US3839330A - 2-alkoxy-4,5-azimidobenzamides - Google Patents

2-alkoxy-4,5-azimidobenzamides Download PDF

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Publication number
US3839330A
US3839330A US00117836A US11783671A US3839330A US 3839330 A US3839330 A US 3839330A US 00117836 A US00117836 A US 00117836A US 11783671 A US11783671 A US 11783671A US 3839330 A US3839330 A US 3839330A
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United States
Prior art keywords
methoxy
ethyl
azimidobenzamide
pyrrolidylmethyl
compound
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Expired - Lifetime
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US00117836A
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English (en)
Inventor
M Thominet
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SOC D ETUDE SCIENTIFIGUES ET INDUSTRIELLES de l ILE DE FR FR
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Ile De France
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Publication date
Priority to FR118161A priority Critical patent/FR6787M/fr
Priority to FR127131A priority patent/FR1572168A/fr
Priority to OA53344A priority patent/OA03879A/xx
Priority to BE719048D priority patent/BE719048A/xx
Priority to DE1795653A priority patent/DE1795653C3/de
Priority to DE19681795110 priority patent/DE1795110C/de
Priority to CH1221268A priority patent/CH496007A/fr
Priority to GB1232836D priority patent/GB1232836A/en
Application filed by Ile De France filed Critical Ile De France
Priority to US00117836A priority patent/US3839330A/en
Priority to NL727212623A priority patent/NL151707B/xx
Application granted granted Critical
Publication of US3839330A publication Critical patent/US3839330A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles

Definitions

  • azimidobenzamides of this invention are useful in the control of emesis.
  • Such azimidobenzamides administeredto mammals in a dosage of 250 p, mg. (as the base) per kilogram of body weight effectuate 100 percent protection against emesis.
  • n 1 or 2
  • B is alkyl or alkenyl of one to five carbon atoms
  • A is a monovalent radical having either of the formulas:
  • R is an alkyl group of one to five carbon atoms
  • R. and R are hydrogen or 1 or 2 alkyl radicals of one to five carbon atoms or each is linked together through at least three carbon atoms to form with the nitrogen to which they are attached a heterocyclic radical with or without oxygen, sulfur or an additional nitrogen atom.
  • the nitrogen atom has attached thereto hydrogen or an alkyl radical of one to five carbon atoms.
  • Examples of monovalent radicals when formula (2) comprises a heterocyclic radical are pyrrolidinyl, piperidinyl, imidazolidinyl, piperazino and thiazolidinyl.
  • Examples of monovalent radicals of formula (3) are pyrrolidinyl and piperidinyl.
  • the pharmaceutically acceptable salts of the bases described herein may be acid addition salts or quaternary ammonium salts.
  • acid addition salts are those of the bases and mineral acids, such as hydrochloric acid, hydrobromic acid or phosphoric acid or those of bases and organic acids, such as citric acid, tartaric acid, lactic acid or acetic acid.
  • quaternary ammonium salts are those obtained by reacting the bases described herein with aliphatic or aromatic alkylating agents such as methyl chloride, methyl bromide, dimethyl sulfate, or methyl p-toluenesulfonate.
  • compositions of this invention are useful as antiemetics, antispasmodics and analgesics.
  • the compound of the invention may be the dextro stereo isomer alone, the levo stereo isomer alone or mixtures of both stereo isomers, such as a racemic mixture of both stereo isomers. If an inactive meso form exists, this invention contemplates such meso form with or without either or both the dextro or levo stereo isomers.
  • the compounds of this invention are produced by reacting in an acid medium, such as a mineral acid, a nitrite with a 2-alkoxy-4,5-diaminobenzamide having the formula:
  • nitrite may be an organic or inorganic nitrite.
  • Amyl nitrite is an example of an organic nitrite, while a metallic nitrite, such as an alkali metal nitrite (e.g. sodium or potassium nitrite) is an example of an inorganic nitrite.
  • an alkali metal nitrite e.g. sodium or potassium nitrite
  • Stage B N-(diethylaminoethyl)-2-methoxy-4-amino- 5-nitrobenzamidev
  • 182 g. (0.68 mol) of methyl 2-methoxy-4-acetamino-S-nitrobenzoate and 600 ml. of glycol and then 236 g. (0.68 mol X 3) of diethylaminoethylamine are added.
  • the reaction is slightly exothermic (T 31 C.).
  • a suspension is obtained which is heated at 55 C. and at the end of 3/4 of an hour, dissolution is complete and U2 hour later the formation of an abundant preprecipitate is observed.
  • reaction mixture is maintained for hours at 55 C. All is then soluble in dilute acetic acid.
  • 2-methoxy-4-acetamino-5- mixture is then heated to 50 C. and 390 ml. of hydrochloric acid are introduced in portions.
  • the reaction is strongly exothermic.
  • the temperature reaches 80 to 100 C. It is cooled if necessary.
  • azimidobenzamide Into a 2 liter flask equipped with an agitator, a thermometer and a dropping funnel, there are placed 116 g. (0.284 mol) of dihydrochloride of N- (diethylaminoethyl)-2-methoxy-4,5- diaminobenzamide, 568 ml. of water and 28 ml. of concentrated hydrochloric acid. The mixture is heated at about 40-45 C. to dissolve the mixture. It is cooled to C. and 20 g. (0.284 mol) of sodium nitrate in water are poured drop by drop from the dropping funnel. When the addition is completed, agitation is continued for 1 hour and the temperature allowed to rise to 20 C.
  • Stage B N-(l-ethyl-2-pyrrolidylmethyl)-2-methoxy- 4-amino-5-nitro benzamide
  • 140 g. 0.52 mol
  • methyl 2-methoxy-4-acetamino-S-nitro benzoate 500 ml. of glycol
  • 201 g. 0.52 mol X 3
  • a thick yellow suspension is obtained which is heated to 55C. and maintained at 55 C. for 120 hours. No apparent transformation of the initial precipitate is observed but at the end of the reaction a sample showed complete solubility in dilute acetic acid.
  • the organic solution is decanted and the aqueous solution is extracted once with 200 ml. of methylene chloride and once with 100 ml.
  • Stage D N-(1-ethyl-2-pyrrolidylmethyl)-2-methoxy- 4,5-azimidobenzamide
  • a 2 liter flask equipped with an agitator, a thermometer and a dropping funnel there are introduced 112 g. (0.278 mol) of hydrochloride of N-(l-ethyl-Z- pyrrolidylmethyl)-2-methoxy-4,5-diamino benzamide, 580 ml. of water and 28 ml. of concentrated hydrochlo ric acid.
  • the mixture is heated to 40-45 C. to achieve complete dissolution and then cooled to 0 C. 19 G. of sodium nitrite dissolved in 28 ml.
  • Example I1 To produce N-(1-ethyl-2-pyrrolidylmethyl)-2- vinyloxy-4,5 azimidobenzamide, Example I1 is followed except that the addition of 146 g. (0.52 mol) of 2- vinyloxy-4-acetamino-S-nitromethyl benzoate is employed instead of the g. of 2-methoxy-4-acetamino- 5-nitromethyl benzoate.
  • Example II To produce N-(1-ethyl-2-imidazolidylmethyl)-2- methoxy-4,5-azimidobenzamide, Example II is followed except that the addition of 202 g. (0.52 mol X 3) of l-ethyl-2-aminomethylimidazolidine is employed instead of the 201 g. of 1-ethyl-2-aminomethylpyrrolidine.
  • Example II To produce N-(3-ethyl-2-thiazolidylmethyl)-2- methoxy-4,5-azimidobenzamide, Example II is followed except that the addition of 229 g. (0.52 mol X 3) of 3-ethyl-2-aminomethylthiazolidine is employed instead of the 201 g. of 1-ethyl-2-aminomethyl pyrrolidine.
  • Stage A is similar to that described in Example I.
  • Stage B Dextro N-(1-ethyl-2-pyrrolidylmethyl)-2- methoxy-4-amino-5-nitrobenzamide
  • 80 g. (0.3 mol) of methyl 2-methoxy-4-acetamino-5-nitrobenzoate 285 ml. of glycol
  • 84 g. (2.2 X 0.3 mol) of dextro 1- ethyl-2-amino-methylpyrrolidine there are introduced 80 g. (0.3 mol) of methyl 2-methoxy-4-acetamino-5-nitrobenzoate, 285 ml. of glycol and 84 g. (2.2 X 0.3 mol) of dextro 1- ethyl-2-amino-methylpyrrolidine.
  • a yellow suspension is obtained which is heated at 55 C. and maintained at that temperature for 216 hours.
  • Stage B N-(ethyl-propylaminoethyl)-2-methoxy-4- amino-5-nitrobenzamide
  • a 2 liter flask equipped with an agitator and a thermometer there are introduced 188 g. (0.7 mol) of methyl 2-methoxy-4-acetamino-5-nitrobenzoate and 700 ml. of glycol, and then 273 g. (0.7 mol X 3) of ethyl-propylethylene diamine are added.
  • the suspension obtained is heated at 55 C. and that temperature is maintained for 72 hours.
  • the ester dissolves partially at the beginning of the reaction andthe benzamide formed begins to precipitate. At the end of the reaction, there is total solubility.
  • Stage D N-(ethyhpropylaminoethyl)-2-methoxy- 4,5-azimidobenzamide
  • 106 g. (0.258 mol) of dihydrochloride-of N-(ethylpropylaminoethyl )-2-methoxy-4,5-diaminobenzamide 516 ml. of water and 26 ml. of concentrated hydrochloric acid. It is heated to dissolve the mixture. It is then cooled at C. and 18 g. (0.258 mol) of sodium nitrite dissolved in 20 ml. of water is poured drop by drop from the dropping funnel. When the addition is completed, the mixture is maintained under agitation at 0 C. for 1 hour, and then allowed to return to room temperature.
  • N- (piperidinoethyl)-2-methoxy-4,5-azimidobenzamide LD in mg/kg of composition in base state COMPOSITIONS by intraintraperisubcutamouth venously toneally neously N-(diethylaminoethyl) I500 l43-l46 387-400 600-576 -2-methoxy-4,5- (30% azimidobenzamide mortality) N-( l -ethyl-2-pyrl5 17 69 2 l 4-2l6 330-32] rolidylmethyl)-2- methoxy-4,5-azimidobenzamide Dextro-N-( l-ethyl-2- 84-85 248 339 pyrrolidylmethyl)-2- methoxy-4,5-azimidobenzamide Levo-N-(l-ethyl-2- 83-84 207 243 pyrrolidylmethyh- 2-methoxy-4,5- azimidobenzamide and
  • the solid residue is recov ered with 300 ml. of boiling ethanol.
  • the remaining sodium chloride is filtered with heat.
  • the hydrochloride of N-(ethyl-propylaminoethyl)-2-methoxy-4,5- azimidobenzamide crystallizes. It is dried and washed with alcohol. It is a white solid (mp. 155 C.).
  • compositions of this invention have the interesting pharmacological property of being anti-cataleptic.
  • the cataleptic activity of the product showed the following results: (results measured at the maximum of the effect, such as after 300 to 360 minutes) azimidobenzamide
  • the experimental results were clinically confirmed, the products being administered in the form of tablets or ampules of a pharmaceutically acceptable salt.
  • compositions of this invention can be administered in the form of a pharmaceutically acceptable salt in coated pills, injectable ampules or aerosols, suppositories, granulated saccharine or sweetened syrup. 7
  • n 1 when A is a heterocyclic radical or 2 when A is a non-heterocyclic radical; B is methyl; and A is:
  • R is alkyl of one to five carbon atoms
  • R and R are ethyl or propyl or pharmaceutically acceptable salts thereof.
  • a compound of claim 1 which is a dextro isomer.
  • a compound of claim 1 which is iodomethylate of N-(diethylaminoethyl )-2-methoxy-4,5- azimidobenzamide.
  • a compound of claim 1 which is N-(1-ethyl-2- imidazolidylmethyl)-2-methoxy-4,5- azimidobenzamide.
  • a compound of claim 1 which is N-(3-ethyl-2- thiazolidylmethyl)-2-methoxy-4,5-azimidobenzamide.
  • a compound of claim 1 which is N-(4-ethyl-2- morpholinylmethyl)-2-methoxy-4,5- azimidobenzamide.
  • a compound of claim 1 which is N-(l-ethyl-2- piperazinylmethyl)-2-methoxy-4,5-azimidobenzamide.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pyrrole Compounds (AREA)
US00117836A 1967-08-17 1971-02-22 2-alkoxy-4,5-azimidobenzamides Expired - Lifetime US3839330A (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
FR118161A FR6787M (en, 2012) 1967-08-17 1967-08-17
FR127131A FR1572168A (en, 2012) 1967-08-17 1967-11-06
OA53344A OA03879A (fr) 1967-08-17 1968-08-05 Procédé de préparation de 2-alcoxy-4,5-azimido benzamides.
BE719048D BE719048A (en, 2012) 1967-08-17 1968-08-05
DE1795653A DE1795653C3 (de) 1967-08-17 1968-08-12 Verfahren zur Herstellung von 2-Methoxy-4,5-azimidobenzamiden
DE19681795110 DE1795110C (de) 1967-08-17 1968-08-12 N Substituierte 2 Methoxy 4,5 azimidobenzamide
CH1221268A CH496007A (fr) 1967-08-17 1968-08-14 Procédé de préparation des 2-alcoxy-4,5-azimido benzamides
GB1232836D GB1232836A (en, 2012) 1967-08-17 1968-08-16
US00117836A US3839330A (en) 1967-08-17 1971-02-22 2-alkoxy-4,5-azimidobenzamides
NL727212623A NL151707B (nl) 1967-08-17 1972-09-18 Werkwijze voor het bereiden van anti-emetisch werkzame farmaceutische preparaten, alsmede van anti-emetisch werkzame verbindingen.

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR118161A FR6787M (en, 2012) 1967-08-17 1967-08-17
FR127131 1967-11-06
US75173768A 1968-08-12 1968-08-12
US00117836A US3839330A (en) 1967-08-17 1971-02-22 2-alkoxy-4,5-azimidobenzamides

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US00117836A Expired - Lifetime US3839330A (en) 1967-08-17 1971-02-22 2-alkoxy-4,5-azimidobenzamides

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BE (1) BE719048A (en, 2012)
CH (1) CH496007A (en, 2012)
DE (1) DE1795653C3 (en, 2012)
FR (2) FR6787M (en, 2012)
GB (1) GB1232836A (en, 2012)
OA (1) OA03879A (en, 2012)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4039672A (en) * 1975-01-11 1977-08-02 Societe D'etudes Scientifiques Et Industrielles De L'ile-De-France N-(1'-allypyrrolidinyl 2'-methyl) 2-methoxy 4,5-azimido benzamide and its pharmaceutically acceptable salts
FR2440946A2 (fr) * 1978-01-20 1980-06-06 Ile De France Nouveaux benzamides heterocycliques substitues, leurs procedes de preparation et leur application comme modificateurs du comportement
US4255580A (en) * 1976-08-04 1981-03-10 Siociete D'etudes Scientifiques Et Industrielles De L'ile-De-France Substituted 2,3-alkylene bis (oxy) benzamides and derivatives
US4306072A (en) * 1976-08-04 1981-12-15 Societe D'etudes Scientifiques Et Industrielles De L'ile Substituted 2,3-alkylene bis (oxy)-4,5 (or 5,6) azimido benzamides and derivatives thereof
FR2574795A1 (fr) * 1984-12-18 1986-06-20 Ile De France Nouveau procede industriel de synthese du n-((1'-allyl 2'-pyrrolidinyl) methyl) 2-methoxy 4,5-azimido benzamide
US5610265A (en) * 1996-02-02 1997-03-11 The United States Of America As Represented By The Secretary Of The Air Force Armomatic polyimides derived from 2-(N-benzoylimino)-4,4-diaminobiphenyl

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2297041A1 (fr) * 1975-01-11 1976-08-06 Ile De France N-(1'-allylpyrrolidinyl 2'methyl)2-methoxy 4,5-azimido benzamide, ses derives et ses procedes de preparation
FR2699533A1 (fr) * 1992-12-21 1994-06-24 Mouhtaram Mohamed Dérivés de N-((1,4-dialkyl-6-arylpipérazine-2-yl)méthyl)benzamides. (Isomères cis et trans) Propriétés pharmacologiques et applications.

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4039672A (en) * 1975-01-11 1977-08-02 Societe D'etudes Scientifiques Et Industrielles De L'ile-De-France N-(1'-allypyrrolidinyl 2'-methyl) 2-methoxy 4,5-azimido benzamide and its pharmaceutically acceptable salts
US4255580A (en) * 1976-08-04 1981-03-10 Siociete D'etudes Scientifiques Et Industrielles De L'ile-De-France Substituted 2,3-alkylene bis (oxy) benzamides and derivatives
US4306072A (en) * 1976-08-04 1981-12-15 Societe D'etudes Scientifiques Et Industrielles De L'ile Substituted 2,3-alkylene bis (oxy)-4,5 (or 5,6) azimido benzamides and derivatives thereof
FR2440946A2 (fr) * 1978-01-20 1980-06-06 Ile De France Nouveaux benzamides heterocycliques substitues, leurs procedes de preparation et leur application comme modificateurs du comportement
US4673686A (en) * 1978-01-20 1987-06-16 Societe D'etudes Scientifiques Et Industrielle De L'ile De France New substituted heterocyclic benzamides, methods of preparing them and their application as behavior modifiers
DK157008B (da) * 1978-01-20 1989-10-30 Ile De France Analogifremgangsmaade til fremstilling af n-pyrrolidinyl- eller n-pyrrolidinylmethylsubstituerede benzamider samt mellemprodukter til brug ved fremstillingen
FR2574795A1 (fr) * 1984-12-18 1986-06-20 Ile De France Nouveau procede industriel de synthese du n-((1'-allyl 2'-pyrrolidinyl) methyl) 2-methoxy 4,5-azimido benzamide
EP0190524A1 (fr) * 1984-12-18 1986-08-13 Societe D'etudes Scientifiques Et Industrielles De L'ile-De-France Nouveau procédé industriel de synthèse du N-[(1'-allyl 2'-pyrrolidinyl) méthyl] 2-méthoxy 4,5-azimido benzamide
US4804765A (en) * 1984-12-18 1989-02-14 Societe D'etudes Scientifiques Et Industrielles De L'ile-D-France Process for synthesizing N-[(1'-allyl-2'pyrrolidinyl) methyl]2-methoxy-4,5-azimidobenzamide
US5610265A (en) * 1996-02-02 1997-03-11 The United States Of America As Represented By The Secretary Of The Air Force Armomatic polyimides derived from 2-(N-benzoylimino)-4,4-diaminobiphenyl

Also Published As

Publication number Publication date
DE1795653C3 (de) 1975-06-05
DE1795653B2 (de) 1974-10-24
FR6787M (en, 2012) 1969-03-17
CH496007A (fr) 1970-09-15
BE719048A (en, 2012) 1969-02-05
GB1232836A (en, 2012) 1971-05-19
OA03879A (fr) 1975-08-14
DE1795110B2 (de) 1973-01-18
DE1795653A1 (de) 1973-02-08
DE1795110A1 (de) 1972-03-30
FR1572168A (en, 2012) 1969-06-27

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