WO1982002045A1 - Pyridine derivatives - Google Patents

Pyridine derivatives Download PDF

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Publication number
WO1982002045A1
WO1982002045A1 PCT/JP1981/000374 JP8100374W WO8202045A1 WO 1982002045 A1 WO1982002045 A1 WO 1982002045A1 JP 8100374 W JP8100374 W JP 8100374W WO 8202045 A1 WO8202045 A1 WO 8202045A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
methyl
same
different
vis
Prior art date
Application number
PCT/JP1981/000374
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
Pharma Ind Ltd Yoshitomi
Original Assignee
Oe Takanori
Tsuruda Mineo
Goto Kazuhiro
Hisadome Masao
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 Oe Takanori, Tsuruda Mineo, Goto Kazuhiro, Hisadome Masao filed Critical Oe Takanori
Priority to DE8282900034T priority Critical patent/DE3174283D1/de
Publication of WO1982002045A1 publication Critical patent/WO1982002045A1/ja

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—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 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • 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]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • 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
    • C07D213/60—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 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
    • C07D213/61—Halogen atoms or nitro radicals
    • 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
    • C07D213/60—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 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • the present invention provides a complete pharmaceutical product
  • a novel pyri-5 derivative represented by and a salt thereof A novel pyri-5 derivative represented by and a salt thereof.
  • 1 , 2 , and ⁇ are the same or different.
  • it indicates a lower alkyl group such as 2nd or 37th tilde, or R 1 and R 2 , or 3 together with aspirin atoms that are inclusive of pyrrole ⁇ , Peripherals, 4-Medium) Levi Pera 5, 41- (t-Dr 1000 Shear) Pilane, Perhol, V5V, etc.
  • -L , 2 ⁇ may be the same or different and form a group forming an heterocyclic ring; methylene, ethyl, propyl, trimethyl; Aldyne groups of straight or branched ⁇ such as lamethyle, or 2-t dr.
  • the pyri derivative of Honki can be produced, for example, by the following method.
  • X 1 and X 2 are the same or different and represent Ge atoms such as fluorine-containing bromine.
  • the active hydrogen atom of the raw material ( ⁇ ) is hydrogenated into sodium, sodium lime, sodium lime, sodium lime, water lime, sodium lime.
  • the reaction is carried out by substituting an aluminum metal salt with a hydroxide hydroxide or the like.
  • reaction be carried out in the presence of a catalyst such as charcoal, sodium or charcoal.
  • Compound (I) is obtained by reacting a compound represented by the formula (compound (different from D)) under the above conditions. Needless to say, compound (oy) or (V) is once After that, it is possible to react with the same starting compound (! Without or simply by using it.
  • This method is applied when Z is -CZ ⁇ — or one CHiOH)-in the killing formula (I), and Z in the general formula (I). It reduces compounds that are CO-.
  • This reduction reaction can be carried out with methanol, ethanol, isopropanol, water, ether, tetradrofuran or- In a mixed solvent, complex metal hydrides such as borohydride sodium, aluminum hydride lithium, sodium ammonium gram, cremezene
  • complex metal hydrides such as borohydride sodium, aluminum hydride lithium, sodium ammonium gram, cremezene
  • the reduction is carried out according to ordinary methods such as reduction of oxygen, reduction of 1,000 sennas, reduction of corrosion, etc.
  • the thus obtained compound of the general formula (I) can be obtained by a conventional method using a compound having an amino acid (a quinine, a tartar, a fumaric acid, an oxalic acid, a succinic acid).
  • the compound of the killing formula (I) promotes leukocyte phagocytosis, promotes macrophage phagocytosis, promotes fertility in the form of zero-zette or promotes cell production, and inhibits apoptotic arthritis.
  • Test Example 2 Inhibitory effect of BALB / C mouse on immune response
  • mice each of which had a positive C-type mouse (6 weeks old) was used.
  • the lure is from the sheep red blood of X103 ⁇ 4
  • the antigen was administered by intraperitoneal administration.
  • the test compound was orally administered to each mouse on the day of sensitization and the next day.
  • the number of larvae formed in the liver, the number of vagina ( ⁇ C), and the number of rosette-forming cells (C) in the spleen and / or gonads were measured in a routine manner. It was measured by.
  • Test example 3 C5776 mouse promotes immune response ⁇
  • OVP1 ' ⁇ Sex C5 7 £ "6-mouse, 6 weeks old) was used as a detailed description of 6 animals.
  • the sensitization consisted of 5 X 10 sheep red M 3 ⁇ 4 ⁇ . This was achieved by intraperitoneal administration of the drug.
  • test compound was orally administered to each mouse on the day of sensitization and the next day.
  • the number of rosette forming cells (RFC) in spleen and Z or thymus was measured by a conventional method.
  • test compound results in an increase in stray or hepatic gland FC. This result indicates that the test compound has an immunostimulatory effect on C57 // 6 mouse ⁇
  • Peritoneal macrophage 5 was obtained from sex sesame (8-year-old) o 5 x 10 ⁇ ⁇ in macrophage in 1 / x solution; It was made to become ⁇ . A mixture containing the macrophage suspension 100 ⁇ , mouse serum 50 ⁇ and the test compound 100 n & was pre-incubated at 37 for 10 min.
  • test Example 5 Sudden detoxification control To determine acute toxicity using a mouse (8 rebate order) ⁇ ⁇ ⁇ ⁇ : No 5th-5th — 9 ' ⁇
  • the compound of the present invention When used as a medicament, it is mixed with an appropriate pharmacologically acceptable carrier, excipient, diluent, etc .; ) It can be administered orally or non- ⁇ in the form of injections, injections, etc.
  • the dosage varies depending on the target disease and symptoms, but is about 10 to 100 ⁇ per day for a regular adult.
  • Corresponding dibasic salt.1 ⁇ 2 Hydrate has a melting point of 1666-168 (ethanol 1 g ⁇ -l)

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Immunology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
PCT/JP1981/000374 1980-12-10 1981-12-09 Pyridine derivatives WO1982002045A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE8282900034T DE3174283D1 (en) 1980-12-10 1981-12-09 Pyridine derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP55175108A JPS5798262A (en) 1980-12-10 1980-12-10 Pyridine derivative
JP80/175108801210 1980-12-10

Publications (1)

Publication Number Publication Date
WO1982002045A1 true WO1982002045A1 (en) 1982-06-24

Family

ID=15990396

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1981/000374 WO1982002045A1 (en) 1980-12-10 1981-12-09 Pyridine derivatives

Country Status (4)

Country Link
US (1) US4465681A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
EP (1) EP0066628B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
JP (1) JPS5798262A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
WO (1) WO1982002045A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1215067A (en) * 1982-10-18 1986-12-09 Sudarshan K. Malhotra 2-(6-phenoxy-3-nitro-2-pyridinoxy)-propionate compounds
HU194830B (en) * 1984-10-05 1988-03-28 Richter Gedeon Vegyeszet Process for the production of derivatives of piridine
EP0338087A4 (en) * 1987-10-13 1991-07-24 Yoshitomi Pharmaceutical Industries, Ltd. Fused pyrazole compounds, process for their preparation, and their medicinal use
NZ227042A (en) * 1987-11-27 1991-05-28 Banyu Pharma Co Ltd Substituted alkylamine derivatives and pharmaceutical compositions
US5234946A (en) * 1987-11-27 1993-08-10 Banyu Pharmaceutical Co., Ltd. Substituted alkylamine derivatives
US5565413A (en) * 1994-12-06 1996-10-15 Zeneca Limited Substituted pyridyl phenyl ketone herbicides

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4060601A (en) * 1976-06-15 1977-11-29 Merck & Co., Inc. Certain lower-alkyl amino-2'-hydroxy-propoxy pyridines
JPS56100765A (en) * 1980-01-14 1981-08-12 Yoshitomi Pharmaceut Ind Ltd Pyridine derivative

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
No relevant documents have been disclosed *
See also references of EP0066628A4 *

Also Published As

Publication number Publication date
US4465681A (en) 1984-08-14
EP0066628B1 (en) 1986-04-02
EP0066628A1 (en) 1982-12-15
JPS6126992B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1986-06-23
JPS5798262A (en) 1982-06-18
EP0066628A4 (en) 1983-05-16

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