JP5059599B2 - 化学的工程 - Google Patents
化学的工程 Download PDFInfo
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- JP5059599B2 JP5059599B2 JP2007505626A JP2007505626A JP5059599B2 JP 5059599 B2 JP5059599 B2 JP 5059599B2 JP 2007505626 A JP2007505626 A JP 2007505626A JP 2007505626 A JP2007505626 A JP 2007505626A JP 5059599 B2 JP5059599 B2 JP 5059599B2
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- hydrogenation
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- 238000001311 chemical methods and process Methods 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 14
- 229910052723 transition metal Inorganic materials 0.000 claims description 9
- 150000003624 transition metals Chemical class 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052697 platinum Inorganic materials 0.000 claims description 6
- 229910052720 vanadium Inorganic materials 0.000 claims description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
- CJJLJBFJNXMANZ-UHFFFAOYSA-N 4,6-dichloro-2-propylsulfanylpyrimidin-5-amine Chemical compound CCCSC1=NC(Cl)=C(N)C(Cl)=N1 CJJLJBFJNXMANZ-UHFFFAOYSA-N 0.000 claims description 3
- DDEDQHVHVPJFAC-UHFFFAOYSA-N 4,6-dichloro-5-nitro-2-propylsulfanylpyrimidine Chemical compound CCCSC1=NC(Cl)=C([N+]([O-])=O)C(Cl)=N1 DDEDQHVHVPJFAC-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 25
- 125000000217 alkyl group Chemical group 0.000 abstract description 14
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 13
- 239000002904 solvent Substances 0.000 abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 5
- 125000001309 chloro group Chemical group Cl* 0.000 abstract description 5
- 125000005843 halogen group Chemical group 0.000 abstract description 5
- 238000005580 one pot reaction Methods 0.000 abstract description 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052736 halogen Inorganic materials 0.000 abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 abstract description 4
- 239000001301 oxygen Substances 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- 239000005864 Sulphur Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 13
- -1 3,4-difluorophenyl Chemical group 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- 0 *c1nc(*)nc(*)c1[N+]([O-])=O Chemical compound *c1nc(*)nc(*)c1[N+]([O-])=O 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 229960004592 isopropanol Drugs 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- ORMOPLFFXOSAPS-UHFFFAOYSA-N (4,6-dichloro-2-propylsulfanylpyrimidin-5-yl)-(4-methylphenyl)diazene Chemical compound ClC1=NC(SCCC)=NC(Cl)=C1N=NC1=CC=C(C)C=C1 ORMOPLFFXOSAPS-UHFFFAOYSA-N 0.000 description 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- GJSKUPWUDKTHHN-UHFFFAOYSA-N 4,6-dichloro-2-propylsulfanylpyrimidine Chemical compound CCCSC1=NC(Cl)=CC(Cl)=N1 GJSKUPWUDKTHHN-UHFFFAOYSA-N 0.000 description 1
- ORMOPLFFXOSAPS-FMQUCBEESA-N ClC1=NC(SCCC)=NC(Cl)=C1\N=N\C1=CC=C(C)C=C1 Chemical compound ClC1=NC(SCCC)=NC(Cl)=C1\N=N\C1=CC=C(C)C=C1 ORMOPLFFXOSAPS-FMQUCBEESA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000010118 platelet activation Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- FVLAYJRLBLHIPV-UHFFFAOYSA-N pyrimidin-5-amine Chemical compound NC1=CN=CN=C1 FVLAYJRLBLHIPV-UHFFFAOYSA-N 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000011949 solid catalyst Substances 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
化合物[1S−(1α,2α,3β(1S*,2R*),5β)]−3−[7−[2−(3,4−ジフルオロフェニル)−シクロプロピル]アミノ]−5−(プロピルチオ)−3H−1,2,3−トリアゾロ[4,5−d]ピリミジン−3−イル)−5−(2−ヒドロキシエトキシ)−シクロペンタン−1,2−ジオール(化合物A)、およびその類似化合物は、医薬的に活性なP2T(現在は通常P2Y12として言及される)受容体アンタゴニストとして、WO00/34283およびWO99/05143に開示されている。当該アンタゴニストは、とりわけ、血小板活性化、凝集、または脱顆粒の阻害剤として使用されうる。
芳香族ニトロ化合物の触媒的水素化がUS6096924に開示されている。
の化合物の調製方法であって、
a.式(II);
b.式(III):
の化合物のワンポットの水素化であって、
i.最初に約20℃で式(IV):
ii.その後約40℃とし;
工程(i)および(ii)の両方を好適な触媒の存在下、および好適な溶媒の存在下で行う水素化を行うこと
のいずれかを含む前記方法を提供する。
1つの特定の側面において、本発明は、式(I):
の化合物の調製方法であって、式(II):
式(II)の化合物の水素化のための好適な遷移金属触媒は、例えば、白金またはパラジウム、または白金と、バナジウム、鉄またはマンガンなどの別の遷移金属の組み合わせである。本発明の更なる側面において、遷移金属触媒は、例えば炭素などの好適な担体上にある。
さらに別の側面において、式(II)の化合物の水素化は、1〜10bar、例えば2〜4barの圧力で行われる。
の化合物の調製方法であって、
式(III):
の化合物のワンポットの水素化であって、
i.最初に10〜25℃で式(IV):
ii.その後約35〜50℃で水素化し;
工程(i)および(ii)の両方を好適な触媒の存在下、および好適な溶媒の存在下で行う水素化を行うことを含む前記方法を提供する。
別の側面において、本発明は、Xがクロロである、既に定義した方法を提供する。
さらに別の側面において、本発明は、R1がC1−4アルキル(n−プロピルなど)またはC1−4ハロアルキル(3,3,3−トリフルオロプロプ−1−イルなど)である、既に定義した方法を提供する。
以下の実施例により本発明を説明する。
この実施例は、4,6−ジクロロ−2−(プロピルチオ)ピリミジン−5−アミンの製造方法を説明する。
この実施例は、4,6−ジクロロ−5−[(E)−(4−メチルフェニル)ジアゼニル]−2−(プロピルスルファニル)ピリミジンからの、4,6−ジクロロ−2−(プロピルチオ)ピリミジン−5−アミンの調製方法を説明する。
Claims (1)
- 4,6−ジクロロ−2−(プロピルチオ)ピリミジン−5−アミンの調製方法であって、
4,6−ジクロロ−5−ニトロ−2−(プロピルチオ)ピリミジンを、遷移金属触媒の存在下、t−ブチルメチルエーテル中で3barおよび30℃で3時間水素化することを含み、
ここで遷移金属触媒が活性炭に吸着させた3%Ptおよび0.6%Vであって、該触媒が4,6−ジクロロ−5−ニトロ−2−(プロピルチオ)ピリミジンに対して10%w/wに対応する量で存在する、前記方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE0401001A SE0401001D0 (sv) | 2004-03-31 | 2004-03-31 | Chemical process |
SE0401001-3 | 2004-03-31 | ||
PCT/GB2005/001188 WO2005095358A2 (en) | 2004-03-31 | 2005-03-29 | Process for the preparation of aminopyrimidines |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007530650A JP2007530650A (ja) | 2007-11-01 |
JP5059599B2 true JP5059599B2 (ja) | 2012-10-24 |
Family
ID=32294337
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007505626A Expired - Fee Related JP5059599B2 (ja) | 2004-03-31 | 2005-03-29 | 化学的工程 |
Country Status (24)
Country | Link |
---|---|
US (2) | US7799914B2 (ja) |
EP (2) | EP1751117B1 (ja) |
JP (1) | JP5059599B2 (ja) |
KR (1) | KR101164265B1 (ja) |
CN (2) | CN101851212A (ja) |
AT (1) | ATE517096T1 (ja) |
AU (1) | AU2005227727B2 (ja) |
BR (1) | BRPI0509323A (ja) |
CA (1) | CA2560094C (ja) |
CY (1) | CY1111847T1 (ja) |
DK (1) | DK1751117T3 (ja) |
ES (1) | ES2368069T3 (ja) |
HK (1) | HK1103727A1 (ja) |
HR (1) | HRP20110658T1 (ja) |
IL (1) | IL177998A (ja) |
NO (1) | NO20064117L (ja) |
NZ (2) | NZ550128A (ja) |
PL (1) | PL1751117T3 (ja) |
PT (1) | PT1751117E (ja) |
SE (1) | SE0401001D0 (ja) |
SG (1) | SG151311A1 (ja) |
SI (1) | SI1751117T1 (ja) |
WO (1) | WO2005095358A2 (ja) |
ZA (1) | ZA200607708B (ja) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE0401001D0 (sv) * | 2004-03-31 | 2004-03-31 | Astrazeneca Ab | Chemical process |
JP5275046B2 (ja) * | 2006-02-13 | 2013-08-28 | ロンザ アーゲー | 5−(アリール−ジアゼニル)−4,6−ジハロ−ピリミジンの還元 |
SG196805A1 (en) | 2008-09-09 | 2014-02-13 | Astrazeneca Ab | A process for preparing [1s- [1-alpha, 2-alpha, 3-beta (1s*, 2r*) 5-beta] ] -3- [7- [2- (3, 4-dif luorophenyl) -cyclopropylamino] - 5- (propylthio) -3h-1, 2, 3-triazolo [4, 5-d] pyrimidin-3-yl] -5- (2- hydroxyethoxy) cyclopentane-1, 2-diol and to its intermediates |
EP2305376A1 (en) * | 2009-09-23 | 2011-04-06 | Lonza Ltd. | Process and catalyst for the catalytic hydrogenation of aromatic and heteroaromatic nitro compounds |
US9233966B2 (en) | 2012-04-05 | 2016-01-12 | Dr. Reddy's Laboratories Limited | Preparation of ticagrelor |
CN103130726A (zh) * | 2013-02-07 | 2013-06-05 | 许学农 | 替卡格雷中间体4,6-二氯-2-(丙巯基)-5-氨基嘧啶的制备方法 |
WO2014206187A1 (zh) | 2013-06-24 | 2014-12-31 | 苏州明锐医药科技有限公司 | 替卡格雷及其中间体的制备方法 |
JP6463758B2 (ja) * | 2013-08-22 | 2019-02-06 | ジェネンテック, インコーポレイテッド | 化合物の調製方法 |
CN103588712B (zh) * | 2013-11-08 | 2016-06-08 | 南京欧信医药技术有限公司 | 一种嘧啶类化合物及其制备方法、和应用 |
CN103923020A (zh) * | 2014-04-02 | 2014-07-16 | 黄河三角洲京博化工研究院有限公司 | 一种2-丙硫基-4,6-二氯-5-氨基嘧啶的制备方法 |
CN105020602B (zh) * | 2014-04-30 | 2017-12-08 | 欧普照明股份有限公司 | 一种led灯 |
CN103992277A (zh) * | 2014-05-16 | 2014-08-20 | 苏州天马精细化学品股份有限公司 | 一种替卡格雷中间体4,6-二氯-5-氨基-2-丙硫基嘧啶的制备方法 |
CN105294573B (zh) * | 2015-06-16 | 2018-07-10 | 厦门医学院 | 一种合成4,6-二氯-2-(丙硫基)-5-氨基嘧啶的方法 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3141028B2 (ja) * | 1991-04-06 | 2001-03-05 | アストラ・フアーマシユウテイカルズ・リミテツド | Atp類似体 |
CZ289721B6 (cs) * | 1995-05-19 | 2002-03-13 | Syngenta Participations Ag | Způsob katalytické hydrogenace aromatických nitrosloučenin |
AR017014A1 (es) | 1997-07-22 | 2001-08-22 | Astrazeneca Ab | Compuestos de triazolo [4,5-d]pirimidina, composiciones farmaceuticas, uso de los mismos para preparar medicamentos y procesos para la preparacionde dichos compuestos |
TWI229674B (en) | 1998-12-04 | 2005-03-21 | Astra Pharma Prod | Novel triazolo[4,5-d]pyrimidine compounds, pharmaceutical composition containing the same, their process for preparation and uses |
GB0013488D0 (en) * | 2000-06-02 | 2000-07-26 | Astrazeneca Ab | Chemical compound |
US6818720B2 (en) * | 2001-11-08 | 2004-11-16 | Degussa Ag | Supported hydrogenating catalyst in powder form |
SE0401001D0 (sv) * | 2004-03-31 | 2004-03-31 | Astrazeneca Ab | Chemical process |
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