CA1076591A - Pharmaceutical compositions comprising substituted 3-cinnamoyl-2h-pyran-2,6(3h)-diones - Google Patents
Pharmaceutical compositions comprising substituted 3-cinnamoyl-2h-pyran-2,6(3h)-dionesInfo
- Publication number
- CA1076591A CA1076591A CA236,817A CA236817A CA1076591A CA 1076591 A CA1076591 A CA 1076591A CA 236817 A CA236817 A CA 236817A CA 1076591 A CA1076591 A CA 1076591A
- Authority
- CA
- Canada
- Prior art keywords
- pyran
- hydroxy
- dione
- cinnamoyl
- acetyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 239000008194 pharmaceutical composition Substances 0.000 title abstract description 5
- NKPVIJNMEQRGPN-UHFFFAOYSA-N 3-(3-phenylprop-2-enoyl)-3h-pyran-2,6-dione Chemical class C1=CC(=O)OC(=O)C1C(=O)C=CC1=CC=CC=C1 NKPVIJNMEQRGPN-UHFFFAOYSA-N 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
- -1 methoxy, methyl Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- ISDVKWGLGFGXJD-UHFFFAOYSA-N chembl3248291 Chemical compound CC(=O)C1=C(O)OC(=O)C(C(C)=O)=C1O ISDVKWGLGFGXJD-UHFFFAOYSA-N 0.000 claims description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- OYNIIKHNXNPSAG-UHFFFAOYSA-N 2-(4-formylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(C=O)C=C1 OYNIIKHNXNPSAG-UHFFFAOYSA-N 0.000 claims description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- MPMAPZBJCRCZNY-UHFFFAOYSA-N 5-acetyl-4-hydroxy-3-[3-(4-hydroxyphenyl)prop-2-enoyl]-3h-pyran-2,6-dione Chemical compound O=C1OC(=O)C(C(=O)C)=C(O)C1C(=O)C=CC1=CC=C(O)C=C1 MPMAPZBJCRCZNY-UHFFFAOYSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 23
- 238000006243 chemical reaction Methods 0.000 abstract description 12
- 230000002401 inhibitory effect Effects 0.000 abstract description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 10
- 241000700159 Rattus Species 0.000 description 8
- 208000024780 Urticaria Diseases 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 4
- 239000000427 antigen Substances 0.000 description 4
- 102000036639 antigens Human genes 0.000 description 4
- 108091007433 antigens Proteins 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- OXTNCQMOKLOUAM-UHFFFAOYSA-N 3-Oxoglutaric acid Chemical compound OC(=O)CC(=O)CC(O)=O OXTNCQMOKLOUAM-UHFFFAOYSA-N 0.000 description 2
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 108010058846 Ovalbumin Proteins 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 229960003699 evans blue Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
- 229940092253 ovalbumin Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229940076279 serotonin Drugs 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- CYXIKYKBLDZZNW-UHFFFAOYSA-N 2-Chloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)CCl CYXIKYKBLDZZNW-UHFFFAOYSA-N 0.000 description 1
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 1
- SKLUWKYNZNXSLX-UHFFFAOYSA-N 4-Acetamidobenzaldehyde Chemical compound CC(=O)NC1=CC=C(C=O)C=C1 SKLUWKYNZNXSLX-UHFFFAOYSA-N 0.000 description 1
- 208000000884 Airway Obstruction Diseases 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- 239000004287 Dehydroacetic acid Substances 0.000 description 1
- 241000359025 Equus kiang Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 201000005702 Pertussis Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229940061632 dehydroacetic acid Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229940074045 glyceryl distearate Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 229940057948 magnesium stearate Drugs 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- KBKWZUVMKBNTFP-UHFFFAOYSA-N n-(3-formylphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(C=O)=C1 KBKWZUVMKBNTFP-UHFFFAOYSA-N 0.000 description 1
- XMXUNPJSQLFNBU-UHFFFAOYSA-N n-[3-[3-(5-acetyl-4-hydroxy-2,6-dioxo-3h-pyran-3-yl)-3-oxoprop-1-enyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=CC(=O)C2C(=C(C(C)=O)C(=O)OC2=O)O)=C1 XMXUNPJSQLFNBU-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51115374A | 1974-10-02 | 1974-10-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1076591A true CA1076591A (en) | 1980-04-29 |
Family
ID=24033666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA236,817A Expired CA1076591A (en) | 1974-10-02 | 1975-10-01 | Pharmaceutical compositions comprising substituted 3-cinnamoyl-2h-pyran-2,6(3h)-diones |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5159869A (cg-RX-API-DMAC10.html) |
| BE (1) | BE834081A (cg-RX-API-DMAC10.html) |
| CA (1) | CA1076591A (cg-RX-API-DMAC10.html) |
| DE (1) | DE2544131C2 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2286647A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1527236A (cg-RX-API-DMAC10.html) |
| IE (1) | IE41905B1 (cg-RX-API-DMAC10.html) |
| ZA (1) | ZA756231B (cg-RX-API-DMAC10.html) |
-
1975
- 1975-09-11 GB GB37418/75A patent/GB1527236A/en not_active Expired
- 1975-09-29 IE IE2126/75A patent/IE41905B1/en unknown
- 1975-09-29 JP JP50118229A patent/JPS5159869A/ja active Pending
- 1975-10-01 ZA ZA00756231A patent/ZA756231B/xx unknown
- 1975-10-01 BE BE160597A patent/BE834081A/xx not_active IP Right Cessation
- 1975-10-01 CA CA236,817A patent/CA1076591A/en not_active Expired
- 1975-10-02 DE DE2544131A patent/DE2544131C2/de not_active Expired
- 1975-10-02 FR FR7530206A patent/FR2286647A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IE41905B1 (en) | 1980-04-23 |
| DE2544131A1 (de) | 1976-04-15 |
| FR2286647B1 (cg-RX-API-DMAC10.html) | 1979-09-14 |
| JPS5159869A (cg-RX-API-DMAC10.html) | 1976-05-25 |
| IE41905L (en) | 1976-04-02 |
| GB1527236A (en) | 1978-10-04 |
| BE834081A (fr) | 1976-04-01 |
| ZA756231B (en) | 1976-09-29 |
| FR2286647A1 (fr) | 1976-04-30 |
| AU8538075A (en) | 1977-04-07 |
| DE2544131C2 (de) | 1984-04-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4009847A (en) | 1-Tertiary-alkyl-3-(substituted thienyl)ureas and 1-tertiary-alkyl-3-(substituted thietyl)ureas as antihypertensive agents | |
| JP4171527B2 (ja) | カンプトテシン誘導体及び抗腫瘍剤としてのその利用 | |
| US4238496A (en) | 4-Substituted thiazolyl-2-oxamic acids and salts and esters thereof | |
| CA1096869A (en) | Pyridine derivative, its preparation and use | |
| CA1076591A (en) | Pharmaceutical compositions comprising substituted 3-cinnamoyl-2h-pyran-2,6(3h)-diones | |
| US4015009A (en) | Pharmaceutical compositions comprising substituted 3-cinnamoyl-2H-pyran-2,6(3H)-diones | |
| Cromwell et al. | The Chemistry of Derivatives of 2-Benzaltetralone. IV. 1 The Synthesis, Spectra and Ring Cleavage Reactions of Some Spiroepoxyketones | |
| EP0269355B1 (en) | Imidazolidinedione derivatives | |
| FI84482B (fi) | Foerfarande foer framstaellning av farmakologiskt vaerdefulla bensodipyran. | |
| US3984429A (en) | Pharmaceutically active compounds | |
| JPS6231704B2 (cg-RX-API-DMAC10.html) | ||
| CH616935A5 (en) | Process for the preparation of chromone derivatives | |
| JPS6135991B2 (cg-RX-API-DMAC10.html) | ||
| US3984534A (en) | Tetrazolyl anthraquinones for inhibiting the release of spasmogen mediators | |
| US3534029A (en) | Preparation intermediate products of cephalosporins | |
| US3470165A (en) | Furochromone derivatives | |
| US4117226A (en) | Substituted 3-cinnamoyl-2h-pyran-2,6(3h)-diones | |
| CA1040640A (en) | Indazole-3-carboxylic acid hydrazides and a process for the preparation thereof | |
| US3987186A (en) | 2-carboxy-4-oxo-4h,6h-(2)-benzopyrano-(3,4-f)-(1)-benzopyrans and esters and salts thereof | |
| US3901925A (en) | 2-carboxy-4-oxo-4h,10h-(2)-benzopyrano-(4,3-g)-(1)-benzopyrans and salts thereof | |
| CA1057661A (en) | Pharmaceutical compositions comprising substituted 4,6-dihydroxy-2h-pyran-2-ones | |
| US4085116A (en) | Novel chromone derivatives | |
| CA1113927A (en) | Derivatives of 7-(cyclized)phenylglycyl cephalosporin | |
| JPH0227356B2 (cg-RX-API-DMAC10.html) | ||
| US4153720A (en) | 3-Acyl-5-alkyl-2H-pyran-2,4,6-(3H,5H)-triones and their 4-hydroxy tautomers |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |