DE1668915A1 - Neue Phenaethylamin-Salze und Verfahren zu deren Herstellung - Google Patents
Neue Phenaethylamin-Salze und Verfahren zu deren HerstellungInfo
- Publication number
- DE1668915A1 DE1668915A1 DE19681668915 DE1668915A DE1668915A1 DE 1668915 A1 DE1668915 A1 DE 1668915A1 DE 19681668915 DE19681668915 DE 19681668915 DE 1668915 A DE1668915 A DE 1668915A DE 1668915 A1 DE1668915 A1 DE 1668915A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- hydrogen
- carbon atoms
- alkyl
- independently
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000003839 salts Chemical class 0.000 title 1
- -1 Alkyl radical Chemical class 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 4
- 239000012433 hydrogen halide Substances 0.000 claims description 4
- 241000251730 Chondrichthyes Species 0.000 claims description 3
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical class NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 150000001541 aziridines Chemical class 0.000 claims description 3
- 229940048346 phenethylamine hydrochloride Drugs 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- OZDGMOYKSFPLSE-UHFFFAOYSA-N 2-Methylaziridine Chemical compound CC1CN1 OZDGMOYKSFPLSE-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical compound Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 description 1
- SKHIBNDAFWIOPB-UHFFFAOYSA-N hydron;2-phenylethanamine;chloride Chemical class Cl.NCCC1=CC=CC=C1 SKHIBNDAFWIOPB-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Drawers Of Furniture (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH238667A CH481110A (de) | 1967-02-17 | 1967-02-17 | Verfahren zur Herstellung von 1,2,4,5-Tetrahydro-3-azepinen |
| CH1167167A CH488705A (de) | 1967-02-17 | 1967-08-18 | Verfahren zur Herstellung eines neuen Tetrahydroazepinderivates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1668915A1 true DE1668915A1 (de) | 1972-03-09 |
Family
ID=25690322
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681668915 Pending DE1668915A1 (de) | 1967-02-17 | 1968-02-16 | Neue Phenaethylamin-Salze und Verfahren zu deren Herstellung |
| DE19681695124 Pending DE1695124A1 (de) | 1967-02-17 | 1968-02-16 | Verfahren zur Herstellung von Tetrahydroazepinderivaten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681695124 Pending DE1695124A1 (de) | 1967-02-17 | 1968-02-16 | Verfahren zur Herstellung von Tetrahydroazepinderivaten |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3652543A (OSRAM) |
| AT (1) | AT275533B (OSRAM) |
| BE (1) | BE710872A (OSRAM) |
| CH (2) | CH481110A (OSRAM) |
| DE (2) | DE1668915A1 (OSRAM) |
| DK (1) | DK115473B (OSRAM) |
| ES (1) | ES350574A1 (OSRAM) |
| FR (2) | FR1561479A (OSRAM) |
| GB (2) | GB1221324A (OSRAM) |
| IL (1) | IL29485A (OSRAM) |
| NL (1) | NL6802257A (OSRAM) |
| NO (1) | NO124369B (OSRAM) |
| SE (1) | SE342043B (OSRAM) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT289812B (de) * | 1968-08-09 | 1971-05-10 | Geigy Ag J R | Verfahren zur Herstellung des neuen 2-Methyl-7-chlor-2,3,4,5-tetrahydro-1H-3-benzazepins sowie seiner Säureadditionssalze |
| DE2016136A1 (de) * | 1970-04-04 | 1971-10-14 | C H Boehnnger Sohn, 6507 Ingel heim | Neue 7 Acyl 1,2,4,5 tetrahydro (3H) 3 benzazepine |
| DE2143204C3 (de) * | 1971-08-28 | 1979-09-27 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | N-Fluoralkyl-phenylisopropylamin-Derivate und deren Salze, Verfahren zu deren Herstellung und Arzneimittel auf deren Basis |
| DE2207430C3 (de) * | 1972-02-14 | 1982-05-13 | Pennwalt Corp., 19102 Philadelphia, Pa. | 1,2,4,5-Tetrahydro-3H-3-benzazepin, ein Verfahren zu ihrer Herstellung und diese enthaltendes pharmazeutisches Mittel |
| EP0161350A1 (en) * | 1981-11-27 | 1985-11-21 | Smithkline Beckman Corporation | Process for preparing benzazepines |
| US4541954A (en) * | 1984-09-05 | 1985-09-17 | Smithkline Beckman Corporation | Method for preparing 6-chloro-N-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine |
| US4973586A (en) * | 1986-01-16 | 1990-11-27 | Schering Corporation | Fused benzazepines, compositions of, and medical use thereof |
| US5302716A (en) * | 1986-01-16 | 1994-04-12 | Schering Corporation | Fused benzazepines |
| EP0254737B1 (en) * | 1986-01-16 | 1990-07-25 | Schering Corporation | Fused benzazepines |
| US5015639A (en) * | 1987-03-27 | 1991-05-14 | Schering Corporation | Substituted benzazepines, their preparation and pharmaceutical compositions containing them |
| HU203537B (en) * | 1987-07-15 | 1991-08-28 | Schering Corp | Process for producing condensed benzazepine derivatives and pharmaceutical compositions containing them |
| WO1991011437A1 (en) * | 1990-02-02 | 1991-08-08 | Schering Corporation | 4,5-cycloalkano-3-benzazepin-7-ol-derivatives and their use |
| US6953787B2 (en) * | 2002-04-12 | 2005-10-11 | Arena Pharmaceuticals, Inc. | 5HT2C receptor modulators |
| US20030220661A1 (en) * | 2002-05-21 | 2003-11-27 | Heartstent Corporation | Transmyocardial implant delivery system |
| MXPA05013366A (es) * | 2003-06-17 | 2006-04-05 | Arena Pharm Inc | Derivados de benzazepina utiles para el tratamiento de enfermedades asociadas con el receptor 5ht2c. |
| EP2332919A3 (en) * | 2003-06-17 | 2011-10-19 | Arena Pharmaceuticals, Inc. | Processes for preparing 3-benzazepines |
| WO2005042490A1 (en) * | 2003-10-22 | 2005-05-12 | Arena Pharmaceuticals, Inc. | Benzazepine derivatives and methods of prophylaxis or treatment of 5ht2c receptor associated diseases |
| WO2005042491A1 (en) * | 2003-10-22 | 2005-05-12 | Arena Pharmaceuticals, Inc. | Benzazepine derivatives and methods of prophylaxis or treatment of 5ht2c receptor associated diseases |
| PT1838677E (pt) | 2004-12-21 | 2009-11-16 | Arena Pharm Inc | Formas cristalinas do cloridrato de (r)-8-cloro-1-metil- 2,3,4,5-tetra-hidro-1h-3-benzazepina |
| PT1833473E (pt) | 2004-12-23 | 2009-12-17 | Arena Pharm Inc | Composições de modulador de receptor 5ht2c e métodos de utilização |
| EP2518053A1 (en) * | 2006-04-03 | 2012-10-31 | Arena Pharmaceuticals, Inc. | Process for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine |
| WO2008070111A2 (en) * | 2006-12-05 | 2008-06-12 | Arena Pharmaceuticals, Inc. | Processes for preparing (r)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine and intermediates thereof |
| EP2288585A1 (en) * | 2008-03-04 | 2011-03-02 | Arena Pharmaceuticals, Inc. | Processes for the preparation of intermediates related to the 5-ht2c agonist (r)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine |
| US8952197B2 (en) | 2009-06-18 | 2015-02-10 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 5-HT2C receptor agonists |
| WO2011071136A1 (ja) | 2009-12-11 | 2011-06-16 | アステラス製薬株式会社 | 線維筋痛症治療剤 |
| US9045431B2 (en) | 2010-06-02 | 2015-06-02 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 5-HT2C receptor agonists |
| EP2611782A1 (en) | 2010-09-01 | 2013-07-10 | Arena Pharmaceuticals, Inc. | Salts of lorcaserin with optically active acids |
| KR20180118801A (ko) | 2010-09-01 | 2018-10-31 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 체중 관리에 유용한 5-ｈｔ2ｃ 작동제의 변형-방출 투여 형태 |
| KR20130101524A (ko) | 2010-09-01 | 2013-09-13 | 아레나 파마슈티칼스, 인크. | 5-ｈｔ2ｃ 아고니스트의 비-흡습성 염 |
| NZ630494A (en) | 2010-09-01 | 2016-05-27 | Arena Pharm Inc | Administration of lorcaserin to individuals with renal impairment |
| MX2015004532A (es) | 2012-10-09 | 2016-01-20 | Arena Pharm Inc | Metodo de control del peso. |
-
1967
- 1967-02-17 CH CH238667A patent/CH481110A/de not_active IP Right Cessation
- 1967-08-18 CH CH1167167A patent/CH488705A/de not_active IP Right Cessation
-
1968
- 1968-02-15 US US705612A patent/US3652543A/en not_active Expired - Lifetime
- 1968-02-16 IL IL29485A patent/IL29485A/xx unknown
- 1968-02-16 FR FR1561479D patent/FR1561479A/fr not_active Expired
- 1968-02-16 BE BE710872D patent/BE710872A/xx unknown
- 1968-02-16 SE SE2047/68A patent/SE342043B/xx unknown
- 1968-02-16 FR FR1560654D patent/FR1560654A/fr not_active Expired
- 1968-02-16 NO NO0598/68A patent/NO124369B/no unknown
- 1968-02-16 DE DE19681668915 patent/DE1668915A1/de active Pending
- 1968-02-16 NL NL6802257A patent/NL6802257A/xx unknown
- 1968-02-16 GB GB7601/68A patent/GB1221324A/en not_active Expired
- 1968-02-16 DK DK63068AA patent/DK115473B/da unknown
- 1968-02-16 ES ES350574A patent/ES350574A1/es not_active Expired
- 1968-02-16 GB GB7600/68A patent/GB1222397A/en not_active Expired
- 1968-02-16 DE DE19681695124 patent/DE1695124A1/de active Pending
- 1968-02-16 AT AT148868A patent/AT275533B/de active
Also Published As
| Publication number | Publication date |
|---|---|
| GB1222397A (en) | 1971-02-10 |
| US3652543A (en) | 1972-03-28 |
| ES350574A1 (es) | 1969-11-16 |
| GB1221324A (en) | 1971-02-03 |
| DE1695124A1 (de) | 1970-08-20 |
| FR1561479A (OSRAM) | 1969-03-28 |
| NO124369B (OSRAM) | 1972-04-10 |
| AT275533B (de) | 1969-10-27 |
| DK115473B (da) | 1969-10-13 |
| SE342043B (OSRAM) | 1972-01-24 |
| FR1560654A (OSRAM) | 1969-03-21 |
| BE710872A (OSRAM) | 1968-08-16 |
| CH481110A (de) | 1969-11-15 |
| NL6802257A (OSRAM) | 1968-08-19 |
| IL29485A (en) | 1971-07-28 |
| CH488705A (de) | 1970-04-15 |
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