SU1272991A3 - Способ получени производных гуанина в виде рацематов или @ ( @ ) изомеров - Google Patents
Способ получени производных гуанина в виде рацематов или @ ( @ ) изомеров Download PDFInfo
- Publication number
- SU1272991A3 SU1272991A3 SU823480213A SU3480213A SU1272991A3 SU 1272991 A3 SU1272991 A3 SU 1272991A3 SU 823480213 A SU823480213 A SU 823480213A SU 3480213 A SU3480213 A SU 3480213A SU 1272991 A3 SU1272991 A3 SU 1272991A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- guanine
- guanine derivatives
- racemates
- isomers
- compound
- Prior art date
Links
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical class O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 230000000840 anti-viral effect Effects 0.000 claims abstract description 11
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims description 3
- 231100000053 low toxicity Toxicity 0.000 claims description 2
- HDGHQFQMWUTHKL-UHFFFAOYSA-N 2-methyl-1,3-dioxane Chemical group CC1OCCCO1 HDGHQFQMWUTHKL-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 4
- 201000010099 disease Diseases 0.000 abstract description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 125000001153 fluoro group Chemical group F* 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 241000700605 Viruses Species 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000009385 viral infection Effects 0.000 abstract 1
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 7
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 229940104230 thymidine Drugs 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 102000006601 Thymidine Kinase Human genes 0.000 description 3
- 108020004440 Thymidine kinase Proteins 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000026731 phosphorylation Effects 0.000 description 3
- 238000006366 phosphorylation reaction Methods 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 238000002211 ultraviolet spectrum Methods 0.000 description 3
- WJSVJNDMOQTICG-UHFFFAOYSA-N 2-amino-1-[(2-methyl-4-methylidene-5-oxooxolan-2-yl)methyl]-7h-purin-6-one Chemical compound NC1=NC=2N=CNC=2C(=O)N1CC1(C)CC(=C)C(=O)O1 WJSVJNDMOQTICG-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 150000004712 monophosphates Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 210000003501 vero cell Anatomy 0.000 description 2
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
- QEQROBXJKMVNGZ-UHFFFAOYSA-N 6-chloro-9-(1,3-dioxan-4-ylmethyl)purin-2-amine Chemical compound C12=NC(N)=NC(Cl)=C2N=CN1CC1CCOCO1 QEQROBXJKMVNGZ-UHFFFAOYSA-N 0.000 description 1
- BOCYHPJEADDNID-UHFFFAOYSA-N CC(=C(C(CCN1C=NC2=C1N=C(N=C2Cl)N)O)O)C Chemical compound CC(=C(C(CCN1C=NC2=C1N=C(N=C2Cl)N)O)O)C BOCYHPJEADDNID-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Detection And Prevention Of Errors In Transmission (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8009040 | 1980-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1272991A3 true SU1272991A3 (ru) | 1986-11-23 |
Family
ID=20342543
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU823480213A SU1272991A3 (ru) | 1980-12-22 | 1982-08-20 | Способ получени производных гуанина в виде рацематов или @ ( @ ) изомеров |
| SU833657074A SU1272992A3 (ru) | 1980-12-22 | 1983-10-31 | Способ получени 9-(3,4-диоксибутил)-гуанина |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU833657074A SU1272992A3 (ru) | 1980-12-22 | 1983-10-31 | Способ получени 9-(3,4-диоксибутил)-гуанина |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4495190A (enExample) |
| EP (1) | EP0055239B1 (enExample) |
| JP (1) | JPS57501963A (enExample) |
| AT (1) | ATE20748T1 (enExample) |
| AU (1) | AU542373B2 (enExample) |
| CA (1) | CA1172633A (enExample) |
| DE (1) | DE3174948D1 (enExample) |
| DK (1) | DK148279C (enExample) |
| FI (1) | FI68054C (enExample) |
| GR (1) | GR76971B (enExample) |
| IL (1) | IL64501A (enExample) |
| NO (1) | NO822712L (enExample) |
| NZ (1) | NZ199334A (enExample) |
| RO (1) | RO85288B (enExample) |
| SU (2) | SU1272991A3 (enExample) |
| WO (1) | WO1982002202A1 (enExample) |
| ZA (1) | ZA818781B (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8203856D0 (sv) * | 1982-06-21 | 1982-06-21 | Astra Laekemedel Ab | Novel derivatives of guanine ii |
| SE8203855D0 (sv) * | 1982-06-21 | 1982-06-21 | Astra Laekemedel Ab | Novel derivatives of guanine i |
| US5047533A (en) * | 1983-05-24 | 1991-09-10 | Sri International | Acyclic purine phosphonate nucleotide analogs |
| HUT36464A (en) * | 1983-05-24 | 1985-09-30 | Newport Pharmaceuticals | Process for producing erythro-4-amino-3-/2-hydroxy-3-alkyl/-imidazol-5-carboxamide |
| GB8320308D0 (en) * | 1983-07-28 | 1983-09-01 | Wellcome Found | Antiviral combinations |
| EP0141927B1 (en) * | 1983-08-18 | 1991-10-30 | Beecham Group Plc | Antiviral guanine derivatives |
| US5684153A (en) | 1984-08-16 | 1997-11-04 | Beecham Group Plc | Process for the preparation of purine derivatives |
| IL73682A (en) * | 1983-12-20 | 1991-08-16 | Medivir Ab | Antiviral pharmaceutical compositions containing 9-hydroxy aliphatic derivatives of guanine,some new such derivatives and process for their preparation |
| US4579849A (en) * | 1984-04-06 | 1986-04-01 | Merck & Co., Inc. | N-alkylguanine acyclonucleosides as antiviral agents |
| US4801710A (en) * | 1984-10-26 | 1989-01-31 | Merck & Co., Inc. | Regioselective synthesis of 9-substituted purine acyclonucleoside derivatives |
| YU45690B (sh) * | 1984-12-22 | 1992-07-20 | Krka Tovarna Zdraviln.Sol.O. | Postopek za pripravo 9-(2-hidroksietoksimetil)-gvanina |
| EP0193454A1 (en) * | 1985-02-25 | 1986-09-03 | Merck & Co. Inc. | 8-Substituted-9-hydroxyalkyl and hydroxyalkoxymethyl-guanines and pharmaceutical compositions containing them |
| EP0219838A3 (en) * | 1985-10-22 | 1988-04-06 | Takeda Chemical Industries, Ltd. | Carbocyclic purine nucleosides, their production and use |
| US5578468A (en) * | 1987-08-10 | 1996-11-26 | Duke University | Site-specific RNA cleavage |
| US5443964A (en) * | 1987-08-10 | 1995-08-22 | Duke University | Poxvirus insertion/expression vector |
| US4935427A (en) * | 1987-12-31 | 1990-06-19 | The United States Of America As Represented By The Department Of Health And Human Services | Pyrimidine and purine 1,2-butadiene-4-ols as anti-retroviral agents |
| US4966895A (en) * | 1989-02-02 | 1990-10-30 | Merck & Co. Inc. | Cyclic monophosphates of purine and pyrimidine acyclonucleosides as anti-retroviral agents |
| US5352669A (en) * | 1990-03-13 | 1994-10-04 | The Of The United States Of America As Represented By The Department Of Health And Human Services | O6 -benzylated guanine, guanosine and 2'-deoxyguanosine compounds possessing O6 -alkylguanine-DNA alkyltransferase depleting activity |
| US5091432A (en) * | 1990-03-28 | 1992-02-25 | Glasky Alvin J | 9-substituted hypoxanthine bi-functional compounds and their neuroimmunological methods of use |
| CZ285420B6 (cs) * | 1990-04-24 | 1999-08-11 | Ústav Organické Chemie A Biochemie Avčr | N-(3-Fluor-2-fosfonylmethoxypropyl)deriváty purinových a pyrimidinových heterocyklických bazí, způsoby jejich přípravy a použití |
| US5368853A (en) * | 1990-05-11 | 1994-11-29 | The United States Of America As Represented By The Secretary Of The Department Of Health & Human Services | Leukoregulin anti-viral therapy |
| JP2939646B2 (ja) * | 1990-07-17 | 1999-08-25 | チッソ株式会社 | ４―置換―２―ヒドロキシブタン酸エステルおよび製造法 |
| US5874578A (en) * | 1992-07-13 | 1999-02-23 | Bristol-Myers Squibb | Process for preparing guanine-containing antiviral agents and purinyl salts useful in such process |
| US5525606A (en) | 1994-08-01 | 1996-06-11 | The United States Of America As Represented By The Department Of Health And Human Services | Substituted 06-benzylguanines and 6(4)-benzyloxypyrimidines |
| US6359114B1 (en) | 1995-06-07 | 2002-03-19 | Aphton Corp. | System for method for the modification and purification of proteins |
| US6060458A (en) * | 1998-02-13 | 2000-05-09 | The United States Of America As Represented By The Department Of Health And Human Services | Oligodeoxyribonucleotides comprising O6 -benzylguanine and their use |
| EP1440072A4 (en) | 2001-10-30 | 2005-02-02 | Conforma Therapeutic Corp | PURINE ANALOGS HAVING HSP90 INHIBITORY ACTIVITY |
| US20070129334A1 (en) * | 2001-10-30 | 2007-06-07 | Conforma Therapeutics Corporation | Orally Active Purine-Based Inhibitors of Heat Shock Protein 90 |
| NZ546611A (en) | 2003-09-18 | 2010-02-26 | Conforma Therapeutics Corp | Novel heterocyclic compounds as HSP90-inhibitors |
| BRPI0609509A2 (pt) | 2005-03-30 | 2010-04-13 | Conforma Therapeutics Corp | composto ou um polimorfo, solvato, tautÈmero, enanciÈmero, pró-droga ou sal farmaceuticamente aceitável do mesmo, composição farmacêutica, e, uso do composto, polimorfo, solvato, tautÈmero, enanciÈmero, pró-droga ou sal farmaceuticamente aceitável |
| CA2653247C (en) * | 2005-06-14 | 2012-12-18 | Brigham Young University | Methods for selective n-9 glycosylation of purines |
| US20070105874A1 (en) * | 2005-09-23 | 2007-05-10 | Conforma Therapeutics Corporation | Anti-Tumor Methods Using Multi Drug Resistance Independent Synthetic HSP90 Inhibitors |
| CN108912055B (zh) * | 2018-08-20 | 2020-06-30 | 河南师范大学 | 一种合成抗病毒药物西多福韦中间体和布昔洛韦中间体的方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL34188A (en) * | 1969-04-09 | 1972-12-29 | Seiyaku T Co | 4-(9-adenyl)-2,3-dihydroxy butyric acid and the preparation thereof |
| US3836656A (en) * | 1972-02-07 | 1974-09-17 | Sandoz Ag | Substituted purines as hypolipidemics |
| US4199574A (en) * | 1974-09-02 | 1980-04-22 | Burroughs Wellcome Co. | Methods and compositions for treating viral infections and guanine acyclic nucleosides |
| US4230708A (en) * | 1977-10-20 | 1980-10-28 | Stichting Rega V.Z.W. | Therapeutic application of (S) -or (RS)-9-(2, 3-dihydroxypropyl) adenine for use as antiviral agents |
| CS199093B1 (en) * | 1977-10-20 | 1980-07-31 | Antonin Holy | Antiviral agent |
| US4221910A (en) * | 1978-09-15 | 1980-09-09 | Newport Pharmaceuticals International, Inc. | 9-(Hydroxy alkyl)purines |
| US4423050A (en) * | 1981-05-21 | 1983-12-27 | Syntex (U.S.A.) Inc. | 9-(1,3-Dihydroxy-2-propoxymethyl)guanine as antiviral agent |
| US4451478A (en) * | 1982-03-12 | 1984-05-29 | Newport Pharmaceuticals International, Inc. | Imidazole compounds |
-
1981
- 1981-12-10 IL IL64501A patent/IL64501A/xx unknown
- 1981-12-18 ZA ZA818781A patent/ZA818781B/xx unknown
- 1981-12-21 NZ NZ199334A patent/NZ199334A/xx unknown
- 1981-12-21 GR GR66864A patent/GR76971B/el unknown
- 1981-12-21 AU AU78721/81A patent/AU542373B2/en not_active Ceased
- 1981-12-21 CA CA000392782A patent/CA1172633A/en not_active Expired
- 1981-12-22 EP EP81850250A patent/EP0055239B1/en not_active Expired
- 1981-12-22 DE DE8181850250T patent/DE3174948D1/de not_active Expired
- 1981-12-22 AT AT81850250T patent/ATE20748T1/de not_active IP Right Cessation
- 1981-12-22 WO PCT/SE1981/000389 patent/WO1982002202A1/en not_active Ceased
- 1981-12-22 JP JP57500239A patent/JPS57501963A/ja active Pending
-
1982
- 1982-08-09 NO NO822712A patent/NO822712L/no unknown
- 1982-08-18 DK DK369982A patent/DK148279C/da not_active IP Right Cessation
- 1982-08-19 FI FI822891A patent/FI68054C/fi not_active IP Right Cessation
- 1982-08-20 SU SU823480213A patent/SU1272991A3/ru active
- 1982-08-21 RO RO108498A patent/RO85288B/ro unknown
- 1982-10-25 US US06/436,522 patent/US4495190A/en not_active Expired - Fee Related
-
1983
- 1983-10-31 SU SU833657074A patent/SU1272992A3/ru active
Non-Patent Citations (1)
| Title |
|---|
| Патент US № 4199574, кл. А 61 К 31/52, опублик. 1980. Вейганд-Хильгетаг. Методы эксперимента в органической химии. - М.: Хими , 1968, с. 316. * |
Also Published As
| Publication number | Publication date |
|---|---|
| RO85288B (ro) | 1984-11-30 |
| JPS57501963A (enExample) | 1982-11-04 |
| NZ199334A (en) | 1985-09-13 |
| ZA818781B (en) | 1982-11-24 |
| EP0055239B1 (en) | 1986-07-16 |
| US4495190A (en) | 1985-01-22 |
| WO1982002202A1 (en) | 1982-07-08 |
| IL64501A (en) | 1985-07-31 |
| CA1172633A (en) | 1984-08-14 |
| NO822712L (no) | 1982-08-09 |
| IL64501A0 (en) | 1982-03-31 |
| FI68054B (fi) | 1985-03-29 |
| AU7872181A (en) | 1982-07-01 |
| DK369982A (da) | 1982-08-18 |
| FI822891A0 (fi) | 1982-08-19 |
| FI68054C (fi) | 1985-07-10 |
| DK148279B (da) | 1985-05-28 |
| GR76971B (enExample) | 1984-09-04 |
| EP0055239A1 (en) | 1982-06-30 |
| RO85288A (ro) | 1984-11-25 |
| AU542373B2 (en) | 1985-02-21 |
| DK148279C (da) | 1986-02-17 |
| SU1272992A3 (ru) | 1986-11-23 |
| DE3174948D1 (en) | 1986-08-21 |
| ATE20748T1 (de) | 1986-08-15 |
| FI822891L (fi) | 1982-08-19 |
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