SU428597A3 - СПОСОБ ПОЛУЧЕНИЯ р-АРИЛ-2-АМИНОАЛКОКСИСТИРОЛОВ - Google Patents
СПОСОБ ПОЛУЧЕНИЯ р-АРИЛ-2-АМИНОАЛКОКСИСТИРОЛОВInfo
- Publication number
- SU428597A3 SU428597A3 SU1701179A SU1701179A SU428597A3 SU 428597 A3 SU428597 A3 SU 428597A3 SU 1701179 A SU1701179 A SU 1701179A SU 1701179 A SU1701179 A SU 1701179A SU 428597 A3 SU428597 A3 SU 428597A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- radical
- lower alkyl
- substituted
- compounds
- aminoaloxystyrols
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 239000000203 mixture Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 238000001640 fractional crystallisation Methods 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 2
- WJYNWFSNRMEPMF-UHFFFAOYSA-N 2-[2-(diethoxyphosphorylmethyl)phenoxy]-N,N-dimethylethanamine Chemical compound CN(CCOC1=C(CP(OCC)(OCC)=O)C=CC=C1)C WJYNWFSNRMEPMF-UHFFFAOYSA-N 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000005429 oxyalkyl group Chemical group 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 150000003008 phosphonic acid esters Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OGBVRMYSNSKIEF-UHFFFAOYSA-N Benzylphosphonic acid Chemical compound OP(O)(=O)CC1=CC=CC=C1 OGBVRMYSNSKIEF-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- AYLIEDQYYJIGDP-UHFFFAOYSA-N [C]1=CC=CS1 Chemical compound [C]1=CC=CS1 AYLIEDQYYJIGDP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000002474 dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- -1 trifluoro, methyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- 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
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/18—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with unsaturation outside the aromatic ring
- C07C39/19—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with unsaturation outside the aromatic ring containing carbon-to-carbon double bonds but no carbon-to-carbon triple bonds
- C07C39/20—Hydroxy-styrenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
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- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Biochemistry (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Furan Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
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Description
Изобретение относитс к способу получени новых р-арил-2-аминоалкокоистиролов, которые обладают ар-макологической активностью и могут .найти дрименение в фармацевтической промышленности.
Получение этих соединений основано на известной реакции В.иттига, согласно которой Т1|ри взаимодействии алкилиденфосфоранов с карбонильньгми соединеии ми получают различные замещенные этиленовые производные.
Использование этой реакции в данном способе позвол ет получ.ить новые не описанные ранее соединени , обладающие фармакологи-, ческой активностью.
В соответствий с изобретением получают новые р-арил-2-аминоалкОКсистиролы общей формулы I
R Аг
:c c-JyR
R, 0-СН-СН-(СН.2)-КС Кц. К
или .их соли с иеоргаиическими и органическими кислотами.
В формуле I Аг обоз-начает фениловый радикал , 2-, ИЛИ 3-, или 4-пи,ридиловый радикал, который может быть замещен низщей алкильной группой, 2-,хинолиловый 1или 2-пиразин«ловый радикал, который может быть замещен низшим алкило.м, 2-бензимидазолильный радикал , который может быть замещен атомом
галогена, н«зщим алкилом или трифтор,метильной группой, 2-фурил- или 2-тиенИловый радикал, 5-изоксазолиловый радикал, который .может быть замещен низшим алкильным ил« фенильным радикалом, 5-(1,2,4-оксадиазолил )-радикал, замещенный при .необходимости .низщим алкилом;
RI, R2, R4 и Rs, Которые могут быть одинаковыми НЛИ различными, обозначают атомы водорода или низщие алкильные радикалы;
Ra - атом водорода, низща алкоксигруппа;
R6 и R7, которые могут быть одинаковыми ил.и различными, обозначают атомы водорода ИЛ.И низщие алкил-, алкенил-, оксиалкил-, алкоксиалкиловые или аралкиловые радикалы, причем радикалы Re и Rv вместе с наход щимс между ними атомо.м азота могут образовывать насыщенное моноцикл.ическое, гетероцикличеакое 5-7-членное кольцо, которое .может. содержать атом кислорода или атом азота,
п - число О или 1.
Согласно изобретению новые соединени формулы I получают путем реакции обменного разложени эфира фосфоновой кислоты общей формулы II C P(GR,), н-с(ч O-CH-CH- CHJ N Кч RS В .которой радикалы Rz-R и п имеют указаиные значени и Rs низший алкильный радикал , с альдегидом или кетоно-.м общей формулы III Аг - С О , кото.рой Аг и RI Имеют указанные значени , в присутствии основани при дромел уточн.ом .образовании карбаниона соединени формулы II. В качестве основани примен ют гидРиды щелочного металла. Реакщию провод т в растворителе; в качестве растворител используют высококип щие простые эф.иры, например диоксан. Реакцию обменного разложени можно проводить « iB содержащем воду растворителе, например смеси метанола и воды в присутствии неоргаи ич ее кого основа.ни . Целесообразно сначала к эфиру фосфоиовой кислоты общей формулы II прибавл ть гидрид щелоч.иого металла. После окончани выделени водорода без предварительного выделени образававщегос при этом карбаниоиа к соединению формулы II доба.вл ют альдегид или Кетон формулы III. Реакцию провод т П:ри слегка повыщенных температурах между 30 и 60° С. Соединени формулы I образуютс в В|Иде смеси их цис- и т/оанс-изомеров. Если радикалы RI и Rg вл ютс атомами водоро.да, то преимущественно образуютс гра с-соединени . Цис- и транс-соединенИЯ могут быть разделены путем фракционной кристаллизации. Соединени формулы I могут быть переведены в соли с помощью неорганических или органическ}их кислот. -В качестве кислот используютс сол на , бромистоводородиа , серна , фосфорна , винна , -толуолсульфонова кислоты. :П р и м е р 1. 2,0 г гидрида натр.и суспендируют в 50 мл абсолютного диоксана и при хорошем размещивании в течение 15 мин при 28° С вкапывают раствор из 6,3 г диэтилового эфира 2- (2-диметиламиноэтокси) -бензилфосфоновой кислоты; наблюдают умеренное выделеиие водорода. Размвщивают еще в течение I час ,и затем .в течение 15 мин ввод т по капл м раствор 2,14 г пиридин-З-альдегида в 20 мл абсолютного диоксана, причем оп ть наблю.даетс выделевие газа. После сто ни в течение 5-10 час реакциоииый продукт разлагают льдом и экстрагируют хлороформом . После удалени дистилл цией растворител остаетс светло-коричневое масло. Его раст1вор ют в этаноле и осаждают гидрохлорид эфирного раствора сол ной кислотой, затем перекристаллизовывают. Получают 3,0 г (соответствует 44 7о теории) (2-диметиламиноэтокси )-стир/ил - пириди.н - дигидрохлорида в виде светло-желтых кристаллов с т. пл. 238° С. Пример 2. Пз диэтилового эфира 2- (.2диметиламиноэтокои ) -бензилфосфоиовой кислоты (т. кип. 140-148° С) и 2,7-нафтопиридии-2-альдегида получают (2-диметиламиноэтокси )-стирил - 2,7-нафтопиридин - дигидрохлорид (т. ил. 197° С, выход 24% теории ). (Пример 3. Из диэтилового эфира 2-(2диметиламиноэтакси )-бензилфосф0новой кислоты (т. кип. 140-148° С) и пиридин-2-альдегида получают (2-димeтилaминoэтoкicи)cт .иpил - пиридин - моногидрохлорид (т. пл. 183° С; выход 52% теории). Пример 4. Из диэтилового эфира 2-(2диметиламииоэтокси ) -беизилфаофоновой кислоты (т. кип. 140- l48°C) и хи.нолин-2-альдегида получают (2-.диметиламиноэтокси)стирил -хинолии - моногидрохлорид (т. пл. 188°С; 1выход 48% теории). Пр,И1мер 5. Из диэтилового эфира 2-(2диметиламиноэтокси ) -бензилфосфоновой кислоты (т. кип. 140-148° С) и бензальдегида получают 2-(2-димет.иламиноэтокси)-стильбенпидрохлорид (т. пл. 199° С; выход 61% теории ). Предмет изобретени 1. Способ получени р-арил-2-аминоалкоксистиролов общей формулы I R I-CH-CH-CCH VI CI Tttj. Из где Аг - фенил, 2-, 3- «ли 4-пиридиловый радикал , который может быть замещен низшим алкилом, 2-:хинолиловый или 2-(Пиразиииловый радикал, который может быть замещен низшим алкилом, пиримидиловый радикал, который может быть замещен иизщим алкилом, 2-бензимидазолильный радикал, который может быть замещен атомом галогена, иизщим алкилом или трифторметильной группой, 2фурил- , 2-тиениловый радикал, 5-изоКсазоли ловый радикал, который может быть замещен низшим алкилом или фенилом, 5-(1,2,4-оксадиазолил )-радикал, который может быть замещен низшим алкилом; RI, R2, R4. Rs - о.динаКО1Вые или различные - водород или алкил; Ra - водород или алкожсигруппа;
Re и R7 - одинаковые или различные -.зодород , алкил-, алкеиил-, оксиалкил-, алкоксиалкиловый или аралкиловый радикалы, причем радикалы Re и R вместе с наход щимс между ними атомом азота .могут образовывать насыщенное моноциклическое, 5-7-членное гетероциклическое кольцо, которое может содержать атом кислорода, атом азота;
п - Ч.ИСЛО О или 1,
отличающийс тем, что эфир фосфоновой кислоты общей формулы II
Р(ОКз).,
С4
Rb
,/
0-СН-С11-(СН2)л N
г I IR
Tixj US
пде R2-Ry и п имеют указа« ые значени и Rs - низший алкильный радикал, подвергают взаИ1Модейст1вию с альдегидом иди Кетоном общей формулы III
RI
Claims (3)
- IАг-С -О,где Аг и RI имеют указанные значени , с последующим .выделением целевого иродукта в свободном виде ил.и в виде соли.
- 2.Способ по п. 1, отличающийс тем, что процесс ведут п.р.и температуре 30-60° С.
- 3.Сиособ по п. 1, отличающийс тем, что смесь цис- и гра с-изомеров целевого продукта раздел ют, например фракционной кристаллизацией .
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Application Number | Priority Date | Filing Date | Title |
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DE1939809A DE1939809B2 (de) | 1969-08-05 | 1969-08-05 | ß-Aryl-2-aminoalkoxy-styrole und Verfahren zu ihrer Herstellung |
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Publication Number | Publication Date |
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SU428597A3 true SU428597A3 (ru) | 1974-05-15 |
Family
ID=5741970
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Application Number | Title | Priority Date | Filing Date |
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SU1701181A SU432712A3 (ru) | 1969-08-05 | 1970-07-28 | |
SU1701190A SU450398A3 (ru) | 1969-08-05 | 1970-07-28 | Способ получени -арил-2аминоалкоксистиролов |
SU1701179A SU428597A3 (ru) | 1969-08-05 | 1970-07-28 | СПОСОБ ПОЛУЧЕНИЯ р-АРИЛ-2-АМИНОАЛКОКСИСТИРОЛОВ |
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SU1701181A SU432712A3 (ru) | 1969-08-05 | 1970-07-28 | |
SU1701190A SU450398A3 (ru) | 1969-08-05 | 1970-07-28 | Способ получени -арил-2аминоалкоксистиролов |
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JP (6) | JPS4941433B1 (ru) |
KR (1) | KR780000113B1 (ru) |
AT (5) | AT302346B (ru) |
BE (1) | BE754405A (ru) |
BG (6) | BG18600A3 (ru) |
CH (6) | CH548367A (ru) |
CS (6) | CS170535B2 (ru) |
DE (1) | DE1939809B2 (ru) |
DK (1) | DK139717B (ru) |
ES (6) | ES382425A1 (ru) |
FI (1) | FI54912C (ru) |
FR (1) | FR2068463B1 (ru) |
GB (1) | GB1307436A (ru) |
HU (1) | HU163185B (ru) |
IE (1) | IE34634B1 (ru) |
IL (1) | IL35047A (ru) |
NL (1) | NL7011590A (ru) |
NO (1) | NO135243C (ru) |
PH (1) | PH9520A (ru) |
PL (2) | PL93130B1 (ru) |
RO (5) | RO57548A (ru) |
SE (1) | SE382211B (ru) |
SU (3) | SU432712A3 (ru) |
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Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS50139537A (ru) * | 1974-04-25 | 1975-11-07 | ||
US4220603A (en) * | 1977-10-07 | 1980-09-02 | Mitsubishi Chemical Industries, Limited | Pharmaceutically active (omega-aminoalkoxy)bibenzyls |
JPS6045632B2 (ja) * | 1978-03-09 | 1985-10-11 | 三菱化学株式会社 | ω−アミノアルコキシスチルベン類及びその酸付加塩 |
DE2818765A1 (de) | 1978-04-28 | 1979-11-08 | Basf Ag | Aminoderivate des 2-methyl-5-(2-hydroxystyrol)-1,3,4-thiadiazols |
DE2818998A1 (de) * | 1978-04-29 | 1979-11-15 | Basf Ag | 3-alkyl-5-(2-hydroxy-styryl)-isoxazole und verfahren zu ihrer herstellung |
DE2818999A1 (de) * | 1978-04-29 | 1979-11-15 | Basf Ag | Aminoderivate von 3-alkyl-5-(2- hydroxystyryl)-isoxazolen |
JPS5629548A (en) * | 1979-08-16 | 1981-03-24 | Mitsubishi Chem Ind Ltd | Omega-aminoalkoxystilbenes and their acid addition salts |
DE2943405A1 (de) | 1979-10-26 | 1981-05-07 | Basf Ag, 6700 Ludwigshafen | Neue aminoderivate des 5-(2-hydroxystyryl)-isoxazols |
DE2943406A1 (de) | 1979-10-26 | 1981-05-07 | Basf Ag, 6700 Ludwigshafen | Aminoderivate des 2-methyl-5-(2-hydroxystyryl)-1,3,4-thiadiazols |
DE3006809A1 (de) * | 1980-02-23 | 1981-09-24 | Basf Ag, 6700 Ludwigshafen | 2-((3-amino-2-hydroxy-propoxy)-styryl)-isoxazole, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen |
JPS5874379U (ja) * | 1981-11-16 | 1983-05-19 | 富士通株式会社 | 電子装置 |
NO174506B (no) * | 1984-10-30 | 1994-02-07 | Usv Pharma Corp | Analogifremgangsmaate ved fremstilling av terapeutisk aktive forbindelser |
BR112013030599A2 (pt) | 2011-06-10 | 2016-09-27 | Procter & Gamble | núcleo absorvente para artigos absorventes descartáveis |
US9468566B2 (en) | 2011-06-10 | 2016-10-18 | The Procter & Gamble Company | Absorbent structure for absorbent articles |
JP2014515983A (ja) | 2011-06-10 | 2014-07-07 | ザ プロクター アンド ギャンブル カンパニー | 使い捨ておむつ |
EP2740449B1 (en) | 2012-12-10 | 2019-01-23 | The Procter & Gamble Company | Absorbent article with high absorbent material content |
PL3254656T3 (pl) | 2013-06-14 | 2022-01-10 | The Procter & Gamble Company | Wyrób chłonny i wkład chłonny tworzący kanały w stanie mokrym |
US9987176B2 (en) | 2013-08-27 | 2018-06-05 | The Procter & Gamble Company | Absorbent articles with channels |
EP3351225B1 (en) | 2013-09-19 | 2021-12-29 | The Procter & Gamble Company | Absorbent cores having material free areas |
EP2886092B1 (en) | 2013-12-19 | 2016-09-14 | The Procter and Gamble Company | Absorbent cores having channel-forming areas and c-wrap seals |
-
0
- BE BE754405D patent/BE754405A/xx unknown
-
1969
- 1969-08-05 DE DE1939809A patent/DE1939809B2/de active Granted
-
1970
- 1970-07-21 FI FI2035/70A patent/FI54912C/fi active
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- 1970-07-22 RO RO65937A patent/RO58837A/ro unknown
- 1970-07-28 SU SU1701181A patent/SU432712A3/ru active
- 1970-07-28 SU SU1701190A patent/SU450398A3/ru active
- 1970-07-28 SU SU1701179A patent/SU428597A3/ru active
- 1970-07-30 KR KR7001068A patent/KR780000113B1/ko active
- 1970-07-31 CS CS3511*[A patent/CS170535B2/cs unknown
- 1970-07-31 CS CS5391A patent/CS170533B2/cs unknown
- 1970-07-31 CS CS3514*[A patent/CS170538B2/cs unknown
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- 1970-07-31 CS CS3510*[A patent/CS170534B2/cs unknown
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- 1970-08-03 HU HUTO819A patent/HU163185B/hu unknown
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- 1970-08-04 ES ES382425A patent/ES382425A1/es not_active Expired
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- 1970-08-04 ES ES382427A patent/ES382427A1/es not_active Expired
- 1970-08-04 ES ES382430A patent/ES382430A1/es not_active Expired
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1973
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1978
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