IL40855A - Bis-(4-substituted-phenoxy)acetic(or malonic)acid derivatives and processes for their preparation - Google Patents

Bis-(4-substituted-phenoxy)acetic(or malonic)acid derivatives and processes for their preparation

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Publication number
IL40855A
IL40855A IL40855A IL4085572A IL40855A IL 40855 A IL40855 A IL 40855A IL 40855 A IL40855 A IL 40855A IL 4085572 A IL4085572 A IL 4085572A IL 40855 A IL40855 A IL 40855A
Authority
IL
Israel
Prior art keywords
hydroxy
give
formula
compound
piperidino
Prior art date
Application number
IL40855A
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IL40855A0 (en
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Merck Patent Gmbh
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Publication date
Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh
Publication of IL40855A0 publication Critical patent/IL40855A0/en
Publication of IL40855A publication Critical patent/IL40855A/en

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    • 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
    • C07D207/32—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/325—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • 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
    • C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—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 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
    • C07D207/12—Oxygen or sulfur atoms
    • 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
    • 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
    • C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • 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
    • 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
    • C07D215/04—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C07D215/06—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
    • 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
    • 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
    • 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
    • C07D215/16—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 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
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
    • 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
    • C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Indole Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1358609 Substituted bisphenoxy or phenylthio- α-carboxylic acids MERCK PATENT GmbH 16 Nov 1972 [18 Dec 1971] 53005/72 Heading C2C Novel compounds of Formula I in which Z<SP>1</SP> and Z<SP>2</SP> are each O or S, R<SP>1</SP> is H or alkyl with 1-10 C atoms, R<SP>2</SP> is H or COOR<SP>7</SP>, R<SP>3</SP> and R<SP>4</SP> are R<SP>8</SP>, R<SP>8</SP>-CH 2 -, p-R<SP>8</SP>-C 6 H 4 -, 3-hydroxypyrrolidino, 3-hydroxy-piperidino, morpholino, isoindolino, 1,2,3,4-tetra-hydroquinolino, 1-R<SP>9</SP>-1,2,3,4-tetrahydro-4-quinolyl, 1-R<SP>10</SP>-4-piperidyl or 1-pyrryl, R<SP>5</SP> and R<SP>6</SP> are each H, alkyl with 1-4 C atoms or Hal, R<SP>7</SP>, R<SP>9</SP> and R<SP>10</SP> are each H or alkyl with 1-10 C atoms, R<SP>8</SP> is pyrrolidino, piperidino or homopiperidino, and Hal is F, Cl, Br or I, and their physiologically acceptable salts with acids and bases (e.g. cylohexylamine) are prepared by one of the following methods: (a) a compound of Formula II or a metal salt thereof is reacted with a compound of Formula III wherein X is OH, esterified OH, or Cl, Br or I; (b) cyclizing a compound of Formula IV wherein Y is tetramethylene, pentamethylene, hexamethylene, 2-hydroxy-tetramethylene, 2- hydroxy-pentamethylene, 3-oxapentamethylene or o-xylylene, X<SP>1</SP> is Cl, Br, I, NH 2 or a hydroxy group which may optionally be esterified or etherified and X<SP>2</SP> is a bond, methylene or pphenylene; (c) treating a compound of Formula V wherein W is an optionally functionally modified carboxylic group with solvolysing, thermolysing, or ester forming agent to convert W into -COOR<SP>1</SP>; (d) reacting a compound of Formula VI wherein X<SP>3</SP> is H, Cl, Br, I, NH 2 or SO 3 M where M is one equivalent of a metal atom, with the compound R<SP>3</SP>-X<SP>4</SP> in which X<SP>4</SP> is H, M or X provided that X<SP>3</SP> and X<SP>4</SP> are different and one of them is H or, for X<SP>4</SP> M. In all cases a salt may be then formed and if required any radical R<SP>2</SP> may be converted to another value of R<SP>2</SP> and racemates may be resolved. 4-Piperidino-thiophenol is prepared by the reduction of 4-piperidinobenzene sulphochloride with Sn/HCl. Various phenols of Formula II above, Z 1 = OH, are prepared in the examples by splitting off the methyl group from the corresponding anisoles prepared in situ (a) by reaction of the corresponding amine with α-#-dihaloalkane or an α-#-dialkylether, both optionally hydroxy substituted or an o-xylylene dibromide or a 2,5- dialkoxytetrahydrofuran, or (b) by reaction of a methoxy-benzyl chloride with pyrrolidine, piperidine or homopiperidine, or (c) dehydrohalogenation of a haloanisole. Other methods for preparation of the phenols of Formula II are as follows: (a) 3-chloro-4-(3-hydroxy-piperidino)- phenol (obtainable by reaction of 3-nitro-4- bromo-anisole with 3-hydroxy-piperidine to give 3-nitro-4-(3-hydroxy-piperidino)-anisole, hydrogenation on 5% Pd/C to give 3-amino-4-(3- hydroxy-piperidino)-anisole, diazotization and Sandmeyer reaction to give 3-chloro-4-(3- hydroxy-piperidino)-anisole; or (b) 4-(1,2,3,4- tetrahydro-quinolino)-phenol obtainable by reaction of N-p-methoxyphenylanthranilic acid with acetic anhydride and subsequent saponification to give 1-p-methoxyphenyl-4-hydroxy-2- quinolone, reaction with POCl 3 to give 1-pmethoxyphenyl-4-chloro-2-quinolone, hydrogenation to give 1-p-methoxyphenyl-3,4-dihydro- 2-quinolone, reduction with LiAlH 4 to give 1-pmethoxy - phenyl - 1,2,3,4 - tetrahydroquinoline; (c) 4-(1,2,3,4-tetrahydro-4-quinolyl)-phenol and hydrochloride obtainable by cyclization of pmethoxy-cinnamic acid anilide with polyphosphoric acid to give 4-(p-methoxyphenyl)-1,2,3,4- tetrahydro-2-quinolone, reduction with LiAlH 4 to give 4-(p-methoxyphenyl)-1,2,3,4-tetrahydroquinoline and splitting of the ether with HBr; (d) 4-(1-methyl-1,2,3,4-tetrahydro-4-quinolyl)- phenol obtainable by methylation of 4-(pmethoxyphenyl) - 1,2,3,4 - tetrahydro - quinoline with formaldehyde/H 2 , 5% Pd/C, to give 1- methyl-4-p-methoxyphenyl-1,2,3,4-tetrahydroquinoline and splitting of the ether with HBr; and (e) 4-(1-methyl-4-piperidyl)-phenol (obtainable by treatment of 1-methyl-4-piperidinol with phenol/AlCl 3 in benzene or of 1-methyl-4- piperidone with p-anisylmagnesium bromide with subsequent dehydration, hydrogenation and splitting the ether with HBr. Pharmaceutical compositions in conventional forms for oral, rectal, topical or parenteral administration having activity in lowering of cholesterol and triglyceride levels comprise an above novel compound or salt and a carrier or excipient. [GB1358609A]

Claims (1)

1. WHAT CLAIM acid dori of a which is w C is pi or is t oir sal to with acid o acid Qthy acid dimethyl yl cid acid yl proeooo a of I a aecoptablo salt which a of which R tho claim a reaotivo of a compound with a v in og A in claim A of a compound of formula I log c acceptable salt a of IV isa Y io or io or an OH which may optionally bo or otho and is a bond or and to tho in claim A process for preparation of a of I or acceptable t thereo which comprisoo a of which is a or a modified and to have the claim a or in to radical into radical Λ proccoo to any 1 0 in in tho compound obtained io into a different radical tho of fo by with an acid or baoo a acceptable acid addition salt or or oalt of a fo I io for I io by t a baoo or Λ proccoo for the preparation of a to claim heroin in of tho A at least ao of 1 to 9 and e t acceptable claiia 16 in each 10 of said a insufficientOCRQuality
IL40855A 1971-12-18 1972-11-15 Bis-(4-substituted-phenoxy)acetic(or malonic)acid derivatives and processes for their preparation IL40855A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2163056A DE2163056A1 (en) 1971-12-18 1971-12-18 CARBONIC ACID DERIVATIVES AND THE PROCESS FOR THEIR PRODUCTION

Publications (2)

Publication Number Publication Date
IL40855A0 IL40855A0 (en) 1973-01-30
IL40855A true IL40855A (en) 1976-02-29

Family

ID=5828500

Family Applications (1)

Application Number Title Priority Date Filing Date
IL40855A IL40855A (en) 1971-12-18 1972-11-15 Bis-(4-substituted-phenoxy)acetic(or malonic)acid derivatives and processes for their preparation

Country Status (18)

Country Link
JP (1) JPS4867269A (en)
AT (1) AT329055B (en)
AU (1) AU464750B2 (en)
BE (1) BE792853A (en)
BR (1) BR7208702D0 (en)
CA (1) CA980346A (en)
CS (1) CS167366B2 (en)
DD (1) DD105443A5 (en)
DE (1) DE2163056A1 (en)
ES (1) ES409727A1 (en)
FR (1) FR2163487B1 (en)
GB (1) GB1358609A (en)
HU (1) HU165098B (en)
IL (1) IL40855A (en)
NL (1) NL7217100A (en)
PL (1) PL79179B1 (en)
RO (1) RO62851A (en)
ZA (1) ZA728065B (en)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3448105A (en) * 1966-06-07 1969-06-03 Sandoz Ag Basic esters of malonic acid
CH514581A (en) * 1967-02-21 1971-10-31 Sandoz Ag Process for the production of new acetic acid derivatives
CH526538A (en) * 1967-07-22 1972-08-15 Merck Patent Gmbh Process for the preparation of aminophenylacetic acid derivatives
DE2112272A1 (en) * 1971-03-15 1972-10-05 Merck Patent Gmbh Phenoxyacetic acid derivatives and process for their preparation

Also Published As

Publication number Publication date
ZA728065B (en) 1973-07-25
FR2163487A1 (en) 1973-07-27
CS167366B2 (en) 1976-04-29
IL40855A0 (en) 1973-01-30
ES409727A1 (en) 1976-03-16
HU165098B (en) 1974-06-28
CA980346A (en) 1975-12-23
DD105443A5 (en) 1974-04-20
AT329055B (en) 1976-04-26
FR2163487B1 (en) 1975-10-17
AU464750B2 (en) 1975-08-20
NL7217100A (en) 1973-06-20
PL79179B1 (en) 1975-06-30
GB1358609A (en) 1974-07-03
BR7208702D0 (en) 1973-09-20
BE792853A (en) 1973-06-15
JPS4867269A (en) 1973-09-13
ATA1065772A (en) 1975-07-15
RO62851A (en) 1978-01-15
DE2163056A1 (en) 1973-06-20
AU5022772A (en) 1974-06-20

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