WO1983002113A1 - Derives de propenylamine et medicaments les contenant - Google Patents

Derives de propenylamine et medicaments les contenant Download PDF

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Publication number
WO1983002113A1
WO1983002113A1 PCT/JP1981/000392 JP8100392W WO8302113A1 WO 1983002113 A1 WO1983002113 A1 WO 1983002113A1 JP 8100392 W JP8100392 W JP 8100392W WO 8302113 A1 WO8302113 A1 WO 8302113A1
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WO
WIPO (PCT)
Prior art keywords
methyl
alkyl
aryl
pharmaceutically acceptable
atom
Prior art date
Application number
PCT/JP1981/000392
Other languages
English (en)
Japanese (ja)
Inventor
Ltd. Yoshitomi Pharmaceutical Industries
Original Assignee
Yuki, Hiroshi
Hamasaki, Toshio
Kawasaki, Kazuyuki
Nakanishi, Akira
Haga, Keichiro
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Yuki, Hiroshi, Hamasaki, Toshio, Kawasaki, Kazuyuki, Nakanishi, Akira, Haga, Keichiro filed Critical Yuki, Hiroshi
Priority to PCT/JP1981/000392 priority Critical patent/WO1983002113A1/fr
Publication of WO1983002113A1 publication Critical patent/WO1983002113A1/fr

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Classifications

    • 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
    • C07D307/38—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
    • 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
    • C07D307/38—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
    • 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
    • C07D307/38—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
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • 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
    • 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
    • C07D307/58—One oxygen atom, e.g. butenolide

Definitions

  • the present invention relates to a general formula useful as a pharmaceutical or a synthetic intermediate thereof.
  • ⁇ 1 and R 2 are the same or different and represent a hydrogen-alkyl, an alkyl, a cycloazole, an aryl or an alkyl, R is hydrogen, nitrogen alkyl or alkoxy, and A and B are the same or different.
  • Equation ⁇ 2 a group represented by io (where X 2 represents an oxygen atom or a sulfur atom, Y represents aryl or lower alkyl or lower alkoxy having any position of 1 to 5 tones) Represents a pyridine which may be replaced by B, B 8 represents hydrogen or alkyl, and p represents 0 or an integer of 1 to 5).
  • an aryl and an arylalkyl may be a nitrogen, an alkyl, an alkoxy, a trifluoride at any position on the aromatic nucleus. It may be substituted by at least one substituent which is encountered with the methyl and methyl oxy groups.
  • alkyl refers to a linear or branched linear group having 1 to 8 strontium atoms, for example, methyl, ethyl, propyl, and a. So-propyl, butyl, isobutyl, tertiary butyl, pentyl, hexyl, and octyl.
  • Alkenyl is a carbon atom containing 2 carbon atoms. Linear or minute with ⁇ 8 values
  • Alkynyl has 2 to 8 carbon atoms, for example, ethynyl, pu / rugi. , 1-methyl-2-provinyl, alkoxy 'is a straight or branched chain having 1 to 8 carbon atoms, for example, methoxy. , Ethoxy, pro-box, iso-pro-box, buttocks, pent-ro-ki, hex-ro-xi, ok-ro-ki,
  • a cycloalkyl is one having 3 to 7 carbon atoms, such as cyclopropyl, cyclopenticole, and cyclohexyl.
  • An aryl is phenyl, naphthyl, etc.
  • an aryl is benzyl, phenyl, etc.
  • an alkylene is carbon number. 1 5 pieces, for example, methylene, ethylene, trimethylene, propylene, tetramethylene, 2 — methyltrimethylene And pentamethylene.
  • Halogen is chlorine, bromine, fluorine, etc.
  • the lower alkyl and lower alkoxy are the above-mentioned alkyl and alkoxy, respectively. Refers to those of ⁇ 4.
  • R 2 represents the condensation was not good even though aliphatic heterocyclic of instantaneous Sessu that nitrogen atom and 5 to 1 0-membered ring is a heterocyclic ring that be formed to also be Further, the ring may contain an oxygen atom, a sulfur atom, or a nitrogen atom, or may have one double bond. Examples of these include pyrrolidine, pyridyne, hexamethylenimine, morpholin, thiomolholin, and fourth place.
  • the present invention includes all tautomers and geometric isomers of the compound of the general formula (1).
  • the compound of the general formula (1) of the present invention is produced, for example, by the following method.
  • Q is as defined above, and L is halogen, methylyloxynoxy, trilithoxylinoxy, or acyloxy. The active residues are shown.
  • the compound of the formula (1) is reacted with an ammonium salt in a suitable solvent (water, alcohols, etc.) at room temperature or with heating, or is reacted with hexamethylene.
  • a suitable solvent water, alcohols, etc.
  • a method of reacting with tramine and then hydrolyzing with acid is reacted with tramine and then hydrolyzing with acid.
  • the compound of the general formula (II), which is a starting material, can be obtained by the following process.
  • R 4 is hydrogen and Q is a group represented by the formula (CH 2 pX 1 (0H 2 ) m — (where X 1 , m
  • n are as defined above. ) Is applied.
  • one of L 1 and L 2 is a hydroxyl group, a thiol
  • the other is a reactive residue (halogen, methyl sulfonyloxy-triethyl sulfonyloxy, acyloxy)
  • a metal salt such as a sodium salt or a potassium salt in the presence of a dehydrating agent such as hydrochloric acid or sulfuric acid, or
  • a starting material compound of the general formula ⁇ 3 ⁇ 4 for example, a compound of n ⁇ 1, L 1 -hydroxyl group or a reactive residue, is obtained by combining the compound of the general formula (II) with ⁇ —butyl lithium -React with phenol-formaldehyde or vinegar-formalin, etc.
  • R * has the formula -GNKR 5 (this 5 this; E, R 5 is the a Ru synonymous der.)
  • This reaction is carried out without a solvent, preferably in a solvent, at a temperature ranging from cooling to 200 ° C., under normal pressure or reduced pressure.
  • the solvent include water, alcohols (eg, methanol, ethanol, isopro- nol), ethers (eg, ethanol).
  • the reaction is
  • a heavy metal salt such as silver nitrate or mercuric chloride can be used as a catalyst.
  • E-In this method in the general formula (I), is a group represented by the formula — CNHB 5 (E and H U are as defined above), and Q is a group represented by the formula (GH 2 S (0H 2 ) m — (where n and m have the same meanings as above.): Applied when the group is represented by the general formula (I), is a group represented by the formula — CNHB 5 (E and H U are as defined above), and Q is a group represented by the formula (GH 2 S (0H 2 ) m — (where n and m have the same meanings as above.): Applied when the group is represented by the general formula (I), is a group represented by the formula — CNHB 5 (E and H U are as defined above), and Q is a group represented by the formula (GH 2 S (0H 2 ) m — (where n and m have the same meanings as above.): Applied when the group is represented by the general formula (I), is a group represented by the formula
  • L 3 is a hydroxyl group or its reactive group (halogen, methyl sulfonyloxy, trisulfonyloxy)
  • This reaction is carried out in the presence of a dehydrating agent such as hydrochloric acid, sulfuric acid, or the like, or with an alkali metal salt of thiol (cxy) (such as sodium salt or potassium salt). It is done.
  • a dehydrating agent such as hydrochloric acid, sulfuric acid, or the like
  • an alkali metal salt of thiol (cxy) such as sodium salt or potassium salt. It is done.
  • the reaction in Do solvent will I mentioned production method 8, is from under cooling carried out in 2 0 0 e C until the temperature at the.
  • W 3 represents a case in which W * is a decone group such as nitroamino, halogen, lower alkylthio, benzylthio, etc.
  • W * is amino
  • a group represented by the formula —X 1 (0H 2 ) m NH 2 (where each symbol is as defined above) is represented by the formula -X 1 (GH 2 ) m L * (where,
  • a reactive residue such as melogen, methyl sulfoxyloxy, trisulfuroxyloxyloxy, etc., and other symbols are as defined above.
  • halogen, methylsulfur W k represents the reactive residues such as rox, tri-res, ho-n-re, and a-
  • L 5 is halogen, methyl sul ijt dioxy, trilus krejoni oxy, aci oxy, etc. In the case of a group represented by), it represents a hydroxyl group or a thiol group, and other symbols are as defined above.
  • Solvents include, for example, water, alcohol granules (eg, methanol, ethanol, isobronol).
  • the reaction is carried out, preferably in a solvent such as alcohols, in gold.
  • L E is L 7 are two filtrated A Mi Bruno, c b gain down, lower A Le key Le Ji Oh, with base down di Le Chi O of any leaving group
  • a certain amino acid is used, and if it is an amino, it is possible to use a gene, a methyl resin, a polyethylene resin, a tris j, a resin, an acyl.
  • the O key sheet of any reactive residues, Q 1 represents an a Le key les down, and the other symbols Ru as defined above der.
  • the compound obtained by Production Methods 5 and 6 is used ubiquitously for the compound represented by the formula: Preferably, it is produced by reacting phosphorus pentasulfide with ⁇ benzene, toluene, dioxane, pyridin, dimethyl sulfoxide and the like under heating. Is performed.
  • the compound represented by the general formula ⁇ according to the present invention can be used as a free or acid addition salt or a hydrate as a medicament.
  • Acceptable acid addition salts include hydrochloric, sulfuric, hydrobromic, phosphoric, formic, acetic, oxalic, fumaric, maleic, quinone, tartaric, Inorganic salts such as linoleic acid, mandelic acid, methansulphonic acid, and toluenesulphonic acid, and salts of organic acids.
  • the compound (1) of the present invention a pharmaceutically acceptable acid addition salt thereof and a hydrate thereof can be used, for example, in mammals (eg, humans, rats, mice, mice, and mice).
  • mammals eg, humans, rats, mice, mice, and mice.
  • Has an inhibitory effect on gastric secretion, an antihypertensive effect, an anti-inflammatory effect, an analgesic effect, etc. for example, a gastrointestinal drug, a cardiovascular drug, an analgesic, an anti-inflammatory drug, or an intermediate between drugs.
  • a body for example, human static Mi emissions jB 2 - ⁇ inhibits this receptor
  • gastric acid secretion inhibitors As a result, gastric acid secretion inhibitors, anti-cancer drugs, and allergic disease drugs that use histamine as a medium reduce blood pressure or increase heart rate due to histamine.
  • Histamine 1 ⁇ Zk9 was administered from the crotch vein at 1 o'clock to induce gastric acid secretion.
  • the test compound was dissolved in physiological saline or diluted hydrochloric acid, and administered via the crotch vein 5 minutes before administration of histamine. I ⁇ of perfusate using an automatic titrator was measured by titration to pH 7.0 with 5 X 10 one 3N hydroxide Na Application Benefits ⁇ beam solution.
  • a dose of the test compound was administered to 4 rats to reduce the rate of inhibition of gastric acid secretion.
  • OMPI When the compound of the present invention is used as a medicament, it can be administered orally or parenterally, but in the case of oral, it is admixed with a pharmacologically acceptable carrier, excipient, and powder or tablet. It is used as a capsule, troche, troche, solution, capsule, and granule.
  • a pharmacologically acceptable carrier excipient, and powder or tablet.
  • it is used as a capsule, troche, troche, solution, capsule, and granule.
  • parenteral use used as an aqueous solution or non-aqueous suspension, as an injection such as intravenous, intramuscular, or subcutaneous injection, or as a shaving or cream ointment .
  • each unit preferably, each unit contains 1 to 20 active ingredients and is administered 2 to 4 times a day, and a daily dose of 50 to 1200 W is preferable. .
  • Formulation example Formulation example
  • Example 1 Example 1
  • the solution was added dropwise at 0 ° C and stirred for 1.5 hours, and then 2-methyl ⁇ -methyl-5- (3—dimethylamino-1-ob ovyl) Add 10.5 of thiophene hydrochloride at -5 to 0 and stir at room temperature for 8 hours.
  • the solvent is distilled off under reduced pressure, water is added, and the mixture is extracted with a black hole home, the ⁇ -hole home is washed with water, the solvent is distilled off under reduced pressure, and the residual oil is ethanol.
  • reaction mixture was poured into water, extracted with chloroform, the solvent was distilled off, and the residual oil was removed from column chromato gel (silica gel, chromatophore: methanol).
  • column chromato gel sica gel, chromatophore: methanol.
  • the oxalate in the ethanol has a melting point of 142 to 144 4, and has a melting point of 5— (11-phenyl-0.8—pyro).
  • ethanol 80 Z Z is refluxed at 4 o'clock and concentrated to dryness under reduced pressure. This is used as a calak mouth mat (silica gel, black mouth hole).
  • M methanol-10: 1), purified as oxalate in ethanol and recrystallized from ethanol-water, the melting point is 99-10. 2 * C ⁇ -methyl) ⁇ [2-[5-(& -Pyrrolidino 1-1 bronil) 1 2- ⁇ ⁇ ⁇ ⁇ ⁇ [Ethyl] 1-1-1-Port-1 1,1-Ethylenediamine / oxalate / 1Z2 hydrate is obtained.
  • N-methyl methacrylate 2 Ni-methyl methacrylate 2—Nitro 1, 1 ethene diamine oxalate, melting point 1668 or more
  • N-Methane sulfone N'-Methyl-N "[2-[5-(3-Pyrrolidine 1-Prinyl) 1 2-CH2 Lumethylthio) ethyl) guanidine
  • Methyl IT-1 2-[2-C5-(3-pyrrolidinone 1-bromide)-1 2-CHENYL] ⁇ CHILLIO , 1 2: Tokuguchi ⁇ 1 1.
  • a light yellow oil of 1,2-1,1-ethanediazine is obtained.
  • ⁇ This is considered to be a oxalate in ethanol, and its melting point is 144 to 144 °.
  • G (decomposed) oxalate is obtained.
  • N-Methyl-L N '-[4-1- [5-1- (p-methylphenyl) -13- (4-methyl-1-piperazinil)] ⁇ ⁇ 2 2 — 2 — 2 — — — 2 — 2 2 2 — —

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Dérivés de propénylamine représentés par la formule générale suivante:$(8,)$ ADoù R1 et R2 peuvent être identiques ou différents et représenter chacun l'hydrogène, un alkyl, un alkényl, un cycloalkyl, un aryl ou un aralkyl ou, pris ensemble, R1 et R2 représentent un cycle hétéro avec l'atome d'azote adjacent, R3 représente l'hydrogène, un halogène, un alkyl ou alkoxy, A et B peuvent être identiques ou différents et représenter chacun un atome d'hydrogène ou un aryl, Z représente l'oxygène ou un atome de soufre, q représente un alkylène ou un groupe représenté par -(CH2)n X1-(CH2)m-(où X1 représente un atome d'oxygène ou un atome de soufre, n représente un nombre entier entre 1 et 3, et m représente un nombre entier entre 2 et 4), R4 représente H,$(4,)$(où R5 représente H, un alkyl, un alkényl, un alkynyl, un alkoxy alkyl, un cycloalkyl, un aryl ou un aralkyl, et E représente l'oxygène ou un atome de soufre, =NR6(où R6 représente H, un cyano, un nitro, un alkyl, un aryl, un alkylsulfonyl ou un aryl sulfonyl) ou = CHR7(où R7 représente un nitro, un alkyl sulfonyl ou un aryl sulfonyl) ou un groupe représenté par la formule suivante:$(8,)$(où X2 représente un atome d'oxygène ou un atome de soufre, Y représente un aryl ou un pyridyl substitué facultativement par 1 à 5 substituants d'alkyl inférieurs ou d'alkoxy inférieurs dans des positions arbitraires, R8 représente H ou un alkyl, et p représente 0 ou un nombre entier de 1 à 5), l'aryl et l'aralkyl étant substitué facultativement en une position arbitraire du noyau aromatique par au moins un substituant sélectionné entre un halogène, un alkyl, un alkoxy, un trifluorométhyl, et un méthylène dioxy BD, ainsi que leurs sels d'addition acide pharmaceutiquement acceptables. Ces composés sont utiles en tant que médicaments pour l'appareil digestif, médicaments pour les organes circulatoires, analgésiques, agents anti-inflammatoires, ou des produits intermédiaires pour leur synthèse.
PCT/JP1981/000392 1981-12-17 1981-12-17 Derives de propenylamine et medicaments les contenant WO1983002113A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/JP1981/000392 WO1983002113A1 (fr) 1981-12-17 1981-12-17 Derives de propenylamine et medicaments les contenant

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Application Number Priority Date Filing Date Title
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1116486A4 (fr) * 1998-09-22 2007-06-20 Ishihara Sangyo Kaisha Composition medicale contenant des derives de nitroetheneamine ou des sels de ces derives comme constituants actifs

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5318557A (en) * 1976-08-04 1978-02-20 Allen & Hanburys Ltd Novel aminoalkylfuran derivatives* their preparation and medical composition containing same
JPS54109963A (en) * 1977-12-23 1979-08-29 Glaxo Group Ltd Amine derivatives* their manufacture and pharmaceutical composition containing them
JPS54115385A (en) * 1978-02-13 1979-09-07 Smith Kline French Lab Pyrimidone compound
JPS5547670A (en) * 1978-09-26 1980-04-04 Bristol Myers Co Substituted furans
JPS55113776A (en) * 1977-05-17 1980-09-02 Allen & Hanburys Ltd Novel amino compounds and their manufacture
JPS56169685A (en) * 1980-05-31 1981-12-26 Yoshitomi Pharmaceut Ind Ltd Novel heterocyclic derivative

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5318557A (en) * 1976-08-04 1978-02-20 Allen & Hanburys Ltd Novel aminoalkylfuran derivatives* their preparation and medical composition containing same
JPS55113776A (en) * 1977-05-17 1980-09-02 Allen & Hanburys Ltd Novel amino compounds and their manufacture
JPS54109963A (en) * 1977-12-23 1979-08-29 Glaxo Group Ltd Amine derivatives* their manufacture and pharmaceutical composition containing them
JPS54115385A (en) * 1978-02-13 1979-09-07 Smith Kline French Lab Pyrimidone compound
JPS5547670A (en) * 1978-09-26 1980-04-04 Bristol Myers Co Substituted furans
JPS56169685A (en) * 1980-05-31 1981-12-26 Yoshitomi Pharmaceut Ind Ltd Novel heterocyclic derivative

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1116486A4 (fr) * 1998-09-22 2007-06-20 Ishihara Sangyo Kaisha Composition medicale contenant des derives de nitroetheneamine ou des sels de ces derives comme constituants actifs

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