SU459886A3 - Способ получени -(аминофенил)алифатических карбоновых кислот или их солей - Google Patents
Способ получени -(аминофенил)алифатических карбоновых кислот или их солейInfo
- Publication number
- SU459886A3 SU459886A3 SU1815022A SU1815022A SU459886A3 SU 459886 A3 SU459886 A3 SU 459886A3 SU 1815022 A SU1815022 A SU 1815022A SU 1815022 A SU1815022 A SU 1815022A SU 459886 A3 SU459886 A3 SU 459886A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- aza
- salts
- bicyclo
- aminophenyl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/42—Oxygen atoms attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/78—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D307/56—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/66—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
Description
(54) СПОСОБ ПОЛУЧЕНИЯ а-(АМИНОФЕНИЛ)АЛИФАТИЧЕСКИХ КАРБОНОВЫХ КИСЛОТ ИЛИ ИХ СОЛЕЙ
тилэтил. Фенилен Ph, содержащий трет.-аминогруппу структурной формулы Ji в положении 2 или 3, предпочтительно в положении 4, незамещен или может содержать в остальных положени х один или несколько, предпочтительно один или два, одинаковых или неодинаковых заместителей. Последними вл ютс низший алкил, например метил, этил, н-пропил, изопропил, н-бутил или изобутил; свободные этерифицированные в простой или сложный эфир окси- или меркаптогруппы , такие, как низший алкокси-, например метокси-, ЭТОКСИ-, н-пропилокси-, изопроПИЛОКСИ- , н-бутилокси- или изобутилоксигруппа , низший алкилмеркапто-, в частности метилмеркапто- или этилмеркапто-группа; атомы галогена, например фтора, хлора или брома; трифторметилгруппы, нитро-, аминогруппы , предпочтительно ди-низший алкиламино- , в частности диметиламино-, М-этил-Мметиламино- , диэтиламино-, ди-н-пропиламиНО- , диизопропиламино-, ди-н-бутиламино- или диизобутиламиногруппы, или другие группы
со структурой А N-, а также низший алканоиламино- , например ацетиламино- или пивалоиламиногруппа, свободные или функционально модифицированные карбоксигруппы , такие, как циан, карбамоил, ди-низший алкилкарбамоил, в частности диметилкарбамоил , а также карбо-низший алкокси-, например карбометокси- или карбэтоксигруппа, или свободные или функционально модифицированные сульфогруппы, как низший алкилсульфонил , например метил- или этилсульфонил , сульфамоил, например диметилсульфамоил .
Фенилен Ph обозначает предпочтительно 1,3 (или 1,4)-фенилен, (низший алкил)-,3 (или 1,4)-фенилен, (низший алкокси)-,3 (или 1,4)-фенилен, (моно- или дигалоген)-1,3 (или ,4)-фенилен, (трифторметил)-,3 (или ,4фенилен , (амино)-1,3(или 1,4)-фенилен, (динизший алкиламино) ,3(или ,4)-фенилен или
( -1,3(или 1,4)-фенилен. Циклической третичной аминогруппой
4. ISr вл етс , например, моструктуры
V., X
ноциклическа или бициклическа низший алкиленамино- или низший алкениленаминогруппа (т. е. Ы-азациклоалк(ен)ил- или N-азабициклоалк (ен)ил), например этиленамино-, азетидино-, пирролидино-, 3-пирролинопипеРИДИНО- , 3-пиперидино-, 1,4-пентиленамино-, 2,5- или 1,6-гексиленамино- или 2,6- или 1,7гептиленаминогруппа , а также 2-аза-2-бицикло 2,2,1 гептил, 2-аза-2-бицикло 2,2,2 октил, 2-аза-2-бицикло 3,2,1 октил, 3-аза-З-бицикло 3,2,1 октил, 3-аза-З-бицикло 3,3,0 октил, 2,2аза-2-бицикло 3 ,2,2 нонил, 2-аза-2-бицикло 3,3,1 нонил, 3-аза-З-бицикло 3,2,2 нонил, 3аза-3 - бицикло 3,3,1 нонил, 2-аза-2-бицикло 4,3,0 нонил, 3-аза-З-бицикло 4,3,1 нонил, 7аза-7 - бицикло 4,3,0 нонил, 8-аза-8-бицикло
4,3,0 нонил, 2-аза-2-бицикло 4,4,0 децил или 3-аза-З-бицикло 4,4,0 деци л.
Остатком структуры может быть
V.
также моноциклическа моноокса-низшии алкилен- или монотиа-низший алкиленаминоили моно-аза-низший алкиленаминогруппа, в
которой атом азота азагруппы может быть замещен низшим алкилом, окси-низшим алкилом , фенил-низшим алкилом или фенилом, причем ароматические группы могут содержать такие же заместители, как и приведенный выше остаток фенилен.
В описанных выше группах гетероатомы отделены друг от друга по меньшей мере одним , предпочтительно двум атомами углерода . Такими остатками вл ютс , например,
пиперазино-, 4-метилпиперазино-, 4-этилпиперазино- , 4-2-оксиэтилпиперазино-, 4-бензилпиперазино- или 4-фенилпиперазино-, 3-аза-, 6гексиленамино , 3-метил-З-аза-1,6-гексиленамиНО- , 3-этил-3-аза-,6-гексиленамино-, 4-аза-,7гептиленамино- , 4-метил-4-аза-,7-гептиленамино- или 4-этил-4-аза-1,7-гептиленамино-, морфолино-, 3,5-диметилморфолино-, тетрагидро- ,3-оксазолил- или тиоморфолино-остаток .
Указанные выше циклические третичные аминогруппы могут содержать, например, приведенные дл фенилена заместители, в частности свободные или этерифицированные в простой или сложный эфир окси- или меркаптогруппы , такие, как низший алкокси- или низший алкаиоилоксигруппы или оксогруппы, а также низший алкил.
Предлагаемый способ получени соединений общей формулы I заключаетс в том, что
соединение общей формулы
Е, О О
-чI IMI
А } r-Ph-(-(-d-OH Б
R
декарбонилируют.
Декарбонилирование карбоксикарбонильной группы провод т в услови х пиролиза, предпочтительно в присутствии медного порошка .
Полученную свободную кислоту можно превратить в соль, например, взаимодействием с приблизительно стехиометрическим количестBOM аммиака, амина или гидроокиси, карбоната или гидрокарбоната щелочиого или щелочноземельного металла. Обработкой кислотой, в частности сол ной, серной или уксусной, образовавшуюс соль можно снова перевести в свободную кислоту.
Полученное соединение можно перевести в кислотно-аддитивную соль, подверга его взаимодействию , например, с органической или неорганической кислотой или с соответствуюпд ,им анионообменником. Кислотно-аддитивную соль можно превратить в свободное соединение обработкой ее основанием, например гидроокисью щелочного металла, аммиаком или гидроксиланионообменником. Фармацевтически употребл емыми атоксичными кислотно-аддитивными сол ми вл ютс , например , соли таких неорганических кислот, как сол на , бромистоводородна , серна , фосфорна , азотна или хлорна , или таких органических кислот, как муравьина , уксусна , пронионова , нтарна , гликолева , молочна , блочна , винна , лимонна , аскорбинова , малеинова , оксималеинова , пировиноградиа , фенилуксусна , бензойна , 4-аминобензойна , антранилова , 4-оксибензойна , салицилова , аминосалицилова , эмбоиова или никотинова , метансульфонова , зтаисульфонова , оксиэтансульфонова , этиленсульфонова , бензолсульфонова , галогеибеизолсульфонова , толуолсульфонова , нафталинсульфонова , сульфанилова или циклогексилсульфаминова , а также метионии, триптофан, лизин или аргинин.
Эти соли, а также никраты можно использовать также дл очистки. Например, свободные кислоты можно превратить в их соли, выделить последние из сырой смеси и затем из них получить свободные соединени .
Полученные смеси изомеров можно разделить на отдельные изомеры известным способом , например путем фракционированной дистилл ции или кристаллизации и/или хроматографии . Рацемические продукты можно расщепить на оптические антиподы, например, путем разделени диастереоизомерных солей фракционированной кристаллизацией с d- или /-ВИИИОЙ кислотой, d-cc-фенилэтиламииом, d-oc (1-иафтил)-этиламииом или 1-динхонидином.
Пример 1. 32,3 г 3-(3-хлор-4-пиперидинофеиил )-2-оксомасл ной кислоты медленно нагревают под давлением (15 мм рт. ст.) до 175°С, поддержива эту температуру до прекращени образовани окиси углерода. Приблизительно через 6 час остаток раствор ют в 300 мл 5%-ного водного раствора едкого натра, промывают диэтиловым эфиром и довод т значение рН до 5,5 сол ной кислотой, после чего приливают водный раствор гидрофосфата дикали в качестве буфера и экстрагируют диэтиловым эфиром. Органический экстракт высущивают, упаривают и остаток кристаллизуют из гексаиа. Получают 2-(3хлор-4-пиперидинофеиил ) -пропионовую кислоту , т. пл. 95-97°С. Натриева соль этой
кислоты (после перекристаллизации из диэтилового эфира) плавитс при 206-210°С, а гидрохлорнд (после перекристаллизации из смеси этанола-диэтиловый эфир) при 198- 200°С.
Исходный материал можно получить следующим образом.
Смесь 93 г З-хлор-4-нитроэтилбензола, 127 г оксалилхлорида и 300 мл сухого нитробензола кип т т 48 час с обратным холодильником и после охлаждени разбавл ют водой. Образовавщийс раствор экстрагируют диэтиловым эфиром. Получают 3-(3-хлор-4-нитрофенил )-2-оксомасл ную кислоту, которую можно дальще обрабатывать без очистки.
100 г 3-(3-хлор-4-нитрофенил)-2-оксомасл иой кислоты в 200 мл уксусной кислоты гидрируют под давлением (- 3 атм) в присутствии 3 г 10%-ного паллади на угле в качестве катализатора. По окончании поглощени водорода реакционную смесь фильтруют и фильтрат выпаривают в вакууме. Получают 3- (4-амино-З-хлорфенил) -2-оксомасл ную кислоту .
Смесь 95 г 3-(4-амино-З-хлорфенил)-2-оксомасл иой кислоты, 129 г 1,5-дибромпентана, 106 г карбоната натри и 300 мл диметилформамида нагревают 5 час при 100°С и затем упаривают досуха. Остаток раствор ют в
5%-иом водном растворе едкого натра. Остаток промывают диэтиловым эфиром и сол ной кислотой, довод т значение рН до 5, после чего экстрагируют диэтиловым эфиром, органический раствор промывают водой, высущивают и упаривают в вакууме. Получают 3- (3-хлор - 4-пиперидинофенил) -2 - оксомасл иую кислоту.
Аналогично, использу соответствующие исходные материалы, получают следующие соединеии :
а-циклопропил-:а-(4 - пиперидинофенил)-уксусна кислота, т. пл. 149-151°С (метанол); З-хлор-4-пирролидииофенилуксусна кислота , т. пл. гидрохлорида 194-19&°С (смесь метанол-простой эфир); 4-пирролидинофенилуксусна кислота, т. пл. 138-141°С; З-хлор-4морфолинофенилуксусна кислота, т. пл. 125- 126°С (смесь простой эфир-петролейный эфир);
З-хлор-4-пиперидинофенилуксусна кислота, т. пл. 106-107°С (смесь простой эфир--нетролейный эфир);
4-пиперидинофенилуксусна кислота, т. пл. ее гидрохлорида 189-193°С (изоиропапол);
а-(4-пиперидииофенил)-пропионова кислота , т. пл. 91-94°С (смесь диэтиловый эфир-петролейный эфир), т. пл. гидрохлорида 211-214°С (смесь изопропанол-простой эфир); 4-морфолинофенилуксусна кислота,
т. пл. 111-113°С (смесь этанол-простой эфир); 3-пиперидинофенилуксусна кислота, т. пл. гидрохлорида 242-245°С (вода);
а- (4-пирролидинофенил) -пропионова кислота , т. пл. 142°С (смесь простой эфир-петролейный эфир);
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US71634768A | 1968-03-27 | 1968-03-27 | |
US75713668A | 1968-09-03 | 1968-09-03 | |
US79086369A | 1969-01-13 | 1969-01-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
SU459886A3 true SU459886A3 (ru) | 1975-02-05 |
Family
ID=27418953
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU1815022A SU459886A3 (ru) | 1968-03-27 | 1969-03-25 | Способ получени -(аминофенил)алифатических карбоновых кислот или их солей |
SU1493629A SU421191A3 (ru) | 1968-03-27 | 1969-03-25 | СПОСОБ ПОЛУЧЕНИЯ ТРЕТИЧНЫХ АЛ1ИНОКИСЛОТ ИЛИ ИХ СЛОЖНЫХ ЭФИРОВ, или АМИДОВ, или их СОЛЕЙ |
SU1493628A SU419029A3 (ru) | 1968-03-27 | 1969-03-25 | Способ получения третичных аминокислотили их солей |
SU1493626A SU428600A3 (ru) | 1968-03-27 | 1969-03-25 | Способ получения третичных аминокислот или их солей |
Family Applications After (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU1493629A SU421191A3 (ru) | 1968-03-27 | 1969-03-25 | СПОСОБ ПОЛУЧЕНИЯ ТРЕТИЧНЫХ АЛ1ИНОКИСЛОТ ИЛИ ИХ СЛОЖНЫХ ЭФИРОВ, или АМИДОВ, или их СОЛЕЙ |
SU1493628A SU419029A3 (ru) | 1968-03-27 | 1969-03-25 | Способ получения третичных аминокислотили их солей |
SU1493626A SU428600A3 (ru) | 1968-03-27 | 1969-03-25 | Способ получения третичных аминокислот или их солей |
Country Status (26)
Country | Link |
---|---|
JP (1) | JPS5330712B1 (ru) |
AR (7) | AR193024A1 (ru) |
AT (8) | AT291237B (ru) |
BE (1) | BE730520A (ru) |
BG (3) | BG20340A3 (ru) |
CH (11) | CH563988A5 (ru) |
CS (8) | CS153502B2 (ru) |
CY (1) | CY809A (ru) |
DE (1) | DE1913743A1 (ru) |
DK (1) | DK145226C (ru) |
FI (1) | FI52579C (ru) |
FR (1) | FR2004827A1 (ru) |
GB (1) | GB1268831A (ru) |
IE (1) | IE33153B1 (ru) |
IL (1) | IL31861A (ru) |
KE (1) | KE2542A (ru) |
MY (1) | MY7500152A (ru) |
NL (1) | NL162647C (ru) |
NO (1) | NO132199C (ru) |
OA (1) | OA03609A (ru) |
PH (1) | PH12640A (ru) |
PL (1) | PL74820B1 (ru) |
RO (4) | RO66269A (ru) |
SE (1) | SE382812B (ru) |
SU (4) | SU459886A3 (ru) |
YU (3) | YU39926B (ru) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2025518A1 (ru) * | 1969-06-05 | 1970-12-10 | ||
DE2013376A1 (de) * | 1970-03-20 | 1971-10-07 | Merck Patent Gmbh | Substituierte Phenylessigsauren und Verfahren zu ihrer Herstellung |
-
1969
- 1969-02-17 CH CH1447271A patent/CH563988A5/xx not_active IP Right Cessation
- 1969-02-17 CH CH1446671A patent/CH563983A5/xx not_active IP Right Cessation
- 1969-02-17 CH CH1446771A patent/CH563984A5/xx not_active IP Right Cessation
- 1969-02-17 CH CH1447071A patent/CH563986A5/xx not_active IP Right Cessation
- 1969-02-17 CH CH1447371A patent/CH563989A5/xx not_active IP Right Cessation
- 1969-02-17 CH CH1446871A patent/CH554859A/xx not_active IP Right Cessation
- 1969-02-17 CH CH1396773A patent/CH559755A5/xx not_active IP Right Cessation
- 1969-02-17 CH CH1371573A patent/CH563985A5/xx not_active IP Right Cessation
- 1969-03-03 NL NL6903273.A patent/NL162647C/xx not_active IP Right Cessation
- 1969-03-18 DE DE19691913743 patent/DE1913743A1/de active Pending
- 1969-03-20 IL IL31861A patent/IL31861A/xx unknown
- 1969-03-24 SE SE6904047A patent/SE382812B/xx unknown
- 1969-03-25 SU SU1815022A patent/SU459886A3/ru active
- 1969-03-25 FR FR6908705A patent/FR2004827A1/fr active Pending
- 1969-03-25 IE IE397/69A patent/IE33153B1/xx unknown
- 1969-03-25 PL PL13255169A patent/PL74820B1/pl unknown
- 1969-03-25 SU SU1493629A patent/SU421191A3/ru active
- 1969-03-25 SU SU1493628A patent/SU419029A3/ru active
- 1969-03-25 SU SU1493626A patent/SU428600A3/ru active
- 1969-03-26 BE BE730520A patent/BE730520A/xx not_active IP Right Cessation
- 1969-03-26 AT AT281570A patent/AT291237B/de not_active IP Right Cessation
- 1969-03-26 AT AT282070A patent/AT291242B/de not_active IP Right Cessation
- 1969-03-26 CY CY809A patent/CY809A/xx unknown
- 1969-03-26 GB GB05859/69A patent/GB1268831A/en not_active Expired
- 1969-03-26 NO NO1264/69A patent/NO132199C/no unknown
- 1969-03-26 AT AT281870A patent/AT291240B/de not_active IP Right Cessation
- 1969-03-26 AT AT281770A patent/AT291239B/de not_active IP Right Cessation
- 1969-03-26 DK DK167569A patent/DK145226C/da not_active IP Right Cessation
- 1969-03-26 AT AT281370A patent/AT291235B/de not_active IP Right Cessation
- 1969-03-26 AT AT281270A patent/AT291234B/de not_active IP Right Cessation
- 1969-03-26 FI FI690885A patent/FI52579C/fi active
- 1969-03-26 AT AT298169A patent/AT287685B/de active
- 1969-03-26 AT AT281970A patent/AT291241B/de not_active IP Right Cessation
- 1969-03-27 CS CS220869A patent/CS153502B2/cs unknown
- 1969-03-27 RO RO6978690A patent/RO66269A/ro unknown
- 1969-03-27 CS CS726070A patent/CS153508B2/cs unknown
- 1969-03-27 RO RO6978689A patent/RO64901A/ro unknown
- 1969-03-27 BG BG19312A patent/BG20340A3/xx unknown
- 1969-03-27 OA OA53565A patent/OA03609A/xx unknown
- 1969-03-27 CS CS725570A patent/CS153503B2/cs unknown
- 1969-03-27 RO RO6979091A patent/RO66273A/ro unknown
- 1969-03-27 CS CS726270A patent/CS153510B2/cs unknown
- 1969-03-27 CS CS725770A patent/CS153505B2/cs unknown
- 1969-03-27 CS CS726370A patent/CS153511B2/cs unknown
- 1969-03-27 BG BG19310A patent/BG20339A3/xx unknown
- 1969-03-27 CS CS725670A patent/CS153504B2/cs unknown
- 1969-03-27 RO RO59517A patent/RO61382A/ro unknown
- 1969-03-27 CS CS725870A patent/CS153506B2/cs unknown
- 1969-03-27 BG BG19345A patent/BG20567A3/xx unknown
-
1970
- 1970-08-03 AR AR230413A patent/AR193024A1/es active
- 1970-08-03 AR AR230420A patent/AR193025A1/es active
- 1970-08-03 AR AR230412A patent/AR193194A1/es active
- 1970-08-03 AR AR230419A patent/AR192864A1/es active
- 1970-08-03 AR AR230414A patent/AR192560A1/es active
- 1970-08-03 AR AR230415A patent/AR192699A1/es active
-
1971
- 1971-05-13 AR AR235528A patent/AR194569A1/es active
-
1972
- 1972-03-23 JP JP2863972A patent/JPS5330712B1/ja active Pending
-
1973
- 1973-09-07 PH PH15001A patent/PH12640A/en unknown
-
1974
- 1974-07-17 YU YU2001/74A patent/YU39926B/xx unknown
- 1974-07-17 YU YU2000/74A patent/YU39653B/xx unknown
- 1974-08-22 CH CH238069A patent/CH566990A5/xx not_active IP Right Cessation
- 1974-11-01 CH CH238069A patent/CH563381A5/xx not_active IP Right Cessation
-
1975
- 1975-02-21 CH CH238069A patent/CH566991A5/xx not_active IP Right Cessation
- 1975-06-10 YU YU1499/75A patent/YU39532B/xx unknown
- 1975-07-10 KE KE2542*UA patent/KE2542A/xx unknown
- 1975-12-30 MY MY152/75A patent/MY7500152A/xx unknown
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5220050A (en) | Peptide mimetic compounds useful as platelet aggregation inhibitors | |
US5488064A (en) | Benzo 1,3 dioxole derivatives | |
SU651695A3 (ru) | Способ получени этерифицированных оксибензодигетероциклов или их солей, или рацематов, или оптически активных антиподов | |
LV11028B (en) | Novel benzimidazole and azabenzimidazole derivatives | |
NO144668B (no) | Uretanforbindelser med fungicid virkning. | |
SU459886A3 (ru) | Способ получени -(аминофенил)алифатических карбоновых кислот или их солей | |
Ben-Ishai et al. | The synthesis of p-substituted D, L-phenylglycines by the amidoalkylation of benzylchloride and N-benzylbenzamide | |
CH441366A (de) | Verfahren zur Herstellung von substituierten Hydrazinverbindungen | |
US3125583A (en) | Hjnc oxchaxohxchc o oh | |
CH501592A (de) | Verfahren zur Herstellung von 2-(substituierten-Benzyl)-cyanessigsäureestern | |
DK159149B (da) | Analogifremgangsmaade til fremstilling af glutaminderivater. | |
JPS5916871A (ja) | スルホンアミド系ベンズアミド類 | |
SU520913A3 (ru) | Способ получени производных 3-алкил-4-сульфамоиланилина | |
SU619098A3 (ru) | Способ получени карбоновых кислот или их минеральных,или органических солей,или сложных эфиров | |
Chosho et al. | The Reactions of N-Substituted Thioamides with α-Halonitriles | |
US2523744A (en) | Synthesis of aspartic acid | |
US4436740A (en) | 3-Cycloalkylamino-2-OR-propoxycyanopyridines | |
US3652565A (en) | Novel dibasic acid compounds and means for the production thereof | |
Tanaka et al. | Oxidation of 2, 6-piperazinediones. | |
SU501668A3 (ru) | Способ получени производных 2-аминобензиламина | |
US3577409A (en) | 2-rch2nh-4-x-5-sulfamylbenzoic acids | |
US3787569A (en) | 2-p-nitro-or p-chlorobenzamido-acetohydroxamic acid | |
SU455529A3 (ru) | Способ получени -(аминофенил)-алифатических карбоновых кислот или их производных или их солей | |
Swan et al. | Studies related to the chemistry of melanins. Part VI. Syntheses of 3-carboxypyrrole-2-acetic acid, 3, 5-dicarboxypyrrole-2-acetic acid, and related compounds | |
SU1145021A1 (ru) | Пиримидо/1,2-а/индол-2-оны в качестве промежуточных продуктов дл синтеза 10а-стирилпиримидо/1,2-а/индол-2-онов |