17 |
| CA2487293A1 (en) | 2003-12-11 |
| PL373295A1 (en) | 2005-08-22 |
| WO2003101374A3 (en) | 2004-02-26 |
| AU2003246740B2 (en) | 2009-01-08 |
| MXPA04011798A (es) | 2005-03-31 |
| AU2003246740A1 (en) | 2003-12-19 |
| IS7537A (is) | 2004-11-18 |
| RS101004A (sr) | 2006-10-27 |
| ES2305498T3 (es) | 2008-11-01 |
| NO20044903L (no) | 2005-02-25 |
| HRP20041127A2 (en) | 2005-02-28 |
| EP1513588B1 (en) | 2008-05-07 |
| KR20050005507A (ko) | 2005-01-13 |
| ZA200409498B (en) | 2006-05-31 |
| ATE394140T1 (de) | 2008-05-15 |
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