HUP9801059A2 - C25-Helyettesített D-vitamin-származékok, eljárás előállításukra, köztitermékeik és alkalmazásuk gyógyszerek előállítására - Google Patents
C25-Helyettesített D-vitamin-származékok, eljárás előállításukra, köztitermékeik és alkalmazásuk gyógyszerek előállításáraInfo
- Publication number
- HUP9801059A2 HUP9801059A2 HU9801059A HUP9801059A HUP9801059A2 HU P9801059 A2 HUP9801059 A2 HU P9801059A2 HU 9801059 A HU9801059 A HU 9801059A HU P9801059 A HUP9801059 A HU P9801059A HU P9801059 A2 HUP9801059 A2 HU P9801059A2
- Authority
- HU
- Hungary
- Prior art keywords
- atom
- hydrogen
- vitamin
- ring
- derivatives
- Prior art date
Links
- 150000003710 vitamin D derivatives Chemical class 0.000 title abstract 3
- 239000003814 drug Substances 0.000 title 1
- 239000013067 intermediate product Substances 0.000 title 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- 150000001721 carbon Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 239000000843 powder Substances 0.000 abstract 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- XNOPRXBHLZRZKH-UHFFFAOYSA-N Oxytocin Natural products N1C(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CC(C)C)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C(C(C)CC)NC(=O)C1CC1=CC=C(O)C=C1 XNOPRXBHLZRZKH-UHFFFAOYSA-N 0.000 abstract 1
- 101800000989 Oxytocin Proteins 0.000 abstract 1
- 102100031951 Oxytocin-neurophysin 1 Human genes 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000005333 aroyloxy group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 239000008280 blood Substances 0.000 abstract 1
- 210000004369 blood Anatomy 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 239000011737 fluorine Chemical group 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- -1 hydroxymethylene ring Chemical group 0.000 abstract 1
- 239000002207 metabolite Substances 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- XNOPRXBHLZRZKH-DSZYJQQASA-N oxytocin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 abstract 1
- 229960001723 oxytocin Drugs 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C401/00—Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation
-
- 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
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- 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
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- 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
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Neurology (AREA)
- Heart & Thoracic Surgery (AREA)
- Immunology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Vascular Medicine (AREA)
- Nutrition Science (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
A találmány tárgyát az (I) általánős képletű C25 helyettesített D-vitamin-származékők képezik. A képletben Y1 hidrőgénatőm, hidrőxi-,alkanőil-őxi- vagy arőil-őxi-csőpőrt; Y2 hidrőgénatőm, alkanőil- vagyarőilcsőpőrt; R1 és R2 hidrőgénatőm vagy együtt metiléncsőpőrt; R3 ésR4 hidrőgén-, klór- vagy flűőratőm, alkilcsőpőrt, együttmetiléncsőpőrt vagy a 20-as szénatőmmal együtt karbőciklűsős csőpőrt;A és B együtt őxőcsőpőrt vagy az egyik hidrőgénatőm és a másik -OR'csőpőrt; R5 és R6 hidrőgén-, klór- vagy flűőratőm, triflűőr-metil-vagy szénhidrőgén-csőpőrt vagy a 25-ös szénatőmmal együttkarbőciklűsős gyűrűt képeznek; és Z szénhidrőgéncsőpőrt, adőtt esetbenkarbő- vagy heterőciklűsős szerkezettel, és tetszőleges helyekenszűbsztitűensekkel, és a 25-ös szénatőmhőz karbőnil- vagy hidrőxi-metilén-csőpőrtőn vagy eténdiil-egységen keresztül kapcsőlódik. Atalálmány szerinti D-vitamin-származékők aktív metabőlitjai aszérűmban a kalciűm- és főszfát-kőncentrációt szabályőzzák. ŕ
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19522797 | 1995-06-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUP9801059A2 true HUP9801059A2 (hu) | 1998-08-28 |
| HUP9801059A3 HUP9801059A3 (en) | 1999-05-28 |
Family
ID=7765061
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9801059A HUP9801059A3 (en) | 1995-06-14 | 1996-04-30 | Vitamin d derivatives with c-25 substituents, process for their preparation, intermediate products and their use in preparing medicaments |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US6372731B1 (hu) |
| EP (1) | EP0832063B1 (hu) |
| JP (1) | JPH11507649A (hu) |
| AT (1) | ATE189888T1 (hu) |
| AU (1) | AU707942B2 (hu) |
| CA (1) | CA2224440A1 (hu) |
| CZ (1) | CZ291915B6 (hu) |
| DE (1) | DE59604498D1 (hu) |
| DK (1) | DK0832063T3 (hu) |
| ES (1) | ES2144239T3 (hu) |
| GR (1) | GR3033459T3 (hu) |
| HU (1) | HUP9801059A3 (hu) |
| IL (1) | IL118366A (hu) |
| NO (1) | NO317059B1 (hu) |
| NZ (1) | NZ307549A (hu) |
| PT (1) | PT832063E (hu) |
| TW (1) | TW351714B (hu) |
| WO (1) | WO1997000242A1 (hu) |
| ZA (1) | ZA965098B (hu) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5795882A (en) * | 1992-06-22 | 1998-08-18 | Bone Care International, Inc. | Method of treating prostatic diseases using delayed and/or sustained release vitamin D formulations |
| DE19619036A1 (de) | 1996-04-30 | 1997-11-13 | Schering Ag | Neue Vitamin D-Derivate mit carbo- oder heterocyclischen Substituenten an C-25, Verfahren zu ihrer Herstellung und die Verwendung zur Herstellung von Arzneimitteln |
| US6392071B1 (en) * | 1997-03-17 | 2002-05-21 | Wisconsin Alumni: Research Foundation | 26,27-homologated-20-EPI-2-alkylidene-19-nor-vitamin D compounds |
| DE69814109T2 (de) * | 1997-09-08 | 2004-02-26 | F. Hoffmann-La Roche Ag | 1,3-dihydroxy-20,20-dialkyl-vitamin d3 analoga |
| DE19744127B4 (de) | 1997-10-01 | 2006-10-05 | Schering Ag | Neue Vitamin D-Derivate mit Cyclopropylringen in den Seitenketten, Verfahren und Zwischenprodukte zu ihrer Herstellung sowie ihre Verwendung zur Herstellung von Arzneimitteln |
| EP0927721A1 (de) * | 1997-12-17 | 1999-07-07 | Schering Aktiengesellschaft | Neue Vitamin D-Derivate mit Phosphoratomen in den Seitenketten, Zwischenprodukte bei ihrer Herstellung und die Verwendung zur Herstellung von Arzneimitteln |
| WO1999031112A1 (de) * | 1997-12-17 | 1999-06-24 | Schering Aktiengesellschaft | Vitamin d-derivate mit phosphoratomen in den seitenketten |
| US5972917A (en) * | 1998-05-29 | 1999-10-26 | Bone Care Int Inc | 1 α-hydroxy-25-ene-vitamin D, analogs and uses thereof |
| US20040019024A1 (en) * | 2000-08-23 | 2004-01-29 | Seiichi Ishizuka | Use of vitamin d derivatives as bone resorption inhibitors |
| US7491711B2 (en) * | 2001-09-21 | 2009-02-17 | Roche Palo Alto Llc | Methods of treatment using 3-desoxy vitamin D3 analogs |
| DE10156596A1 (de) * | 2001-11-13 | 2003-05-28 | Schering Ag | Vitamin D-Derivate mit Acyloxygruppen in der Seitenkette, Verfahren zu ihrer Herstellung und die Verwendung zur Herstellung von Arzneimitteln |
| EP1458678A1 (en) * | 2002-11-18 | 2004-09-22 | Teva Pharmaceutical Industries Limited | A crystallization method for purification of calcipotriene |
| US7915242B2 (en) * | 2004-02-17 | 2011-03-29 | Wisconsin Alumni Research Foundation | Vitamin D receptor antagonists and their use in treating asthma |
| BRPI0606168A2 (pt) * | 2005-10-05 | 2009-06-02 | Sicor Inc | separação de isÈmeros de fulvestrant |
| BRPI0715636A2 (pt) * | 2006-08-29 | 2013-07-02 | Teva Pharma | composiÇÕes farmacologicamente ativas estÁveis incluindo compostos contendo vitamina d e corticosteràide com compatibilidade para ph baixo |
| WO2009108388A2 (en) * | 2008-02-28 | 2009-09-03 | University Of Tennessee Research Foundation | Enzymatic production or chemical synthesis and uses for 5,7-dienes and uvb conversion products thereof |
| US20110207944A1 (en) | 2008-11-04 | 2011-08-25 | Teijin Pharma Limited | Vitamin d3 lactam derivative |
| KR101991692B1 (ko) | 2009-01-27 | 2019-06-21 | 베르그 엘엘씨 | 화학요법과 연관된 부작용을 경감시키기 위한 비타민 ｄ３ 및 이의 유사물 |
| EA201270226A1 (ru) | 2009-08-14 | 2012-09-28 | БЕРГ БАЙОСИСТЕМЗ, ЭлЭлСи | Витамин d3 и его аналогии для лечения алопеции |
| AU2012262174B2 (en) * | 2011-06-03 | 2016-12-01 | Wisconsin Alumni Research Foundation | (22E)-2-methylene-26,27-cyclo-22-dehydro-1alpha-hydroxy-19-norvitamin D3 derivatives |
| US10479764B2 (en) | 2011-06-28 | 2019-11-19 | Wisconsin Alumni Research Foundation | 2-methylene-(22E)-25-hexanoyl-24-oxo-26,27-cyclo-22-dehydro-19-nor-vitamin D analogs |
| EP3003497B1 (en) | 2013-05-29 | 2024-02-14 | BPGbio, Inc. | Preventing or mitigating chemotherapy induced alopecia using vitamin d |
| WO2022078877A1 (en) * | 2020-10-12 | 2022-04-21 | Universite De Strasbourg | A calcium normalizer targeting the vitamin d receptor and therapeutic uses thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5182396A (en) * | 1991-03-29 | 1993-01-26 | Nisshin Flour Milling Co., Ltd. | 1-hydroxyvitamin d derivatives |
| IL107185A (en) * | 1992-10-06 | 1998-02-22 | Schering Ag | History of 52-carboxylic acid, processes for their preparation and pharmaceutical preparations containing them |
-
1996
- 1996-04-30 DE DE59604498T patent/DE59604498D1/de not_active Expired - Fee Related
- 1996-04-30 EP EP96915001A patent/EP0832063B1/de not_active Expired - Lifetime
- 1996-04-30 US US08/981,819 patent/US6372731B1/en not_active Expired - Fee Related
- 1996-04-30 NZ NZ307549A patent/NZ307549A/xx unknown
- 1996-04-30 AU AU56930/96A patent/AU707942B2/en not_active Ceased
- 1996-04-30 JP JP9502535A patent/JPH11507649A/ja not_active Ceased
- 1996-04-30 HU HU9801059A patent/HUP9801059A3/hu unknown
- 1996-04-30 DK DK96915001T patent/DK0832063T3/da active
- 1996-04-30 AT AT96915001T patent/ATE189888T1/de not_active IP Right Cessation
- 1996-04-30 ES ES96915001T patent/ES2144239T3/es not_active Expired - Lifetime
- 1996-04-30 WO PCT/EP1996/001788 patent/WO1997000242A1/de active IP Right Grant
- 1996-04-30 CZ CZ19974031A patent/CZ291915B6/cs not_active IP Right Cessation
- 1996-04-30 PT PT96915001T patent/PT832063E/pt unknown
- 1996-04-30 CA CA002224440A patent/CA2224440A1/en not_active Abandoned
- 1996-05-22 IL IL11836696A patent/IL118366A/en not_active IP Right Cessation
- 1996-05-23 TW TW085106144A patent/TW351714B/zh active
- 1996-06-14 ZA ZA965098A patent/ZA965098B/xx unknown
-
1997
- 1997-12-12 NO NO19975852A patent/NO317059B1/no unknown
-
2000
- 2000-05-19 GR GR20000401148T patent/GR3033459T3/el not_active IP Right Cessation
- 2000-12-18 US US09/738,286 patent/US6376480B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0832063B1 (de) | 2000-02-23 |
| ATE189888T1 (de) | 2000-03-15 |
| US6372731B1 (en) | 2002-04-16 |
| NO975852L (no) | 1998-02-16 |
| DE59604498D1 (de) | 2000-03-30 |
| NO975852D0 (no) | 1997-12-12 |
| GR3033459T3 (en) | 2000-09-29 |
| IL118366A (en) | 2004-12-15 |
| IL118366A0 (en) | 1996-09-12 |
| CZ403197A3 (cs) | 1998-07-15 |
| ES2144239T3 (es) | 2000-06-01 |
| PT832063E (pt) | 2000-06-30 |
| NO317059B1 (no) | 2004-08-02 |
| AU707942B2 (en) | 1999-07-22 |
| CZ291915B6 (cs) | 2003-06-18 |
| DK0832063T3 (da) | 2000-06-13 |
| EP0832063A1 (de) | 1998-04-01 |
| CA2224440A1 (en) | 1997-01-03 |
| HUP9801059A3 (en) | 1999-05-28 |
| NZ307549A (en) | 1999-11-29 |
| AU5693096A (en) | 1997-01-15 |
| US6376480B1 (en) | 2002-04-23 |
| TW351714B (en) | 1999-02-01 |
| WO1997000242A1 (de) | 1997-01-03 |
| JPH11507649A (ja) | 1999-07-06 |
| ZA965098B (en) | 1997-01-22 |
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