LV13527B - Progesterone receptor modulators - Google Patents

Progesterone receptor modulators Download PDF

Info

Publication number: LV13527B
Authority: LV; Latvia
Prior art keywords: alkyl; optionally substituted; compound according; halogen; cyclopropyl
Prior art date: 2004-03-25

Application number

LVP-06-120A

Other languages

English (en)

Latvian (lv)

Inventor

Johannes Antonius Mar Hamersma

Johannes Bernardus Ma Rewinkel

Original Assignee

Organon Nv

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.)

2004-03-25

Filing date

2006-10-24

Publication date

2007-04-20

2006-10-24 Application filed by Organon Nv filed Critical Organon Nv

2007-04-20 Publication of LV13527B publication Critical patent/LV13527B/lv

Links

239000002379 progesterone receptor modulator Substances 0.000 title description 3
229940095745 sex hormone and modulator of the genital system progesterone receptor modulator Drugs 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 171
125000000217 alkyl group Chemical group 0.000 claims abstract description 109
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 42
125000005843 halogen group Chemical group 0.000 claims abstract description 40
229910052736 halogen Inorganic materials 0.000 claims abstract description 38
125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 claims abstract description 25
229920006395 saturated elastomer Polymers 0.000 claims abstract description 25
150000002367 halogens Chemical class 0.000 claims abstract description 23
125000003342 alkenyl group Chemical group 0.000 claims abstract description 20
125000003118 aryl group Chemical group 0.000 claims abstract description 20
125000001054 5 membered carbocyclic group Chemical group 0.000 claims abstract description 17
125000004011 3 membered carbocyclic group Chemical group 0.000 claims abstract description 15
125000001845 4 membered carbocyclic group Chemical group 0.000 claims abstract description 15
125000004008 6 membered carbocyclic group Chemical group 0.000 claims abstract description 15
150000003839 salts Chemical class 0.000 claims abstract description 13
125000002837 carbocyclic group Chemical group 0.000 claims abstract description 12
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 9
125000002252 acyl group Chemical group 0.000 claims abstract description 8
125000005605 benzo group Chemical group 0.000 claims abstract description 8
239000000651 prodrug Substances 0.000 claims abstract description 7
229940002612 prodrug Drugs 0.000 claims abstract description 7
125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
238000000034 method Methods 0.000 claims description 41
239000008194 pharmaceutical composition Substances 0.000 claims description 16
238000011282 treatment Methods 0.000 claims description 16
239000003814 drug Substances 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 8
238000002560 therapeutic procedure Methods 0.000 claims description 7
238000002657 hormone replacement therapy Methods 0.000 claims description 6
239000003433 contraceptive agent Substances 0.000 claims description 4
230000002254 contraceptive effect Effects 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
-1 acetyloxy, acetyloxymethyl Chemical group 0.000 description 56
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 47
238000005481 NMR spectroscopy Methods 0.000 description 43
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 40
239000000243 solution Substances 0.000 description 39
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 description 31
238000002360 preparation method Methods 0.000 description 28
DBLOJPKZEOYNBN-SQNIBIBYSA-N (8s,13s,14s)-13-methyl-2,6,7,8,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CCC2=C2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 DBLOJPKZEOYNBN-SQNIBIBYSA-N 0.000 description 26
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 26
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 25
239000012044 organic layer Substances 0.000 description 20
238000000746 purification Methods 0.000 description 20
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108020003175 receptors Proteins 0.000 description 20
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239000000203 mixture Substances 0.000 description 17
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238000004108 freeze drying Methods 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
229910052799 carbon Inorganic materials 0.000 description 14
230000000694 effects Effects 0.000 description 14
108090000468 progesterone receptors Proteins 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
229910052739 hydrogen Inorganic materials 0.000 description 13
239000012299 nitrogen atmosphere Substances 0.000 description 13
102000003998 progesterone receptors Human genes 0.000 description 13
230000001270 agonistic effect Effects 0.000 description 12
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238000004440 column chromatography Methods 0.000 description 11
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 11
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
230000001838 anti-progestagenic effect Effects 0.000 description 10
230000027455 binding Effects 0.000 description 10
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150000002632 lipids Chemical class 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
230000003042 antagnostic effect Effects 0.000 description 9
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238000003756 stirring Methods 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000012267 brine Substances 0.000 description 8
239000000583 progesterone congener Substances 0.000 description 8
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
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125000004432 carbon atom Chemical group C* 0.000 description 7
238000004128 high performance liquid chromatography Methods 0.000 description 7
239000003446 ligand Substances 0.000 description 7
239000011734 sodium Substances 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
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108020004414 DNA Proteins 0.000 description 6
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229910004298 SiO 2 Inorganic materials 0.000 description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
230000014509 gene expression Effects 0.000 description 6
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DHADXDMPEUWEAS-UHFFFAOYSA-N (6-methoxypyridin-3-yl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=N1 DHADXDMPEUWEAS-UHFFFAOYSA-N 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
239000005557 antagonist Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
229940088597 hormone Drugs 0.000 description 5
239000005556 hormone Substances 0.000 description 5
230000023603 positive regulation of transcription initiation, DNA-dependent Effects 0.000 description 5
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150000003431 steroids Chemical class 0.000 description 5
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
108700008625 Reporter Genes Proteins 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
239000000556 agonist Substances 0.000 description 4
238000003556 assay Methods 0.000 description 4
239000008280 blood Substances 0.000 description 4
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102000004169 proteins and genes Human genes 0.000 description 4
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235000011152 sodium sulphate Nutrition 0.000 description 4
239000002904 solvent Substances 0.000 description 4
230000003637 steroidlike Effects 0.000 description 4
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RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
102100032187 Androgen receptor Human genes 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
201000009273 Endometriosis Diseases 0.000 description 3
102000003676 Glucocorticoid Receptors Human genes 0.000 description 3
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239000007832 Na2SO4 Substances 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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108010080146 androgen receptors Proteins 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
230000033228 biological regulation Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
230000001419 dependent effect Effects 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
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230000005764 inhibitory process Effects 0.000 description 3
108020004999 messenger RNA Proteins 0.000 description 3
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210000001672 ovary Anatomy 0.000 description 3
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125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
WPAPNCXMYWRTTL-UHFFFAOYSA-N (6-chloropyridin-3-yl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)N=C1 WPAPNCXMYWRTTL-UHFFFAOYSA-N 0.000 description 2
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KZJRKRQSDZGHEC-UHFFFAOYSA-N 2,2,2-trifluoro-1-phenylethanone Chemical compound FC(F)(F)C(=O)C1=CC=CC=C1 KZJRKRQSDZGHEC-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
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QQIRAVWVGBTHMJ-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane;lithium Chemical group [Li].C[Si](C)(C)N[Si](C)(C)C QQIRAVWVGBTHMJ-UHFFFAOYSA-N 0.000 description 2
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YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
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125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000001890 transfection Methods 0.000 description 1
238000013519 translation Methods 0.000 description 1
DBHSVKZZSWTSTN-UHFFFAOYSA-N tributyl(pyridazin-3-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CN=N1 DBHSVKZZSWTSTN-UHFFFAOYSA-N 0.000 description 1
UDLLSOQWYYRFPP-UHFFFAOYSA-N tributyl(pyridazin-4-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=NN=C1 UDLLSOQWYYRFPP-UHFFFAOYSA-N 0.000 description 1
WTFFOOAJSDVASL-UHFFFAOYSA-N tributyl(pyrimidin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=NC=CC=N1 WTFFOOAJSDVASL-UHFFFAOYSA-N 0.000 description 1
BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 description 1
BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
229940056345 tums Drugs 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
210000001215 vagina Anatomy 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
150000003722 vitamin derivatives Chemical class 0.000 description 1
ZQJYTTPJYLKTTI-UHFFFAOYSA-M zinc;2h-pyridin-2-ide;bromide Chemical compound Br[Zn+].C1=CC=N[C-]=C1 ZQJYTTPJYLKTTI-UHFFFAOYSA-M 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
- 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
- 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
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
- 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
- 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
- C07J53/001—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 spiro-linked

Landscapes

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

LVP-06-120A 2004-03-25 2006-10-24 Progesterone receptor modulators LV13527B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP04101241		2004-03-25

Publications (1)

Publication Number	Publication Date
LV13527B true LV13527B (en)	2007-04-20

Family

ID=34928929

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LVP-06-120A LV13527B (en)	2004-03-25	2006-10-24	Progesterone receptor modulators

Country Status (29)

Country	Link
US (1)	US7691836B2 (pt)
EP (1)	EP1735330B1 (pt)
JP (1)	JP4922918B2 (pt)
KR (1)	KR20070028355A (pt)
CN (1)	CN100549023C (pt)
AR (1)	AR048330A1 (pt)
AU (1)	AU2005225560B2 (pt)
BR (1)	BRPI0509153A (pt)
CA (1)	CA2560694C (pt)
CY (1)	CY1107132T1 (pt)
DE (1)	DE602005003564T2 (pt)
DK (1)	DK1735330T3 (pt)
EC (1)	ECSP066881A (pt)
ES (1)	ES2297699T3 (pt)
IL (1)	IL178010A0 (pt)
LV (1)	LV13527B (pt)
MX (1)	MXPA06010906A (pt)
MY (1)	MY143074A (pt)
NO (1)	NO20064822L (pt)
NZ (1)	NZ549862A (pt)
PE (1)	PE20060094A1 (pt)
PL (1)	PL1735330T3 (pt)
PT (1)	PT1735330E (pt)
RU (1)	RU2381232C2 (pt)
SI (1)	SI1735330T1 (pt)
TW (1)	TW200531977A (pt)
UA (1)	UA88782C2 (pt)
WO (1)	WO2005092912A1 (pt)
ZA (1)	ZA200607801B (pt)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2016090139A1 (en) *	2014-12-03	2016-06-09	Evestra, Inc.	Combination of estrogens plus antiprogestins with significant partial agonistic effect as an effective treatment of menopausal symptoms and for prevention of the occurrence of breast cancer

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE290198C (pt)
GB8513723D0 (en)	1985-05-31	1985-07-03	Erba Farmitalia	11-beta substituted steroids
IE60780B1 (en)	1987-01-23	1994-08-10	Akzo Nv	New 11-aryl steroid derivatives
EP0289073B1 (en)	1987-04-24	1991-11-27	Akzo N.V.	Novel 11-aryloestrane and 11-arylpregnane derivatives
EP0303306B1 (en)	1987-08-08	1993-03-10	Akzo N.V.	Contraceptive implant
DE3822770A1 (de) *	1988-07-01	1990-01-04	Schering Ag	13-alkyl-11ss-phenylgonane
DD290198A5 (de) *	1989-09-18	1991-05-23	Zi Fuer Mikrobiologie Und Experimentelle Therapie Jena,De	Verfahren zur herstellung von 11 beta-arylsubstituierten estra-4,9-dien-3-on-17(s)-spiro-1'-cyclohexan-2'-onen und 11 beta-arylsubstituierten estra-4,9-dien-3-on-17(s)-spiro-1'-cyclohexan-2'-olen sowie deren derivate
FR2658516B1 (fr)	1990-02-22	1992-06-12	Roussel Uclaf	Nouveaux produits sterouides comportant un radical spiro en position 17, leur procede de preparation et les intermediaires de ce procede, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant.
ZA929315B (en)	1991-12-20	1993-05-24	Akzo Nv	17-spirofuran-3'-ylidene steroids.
CA2100514C (en)	1992-07-29	2005-03-29	Johannes A. M. Hamersma	17-spiromethylene steroids
US5696130A (en)	1994-12-22	1997-12-09	Ligand Pharmaceuticals Incorporated	Tricyclic steroid receptor modulator compounds and methods
NZ332894A (en)	1996-06-25	1999-05-28	Akzo Nobel Nv	A regimen containing progestogen and/or estrogen with two or more anti-progestogen dosage units
IL123813A0 (en)	1997-04-11	1998-10-30	Akzo Nobel Nv	Drug delivery system for two or more active substances
TR200001334T2 (tr)	1997-11-14	2000-09-21	Akzo Nobel N.V.	Progestojen-anti-progestojen rejimleri.
US6020328A (en) *	1998-03-06	2000-02-01	Research Triangle Institute	20-keto-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

2005
- 2005-03-15 TW TW094107888A patent/TW200531977A/zh unknown
- 2005-03-18 US US10/594,103 patent/US7691836B2/en active Active
- 2005-03-18 RU RU2006137578/04A patent/RU2381232C2/ru not_active IP Right Cessation
- 2005-03-18 DE DE602005003564T patent/DE602005003564T2/de not_active Expired - Lifetime
- 2005-03-18 SI SI200530144T patent/SI1735330T1/sl unknown
- 2005-03-18 CA CA2560694A patent/CA2560694C/en not_active Expired - Fee Related
- 2005-03-18 MX MXPA06010906A patent/MXPA06010906A/es active IP Right Grant
- 2005-03-18 NZ NZ549862A patent/NZ549862A/en unknown
- 2005-03-18 CN CNB2005800096126A patent/CN100549023C/zh not_active Expired - Fee Related
- 2005-03-18 DK DK05733590T patent/DK1735330T3/da active
- 2005-03-18 EP EP05733590A patent/EP1735330B1/en not_active Expired - Lifetime
- 2005-03-18 JP JP2007504406A patent/JP4922918B2/ja not_active Expired - Fee Related
- 2005-03-18 BR BRPI0509153-5A patent/BRPI0509153A/pt not_active IP Right Cessation
- 2005-03-18 WO PCT/EP2005/051265 patent/WO2005092912A1/en not_active Ceased
- 2005-03-18 ES ES05733590T patent/ES2297699T3/es not_active Expired - Lifetime
- 2005-03-18 PT PT05733590T patent/PT1735330E/pt unknown
- 2005-03-18 PL PL05733590T patent/PL1735330T3/pl unknown
- 2005-03-18 KR KR1020067021801A patent/KR20070028355A/ko not_active Ceased
- 2005-03-18 UA UAA200609904A patent/UA88782C2/ru unknown
- 2005-03-18 AU AU2005225560A patent/AU2005225560B2/en not_active Ceased
- 2005-03-22 PE PE2005000328A patent/PE20060094A1/es not_active Application Discontinuation
- 2005-03-23 AR ARP050101145A patent/AR048330A1/es unknown
- 2005-03-24 MY MYPI20051276A patent/MY143074A/en unknown
2006
- 2006-09-11 IL IL178010A patent/IL178010A0/en unknown
- 2006-09-18 ZA ZA200607801A patent/ZA200607801B/en unknown
- 2006-09-25 EC EC2006006881A patent/ECSP066881A/es unknown
- 2006-10-24 NO NO20064822A patent/NO20064822L/no not_active Application Discontinuation
- 2006-10-24 LV LVP-06-120A patent/LV13527B/lv unknown
2008
- 2008-01-10 CY CY20081100031T patent/CY1107132T1/el unknown

Also Published As

Publication number	Publication date
BRPI0509153A (pt)	2007-11-20
UA88782C2 (en)	2009-11-25
US7691836B2 (en)	2010-04-06
CY1107132T1 (el)	2012-10-24
RU2381232C2 (ru)	2010-02-10
DK1735330T3 (da)	2008-03-31
SI1735330T1 (sl)	2008-04-30
DE602005003564T2 (de)	2008-10-23
NO20064822L (no)	2006-10-24
TW200531977A (en)	2005-10-01
EP1735330A1 (en)	2006-12-27
EP1735330B1 (en)	2007-11-28
IL178010A0 (en)	2006-12-31
KR20070028355A (ko)	2007-03-12
ES2297699T3 (es)	2008-05-01
DE602005003564D1 (de)	2008-01-10
MY143074A (en)	2011-02-28
CN100549023C (zh)	2009-10-14
AR048330A1 (es)	2006-04-19
ECSP066881A (es)	2006-11-24
ZA200607801B (en)	2008-07-30
PE20060094A1 (es)	2006-02-24
JP4922918B2 (ja)	2012-04-25
HK1096405A1 (en)	2007-06-01
AU2005225560B2 (en)	2011-01-27
RU2006137578A (ru)	2008-04-27
CA2560694A1 (en)	2005-10-06
CA2560694C (en)	2012-03-06
AU2005225560A1 (en)	2005-10-06
NZ549862A (en)	2010-01-29
JP2007530501A (ja)	2007-11-01
PL1735330T3 (pl)	2008-05-30
MXPA06010906A (es)	2007-03-08
WO2005092912A1 (en)	2005-10-06
PT1735330E (pt)	2007-12-21
CN1934125A (zh)	2007-03-21
US20070203105A1 (en)	2007-08-30

Publication	Publication Date	Title
JP2911553B2 (ja)	1999-06-23	１１β―アリール―４―エストレン、その製法、中間生成物及び新規化合物を含有する抗ゲスタゲン及び抗グルココルチコイド作用を有する製薬学的製済
JP6130087B1 (ja)	2017-05-17	１７−ヒドロキシ−１７−ペンタフルオロエチル−エストラ−４，９（１０）−ジエン−１１−アリール誘導体、その製造方法、その誘導体を利用した諸疾患の治療
AU736064B2 (en)	2001-07-26	16-hydroxy-11-(substituted phenyl)-estra-4,9-diene derivatives
JP5809172B2 (ja)	2015-11-10	プロゲステロン受容体アンタゴニスト
CN102596985B (zh)	2017-05-24	17‑羟基‑17‑五氟乙基‑雌‑4，9(10)‑二烯‑11‑芳基衍生物、其制备方法及其用于治疗疾病的用途
EP0559690B1 (de)	1997-06-04	8-EN-19, 11 beta-ÜBERBRÜCKTE STEROIDE, DEREN HERSTELLUNG UND DIESE ENTHALTENDE PHARMAZEUTISCHE PRÄPARATE
JPH04505324A (ja)	1992-09-17	９α―ヒドロキシ―１９，１１β―橋かけステロイド、その製造およびこれを含有する調剤学的調製剤
CA2560694C (en)	2012-03-06	Progesterone receptor modulators
DE4042007A1 (de)	1992-06-25	6,7-modifizierte-11(beta)-aryl-4-estrene
HK1096405B (en)	2008-02-06	Progesterone receptor modulators
JP2004505093A (ja)	2004-02-19	１６α−メチルまたはエチル置換エストロゲン
DE4417880A1 (de)	1995-11-23	19,11beta-Überbrückte 18-Nor-Steroide, Verfahren zu ihrer Herstellung, diese Steroide enthaltende Arzneimittel sowie deren Verwendung zur Herstellung von Arzneimitteln