CN1800160A - 3-氨基-4-烷胺基苯甲砜的制备方法 - Google Patents
3-氨基-4-烷胺基苯甲砜的制备方法 Download PDFInfo
- Publication number
- CN1800160A CN1800160A CN 200510060991 CN200510060991A CN1800160A CN 1800160 A CN1800160 A CN 1800160A CN 200510060991 CN200510060991 CN 200510060991 CN 200510060991 A CN200510060991 A CN 200510060991A CN 1800160 A CN1800160 A CN 1800160A
- Authority
- CN
- China
- Prior art keywords
- alkylamino
- nitrobenzoyl
- sulfone
- amido
- lauseto neu
- 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
Links
- 238000002360 preparation method Methods 0.000 title claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 46
- SAOGOJANGOKVRG-UHFFFAOYSA-N 1-chloro-4-(chloromethylsulfonyl)benzene Chemical compound ClCS(=O)(=O)C1=CC=C(Cl)C=C1 SAOGOJANGOKVRG-UHFFFAOYSA-N 0.000 claims abstract description 30
- 150000001243 acetic acids Chemical class 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 150000001412 amines Chemical class 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 239000002994 raw material Substances 0.000 claims abstract description 4
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 150000003457 sulfones Chemical class 0.000 claims description 27
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- OPVAJMAHHKGELS-UHFFFAOYSA-N C1=CC(=C(C=C1C(=O)S(=O)(=O)C(=O)C2=CC(=C(C=C2)Cl)[N+](=O)[O-])[N+](=O)[O-])Cl Chemical compound C1=CC(=C(C=C1C(=O)S(=O)(=O)C(=O)C2=CC(=C(C=C2)Cl)[N+](=O)[O-])[N+](=O)[O-])Cl OPVAJMAHHKGELS-UHFFFAOYSA-N 0.000 claims description 21
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical group [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 9
- 238000006396 nitration reaction Methods 0.000 claims description 9
- 239000000852 hydrogen donor Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 6
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 6
- 150000005826 halohydrocarbons Chemical class 0.000 claims description 6
- 238000006722 reduction reaction Methods 0.000 claims description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 239000007868 Raney catalyst Substances 0.000 claims description 5
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical group [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 5
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- VDLWSAISTMYDDE-UHFFFAOYSA-N 2-chlorobenzenesulfinic acid Chemical compound OS(=O)C1=CC=CC=C1Cl VDLWSAISTMYDDE-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- 239000003849 aromatic solvent Substances 0.000 claims description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 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 claims description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical group OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 3
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 claims description 3
- 235000019252 potassium sulphite Nutrition 0.000 claims description 3
- 235000010265 sodium sulphite Nutrition 0.000 claims description 3
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 2
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- KDPAWGWELVVRCH-UHFFFAOYSA-N bromoacetic acid Chemical compound OC(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-N 0.000 claims description 2
- 238000006482 condensation reaction Methods 0.000 claims description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 claims description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 claims description 2
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 claims description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 2
- JOYKCMAPFCSKNO-UHFFFAOYSA-N chloro benzenesulfonate Chemical compound ClOS(=O)(=O)C1=CC=CC=C1 JOYKCMAPFCSKNO-UHFFFAOYSA-N 0.000 abstract 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 abstract 1
- 230000006835 compression Effects 0.000 abstract 1
- 238000007906 compression Methods 0.000 abstract 1
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- BBDNZMUIQBRBJH-UHFFFAOYSA-N sulfurochloridic acid;toluene Chemical compound OS(Cl)(=O)=O.CC1=CC=CC=C1 BBDNZMUIQBRBJH-UHFFFAOYSA-N 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 description 16
- 230000002194 synthesizing effect Effects 0.000 description 15
- 238000010792 warming Methods 0.000 description 15
- 239000007787 solid Substances 0.000 description 12
- 229960004756 ethanol Drugs 0.000 description 11
- 238000009835 boiling Methods 0.000 description 10
- 238000010907 mechanical stirring Methods 0.000 description 8
- 238000000967 suction filtration Methods 0.000 description 8
- CYKLDJQISJQTQD-UHFFFAOYSA-N CNC1=C(C=C(C=C1)C(=O)S(=O)(=O)C(=O)C2=CC(=C(C=C2)NC)[N+](=O)[O-])[N+](=O)[O-] Chemical compound CNC1=C(C=C(C=C1)C(=O)S(=O)(=O)C(=O)C2=CC(=C(C=C2)NC)[N+](=O)[O-])[N+](=O)[O-] CYKLDJQISJQTQD-UHFFFAOYSA-N 0.000 description 6
- 239000012295 chemical reaction liquid Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- OZGLJFIIGIZDBK-UHFFFAOYSA-N 2-chlorobenzenesulfinic acid;sodium Chemical compound [Na].OS(=O)C1=CC=CC=C1Cl OZGLJFIIGIZDBK-UHFFFAOYSA-N 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000012065 filter cake Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 229960000935 dehydrated alcohol Drugs 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- ULEAQRIQMIQDPJ-UHFFFAOYSA-N butane-1,2-diamine Chemical compound CCC(N)CN ULEAQRIQMIQDPJ-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- -1 V-Brite B 4-methylamino 3-nitrobenzoyl sulfone Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
R1 | R2 |
H | CH3 |
CH3 | CH3 |
H | CH3CH2 |
CH3CH2 | CH3CH2 |
H | CH3CH2CH2 |
H | (CH3)2CH |
H | CH3CH2CH2CH2 |
Claims (8)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2005100609913A CN100339365C (zh) | 2005-10-08 | 2005-10-08 | 3-氨基-4-烷氨基苯甲砜的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2005100609913A CN100339365C (zh) | 2005-10-08 | 2005-10-08 | 3-氨基-4-烷氨基苯甲砜的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1800160A true CN1800160A (zh) | 2006-07-12 |
CN100339365C CN100339365C (zh) | 2007-09-26 |
Family
ID=36810413
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB2005100609913A Expired - Fee Related CN100339365C (zh) | 2005-10-08 | 2005-10-08 | 3-氨基-4-烷氨基苯甲砜的制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN100339365C (zh) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102442929A (zh) * | 2011-11-18 | 2012-05-09 | 苏州诚和医药化学有限公司 | 一种制备4-(2-羟基乙基砜)乙酰苯胺的方法 |
CN103224438A (zh) * | 2013-04-07 | 2013-07-31 | 辽宁大学 | Dmf亲核取代合成n,n-二甲基胺类化合物的方法 |
CN103709095A (zh) * | 2014-01-14 | 2014-04-09 | 浙江永宁药业股份有限公司 | 4-环内酰胺基苯胺的制备方法 |
CN105837528A (zh) * | 2016-05-30 | 2016-08-10 | 大连理工大学 | 一种2-(甲基磺酰基)-10h-吩噻嗪的制备方法 |
CN109134321A (zh) * | 2018-10-22 | 2019-01-04 | 江苏长青农化股份有限公司 | 一种甲基磺草酮中间体的制备方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61210063A (ja) * | 1985-03-14 | 1986-09-18 | Mitsubishi Chem Ind Ltd | アリ−ルスルホン類 |
-
2005
- 2005-10-08 CN CNB2005100609913A patent/CN100339365C/zh not_active Expired - Fee Related
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102442929A (zh) * | 2011-11-18 | 2012-05-09 | 苏州诚和医药化学有限公司 | 一种制备4-(2-羟基乙基砜)乙酰苯胺的方法 |
CN103224438A (zh) * | 2013-04-07 | 2013-07-31 | 辽宁大学 | Dmf亲核取代合成n,n-二甲基胺类化合物的方法 |
CN103709095A (zh) * | 2014-01-14 | 2014-04-09 | 浙江永宁药业股份有限公司 | 4-环内酰胺基苯胺的制备方法 |
CN103709095B (zh) * | 2014-01-14 | 2016-06-22 | 浙江永宁药业股份有限公司 | 4-环内酰胺基苯胺的制备方法 |
CN105837528A (zh) * | 2016-05-30 | 2016-08-10 | 大连理工大学 | 一种2-(甲基磺酰基)-10h-吩噻嗪的制备方法 |
CN109134321A (zh) * | 2018-10-22 | 2019-01-04 | 江苏长青农化股份有限公司 | 一种甲基磺草酮中间体的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN100339365C (zh) | 2007-09-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN100339365C (zh) | 3-氨基-4-烷氨基苯甲砜的制备方法 | |
CN1226293C (zh) | 2-(2-羟苯基)-2氢-苯并三唑的制备方法 | |
CN111848406B (zh) | 一种2-氯-4-氟-5-硝基苯甲醛的制备方法 | |
CN1046701C (zh) | 制备取代的芳香胺类的方法 | |
CN101037380A (zh) | 2,3-二氟-5-溴苯酚的制备方法 | |
EP3601262B1 (en) | Process for the preparation of a sulfonamide structured kinase inhibitor | |
CN1267410C (zh) | 制备环己醇衍生物的方法 | |
EP2373654A1 (en) | Process for the preparation of anagrelide and analogues | |
CN1209341C (zh) | 一种制备2,6-二氯-4-三氟甲基苯胺的新方法 | |
CN112409275B (zh) | 一种光催化的3-酰基喹喔啉酮化合物的制备方法 | |
CN112321385A (zh) | 一种可见光催化的三氟甲基烯烃衍生物的制备方法 | |
KR101416450B1 (ko) | 신규한 포타슘 오가노-1h-1,2,3-트리아졸-4-일트리플루오로보레이트 유도체 및 그 제조방법 | |
CN114014766B (zh) | 一种盐酸多巴胺中间体2-(3,4-二甲氧基苯基)乙胺的制备方法 | |
CN1131661A (zh) | 制备4,6-二氨基间苯二酚的方法 | |
CN112625257B (zh) | MOF-Cu的制备方法及其在二芳基砜类化合物合成中的应用 | |
CN101058554A (zh) | 一种磺酰基取代α,β不饱和酮的化学合成方法 | |
JP5549840B2 (ja) | テトラアミノベンゼン誘導体の製造方法およびその中間体 | |
TWI797784B (zh) | 環戊二烯的選擇性烷基化 | |
CN1280268C (zh) | 制备双卤代苯基二硫化物的方法 | |
CN1125034C (zh) | 制备4,6-二氨基间苯二酚二氢氯化物的方法 | |
CN1578764A (zh) | 2-[烷基(芳基)]磺酰基苯磺酰氯及其中间体的制备方法 | |
CN114539080A (zh) | 一种2-(2-氨基-6-氯苯基)-乙酸钠的制备方法 | |
CN1656055A (zh) | 2-苄基苯胺的制造方法 | |
WO2012052781A1 (en) | Process for the preparation of anagrelide and analogues thereof | |
CN1265095A (zh) | 制备n-(5-氨基-2-氰基-4-氟苯基)磺酰胺的方法和新的中间体 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Owner name: HANGZHOU SHENYING MEDICINE CHEMICAL ENGINEERING C Free format text: FORMER OWNER: ZHEJIANG UNIVERSITY Effective date: 20080808 |
|
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20080808 Address after: New bay, Xiaoshan District, Hangzhou, Zhejiang Patentee after: Shenying Medicinal Chemicals Co., Ltd., Hangzhou City Address before: No. 38, Zhejiang Road, Hangzhou, Zhejiang, Xihu District Patentee before: Zhejiang University |
|
ASS | Succession or assignment of patent right |
Owner name: HANGZHOU SHENYING PHARMACEUTICAL CO., LTD. Free format text: FORMER OWNER: SHENYING MEDICINAL CHEMICALS CO., LTD., HANGZHOU CITY Effective date: 20141204 |
|
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20141204 Address after: 311228, two, No. 478 farm, Linjiang hi tech Industrial Park, Xiaoshan District, Zhejiang, Hangzhou Patentee after: Hangzhou Eagle Pharmaceutical Co. Ltd. Address before: 311228 new Bay Town, Xiaoshan District, Zhejiang, Hangzhou Patentee before: Shenying Medicinal Chemicals Co., Ltd., Hangzhou City |
|
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20070926 Termination date: 20181008 |
|
CF01 | Termination of patent right due to non-payment of annual fee |