CA2585654C - Use of acetyl l-carnitine in combination with propionyl l-carnitine and sildenafil for the treatment of erectile dysfunction - Google Patents
Use of acetyl l-carnitine in combination with propionyl l-carnitine and sildenafil for the treatment of erectile dysfunction Download PDFInfo
- Publication number
- CA2585654C CA2585654C CA2585654A CA2585654A CA2585654C CA 2585654 C CA2585654 C CA 2585654C CA 2585654 A CA2585654 A CA 2585654A CA 2585654 A CA2585654 A CA 2585654A CA 2585654 C CA2585654 C CA 2585654C
- Authority
- CA
- Canada
- Prior art keywords
- carnitine
- therapy
- sildenafil
- acetyl
- propionyl
- 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 - Fee Related
Links
- BNRNXUUZRGQAQC-UHFFFAOYSA-N sildenafil Chemical compound CCCC1=NN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 BNRNXUUZRGQAQC-UHFFFAOYSA-N 0.000 title claims abstract description 66
- RDHQFKQIGNGIED-MRVPVSSYSA-N O-acetyl-L-carnitine Chemical compound CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C RDHQFKQIGNGIED-MRVPVSSYSA-N 0.000 title claims abstract description 62
- 229960003310 sildenafil Drugs 0.000 title claims abstract description 33
- 208000010228 Erectile Dysfunction Diseases 0.000 title claims abstract description 29
- 201000001881 impotence Diseases 0.000 title claims abstract description 29
- UFAHZIUFPNSHSL-MRVPVSSYSA-N O-propanoyl-L-carnitine Chemical compound CCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C UFAHZIUFPNSHSL-MRVPVSSYSA-N 0.000 title claims description 50
- 239000003814 drug Substances 0.000 claims abstract description 17
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 4
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- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
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- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 2
- QWJSAWXRUVVRLH-LREBCSMRSA-M 2-hydroxyethyl(trimethyl)azanium;(2r,3r)-2,3,4-trihydroxy-4-oxobutanoate Chemical compound C[N+](C)(C)CCO.OC(=O)[C@H](O)[C@@H](O)C([O-])=O QWJSAWXRUVVRLH-LREBCSMRSA-M 0.000 claims description 2
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 2
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229960005336 magnesium citrate Drugs 0.000 claims description 2
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- MUZDLCBWNVUYIR-ZVGUSBNCSA-L magnesium;(2r,3r)-2,3-dihydroxybutanedioate Chemical compound [Mg+2].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O MUZDLCBWNVUYIR-ZVGUSBNCSA-L 0.000 claims description 2
- QUIOHQITLKCGNW-TYYBGVCCSA-L magnesium;(e)-but-2-enedioate Chemical compound [Mg+2].[O-]C(=O)\C=C\C([O-])=O QUIOHQITLKCGNW-TYYBGVCCSA-L 0.000 claims description 2
- PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 claims description 2
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 claims description 2
- PLSARIKBYIPYPF-UHFFFAOYSA-H trimagnesium dicitrate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O PLSARIKBYIPYPF-UHFFFAOYSA-H 0.000 claims description 2
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- 230000009429 distress Effects 0.000 abstract description 5
- 230000000642 iatrogenic effect Effects 0.000 abstract description 5
- 229960004203 carnitine Drugs 0.000 abstract description 4
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 abstract description 3
- PHIQHXFUZVPYII-ZCFIWIBFSA-O (R)-carnitinium Chemical compound C[N+](C)(C)C[C@H](O)CC(O)=O PHIQHXFUZVPYII-ZCFIWIBFSA-O 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 description 164
- 229940103087 sildenafil 100 mg Drugs 0.000 description 44
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- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 230000000422 nocturnal effect Effects 0.000 description 4
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 4
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- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical group CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 description 2
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 206010060862 Prostate cancer Diseases 0.000 description 2
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- SECKRCOLJRRGGV-UHFFFAOYSA-N Vardenafil Chemical compound CCCC1=NC(C)=C(C(N=2)=O)N1NC=2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(CC)CC1 SECKRCOLJRRGGV-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
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- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
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- MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 description 1
- 239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
- GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
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- 229910052711 selenium Inorganic materials 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/191—Carboxylic acids, e.g. valproic acid having two or more hydroxy groups, e.g. gluconic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4418—Non condensed pyridines; Hydrogenated derivatives thereof having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Reproductive Health (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Endocrinology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT000561A ITRM20040561A1 (it) | 2004-11-11 | 2004-11-11 | Uso della acetil l-carnitina in combinazione con propionil l-carnitina e sildenafil per il trattamento della disfunzione erettile. |
| ITRM2004A000561 | 2004-11-11 | ||
| PCT/EP2005/011238 WO2006050794A1 (en) | 2004-11-11 | 2005-10-19 | Use of acetyl l-carnitine in combination with propionyl l-carnitine and sildenafil for the treatment of erectile dysfunction |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2585654A1 CA2585654A1 (en) | 2006-05-18 |
| CA2585654C true CA2585654C (en) | 2013-04-02 |
Family
ID=35501123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2585654A Expired - Fee Related CA2585654C (en) | 2004-11-11 | 2005-10-19 | Use of acetyl l-carnitine in combination with propionyl l-carnitine and sildenafil for the treatment of erectile dysfunction |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8003652B2 (enExample) |
| EP (1) | EP1811988B1 (enExample) |
| JP (1) | JP5080263B2 (enExample) |
| KR (1) | KR101455275B1 (enExample) |
| AT (1) | ATE456950T1 (enExample) |
| CA (1) | CA2585654C (enExample) |
| CY (1) | CY1110239T1 (enExample) |
| DE (1) | DE602005019251D1 (enExample) |
| DK (1) | DK1811988T3 (enExample) |
| ES (1) | ES2339265T3 (enExample) |
| IT (1) | ITRM20040561A1 (enExample) |
| MX (1) | MX2007005518A (enExample) |
| PL (1) | PL1811988T3 (enExample) |
| PT (1) | PT1811988E (enExample) |
| SI (1) | SI1811988T1 (enExample) |
| WO (1) | WO2006050794A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010222347A (ja) * | 2009-02-24 | 2010-10-07 | Daiichi Sankyo Healthcare Co Ltd | Ｐｄｅ５阻害剤及びカルニチンを含有する医薬組成物 |
| WO2012000634A1 (de) | 2010-06-29 | 2012-01-05 | Georg Bambach | Pharmazeutische zusammensetzung zur behandlung von erektiler dysfunktion |
| WO2018070971A1 (ru) * | 2016-10-10 | 2018-04-19 | Товарыство З Обмэжэною Видповидальнистю Науково-Выробныча Фирма "Микрохим" | Фармацевтическая композиция в форме оромукозного спрея для лечения эректильной дисфункции и легочной артериальной гипертензии |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1077260B1 (en) | 1999-08-13 | 2010-03-31 | Deutsches Krebsforschungszentrum Stiftung des öffentlichen Rechts | Parvovirus NS1 variants |
| IT1306722B1 (it) * | 1999-10-08 | 2001-10-02 | Sigma Tau Healthscience Spa | Composizione per la prevenzione e/o il trattamento di disfunzionicircolatorie, comprendente derivati della l-carnitina ed estratti di |
| JP2001233770A (ja) * | 2000-02-23 | 2001-08-28 | Dountsuendorufaa Udo | 勃起機能不全治療用の経口薬の組合わせ |
| ITRM20010621A1 (it) * | 2001-10-18 | 2003-04-18 | Aldo Fassi | Sali metallici non igroscopici e idrosolubili di alcanoil l-carnitine, integratori dietetici che li contengono e kit dietetici, per contrast |
| ITRM20010708A1 (it) * | 2001-12-04 | 2003-06-04 | Sigma Tau Ind Farmaceuti | Uso di una alcanoil l-carnitina per il trattamento della disfunzione erettile. |
| ITRM20020620A1 (it) * | 2002-12-13 | 2004-06-14 | Sigma Tau Ind Farmaceuti | Uso delle carnitine per la prevenzione e/o il trattamento dei disturbi causati dall'andropausa. |
-
2004
- 2004-11-11 IT IT000561A patent/ITRM20040561A1/it unknown
-
2005
- 2005-10-19 AT AT05798477T patent/ATE456950T1/de active
- 2005-10-19 DE DE602005019251T patent/DE602005019251D1/de not_active Expired - Lifetime
- 2005-10-19 ES ES05798477T patent/ES2339265T3/es not_active Expired - Lifetime
- 2005-10-19 CA CA2585654A patent/CA2585654C/en not_active Expired - Fee Related
- 2005-10-19 WO PCT/EP2005/011238 patent/WO2006050794A1/en not_active Ceased
- 2005-10-19 PT PT05798477T patent/PT1811988E/pt unknown
- 2005-10-19 PL PL05798477T patent/PL1811988T3/pl unknown
- 2005-10-19 US US11/719,011 patent/US8003652B2/en not_active Expired - Fee Related
- 2005-10-19 JP JP2007540521A patent/JP5080263B2/ja not_active Expired - Fee Related
- 2005-10-19 KR KR1020077013019A patent/KR101455275B1/ko not_active Expired - Fee Related
- 2005-10-19 DK DK05798477.5T patent/DK1811988T3/da active
- 2005-10-19 EP EP05798477A patent/EP1811988B1/en not_active Expired - Lifetime
- 2005-10-19 SI SI200530953T patent/SI1811988T1/sl unknown
- 2005-10-19 MX MX2007005518A patent/MX2007005518A/es active IP Right Grant
-
2010
- 2010-04-23 CY CY20101100362T patent/CY1110239T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US8003652B2 (en) | 2011-08-23 |
| ITRM20040561A1 (it) | 2005-02-11 |
| DE602005019251D1 (de) | 2010-03-25 |
| WO2006050794A1 (en) | 2006-05-18 |
| JP2008531466A (ja) | 2008-08-14 |
| CA2585654A1 (en) | 2006-05-18 |
| ATE456950T1 (de) | 2010-02-15 |
| PL1811988T3 (pl) | 2010-07-30 |
| PT1811988E (pt) | 2010-04-08 |
| EP1811988A1 (en) | 2007-08-01 |
| SI1811988T1 (sl) | 2010-10-29 |
| DK1811988T3 (da) | 2010-05-17 |
| EP1811988B1 (en) | 2010-02-03 |
| CY1110239T1 (el) | 2015-01-14 |
| ES2339265T3 (es) | 2010-05-18 |
| MX2007005518A (es) | 2007-05-18 |
| JP5080263B2 (ja) | 2012-11-21 |
| US20080090906A1 (en) | 2008-04-17 |
| KR101455275B1 (ko) | 2014-10-27 |
| KR20070085961A (ko) | 2007-08-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20201019 |