SK286757B6 - 17-Metylénsteroidy, spôsob ich prípravy, farmaceutické kompozície, ktoré ich obsahujú, a ich použitie - Google Patents

17-Metylénsteroidy, spôsob ich prípravy, farmaceutické kompozície, ktoré ich obsahujú, a ich použitie Download PDF

Info

Publication number: SK286757B6
Authority: SK; Slovakia
Prior art keywords: chloro; estr; pseudohalogen; formula; hydrogen atom
Prior art date: 2000-09-04

Application number

SK244-2003A

Other languages

English (en)

Slovak (sk)

Other versions

SK2442003A3 (en

Inventor

Bernd Menzenbach

Walter Elger

Peter Droescher

Alexander Hillisch

G�nter KAUFMANN

Hans-Udo Schweikert

Gerd Mller

Original Assignee

Schering Ag

Priority date (The priority date 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 date listed.)

2000-09-04

Filing date

2001-08-29

Publication date

2009-05-07

2001-08-29 Application filed by Schering Ag filed Critical Schering Ag

2003-08-05 Publication of SK2442003A3 publication Critical patent/SK2442003A3/sk

2009-05-07 Publication of SK286757B6 publication Critical patent/SK286757B6/sk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 51
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 7
238000000034 method Methods 0.000 title claims abstract description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
125000002577 pseudohalo group Chemical group 0.000 claims abstract description 18
125000005843 halogen group Chemical group 0.000 claims abstract description 13
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 7
108010066551 Cholestenone 5 alpha-Reductase Proteins 0.000 claims abstract description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 13
239000000010 aprotic solvent Substances 0.000 claims description 13
238000002360 preparation method Methods 0.000 claims description 10
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
230000005764 inhibitory process Effects 0.000 claims description 8
CYDMYWHMDASKOT-QRXQDIEBSA-N (8r,9s,10r,13s,14s,17e)-4-chloro-17-(chloromethylidene)-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)(C(/CC4)=C/Cl)[C@@H]4[C@@H]3CCC2=C1Cl CYDMYWHMDASKOT-QRXQDIEBSA-N 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
239000004480 active ingredient Substances 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
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JCBFSZAXCWTSSI-QRXQDIEBSA-N (8r,9s,10r,13s,14s,17e)-17-(bromomethylidene)-4-chloro-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)(C(/CC4)=C/Br)[C@@H]4[C@@H]3CCC2=C1Cl JCBFSZAXCWTSSI-QRXQDIEBSA-N 0.000 claims description 4
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
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KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
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-1 fluoro-21-hydroxypregna-4,17 (20) -diene-3-one Chemical compound 0.000 claims description 3
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GWDCVGJWTTYHRW-BUNPSNNLSA-N (8r,9s,10r,13s,14s,17e)-17-(chloromethylidene)-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthrene-4-carbonitrile Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(/CC4)=C/Cl)[C@@H]4[C@@H]3CCC2=C1C#N GWDCVGJWTTYHRW-BUNPSNNLSA-N 0.000 claims description 2
NVISWEPHXBNEQS-PSYRKBHYSA-N (8s,9s,10r,13s,14s)-4-chloro-10,13-dimethyl-17-methylidene-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=C)[C@@H]4[C@@H]3CCC2=C1Cl NVISWEPHXBNEQS-PSYRKBHYSA-N 0.000 claims description 2
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239000003937 drug carrier Substances 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
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BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 2
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SHMKHOZQOMRFRD-CMQYSOMSSA-N (8r,9s,10r,13s,14s,17z)-4-chloro-17-(2-chloroethylidene)-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)(C(/CC4)=C\CCl)[C@@H]4[C@@H]3CCC2=C1Cl SHMKHOZQOMRFRD-CMQYSOMSSA-N 0.000 claims 1
MPOZXKYQQJUQEO-FUJXVJAHSA-N (8r,9s,10r,13s,14s,17z)-4-chloro-17-ethylidene-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=C(Cl)C(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC/C(=C/C)[C@@]1(C)CC2 MPOZXKYQQJUQEO-FUJXVJAHSA-N 0.000 claims 1
JCBFSZAXCWTSSI-DYPAMSTGSA-N C[C@]1\2CC[C@H]3[C@H]([C@@H]1CC/C2=C/Br)CCC4=C(C(=O)CC[C@H]34)Cl Chemical compound C[C@]1\2CC[C@H]3[C@H]([C@@H]1CC/C2=C/Br)CCC4=C(C(=O)CC[C@H]34)Cl JCBFSZAXCWTSSI-DYPAMSTGSA-N 0.000 claims 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
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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 abstract description 10
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239000013543 active substance Substances 0.000 description 1
HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 1
229940043377 alpha-cyclodextrin Drugs 0.000 description 1
230000002280 anti-androgenic effect Effects 0.000 description 1
239000000051 antiandrogen Substances 0.000 description 1
230000002238 attenuated effect Effects 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 1
229960004853 betadex Drugs 0.000 description 1
229920002988 biodegradable polymer Polymers 0.000 description 1
239000004621 biodegradable polymer Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
229940035811 conjugated estrogen Drugs 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
210000000172 cytosol Anatomy 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
229930182833 estradiol Natural products 0.000 description 1
229960001359 estradiol 3-benzoate Drugs 0.000 description 1
150000002159 estradiols Chemical class 0.000 description 1
229960003399 estrone Drugs 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000005038 ethylene vinyl acetate Substances 0.000 description 1
230000035558 fertility Effects 0.000 description 1
230000008175 fetal development Effects 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 description 1
229940080345 gamma-cyclodextrin Drugs 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
238000011534 incubation Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
239000002502 liposome Substances 0.000 description 1
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000002583 male contraceptive agent Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
229940110234 mirena Drugs 0.000 description 1
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
230000035935 pregnancy Effects 0.000 description 1
238000009597 pregnancy test Methods 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
229960003387 progesterone Drugs 0.000 description 1
239000000186 progesterone Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229920005573 silicon-containing polymer Polymers 0.000 description 1
229920002379 silicone rubber Polymers 0.000 description 1
239000004945 silicone rubber Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
230000021595 spermatogenesis Effects 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
239000006213 vaginal ring Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
- C07J13/007—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 17 (20)
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
- 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
- A61P15/16—Masculine 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- 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
- 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
- A61P5/28—Antiandrogens
- 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

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Endocrinology (AREA)
Diabetes (AREA)
Dermatology (AREA)
Reproductive Health (AREA)
Urology & Nephrology (AREA)
Gynecology & Obstetrics (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SK244-2003A 2000-09-04 2001-08-29 17-Metylénsteroidy, spôsob ich prípravy, farmaceutické kompozície, ktoré ich obsahujú, a ich použitie SK286757B6 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10043846A DE10043846A1 (de)	2000-09-04	2000-09-04	17-Methylensteroide, Verfahren zu deren Herstellung und diese Verbindung enthaltende pharmazeutische Zusammensetzungen
PCT/EP2001/009943 WO2002019971A1 (fr)	2000-09-04	2001-08-29	Steroides de 17-methylene, procede permettant de les produire et compositions pharmaceutiques contenant ces composes

Publications (2)

Publication Number	Publication Date
SK2442003A3 SK2442003A3 (en)	2003-08-05
SK286757B6 true SK286757B6 (sk)	2009-05-07

Family

ID=7655148

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK244-2003A SK286757B6 (sk)	2000-09-04	2001-08-29	17-Metylénsteroidy, spôsob ich prípravy, farmaceutické kompozície, ktoré ich obsahujú, a ich použitie

Country Status (28)

Country	Link
EP (1)	EP1423407B1 (fr)
JP (1)	JP2004513084A (fr)
KR (1)	KR100530816B1 (fr)
CN (1)	CN1262560C (fr)
AT (1)	ATE319733T1 (fr)
AU (2)	AU1047002A (fr)
BG (1)	BG107594A (fr)
BR (1)	BR0113618A (fr)
CA (1)	CA2421302C (fr)
DE (2)	DE10043846A1 (fr)
DK (1)	DK1423407T3 (fr)
EA (1)	EA006387B1 (fr)
EE (1)	EE05186B1 (fr)
ES (1)	ES2260294T3 (fr)
HR (1)	HRP20030256A2 (fr)
HU (1)	HUP0300936A3 (fr)
IL (2)	IL154666A0 (fr)
ME (1)	MEP14408A (fr)
MX (1)	MXPA03001912A (fr)
NO (1)	NO325012B1 (fr)
NZ (1)	NZ524485A (fr)
PL (1)	PL360669A1 (fr)
PT (1)	PT1423407E (fr)
RS (1)	RS50305B (fr)
SK (1)	SK286757B6 (fr)
UA (1)	UA74592C2 (fr)
WO (1)	WO2002019971A1 (fr)
ZA (1)	ZA200301715B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10141984A1 (de) *	2001-08-28	2003-03-20	Jenapharm Gmbh	Neue 17-Methylen-4-azasteroide
US7199115B2 (en)	2004-04-19	2007-04-03	Schering Ag	17α-fluorosteroids, pharmaceutical compositions containing 17α-fluorosteroids and a method of making them
DE202007019049U1 (de) *	2007-11-05	2010-05-12	Bayer Schering Pharma Aktiengesellschaft	Verwendung eines Gestagens in Kombination mit einem Estrogen zur Prophylaxe der Laktoseintoleranz bei der oralen Kontrazeption

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2611773A (en) *	1951-08-21	1952-09-23	Upjohn Co	Estradiol 17-cyclopenetanepropionate
US3146239A (en) *	1957-09-23	1964-08-25	Syntex Corp	4-halo-19-nor-progesterone
US3232960A (en) *	1959-10-08	1966-02-01	Upjohn Co	3-keto-4-fluoro- and 3-keto-4,4-difluorosteroids and process
US3661940A (en) *	1970-04-13	1972-05-09	Sandoz Ag	Derivatives of 21-methyl-19-norpregnanes
US4389345A (en) *	1981-10-09	1983-06-21	G.D. Searle & Co.	3-Oxoestra-17-acetonitrile and unsaturated analogs
US5994334A (en) *	1997-02-05	1999-11-30	University Of Maryland	Androgen synthesis inhibitors
AU2001268661A1 (en) *	2000-06-27	2002-01-08	Aventis Pharma S.A.	20-fluoro-17(20)-vinyl steroids as inhibitors of c17-20-lyase and 5-alpha reductase

2000
- 2000-09-04 DE DE10043846A patent/DE10043846A1/de not_active Ceased
2001
- 2001-08-29 NZ NZ524485A patent/NZ524485A/en unknown
- 2001-08-29 RS YUP-164/03A patent/RS50305B/sr unknown
- 2001-08-29 EA EA200300322A patent/EA006387B1/ru not_active IP Right Cessation
- 2001-08-29 EE EEP200300087A patent/EE05186B1/xx not_active IP Right Cessation
- 2001-08-29 PT PT01978315T patent/PT1423407E/pt unknown
- 2001-08-29 IL IL15466601A patent/IL154666A0/xx unknown
- 2001-08-29 KR KR10-2003-7003170A patent/KR100530816B1/ko not_active Expired - Fee Related
- 2001-08-29 AT AT01978315T patent/ATE319733T1/de not_active IP Right Cessation
- 2001-08-29 ME MEP-144/08A patent/MEP14408A/xx unknown
- 2001-08-29 DE DE50109175T patent/DE50109175D1/de not_active Expired - Lifetime
- 2001-08-29 HU HU0300936A patent/HUP0300936A3/hu unknown
- 2001-08-29 HR HR20030256A patent/HRP20030256A2/hr not_active Application Discontinuation
- 2001-08-29 BR BR0113618-6A patent/BR0113618A/pt not_active IP Right Cessation
- 2001-08-29 CN CNB018151345A patent/CN1262560C/zh not_active Expired - Fee Related
- 2001-08-29 AU AU1047002A patent/AU1047002A/xx active Pending
- 2001-08-29 UA UA2003042852A patent/UA74592C2/uk unknown
- 2001-08-29 EP EP01978315A patent/EP1423407B1/fr not_active Expired - Lifetime
- 2001-08-29 WO PCT/EP2001/009943 patent/WO2002019971A1/fr not_active Ceased
- 2001-08-29 PL PL36066901A patent/PL360669A1/xx unknown
- 2001-08-29 AU AU2002210470A patent/AU2002210470B2/en not_active Ceased
- 2001-08-29 SK SK244-2003A patent/SK286757B6/sk not_active IP Right Cessation
- 2001-08-29 DK DK01978315T patent/DK1423407T3/da active
- 2001-08-29 JP JP2002524456A patent/JP2004513084A/ja active Pending
- 2001-08-29 MX MXPA03001912A patent/MXPA03001912A/es active IP Right Grant
- 2001-08-29 ES ES01978315T patent/ES2260294T3/es not_active Expired - Lifetime
- 2001-08-29 CA CA002421302A patent/CA2421302C/fr not_active Expired - Fee Related
2003
- 2003-02-27 BG BG107594A patent/BG107594A/bg unknown
- 2003-02-27 IL IL154666A patent/IL154666A/en not_active IP Right Cessation
- 2003-02-28 ZA ZA200301715A patent/ZA200301715B/en unknown
- 2003-03-03 NO NO20030989A patent/NO325012B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
MXPA03001912A (es)	2004-07-08
DE50109175D1 (de)	2006-05-04
EA200300322A1 (ru)	2003-10-30
DE10043846A1 (de)	2002-04-04
CN1262560C (zh)	2006-07-05
CA2421302C (fr)	2007-08-14
DK1423407T3 (da)	2006-07-03
PT1423407E (pt)	2006-07-31
NO325012B1 (no)	2008-01-14
HUP0300936A2 (hu)	2003-11-28
NO20030989D0 (no)	2003-03-03
NO20030989L (no)	2003-05-02
WO2002019971A9 (fr)	2002-08-08
BG107594A (bg)	2003-09-30
NZ524485A (en)	2005-11-25
EE200300087A (et)	2005-02-15
JP2004513084A (ja)	2004-04-30
ZA200301715B (en)	2004-08-13
CA2421302A1 (fr)	2003-03-03
KR20030028836A (ko)	2003-04-10
EP1423407A1 (fr)	2004-06-02
RS50305B (sr)	2009-09-08
PL360669A1 (en)	2004-09-20
AU2002210470B2 (en)	2006-07-20
EA006387B1 (ru)	2005-12-29
IL154666A (en)	2008-12-29
HUP0300936A3 (en)	2010-01-28
HK1060135A1 (en)	2004-07-30
EP1423407B1 (fr)	2006-03-08
ATE319733T1 (de)	2006-03-15
WO2002019971A1 (fr)	2002-03-14
BR0113618A (pt)	2003-07-15
SK2442003A3 (en)	2003-08-05
KR100530816B1 (ko)	2005-11-25
EE05186B1 (et)	2009-06-15
CN1452628A (zh)	2003-10-29
YU16403A (sh)	2006-05-25
UA74592C2 (en)	2006-01-16
MEP14408A (en)	2010-06-10
ES2260294T3 (es)	2006-11-01
AU1047002A (en)	2002-03-22
HRP20030256A2 (en)	2005-10-31
IL154666A0 (en)	2003-09-17

Publication	Publication Date	Title
EP1272504B1 (fr)	2007-05-30	Estratrienes a substitution 8beta-hydrocarbyle utilises comme oestrogenes a action selective
US6855836B2 (en)	2005-02-15	17-Methylene steroids, process for their production and pharmaceutical compositions that contain these compounds
EP1169336B1 (fr)	2006-02-01	Ent-steroides utilises comme oestrogenes selectivement actifs
DE19906159A1 (de)	2000-08-10	16-Hydroxyestratriene als selektiv wirksame Estrogene
CA2384184C (fr)	2008-07-08	17.beta.-acyl-17.alpha.-propynyl-11.beta.-(cyclic amino) aryl-steroides et leurs derives presentant des proprietes hormonales antagonistes
EP1226155B1 (fr)	2007-05-02	18-nor-steroides utilises comme oestrogenes a effet selectif
AU2003242683B9 (en)	2009-08-27	9-Alpha-substituted estratrienes as selectively active estrogen
SK286757B6 (sk)	2009-05-07	17-Metylénsteroidy, spôsob ich prípravy, farmaceutické kompozície, ktoré ich obsahujú, a ich použitie
US7199115B2 (en)	2007-04-03	17α-fluorosteroids, pharmaceutical compositions containing 17α-fluorosteroids and a method of making them
DE10019167A1 (de)	2001-10-18	Substituierte Estratriene als selektiv wirksame Estrogene
EP1737880B1 (fr)	2010-04-14	17alpha-fluoro-17beta-hydroximinomethyl-steroides, leur procede de production, et compositions pharmaceutiques les contenant
NZ536882A (en)	2007-07-27	9-Alpha-substituted estratrienes as selectively active estrogens

Legal Events

Date	Code	Title	Description
2011-05-06	MM4A	Patent lapsed due to non-payment of maintenance fees	Effective date: 20100829