JPS631286B2 - - Google Patents
Info
- Publication number
- JPS631286B2 JPS631286B2 JP53147307A JP14730778A JPS631286B2 JP S631286 B2 JPS631286 B2 JP S631286B2 JP 53147307 A JP53147307 A JP 53147307A JP 14730778 A JP14730778 A JP 14730778A JP S631286 B2 JPS631286 B2 JP S631286B2
- Authority
- JP
- Japan
- Prior art keywords
- biphenylyl
- propionamide
- compound
- compounds
- diethylaminoethyl
- 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
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical class CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 8
- 231100000252 nontoxic Toxicity 0.000 claims description 7
- 230000003000 nontoxic effect Effects 0.000 claims description 7
- 230000002921 anti-spasmodic effect Effects 0.000 claims description 6
- 239000000812 cholinergic antagonist Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 230000000694 effects Effects 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 229940080818 propionamide Drugs 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- GXLWOFJVIBEMCS-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-2-(4-phenylphenyl)propanamide Chemical compound C1=CC(C(C)C(=O)NCCN(CC)CC)=CC=C1C1=CC=CC=C1 GXLWOFJVIBEMCS-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 4
- CURUTKGFNZGFSE-UHFFFAOYSA-N dicyclomine Chemical compound C1CCCCC1C1(C(=O)OCCN(CC)CC)CCCCC1 CURUTKGFNZGFSE-UHFFFAOYSA-N 0.000 description 4
- 229960002777 dicycloverine Drugs 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 230000001734 parasympathetic effect Effects 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229940124575 antispasmodic agent Drugs 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- -1 (biphenylyl) propionic acid chloride Chemical compound 0.000 description 2
- JALUUBQFLPUJMY-UHFFFAOYSA-N 2-(4-phenylphenyl)propanoic acid Chemical class C1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 JALUUBQFLPUJMY-UHFFFAOYSA-N 0.000 description 2
- DWDRHYMGDMNKLL-UHFFFAOYSA-N 2-(4-phenylphenyl)propanoyl chloride Chemical compound C1(=CC=CC=C1)C1=CC=C(C=C1)C(C(=O)Cl)C DWDRHYMGDMNKLL-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 206010044565 Tremor Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 230000001713 cholinergic effect Effects 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 230000003412 degenerative effect Effects 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229940102396 methyl bromide Drugs 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 210000001087 myotubule Anatomy 0.000 description 2
- RTRKPILFNHPEFH-UHFFFAOYSA-N n-[3-(diethylamino)propyl]-2-(4-phenylphenyl)propanamide Chemical compound C1=CC(C(C)C(=O)NCCCN(CC)CC)=CC=C1C1=CC=CC=C1 RTRKPILFNHPEFH-UHFFFAOYSA-N 0.000 description 2
- 210000001428 peripheral nervous system Anatomy 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 210000002460 smooth muscle Anatomy 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000018405 transmission of nerve impulse Effects 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 229930003347 Atropine Natural products 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 206010023644 Lacrimation increased Diseases 0.000 description 1
- 206010028289 Muscle atrophy Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- HOBWAPHTEJGALG-JKCMADFCSA-N [(1r,5s)-8-methyl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate;sulfate Chemical compound [O-]S([O-])(=O)=O.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1 HOBWAPHTEJGALG-JKCMADFCSA-N 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000001741 anti-phlogistic effect Effects 0.000 description 1
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
- 229960004046 apomorphine Drugs 0.000 description 1
- 229960000396 atropine Drugs 0.000 description 1
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
- 229960002028 atropine sulfate Drugs 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000036471 bradycardia Effects 0.000 description 1
- 208000006218 bradycardia Diseases 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 230000007885 bronchoconstriction Effects 0.000 description 1
- HOZOZZFCZRXYEK-GSWUYBTGSA-M butylscopolamine bromide Chemical compound [Br-].C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)CCCC)=CC=CC=C1 HOZOZZFCZRXYEK-GSWUYBTGSA-M 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 1
- 229960004484 carbachol Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 210000000232 gallbladder Anatomy 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 230000004317 lacrimation Effects 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 108010067654 nerveside Proteins 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 210000005037 parasympathetic nerve Anatomy 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 210000000578 peripheral nerve Anatomy 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 229950009846 scopolamine butylbromide Drugs 0.000 description 1
- 230000016160 smooth muscle contraction Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT964377A IT1090782B (it) | 1977-11-30 | 1977-11-30 | 2 4 bifenilil 2 dietilamino alchil propionamide suoi sali e procedimenti di fabbricazione relativi |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5490157A JPS5490157A (en) | 1979-07-17 |
| JPS631286B2 true JPS631286B2 (pt) | 1988-01-12 |
Family
ID=11132874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14730778A Granted JPS5490157A (en) | 1977-11-30 | 1978-11-30 | Novel propione amide derivative and its manufacture |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5490157A (pt) |
| BE (1) | BE872403A (pt) |
| CA (1) | CA1118446A (pt) |
| CH (1) | CH637370A5 (pt) |
| DE (1) | DE2851416A1 (pt) |
| ES (1) | ES475533A1 (pt) |
| FR (1) | FR2410641A1 (pt) |
| IT (1) | IT1090782B (pt) |
| NL (1) | NL7811698A (pt) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20012025A1 (it) * | 2001-09-28 | 2003-03-28 | Dompe Spa | Sali di ammonio quaternari di omega-amminoalchilammidi di acidi r 2-aril-propionici e composizioni farmaceutiche che li contengono |
| WO2008020270A1 (en) * | 2006-08-15 | 2008-02-21 | Techfields Biochem Co. Ltd | Positively charged water-soluble prodrugs of aryl- and heteroarylpropionic acids with very fast skin penetration rate |
| US20090221703A1 (en) | 2006-07-09 | 2009-09-03 | Chongxi Yu | High penetration composition and uses thereof |
| US20090238763A1 (en) | 2006-07-09 | 2009-09-24 | Chongxi Yu | High penetration compositions and uses thereof |
| EP2990402A1 (en) * | 2006-08-08 | 2016-03-02 | Techfields Biochem Co. Ltd | Positively charged water-soluble prodrugs of aryl- and heteroarylacetic acids with very fast skin penetration rate |
| AU2013206218B2 (en) * | 2006-08-15 | 2016-06-30 | Techfields Biochem Co. Ltd | Positively charged water-soluble prodrugs of aryl- and heteroarylpropionic acids with very fast skin penetration rate |
| CN101687792B (zh) | 2007-06-04 | 2016-03-02 | 于崇曦 | 具有快速皮肤和生物膜穿透速度的非甾体抗炎药的前药及其医药用途 |
| RU2630577C2 (ru) | 2008-12-04 | 2017-09-11 | Чунси ЮЙ | Композиции интенсивного проникновения и их применение |
| JP5940036B2 (ja) * | 2013-10-08 | 2016-06-29 | テックフィールズ バイオケム カンパニー リミテッド | 非常に速い皮膚透過率を有するアリール−及びヘテロアリールプロピオン酸の正荷電水溶性プロドラッグ |
| JP6290947B2 (ja) * | 2016-02-05 | 2018-03-07 | テックフィールズ バイオケム カンパニー リミテッド | 非常に速い皮膚透過率を有するアリール−及びヘテロアリールプロピオン酸の正荷電水溶性プロドラッグ |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1593024A (pt) * | 1968-09-18 | 1970-05-25 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1584547A (pt) * | 1968-06-05 | 1969-12-26 | ||
| FR2119846A1 (en) * | 1970-12-28 | 1972-08-11 | Choay Sa | N,n-diethylaminoethylamide of para isobutyl phenylacetic - acid - antiinflammatory and analgesic |
| US4145435A (en) * | 1976-11-12 | 1979-03-20 | The Upjohn Company | 2-aminocycloaliphatic amide compounds |
-
1977
- 1977-11-30 IT IT964377A patent/IT1090782B/it active
-
1978
- 1978-11-28 CH CH1216178A patent/CH637370A5/it not_active IP Right Cessation
- 1978-11-28 DE DE19782851416 patent/DE2851416A1/de active Granted
- 1978-11-29 ES ES475533A patent/ES475533A1/es not_active Expired
- 1978-11-29 NL NL7811698A patent/NL7811698A/xx not_active Application Discontinuation
- 1978-11-30 FR FR7833889A patent/FR2410641A1/fr active Granted
- 1978-11-30 JP JP14730778A patent/JPS5490157A/ja active Granted
- 1978-11-30 BE BE192036A patent/BE872403A/xx not_active IP Right Cessation
- 1978-11-30 CA CA000317175A patent/CA1118446A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1593024A (pt) * | 1968-09-18 | 1970-05-25 |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1090782B (it) | 1985-06-26 |
| ES475533A1 (es) | 1980-01-16 |
| CA1118446A (en) | 1982-02-16 |
| FR2410641A1 (fr) | 1979-06-29 |
| NL7811698A (nl) | 1979-06-01 |
| DE2851416A1 (de) | 1979-05-31 |
| CH637370A5 (en) | 1983-07-29 |
| JPS5490157A (en) | 1979-07-17 |
| FR2410641B1 (pt) | 1983-04-15 |
| DE2851416C2 (pt) | 1989-02-23 |
| BE872403A (fr) | 1979-03-16 |
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