DK135047B - Analogifremgangsmåde til fremstilling af 11,11-alkylidensteroider af estran- eller 19-norpregnanrækken. - Google Patents
Analogifremgangsmåde til fremstilling af 11,11-alkylidensteroider af estran- eller 19-norpregnanrækken.Info
- Publication number
- DK135047B DK135047B DK666473AA DK666473A DK135047B DK 135047 B DK135047 B DK 135047B DK 666473A A DK666473A A DK 666473AA DK 666473 A DK666473 A DK 666473A DK 135047 B DK135047 B DK 135047B
- Authority
- DK
- Denmark
- Prior art keywords
- norpregane
- estran
- series
- preparation
- analogous process
- Prior art date
Links
- GRXPVLPQNMUNNX-MHJRRCNVSA-N estrane Chemical compound C1CC2CCCC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 GRXPVLPQNMUNNX-MHJRRCNVSA-N 0.000 title 1
Classifications
-
- 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
- C07J5/0046—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 substituted in position 17 alfa
- C07J5/0053—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 substituted in position 17 alfa not substituted in position 16
-
- 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
- C07J1/0051—Estrane derivatives
- C07J1/0059—Estrane derivatives substituted in position 17 by a keto group
-
- 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
- C07J1/0051—Estrane derivatives
- C07J1/0081—Substituted in position 17 alfa and 17 beta
- C07J1/0085—Substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being a saturated hydrocarbon group
-
- 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
- C07J1/0051—Estrane derivatives
- C07J1/0081—Substituted in position 17 alfa and 17 beta
- C07J1/0088—Substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
- C07J1/0092—Alkenyl derivatives
-
- 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
- C07J1/0051—Estrane derivatives
- C07J1/0081—Substituted in position 17 alfa and 17 beta
- C07J1/0088—Substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
- C07J1/0096—Alkynyl derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J11/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/005—Ketals
- C07J21/008—Ketals at position 17
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J33/00—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J33/005—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton spiro-condensed
-
- 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
- C07J5/0007—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 not substituted in position 17 alfa
- C07J5/0023—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 not substituted in position 17 alfa substituted in position 16
- C07J5/003—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 not substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group including 16-alkylidene substitutes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
-
- 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
-
- 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
- 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
- C07J7/005—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 substituted in position 16
- C07J7/0055—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 substituted in position 16 by a saturated or unsaturated hydrocarbon group
-
- 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
- C07J7/008—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21
- C07J7/0095—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21 carbon in position 21 is part of carboxylic group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK293776A DK147405C (da) | 1972-12-09 | 1976-06-30 | 11,11-alkylidensteroider af estran- og 19-nor-pregnanraekken til brug som svangerskabsforebyggende midler |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL7216767A NL175063C (nl) | 1972-12-09 | 1972-12-09 | Werkwijze ter bereiding van 11,11-alkylideensteroiden, werkwijze ter bereiding van farmaceutische preparaten en gevormde farmaceutische preparaten. |
NL7315704A NL7315704A (en) | 1973-11-15 | 1973-11-15 | 11,11-Alkylidene steroids - of the oestrane, pregnane and 19-norpregnane series |
Publications (2)
Publication Number | Publication Date |
---|---|
DK135047B true DK135047B (da) | 1977-02-28 |
DK135047C DK135047C (ja) | 1977-07-25 |
Family
ID=26644839
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK666473AA DK135047B (da) | 1972-12-09 | 1973-12-07 | Analogifremgangsmåde til fremstilling af 11,11-alkylidensteroider af estran- eller 19-norpregnanrækken. |
DK293776A DK147405C (da) | 1972-12-09 | 1976-06-30 | 11,11-alkylidensteroider af estran- og 19-nor-pregnanraekken til brug som svangerskabsforebyggende midler |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK293776A DK147405C (da) | 1972-12-09 | 1976-06-30 | 11,11-alkylidensteroider af estran- og 19-nor-pregnanraekken til brug som svangerskabsforebyggende midler |
Country Status (14)
Country | Link |
---|---|
US (1) | US3927046A (ja) |
JP (1) | JPS5933600B2 (ja) |
CA (1) | CA1021318A (ja) |
CH (1) | CH614453A5 (ja) |
DE (1) | DE2361120C2 (ja) |
DK (2) | DK135047B (ja) |
ES (1) | ES421253A1 (ja) |
FI (1) | FI54128C (ja) |
FR (1) | FR2209577B1 (ja) |
GB (1) | GB1455270A (ja) |
IE (1) | IE38617B1 (ja) |
IL (1) | IL43762A (ja) |
PH (1) | PH11191A (ja) |
SE (1) | SE414771B (ja) |
Families Citing this family (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL188581C (nl) * | 1974-07-15 | 1992-08-03 | Akzo Nv | Werkwijze voor het bereiden van 11beta-hydroxy-18-alkylestraanverbindingen. |
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 |
FR2377419A1 (fr) * | 1977-01-13 | 1978-08-11 | Roussel Uclaf | Nouveaux derives steroides 11b-substitues 1,3,5 (10) trieniques, leur procede de preparation et leur application comme medicament |
NL7701384A (nl) * | 1977-02-10 | 1978-08-14 | Akzo Nv | Werkwijze voor het bereiden van nieuwe steroiden van de oestraanreeks. |
DE2913381A1 (de) * | 1979-03-30 | 1980-10-16 | Schering Ag | 11-methylensteroide, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
DE3042529A1 (de) * | 1980-11-07 | 1982-06-24 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 11-methylen- (delta)(pfeil hoch)1(pfeil hoch)(pfeil hoch)5(pfeil hoch) -steroide, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
AU572589B2 (en) * | 1983-12-14 | 1988-05-12 | Upjohn Company, The | 11(alpha)-difluoromethyl and (e)-and (z)-11-fluoromethylene steroids |
US4567000A (en) * | 1984-08-31 | 1986-01-28 | The Upjohn Company | 11-Difluoromethylene steroids |
JPS6161578U (ja) * | 1984-09-27 | 1986-04-25 | ||
IE58562B1 (en) * | 1985-07-24 | 1993-10-06 | Akzo Nv | Novel 11-methylene-oestr-15-enes, processes for their preparation, and pharmaceutical compositions |
US5236913A (en) * | 1985-07-24 | 1993-08-17 | Akzo N.V. | 11-methylene-oestr-15-enes, processes for their preparation, and pharmaceutical compositions |
US4662065A (en) * | 1986-05-22 | 1987-05-05 | Battery Engineering, Inc. | Method for dehydrating manganese dioxide |
CA2100514C (en) * | 1992-07-29 | 2005-03-29 | Johannes A. M. Hamersma | 17-spiromethylene steroids |
ZA94715B (en) * | 1993-02-08 | 1994-10-24 | Akzo Nv | Steroids for treating menopausal complaints |
DE4330727C2 (de) * | 1993-09-10 | 1998-02-19 | Jenapharm Gmbh | Steroidzwischenprodukte und Verfahren zu ihrer Herstellung |
DE4344462C2 (de) | 1993-12-22 | 1996-02-01 | Schering Ag | Zusammensetzung für die Empfängnisverhütung |
DE4413184A1 (de) * | 1994-04-12 | 1995-10-19 | Schering Ag | 10,11-C¶3¶-überbrückte Steroide |
DE19723390C1 (de) * | 1997-06-04 | 1998-06-10 | Jenapharm Gmbh | 9alpha-Hydroxy-8alpha-estra-1,3,5(10)-triene und Verfahren zu deren Herstellung |
US5952319A (en) * | 1997-11-26 | 1999-09-14 | Research Triangle Institute | Androgenic steroid compounds and a method of making and using the same |
US6054446A (en) * | 1997-12-24 | 2000-04-25 | Sri International | Anti-estrogenic steroids, and associated pharmaceutical compositions and methods of use |
CA2435350A1 (en) * | 2001-02-02 | 2002-08-15 | Pharmacia Corporation | Method of using a cyclooxygenase-2 inhibitor and sex steroids as a combination therapy for the treatment and prevention of dismenorrhea |
CN1649614A (zh) | 2002-02-22 | 2005-08-03 | 新河药品股份有限公司 | 活性剂传递系统和保护及施用活性剂的方法 |
ITMI20021755A1 (it) * | 2002-08-02 | 2002-11-01 | Poli Ind Chimica Spa | Processo e nuovi intermedi per la preparazione di steroidi ad attivita' progestinica. |
HUP0301332A3 (en) * | 2003-05-14 | 2006-04-28 | Richter Gedeon Vegyeszet | New mono-and bismethylene steroid derivatives and process for their synthesis and pharmaceutical compositions containing them |
CN101445542B (zh) * | 2008-12-25 | 2010-12-29 | 北京市科益丰生物技术发展有限公司 | 一种去氧孕烯的制备方法 |
CN101857624B (zh) * | 2010-06-25 | 2012-12-12 | 北京紫竹药业有限公司 | 去氧孕烯的制备工艺及其中间体化合物 |
CN102964418B (zh) * | 2010-06-25 | 2015-04-15 | 华润紫竹药业有限公司 | 去氧孕烯的制备工艺及其中间体化合物 |
CN102532232A (zh) * | 2010-12-27 | 2012-07-04 | 上海信谊药厂有限公司 | 去氧孕烯的制备方法 |
US20130123523A1 (en) * | 2011-11-10 | 2013-05-16 | Klaus Nickisch | Methods for the preparation of etonogestrel and desogestrel |
CN107955052B (zh) | 2011-12-23 | 2024-07-05 | 晶体制药独资有限公司 | 炔基化16-取代-17-酮基类固醇的方法 |
US9464108B2 (en) | 2012-03-15 | 2016-10-11 | Merck Sharp & Dohme B.V. | Combined synthesis route for desogestrel and etonogestrel |
ITMI20121472A1 (it) * | 2012-09-04 | 2014-03-05 | Ind Chimica Srl | Processo per la preparazione di 11-metilen-18-metilestr-4-en-3,17-dione, utile come intermedio per la sintesi di molecole ad attivita' farmacologica |
ES2881336T3 (es) * | 2016-03-03 | 2021-11-29 | Crystal Pharma Sau | Procedimiento y nuevos productos intermedios para la preparación de 11-metilen-esteroides |
CN107082793B (zh) * | 2017-06-16 | 2019-07-05 | 上海共拓医药化工有限公司 | 去氧孕烯重要中间体的制备方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB912036A (en) * | 1960-06-23 | 1962-12-05 | British Drug Houses Ltd | 11-methylene-5ª--steroids |
US3325520A (en) * | 1965-12-08 | 1967-06-13 | Searle & Co | (optionally 17-hydrocarbon-substituted) 11, 13beta-dialkylgon-4-en-3-ones and esters corresponding |
US3299108A (en) * | 1965-10-18 | 1967-01-17 | Searle & Co | 17alpha-alkynyl/alkenyl-13beta-alkyl-11-alkylgona-1, 3, 5 (10)-triene-3, 17beta-diols, ethers and esters thereof and intermediates thereto |
US3346602A (en) * | 1966-10-12 | 1967-10-10 | Searle & Co | 13beta-alkyl-11-alkylgona-1, 3, 5 (10)-trien-17-ones, ethers and esters thereof |
US3527778A (en) * | 1969-02-27 | 1970-09-08 | Searle & Co | 3,17 - bisoxygenated 11betamethyl - 19 - norpregn - 4 - en - 20 - ones and derivatives thereof |
-
1973
- 1973-12-03 FI FI3704/73A patent/FI54128C/fi active
- 1973-12-03 US US420823A patent/US3927046A/en not_active Expired - Lifetime
- 1973-12-04 CA CA187,327A patent/CA1021318A/en not_active Expired
- 1973-12-04 GB GB5608373A patent/GB1455270A/en not_active Expired
- 1973-12-05 IL IL43762A patent/IL43762A/xx unknown
- 1973-12-06 PH PH15304A patent/PH11191A/en unknown
- 1973-12-07 CH CH1719873A patent/CH614453A5/xx active Protection Beyond IP Right Term
- 1973-12-07 FR FR7343845A patent/FR2209577B1/fr not_active Expired
- 1973-12-07 SE SE7316562A patent/SE414771B/xx active Protection Beyond IP Right Term
- 1973-12-07 ES ES421253A patent/ES421253A1/es not_active Expired
- 1973-12-07 IE IE2219/73A patent/IE38617B1/xx unknown
- 1973-12-07 DK DK666473AA patent/DK135047B/da not_active IP Right Cessation
- 1973-12-07 DE DE2361120A patent/DE2361120C2/de not_active Expired
- 1973-12-08 JP JP48137287A patent/JPS5933600B2/ja not_active Expired
-
1976
- 1976-06-30 DK DK293776A patent/DK147405C/da not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
IL43762A (en) | 1978-04-30 |
ES421253A1 (es) | 1976-07-16 |
JPS5933600B2 (ja) | 1984-08-16 |
AU6326373A (en) | 1975-06-05 |
IE38617L (en) | 1974-06-09 |
DE2361120C2 (de) | 1984-01-19 |
DK147405B (da) | 1984-07-23 |
DK147405C (da) | 1985-02-04 |
GB1455270A (en) | 1976-11-10 |
CH614453A5 (ja) | 1979-11-30 |
DK293776A (da) | 1976-06-30 |
CA1021318A (en) | 1977-11-22 |
FI54128C (fi) | 1978-10-10 |
US3927046A (en) | 1975-12-16 |
IL43762A0 (en) | 1974-03-14 |
FR2209577A1 (ja) | 1974-07-05 |
FI54128B (fi) | 1978-06-30 |
JPS5029548A (ja) | 1975-03-25 |
IE38617B1 (en) | 1978-04-26 |
PH11191A (en) | 1977-10-28 |
SE414771B (sv) | 1980-08-18 |
FR2209577B1 (ja) | 1977-06-03 |
DE2361120A1 (de) | 1974-06-12 |
DK135047C (ja) | 1977-07-25 |
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