ES466706A2 - Procedure to produce argininamids and their salts. (Machine-translation by Google Translate, not legally binding) - Google Patents

Procedure to produce argininamids and their salts. (Machine-translation by Google Translate, not legally binding)

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Publication number
ES466706A2
ES466706A2 ES466706A ES466706A ES466706A2 ES 466706 A2 ES466706 A2 ES 466706A2 ES 466706 A ES466706 A ES 466706A ES 466706 A ES466706 A ES 466706A ES 466706 A2 ES466706 A2 ES 466706A2
Authority
ES
Spain
Prior art keywords
group
alkyl
alkoxy
mixtures
optionally substituted
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
Application number
ES466706A
Other languages
Spanish (es)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsubishi Kasei Corp
Original Assignee
Mitsubishi Kasei Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from US05/760,672 external-priority patent/US4093712A/en
Priority claimed from US05/760,668 external-priority patent/US4073913A/en
Priority claimed from US05/760,929 external-priority patent/US4101653A/en
Priority claimed from US05/760,745 external-priority patent/US4066773A/en
Application filed by Mitsubishi Kasei Corp filed Critical Mitsubishi Kasei Corp
Publication of ES466706A2 publication Critical patent/ES466706A2/en
Expired legal-status Critical Current

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Classifications

    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Peptides Or Proteins (AREA)

Abstract

Improvements in the object of patent 454,098 for the Process for producing argininamides and their salts and, more particularly, in the processes for producing N2-arylsulfonyl-L-argininamides of the formula (I): **(See formula)** and its pharmaceutically acceptable salts, characterized in that choosing R from **(See formula)** wherein R1 is selected from the group consisting of c2-C10'alkyl C3-C10 alkenyl, C3-C10 alkynyl, C2-C10 alkoxyalkyl, C2-C10 alkylthioalkyl, C2-C10 alkylsulfinylalkyl, C3-C10alkyl-alkyl alkyl, C3-C-10, C1-C10 haloalkyl, C7-C15 aralkyl, C8-C15 alpha-carboxyalkyl, C3-C10 cycloalkyl, C4-C10 cycloalkylalkyl, furfuryl, tetrahydrofurfuryl optionally substituted with at least one C1-C5 alkyl, C1 alkoxy -C5 or its mixtures, 3-furylmethylon, tetrahydro-3-furylmethyl optionally substituted with at least one C1-C5 alkyl, to C1-C5 coxy or its mixtures, tetrahydro -2 (3 or 4) - pyranylmethyl optionally substituted with by at least one C1-C5-alkyl, C1-C5-alkoxy or mixtures thereof, 1,4-dioxa-2-cyclohexylmethyl optionally substituted with at least one C1-C5-alkyl, C1-C5-alkoxy or mixtures thereof, 2-tenyl, 3 -tenyl, tetrahydro-2-tenyl optionally substituted with at least one C1-C5 alkyl, C1-C5 alkoxy or mixtures thereof, and tetra hydro-3-tenyl; R2 is chosen from the group consisting of hydrogen, C1-C10 alkyl, C6-C10 aryl and C7-C12 aralkyl and n is an integer equal to 1, 2 or 3, **(See formula)** wherein R3 is selected from the group consisting of hydrogen, C1-C10 alkyl, C3-C10 alkenyl, C3-C10 alkynyl, C2-C10 alkoxyalkyl, C2-C10 alkylthioalkyl, C2-C10alkyl alkyl, C1-C10 hydroxyalkyl, C3-C10alkoxycarbonylalkyl, C3-C10 alkylcarbonylalkyl, C1-C10 haloalkyl, C7-C15 aralkyl, C8-C15 alpha-carboxyralkyl, C3-C10 cycloalkyl, C4C10 cycloalkylalkyl, optionally substituted by at least one C1-C5alkyl, or mixtures thereof, 3-furylmethyl, tetrahydro-3-furylmethyl optionally substituted with at least one C1-C5 alkyl, C1-C5 alkoxy or mixtures thereof, tetrahydro -2 (3 or 4) -pyranylmethyl optionally substituted with at least one C1-C5-alkyl, C1-C5-alkoxy or mixtures thereof, 1,4-dioxa-2-cyclohexy1methyl optionally substituted with at least one C1-C5-alkyl, C1-C5-alkoxy or mixtures thereof, 2-tenyl, 3-tenyl, tetrahydro-2-tenyl optionally substituted with at least one C1-C5 alkyl C1C5 alkoxy or mixtures thereof, and tetrahydro-3-tenyl; R4 is selected from the group consisting of C1-C10 alkyl, phenyl optionally substituted with at least one C1-C5 alkyl, C1-C5 alkoxy or mixtures thereof, C7-C12 aralkyl, and ring-substituted benzyl, wherein said substituent is C1-C5 alkyl or C1-C5 alkoxy; R5 is chosen from the group consisting of hydrogen, C1-C10 alkyl, C6-C10 aryl and C7-C12 aralkyl; and m is an integer equal to 0, 1 or 2 **(See formula)** where R6 is -COOR8 where R8 is selected from the group consisting of hydrogen, C1-C10 alkyl, C6-C10 aryl and C7-C12 aralkyl; each R7 is independently hydrogen, C1-C10 alkyl, phenyl, C1-C5 alkoxy, C2-C6 alkoxycarbonyl or carboxy; p is an integer from 1 to 4; R6 is substituted in position 2 or 3; R7 can be substituted in position 2, 3, 4, 5 or 6, **(See formula)** optionally substituted with at least one C1-C5 alkyl, C1-C5 alkoxy, or mixtures thereof, wherein R9 is selected from the group consisting of hydrogen, C1-C10 alkyl, C6-C10 aryl, and C7-C12 aralkyl; and r is an integer equal to 1, 2, 3 or 4, **(See formula)** wherein R10 is selected from the group consisting of hydrogen, C1-C10 alkyl, C6-C10 aryl, and C7-C12 aralkyl; Z is chosen from the group consisting of oxy, uncle, and sulfinyl; and q is an integer equal to 0 or 1, and **(See formula)** wherein R11 is selected from the group consisting of hydrogen, C1-C10 alkyl, C6-C10 aryl, and C7-C12 aralkyl; i is an integer equal to 0, 1 or 2; j is an integer equal to 0, 1 or 2; and the sum of i + j is an integer equal to 1 or 2; and choosing Ar from a phenyl or naphthyl group, either substituted with at least one substituent chosen from the group consisting of sulfoamino, carbamoyl, N, N-dialkylcarbamoyl C3-C10, N-alkylcarbamoyl C2-C6, amino, C1-C10 alkylamino, mercapto, C1-C10 alkylthio, C7-C12 aralkyl, carboxy, C2-C10 alkoxycarbonyl, C2-C10 carboxyalkyl, C1-C10 acylamino, C1-C10 hydroxyalkyl, C1-C10 haloalkyl, C1-C10 hydroxyalkoxy and optionally substituted phenyl with at least one hydroxy, C1-C5 alkoxy or mixtures thereof; a phenyl or naphthyl group, either substituted with at least one substituent chosen from the group consisting of halo, nitro, cyano, hydroxy, C1-C10 alkyl, C1-C10 alkoxy and C2-C20 dialkylamino, and at least one substituent chosen from the group consisting of sulfoamino, carbamoyl, N, N-dialkylcarbamoyl C3-C10, N-alkylcarbamoyl C2-C6, amino, C1-C10 alkylamino, mercapto, C1-C12 alkylthio, carboxy, C2-C10 alkoxycarbonyl, C2-C10 carboxyalkyl, C1-C10 acylamino, C2-C10 alkylcarbonyl hydroxyalkyl-C10 alkyl, C1-C10 haloalkyl, hydroxyalkoxy C1-C10 and phenyl optionally substituted with at least one hydroxy, C1-C5 alkoxy or mixtures thereof; an oxantrenyl or dibenzofuranyl group substituted with at least one substituent chosen from the group consisting of halo, nitro, cyano, hydroxy, dialkylamino C2-C20, sulfoamino, carbamoyl, NN-dialkylcarbamoyl C3-C10, amino, C1-C10 alkylamino, mercapto, C1-C10 alkylthio, C7-C12 aralkyl, carboxyl, C2-C10 alkoxycarbonyl, C2-C10 carboxyalkyl, C2-C10 alkylcarbonyl, C1-C10 hydroxyalkyl, C1-C10 haloalkyl, hydroxyalkoxy C1-C10, and phenyl optionally substituted with at least one hydroxy, C1-C5 alkoxy or mixtures thereof; an oxantrenyl or dibenzofuranyl group substituted with at least one substituent chosen from the group consisting of C1-C10 alkyl and C1-C10 alkoxy, and at least one substituent chosen from the group consisting of halo, nitro, cyano, hydroxy, C2-C20 dialkylamino., sulfoamino, carbamoyl, N, N-dialkylcarbamoyl C3-C10, N-alkylcarbamoyl C2-C6, amino, C1-C10 alkylamino, C7-C12 aralkyl, cnrboxyl, C2-C10 alkoxycarbonyl, carboxyalkyl C10 C1-C10 alkylamino, C2-C10alkylcarbonyl, C1-C10 hydroxyalkyl, C1-C10 haloalkyl, C1-C10 hydroxyalkoxy and phenyl optionally substituted with at least one hydroxy, C1-C5 alkoxy or mixtures thereof; a 1,2-ethylenedioxyphenyl, chromanyl, 2,3-ethylenedioxynaphthyl or xanthenyl tetrahydronaphthyl group, either substituted with at least one substituent chosen from the group consisting of halo, nitro, cyano, hydroxy, C2-C20 dialkylamino, sulfamino, carbamoyl, N, N-dialkylcarbamoyl C1-C10, N-alkylcarbamoyl C2-C6, amino, C1-C10-alkylamino, mercapto, C1-C10-alkylthio, carboxyl, C2-C10-alkoxycarbonyl, C2-C10-carboxyalkyl -C10, C2-C10 alkylcarbonyl, C1-C10 hydroxyalkyl, C1-C10 haloalkyl, C1-C10 hydroxyalkoxy, oxo and phenyl optionally substituted with at least one hydroxy, C1-C5 alkoxy or mixtures thereof; a tetrahydronaphthyl, 1,2-ethylenedioxyphenyl, chromanyl, 2,3-ethylenedioxinaphthyl or xanthenyl group, either substituted with at least one substituent chosen from the group consisting of C1-C10 alkyl and C1-C10 alkoxy, and at least one Substituent chosen from the group consisting of halo, nitro, cyano, hydroxy, dialkylamino C2-C20, sulfoamino, carbamoyl, N, N-dialkylcarbamoyl C3-C10, N-alkylcarbamoyl C2-C6, amino, C1-C10 alkylamino, mercapto, C1-alkylthio -C10, C7-C12 aralkyl, carboxyl, C2-C10 alkoxycarbonyl, C2-C10 carboxyalkyl, C1-C10 acylamino, C2-C10 alkylcarbonyl, C1-C10 hydroxyalkyl, C1-C10 hydroxyalkoxy, oxo and optionally substituted phenyl with at least one hydroxy, C1-C5 alkoxy or mixtures thereof; a naphthoquinonyl, anthryl, phenanthryl, pentalenyl, heptalenyl, azulenyl, biphenylenyl, as-indacenyl, S-indacenyl, acenaphthylenyl, phenylcarbonylphenyl, phenoxyphenyl, isobenzofuranyl, benzo (b) thienyl, isobenothylenyl, isobenzotynyl, benzyne (b) thienyl, isobenzophuranyl 1H-indazolyl, quinolyl, isoquinolyl, dtalacinyl, 1,8-naphtridinyl, quinoxalinyl, quinazolinyl, cannolinyl, carbazolyl, acridinyl, phenazinyl, fenoriacinyl, phenoxacinyl, or benzimidazolyl, either of which is unsubstituted or substituted by one or more groups formed halo, nitro, cyano, hydroxy, C1-C10 alkyl, C1-C10 alkoxy, dialkylamino C2-C20, sulfoamino, carbamoyl, N, N-dialkylcarbamoyl C3-C10, N-alkylcarbamoyl C2-C6, amino, C1-C10 alkylamino, mercapto, C1-C10 alkylthio, C7-C12 aralkyl, carboxyl, C2-C10 alkoxycarbonyl, C2-C10 carboxyalkyl, C1-C10 acylamino, C1-C10 hydroxyalkyl, C1-C10 haloalkyl, C1-C10 hydroxyalkoxy, and f enyl optionally substituted with at least one hydroxy, C1-C5 alkoxy or mixtures thereof; a C7-C12 aralkyl group, C9-C16 cycloalkylphenyl, C10-C18 cycloalkylalkylphenyl, C9-C16 cycloalkyloxyphenyl, C9-C16 cycloalkylthiophenyl, 5,6,7,8-tetrahydroantryl, 9,10-dihydrophenyl, 2,3,4,5,6,7,8-octahydrophenanthryl, indenyl, indanyl, fluoenyl, acenaphthenyl, phenylthiophenyl, isochromanyl, 2,3-dihydrobenzofuranyl, 1,3-dihydroisobenzofuranyl, thioxanthenyl, 2H-chromenyl, 3,4-dehydro- 1-isochromanyl, 4H-chromenyl, indolinyl, isoindolinyl, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinolyl, any one of which is unsubstituted or substituted with one or more groups chosen from the group consisting of halo, nitro, cyano, hydroxy, C1-C10-alkyl, C1-C10-alkoxy, any C2-C20-alkylamino, sulfoamino, carbamoyl, N, N-duyalkylcarbamoyl, C3-C10, N-C1-C10-alkylcarbamoyl, mercapto, C1-alkylthio -C10, C7-C12 aralkyl carboxyl, C2-C10 alkoxycarbonyl, C2-C10 carboxyalkyl, C1-C10 acylamino, C2-C10 alkylcarbonyl, C1-C10 hydroxyalkyl, h C1-C10 alloalkyl, C1-C10 hydroxyalkoxy, oxo and phenyl optionally substituted with at least one hydroxyl, C1-C5 alkoxy or mixtures thereof; or a phenyl group substituted with at least one substituent chosen from the group consisting of alkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkoxyalkoxy, alkoxycarbonylalkyl and alkoxycarbonylalkyoxy, said substituent containing from 3 to 7 carbon atoms and said phenyl group being optionally further substituted by at least one substituent chosen from the group consisting of methyl, ethyl, methoxy, ethoxy, hydroxy and halo they comprise removing the NC substituent from an NG-substituted N2-arylsulfonyl-L-argininamide having the formula; **(See formula)** where R and Ar are as previously defined; R'and R''are chosen from the group consisting of hydrogen and guanidino group protecting groups, and at least R' or R'' is a guanidino group protecting group, by means of acidolysis or hydrogenolysis and, if desired, hydrolyze the reaction product obtained. (Machine-translation by Google Translate, not legally binding)
ES466706A 1977-01-19 1978-01-10 Procedure to produce argininamids and their salts. (Machine-translation by Google Translate, not legally binding) Expired ES466706A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US05/760,672 US4093712A (en) 1974-11-08 1977-01-19 N2 -arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof
US05/760,668 US4073913A (en) 1974-11-08 1977-01-19 N2 -arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof
US05/760,929 US4101653A (en) 1974-11-08 1977-01-19 N2 -arylsulfonyl-argininamides and the pharmaceutically acceptable salts thereof
US05/760,745 US4066773A (en) 1974-11-08 1977-01-19 N2 -arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof

Publications (1)

Publication Number Publication Date
ES466706A2 true ES466706A2 (en) 1978-10-16

Family

ID=27505686

Family Applications (2)

Application Number Title Priority Date Filing Date
ES466706A Expired ES466706A2 (en) 1977-01-19 1978-01-10 Procedure to produce argininamids and their salts. (Machine-translation by Google Translate, not legally binding)
ES466705A Expired ES466705A2 (en) 1977-01-19 1978-01-19 Improvements in the object of the patent on procedure to produce argininamidas and its sapes. (Machine-translation by Google Translate, not legally binding)

Family Applications After (1)

Application Number Title Priority Date Filing Date
ES466705A Expired ES466705A2 (en) 1977-01-19 1978-01-19 Improvements in the object of the patent on procedure to produce argininamidas and its sapes. (Machine-translation by Google Translate, not legally binding)

Country Status (1)

Country Link
ES (2) ES466706A2 (en)

Also Published As

Publication number Publication date
ES466705A2 (en) 1979-08-16

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Effective date: 20170706