HRP20180032T1 - Postupak dobivanja spoja 4,4,7-trifluor-1,2,3,4-tetrahidro-5h-1-benzazepina i međuprodukta u njegovoj sintezi - Google Patents
Postupak dobivanja spoja 4,4,7-trifluor-1,2,3,4-tetrahidro-5h-1-benzazepina i međuprodukta u njegovoj sintezi Download PDFInfo
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- HRP20180032T1 HRP20180032T1 HRP20180032TT HRP20180032T HRP20180032T1 HR P20180032 T1 HRP20180032 T1 HR P20180032T1 HR P20180032T T HRP20180032T T HR P20180032TT HR P20180032 T HRP20180032 T HR P20180032T HR P20180032 T1 HRP20180032 T1 HR P20180032T1
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- Prior art keywords
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- -1 4,4,7-trifluoro-1,2,3,4-tetrahydro-5h-1-benzazepine compound Chemical class 0.000 title claims 5
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 81
- 238000000034 method Methods 0.000 claims 34
- 238000006243 chemical reaction Methods 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- WKXZJCKWUCBECD-GSVOUGTGSA-N (2r)-2-fluoropropan-1-ol Chemical compound C[C@@H](F)CO WKXZJCKWUCBECD-GSVOUGTGSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- STJVIACOQKGCFT-HJPCULJESA-N (2z)-2-[4,4,7-trifluoro-1-[4-[(2r)-2-fluoropropoxy]-2-(trifluoromethyl)benzoyl]-2,3-dihydro-1-benzazepin-5-ylidene]acetyl chloride Chemical compound FC(F)(F)C1=CC(OC[C@H](F)C)=CC=C1C(=O)N1C2=CC=C(F)C=C2C(=C/C(Cl)=O)/C(F)(F)CC1 STJVIACOQKGCFT-HJPCULJESA-N 0.000 claims 1
- GAECKYOCLRPJDL-UHFFFAOYSA-N 2-diphenoxyphosphorylacetic acid Chemical compound C=1C=CC=CC=1OP(=O)(CC(=O)O)OC1=CC=CC=C1 GAECKYOCLRPJDL-UHFFFAOYSA-N 0.000 claims 1
- QDSFNOHWQKVVEB-UHFFFAOYSA-N 4-(diethoxyphosphorylmethyl)morpholine Chemical compound CCOP(=O)(OCC)CN1CCOCC1 QDSFNOHWQKVVEB-UHFFFAOYSA-N 0.000 claims 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 claims 1
- 238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 claims 1
- AIHIHVZYAAMDPM-QMMMGPOBSA-N [(2s)-oxiran-2-yl]methyl 3-nitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC=CC(S(=O)(=O)OC[C@H]2OC2)=C1 AIHIHVZYAAMDPM-QMMMGPOBSA-N 0.000 claims 1
- 230000009435 amidation Effects 0.000 claims 1
- 238000007112 amidation reaction Methods 0.000 claims 1
- 239000012043 crude product Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- ZZUYIRISBMWFMV-UHFFFAOYSA-N methyl 4-chlorobutanoate Chemical compound COC(=O)CCCCl ZZUYIRISBMWFMV-UHFFFAOYSA-N 0.000 claims 1
- CYDAUDUZANFWIV-UHFFFAOYSA-N methyl 5-fluoro-2-[(4-methoxy-4-oxobutyl)-(4-methylphenyl)sulfonylamino]benzoate Chemical group C=1C=C(C)C=CC=1S(=O)(=O)N(CCCC(=O)OC)C1=CC=C(F)C=C1C(=O)OC CYDAUDUZANFWIV-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Urology & Nephrology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (15)
1. Postupak dobivanja spoja formule (1) prikazan u reakcijskoj shemi niže, naznačen time što se sastoji u:
koraku dobivanja spoja formule (6) iz spoja formule (8), dobivenog Horner-Wadsworth-Emmonsovom reakcijom, i spoja formule (7);
koraku dobivanja spoja formule (5) iz spoja formule (6);
koraku dobivanja spoja formule (3) reakcijom spoja formule (5) s tionil-kloridom (4); i
koraku amidiranja spoja formule (3) reakcijom s 2-aminoetanolom (2):
[image]
(u formuli Me predstavlja metil i R1 predstavlja nerazgranati ili razgranati C1-6alkil).
2. Postupak dobivanja spoja formule (1) u skladu s patentnim zahtjevom 1, naznačen time što se upotrebljava spoj formule (8), dobiven:
(X-1) postupkom dobivanja spoja formule (8) prikazanim u reakcijskoj shemi niže, koji se sastoji u:
koraku dobivanja spoja formule (9) iz spoja formule (11) i difenilfosfonooctene kiseline (10), i
koraku dobivanja spoja formule (8) iz spoja formule (9):
[image]
(u formuli Ts predstavlja p-toluensulfonil, Ph predstavlja fenil, a R1 predstavlja nerazgranati ili razgranati C1-6alkil); ili
(X-2) postupkom dobivanja spoja formule (8) prikazanim u reakcijskoj shemi niže, koji se sastoji u:
koraku dobivanja spoja formule (9-S) reakcijom spoja formule (11) s dietilfosfonooctenom kiselinom (18), te obradi dobivenog sirovog produkta dicikloheksilaminom (17) u metanolu, i
koraku dobivanja spoja formule (8) iz spoja formule (9-S):
[image]
(u formuli Ts predstavlja p-toluensulfonil, Et predstavlja etil, a R1 predstavlja nerazgranati ili razgranati C1-6alkil).
3. Postupak dobivanja spoja formule (1) u skladu s patentnim zahtjevom 2, naznačen time što se upotrebljava spoj formule (11), dobiven:
(Y-1) postupkom dobivanja spoja formule (11) prikazanim u reakcijskoj shemi niže, koji se sastoji u:
koraku dobivanja spoja formule (14) iz spoja formule (16) i metil-4-klorbutirata (15),
koraku dobivanja spoja formule (13) iz spoja formule (14),
koraku dobivanja spoja formule (12) iz spoja formule (13), i
koraku dobivanja spoja formule (11) iz spoja formule (12):
[image]
(u formuli Ts predstavlja p-toluensulfonil, a Me predstavlja metil).
4. Postupak dobivanja spoja formule (1) u skladu s patentnim zahtjevom 3, naznačen time što se u postupku dobivanja (Y-1) spoj formule (13) dobiva bez izdvajanja spoja formule (14), a spoj formule (12) se dobiva bez izdvajanja spoja formule (13).
5. Postupak dobivanja spoja formule (1) u skladu s patentnih zahtjeva 1 do 4, naznačen time što se upotrebljava spoj formule (7), dobiven bilo kojim od:
(Z-1) postupka dobivanja spoja formule (7) prikazanog u reakcijskoj shemi niže, koji se sastoji u:
koraku dobivanja spoja formule (7a) iz spoja formule (7c) i (2R)-2-fluorpropanol (7b), i
koraku dobivanja spoja formule (7) iz spoja formule (7a):
[image]
(u formuli Lv predstavlja izlaznu skupinu, Me predstavlja metil, iPr predstavlja izopropil, a R predstavlja izopropil ili (2R)-2-fluorpropil);
(Z-2) postupka dobivanja spoja formule (7) prikazan u reakcijskoj shemi niže, koji je
korak dobivanja spoja formule (7) iz spoja formule (7e) i (2R)-2-fluorpropanola (7b):
[image]
(u formuli Lv predstavlja izlaznu skupinu, a Me predstavlja metil); ili
(Z-3) postupka dobivanja spoja formule (7) prikazan u reakcijskoj shemi niže, koji se sastoji u:
koraku dobivanja spoja formule (7g) iz spoja formule (7i) i (S)-glicidil-3-nitrobenzensulfonata (7h),
koraku dobivanja spoja formule (7f) reakcijom hidrogeniranja spoja formule (7 g), i
koraku dobivanja spoja formule (7) iz spoja formule (7f):
[image]
(u formuli R2 predstavlja C1-6 alkil, a Me predstavlja metil).
6. Postupak dobivanja spoja formule (1) u skladu s patentnim zahtjevom 1, naznačen time što se upotrebljava spoj formule (8), dobiven postupkom prikazanim u (X-1) u skladu s patentnim zahtjevom 2 i spoj formule (7), dobiven postupkom prikazanim u (Z-1) u skladu s patentnim zahtjevom 5.
7. Postupak dobivanja spoja formule (1) u skladu s patentnim zahtjevom 1, naznačen time što se upotrebljava spoj formule (8), dobiven postupkom prikazanim u (X-2) u skladu s patentnim zahtjevom 2 i spoj formule (7), dobiven postupkom prikazanim u (Z-1) u skladu s patentnim zahtjevom 5.
8. Postupak dobivanja spoja formule (1) u skladu s patentnim zahtjevom 1, naznačen time što se upotrebljava spoj formule (8), dobiven postupkom prikazanim u (X-1) u skladu s patentnim zahtjevom 2 i spoj formule (7), dobiven postupkom prikazanim u (Z-2) u skladu s patentnim zahtjevom 5.
9. Postupak dobivanja spoja formule (1) u skladu s patentnim zahtjevom 1, naznačen time što se upotrebljava spoj formule (8), dobiven postupkom prikazanim u (X-2) u skladu s patentnim zahtjevom 2 i spoj formule (7), dobiven postupkom prikazanim u (Z-2) u skladu s patentnim zahtjevom 5.
10. Postupak dobivanja spoja formule (1) u skladu s patentnim zahtjevom 1, naznačen time što se upotrebljava spoj formule (8), dobiven postupkom prikazanim u (X-1) u skladu s patentnim zahtjevom 2 i spoj formule (7), dobiven postupkom prikazanim u (Z-3) u skladu s patentnim zahtjevom 5.
11. Postupak dobivanja spoja formule (1) u skladu s patentnim zahtjevom 1, naznačen time što se upotrebljava spoj formule (8), dobiven postupkom prikazanim u (X-2) u skladu s patentnim zahtjevom 2 i spoj formule (7), dobiven postupkom prikazanim u (Z-3) u skladu s patentnim zahtjevom 5.
12. Postupak dobivanja spoja formule (1) u skladu s bilo kojim od patentnih zahtjeva 6 do 11, naznačen time što se upotrebljava spoj formule (11), dobiven postupkom prikazanim u (Y-1) u skladu s patentnim zahtjevom 3.
13. Postupak dobivanja spoja formule (1) u skladu s patentnim zahtjevom 12, naznačen time što se u postupku dobivanja (Y-1) spoj formule (13) dobiva bez izdvajanja spoja formule (14), a spoj formule (12) se dobiva bez izdvajanja spoja formule (13).
14. Spoj, naznačen time što je (2Z)-{4,4,7-trifluor-1-[4-{[(2R)-2-fluorpropil]oksi}-2-(trifluormetil)benzoil]-1,2,3,4-tetrahidro-5H-1-benzazepin-5-iliden}acetil-klorid.
15. Spoj, naznačen time što je metil-5-fluor-2-{(4-metoksi-4-oksobutil)[(4-metilfenil)sulfonil]amino}benzoat.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012131504 | 2012-06-11 | ||
| EP13804693.3A EP2860175B1 (en) | 2012-06-11 | 2013-06-11 | Method for producing 4,4,7-trifluoro-1,2,3,4-tetrahydro-5h-1-benzazepine compound and intermediate for synthesis thereof |
| PCT/JP2013/066076 WO2013187406A1 (ja) | 2012-06-11 | 2013-06-11 | 4,4,7-トリフルオロ-1,2,3,4-テトラヒドロ-5h-1-ベンゾアゼピン化合物の製造方法及びその合成中間体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HRP20180032T1 true HRP20180032T1 (hr) | 2018-03-23 |
| HRP20180032T8 HRP20180032T8 (hr) | 2018-12-14 |
Family
ID=49758228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20180032TT HRP20180032T8 (hr) | 2012-06-11 | 2018-01-09 | Postupak dobivanja spoja 4,4,7-trifluor-1,2,3,4-tetrahidro-5h-1-benzazepina i međuprodukta u njegovoj sintezi |
Country Status (15)
| Country | Link |
|---|---|
| US (3) | US9598373B2 (hr) |
| EP (1) | EP2860175B1 (hr) |
| JP (2) | JPWO2013187406A1 (hr) |
| CY (1) | CY1119983T1 (hr) |
| DK (1) | DK2860175T3 (hr) |
| ES (1) | ES2659180T3 (hr) |
| HR (1) | HRP20180032T8 (hr) |
| HU (1) | HUE035391T2 (hr) |
| LT (1) | LT2860175T (hr) |
| NO (1) | NO2860175T3 (hr) |
| PL (1) | PL2860175T3 (hr) |
| PT (1) | PT2860175T (hr) |
| RS (1) | RS56804B1 (hr) |
| SI (1) | SI2860175T1 (hr) |
| WO (1) | WO2013187406A1 (hr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2889239C (en) * | 2012-12-26 | 2020-10-27 | Katsunori Kitamoto | Benzoazepine derivative and medical use thereof |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2857760B2 (ja) * | 1989-02-17 | 1999-02-17 | 第一製薬株式会社 | プロポキシニトロベンゼン類の製法 |
| JP3348860B2 (ja) * | 1996-09-18 | 2002-11-20 | ダイソー株式会社 | グリシジルエーテルの製造法 |
| ATE438626T1 (de) * | 2001-11-16 | 2009-08-15 | Astellas Pharma Inc | 4,4-difluor-1,2,3,4-tetrahydro-5h-1- benzazepinderivate und deren salze |
| WO2004096775A1 (ja) | 2003-04-28 | 2004-11-11 | Astellas Pharma Inc. | ４，４－ジフルオロ－１，２，３，４－テトラヒドロ－５ｈ－１－ベンゾアゼピン誘導体又はその塩 |
| WO2006012093A1 (en) | 2004-06-24 | 2006-02-02 | Eli Lilly And Company | Compounds and methods for treating dyslipidemia |
| JP4765545B2 (ja) | 2004-10-27 | 2011-09-07 | アステラス製薬株式会社 | ベンゾアゼピン誘導体を有効成分とする医薬組成物 |
| JP4765546B2 (ja) | 2004-10-27 | 2011-09-07 | アステラス製薬株式会社 | ベンゾアゼピン誘導体又はその塩の製造法 |
| KR101582056B1 (ko) * | 2008-02-01 | 2015-12-31 | 인터디지탈 패튼 홀딩스, 인크 | 불연속 수신에서 동작하는 ｗｔｒｕ에 대한 셀 재선택을 인에이블하기 위한 방법 및 장치 |
-
2013
- 2013-06-11 LT LTEP13804693.3T patent/LT2860175T/lt unknown
- 2013-06-11 US US14/406,568 patent/US9598373B2/en not_active Expired - Fee Related
- 2013-06-11 HU HUE13804693A patent/HUE035391T2/en unknown
- 2013-06-11 JP JP2014521349A patent/JPWO2013187406A1/ja not_active Ceased
- 2013-06-11 NO NO13804693A patent/NO2860175T3/no unknown
- 2013-06-11 WO PCT/JP2013/066076 patent/WO2013187406A1/ja active Application Filing
- 2013-06-11 PL PL13804693T patent/PL2860175T3/pl unknown
- 2013-06-11 EP EP13804693.3A patent/EP2860175B1/en active Active
- 2013-06-11 RS RS20180081A patent/RS56804B1/sr unknown
- 2013-06-11 PT PT138046933T patent/PT2860175T/pt unknown
- 2013-06-11 SI SI201330925T patent/SI2860175T1/en unknown
- 2013-06-11 DK DK13804693.3T patent/DK2860175T3/da active
- 2013-06-11 ES ES13804693.3T patent/ES2659180T3/es active Active
-
2017
- 2017-02-16 US US15/434,678 patent/US9951022B2/en not_active Expired - Fee Related
-
2018
- 2018-01-09 HR HRP20180032TT patent/HRP20180032T8/hr unknown
- 2018-01-24 CY CY20181100092T patent/CY1119983T1/el unknown
- 2018-03-23 US US15/933,804 patent/US10508084B2/en not_active Expired - Fee Related
- 2018-08-15 JP JP2018152818A patent/JP2019014716A/ja not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2013187406A1 (ja) | 2016-02-04 |
| ES2659180T3 (es) | 2018-03-14 |
| US9951022B2 (en) | 2018-04-24 |
| US10508084B2 (en) | 2019-12-17 |
| EP2860175A4 (en) | 2015-12-09 |
| EP2860175B1 (en) | 2017-11-29 |
| PT2860175T (pt) | 2018-02-02 |
| US20170158639A1 (en) | 2017-06-08 |
| PL2860175T3 (pl) | 2018-07-31 |
| DK2860175T3 (da) | 2018-01-29 |
| LT2860175T (lt) | 2018-03-26 |
| WO2013187406A1 (ja) | 2013-12-19 |
| RS56804B1 (sr) | 2018-04-30 |
| EP2860175A1 (en) | 2015-04-15 |
| SI2860175T1 (en) | 2018-04-30 |
| US20150141641A1 (en) | 2015-05-21 |
| HUE035391T2 (en) | 2018-05-02 |
| US20190062280A1 (en) | 2019-02-28 |
| US9598373B2 (en) | 2017-03-21 |
| HRP20180032T8 (hr) | 2018-12-14 |
| JP2019014716A (ja) | 2019-01-31 |
| NO2860175T3 (hr) | 2018-04-28 |
| CY1119983T1 (el) | 2018-12-12 |
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