PL84395B1 - - Google Patents
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- PL84395B1 PL84395B1 PL1971174914A PL17491471A PL84395B1 PL 84395 B1 PL84395 B1 PL 84395B1 PL 1971174914 A PL1971174914 A PL 1971174914A PL 17491471 A PL17491471 A PL 17491471A PL 84395 B1 PL84395 B1 PL 84395B1
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- Prior art keywords
- hydroxy
- group
- hydrogen
- phenyl
- compound
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- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical class CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 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 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 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
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 17
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- -1 oxyl Chemical group 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- WQPPYOAGCWAZEI-UHFFFAOYSA-N ethylazanium;benzoate Chemical compound CC[NH3+].[O-]C(=O)C1=CC=CC=C1 WQPPYOAGCWAZEI-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BTSCBJDORATYKJ-UHFFFAOYSA-N 1-(2-chlorophenyl)propan-1-one Chemical compound CCC(=O)C1=CC=CC=C1Cl BTSCBJDORATYKJ-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000001145 hydrido group Chemical group *[H] 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 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
- 229910052697 platinum 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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- 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 wytwarza¬ nia nowych l-hydróksyfenylo-l-hydroksy-2-(3-ary- lo-3-'hydroksypropylo)-aminoetanów w postaci ra- cematu ewentualnie diastereomerycznych enancjo- merów, czystych izomerów optycznie czynnych oraz ich soli addycyjnych z kwasami.Nowym zwiazkom odpowiada wzór ogólny 1, w którym Rj oznacza wodór lub nizsza grupe alkir- lowa lub alkoksylowa, R2 oznacza wodór, grupe metylowa lub etylowa, R3 oznacza wodór lub gru¬ ipe metylowa, R4 oznacza wodór lub grupe hyd¬ roksylowa i A oznacza ewentualnie podstawiona chlorowcem, nizsza grupa alkilowa, nizsza grupa alkoksylowa i/lub grupa hydroksylowa grupe feny- lowa lub skondensowana dwucyklaczna grupe, w ^której pierscien nie zwiazany bezposrednio z alifa¬ tycznym lancuchem, jest izocykliczny lufo hetero¬ cykliczny i nasycony lub aromatyczny. Jako dwucykliczne grupy tego rodzaju mozna wymie¬ nic np. grupe naftylowa, 3,4-metylenodwuoksyfeny- lowa i benzodioksanylowa.Wedlug wynalazku nowe zwiazki wytwarza sie przez redukcje zwiazku o wzorze ogólnym 2, w (którym Rt—R4 i A maja wyzej podane znaczenie, a B oznacza atom tlenu lub ugrupowanie o wzo¬ rze 3.W przypadku, gdy B oznacza atom tlenu, w cza¬ sie reakcji jednoczesnie zredukowane sa obie gru¬ py karfoonylowe. Jako srodek redukujacy stosuje sie wodór i znane katalizatory, np. nikiel, platyne lub pallad, albo kompleksowe wodorki, zwlaszcza borowodorek sodowy.Otrzymane p:*jdukty ewentualnie, rozdziela sie w znany sposób w optycznie czynne formy lub ewentualnie na diastereomeryczne enancjomery i/lub przeprowadza w sole addycyjne z kwasami.Zwiazki wyjsciowe wytwarza sie znanymi me¬ todami otrzymywania takich zwiazków.Otrzymywane sposobem wedlug wynalazku zwiazki znajduja zastosowanie w terapii. Nadaja sie one szczególnie jako substancje czynne w srod¬ kach nasercowych i stosowanych w chorobach krazeniowych. Stosowanie zachodzi w postaci zna¬ nych galenowych preparatów, zawierajacych znane srodki pomocnicze i nosniki, np. w postaci table¬ tek, drazetek, kapsulek, areozoli, kropli i roztwo¬ rów iniekcyjnych. Dawka jednostkowa wynosi przy tym okolo 0,1 — okolo 20 mg.Nastepujace przyklady wyjasniaja blizej wyna¬ lazek, nie ograniczajac jego zakresu. Wydajnosc podana jest kazdorazowo w % wydajnosci teore¬ tycznej.Przyklad I. l-(4-hydróksyfenylo)-1-hydroksy- -2- [ (3-fenylo-3-hydroksy) ipropylo]-aminoetan 7,2 g p^benzyloksy-ctHbromoacetofenonu wprowa¬ dza sie w reakcje z 12 g w^benzylo-aminopropio- fenonu w acetonitrylu, usuwa bromowodorek-w- -benzyloamijno-propiofenonu i utworzony l-(4-iben- zyloksy)-l-keto-2-[(3-fenylo-3-keto)-propylo] - ami¬ noetan uwodornia sie w metanolu w obecnosci 84 39584 395 3 niklu Raneya, az zostana zredukowane obie grupy karbonylowe, odszczepiona grupa benzylowa i pow¬ stanie 1 ^(4-hydroksyfenylo)-1-hydroksy-2-[(3-fenylo- -3-hydroksy)-propylo]-aminoetan. Rozdzielenie dias- tereomerów w znany sposób prowadzi do otrzy¬ mania postaci X, o temperaturze topnienia 158°C, postaci Y, o temperaturze topnienia 112°C.Przyklad II. erytro-Jl -(4-hydroksyfenylo)-1- -hydroksy-2-metylo-2-[(3-fenylo- 3 -hydroksy) - pro¬ pylo]-aminoetan 26,0 g l-(4-foenzyloksyfenylo)-l-hydroksy-2-amino- propanu wprowadza sie w reakcje z 16,8 g oj-chlo- ropropiofenonu w acetonitrylu, w obecnosci sody.Otrzymamy 1-(4-foenzyloksyfenylo)-1-hydroksy-2- metylo-2- [(3-fenylO|-3-keto)-propylo]-aminoetan u- wodornra si^ w obecnosci niklu Raneya do erytro- ¦ -l-(4-hyc^oJ^ytenylo)-il-hydroksy-2-metylo- 2 - [(3- -fenylo-3-hydroksy) -propylo] -aminoetanu. Chloro¬ wodorek topnieje w temperaturze 186°C.Odpowiednio do podanych przykladów wytwarza sie nastepujace zwiazki: Benzoesan l-i(3-hy nylo-3-hydroksy)-propylo]-aminoetanu, o tempera¬ turze topnienia: 128°C, chlorowodorek treo-1-(4-hydroksyfenylo)-!-hydrok- sy-2Hmetylo-2-[(3-fenylo-3-hydroksy)-propylo] - ami- noetanu, o temperaturze topnienia 160°C, 1-(4-hydroksy-3Hmetoksyfenylo)-l-hydroksy - 2 - [3- -fenylo-3-hydroksy)-propylo]-aminoetan, postac X: zasada topnieje w temperaturze 162°C, siarczan, temperatura topnienia: 163°C, .JhydrOksy-2-!metyio-i2-[ (3-fenylo-3-hydroksy] - pro- l-(3,5-dwuhydroksyfenylo)- 1-hydroksy- 2-[(3-feny- lo-3-hydroksy)-propylo]-aminoetan, postac X: tem¬ peratura topnienia: 187°C, postac Y: temperatura topnienia: 162°C, benzoesan 1-(3,5-dwuhydroksyfenylo)-!-hydroksy-2- -[(3-feny10'-3-hydroksy-l,l-dwumetylo)-propylo] - a- minoetanu, postac X: temperatura topnienia: 109PC, postac Y: temperatura topnienia: 142°C (hydrat), Chlorowodorek 1-(3,5-dwuhydroksyfenylo) -1 -hydro- ksy-2-[(3-a-naftylolo-3-hydroksy - 1,1 -dwumetylo)- -propylo]-aminoetanu, postac X: temperatura top¬ nienia: 235QC, postac Y: temperatura topnienia: 149^, benzoesan 1^(4-hydiroksy-2-metylofenylo) -1 -hydrok¬ sy-2- [(3-o-metylofenylo-3-hydroksy)-propylo] - ami¬ noetanu, o temperaturze topnienia: 164°C, l-(4-hydroksy-2-metylofenylo)-l-hydroksy - 2 - [(3- -lp-fmetoksyfenylo-3-hydroksy)-propylo] - aiminoetan, o temperaturze topnienia: 161°C, l-(4-hydrroksy-2-metyiofenylo)-1-hydroksy - 2 - [(3- -p-hydroksy-m-chlorofenylo-3-hydroksy) - propylo]- -aminoetan, postac X: temperatura topnienia: 161°C (chlorowodorek), postac Y: temperatura top- nienia 81°C (benzoesan), l-(4-hydroksy-3Jbutoksyfenylo)-l-hydroksy - 2 -[(3- -m,p-dwuetoksyfenylo-3-hydroksy) - propylo] - ami¬ noetan, zasada: temperatura topnienia: 108°C, ben¬ zoesan: temperatura topnienia: 128qC, chlorowodo- rek: temperatura topnienia: 125°C, siarczan: tem¬ peratura topnienia: 172°C, benzoesan 1-'(4-hydroksy-34utoksyfenylo)-1-hydro¬ ksy- 2-[(3-m,p-dwubutoksyfenylo- 3-hydroksy)-pro- pylo]-aiminoetanu, temperatura topnienia: 101°C, erytro-1-(4-hydroksyfenylo)^1-hydroksy - 2 - mety¬ lo-2-[(3-fenylo-3-hydroksy)-propylo] - aminoetan, temperatura topnienia: 186qC. PL PL PL PL PL PL
Claims (2)
1. Zastrzezenia pa t e n t o we 1. Sposób wytwarzania nowych 1-hydroksyfenylo- -1-hydroksy-2-(3-arylo-3-hydroksyp!ropylo) - amino¬ etanów o wzorze ogólnym 1, w którym Rx oznacza wodór lub nizsza grupe alkilowa lub alkoksylowa, 25 R2 oznacza wodór, grupe metylowa lub etylowa, R3 oznacza wodór lub grupe metylowa, R4 oznacza wodór lub grupe hydroksylowa i A oznacza ewen¬ tualnie podstawiona chlorowcem, nizsza grupe alki¬ lowa, nizsza grupe alkoksyilowa i/lub grupe hy- 30 droksylowa, grupe fenylowa lub skondensowana dwucykliczna grupe, w której pierscien niezwia- zany bezposrednio z alifatycznym lancuchem, jest izocykliczny lub heterocykliczny i nasycony lub aromatyczny, w postaci racematu ewentualnie dia- 35 stereomerycznych enancjomerów lub czystych, op¬ tycznie czynnych izomerów, znamienny tym, ze zwiazek o wzoirze ogólnym 2, w którym Rt—R4 i A maja wyzej podane znaczenie, a B oznacza atom. tlenu lub ugrupowanie o wzorze 3, redukuje sie 40 i otrzymany zwiazek ewentualnie rozdziela sie na diastereomeryczne enancjomery lub czyste, optycz¬ nie czynne izomery i otrzymana zasade ewentual¬ nie .przeprowadza sie w sól addycyjna z kwasem lufo z otrzymanej soli uwalnia zasade. 45
2. Sposób wedlug zastrz. 1, znamienny tym, ze jako produkt wyjsciowy stosuje sie zwiazek o wzo¬ rze ogólnym 2a, w którym Rj—R3 i B maja zna¬ czenie podane w zastrz. 1 i Aj oznacza grupe feny¬ lowa lub, w szczególnosci podstawiona chlorow- 50 cem, nizsza grupa alkilowa, nizsza grupa alkoksy¬ lowa i/lub grupa hydroksylowa, grupe fenylowa.84 395 HO CHOH-CHR-NH-C(RA-CH-CHOH-A WZdR 1 R HO 1^ ^C-CHR-NH-C(R3)2-CH2-C0-A B WZÓR 2 R HO 1^^3"C-CHRrNH-C(R3)rCH2-C0^A1 B WZdR 2a ^^OH WZdR 3 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 |
|---|---|
| PL84395B1 true PL84395B1 (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 | |
| PL1971146464A PL82843B1 (pl) | 1970-02-25 | 1971-02-24 | |
| PL1971174913A PL84268B1 (pl) | 1970-02-25 | 1971-02-24 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1971146464A PL82843B1 (pl) | 1970-02-25 | 1971-02-24 | |
| PL1971174913A PL84268B1 (pl) | 1970-02-25 | 1971-02-24 |
Country Status (18)
| Country | Link |
|---|---|
| AT (3) | AT306706B (pl) |
| BE (1) | BE763408A (pl) |
| BG (3) | BG18856A3 (pl) |
| CH (4) | CH568268A5 (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 AT204572A patent/AT306706B/de not_active IP Right Cessation
- 1971-01-22 AT AT204672A patent/AT306707B/de not_active IP Right Cessation
- 1971-01-22 AT AT54671A patent/AT305250B/de not_active IP Right Cessation
- 1971-02-10 CS CS982A patent/CS166748B2/cs unknown
- 1971-02-10 CS CS3275*A patent/CS166749B2/cs unknown
- 1971-02-10 RO RO68598A patent/RO58559A/ro unknown
- 1971-02-10 RO RO65888A patent/RO60182A/ro unknown
- 1971-02-10 RO RO68599A patent/RO62244A/ro unknown
- 1971-02-10 CS CS3276*A patent/CS166750B2/cs unknown
- 1971-02-17 SU SU1752084A patent/SU421181A3/ru active
- 1971-02-17 SU SU1752085A patent/SU424349A3/ru active
- 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 CH875575A patent/CH568270A5/xx not_active IP Right Cessation
- 1971-02-23 CH CH875675A patent/CH568271A5/xx not_active IP Right Cessation
- 1971-02-23 CH CH875475A patent/CH568269A5/xx not_active IP Right Cessation
- 1971-02-24 NL NL7102432A patent/NL7102432A/xx unknown
- 1971-02-24 BG BG018287A patent/BG18856A3/xx unknown
- 1971-02-24 ZA ZA711204A patent/ZA711204B/xx unknown
- 1971-02-24 PL PL1971174914A patent/PL84395B1/pl unknown
- 1971-02-24 BG BG016892A patent/BG19130A3/xx unknown
- 1971-02-24 ES ES388561A patent/ES388561A1/es not_active Expired
- 1971-02-24 BE BE763408A patent/BE763408A/xx unknown
- 1971-02-24 PL PL1971146464A patent/PL82843B1/pl unknown
- 1971-02-24 PL PL1971174913A patent/PL84268B1/pl unknown
- 1971-02-24 NO NO679/71A patent/NO131983C/no unknown
- 1971-02-24 BG BG018286A patent/BG18855A3/xx unknown
- 1971-02-25 FR FR7106442A patent/FR2081541B1/fr not_active Expired
- 1971-02-25 IE IE239/71A patent/IE34970B1/xx unknown
- 1971-02-25 SE SE7102409A patent/SE377561B/xx unknown
- 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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