PL84268B1 - - Google Patents
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- PL84268B1 PL84268B1 PL1971174913A PL17491371A PL84268B1 PL 84268 B1 PL84268 B1 PL 84268B1 PL 1971174913 A PL1971174913 A PL 1971174913A PL 17491371 A PL17491371 A PL 17491371A PL 84268 B1 PL84268 B1 PL 84268B1
- Authority
- PL
- Poland
- Prior art keywords
- group
- hydroxy
- hydrogen
- phenyl
- lower alkyl
- Prior art date
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical class CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 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 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
- -1 hydroxyl phenyl group Chemical group 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- LUSZGTFNYDARNI-UHFFFAOYSA-N Sesamol Chemical compound OC1=CC=C2OCOC2=C1 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CELVZQVZKDEMBP-UHFFFAOYSA-N 3-amino-3-methyl-1-phenylbutan-1-ol Chemical compound CC(C)(N)CC(O)C1=CC=CC=C1 CELVZQVZKDEMBP-UHFFFAOYSA-N 0.000 description 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- WQPPYOAGCWAZEI-UHFFFAOYSA-N ethylazanium;benzoate Chemical compound CC[NH3+].[O-]C(=O)C1=CC=CC=C1 WQPPYOAGCWAZEI-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/008—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy comprising drug dissolved or suspended in liquid propellant for inhalation via a pressurized metered dose inhaler [MDI]
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/56—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups
- C07C215/58—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
- C07C215/62—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain the chain having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/48—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/64—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms
- C07C217/66—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain
- C07C217/72—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
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- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Emergency Medicine (AREA)
- Otolaryngology (AREA)
- Pulmonology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarzania nowych l-hydroksyfenylo-l-hydroksy-2- (3-airylo-3- -hydroksypropylo)-aminoetanów w postaci racematu ewentualnie diastereomerycznych enancjomerów, czystyich, optycanie czynnych izomerów oraz ich 5 soli addycyjnych z kfwa Nowym zwiazkom odpowiada wzór ogólny 1, w którym Rt oznacza wodór lub nizsza grupe alkilowa lub alkoksylowa, R2 oznacza wodór, grupe metylowa hub etylowa, R8 oznacza wodór lmb giru/pe metylowa, i0 R4 oznacza wodór lub nizsza grupe alkilowa, R5 oznacza wodór lub grupe hydroksylowa i A oznacza ewentualnie podstawiona chlorowcem, nizsza grupe alkilowa, nizsza grupe alkoksylowa i/lub hydroksy¬ lowa grupe fenylowa lub skondensowana grupe dwu- 15 cykliczna, w której nie zwiazany bezposrednio z lan¬ cuchem alifatycznym pierscien jest izocykliczny lub heterocykliczny, nasycony lub aromatyczny, przy czym do grup dwucyklicznych tego rodzaju zaliczaja sie, np. grupa naftylowa, 3,4-metylenodwuoksyfeny- 20 Iowa i benzodioksanylowa.Wedlug wynalazku nowe zwiazki wytwarza sie przez redukcje zwiazku o wzorze ogólnym 2, w któ¬ rym wszystkie symbole maja wyzej podane znacze¬ nie. Reakcje prowadzi sie przez katalityczne uwodór- 25 nienie w obecnosci niklu, platyny lub palladu, jako katalizatora lub przez redukcje kompleksowymi wo¬ dorkami, w szczególnosci borowodorkiem sodowym.Otrzymany produkt ewentualnie rozdziela sie na op¬ tycznie czynne postacie lub ewentualnie w diastereo- 30 2 meryczne enancjomery i/lub przeprowadza sie w sole addycyjne z kwasami. Produkty wyjsciowe wytwa¬ rza sie znanymi do wytwarzania takich zwiazków metodami.Zwiazki, otrzymywane sposobem wedlug wynalaz¬ ku, wykazuja wlasciwosci terapeutyczne. Stanowia one substancje czynna leków stosowanych w cho¬ robach serca i krazeniowych. Srodki te stosuje sie w postaci znanych preparatów galenowych, zawie¬ rajacych znane srodki pomocnicze i nosniki, np. w postaci tabletek, drazetek, kapsulek, aerozoli, kropli i roztworów injekcyjnych. Pojedyncza dawka wy¬ nosi okolo 0,1—20 mg. Nastepujace pmzyiklaidy wyja¬ sniaja blizej wynalazek, nie ograniczajac jego zakre¬ su. Wydajnosc kazdorazowo podana jest w % wydaj¬ nosci teoretycznej.Przyklad I. Erytro-*l-(4-hydroksyfenylo)-l-hy- droksy-2-metylo-2-[(3-fenylo-3-hydroksy)-propylo]- -aminoetan. 4,79 g 4-benzyloksy-a-N-benzylo-N-(3- -fenylo-3-hydroksy)-propyloamino-propiofenonu uwodarnia sie w 100 ml metanolu, w obecnosci ni¬ klu Raney'a jako katalizatora, w normalnych wa¬ runkach do erytro-l-(4-hydroksyfenylo)-l-hydroksy- -2-metylo-2-[(3-fenylo-3-hydroksy)-propylo] -amino- etanu, o temperaturze topnienia 186°C (z izopropano- lu).Przyklad II. l-(3,5-dwuhydroksyfenylo)-l-hy- droksy-2- [(3-fenylo-3-hydroksy-l,l-dwumetylo)-pro¬ pylo]-amiinoetan. Przez reakcje 3,5^wiufbenzytloksy- -w-bromocefofenonu z (3-fenylo-3-hydroksy-l,l-dwu-84 268 3 4 metylo)-propyloamina otrzymuje sie z 7(1% wydajno¬ scia chlorowodorek (3,5-dwubenzyloksy)-co-N-(3-fe- nylo-3-hydroksy-1,1- dwumetylo)-propyloainino-ace- tofenomi (temperatura topnienia 120°C). Aminoketon piizepiio/waidzia sie w zasade i w meltamodu uwoldorniia wobec ixikl,u. Raney'a do l-(3,5-dwuhydroksyfenylo)- -l-hydroksy-2-[(3-fenylio-3-hydroksy-l,l-dwumety- lo)-propylo]-aminoetanu. Po dodaniu kwasu benzo¬ esowego wyodrebnia sie z acetonitrylu diastereome- ryczny benzoesan, o temperaturze topnienia 19,9°C i 142°C (wodzian).Przyklad III. l-(4-hydroksyfe:nylo)-l-Gydro- ksy-2-[(3-fenylo^3-hydroksy)-propylo] -aminoetan. 23,3 g (0,05 mola) 4-benzyloksy-a-N-benzylo-N-(3-fe- nylo-3-hydroksy) -propyloamino-aoetofenonu zadaje sie w mieszaninie 125 ml metanolu i wody 10 ml 17,6% roztworem eterowym kwasu solnego i uwo¬ dornia w temperaturze 60°C i 5 atn, w obecnosci pal¬ ladu na weglu jako katalizatora, az do pobrania 0,1 mola wodoru. Utworzony chlorowodorek 4-hydro- ksyfenylo-co-N- (3-fenylo-3-hydroksy)-propyloamino- -aoetofenonu (temperatura topnienia: 188°C, z wo¬ dy) uwodornia sie w obecnosci platyny jako. katali¬ zatora do 1-(4-hydroksyfenylo)-1-hydroksy-2-[(3-fe- nylo-3-hydroksy)-propylo]-aminoetanu. Rozdzielenie na diastereomery zachodzi przez zasajde. Diastereo- meryczne zwiazki topnieja w temperaturze 112 wzglednie 158°C.Odpowiednio do podanych przykladów otrzymuje sie nastepujace zwiazki: siarczan l-(4-hydroksysenylo)-l-hydroksy-2-[(3^£eny- lo-3-metoksy)-propylo]-aminoetanu, temperatura top¬ nienia: 205°C, benzoesan 1 - (3-hydroksyfenylo)-1-hydroksy-2- [(3-fe- nylo-3-hydroksy)-propylo] -aminoetanu, temperatura ^o^nienia: 128°C, chlorowodorek 1^ (4-hydroksyfenylo) -l-hydroksy-2- -[(3-fenylo-3-hydroksy-l,l-dwumetyloXpiropylo]-ami¬ noetanu, temperatura topnienia: 212°C, chlorowodorek treo-1-(4-hydroksyfenylo)-1-hydro- ksy-2-metylo^2- [(3-fenylo-3-hydroksy)-propylo]-ami¬ noetanu, temperatura topnienia: 160°C, X-(4-^diroksy-3-naetoksyfenylo)-l-hydroksy-2-[(3- -fenylo-3-hydroksy)-propylo]-aminoetan, postac X: zasada, temperatura topnienia: 162°C, siarczan: tem¬ peratura topnienia 163°C, postac Y:zasada, tempera¬ tura topmjienda 133°C, ohlorofwotioirek: temperatura topnienia 125°C. l-(3,5-d)wfunydiiiok&^^ E(3-fenylo- -3-hydroksy)-propylo] ^aminoetan, postac X: tempe- rajtura topnienia: 187°C, postac Y: ternperaituira top- nienlia: 102°C. benzoesan 1-(3,5-dwuhydroksyfenylo)-1 -hydroksy-2- -[(S-fenylcHS-hydroksy-ljl-dwumetylo^-propylo]- -aminoetanu, postac X: temperatura topnienia: 199°C, postac Y: temperatura topnienia: 142°C (wodzian), chlorowodorek l-(3,5-dwuhydroiks3rfenylo)-l-hodro- ksy-2- [(3-a-naftylo-3-hydroksy-1,1 -dwumetylo)-pro- pyilolHaimliinoetaniU', positac X: leniperaitura topnienia: 235°C, postac Y: temperatura topnienia: 149°C, benzoesan 1-(4-hydroksy-2-metylofenylo)-1-hydro- ksy-2- [i(3-o^me1y,Jjofenyao/-3-hydirioikBy)-propylo]- -aminoetanu, temperatura topnienia: 164°C, l-(4-hydroksy-2-metylofenylo)-l-hydroksy-2-[(3-p- -metoksyfenylo-3-hydroksy) -propylo]-amiinoetan, temperatura topnienia: 161°C, l-(4-hydroksy-2-metylofenylo)-l-hyiciroksy-2-[(3-p- -hydroksy-m-chloirofenylo-3-hydroksy)-propylo] - -aminoetan, postac X: temperatura topnienia: 161°C (chlorowodorek), postac Y: temperatura topnienia: 81CC (benzoesan), 1- (4-hydroksy-3-butoksyfenylo)-1-hydroksy-2-[3- -m,p-dwuetpksyfenyk-3-hydroksy) -propylo]-amino¬ etan^ zasiada: temperatura topnienia: 108°C, benzoesan: i^mperatura topnienia: 128°C, chlorowo¬ dorek: temperatura topnienia: 125°C, siarczan: tem¬ peratura topnienia: 172°C, benzoesan 1- (4-hydroksy-3-butoksyfenylo) -1-hydro- ksy-2-[(S-mjP-dwubutoksj^enylo-^-hydiioksy)-pro¬ pylo]-aminoetanu, temperatura topnienia: 101°C. PL PL PL PL PL PL
Claims (2)
1. Zastrzezenia patentowe i ; 1. Sposób wytWiarzania nowych 1-hydroksyfenylo- «1-hydroksy-2-(3-arylo-3-hydroksypropylo)-amino- etanów o wzorze ogólnym 1, w którym Rt oznacza wodór lub. nizsza grupe alkilowa lub alkoksylowa, R2 oznacza wodór, grupe metylowa lub etylowa, R3 oznacza wodór lub grupe metylowa, R4 oznacza wo¬ dór luJb nizsza grupe aiMlowa, R5 oznacza wodór lub grupe hydroksylowa i A oznacza grupe fenylowa ewentualnie podstawiona chlorowcem, nizsza grupa alkilowa, nizsza grupa alkoksylowa i/lub hydjroiksy- lowa albo skondensowana dwucykliczna grupe, w której pierscien nie zwiazany bezposrednio z ali¬ fatycznym lancuchem jest izocykliczny lub heterocy-. kliczny, nasycony lub aromatyczny, w postaci rape- maitu ewenrtoalnie diiasiter^eomer^cz^ eaancjiGime-, rów, czystych, optycznie czynnych izomerów, zna¬ mienny tym, ze zwiazek o wzorze ogólnym 2, w któ¬ rym Rt—R5 i A maja wyzej podane znaczenie, redu¬ kuje sie i otrzymany zwiazek w postaci diasteLreome- rycznych enancjomerów lub czystych izomerów op¬ tycznie czynnych ewentualnie rozdziela sie i otrzy¬ mana zasade ewentualnie przeprowadza w sól ad¬ dycyjna z kwasem lub z otrzymanej soli uwalnia sie zasade.
2. Sposób wedlug zastrz. 1, znamienny tym, ze jako produkt wyjsciowy stosuje sie zwiazek o wzorze ogólnym 2a, w którym Rt—R4 maja znaczenie poda¬ ne W zastrz. 1 i At oznacza grupe fenylowa lub pod¬ stawiona, w szczególnosci chlorowcem, nizsza grupe alkilowa ,nizsza grupe alkoksylowa i/lub grupa hy¬ droksylowa, grupe fenylowa. 15 20 25 30 35 40 43 5084-268 R- R. HO £ CH0H-CHR2-NH-C(R3)-CH-CH0RrA wzdR 1 R5 x^\ HO C0-CHR2-NH-C(fyjCH2-CH0RrA WZdR 2 R. HO 1^yC0-CHR-NH-C(R3)2-CH2-CH0RrA WZdR 2o PL PL PL PL PL PL
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702008654 DE2008654A1 (de) | 1970-02-25 | 1970-02-25 | Ammoathanoldenvate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL84268B1 true PL84268B1 (pl) | 1976-03-31 |
Family
ID=5763256
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1971174914A PL84395B1 (pl) | 1970-02-25 | 1971-02-24 | |
| PL1971174913A PL84268B1 (pl) | 1970-02-25 | 1971-02-24 | |
| PL1971146464A PL82843B1 (pl) | 1970-02-25 | 1971-02-24 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1971174914A PL84395B1 (pl) | 1970-02-25 | 1971-02-24 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1971146464A PL82843B1 (pl) | 1970-02-25 | 1971-02-24 |
Country Status (18)
| Country | Link |
|---|---|
| AT (3) | AT305250B (pl) |
| BE (1) | BE763408A (pl) |
| BG (3) | BG19130A3 (pl) |
| CH (4) | CH568271A5 (pl) |
| CS (3) | CS166748B2 (pl) |
| DE (1) | DE2008654A1 (pl) |
| ES (3) | ES388561A1 (pl) |
| FR (1) | FR2081541B1 (pl) |
| GB (1) | GB1340407A (pl) |
| IE (1) | IE34970B1 (pl) |
| IL (1) | IL36269A (pl) |
| NL (1) | NL7102432A (pl) |
| NO (1) | NO131983C (pl) |
| PL (3) | PL84395B1 (pl) |
| RO (3) | RO58559A (pl) |
| SE (1) | SE377561B (pl) |
| SU (2) | SU421181A3 (pl) |
| ZA (1) | ZA711204B (pl) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA791403B (en) * | 1978-04-10 | 1980-05-28 | Draco Ab | Composition of matter |
| FI70205C (fi) * | 1978-05-17 | 1986-09-15 | Degussa | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara l-/3-hydroxi-3-fenylpropyl-(2)/-/3-oxo-propyl/aminer |
| US4853381A (en) * | 1984-04-17 | 1989-08-01 | Glaxo Group Limited | Ethanolamine compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1250450B (de) * | 1962-03-31 | 1967-09-21 | Deutsche Gold- und Silber-Scheideanstalt vormals Roessler, Frankfurt/M | Verfahren zur Herstellung von Aminoalkoholen sowie deren Säureadditionssalzen und quartären Ammoniumverbindungen |
-
1970
- 1970-02-25 DE DE19702008654 patent/DE2008654A1/de active Pending
-
1971
- 1971-01-22 AT AT54671A patent/AT305250B/de not_active IP Right Cessation
- 1971-01-22 AT AT204572A patent/AT306706B/de not_active IP Right Cessation
- 1971-01-22 AT AT204672A patent/AT306707B/de not_active IP Right Cessation
- 1971-02-10 CS CS982A patent/CS166748B2/cs unknown
- 1971-02-10 CS CS3276*A patent/CS166750B2/cs unknown
- 1971-02-10 RO RO68598A patent/RO58559A/ro unknown
- 1971-02-10 CS CS3275*A patent/CS166749B2/cs unknown
- 1971-02-10 RO RO68599A patent/RO62244A/ro unknown
- 1971-02-10 RO RO65888A patent/RO60182A/ro unknown
- 1971-02-17 SU SU1752084A patent/SU421181A3/ru active
- 1971-02-17 SU SU1752085A patent/SU424349A3/ru active
- 1971-02-23 CH CH875675A patent/CH568271A5/xx not_active IP Right Cessation
- 1971-02-23 CH CH875575A patent/CH568270A5/xx not_active IP Right Cessation
- 1971-02-23 IL IL36269A patent/IL36269A/xx unknown
- 1971-02-23 CH CH258671A patent/CH568268A5/xx not_active IP Right Cessation
- 1971-02-23 CH CH875475A patent/CH568269A5/xx not_active IP Right Cessation
- 1971-02-24 NO NO679/71A patent/NO131983C/no unknown
- 1971-02-24 PL PL1971174914A patent/PL84395B1/pl unknown
- 1971-02-24 PL PL1971174913A patent/PL84268B1/pl unknown
- 1971-02-24 ZA ZA711204A patent/ZA711204B/xx unknown
- 1971-02-24 PL PL1971146464A patent/PL82843B1/pl unknown
- 1971-02-24 BG BG16892A patent/BG19130A3/xx unknown
- 1971-02-24 ES ES388561A patent/ES388561A1/es not_active Expired
- 1971-02-24 BG BG18286A patent/BG18855A3/xx unknown
- 1971-02-24 BE BE763408A patent/BE763408A/xx unknown
- 1971-02-24 NL NL7102432A patent/NL7102432A/xx unknown
- 1971-02-24 BG BG18287A patent/BG18856A3/xx unknown
- 1971-02-25 IE IE239/71A patent/IE34970B1/xx unknown
- 1971-02-25 SE SE7102409A patent/SE377561B/xx unknown
- 1971-02-25 FR FR7106442A patent/FR2081541B1/fr not_active Expired
- 1971-04-19 GB GB2245571A patent/GB1340407A/en not_active Expired
- 1971-10-20 ES ES396175A patent/ES396175A1/es not_active Expired
- 1971-10-20 ES ES396174A patent/ES396174A1/es not_active Expired
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