ZA200301715B - 4-Halogenated 17-Methylene steroids, method for the production thereof and pharmaceutical compositions containing these compounds. - Google Patents
4-Halogenated 17-Methylene steroids, method for the production thereof and pharmaceutical compositions containing these compounds. Download PDFInfo
- Publication number
- ZA200301715B ZA200301715B ZA200301715A ZA200301715A ZA200301715B ZA 200301715 B ZA200301715 B ZA 200301715B ZA 200301715 A ZA200301715 A ZA 200301715A ZA 200301715 A ZA200301715 A ZA 200301715A ZA 200301715 B ZA200301715 B ZA 200301715B
- Authority
- ZA
- South Africa
- Prior art keywords
- chloroestr
- composition
- methylene
- compound
- substance
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 26
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 11
- 125000002577 pseudohalo group Chemical group 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 230000005764 inhibitory process Effects 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 4
- 201000004384 Alopecia Diseases 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 206010020112 Hirsutism Diseases 0.000 claims description 4
- 206010000496 acne Diseases 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 231100000360 alopecia Toxicity 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 208000017497 prostate disease Diseases 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- -1 methylene steroid Chemical class 0.000 claims description 3
- NEDCCQPWOSRTHL-NMUAUPANSA-N (2e)-2-[(8r,9s,10r,13s,14s)-4-chloro-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ylidene]acetonitrile Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)(C(/CC4)=C/C#N)[C@@H]4[C@@H]3CCC2=C1Cl NEDCCQPWOSRTHL-NMUAUPANSA-N 0.000 claims description 2
- 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 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 6
- 239000000010 aprotic solvent Substances 0.000 claims 6
- 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 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 230000018044 dehydration Effects 0.000 claims 2
- 238000006297 dehydration reaction Methods 0.000 claims 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 2
- 239000011707 mineral Substances 0.000 claims 2
- 239000012434 nucleophilic reagent Substances 0.000 claims 2
- 239000003586 protic polar solvent Substances 0.000 claims 2
- 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 1
- 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 1
- 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
- YMGACAXXGFIDDN-XDFMKLRHSA-N (8s,9s,10r,13s,14s,17e)-4-chloro-17-(chloromethylidene)-10,13-dimethyl-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/Cl)[C@@H]4[C@@H]3CCC2=C1Cl YMGACAXXGFIDDN-XDFMKLRHSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 239000000969 carrier Substances 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 2
- 239000003098 androgen Substances 0.000 description 2
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 210000003754 fetus Anatomy 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000000583 progesterone congener Substances 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- NEDCCQPWOSRTHL-CMQYSOMSSA-N (2z)-2-[(8r,9s,10r,13s,14s)-4-chloro-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ylidene]acetonitrile Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)(C(/CC4)=C\C#N)[C@@H]4[C@@H]3CCC2=C1Cl NEDCCQPWOSRTHL-CMQYSOMSSA-N 0.000 description 1
- XMRPGKVKISIQBV-BJMCWZGWSA-N 5alpha-pregnane-3,20-dione Chemical compound C([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)C)[C@@]2(C)CC1 XMRPGKVKISIQBV-BJMCWZGWSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010036618 Premenstrual syndrome Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000002280 anti-androgenic effect Effects 0.000 description 1
- 230000003509 anti-fertility effect Effects 0.000 description 1
- 150000001540 azides Chemical class 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
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229940124558 contraceptive agent Drugs 0.000 description 1
- 239000003433 contraceptive agent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 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
- 210000002149 gonad Anatomy 0.000 description 1
- 230000002710 gonadal effect Effects 0.000 description 1
- 230000003054 hormonal effect Effects 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
- 239000000314 lubricant Substances 0.000 description 1
- 230000006351 negative regulation of hormone secretion Effects 0.000 description 1
- 210000000056 organ Anatomy 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
- 238000002360 preparation method Methods 0.000 description 1
- 230000001072 progestational effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000036301 sexual development Effects 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 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
- 208000024891 symptom Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 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
- 229960003604 testosterone Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000036642 wellbeing Effects 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)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Reproductive Health (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Gynecology & Obstetrics (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200301715B true ZA200301715B (en) | 2004-08-13 |
Family
ID=7655148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200301715A ZA200301715B (en) | 2000-09-04 | 2003-02-28 | 4-Halogenated 17-Methylene steroids, method for the production thereof and pharmaceutical compositions containing these compounds. |
Country Status (29)
| Country | Link |
|---|---|
| EP (1) | EP1423407B1 (es) |
| JP (1) | JP2004513084A (es) |
| KR (1) | KR100530816B1 (es) |
| CN (1) | CN1262560C (es) |
| AT (1) | ATE319733T1 (es) |
| AU (2) | AU1047002A (es) |
| BG (1) | BG107594A (es) |
| BR (1) | BR0113618A (es) |
| CA (1) | CA2421302C (es) |
| DE (2) | DE10043846A1 (es) |
| DK (1) | DK1423407T3 (es) |
| EA (1) | EA006387B1 (es) |
| EE (1) | EE05186B1 (es) |
| ES (1) | ES2260294T3 (es) |
| HK (1) | HK1060135A1 (es) |
| HR (1) | HRP20030256A2 (es) |
| HU (1) | HUP0300936A3 (es) |
| IL (2) | IL154666A0 (es) |
| ME (1) | MEP14408A (es) |
| MX (1) | MXPA03001912A (es) |
| NO (1) | NO325012B1 (es) |
| NZ (1) | NZ524485A (es) |
| PL (1) | PL360669A1 (es) |
| PT (1) | PT1423407E (es) |
| RS (1) | RS50305B (es) |
| SK (1) | SK286757B6 (es) |
| UA (1) | UA74592C2 (es) |
| WO (1) | WO2002019971A1 (es) |
| ZA (1) | ZA200301715B (es) |
Families Citing this family (3)
| 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)
| 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 |
| EP1409512A1 (en) * | 2000-06-27 | 2004-04-21 | 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 AU AU1047002A patent/AU1047002A/xx active Pending
- 2001-08-29 ME MEP-144/08A patent/MEP14408A/xx unknown
- 2001-08-29 PL PL36066901A patent/PL360669A1/xx unknown
- 2001-08-29 EA EA200300322A patent/EA006387B1/ru not_active IP Right Cessation
- 2001-08-29 DK DK01978315T patent/DK1423407T3/da active
- 2001-08-29 MX MXPA03001912A patent/MXPA03001912A/es active IP Right Grant
- 2001-08-29 KR KR10-2003-7003170A patent/KR100530816B1/ko not_active IP Right Cessation
- 2001-08-29 JP JP2002524456A patent/JP2004513084A/ja active Pending
- 2001-08-29 CN CNB018151345A patent/CN1262560C/zh not_active Expired - Fee Related
- 2001-08-29 PT PT01978315T patent/PT1423407E/pt unknown
- 2001-08-29 NZ NZ524485A patent/NZ524485A/en unknown
- 2001-08-29 UA UA2003042852A patent/UA74592C2/uk unknown
- 2001-08-29 EP EP01978315A patent/EP1423407B1/de not_active Expired - Lifetime
- 2001-08-29 ES ES01978315T patent/ES2260294T3/es not_active Expired - Lifetime
- 2001-08-29 DE DE50109175T patent/DE50109175D1/de not_active Expired - Lifetime
- 2001-08-29 BR BR0113618-6A patent/BR0113618A/pt not_active IP Right Cessation
- 2001-08-29 SK SK244-2003A patent/SK286757B6/sk not_active IP Right Cessation
- 2001-08-29 AT AT01978315T patent/ATE319733T1/de not_active IP Right Cessation
- 2001-08-29 AU AU2002210470A patent/AU2002210470B2/en not_active Ceased
- 2001-08-29 HU HU0300936A patent/HUP0300936A3/hu unknown
- 2001-08-29 CA CA002421302A patent/CA2421302C/en not_active Expired - Fee Related
- 2001-08-29 EE EEP200300087A patent/EE05186B1/xx not_active IP Right Cessation
- 2001-08-29 WO PCT/EP2001/009943 patent/WO2002019971A1/de active IP Right Grant
- 2001-08-29 RS YUP-164/03A patent/RS50305B/sr unknown
- 2001-08-29 IL IL15466601A patent/IL154666A0/xx unknown
-
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
- 2003-04-04 HR HR20030256A patent/HRP20030256A2/hr not_active Application Discontinuation
-
2004
- 2004-04-27 HK HK04102956A patent/HK1060135A1/xx not_active IP Right Cessation
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