MXPA06011696A - Derivados de tioamida como moduladores del receptor de progesterona. - Google Patents
Derivados de tioamida como moduladores del receptor de progesterona.Info
- Publication number
- MXPA06011696A MXPA06011696A MXPA06011696A MXPA06011696A MXPA06011696A MX PA06011696 A MXPA06011696 A MX PA06011696A MX PA06011696 A MXPA06011696 A MX PA06011696A MX PA06011696 A MXPA06011696 A MX PA06011696A MX PA06011696 A MXPA06011696 A MX PA06011696A
- Authority
- MX
- Mexico
- Prior art keywords
- compound
- formula
- further characterized
- substituted
- alkyl
- Prior art date
Links
- 150000003556 thioamides Chemical class 0.000 title abstract description 10
- 239000002379 progesterone receptor modulator Substances 0.000 title abstract description 3
- 229940095745 sex hormone and modulator of the genital system progesterone receptor modulator Drugs 0.000 title abstract description 3
- -1 and specifically Chemical class 0.000 claims abstract description 25
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound 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 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims description 99
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 28
- 229910052717 sulfur Inorganic materials 0.000 claims description 28
- 206010000496 acne Diseases 0.000 claims description 23
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- 239000011593 sulfur Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
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- 125000004103 aminoalkyl group Chemical group 0.000 claims description 10
- 230000001419 dependent effect Effects 0.000 claims description 10
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical group COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 9
- 201000009273 Endometriosis Diseases 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
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- 239000000583 progesterone congener Substances 0.000 claims description 8
- IRDLUHRVLVEUHA-UHFFFAOYSA-N diethyl dithiophosphate Chemical group CCOP(S)(=S)OCC IRDLUHRVLVEUHA-UHFFFAOYSA-N 0.000 claims description 7
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- 229910052736 halogen Inorganic materials 0.000 claims description 7
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- 150000003233 pyrroles Chemical class 0.000 claims 1
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- 102000002260 Alkaline Phosphatase Human genes 0.000 description 4
- 108020004774 Alkaline Phosphatase Proteins 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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Landscapes
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- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Diabetes (AREA)
- Dermatology (AREA)
- Gynecology & Obstetrics (AREA)
- Oncology (AREA)
- Urology & Nephrology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Ink Jet (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56056904P | 2004-04-08 | 2004-04-08 | |
| PCT/US2005/011757 WO2005100346A1 (en) | 2004-04-08 | 2005-04-07 | Thioamide derivatives as progesterone receptor modulators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA06011696A true MXPA06011696A (es) | 2006-12-14 |
Family
ID=34965700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA06011696A MXPA06011696A (es) | 2004-04-08 | 2005-04-07 | Derivados de tioamida como moduladores del receptor de progesterona. |
Country Status (14)
| Country | Link |
|---|---|
| US (4) | US7358246B2 (https=) |
| EP (1) | EP1732921B1 (https=) |
| JP (1) | JP4869221B2 (https=) |
| CN (1) | CN100522960C (https=) |
| AT (1) | ATE413398T1 (https=) |
| AU (1) | AU2005233591B2 (https=) |
| BR (1) | BRPI0509209A (https=) |
| CA (1) | CA2561014C (https=) |
| DE (1) | DE602005010840D1 (https=) |
| DK (1) | DK1732921T3 (https=) |
| ES (1) | ES2317223T3 (https=) |
| MX (1) | MXPA06011696A (https=) |
| PL (1) | PL1732921T3 (https=) |
| WO (1) | WO2005100346A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2317223T3 (es) * | 2004-04-08 | 2009-04-16 | Wyeth | Derivados de tioamida como moduladores del receptor de progesterona. |
| JP4950027B2 (ja) * | 2004-04-08 | 2012-06-13 | ワイス・エルエルシー | チオアミド不純物を最小限に抑えるための方法 |
| GT200500185A (es) * | 2004-08-09 | 2006-04-10 | Moduladores del receptor de progesterona que comprenden derivados de pirrol-oxindol y sus usos | |
| US20070093548A1 (en) * | 2005-10-25 | 2007-04-26 | Wyeth | Use of progesterone receptor modulators |
| US7618989B2 (en) * | 2006-08-15 | 2009-11-17 | Wyeth | Tricyclic oxazolidone derivatives useful as PR modulators |
| BRPI0819571A2 (pt) * | 2007-12-20 | 2019-09-24 | Teva Womenss Health Inc | "método para contracepção de emergência, pacote farmacêutico para contracepção de emergência e composição farmacêutica" |
| CN107281215A (zh) * | 2016-04-01 | 2017-10-24 | 复旦大学附属妇产科医院 | 硫化氢供体硫氢化钠在制药中的用途 |
Family Cites Families (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3536809A (en) | 1969-02-17 | 1970-10-27 | Alza Corp | Medication method |
| US3598123A (en) | 1969-04-01 | 1971-08-10 | Alza Corp | Bandage for administering drugs |
| US3845770A (en) | 1972-06-05 | 1974-11-05 | Alza Corp | Osmatic dispensing device for releasing beneficial agent |
| US3916899A (en) | 1973-04-25 | 1975-11-04 | Alza Corp | Osmotic dispensing device with maximum and minimum sizes for the passageway |
| US4008719A (en) | 1976-02-02 | 1977-02-22 | Alza Corporation | Osmotic system having laminar arrangement for programming delivery of active agent |
| US4295987A (en) | 1979-12-26 | 1981-10-20 | The Procter & Gamble Company | Cross-linked sodium polyacrylate absorbent |
| US4959217A (en) | 1986-05-22 | 1990-09-25 | Syntex (U.S.A.) Inc. | Delayed/sustained release of macromolecules |
| AU608891B2 (en) | 1987-09-24 | 1991-04-18 | Merck & Co., Inc. | Solubility modulated drug delivery device |
| US5273752A (en) | 1989-07-18 | 1993-12-28 | Alza Corporation | Controlled release dispenser comprising beneficial agent |
| US5124455A (en) | 1990-08-08 | 1992-06-23 | American Home Products Corporation | Oxime-carbamates and oxime-carbonates as bronchodilators and anti-inflammatory agents |
| US5459151A (en) | 1993-04-30 | 1995-10-17 | American Home Products Corporation | N-acyl substituted phenyl piperidines as bronchodilators and antiinflammatory agents |
| US5854388A (en) | 1993-06-24 | 1998-12-29 | Washington State University Research Foundation | Angiotensin IV peptides and receptor |
| US5817343A (en) | 1996-05-14 | 1998-10-06 | Alkermes, Inc. | Method for fabricating polymer-based controlled-release devices |
| US5756127A (en) | 1996-10-29 | 1998-05-26 | Wright Medical Technology, Inc. | Implantable bioresorbable string of calcium sulfate beads |
| FI971385A0 (fi) | 1997-04-04 | 1997-04-04 | Bioxid Oy | Biokompatibel komposition, metoder foer dess framstaellning samt anvaendning daerav |
| US6355648B1 (en) | 1999-05-04 | 2002-03-12 | American Home Products Corporation | Thio-oxindole derivatives |
| SG120970A1 (en) * | 1999-05-04 | 2006-04-26 | Ligand Pharm Inc | Cyclothiocarbamate derivatives as progesterone receptor modulators |
| JP2002543182A (ja) * | 1999-05-04 | 2002-12-17 | ワイス | チオオキシインドール誘導体 |
| US6417214B1 (en) | 1999-05-04 | 2002-07-09 | Wyeth | 3,3-substituted indoline derivatives |
| US6509334B1 (en) | 1999-05-04 | 2003-01-21 | American Home Products Corporation | Cyclocarbamate derivatives as progesterone receptor modulators |
| US6391907B1 (en) | 1999-05-04 | 2002-05-21 | American Home Products Corporation | Indoline derivatives |
| US6407101B1 (en) * | 1999-05-04 | 2002-06-18 | American Home Products Corporation | Cyanopyrroles |
| CO5190716A1 (es) | 1999-08-10 | 2002-08-29 | Smithkline Beecham Corp | 4,4-diaril-ciclohexanos 1,4-sustituidos |
| US6258833B1 (en) | 1999-12-23 | 2001-07-10 | Icos Corporation | Cyclic AMP-specific phosphodiesterase inhibitors |
| UA73119C2 (en) * | 2000-04-19 | 2005-06-15 | American Home Products Corpoir | Derivatives of cyclic thiocarbamates, pharmaceutical composition including noted derivatives of cyclic thiocarbamates and active ingredients of medicines as modulators of progesterone receptors |
| JP4716547B2 (ja) * | 2000-08-10 | 2011-07-06 | 住友精化株式会社 | ２−フェニルチアゾール類の製造方法 |
| US20030225273A1 (en) * | 2002-03-21 | 2003-12-04 | Michaelides Michael R. | Thiopyrimidine and isothiazolopyrimidine kinase inhibitors |
| MXPA04012226A (es) * | 2002-06-06 | 2005-04-08 | Eisai Co Ltd | Nuevos derivados de imidazola. |
| US7115649B2 (en) * | 2002-06-25 | 2006-10-03 | Wyeth | Methods of treating skin disorders using thio-oxindole derivatives |
| JP2005535628A (ja) | 2002-06-25 | 2005-11-24 | ワイス | Ｐｒモジュレーターとしてのシクロチオカルバメート誘導体 |
| IL165395A0 (en) * | 2002-06-25 | 2006-01-15 | Wyeth Corp | Use of thio-oxubdile derivatives in treatment of hormone-related conditions |
| CN1662241A (zh) | 2002-06-25 | 2005-08-31 | 惠氏公司 | 环硫代氨基甲酸酯衍生物在治疗与激素有关的病症中的用途 |
| ES2317223T3 (es) | 2004-04-08 | 2009-04-16 | Wyeth | Derivados de tioamida como moduladores del receptor de progesterona. |
| JP4950027B2 (ja) * | 2004-04-08 | 2012-06-13 | ワイス・エルエルシー | チオアミド不純物を最小限に抑えるための方法 |
| BRPI0509159B1 (pt) * | 2004-04-08 | 2014-08-26 | Wyeth Llc | Processo para preparar um composto de fenoxicicloalquila |
| MXPA06012403A (es) * | 2004-04-27 | 2007-01-17 | Wyeth Corp | Purificacion de moduladores de receptor progesterona. |
-
2005
- 2005-04-07 ES ES05735464T patent/ES2317223T3/es not_active Expired - Lifetime
- 2005-04-07 MX MXPA06011696A patent/MXPA06011696A/es active IP Right Grant
- 2005-04-07 AU AU2005233591A patent/AU2005233591B2/en not_active Ceased
- 2005-04-07 WO PCT/US2005/011757 patent/WO2005100346A1/en not_active Ceased
- 2005-04-07 BR BRPI0509209-4A patent/BRPI0509209A/pt not_active IP Right Cessation
- 2005-04-07 PL PL05735464T patent/PL1732921T3/pl unknown
- 2005-04-07 JP JP2007507494A patent/JP4869221B2/ja not_active Expired - Fee Related
- 2005-04-07 DE DE602005010840T patent/DE602005010840D1/de not_active Expired - Lifetime
- 2005-04-07 DK DK05735464T patent/DK1732921T3/da active
- 2005-04-07 AT AT05735464T patent/ATE413398T1/de not_active IP Right Cessation
- 2005-04-07 US US11/100,860 patent/US7358246B2/en not_active Expired - Fee Related
- 2005-04-07 CN CNB2005800108301A patent/CN100522960C/zh not_active Expired - Fee Related
- 2005-04-07 CA CA2561014A patent/CA2561014C/en not_active Expired - Fee Related
- 2005-04-07 EP EP05735464A patent/EP1732921B1/en not_active Expired - Lifetime
-
2008
- 2008-03-07 US US12/044,287 patent/US7511071B2/en not_active Expired - Fee Related
-
2009
- 2009-02-12 US US12/369,789 patent/US7659265B2/en not_active Expired - Fee Related
-
2010
- 2010-02-02 US US12/698,472 patent/US8168672B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20090143345A1 (en) | 2009-06-04 |
| US7511071B2 (en) | 2009-03-31 |
| US20100197645A1 (en) | 2010-08-05 |
| CN100522960C (zh) | 2009-08-05 |
| CA2561014A1 (en) | 2005-10-27 |
| BRPI0509209A (pt) | 2007-08-28 |
| US20050227971A1 (en) | 2005-10-13 |
| EP1732921A1 (en) | 2006-12-20 |
| JP2007532564A (ja) | 2007-11-15 |
| DE602005010840D1 (de) | 2008-12-18 |
| WO2005100346A1 (en) | 2005-10-27 |
| CA2561014C (en) | 2013-09-10 |
| AU2005233591B2 (en) | 2011-10-27 |
| AU2005233591A1 (en) | 2005-10-27 |
| US7358246B2 (en) | 2008-04-15 |
| US8168672B2 (en) | 2012-05-01 |
| CN1938299A (zh) | 2007-03-28 |
| EP1732921B1 (en) | 2008-11-05 |
| ATE413398T1 (de) | 2008-11-15 |
| JP4869221B2 (ja) | 2012-02-08 |
| US20080167299A1 (en) | 2008-07-10 |
| PL1732921T3 (pl) | 2009-04-30 |
| US7659265B2 (en) | 2010-02-09 |
| DK1732921T3 (da) | 2009-02-23 |
| ES2317223T3 (es) | 2009-04-16 |
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