DE68927861T2 - 11 beta-substituierte progesteron-analoge - Google Patents
11 beta-substituierte progesteron-analogeInfo
- Publication number
- DE68927861T2 DE68927861T2 DE68927861T DE68927861T DE68927861T2 DE 68927861 T2 DE68927861 T2 DE 68927861T2 DE 68927861 T DE68927861 T DE 68927861T DE 68927861 T DE68927861 T DE 68927861T DE 68927861 T2 DE68927861 T2 DE 68927861T2
- Authority
- DE
- Germany
- Prior art keywords
- norprogesterone
- norpregna
- dione
- progesterone
- dimethylaminophenyl
- 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.)
- Expired - Lifetime
Links
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 title claims description 57
- -1 R4 is H Chemical group 0.000 claims abstract description 21
- 125000003118 aryl group Chemical group 0.000 claims abstract description 20
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 16
- MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical compound C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 claims abstract description 16
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims abstract description 16
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims abstract description 14
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract description 11
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 93
- 230000000694 effects Effects 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 34
- 239000003418 antiprogestin Substances 0.000 claims description 33
- 230000003623 progesteronic effect Effects 0.000 claims description 33
- 239000000186 progesterone Substances 0.000 claims description 28
- 229960003387 progesterone Drugs 0.000 claims description 28
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 19
- 230000027455 binding Effects 0.000 claims description 14
- 102000003998 progesterone receptors Human genes 0.000 claims description 14
- 108090000468 progesterone receptors Proteins 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000003862 glucocorticoid Substances 0.000 claims description 7
- 108090000079 Glucocorticoid Receptors Proteins 0.000 claims description 6
- 208000014311 Cushing syndrome Diseases 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 201000009395 primary hyperaldosteronism Diseases 0.000 claims description 5
- 230000004044 response Effects 0.000 claims description 4
- 208000010412 Glaucoma Diseases 0.000 claims description 3
- HKDLNTKNLJPAIY-WKWWZUSTSA-N Ulipristal Chemical compound C1=CC(N(C)C)=CC=C1[C@@H]1C2=C3CCC(=O)C=C3CC[C@H]2[C@H](CC[C@]2(O)C(C)=O)[C@]2(C)C1 HKDLNTKNLJPAIY-WKWWZUSTSA-N 0.000 claims description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
- 230000003388 anti-hormonal effect Effects 0.000 claims description 3
- 229940088597 hormone Drugs 0.000 claims description 2
- 239000005556 hormone Substances 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 230000001939 inductive effect Effects 0.000 claims 2
- 102100033417 Glucocorticoid receptor Human genes 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 64
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- 239000000243 solution Substances 0.000 description 51
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 46
- 150000001875 compounds Chemical class 0.000 description 40
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- 238000005160 1H NMR spectroscopy Methods 0.000 description 34
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- 239000000047 product Substances 0.000 description 26
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- 150000003431 steroids Chemical class 0.000 description 23
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 16
- 235000011152 sodium sulphate Nutrition 0.000 description 16
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- 239000011541 reaction mixture Substances 0.000 description 15
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
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- FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
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- 102000003676 Glucocorticoid Receptors Human genes 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
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- 239000000969 carrier Substances 0.000 description 5
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- 229910052744 lithium Inorganic materials 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- 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
- C07J41/0077—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom
- C07J41/0083—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom substituted in position 11-beta by an optionally substituted phenyl group not further condensed with other rings
-
- 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
-
- 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
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- 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
-
- 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
- C07J13/005—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 16 (17)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
- C07J53/004—3 membered carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa
- C07J7/002—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa not substituted in position 16
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/004—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa
- C07J7/0045—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa not substituted in position 16
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0036—Nitrogen-containing hetero ring
- C07J71/0042—Nitrogen only
- C07J71/0052—Nitrogen only at position 16(17)
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Reproductive Health (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Control Of Eletrric Generators (AREA)
- Sub-Exchange Stations And Push- Button Telephones (AREA)
- Devices For Supply Of Signal Current (AREA)
- Light Receiving Elements (AREA)
- Led Devices (AREA)
- Junction Field-Effect Transistors (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Seasonings (AREA)
- Manufacture Of Tobacco Products (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/210,503 US4954490A (en) | 1988-06-23 | 1988-06-23 | 11 β-substituted progesterone analogs |
| PCT/US1989/002706 WO1989012448A1 (en) | 1988-06-23 | 1989-06-23 | 11beta-SUBSTITUTED PROGESTERONE ANALOGS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE68927861D1 DE68927861D1 (de) | 1997-04-17 |
| DE68927861T2 true DE68927861T2 (de) | 1997-10-16 |
Family
ID=22783162
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE68927861T Expired - Lifetime DE68927861T2 (de) | 1988-06-23 | 1989-06-23 | 11 beta-substituierte progesteron-analoge |
| DE122009000031C Active DE122009000031I2 (de) | 1988-06-23 | 1989-06-23 | 11 beta-substituierte progesteron-analoge |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE122009000031C Active DE122009000031I2 (de) | 1988-06-23 | 1989-06-23 | 11 beta-substituierte progesteron-analoge |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US4954490A (https=) |
| EP (1) | EP0422100B1 (https=) |
| JP (1) | JP2953725B2 (https=) |
| KR (1) | KR0161975B1 (https=) |
| AT (1) | ATE149839T1 (https=) |
| AU (1) | AU635211B2 (https=) |
| CA (1) | CA1338906C (https=) |
| DE (2) | DE68927861T2 (https=) |
| DK (1) | DK175760B1 (https=) |
| LU (1) | LU91575I2 (https=) |
| NL (1) | NL300392I2 (https=) |
| NO (2) | NO178264C (https=) |
| WO (1) | WO1989012448A1 (https=) |
Families Citing this family (90)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3832303A1 (de) * | 1988-09-20 | 1990-04-12 | Schering Ag | 11ss-phenyl-14ssh-steroide |
| ATE172469T1 (de) * | 1989-08-04 | 1998-11-15 | Schering Ag | 11 beta-aryl-gona-4,9-dien-3-one |
| USRE34578E (en) * | 1990-05-07 | 1994-04-05 | Lubkin; Virginia | Drugs for topical application of sex steroids in the treatment of dry eye syndrome, and methods of preparation and application |
| US5041434A (en) * | 1991-08-17 | 1991-08-20 | Virginia Lubkin | Drugs for topical application of sex steroids in the treatment of dry eye syndrome, and methods of preparation and application |
| DE4042004A1 (de) * | 1990-12-22 | 1992-06-25 | Schering Ag | 14(beta)-h-, 14- u. 15-en-11(beta)-aryl-4-estrene |
| US5407928A (en) * | 1990-08-15 | 1995-04-18 | Schering Aktiengesellschaft | 11β-aryl-gona-4,9-dien-3-ones |
| JPH07508716A (ja) * | 1992-04-21 | 1995-09-28 | ザ スキーペンズ アイ リサーチ インスティテュート，インコーポレイテッド | シェーグレン症候群における眼のアンドロゲン療法 |
| US5536725A (en) * | 1993-08-25 | 1996-07-16 | Fmc Corporation | Insecticidal substituted-2,4-diamino-5,6,7,8-tetrahydroquinazolines |
| US5639598A (en) * | 1994-05-19 | 1997-06-17 | The Trustees Of The University Of Pennsylvania | Method and kit for identification of antiviral agents capable of abrogating HIV Vpr-Rip-1 binding interactions |
| DE69500542T2 (de) * | 1994-05-19 | 1998-01-02 | Akzo Nobel Nv | 11,21-Bisphenyl-19-nor-pregnan Derivate |
| US5780220A (en) * | 1994-05-19 | 1998-07-14 | Trustees Of The University Of Pennsylvania | Methods and compositions for inhibiting HIV replication |
| US5929262A (en) * | 1995-03-30 | 1999-07-27 | The United States Of America As Represented By The Department Of Health And Human Services | Method for preparing 17α-acetoxy-11β-(4-N, N-dimethylaminophyl)-19-Norpregna-4,9-diene-3, 20-dione, intermediates useful in the method, and methods for the preparation of such intermediates |
| US6900193B1 (en) * | 1996-05-01 | 2005-05-31 | The United States Of America As Represented By The Department Of Health And Human Services | Structural modification of 19-norprogesterone I: 17-α-substituted-11-β-substituted-4-aryl and 21-substituted 19-norpregnadienedione as new antiprogestational agents |
| AU710139B2 (en) * | 1996-05-01 | 1999-09-16 | Government Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services, The | 21-substituted progesterone derivatives as new antiprogestational agents |
| WO1998005679A2 (en) * | 1996-08-05 | 1998-02-12 | Duke University | Mixed agonists of the progesterone receptor and assays therefor |
| US6090798A (en) * | 1997-12-19 | 2000-07-18 | Alcon Laboratories, Inc. | Treatment of GLC1A glaucoma with glucocorticoid antagonists |
| US6020328A (en) | 1998-03-06 | 2000-02-01 | Research Triangle Institute | 20-keto-11β-arylsteroids and their derivatives having agonist or antagonist hormonal properties |
| US6262042B1 (en) * | 1998-05-29 | 2001-07-17 | Research Triangle Institute | 17β-amino and hydroxylamino-11β-arylsteroids and their derivatives having agonist or antagonist hormonal properties |
| US5962444A (en) * | 1998-05-29 | 1999-10-05 | Research Triangle Institute | 17β-nitro-11β-arylsteroids and their derivatives having agonist or antagonist hormonal properties |
| US6172052B1 (en) * | 1998-12-04 | 2001-01-09 | Research Triangle Institute | 17β-acyl-17α-propynyl-11β-arylsteroids and their derivatives having agonist or antagonist hormonal properties |
| US6740645B1 (en) * | 1999-09-03 | 2004-05-25 | Research Triangle Institute | 17β-acyl-17α-propynyl-11β-(cyclic amino) aryl steroids and their derivatives having antagonist hormonal properties |
| AU4584901A (en) * | 2000-03-17 | 2001-10-15 | Us Gov Health & Human Serv | Structural modification of 19-norprogesterone i: 17-alpha-substituted-11-beta-substituted-4-aryl and 21-substituted 19-norpregnadienedione as new antiprogestational agents |
| MXPA03007261A (es) * | 2001-02-14 | 2006-03-09 | Abbott Lab | Moduladores del receptor de glucocorticoides. |
| ES2212912B1 (es) * | 2003-01-22 | 2005-10-01 | Crystal Pharma, S.A. | Procedimiento para la obtencion de 17alfa-acetoxi-11beta-(4-n,n-dimetilaminofenil)-19-norpregna-4,9-dien-3,20-diona. |
| AU2004217988C1 (en) | 2003-02-28 | 2010-06-03 | Southwest Foundation For Biomedical Research | Method for preparing 17 alpha-acetoxy-11beta-(4-N,N-dimethylaminophenyl)-19-norpregna-4,9-diene-3,20-dione, intermediates thereof, and methods for the preparation of such intermediates |
| US20060247452A1 (en) * | 2004-01-21 | 2006-11-02 | Guisasola Luis Octavio S | Method for obtaining 17sg(a)-acetoxy-11$g(b)-(4-n,n-dimethylaminophenyl)-19-norpregna-4,9-diene-3,20-dione |
| US8865200B2 (en) | 2004-07-09 | 2014-10-21 | Laboratoire Hra Pharma | Sustained release compositions containing progesterone receptor modulators |
| EP1862468A1 (de) * | 2006-06-02 | 2007-12-05 | Bayer Schering Pharma Aktiengesellschaft | Kristallines 11beta-(4-Acetylphenyl)-20,20,21,21,21-pentafluor-17-hydroxy-19-nor-17alpha-pregna-4,9-dien-3-on |
| HU227112B1 (hu) * | 2006-06-14 | 2010-07-28 | Richter Gedeon Nyrt | Ipari eljárás 17-alfa-acetoxi-11-béta-[4-(N,N-dimetil-amino)-fenil]-19-norpregna-4,9-dién-3,20-dion elõállítására és új intermedierek az eljáráshoz |
| PT2148681E (pt) * | 2007-04-20 | 2016-06-17 | Preglem Sa | Moduladores seletivos da progesterona no tratamento da hemorragia uterina |
| HU228636B1 (en) * | 2007-06-27 | 2013-04-29 | Richter Gedeon Nyrt | Industrial method for the synthesis of 17-acetoxy-11betha-4[-(dimethylamino)-phenyl]-21-methoxy-19-norpregna-4,9-dien-3,20-dione and the key intermediates of the process |
| EP2532350A1 (en) | 2007-10-17 | 2012-12-12 | Laboratoire HRA Pharma | Pharmaceutical combination of a glucocorticoid receptor antagonist and a cortisol synthesis inhibitor for treating cushing's syndrome |
| US8299050B2 (en) | 2008-01-29 | 2012-10-30 | Laboratoire Hra-Pharma | Method for treating uterine fibroids |
| US8512745B2 (en) * | 2008-12-08 | 2013-08-20 | Laboratoire Hra Pharma | Ulipristal acetate tablets |
| BRPI1014035A2 (pt) | 2009-04-14 | 2016-04-12 | Hra Pharma Lab | método para contracepção. |
| DE102009034362A1 (de) | 2009-07-20 | 2011-01-27 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-aryl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Behandlung von Krankheiten |
| DE102009034367A1 (de) | 2009-07-20 | 2011-01-27 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-benzyliden-Derivate, Verfahren zu deren Herstellung und deren Verwendung zur Behandlung von Krankheiten |
| DE102009034368A1 (de) | 2009-07-20 | 2011-01-27 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-acyloxyalkylenphenyl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Behandlung von Krankheiten |
| DE102009034366A1 (de) | 2009-07-20 | 2011-01-27 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-methylenoxyalkylenaryl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Behandlung von Krankheiten |
| DE102009034525A1 (de) | 2009-07-21 | 2011-01-27 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-aryl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Behandlung von Krankheiten |
| DE102009034526A1 (de) | 2009-07-21 | 2011-02-10 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-ethinylphenyl-Derivate, Verfahren zu deren Herstellung und deren Verwendung zur Behandlung von Krankheiten |
| US8426392B2 (en) | 2009-12-09 | 2013-04-23 | Laboratoire Hra-Pharma | Method for providing emergency contraception |
| US8962603B2 (en) | 2010-02-01 | 2015-02-24 | Laboratoire Hra-Pharma | Method for post coital contraception in overweight or obese female subjects using ulipristal acetate |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2377418A1 (fr) * | 1977-01-13 | 1978-08-11 | Roussel Uclaf | Nouveaux derives steroides 4,9-dieniques 11b-substitues, leur procede de preparation et leur application comme medicaments |
| ZA8231B (en) * | 1981-01-09 | 1982-11-24 | Roussel Uclaf | New 11 -substituted steroid derivatives, their preparation, their use as medicaments, the compositions containing them and the new intermediates thus obtained |
| FR2522328B1 (fr) * | 1982-03-01 | 1986-02-14 | Roussel Uclaf | Nouveaux produits derives de la structure 3-ceto 4,9 19-nor steroides, leur procede de preparation et leur application comme medicaments |
| ES533260A0 (es) * | 1983-06-15 | 1985-02-01 | Schering Ag | Procedimiento para la preparacion de 13a-alquilgonanos |
| FR2586021B1 (fr) * | 1985-08-09 | 1988-10-14 | Roussel Uclaf | Nouveaux produits derives de la structure 5a-oh d 9(10) 19-nor steroides |
| IE60780B1 (en) * | 1987-01-23 | 1994-08-10 | Akzo Nv | New 11-aryl steroid derivatives |
-
1988
- 1988-06-23 US US07/210,503 patent/US4954490A/en not_active Expired - Lifetime
-
1989
- 1989-06-22 CA CA000603686A patent/CA1338906C/en not_active Expired - Lifetime
- 1989-06-23 KR KR1019900700406A patent/KR0161975B1/ko not_active Expired - Lifetime
- 1989-06-23 EP EP89907924A patent/EP0422100B1/en not_active Expired - Lifetime
- 1989-06-23 AT AT89907924T patent/ATE149839T1/de active
- 1989-06-23 DE DE68927861T patent/DE68927861T2/de not_active Expired - Lifetime
- 1989-06-23 DE DE122009000031C patent/DE122009000031I2/de active Active
- 1989-06-23 AU AU38506/89A patent/AU635211B2/en not_active Expired
- 1989-06-23 WO PCT/US1989/002706 patent/WO1989012448A1/en not_active Ceased
- 1989-06-23 JP JP1507392A patent/JP2953725B2/ja not_active Expired - Fee Related
-
1990
- 1990-04-03 US US07/504,129 patent/US5073548A/en not_active Expired - Lifetime
- 1990-12-21 NO NO905546A patent/NO178264C/no not_active IP Right Cessation
- 1990-12-21 DK DK199003053A patent/DK175760B1/da active Protection Beyond IP Right Term
-
2009
- 2009-06-03 LU LU91575C patent/LU91575I2/fr unknown
- 2009-06-11 NL NL300392C patent/NL300392I2/nl unknown
- 2009-06-22 NO NO2009014C patent/NO2009014I2/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE122009000031I1 (de) | 2009-11-05 |
| JP2953725B2 (ja) | 1999-09-27 |
| EP0422100B1 (en) | 1997-03-12 |
| KR900701820A (ko) | 1990-12-04 |
| DE68927861D1 (de) | 1997-04-17 |
| NO178264B (no) | 1995-11-13 |
| NO178264C (no) | 1996-02-21 |
| AU3850689A (en) | 1990-01-12 |
| WO1989012448A1 (en) | 1989-12-28 |
| DK305390D0 (da) | 1990-12-21 |
| NO905546D0 (no) | 1990-12-21 |
| DE122009000031I2 (de) | 2011-06-16 |
| NL300392I1 (nl) | 2009-08-03 |
| LU91575I2 (fr) | 2009-08-03 |
| NL300392I2 (nl) | 2009-10-01 |
| ATE149839T1 (de) | 1997-03-15 |
| AU635211B2 (en) | 1993-03-18 |
| JPH03505582A (ja) | 1991-12-05 |
| KR0161975B1 (ko) | 1998-11-16 |
| NO905546L (no) | 1990-12-21 |
| EP0422100A1 (en) | 1991-04-17 |
| EP0422100A4 (https=) | 1994-04-27 |
| US4954490A (en) | 1990-09-04 |
| DK175760B1 (da) | 2005-02-14 |
| US5073548A (en) | 1991-12-17 |
| NO2009014I2 (no) | 2009-12-28 |
| NO2009014I1 (no) | 2009-07-06 |
| CA1338906C (en) | 1997-02-11 |
| DK305390A (da) | 1990-12-21 |
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