CA2255333A1 - Quinolinone derivative, method for preparing the same, and anti-allergic agent - Google Patents

Quinolinone derivative, method for preparing the same, and anti-allergic agent

Info

Publication number
CA2255333A1
CA2255333A1 CA002255333A CA2255333A CA2255333A1 CA 2255333 A1 CA2255333 A1 CA 2255333A1 CA 002255333 A CA002255333 A CA 002255333A CA 2255333 A CA2255333 A CA 2255333A CA 2255333 A1 CA2255333 A1 CA 2255333A1
Authority
CA
Canada
Prior art keywords
group
general formula
hydrogen atom
alkyl group
alkenyl
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.)
Granted
Application number
CA002255333A
Other languages
French (fr)
Other versions
CA2255333C (en
Inventor
Hidetsugu Takagaki
Shinobu Yamaguchi
Masayoshi Abe
Mitsuru Sakai
Osamu Misumi
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.)
Activus Pharma Co Ltd
Original Assignee
Dainippon Ink and Chemicals 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 Dainippon Ink and Chemicals Co Ltd filed Critical Dainippon Ink and Chemicals Co Ltd
Publication of CA2255333A1 publication Critical patent/CA2255333A1/en
Application granted granted Critical
Publication of CA2255333C publication Critical patent/CA2255333C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

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
    • 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
    • A61P37/08—Antiallergic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/16—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • 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
    • C07D215/18—Halogen atoms or nitro radicals
    • 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
    • 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
    • C07D215/38—Nitrogen 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
    • C07D215/38—Nitrogen atoms
    • C07D215/40—Nitrogen atoms attached in position 8
    • 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
    • C07D215/48—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
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Abstract

The present invention relates to a simple method for preparing a quinolinone derivative, which is effective as a medicine, e.g., as an agent for treating allergic diseases and the like; novel amide derivatives effective as an intermediate in the method;
novel quinolinone derivatives obtained according to the method; and an anti-allergic agent containing a quinolinone derivative and/or physiological salt of the same as the active ingredients. The quinolinone derivative is expressed by the following general formula (II);
and the method is characterized in that an amide derivative, expressed by the following general formula (I), is reacted with a basic agent, followed by intramolecular ring formation:
General Formula (I) (wherein, R1 represents a hydrogen atom, an alkyl group, an alkyl group containing a hydroxyl group, an alkenyl group, or an aryl group; R2 represents an alkyl group, an alkenyl group, an aryl group, or an aralkyl group; R3 represents a reactive carboxyl group; and R4 to R7 represent, respectively and independently, a hydrogen atom, a hydroxyl group, an alkyl group, an alkoxy group, an alkenyl group, an alkenyloxy group, an aryl group, an aryloxy group, an aralkyloxy group, a R8R9N group (wherein, R8 and R9 represent, respectively and independently, a hydrogen atom, an alkyl group, an alkenyl group, an aralkyl group, or an acyl group), a nitro group, or a R10OOC group (wherein, R10 represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, or an aralkyl group)].
CA002255333A 1997-12-03 1998-12-01 Quinolinone derivative, method for preparing the same, and anti-allergic agent Expired - Fee Related CA2255333C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP33289497 1997-12-03
JP9-332894 1997-12-03

Publications (2)

Publication Number Publication Date
CA2255333A1 true CA2255333A1 (en) 1999-06-03
CA2255333C CA2255333C (en) 2004-07-13

Family

ID=18259997

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002255333A Expired - Fee Related CA2255333C (en) 1997-12-03 1998-12-01 Quinolinone derivative, method for preparing the same, and anti-allergic agent

Country Status (10)

Country Link
US (2) US6136822A (en)
EP (1) EP0927718B1 (en)
JP (1) JP3900720B2 (en)
KR (1) KR100511626B1 (en)
CN (1) CN1161337C (en)
AT (1) ATE260257T1 (en)
AU (1) AU737388B2 (en)
CA (1) CA2255333C (en)
DE (1) DE69821898T2 (en)
TW (1) TW430656B (en)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW430656B (en) * 1997-12-03 2001-04-21 Dainippon Ink & Chemicals Quinolinone derivative, method for preparing the same, and anti-allergic agent
KR100602617B1 (en) * 1999-09-10 2006-07-20 다이니혼 잉키 가가쿠 고교 가부시키가이샤 Quinolinone derivative preparations and process for producing the same
US6858540B2 (en) * 2000-05-11 2005-02-22 Applied Materials, Inc. Selective removal of tantalum-containing barrier layer during metal CMP
US6524167B1 (en) 2000-10-27 2003-02-25 Applied Materials, Inc. Method and composition for the selective removal of residual materials and barrier materials during substrate planarization
US6709316B1 (en) 2000-10-27 2004-03-23 Applied Materials, Inc. Method and apparatus for two-step barrier layer polishing
US7012025B2 (en) * 2001-01-05 2006-03-14 Applied Materials Inc. Tantalum removal during chemical mechanical polishing
US6706733B2 (en) * 2001-05-08 2004-03-16 Dainippon Ink And Chemicals, Inc. Quinolinone derivative formulation and its production method
KR100908418B1 (en) 2001-06-20 2009-07-21 액티버스 파마 컴퍼니 리미티드 Quinolinone derivative pharmaceutical composition and preparation method thereof
US7104869B2 (en) * 2001-07-13 2006-09-12 Applied Materials, Inc. Barrier removal at low polish pressure
US7008554B2 (en) * 2001-07-13 2006-03-07 Applied Materials, Inc. Dual reduced agents for barrier removal in chemical mechanical polishing
US6821881B2 (en) * 2001-07-25 2004-11-23 Applied Materials, Inc. Method for chemical mechanical polishing of semiconductor substrates
TWI295950B (en) * 2002-10-03 2008-04-21 Applied Materials Inc Method for reducing delamination during chemical mechanical polishing
CN100422155C (en) * 2003-07-30 2008-10-01 活效制药股份有限公司 Therapeutic agent for chronic obstructive pulmonary disease and method for treatment for chronic obstructive pulmonary disease with the same
USPP17182P3 (en) * 2003-10-02 2006-11-07 Plantas De Navarra S.A. Peach tree plant named ‘Plawhite 5’
TWI446425B (en) * 2007-08-29 2014-07-21 Applied Materials Inc High throughput low topography copper cmp process
SG193842A1 (en) 2008-08-06 2013-10-30 Biomarin Pharm Inc Dihydropyridophthalazinone inhibitors of poly(adp-ribose)polymerase (parp)
FR2951447B1 (en) * 2009-10-19 2012-10-19 Rhodia Operations ETHER AMIDE COMPOUNDS AND USES THEREOF
JP5883397B2 (en) 2010-02-03 2016-03-15 ビオマリン プハルマセウトイカル インコーポレイテッド Use of dihydropyridphthalazinone inhibitors of poly (ADP-ribose) polymerase (PARP) in the treatment of diseases associated with PTEN deficiency
KR101826652B1 (en) 2010-02-08 2018-02-07 메디베이션 테크놀로지즈, 인크. Processes of synthesizing dihydropyridophthalazinone derivatives
PT2630146T (en) 2010-10-21 2020-07-20 Medivation Tech Llc Crystaline (8s,9r)-5-fluoro-8-(4-fluorophenyl)-9-(1-methyl-1h-1,2,4-triazol-5-yl)-8,9-dihydro-2h-pyrido[4,3,2-de]phtalazin-3(7h)-one tosylate salt
FR2970964B1 (en) 2011-01-28 2013-12-13 Univ Claude Bernard Lyon NOVEL AZACOUMARIN DERIVATIVES WITH INHIBITOR ACTIVITY OF MDR PUMPS

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4124587A (en) * 1976-03-01 1978-11-07 Sandoz, Inc. 4-Hydroxy-3-sulfinyl-quinolin-2(1H)-ones
US4127574A (en) * 1976-03-01 1978-11-28 Sandoz, Inc. 4-Hydroxy-3-sulfonyl-quinolin-2(1H)-ones
US5190956A (en) * 1990-09-07 1993-03-02 Schering Corporation Certain N-substituted 3-oximino-2,4-dioxoquinolin-2,4-(1H)diones useful for treating viral infections
US5179107A (en) * 1990-09-07 1993-01-12 Schering Corporation Antiviral quinolinone compounds
JP3677878B2 (en) * 1995-07-31 2005-08-03 大日本インキ化学工業株式会社 Quinolinone derivatives and antiallergic agents containing the same as active ingredients
JP2943725B2 (en) * 1996-01-17 1999-08-30 大日本インキ化学工業株式会社 Quinolinone derivatives and antiallergic agents containing the same as active ingredients
TW430656B (en) * 1997-12-03 2001-04-21 Dainippon Ink & Chemicals Quinolinone derivative, method for preparing the same, and anti-allergic agent

Also Published As

Publication number Publication date
JP3900720B2 (en) 2007-04-04
CN1221738A (en) 1999-07-07
US6271416B1 (en) 2001-08-07
DE69821898T2 (en) 2004-08-19
CN1161337C (en) 2004-08-11
AU9515198A (en) 1999-06-24
KR100511626B1 (en) 2005-12-20
KR19990062717A (en) 1999-07-26
TW430656B (en) 2001-04-21
EP0927718B1 (en) 2004-02-25
CA2255333C (en) 2004-07-13
ATE260257T1 (en) 2004-03-15
DE69821898D1 (en) 2004-04-01
US6136822A (en) 2000-10-24
JPH11236374A (en) 1999-08-31
EP0927718A1 (en) 1999-07-07
AU737388B2 (en) 2001-08-16

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