JPH04502334A - 3―アリールオキサゾリジノン誘導体、それらの製造方法及び治療での使用 - Google Patents
3―アリールオキサゾリジノン誘導体、それらの製造方法及び治療での使用Info
- Publication number
- JPH04502334A JPH04502334A JP2514788A JP51478890A JPH04502334A JP H04502334 A JPH04502334 A JP H04502334A JP 2514788 A JP2514788 A JP 2514788A JP 51478890 A JP51478890 A JP 51478890A JP H04502334 A JPH04502334 A JP H04502334A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- tables
- formulas
- alkyl
- 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
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/24—Oxygen atoms attached in position 2 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
Description
Claims (10)
- 1.式: ▲数式、化学式、表等があります▼(I)〔式中、 −R1はH又はC1−C4アルキルであり、−Xは酸素原子で、その場合R2= H又はハロゲンであるか、又はメチレン基或は−CH=CH−基で、その場合R 2=Hであり、 −nは、Xが酸素原子又はメチレン基である時1又は2であり、Xが−CH=C H−基である時0又は1であり、 −R3及びR4の各々は、独立にH、C1−C4アルキル、C4−C7シクロア ルキル、フェニル、又はベンジルであり、 −R5はH又はC1−C4アルキルであり、−R6はC1−C4アルキル、CH F2、CF3、CF3CF2、C4−C7シクロアルキル、フェニル、又はベン ジルであり、 −R4及びR6は更に一緒になって−(CH2)3−、又は−(CH2)4−鎖 を形成していてもよく、−R5及びR6は更に一緒になって−(CH2)4−、 又は−(CH2)5−鎖を形成していてもよく、そして−R7はH、C1−C4 アルキル、C2−C5アシル又はベンジルである〕。 の誘導体であって、ジアステレオマー又は鏡像体の形をしているか、シス又はト ランス型をしているか、又はラセミ形を含めたそれら全ての形の混合物の形をし ていいる誘導体。
- 2.請求項1に記載の誘導体において、−R1=H又はCH3、 −R2=H、 −X=酸素又はCH2、 −n=1又は2、 −R3、R4、及びR5はH又はCH3であり、−R6はCH3又はCF3であ り、そして−R7は、H、CH3又はアセチルである、誘導体。
- 3.請求項1に記載の誘導体において、−R1=CH3、 −R2=H、 −X=酸素、 −n=1又は2、 −R3=R4=R5=H、 −R6=CF3、及び −R7=H、 である誘導体。
- 4.請求項1に記載の誘導体において、−R1=CH3、 −R2=H、 −X=メチレン、 −n=1又は2、 −R3=R4=R5=H、 −R6=CF3、及び −R7=H、 である誘導体。
- 5.請求項1に記載の誘導体において、−R1=CH3、 −R2=H、 −XはCH=CHを表し、 −n=0又は1、 −R3=R4=R5=H、 −R6=CF3、及び −R7=H、 である誘導体。
- 6.請求項1に記載の誘導体において、−R1=CH6、 −R2=R3=R4=R5=R7=H、−n=1、 −R6=CF3、及び −X=酸素、 である誘導体。
- 7.二つの非対称炭素原子が(R)形態を有する請求項6に記載の誘導体。
- 8.請求項1〜7のいずれか1項に記載の少なくとも一種類の誘導体(I)と共 に、生理学的に許容出来る増量剤を含むことを特徴とする製薬組成物。
- 9.請求項1〜7のいずれか1項に記載の誘導体の、向精神薬製造のための使用 。
- 10.a)式: ▲数式、化学式、表等があります▼ 〔式中、R1は式(I)の場合と同じ意味を有する〕の化合物を、式: ▲数式、化学式、表等があります▼ 〔式中、 −Z1はOTs、OMs又はハロゲンであり、−R3=R4=H、 −n、R5、R6、及びR7は、式(I)の場合と同じ意味を有する〕 の化合物でO−アルキル化する; b)式: ▲数式、化学式、表等があります▼ 〔式中、 −Y=ハロゲン、 −R3〜R4及びnは、式(I)の場合と同じ意味を有する〕の化合物と、式: ▲数式、化学式、表等があります▼ 〔式中、R1=C1−C4アルキル〕 の化合物と縮合する: c)式: ▲数式、化学式、表等があります▼ 〔式中、n及びR3〜R4は、式(I)の場合と同じ意味を有する〕 の化合物の二重結合を水素化する; d)式: ▲数式、化学式、表等があります▼ 〔式中、X、n、R1、R3、R4、及びR6は、式(I)の場合と同じ意味を 有し、但しR6はCHF2、CF3、又はCF3CF2とは異なる〕 の化合物のC=O基をC−OHに還元する;e)C1−C4アルキルカーボネー トと、式:▲数式、化学式、表等があります▼ 〔式中、n、X、及びR3〜R7は、式(I)の場合と同じ意味を有し、但しR 7はC2−C5アシルとは異なる〕の化合物と縮合する; f)式: ▲数式、化学式、表等があります▼ 〔式中、n、X、及びR3〜R7は、式(I)の場合と同じ意味を有し、但しR 7はC2−C5アシルとは異なる〕の化合物をC1−C4アルキルハロゲン化物 でアルキル化する; g)式: ▲数式、化学式、表等があります▼ 〔式中、n、X、及びR3〜R7は、式(I)の場合と同じ意味を有する〕 の化合物と、式: ▲数式、化学式、表等があります▼ 〔式中、 −R1=C1−C4アルキル、 −Z=Ts又はMs〕 の化合物とを縮合する; h)式: ▲数式、化学式、表等があります▼アルキル〔式中、n、X、及びR3〜R7は 、式(I)の場合と同じ意味を有する〕 の化合物と、式: ▲数式、化学式、表等があります▼又は▲数式、化学式、表等があります▼〔式 中、R1=C1−C4アルキル〕 の化合物とを縮合する; i)式: ▲数式、化学式、表等があります▼ 〔式中、 −R1=C1−C4アルキル、 −n、X、及びR3〜R7は、式(I)の場合と同じ意味を有する〕 の化合物を水性酸で加水分解する; j)式: ▲数式、化学式、表等があります▼ 〔式中、種々の記号は式(I)の場合と同じ意味を有する〕の化合物をアシル化 する;又は k)式: ▲数式、化学式、表等があります▼ アシル 〔式中、種々の記号は式(I)の場合と同じ意味を有する〕の化合物を塩基性加 水分解により脱アシル化する;ことを含み、然も、前記反応a)〜k)の後で、 それら反応によって得られた化合物をハロゲンと反応させる工程を任意に行なっ てもよいことを特徴とする請求項1に記載の式(I)の誘導体の製造方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR8913555A FR2653017B1 (fr) | 1989-10-17 | 1989-10-17 | Derives d'aryl-3 oxazolidinone-2, leur procede de preparation et leur application en therapeutique. |
FR89/13555 | 1989-10-17 | ||
PCT/FR1990/000746 WO1991005775A1 (fr) | 1989-10-17 | 1990-10-17 | Aryl-3 oxazolidinones, preparation et utilisation |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH04502334A true JPH04502334A (ja) | 1992-04-23 |
JPH07103114B2 JPH07103114B2 (ja) | 1995-11-08 |
Family
ID=9386480
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2514787A Pending JPH04502333A (ja) | 1989-10-17 | 1990-10-17 | 3―アリールオキサゾリジノン誘導体、それらの製法、及び治療用としての使用 |
JP2514788A Expired - Lifetime JPH07103114B2 (ja) | 1989-10-17 | 1990-10-17 | 3―アリールオキサゾリジノン誘導体、それらの製造方法及び治療での使用 |
JP2514789A Pending JPH04502335A (ja) | 1989-10-17 | 1990-10-17 | 3―アリルオキサゾリジノン誘導体、その調製プロセスおよび治療への利用 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2514787A Pending JPH04502333A (ja) | 1989-10-17 | 1990-10-17 | 3―アリールオキサゾリジノン誘導体、それらの製法、及び治療用としての使用 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2514789A Pending JPH04502335A (ja) | 1989-10-17 | 1990-10-17 | 3―アリルオキサゾリジノン誘導体、その調製プロセスおよび治療への利用 |
Country Status (16)
Country | Link |
---|---|
US (3) | US5036090A (ja) |
EP (3) | EP0424243B1 (ja) |
JP (3) | JPH04502333A (ja) |
KR (3) | KR920701176A (ja) |
AT (2) | ATE126220T1 (ja) |
AU (3) | AU635779B2 (ja) |
CA (3) | CA2027783C (ja) |
DE (2) | DE69021498T2 (ja) |
DK (1) | DK0424244T3 (ja) |
ES (1) | ES2078958T3 (ja) |
FR (1) | FR2653017B1 (ja) |
GR (1) | GR3017708T3 (ja) |
HK (1) | HK1005591A1 (ja) |
NZ (3) | NZ235727A (ja) |
WO (3) | WO1991005775A1 (ja) |
ZA (3) | ZA908284B (ja) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5196543A (en) * | 1989-10-17 | 1993-03-23 | Delalande S.A. | 3-aryloxazolidinone derivatives, process for their preparation and their use in therapy |
FR2653017B1 (fr) * | 1989-10-17 | 1995-05-05 | Delalande Sa | Derives d'aryl-3 oxazolidinone-2, leur procede de preparation et leur application en therapeutique. |
US5235063A (en) * | 1989-10-17 | 1993-08-10 | Delalande S.A. | Process of preparing by condensation certain |
FR2675504B1 (fr) * | 1991-04-16 | 1995-01-27 | Delalande Sa | Derives d'aryl-3 oxazolidinone, leur procede de preparation et leur application en therapeutique. |
TW286317B (ja) * | 1993-12-13 | 1996-09-21 | Hoffmann La Roche | |
FR2715155B1 (fr) * | 1994-01-19 | 1996-07-26 | Mayoly Spindler | Inhibiteurs de la monoamine oxydase B et leurs procédés de préparation. |
FR2732679B1 (fr) * | 1995-04-07 | 1997-04-30 | Synthelabo | Procede de preparation enzymatique d'un intermediaire de synthese de la befloxatone |
AU699367B2 (en) * | 1995-06-02 | 1998-12-03 | Sanofi-Aventis | Isoindole derivatives, their preparation and their application in therapy |
FR2734821B1 (fr) * | 1995-06-02 | 1997-07-11 | Synthelabo | Derives de 5-methoxymethyl-3-(1,2-benzisoxazol-3-yl) oxazolidin-2-one, leur preparation et leur application en therapeutique |
FR2734820B1 (fr) * | 1995-06-02 | 1997-07-11 | Synthelabo | Derives de 3-(1,2-benzisoxazol-3-yl)oxazolidin-2-one, leur preparation et leur application en therapeutique |
FR2737206B1 (fr) * | 1995-07-24 | 1997-08-22 | Synthelabo | Derives d'oxazoloquinoleinone, leur preparation et leur application en therapeutique |
FR2741071B1 (fr) * | 1995-11-09 | 1997-12-12 | Synthelabo | Derives de 3-(benzofuran-5-yl)oxazolidin-2-one, leur preparation et leur application en therapeutique |
FR2741072B1 (fr) * | 1995-11-09 | 1997-12-12 | Synthelabo | Derives d'oxazolidin-2-one, leur preparation et leur application en therapeutique |
US6642409B2 (en) | 2000-01-27 | 2003-11-04 | Central Glass Company, Limited | Process for producing 4,4,4-trifluoro-3-hydroxybutyric acid derivatives |
US6444813B2 (en) * | 2000-02-02 | 2002-09-03 | Pharmacia & Upjohn Company | Linezolid-crystal form II |
WO2002018354A1 (en) * | 2000-08-31 | 2002-03-07 | Abbott Laboratories | Oxazolidinones and their use as antibacterial agents |
EP2266590A3 (en) | 2002-02-22 | 2011-04-20 | Shire LLC | Active agent delivery sytems and methods for protecting and administering active agents |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
LU80081A1 (fr) * | 1977-08-26 | 1979-05-15 | Delalande Sa | Nouvelles hydroxymethyl-5 oxazolidinones-2,leur procede de preparation et leur application therapeutique |
US4348393A (en) * | 1978-06-09 | 1982-09-07 | Delalande S.A. | N-Aryl oxazolidinones, oxazolidinethiones, pyrrolidinones, pyrrolidines and thiazolidinones |
FR2458547B2 (fr) * | 1978-06-09 | 1986-05-16 | Delalande Sa | Nouvelles n-aryle azolones, leur procede de preparation et leur application en therapeutique |
FR2506769A2 (fr) * | 1978-06-09 | 1982-12-03 | Delalande Sa | Para-((cyano-5 n pentyl-1) phenyl)-3 methoxymethyl-5 oxazolidinone-2, son procede de preparation et ses applications en therapeutique |
CA1171865A (en) * | 1980-06-04 | 1984-07-31 | Alain Lacour | N-aryl azolone derivatives, the process for preparing the same and their application in therapeutics |
FR2608604B1 (fr) * | 1986-12-19 | 1989-04-28 | Delalande Sa | Derives 5-hydroxyethyles de l'oxazolidinone-2, leurs procedes de preparation et leurs applications en therapeutique |
FR2653017B1 (fr) * | 1989-10-17 | 1995-05-05 | Delalande Sa | Derives d'aryl-3 oxazolidinone-2, leur procede de preparation et leur application en therapeutique. |
-
1989
- 1989-10-17 FR FR8913555A patent/FR2653017B1/fr not_active Expired - Fee Related
-
1990
- 1990-10-15 US US07/597,426 patent/US5036090A/en not_active Expired - Fee Related
- 1990-10-15 US US07/597,583 patent/US5036091A/en not_active Expired - Lifetime
- 1990-10-16 CA CA002027783A patent/CA2027783C/en not_active Expired - Lifetime
- 1990-10-16 CA CA002027782A patent/CA2027782C/en not_active Expired - Fee Related
- 1990-10-16 AT AT90402892T patent/ATE126220T1/de not_active IP Right Cessation
- 1990-10-16 DE DE69021498T patent/DE69021498T2/de not_active Expired - Lifetime
- 1990-10-16 DK DK90402892.5T patent/DK0424244T3/da active
- 1990-10-16 EP EP90402891A patent/EP0424243B1/fr not_active Expired - Lifetime
- 1990-10-16 DE DE69021823T patent/DE69021823T2/de not_active Expired - Fee Related
- 1990-10-16 EP EP90402893A patent/EP0428421A1/fr not_active Withdrawn
- 1990-10-16 AT AT90402891T patent/ATE126792T1/de active
- 1990-10-16 CA CA002027715A patent/CA2027715A1/en not_active Abandoned
- 1990-10-16 EP EP90402892A patent/EP0424244B1/fr not_active Expired - Lifetime
- 1990-10-16 US US07/598,254 patent/US5171747A/en not_active Expired - Fee Related
- 1990-10-16 ES ES90402892T patent/ES2078958T3/es not_active Expired - Lifetime
- 1990-10-17 JP JP2514787A patent/JPH04502333A/ja active Pending
- 1990-10-17 NZ NZ235727A patent/NZ235727A/en unknown
- 1990-10-17 ZA ZA908284A patent/ZA908284B/xx unknown
- 1990-10-17 KR KR1019910700618A patent/KR920701176A/ko active IP Right Grant
- 1990-10-17 NZ NZ235728A patent/NZ235728A/en unknown
- 1990-10-17 ZA ZA908285A patent/ZA908285B/xx unknown
- 1990-10-17 WO PCT/FR1990/000746 patent/WO1991005775A1/fr active Application Filing
- 1990-10-17 AU AU64715/90A patent/AU635779B2/en not_active Ceased
- 1990-10-17 JP JP2514788A patent/JPH07103114B2/ja not_active Expired - Lifetime
- 1990-10-17 WO PCT/FR1990/000745 patent/WO1991005774A1/fr unknown
- 1990-10-17 ZA ZA908283A patent/ZA908283B/xx unknown
- 1990-10-17 KR KR1019910700620A patent/KR920701178A/ko not_active Application Discontinuation
- 1990-10-17 AU AU64714/90A patent/AU637413B2/en not_active Expired
- 1990-10-17 KR KR1019910700619A patent/KR0149508B1/ko not_active IP Right Cessation
- 1990-10-17 AU AU64713/90A patent/AU637150B2/en not_active Ceased
- 1990-10-17 NZ NZ235729A patent/NZ235729A/en unknown
- 1990-10-17 JP JP2514789A patent/JPH04502335A/ja active Pending
- 1990-10-17 WO PCT/FR1990/000747 patent/WO1991005776A1/fr unknown
-
1995
- 1995-10-11 GR GR950402817T patent/GR3017708T3/el unknown
-
1998
- 1998-06-02 HK HK98104744A patent/HK1005591A1/xx not_active IP Right Cessation
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