SU421191A3 - СПОСОБ ПОЛУЧЕНИЯ ТРЕТИЧНЫХ АЛ1ИНОКИСЛОТ ИЛИ ИХ СЛОЖНЫХ ЭФИРОВ, или АМИДОВ, или их СОЛЕЙ - Google Patents

СПОСОБ ПОЛУЧЕНИЯ ТРЕТИЧНЫХ АЛ1ИНОКИСЛОТ ИЛИ ИХ СЛОЖНЫХ ЭФИРОВ, или АМИДОВ, или их СОЛЕЙ

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Publication number
SU421191A3
SU421191A3 SU1493629A SU1493629A SU421191A3 SU 421191 A3 SU421191 A3 SU 421191A3 SU 1493629 A SU1493629 A SU 1493629A SU 1493629 A SU1493629 A SU 1493629A SU 421191 A3 SU421191 A3 SU 421191A3
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USSR - Soviet Union
Prior art keywords
amides
salts
altiino
acides
obtaining tertiary
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SU1493629A
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English (en)
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Рихард Виллиам Джеймс Карней , Джордж Стивене
Иностранна фирма Циба Гейги Швейцари
ФОНД зное
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    • C—CHEMISTRY; METALLURGY
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pain & Pain Management (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Rheumatology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pyrrole Compounds (AREA)

Description

1
Изобретение относитс  к получению физиологически активных соединений, которые могут найти применение в фармацевтической практике.
Использование известной в органической химии реакции взаимодействи  галоидангидридов кислот с диазометаном и известных реакций гидролиза, алкоголиза, аммонолиза или аминолиза диазокетонов применительно к галоидоангидридам замещенных ароматических кислот дало возможность получить новые соединени  - третичные аминокислоты, а также их производные: сложные эфиры, амиды с высокой биологической активностью.
Предлагаемый способ получени  третичных аминокислот общей формулы
Rt
I
AN-Ph-CH-COOH,
где RI - водород, низщий алкил, алкенил, циклоалкил, циклоалкенил или циклоалкил - низший алкил;
Ph - замещенна  или незамещенна  фениленгруппа;
А - низший алкилен, алкенилен, аза-алкилен , окса-алкилен; тиа-алкилен, причем два имеющихс  гетероатома отделены друг от друга по меньшей мере одним атомом углерода .
2
или их сложных эфирОБ, или амидов, или их солей, заключаетс  в том, что соединение общей формулы
,. О
AN-Ph-Cr ,
R
где Ph и А имеют -указанные значени ; R2 - галоид,
подвергают взаимодействию с диазометансоединение .м общей формулы
R,-CH:rzN-N,
где RI имеет указанное значение.
Полученный таким образом диазокетон подвергают гидролизу, или алкоголизу, или аммонолизу , или а.минолизу с последующим выделением целевого продукта в виде основани  или переведением его в соль известным способом . При необходимости полученную смесь
изомеров раздел ют на отдельные изомеры.
Пример 1. К раствору 2,1 г 4-(3-пирролин-1-ил )-бензоилхлорида в минимальном
количестве этиленхлорида прибавл ют по
капле при перемешивании и 5-10° просто эфирный раствор диазометана до тех пор, пока не останетс  желта  окраска. После 3-час сто ни  при 20-25° реакционную с.месь выпаривают под уменьшенным давлением. Остаток раствор ют приблизительно в 20 мл ди
SU1493629A 1968-03-27 1969-03-25 СПОСОБ ПОЛУЧЕНИЯ ТРЕТИЧНЫХ АЛ1ИНОКИСЛОТ ИЛИ ИХ СЛОЖНЫХ ЭФИРОВ, или АМИДОВ, или их СОЛЕЙ SU421191A3 (ru)

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
SU421191A3 true SU421191A3 (ru) 1974-03-25

Family

ID=27418953

Family Applications (4)

Application Number Title Priority Date Filing Date
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
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

Family Applications Before (3)

Application Number Title Priority Date Filing Date
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
SU1815022A SU459886A3 (ru) 1968-03-27 1969-03-25 Способ получени -(аминофенил)алифатических карбоновых кислот или их солей

Country Status (26)

Country Link
JP (1) JPS5330712B1 (ru)
AR (7) AR192699A1 (ru)
AT (8) AT291242B (ru)
BE (1) BE730520A (ru)
BG (3) BG20567A3 (ru)
CH (11) CH563984A5 (ru)
CS (8) CS153506B2 (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) RO66273A (ru)
SE (1) SE382812B (ru)
SU (4) SU419029A3 (ru)
YU (3) YU39653B (ru)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
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

Also Published As

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IE33153B1 (en) 1974-04-03
DK145226C (da) 1983-03-28
AT291239B (de) 1971-07-12
RO64901A (fr) 1979-08-15
AR193194A1 (es) 1973-04-11
CH559755A5 (ru) 1975-03-14
AT291241B (de) 1971-07-12
BE730520A (ru) 1969-09-26
CH563985A5 (ru) 1975-07-15
NO132199C (ru) 1975-10-08
YU200074A (en) 1982-06-30
SE382812B (sv) 1976-02-16
DE1913743A1 (de) 1969-11-20
SU459886A3 (ru) 1975-02-05
CH566990A5 (ru) 1975-09-30
FI52579C (fi) 1977-10-10
NL6903273A (ru) 1969-09-30
CS153502B2 (ru) 1974-02-25
CS153510B2 (ru) 1974-02-25
YU200174A (en) 1982-06-30
FR2004827A1 (ru) 1969-12-05
YU39926B (en) 1985-06-30
CS153504B2 (ru) 1974-02-25
CH563984A5 (ru) 1975-07-15
AR193025A1 (es) 1973-03-30
NO132199B (ru) 1975-06-23
AR192699A1 (es) 1973-03-14
AR193024A1 (es) 1973-03-30
PH12640A (en) 1979-07-05
YU149975A (en) 1982-06-30
CH563988A5 (ru) 1975-07-15
CH566991A5 (ru) 1975-09-30
YU39653B (en) 1985-03-20
BG20340A3 (bg) 1975-11-05
AT291237B (de) 1971-07-12
PL74820B1 (ru) 1974-12-31
GB1268831A (en) 1972-03-29
YU39532B (en) 1984-12-31
JPS5330712B1 (ru) 1978-08-29
CS153508B2 (ru) 1974-02-25
SU428600A3 (ru) 1974-05-15
AT291234B (de) 1971-07-12
NL162647B (nl) 1980-01-15
CS153503B2 (ru) 1974-02-25
IL31861A (en) 1974-03-14
KE2542A (en) 1975-07-25
AR192864A1 (es) 1973-03-21
MY7500152A (en) 1975-12-31
RO66269A (fr) 1979-03-15
RO66273A (ro) 1981-08-17
CS153505B2 (ru) 1974-02-25
CS153506B2 (ru) 1974-02-25
AR194569A1 (es) 1973-07-31
OA03609A (fr) 1971-03-30
AR192560A1 (es) 1973-02-28
CS153511B2 (ru) 1974-02-25
IE33153L (en) 1969-09-27
IL31861A0 (en) 1969-05-28
SU419029A3 (ru) 1974-03-05
NL162647C (nl) 1980-06-16
CH554859A (de) 1974-10-15
CH563381A5 (ru) 1975-06-30
FI52579B (ru) 1977-06-30
CH563986A5 (ru) 1975-07-15
AT291242B (de) 1971-07-12
AT287685B (de) 1971-02-10
CH563989A5 (ru) 1975-07-15
CH563983A5 (ru) 1975-07-15
AT291235B (de) 1971-07-12
BG20339A3 (bg) 1975-11-05
BG20567A3 (bg) 1975-12-05
AT291240B (de) 1971-07-12
DK145226B (da) 1982-10-11
CY809A (en) 1976-12-01
RO61382A (ru) 1976-10-15

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