PL91770B1 - Method of producing alkanolamine derivatives[cs181211b2] - Google Patents

Method of producing alkanolamine derivatives[cs181211b2] Download PDF

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PL91770B1
PL91770B1 PL1971174904A PL17490471A PL91770B1 PL 91770 B1 PL91770 B1 PL 91770B1 PL 1971174904 A PL1971174904 A PL 1971174904A PL 17490471 A PL17490471 A PL 17490471A PL 91770 B1 PL91770 B1 PL 91770B1
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isopropyl
radical
carbon atoms
isopropyl isopropyl
general formula
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PL1971174904A
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Imperial Chemical Industries Limited Te Londen
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
    • Y—GENERAL 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Cpds (I) their salts esters and aldehyde condensation products where R' is H, alkyl(opt. substd by OH, aryl or aryloxy) cycloalkyl or alkenyl, R2 is H and R3 is H, alkyl hydroxy alkyl, cycloalkyl, alkoxy alkyl, alkenyl or aralkyl or NR2R3 is a heterocyclic radical; R4 is H, halogen alkyl, alkenyl, OH, alkylthio, alkoxy, alkenyloxy, aralkoxy, or haloalkyl; R5 is H or alkyl and A is alkylene are prepd by standard methods for forming basic hydroxy ethers or by methods where the ether gp R2R3NCO-A-O- is formed. Medicaments may be in forms for oral or parenteral administration or may be aerosols and may opt. contain other drugs e.g. sedatives vasodilators, duiretics, hypotensives, hypocardiac depressants anti-parkinsonism agents cardiotonics and bronchodilators. [FR2100689A1]

Claims (2)

1. Zastrzezenia patentowe 1. Sposób wytwarzania nowych racemicznych lub optycznie czynnych pochodnych alkanoloaminy o wzo¬ rze ogólnym 1, w którym R1 , oznacza atom wodoru, rodnik alkilowy zawierajacy do 6 atomów wegla, ewen¬ tualnie podstawiony jednym lub kilkoma podstawnikami, takimi jak grupa wodorotlenowa, rodnik fenylowy lub fenoksylowy, albo R1 oznacza rodnik cykloalkilowy lub alkenylowy, kazdy zawierajacy do 6 atomów wegla, R2 oznacza atom wodoru lub rodnik alkilowy do 6 atomów wegla, R3 oznacza atom wodoru, rodnik alkilowy, hydroksyalki Iowy lub alkoksyalkilowy, kazdy zawierajacy do 10 atomów wegla, albo rodnik cykloalkiowy lub alkenylowy, kazdy do 6 atomów wegla, albo rodnik aralkilowy do 12 atomów wegla, albo R2 i R3 razem z przyleglym atomem azotu tworza calkowicie nasycony 5- lub 6-czlonowy rodnik heterocykliczny, R4 oznacza atom wodoru lub chlorowca, albo rodnik alkilowy, alkenylowy, alkilotiolowy, alkoksylowy, alkenyloksylowy, lub chlorowcoalkilowy, kazdy zawierajacy do 6 atomów wegla, albo rodnik aralkoksylowy do 10 atomów wegla, albo grupe wodorotlenowa, Rs oznacza atom wodoru lub. rodnik alkilowy do 6 atomów wegla, zas A oznacza prosty lub rozgaleziony lancuch alkilenowy zawierajacy do 4 atomów wegla, ewentualnie w postaci soli addy¬ cyjnych tych zwiazków z kwasami, znamienny tym, ze reaktywna pochodna kwasu o wzorze ogólnym 5, taka jak halogenek, bezwodnik lub ester, albo sam kwas w obecnosci karbodwuimidu, przy czym we wzorze 5 R1, R4, R5 i A maja wyzej podane znaczenia, a R7 i R8, jednakowe lub rózne ; niezaleznie od siebie oznaczaja atom wodoru lub grupe ochronna, dajaca siie usunac hydrolitycznie lub hydrogenolitycznie, poddaje sie reakcji z amina o wzorze ogólnym R2R3NH, w którym R2 i R3 maja wyzej podane znaczenia, po czym, jesli jeden lub obydwa symbole R7 i R8 oznaczaja grupy ochronne, to jedna lub obydwie grupy ochronne usuwa sie i otrzy¬ mana racemiczna pochodna alkanoloaminy ewentualnie rozdziela sie w znany sposób na jej enancjomorficzne postacie optycznie czynne i racemiczna lubboptycznie czynna pochodna alkanoloaminy ewentualnie przepro¬ wadza sie w sól addycyjna z kwasem. 2. Sposób wedlug zastrz. 1, znamienny tym, ze w celu wytworzenia zwiazków o wzorze ogólnym 2, w którym R1 oznacza atom wodoru, albo rodnik alkilowy zawierajacy do 6 atomów wegla, ewentualnie6 91 770 podstawiony jednym podstawnikiem takim, jak grupa wodorotlenowa, rodnik fenyIowy lub'fenoksylowy lub R1 oznacza rodnik cykloalkilowy, zawierajacy do 6 atomów wegla, R2 oznacza atom wodoru lub rodnik alkilowy do 6 atomów wegla, R3 oznacza atom wodoru albo rodnik alkilowy, hydroksyalkilowy lub alfcoksyalkilowy, kazdy zawierajacy do 10 atomów wegla, albo rodnik cykloalkilowy lub alkenylowy, kazdy zawierajacy do 6 atomów wegla, albo rodnik aralkilowy do 12 atomów wegla, R4 oznacza atom wodoru lub chlorowca, albo rodnik alkilowy, alkenylowy, alkilotiolowy, al koksyIowy, alkenyloksylowy lub chlorowcoalkilowy, kazdy zawierajacy do 6 atomów wegla, albo rodnik aralkoksylowy do 10 atomów wegla, albo grupe wodorotlenowa, zas A oznacza rodnik metylenowy, etylenowy lub trój metylenowy, oraz soli addycyjnych tych zwiazków z kwasami, poddaje sie reakcji reaktywna pochodna kwasu o wzorze ogólnymi 1, w którym R1, R4 i A maja wyzej podane znaczenia, z amina o wzorze ogólnym R2 R3 NH, w którym R2 i R3 maja wyzej podane znaczenia. 3. Sposób wedlug zasfz. 1, znamienny tym, ze w celu wytworzenia zwiazków o wzorze ogólnym 4, w którym R1 oznacza rodnik izopropylowy, lll-rzed.butylowy lub 2-hydroksy-1,1-dwumetyloetylowy, R3 oznacza atom wodoru albo rodnik alkilowy, hydroksyal ki Iowy, alkoksyalkilowy, alkenylowy lub cykloalkilowy, kazdy zawierajacy do 6 atomów wegla, R4 oznacza atom wodoru, grupe wodorotlenowa, albo rodnik alkilowy do 6 atomów wegla, oraz soli addycyjnych tych zwiazków z kwasami, poddaje sie reakcji reaktywna pochodna kwasu o wzorze ogólnym 12, w którym R1 i R4 maja wyzej podane znaczenia, z amina o wzorze ogólnym R3NH2, w którym R3 ma wyzej podane znaczenia. 4. Sposób wedlug zastrz. 1, znamienny tym, ze jako zwiazki wyjsciowe stosuje sie reaktywna pochodna kwasu o wzorze ogólnym 10 i amine o wzorze ogólnym R2 R3NH, w których to wzorach R1 oznacza rodnik lll-rzed.butylowy, R3 oznacza rodnik metylowy, R4, Rs, R7 i R8 oznaczaja atomy wodoru, a R2 ma znaczenie, jak okreslono w zastrz. 1.91 770 Tablica I Zwiazek o ogólnym wzorze 3 R1 izopropyl Ml-rzed.butyl izopropyl izopropyl izopropyl izopropyl izopropyl izopropyl izopropyl izopropyl izopropyl izopropyl izopropyl izopropyl izopropyl Ml-rzed.butyl izopropyl izopropyl izopropyl R3 H H H H H H H izopropyl n-butyl ll-rzed.butyl Ml-rzed.butyl n-heksyl izoheksyl n-heptyl allil allil cyklopentyl cykloheksyl benzyl R4 H H metyl n-propyl allil Br metoksy H H H H H H H H H H H H Temperatura topnienia °C 123-125 88- 90 146-148 141-143 121-123 159-161 125-128 108-109 75- 78 98-100 90- 92 92- 94 * 80- 83 90- 92 112-114 78- 80 101-103 111-114 102-104 Tablica II Zwiazek o ogólnym wzorze 7 Temperatura topnienia °c izopropyl H 107-110 Tablica III Zwiazek o ogólnym wzorze 8 izopropyl Ml-rzed.butyl H metyl n-propyl izobutyl ll-rzed.buty I Ml-rzed.butyl n-heksyl R1 izopropyl izopropyl R1 metyl R3 izopropyl Ta Zwiazek o H H metyl metyl metyl metyl metyl metyl metyl R3 Temperatura topni b 1 i ca 1 °C 62- 66 97-100 IV ogólnym wzorze 4 H H H H H H H H H R4 enia / Temperatura topniennia °C 108-109 (olej) 88-90 97-100 114-115 117 98-100 96-97 8791770 1 allil 2-hydroksy-11,dwumetyloetyl 2-(3,4-dwumetoksyfenoksy—etyl izopropyl izopropyl izopropyl izopropyl izopropyl izopropyl lll-rzed.butyl izopropyl lll-rzed.butyl izopropyl izopropyl izopropyl lll-rzed.butyl 2-hydroksy-1,1 -dwumetyloety I izopropyl izopropyl izopropyl izopropyl izopropyl izopropyl lll-rzed.butyl R1 R2 2 metyl metyl metyl metyl metyl metyl metyl metyl etyl etyl n-propyl n-propyl izopropyl n-butyl allil allil allil benzyl cyklopentyl cykloheksyl |3-hydroksyetyl |3-metoksyetyl 7-hyaroksypropyl 7-hydroksypropyl Tablica V 3 H H H metyl metoksy Br OH benzyloksy H H H H H H H H H H H H H H H H Zwiazek o ogólnym wzorze 9 R3 R5 A 4 92-93 98-101 (olej) 101-103 80^82 130-132 104-106 111-115 97-98 chlorowodorek 152 89-90 (olej) 89-94 83-84 86 (olej) (olej) 84-86 72-74 92-94 79-81 78^80 52-54 64 Temperatura topnienia °c izopropyl izopropyl izopropyl izopropyl lll-rzed.butyl etyl pentametyl H H H etyl metyl metyl metyl H H H metyl metyl CH2- -CH2- -CH(CH3)- CH2- -CH2- 55-58 wodorbszczawian 98-100 102-105 chlorowodorek 184-186 chlorowodorek 177-17991770 H02-C-A-0 ORT ^ ^yOCHgCHOHCHR^NHR' \zfc/ R4 Wzór 3 H02C-A-0 OCH1. Claims 1. A method for the preparation of new racemic or optically active alkanolamine derivatives of general formula I, wherein R1 is a hydrogen atom, an alkyl radical of up to 6 carbon atoms, optionally substituted with one or more substituents, such as a hydroxyl, phenyl or phenoxy radical, or R1 is a cycloalkyl or alkenyl radical, each containing up to 6 carbon atoms, R2 is a hydrogen atom or an alkyl radical of up to 6 carbon atoms, R3 is a hydrogen atom, an alkyl radical, hydroxyalkyl or an alkoxyalkyl radical, each containing up to 10 carbon atoms, or a cycloalkyl or alkenyl radical, up to 6 carbon atoms each, or an aralkyl radical of up to 12 carbon atoms, or R2 and R3 together with the adjacent nitrogen atom form a fully saturated 5- or 6-membered heterocyclic radical, R4 is hydrogen or a halogen or an alkyl, alkenyl, alkylthio, alkoxy, alkenyloxy or haloalkyl radical, each containing up to 6 carbon atoms, or an aralkoxy radical up to 10 carbon atoms or a hydroxyl group, Rs is hydrogen or. an alkyl radical of up to 6 carbon atoms, and A represents a straight or branched alkylene chain containing up to 4 carbon atoms, optionally in the form of addition salts of these compounds with acids, characterized in that a reactive derivative of the acid of the general formula V, such as a halide, an anhydride or an ester or the acid itself in the presence of a carbodiimide, wherein R1, R4, R5 and A are as defined above and R7 and R8 are identical or different in formula; independently of each other denote a hydrogen atom or a protecting group that can be removed hydrolytically or hydrogenolytically, is reacted with an amine of the general formula R2R3NH, in which R2 and R3 have the above meanings, then, if one or both of the symbols R7 and R8 stand for groups protecting, one or both of the protecting groups are removed and the resulting racemic alkanolamine derivative is optionally resolved in known manner into its optically active enantiomorphic forms and the racemic or optically active alkanolamine derivative is optionally converted into an acid addition salt. 2. The method according to p. The process of claim 1, characterized in that for the preparation of compounds of general formula 2 in which R 1 is a hydrogen atom, or an alkyl radical of up to 6 carbon atoms, optionally substituted with one substituent, such as a hydroxyl group, a phenylic or a phenoxy radical, or R 1. is a cycloalkyl radical of up to 6 carbon atoms, R2 is a hydrogen atom or an alkyl radical of up to 6 carbon atoms, R3 is a hydrogen atom or an alkyl, hydroxyalkyl or alpha-oxyalkyl radical, each with up to 10 carbon atoms, or a cycloalkyl or alkenyl radical, each containing up to 6 carbon atoms or an aralkyl radical up to 12 carbon atoms, R4 is hydrogen or halogen, or an alkyl, alkenyl, alkylthio, alkoxy, alkenyloxy or haloalkyl radical, each with up to 6 carbon atoms, or an aralkoxy radical with up to 10 carbon atoms, or a hydroxyl group, and A represents a methylene, ethylene or triethylene radical, and acid addition salts of these compounds ami, a reactive derivative of the acid of the general formula I in which R1, R4 and A are as defined above is reacted with an amine of the general formula R2 R3 NH in which R2 and R3 are as defined above. 3. The way according to zasfz. The process of claim 1, characterized in that to prepare compounds of general formula 4 in which R 1 is an isopropyl, tertiary butyl or 2-hydroxy-1,1-dimethylethyl radical, R 3 is a hydrogen atom or an alkyl, hydroxyalkyl radical, alkoxyalkyl, alkenyl or cycloalkyl, each with up to 6 carbon atoms, R4 is a hydrogen atom, a hydroxyl group, or an alkyl radical of up to 6 carbon atoms, and acid addition salts of these compounds, are reacted with a reactive derivative of the general formula 12, wherein R1 and R4 have the meanings given above, with the amine of the general formula R3NH2 in which R3 is as defined above. 4. The method according to p. A reactive derivative of the acid of the general formula 10 and the amine of the general formula R2 R3NH are used as the starting compounds, in which the formulas R1 is a III-butyl radical, R3 is a methyl radical, R4, Rs, R7 and R8 are hydrogen and R2 is as defined in claim 1. 1.91 770 Table I Compound of general formula 3 R1 isopropyl M1-prebutyl isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl Ml-pre-butyl isopropyl isopropyl-n-butyl H-butyl isopropyl isopropyl-butyl H-1 primary butyl n-hexyl isohexyl n-heptyl allyl allyl cyclopentyl cyclohexyl benzyl R4 HH methyl n-propyl allyl Br methoxy HHHHHHHHHHHH Melting point ° C 123-125 88- 90 146-148 141-143 121-123 159-161 125-128 108-109 75- 78 98-100 90- 92 92- 94 * 80- 83 90- 92 112-114 78- 80 101-103 111-114 102-104 Table II Compound of general formula 7 Melting point ° c isopropyl H 107-110 Table III Compound of general formula 8 isopropyl M1-tert.butyl H methyl n-propyl isobutyl 11-tier butyl I M1-tert.butyl n-hexyl R1 isopropyl isopropyl R1 methyl R3 isopropyl Ta Compound o HH methyl methyl methyl methyl methyl methyl methyl R3 Melting point b 1 and ca 1 ° C 62-66 97-100 IV with general formula 4H HHHHHHHH R4 enia / Melting point ° C 108-109 (oil) 88-90 97-100 114-115 117 98-100 96-97 8791770 1 allyl 2-hydroxy-11, dimethylethyl 2- (3,4-dimethoxyphenoxy-ethyl isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl III-tbutyl isopropyl III-tbutyl isopropyl isopropyl isopropyl III-tbutyl 2-hydroxy-1,1-dimethylethyl I-isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl isopropyl methyl methyl methyl methyl methyl methyl methyl ethyl ethyl n-propyl n-propyl isopropyl n-butyl allyl allyl allyl benzyl cyclopentyl cyclohexyl | 3-hydroxyethyl | 3-methoxyethyl 7-hydroxypropyl 7-hydroxypropyl Table V 3 HHH methyl methoxyHHHHHHHiazHHHHHHHHHHiazekHHH of general formula 9 R3 R5 A 4 92-93 98-101 (oil) 101-103 80 ^ 82 130-132 104-106 111-115 97-98 hydrochloride 152 89-90 (oil) 89-94 83-84 86 (oil) (oil) 84-86 72-74 92-94 79-81 78 ^ 80 52-54 64 Melting point ° C isopropyl isopropyl isopropyl isopropyl III-order .butyl ethyl pentamethyl HHH ethyl methyl methyl methyl HHH methyl methyl CH2- -CH2- -CH (CH3) - CH2- -CH2- 55-58 hydrogen oxalate 98-100 102-105 hydrochloride 184-186 hydrochloride 177-17991770 H02-CA- 0 ORT ^ ^ yOCHgCHOHCHR ^ NHR '\ zfc / R4 Formula 3 H02C-A-OCH 2.CHOH.CH2NHR' \=t/ R4 Wzór 6 Wzór 2 /-^ . P3NHCO(cH2)xO-f NVoCH2CHOHC^-l,NHR, R3NHCOCH20-P ^-OCH2CHOHCH2NHR1 v ^ \=/ L R4 Wzór 7 Wzór 3 r' V0CH2CH0HCH2NHRI R4-^ 7-OCH0CHOHCH0NHR1 . / \—/ ' R3NHCOCH20 ^OCH2CONHR3 Wzór 8 Wzór 4 " ^OCH2CHOHCHR5NHRl '0-A-CONR2R3 Wzór 9 OR7 R \ 7-°CH2CHCHR5NRlR8 ^O-A-COOH WzOr lO H02C-A-Ov N^OCH2.CHOH.CH2NHR4 R* Wzór l'l R4 \ /~OC|-|2CHOHCH2NHR< ^OCH2-C02H Wzór 12 PL PL PL PL2.CHOH.CH2NHR '\ = t / R4 Formula 6 Formula 2 / - ^. P3NHCO (cH2) xO-f NVoCH2CHOHC ^ -1, NHR, R3NHCOCH20-P ^ -OCH2CHOHCH2NHR1 v ^ \ = / L R4 Formula 7 Formula 3 r 'V0CH2CH0HCH2NHRI R4- ^ 7-OCH0CHOHCH0NHR1. / \ - / 'R3NHCOCH20 ^ OCH2CONHR3 Formula 8 Formula 4 "^ OCH2CHOHCHR5NHRl' 0-A-CONR2R3 Formula 9 OR7 R \ 7- ° CH2CHCHR5NRlR8 ^ OA-COOH Formula 10 H02C-A-Ov N ^ OCH2.HR4 RCH2NHR4OH.CH2NHR4 Formula l'l R4 \ / ~ OC | - | 2CHOHCH2NHR <^ OCH2-C02H Formula 12 PL PL PL PL
PL1971174904A 1970-05-27 1971-05-24 Method of producing alkanolamine derivatives[cs181211b2] PL91770B1 (en)

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US4059622A (en) * 1970-05-27 1977-11-22 Imperial Chemical Industries Limited Alkanolamine derivatives
GB8714901D0 (en) * 1986-07-23 1987-07-29 Ici Plc Amide derivatives

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DK132551C (en) 1976-05-31
FR2100689A1 (en) 1972-03-24
CS181211B2 (en) 1978-03-31
IE35386B1 (en) 1976-02-04
HU162987B (en) 1973-05-28
NL7107229A (en) 1971-11-30
AR202882A1 (en) 1975-07-31
MY7700173A (en) 1977-12-31
CH563962A5 (en) 1975-07-15
CH576424A5 (en) 1976-06-15
BE767781A (en) 1971-11-29
DE2126169C3 (en) 1981-03-19
NO130231B (en) 1974-07-29
DE2126169B2 (en) 1980-07-24
AT317870B (en) 1974-09-25
FR2100689B1 (en) 1974-09-27
DK132551B (en) 1975-12-29
ES391627A1 (en) 1974-05-01
FI54599B (en) 1978-09-29
CS181249B2 (en) 1978-03-31
AT323130B (en) 1975-06-25
CH575911A5 (en) 1976-05-31
IL36933A (en) 1974-01-14
IE35386L (en) 1971-11-27
AT323720B (en) 1975-07-25
AR209572A1 (en) 1977-05-13
KE2686A (en) 1977-06-24
IL36933A0 (en) 1971-08-25
JPS5644062B1 (en) 1981-10-16
FI54599C (en) 1979-01-10
AR209056A1 (en) 1977-03-31
HK11377A (en) 1977-03-11
DE2126169A1 (en) 1971-12-09
PL91769B1 (en) 1977-03-31
SU514565A3 (en) 1976-05-15
NL171576C (en) 1983-04-18
SE399066B (en) 1978-01-30

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