JP4633123B2 - イソニコチン酸誘導体の製造方法 - Google Patents
イソニコチン酸誘導体の製造方法 Download PDFInfo
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- JP4633123B2 JP4633123B2 JP2007539508A JP2007539508A JP4633123B2 JP 4633123 B2 JP4633123 B2 JP 4633123B2 JP 2007539508 A JP2007539508 A JP 2007539508A JP 2007539508 A JP2007539508 A JP 2007539508A JP 4633123 B2 JP4633123 B2 JP 4633123B2
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical class OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
- 235000019253 formic acid Nutrition 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- 238000005949 ozonolysis reaction Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- AHNJTQYTRPXLLG-UHFFFAOYSA-N lithium;diethylazanide Chemical group [Li+].CC[N-]CC AHNJTQYTRPXLLG-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 102100036837 Metabotropic glutamate receptor 2 Human genes 0.000 abstract description 2
- 239000005557 antagonist Substances 0.000 abstract description 2
- 230000019522 cellular metabolic process Effects 0.000 abstract description 2
- 210000003169 central nervous system Anatomy 0.000 abstract description 2
- 239000013067 intermediate product Substances 0.000 abstract description 2
- 108010038421 metabotropic glutamate receptor 2 Proteins 0.000 abstract description 2
- 229940123702 Adenosine A2a receptor antagonist Drugs 0.000 abstract 1
- 239000002467 adenosine A2a receptor antagonist Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000725 suspension Substances 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 4
- PMDHIMMPXRSDML-UHFFFAOYSA-N 2-methylpyridine-4-carboxylic acid Chemical compound CC1=CC(C(O)=O)=CC=N1 PMDHIMMPXRSDML-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- -1 trimethylsilyl ester Chemical class 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- ABQJPDCATHYDEM-UHFFFAOYSA-N n,n-dimethyl-2-(2-methylpyridin-4-yl)ethenamine Chemical compound CN(C)C=CC1=CC=NC(C)=C1 ABQJPDCATHYDEM-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 102000007471 Adenosine A2A receptor Human genes 0.000 description 1
- 108010085277 Adenosine A2A receptor Proteins 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- YOERHQDHKOWVGH-UHFFFAOYSA-N S(=O)(=O)(O)O.CC=1C=C(C(=O)O)C=CN1 Chemical compound S(=O)(=O)(O)O.CC=1C=C(C(=O)O)C=CN1 YOERHQDHKOWVGH-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000006138 lithiation reaction Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- HHUNWJWOJPWLNK-UHFFFAOYSA-N methyl 2-methylpyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC(C)=C1 HHUNWJWOJPWLNK-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
の化合物、およびその薬学的に許容される付加塩の製造方法に関する。
a)式II
b)式IIIの化合物をDMFと反応させ、式IV
c)式IVの化合物をO3およびH2O2で酸化し、式Ia
d)必要であれば、式Iaの化合物を式ROHのアルコールでエステル化し、式Ib
の化合物を生成する工程、
を含む。
工程a)は、式IIの2,4−ジメチル−ピリジンを、リチウム化剤、例えばリチウムジエチルアミドでリチウム化して、式IIIのリチウム化化合物にすることを含む。
工程b)は、式IIIの化合物をDMFと反応させ、式IVの化合物を生成することを含む。
工程c)は、式IVの化合物をO3およびH2O2で酸化し、式Iaの化合物を生成することを含む。
工程d)は、式Iaの化合物を式ROHのアルコールでエステル化し、式Ibの化合物を生成することを含む。
ジメチル−[2−(2−メチル−ピリジン−4−イル)−ビニル]−アミンの製造
i)2−メチル−イソニコチン酸の製造(酸添加無し、50℃)
2−メチル−イソニコチン酸メチルの製造
Claims (15)
- Rがメチルであることを特徴とする、請求項1の方法。
- リチウム化剤がリチウムジエチルアミドであることを特徴とする、請求項1の方法。
- 工程a)を有機溶媒中で−70℃〜0℃の温度で実施することを特徴とする、請求項1の方法。
- 有機溶媒がTHFであり、温度が−70℃〜−50℃であることを特徴とする、請求項4の方法。
- 工程b)が、式IIの化合物をDMFと−70℃〜0℃の温度で反応させることを含むことを特徴とする、請求項1の方法。
- 温度が−60℃〜−40℃であることを特徴とする、請求項6の方法。
- 工程c)において、オゾン分解を水1〜10%を含む有機溶媒中で0℃〜50℃の温度で実施することを特徴とする、請求項1の方法。
- 有機溶媒が酢酸であり、水含有量が5%であり、温度が15℃〜20℃であることを特徴とする、請求項8の方法。
- 工程c)において、H2O2を用いる酸化を追加の酸の非存在下で30℃〜100℃の温度で実施することを特徴とする、請求項1の方法。
- 温度が40℃〜60℃であることを特徴とする、請求項10の方法。
- 工程c)において、H2O2を用いる酸化を追加の酸の存在下で周囲温度で実施することを特徴とする、請求項1の方法。
- 追加の酸が、塩酸、硫酸またはギ酸であることを特徴とする、請求項12の方法。
- 工程d)を、アルコール中で鉱酸または鉱酸を発生する物質の存在下、60℃〜150℃の温度で実施することを特徴とする、請求項1の方法。
- アルコールがメタノールであり、鉱酸を発生させる物質がSOCl2であり、温度が60℃〜70℃であることを特徴とする、請求項14の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP04105554 | 2004-11-05 | ||
PCT/EP2005/011491 WO2006048172A1 (en) | 2004-11-05 | 2005-10-27 | Process for preparation of isonicotinic acid derivatives |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2008518991A JP2008518991A (ja) | 2008-06-05 |
JP4633123B2 true JP4633123B2 (ja) | 2011-02-16 |
Family
ID=35695862
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007539508A Expired - Fee Related JP4633123B2 (ja) | 2004-11-05 | 2005-10-27 | イソニコチン酸誘導体の製造方法 |
Country Status (10)
Country | Link |
---|---|
US (1) | US7459563B2 (ja) |
EP (1) | EP1812392B1 (ja) |
JP (1) | JP4633123B2 (ja) |
CN (1) | CN101056857B (ja) |
AT (1) | ATE400557T1 (ja) |
CA (1) | CA2586931C (ja) |
DE (1) | DE602005008095D1 (ja) |
ES (1) | ES2309814T3 (ja) |
TW (1) | TW200630340A (ja) |
WO (1) | WO2006048172A1 (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103044324B (zh) * | 2013-01-07 | 2014-05-21 | 湖南宏邦新材料有限公司 | 一种异烟酸酯及其制备方法 |
CN103848783B (zh) * | 2014-01-14 | 2016-05-04 | 红太阳集团有限公司 | 一种一步氧化合成2-氯烟酸的方法 |
CN110452165B (zh) * | 2018-05-07 | 2020-09-25 | 新发药业有限公司 | 一种2-甲基吡啶-4-甲酸的制备方法 |
CN113845502A (zh) * | 2021-11-29 | 2021-12-28 | 山东诚创蓝海医药科技有限公司 | 一种3-(苄氧基)-4-氧代-4h-吡喃-2-羧酸的制备方法 |
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DE2656468A1 (de) | 1976-12-14 | 1978-06-15 | Boehringer Mannheim Gmbh | N-(benzthiazol-2-yl)-oxamidsaeure- derivate und verfahren zu ihrer herstellung |
US4471957A (en) * | 1979-12-03 | 1984-09-18 | Baltimore Therapeutic Equipment Company | Method and apparatus for rehabilitation of damaged limbs |
DE3374550D1 (en) | 1982-12-21 | 1987-12-23 | Johnsen Jorgensen Plastics Ltd | Dispensing container |
KR930005004B1 (ko) | 1985-04-15 | 1993-06-11 | 쟈안센 파아마슈우티카 엔. 부이. | 치환된 n-[(4-피페리디닐)알킬]이환 축합 옥사졸아민 및 티아졸아민의 제조방법 |
FI91859C (fi) | 1987-06-17 | 1994-08-25 | Eisai Co Ltd | Analogiamenetelmä antiallergisena aineena aktiivisen bentsotiatsolijohdannaisen valmistamiseksi |
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-
2005
- 2005-10-27 US US11/259,880 patent/US7459563B2/en not_active Expired - Fee Related
- 2005-10-27 JP JP2007539508A patent/JP4633123B2/ja not_active Expired - Fee Related
- 2005-10-27 ES ES05808264T patent/ES2309814T3/es active Active
- 2005-10-27 WO PCT/EP2005/011491 patent/WO2006048172A1/en active IP Right Grant
- 2005-10-27 CN CN2005800380870A patent/CN101056857B/zh not_active Expired - Fee Related
- 2005-10-27 EP EP05808264A patent/EP1812392B1/en not_active Not-in-force
- 2005-10-27 AT AT05808264T patent/ATE400557T1/de not_active IP Right Cessation
- 2005-10-27 DE DE602005008095T patent/DE602005008095D1/de active Active
- 2005-10-27 CA CA2586931A patent/CA2586931C/en not_active Expired - Fee Related
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US20060100440A1 (en) | 2006-05-11 |
WO2006048172A1 (en) | 2006-05-11 |
CN101056857B (zh) | 2010-12-01 |
CA2586931C (en) | 2013-08-06 |
CN101056857A (zh) | 2007-10-17 |
JP2008518991A (ja) | 2008-06-05 |
TW200630340A (en) | 2006-09-01 |
ES2309814T3 (es) | 2008-12-16 |
ATE400557T1 (de) | 2008-07-15 |
EP1812392A1 (en) | 2007-08-01 |
US7459563B2 (en) | 2008-12-02 |
DE602005008095D1 (de) | 2008-08-21 |
EP1812392B1 (en) | 2008-07-09 |
CA2586931A1 (en) | 2006-05-11 |
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