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WO1993025531A1 - Cristal de type a de derive de naphthol - Google Patents

Cristal de type a de derive de naphthol Download PDF

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Publication number
WO1993025531A1
WO1993025531A1 PCT/JP1993/000733 JP9300733W WO9325531A1 WO 1993025531 A1 WO1993025531 A1 WO 1993025531A1 JP 9300733 W JP9300733 W JP 9300733W WO 9325531 A1 WO9325531 A1 WO 9325531A1
Authority
WO
WIPO (PCT)
Prior art keywords
crystal
type
crystals
naphthol
quinolylmethoxy
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/JP1993/000733
Other languages
English (en)
Japanese (ja)
Inventor
Kooji Kagara
Nobutaka Kawai
Koji Machitani
Kiyoaki Takasuga
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fujisawa Pharmaceutical Co Ltd
Original Assignee
Fujisawa Pharmaceutical Co Ltd
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 Fujisawa Pharmaceutical Co Ltd filed Critical Fujisawa Pharmaceutical Co Ltd
Publication of WO1993025531A1 publication Critical patent/WO1993025531A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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

Definitions

  • the present invention provides a naphthol derivative having a 5-lipoxygenase inhibitory activity and useful as an anti-inflammatory agent, for example, (+)-2,2-dibutyl-1-5- (2-quinolylmethoxy) -1,1,2,3 It relates to a new type A crystal of 4-tetrahydro-11-naphthol.
  • (+) — 2,2-Dibutyl-1- (2-quinolylmethoxy) -1,1,2,3,4-tetrahydro-1-naphthol is known as a substance having an inhibitory action on 5-lipoxygenase (for example, see JP-A-63-
  • this known crystal is relatively unstable, such as being slightly colored or slightly decomposed by light. For this reason, there has been a problem in producing a more stable crystal form free of such defects.
  • the type A crystal of the novel crystal of the present invention ie, (+)-2,2-dibutyl-5- (2-quinolylmethoxy) -1,2,3,4-tetrahydro-1-naphthol has the following physical properties. These physical properties are different from those of known crystals (the physical properties of other A-type crystals are the same as those of known crystals).
  • B-type crystals 1,2,3,4-tetrahydro-1-naphthol
  • the A-type crystal of the present invention can be produced, for example, by using the B-type crystal with n-hexane, n-heptane, isopropanol, hydrated isopropanol, or the like, for example, by the method described in Examples below.
  • FIG. 1 is an X-ray diffraction chart of the A-type crystal according to the present invention
  • FIG. 2 is an infrared absorption spectrum of the A-type crystal according to the present invention.
  • irradiation was performed at an illuminance of about 30000 lux for 5 days.
  • Freshly distilled tetrahydrofuran of lithium aluminum hydride (3.80 g) A freshly distilled tetrahydrofuran (60 ml) solution of (S)-(-) 4-anilinol 3-methylbutanol (1.96 g) in a suspension in orchid (120 ml) Is added dropwise over 1.5 hours in a nitrogen gas atmosphere while cooling in an ice bath. The suspension is stirred at room temperature for 1 hour and then cooled to 163 ° C.
  • the crude B-type crystal (100 g) obtained by the method of Production Example 1 was dissolved in n-heptane (800 ml) at 60 to 70 ° C, and charcoal powder (5 g) was added. Stir for a minute and filter out the charcoal dust. The charcoal powder etc. which has been filtered off is washed with n-heptane (700 ml). The filtrate and washing solution are combined, cooled to 40 ° C, and seed crystals (0.1 g) are added to precipitate crystals. After cooling to 30 ° C, raise the temperature again to 38-40 ° C to improve scaling and fluidity. Thereafter, the mixture is cooled to 10 ° C or less, and aged for 1 hour or more, and the precipitated crystals are collected by filtration.
  • the crude B-type crystal (100 g) obtained by the method of Production Example 1 is dissolved in isopropanol (400 ml) at 30 to 40 ° C, and then clarified and filtered through a filter. Wash the filter with isopropanol (200 ml). The filtrate and washing solution are combined, cooled to 5 ° C, seed crystals (0.1 g) are added to precipitate crystals, and the mixture is further stirred and aged at the same temperature for 3 hours.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Quinoline Compounds (AREA)

Abstract

Cristal de type A de (+)-2,2-dibutyl-5-(2-quinolylméthoxy)-1,2,3,4-tétrahydro-1-naphthol, ayant les propriétés énoncées ci-après et ne pouvant être ni décoloré ni décomposé, à la différence des cristaux classiques, lorsqu'il est soumis au rayonnement de la lumière: (1) point de fusion: environ 85 °C; (2) image diffractée de la poudre aux rayons X: comme indiqué à la figure; et (3) spectre d'absorption des infrarouges (nujol, cm-1): 3590, 1588, 1262, 1096, 819, 782.
PCT/JP1993/000733 1992-06-13 1993-05-31 Cristal de type a de derive de naphthol Ceased WO1993025531A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP17928192 1992-06-13
JP4/179281 1992-06-13

Publications (1)

Publication Number Publication Date
WO1993025531A1 true WO1993025531A1 (fr) 1993-12-23

Family

ID=16063099

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1993/000733 Ceased WO1993025531A1 (fr) 1992-06-13 1993-05-31 Cristal de type a de derive de naphthol

Country Status (1)

Country Link
WO (1) WO1993025531A1 (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63301840A (ja) * 1987-04-28 1988-12-08 Fujisawa Pharmaceut Co Ltd 新規二環式化合物、その製造法およびそれを含有する医薬組成物

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63301840A (ja) * 1987-04-28 1988-12-08 Fujisawa Pharmaceut Co Ltd 新規二環式化合物、その製造法およびそれを含有する医薬組成物

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