PL93792B1 - Derivatives of 1-phenoxy-3-amino-propan-2-ol and process for their producrion[gb1362168a] - Google Patents

Derivatives of 1-phenoxy-3-amino-propan-2-ol and process for their producrion[gb1362168a] Download PDF

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PL93792B1
PL93792B1 PL1972157055A PL15705572A PL93792B1 PL 93792 B1 PL93792 B1 PL 93792B1 PL 1972157055 A PL1972157055 A PL 1972157055A PL 15705572 A PL15705572 A PL 15705572A PL 93792 B1 PL93792 B1 PL 93792B1
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substituted
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PL1972157055A
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Cassella Farbwerke Mainkur Ag
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Priority claimed from CH1141571A external-priority patent/CH578532A5/xx
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Publication of PL93792B1 publication Critical patent/PL93792B1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1362168 Derivatives of 1-phenoxy-3-aminopropan-2-ol CASSELLAFARBWERKEMAINKUR AG 25 July 1972 [3 Aug 1971 29 Feb 1972] 34763/72 Heading C2C [Also in Division A5] Novel, therapeutic compounds (I) (including optical isomers, aldehyde condensation products and acid addition salts thereof) where X is the group (II) or (III) and the phenyl ring I may have up to three similar or different substituents selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkoxy, alkenyloxy, alkynyloxy, phenyl, halogen and the radical -NR 1 R 2 , R 1 standing for alkyl or acyl and R 2 standing for hydrogen or alkyl, are made by standard methods. The following compounds are also prepared: 1-amino-3-(o-allyloxyphenoxy)-propan-2-ol and its hydrochloride, the sodium salt of nicotinoyl vinyl alcohol, 1-(2<SP>1</SP>-methoxy-4<SP>1</SP>-allylphenoxy)-2,3- epoxypropane, 1-(#-pyridyl)-3-amino-propan-1-ol N-(nicotinoylvinyl)-benzylamine and 1-(#-pyridyl)-3-benzylamino-propan-1-ol. [GB1362168A]

Claims (1)

Zastrzezenia patentowe 1. Sposób wytwarzania nowych pochodnych 1- -fenoksy-3-amino-propanolu-2 o wzorze ogólnym 1, w którym X oznacza reszte o wzorze 4 lub o wzorze 5, przy czym reszta pirydynowa jest pod¬ stawiona w polozeniu 2 lub 4, a pierscien feny Io¬ wy I moze byc podstawiony jedno-, dwu- lub trzykrotnie przez alkil, zwlaszcza o 1—4 atomach wegla, alkeny 1, zwlaszcza do 6 atomów wegla, al-* kinyl, zwlaszcza do 6 atomów wegla, cykloalkil, zwlaszcza zawierajacy 5—8 atomów wegla w piers¬ cieniu ,cykloalkenyl, zwlaszcza zawierajacy 5—8 atomów wegla w pierscieniu lub przez grupe al- koksy, alkenyloksy lub alkinyloksy, zwlaszcza za¬ wierajace do 5 atomów wegla kazda, lub przez fenyl, chlorowiec, zwlaszcza chlor lub brom, lub przez reszte —NI^R* przy czym w reszcie tej R4 oznacza alkil, zwlaszcza o 1—4 atomów wegla lub acyl, zwlaszcza do 11 atomów wegla, a R2 oznacza wodór lub alkil, zwlaszcza do 4 atomów wegla, lub ich soli addycyjnych z kwasami, znamienny- tym, ze zwiazek o wzorze ogólnym 2 poddaje sie reakcji ze zwiazkiem o wzorze 3, w którym X ma wyzej podane znaczenie, a Y oznacza chlorowiec i jezeli X oznacza reszty o wzorze 4, to Y oznacza takze —OH, —OK, lub —ONa, w obojetnym orga¬ nicznym rozpuszczalniku lub dyspergatorze, w tem¬ peraturze miedzy 0°C a temperatura wrzenia roz¬ puszczalnika, korzystnie w temperaturze 15—35°C 40 45 55 $5 i otrzymane zwiazki o wzorze 1 ewentualnie prze¬ prowadza sie za pomoca kwasu w sole addycyjne. 2. Sposób wedlug zastrz. 1, znamienny tym, ze zwiazek o wzorze 2, w którym pierscien fenylowy I podstawiony jest przez winyl, allil, metallil lub krotyl, poddaje sie reakcji ze zwiazkiem o wzo¬ rze 3, w którym symbole X i Y maja znaczenie podane w zastrz. 1. 3. Sposób wedlug zastrz. 1, znamienny tym, ze zwiazek o wzorze 2, w którym pierscien fenylowy I podstawiony jest przez cyklopentenyl, poddaje sie reakcji ze zwiazkiem o wzorze 3, w którym symbole X i Y maja znaczenie podane w zastrz. 1. 4. Sposób wedlug zastrz. 1, znamienny tym, ze zwiazek o wzorze 2, w którym pierscien fenylo¬ wy I podstawiony jest przez cyklopentyl lub cy- kloheksyl, poddaje sie reakcji ze zwiazkiem o wzo¬ rze 3, w którym symbole X i Y maja znaczenie podane w zastrz. 1. 5. Sposób wedlug zastrz. 1, znamienny tym, ze zwiazek o wzorze 2, w którym pierscien fenylowy I podstawiony jest przez grupe metoksy, etoksy, propoksy, butoksy, alliloksy, metalliloksy, lub pro- pargiloksy, poddaje sie reakcji ze zwiazkiem o wzorze 3, w którym symbole X i Y maja znacze¬ nie podane w zastrz. 1. 6. Sposób wedlug zastrz. 1, znamienny tym, ze zwiazek o wzorze 2, w którym pierscien fenylowy I podstawiony jest przez reszte —NRiR2, w której Rj oznacza metyl, etyl, acetyl, benzoil, a R2 —93 792 13 wodór, metyl lub etyl, poddaje sie reakcji ze zwiazkiem o wzorze 3, w którym symbole X i Y maja znaczenie podane w zastrz. 1. 7. Sposób wytwarzania nowych pochodnych 1- -fenoksy-3-amino-propanolu-2 o wzorze ogólnym 1, w którym X oznacza reszte o wzorze 4 lub o wzo¬ rze 5, przy czym reszta pirydynowa jest podsta¬ wiona w pozycji 3, a pierscien fenyIowy I moze byc podstawiony jedno-, dwu- lub trzykrotnie przez alkil, zwlaszcza o 1—4 atomach wegla, alkenyl, zwlaszcza do 6 atomów wegla, alkinyl, zwlaszcza do 6 atomów wegla, cykloalkil, zwlaszcza zawiera¬ jacy 5—8 atomów wegla w pierscieniu lub przez grupe alkoksy, alkenyloksy, alkinyloksy, zwlaszcza zawierajace do 5 atomów wegla kazda, lub przez fenyl, chlorowiec, zwlaszcza chlor lub brom, lub przez reszte —NRjRg, przy czym w reszcie tej Rt oznacza alkil, zwlaszcza o 1—4 atomach wegla lub acyl, zwlaszcza do 11 atomów wegla, a R2 oznacza wodór lub alkil, zwlaszcza do 4 atomów wegla, lub ich soli addycyjnych z kwasami, znamienny tym, ze zwiazek o wzorze ogólnym 2 poddaje sie reakcji ze zwiazkiem o wzorze 3, w którym X ma wyzej podane znaczenie, przy czym reszta pirydynowa jest podstawiona w pozycji 3, a Y oznacza chlorowiec i jezeli X oznacza reszte o wzorze 4 to Y oznacza takze OH, OK lub ONa, w obojetnym organicz¬ nym rozpuszczalniku lub dyspergatorze, w tempe¬ raturze miedzy 0°C, a temperatura wrzenia roz¬ puszczalnika, korzystnie w temperaturze 15—35°C i otrzymane zwiazki o wzorze 1 ewentualnie prze¬ prowadza sie za pomoca kwasu w sole addycyjne. 8. Sposób wedlug zastrz. 7, znamienny tym, ze zwiazki o wzorze 2, w którym pierscien fenylowy I podstawiony jest przez winyl, allil, metallil lub krotyl, poddaje sie reakcji ze zwiazkiem o wzprze 3, w którym symbole X i Y maja znaczenie po¬ dane w zastrz. 1. 9. Sposób wedlug zastrz. 7, znamienny tym, ze zwiazek o wzorze 2, w którym pierscien fenylowy I podstawiony jest przez cyklopentyl lub cyklohek- 14 10 15 20 25 30 35 40 syl, poddaje ,sie ^reakcji ze zwiazkiem o wzorze 3, w którym symbole Xi Y maja znaczenie poflane w zastrz. 1. 10. Sposób wedlug zastrz. 7, znamienny tym, ze zwiazek o wzorze 2, w którym pierscien fenylowy I podstawiony jest przez grupe metoksy, etoksy, propoksy, butoksy, alliloksy, metalliloksy, propar- giloksy, poddaje sie reakcji ze zwiazkiem o wzo¬ rze 3, w którym symbole X i Y maja znaczenie podane w zastrz. 1. 11. Sposób wedlug zastrz. 7, znamienny tym, ze zwiazek o wzorze 2, w którym pierscien fenylowy I podstawiony jest przez grupe -^NR^, przy czym w grupie tej Ri oznacza metyl, etyl, acetyl, benzoil, a R2 oznacza wodór, metyl lub etyl, podda¬ jac sie reakcji ze zwiazkiem o wzorze 3, w którym symbole Xi Y maja znaczenie podane w zastrz. 1. 12. Sposób wytwarzania nowych pochodnych 1- -fenoksy-3-amino-propanolu-2 o wzorze ogólnym 1, w którym X oznacza reszte o wzorze 4 lub o wzo¬ rze 5, przy czym reszta pirydynowa jest podsta¬ wiona w pozycji 3, a pierscien fenylowy I jest podstawiony przez cykloalkenyl, zawierajacy 5—8 atomów wegla w pierscieniu, lub ich soli addycyj¬ nych, znamienny tym, ze zwiazek o wzorze ogól¬ nym 2, poddaje sie reakcji ze zwiazkiem o wzorze 3, w którym X ma wyzej podane znaczenie, przy czym reszta pirydynowa jest podstawiona w po¬ zycji 3, a Y oznacza chlorowiec i jezeli X ozna¬ cza reszte o wzorze 4, to Y oznacza takze —OH, —OK lub —ONa, w obojetnym organicznym roz¬ puszczalniku lub dyspergatorze, w temperaturze miedzy 0°C a temperatura wrzenia rozpuszczalnika, korzystnie w temperaturze 15—35°C i otrzymane zwiazki o wzorze 1 ewentualnie przeprowadza sie za pomoca kwasu w sole addycyjne. 13. Sposób wedlug zastrz. 12, znamienny tym, ze zwiazek o wzorze 2, w którym pierscien fenylowy I podstawiony jest przez cyklopentenyl, poddaje sie reakcji ze zwiazkiem o wzorze 3, w którym symbole Xi Y maja znaczenie podane w zastrz.Claims 1. A method for the preparation of the new 1-phenoxy-3-amino-propanol-2 derivatives of the general formula I, in which X represents the residue of the formula IV or formula 5, the pyridine residue being substituted in the position 2 or 4, and the ring of Io's phene I can be substituted one, two or three times with alkyl, especially with 1 to 4 carbon atoms, alkenes 1, especially up to 6 carbon atoms, alkynyl, especially up to 6 carbon atoms, cycloalkyl, especially with 5 to 8 ring carbon atoms, cycloalkenyl, especially with 5 to 8 ring carbon atoms, or through an alkoxy, alkenyloxy or alkynyloxy group, especially with up to 5 carbon atoms each, or through phenyl, halogen, in particular chlorine or bromine, or by the residue -N1- R * where R4 in the residue is alkyl, especially 1 to 4 carbon atoms, or acyl, especially up to 11 carbon atoms, and R2 is hydrogen or alkyl, especially up to 4 carbon atoms, or acid addition salts thereof, characterized in that the compound of the formula Subsequent 2 is reacted with a compound of formula III, in which X is as defined above and Y is halogen, and if X is a residue of formula 4, Y also represents —OH, —OK, or —ONa, in an inert organism can be used as a solvent or dispersant, at a temperature between 0 ° C. and the boiling point of the solvent, preferably at a temperature of 15 ° -35 ° C. 40 45 55%, and the compounds of formula I obtained are optionally converted into addition salts with an acid. 2. The method according to claim A compound of formula 1, wherein the phenyl ring I is substituted with vinyl, allyl, methallyl or crotyl is reacted with a compound of formula 3, wherein the symbols X and Y have the meaning given in claim 1. 1. 3. The method according to claim 1 A compound according to claim 1, characterized in that the compound of formula 2, in which phenyl ring I is substituted with cyclopentenyl, is reacted with a compound of formula 3, wherein the symbols X and Y have the meaning given in claim 1. 1. 4. The method according to claim 1 The compound of formula 1 in which the phenyl ring I is substituted with cyclopentyl or cyclohexyl is reacted with a compound of formula 3 in which the symbols X and Y have the meaning given in claim 1. 1. 5. The method according to claim 1 A compound according to claim 1, characterized in that the compound of formula II, in which the phenyl ring I is substituted with a methoxy, ethoxy, propoxy, butoxy, allyloxy, methallyloxy, or propargyloxy group, is reacted with a compound of formula III in which the symbols X and Y have the meanings given in claims 1. 6. The method according to claim 1 A compound according to claim 1, characterized in that the compound of formula II, in which the phenyl ring I is substituted with the residue —NRiR2, in which Rj is methyl, ethyl, acetyl, benzoyl, and R2 -93,792 13 hydrogen, methyl or ethyl, is reacted with a compound of formula 3, wherein the symbols X and Y have the meaning given in claim 1. 7. Process for the preparation of the new 1-phenoxy-3-amino-propanol-2 derivatives of the general formula I, in which X represents the residue of the formula IV or the formula 5, the pyridine residue being substituted at the 3, and the phenylic ring I may be substituted one, two or three times with alkyl, especially with 1 to 4 carbon atoms, alkenyl, especially up to 6 carbon atoms, alkynyl, especially up to 6 carbon atoms, cycloalkyl, especially 5 -8 carbon atoms in the ring or through an alkoxy, alkenyloxy, alkynyloxy group, in particular with up to 5 carbon atoms each, or through a phenyl, a halogen, especially chlorine or bromine, or through a residue -NRjRg, where Rt in the remainder is alkyl, especially of 1-4 carbon atoms or acyl, especially up to 11 carbon atoms, and R2 is hydrogen or alkyl, especially up to 4 carbon atoms, or acid addition salts thereof, characterized in that a compound of general formula II is reacted with a compound of Formula 3, wherein X is as defined above, the remainder pyridine is substituted at the 3-position and Y is halogen, and if X is an residue of formula IV, Y is also OH, OK, or ONa, in an inert organic solvent or dispersant, at a temperature between 0 ° C and the boiling point. in a solvent, preferably at a temperature of 15 ° -35 ° C., and the compounds of formula I obtained are optionally converted into addition salts with an acid. 8. The method according to p. A compound according to claim 7, characterized in that the compounds of formula II, in which the phenyl ring I is substituted with vinyl, allyl, metallyl or crotyl, are reacted with a compound of formula 3, wherein the symbols X and Y have the meaning given in claim 1. 1. 9. The method according to claim 1 7. The process according to claim 7, characterized in that the compound of formula 2, in which the phenyl ring I is substituted with cyclopentyl or cyclohexyl, is reacted with a compound of formula 3, wherein the symbols X and Y are floated meaning in claim The method according to claim 1. 7. The method according to claim 7, characterized in that the compound of formula II, in which the phenyl ring I is substituted with a methoxy, ethoxy, propoxy, butoxy, allyloxy, methallyloxy, propargyloxy group, is reacted with a compound of formula 3, wherein the symbols X and Y are as defined in claim 1. A method according to claim 1. The process according to claim 7, characterized in that the compound of formula II, in which the phenyl ring I is substituted with the group -3NR4, in which R1 is methyl, ethyl, acetyl, benzoyl and R2 is hydrogen, methyl or ethyl, A reaction with a compound of formula III, wherein the symbols X and Y have the meaning given in claim 1. 12. Process for the preparation of the new 1-phenoxy-3-amino-propanol-2 derivatives of the general formula I, in which X represents the residue of the formula IV or the formula 5, the pyridine residue being substituted in the 3, and the phenyl ring I is substituted with a cycloalkenyl having 5-8 ring carbon atoms, or their addition salts, characterized in that a compound of general formula II is reacted with a compound of formula III in which X is as defined above, wherein the pyridine residue is substituted at the 3-position and Y is halogen, and if X is a residue of formula IV, Y also represents —OH, —OK, or —ONa in an inert organic solution. In the solvent or dispersant, at a temperature between 0 ° C and the boiling point of the solvent, preferably at 15 ° -35 ° C, and the compounds of the formula I obtained are optionally converted into addition salts with an acid. 13. The method according to p. A compound according to claim 12, characterized in that the compound of formula II, in which phenyl ring I is substituted with cyclopentenyl, is reacted with a compound of formula III, wherein the symbols X and Y have the meaning given in claim 1. 1. //i\ 0-CH2 -CH -CH2-HH ~ X OH WZÓR i f*\-0-CH2-CH-Ofe-Afffc + Y-X^(Jjr0-CH2-pH-0H2-NH-X OH WZÓR 2 -HY WZÓR 3 WZÓR 1 SCHEMAT93 792 Y—CH=^CH~C 11 ^A7- o « WZÓR 3a Hal - CH? -CH2 -CH —-|- OH WZÓR 3c *W Hat-CH=CH- C li O WZÓR 30 Ar -CH=CH-C- O N WÓR 4 (iy 0~CH2-CH-CH2 WZÓR Aa 0-CH2 -CH -CH2~HaL I OH WZÓR 4693 792 CH2-~CH2-CH- I ^w OH N WZÓR 5 OH WZÓR 6 f\ \ -O —CH2-CH- CH2~ NH2 • HCl OH 0-QH2~CH=CHz WZÓR 7 ^ AT -C-CH=CH-ONa I! o WZÓR 8 O-CWo- CH-CH--NH- CH=CH-C- * I * II OH O 0-CH2-C//=CH2 -/r WZÓR 9 0-CH9-CH —CHP V 0-CH2-CH=CH2 WZÓR 10 -O- CH-CH- -CH2-NH2 OH 0-CH2-CH=CH2 WZÓR 1193 792 (CH$yC-/ V-O- CH2-CH-CH2-NH2 OH WZÓR 12 yCO-CH=CH-CL W HCL WZÓR 13 (0H5)5-C^ y-0-CH2-CH-CH2-NH-CH^CH-C WZÓR 14 Al' (CH3)5-C-ft \-0-CH2-CH-CH2-NH-CH2-CHzCH- ^^ OH OH OH WZÓR 15 V CO-CH=CH-ONa ^ WZÓR 1693 792 O- CH2- CH- CH2- NH2 • HCL OH 0-C2H5 WZÓR 17 O- CH0-CH-CH0-NH-CH=CH-C —5- 2 i 2 ! c^\ O-CM 2n5 OH WZÓR 18 WZÓR 19 WZÓR 2093 792 ,CH* 4 — N's 'CO -o WZÓR. 21 WZÓR 22 Bltk 1886/77 r. 110 egz. A4 Cena 10 zl PL PL1. // i \ O-CH2 -CH -CH2-HH ~ X OH FORMULA if * \ - O-CH2-CH-Ofe-Afffc + YX ^ (Jjr0-CH2-pH-OH2-NH-X OH FORMULA 2 -HY FORMULA 3 FORMULA 1 SCHEME 93 792 Y — CH = ^ CH ~ C 11 ^ A7- o «FORMULA 3a Hal - CH? -CH2 -CH —- | - OH FORMULA 3c * W Hat-CH = CH- C li O FORMULA 30 Ar -CH = CH-C- ON FORMULA 4 (iy 0 ~ CH2-CH-CH2 FORMULA Aa 0-CH2 -CH -CH2 ~ HaL AND OH FORMULA 4693 792 CH2- ~ CH2-CH- I ^ in OH N FORMULA 5 OH FORMULA 6 f \ -O —CH2-CH- CH2 ~ NH2 • HCl OH 0-QH2 ~ CH = CHz FORMULA 7 ^ AT -C-CH = CH-ONa I! O FORMULA 8 O-CWoCH -CH - NH- CH = CH-C- * I * II OH O 0-CH2-C // = CH2 - / r FORMULA 9 0-CH9-CH —CHP V 0-CH2-CH = CH2 FORMULA 10 - O- CH-CH- -CH2-NH2 OH 0-CH2-CH = CH2 FORMULA 1193 792 (CH $ yC- / VO- CH2-CH-CH2-NH2 OH FORMULA 12 yCO-CH = CH-CL IN HCL FORMULA 13 (OH5) 5-C ^ y-O-CH2-CH-CH2-NH-CH ^ CH-C FORMULA 14 Al '(CH3) 5-C-ft \ -O-CH2-CH-CH2-NH-CH2- CHzCH- ^^ OH OH OH MODEL 15 V CO-CH = CH-ONa ^ MODEL 1693 792 O- CH2- CH- CH2- NH2 • HCL OH 0-C2H5 FORMULA 17 O- CH0-CH-CH0-NH-CH = CH-C —5- 2 and 2! C ^ \ O-CM 2n5 OH MODEL 18 MODEL 19 MODEL 2093 792, CH * 4 - N's' CO -o MODEL 21 MODEL 22 Bltk 1886/77 110 copies A4 Price 10 zl PL PL
PL1972157055A 1971-08-03 1972-08-01 Derivatives of 1-phenoxy-3-amino-propan-2-ol and process for their producrion[gb1362168a] PL93792B1 (en)

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CH1141571A CH578532A5 (en) 1971-08-03 1971-08-03
DE2209467A DE2209467A1 (en) 1971-08-03 1972-02-29 DERIVATIVES OF 1-PHENOXY-3-AMINO-PROPAN2-OL AND PROCESS FOR THEIR PRODUCTION

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PL1972181323A PL94243B1 (en) 1971-08-03 1972-08-01 Derivatives of 1-phenoxy-3-amino-propan-2-ol and process for their producrion[gb1362168a]
PL1972157055A PL93792B1 (en) 1971-08-03 1972-08-01 Derivatives of 1-phenoxy-3-amino-propan-2-ol and process for their producrion[gb1362168a]

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AT (3) AT323174B (en)
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CA (1) CA984839A (en)
DD (1) DD98673A5 (en)
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AR209577A1 (en) 1977-05-13
DD98673A5 (en) 1973-07-05
ES405484A1 (en) 1976-04-16
BE787057A (en) 1973-02-01
SE398642B (en) 1978-01-09
SU487484A3 (en) 1975-10-05
ES407062A1 (en) 1976-02-01
RO64866A (en) 1979-02-15
AR209578A1 (en) 1977-05-13
SU481150A3 (en) 1975-08-15
PL94243B1 (en) 1977-07-30
FR2150720A1 (en) 1973-04-13
AT323174B (en) 1975-06-25
HU165016B (en) 1974-06-28
CA984839A (en) 1976-03-02
AT323167B (en) 1975-06-25
AR203000A1 (en) 1975-08-08
AT323176B (en) 1975-06-25
IE36595B1 (en) 1976-12-08
RO62788A (en) 1977-12-15
FR2150720B1 (en) 1975-08-08
AR207847A1 (en) 1976-11-08
PL94261B1 (en) 1977-07-30
RO64865A (en) 1979-02-15
SU457211A3 (en) 1975-01-15
IL39992A0 (en) 1972-09-28
RO64864A (en) 1979-01-15
IE36595L (en) 1973-02-03
IL39992A (en) 1975-03-13
ES407061A1 (en) 1976-02-01
NL7210194A (en) 1973-02-06
GB1362168A (en) 1974-07-30

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