CN1276911C - 具有β2-受体兴奋作用的新型苯乙醇胺类化合物及其制法 - Google Patents
具有β2-受体兴奋作用的新型苯乙醇胺类化合物及其制法 Download PDFInfo
- Publication number
- CN1276911C CN1276911C CNB011282347A CN01128234A CN1276911C CN 1276911 C CN1276911 C CN 1276911C CN B011282347 A CNB011282347 A CN B011282347A CN 01128234 A CN01128234 A CN 01128234A CN 1276911 C CN1276911 C CN 1276911C
- Authority
- CN
- China
- Prior art keywords
- compound
- amino
- preparation
- dmso
- novel
- 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.)
- Expired - Fee Related
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- -1 phenylethanolamine compound Chemical class 0.000 title abstract description 4
- ULSIYEODSMZIPX-UHFFFAOYSA-N alpha-hydroxyphenethylamine Natural products NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 title abstract 3
- 102000016966 beta-2 Adrenergic Receptors Human genes 0.000 title abstract 3
- 108010014499 beta-2 Adrenergic Receptors Proteins 0.000 title abstract 3
- 229950006768 phenylethanolamine Drugs 0.000 title abstract 3
- 230000002964 excitative effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 230000005284 excitation Effects 0.000 claims abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000010992 reflux Methods 0.000 claims abstract description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 4
- 239000007810 chemical reaction solvent Substances 0.000 claims abstract description 4
- 150000007925 phenylethylamine derivatives Chemical class 0.000 claims description 7
- 230000035484 reaction time Effects 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 150000001298 alcohols Chemical group 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 239000012188 paraffin wax Substances 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 5
- 206010006451 bronchitis Diseases 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 15
- PMUNIMVZCACZBB-UHFFFAOYSA-N 2-hydroxyethylazanium;chloride Chemical compound Cl.NCCO PMUNIMVZCACZBB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- YETXOGOWALBMMQ-UHFFFAOYSA-N Cl.C(O)CN.C(O)CN.C(O)CN.C(O)CN.C(O)CN Chemical compound Cl.C(O)CN.C(O)CN.C(O)CN.C(O)CN.C(O)CN YETXOGOWALBMMQ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229960000935 dehydrated alcohol Drugs 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical class CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- AKPUJVVHYUHGKY-UHFFFAOYSA-N hydron;propan-2-ol;chloride Chemical class Cl.CC(C)O AKPUJVVHYUHGKY-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/68—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings and hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/04—Drugs for disorders of the respiratory system for throat disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
- C07C255/59—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Pulmonology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Otolaryngology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB011282347A CN1276911C (zh) | 2001-09-30 | 2001-09-30 | 具有β2-受体兴奋作用的新型苯乙醇胺类化合物及其制法 |
| DE60219500T DE60219500T2 (de) | 2001-09-30 | 2002-09-25 | Neue phenylethanolaminverbindungen mit erregender wirkung an beta2-akzeptor und verfahren zu deren herstellung |
| RU2004112212/04A RU2264382C1 (ru) | 2001-09-30 | 2002-09-25 | Новые фенилэтаноламиновые соединения в качестве агонистов и бета2-рецептора и способ их получения |
| DK02771983T DK1439164T3 (da) | 2001-09-30 | 2002-09-25 | Hidtil ukendte phenylethanolaminforbindelser, der har beta2- acceptorexcitatorisk funktion, og deres fremstillingsmetode |
| JP2004501359A JP3990399B2 (ja) | 2001-09-30 | 2002-09-25 | β2−受容体興奮作用を有する新規フェニルエタノールアミン類化合物及びそれらの製造方法 |
| AU2002338124A AU2002338124A1 (en) | 2001-09-30 | 2002-09-25 | NOVEL PHENYLETHANOLAMINE COMPOUNDS HAVING Beta2-ACCEPTOR EXCITATORY FUNCTION AND THEIR PREPARATION METHOD |
| PCT/CN2002/000676 WO2003093219A1 (en) | 2001-09-30 | 2002-09-25 | NOVEL PHENYLETHANOLAMINE COMPOUNDS HAVING β2-ACCEPTOR EXCITATORY FUNCTION AND THEIR PREPARATION METHOD |
| EP02771983A EP1439164B1 (en) | 2001-09-30 | 2002-09-25 | Novel phenylethanolamine compounds having beta2-acceptor excitatory function and their preparation method |
| AT02771983T ATE359261T1 (de) | 2001-09-30 | 2002-09-25 | Neue phenylethanolaminverbindungen mit erregender wirkung an beta2-akzeptor und verfahren zu deren herstellung |
| ES02771983T ES2284926T3 (es) | 2001-09-30 | 2002-09-25 | Nuevos compuestos de feniltanolaminas con una funcion de exticion de un receptor beta2 y metodo para su preparacion. |
| US10/491,028 US7098364B2 (en) | 2001-09-30 | 2002-09-25 | Phenylethanolamine compounds as β2-receptor agonists, and methods of use and preparation thereof |
| HK04107530.8A HK1064664B (en) | 2001-09-30 | 2002-09-25 | Novel phenylethanolamine compounds having beta2-acceptor excitatory function and their preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB011282347A CN1276911C (zh) | 2001-09-30 | 2001-09-30 | 具有β2-受体兴奋作用的新型苯乙醇胺类化合物及其制法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1408703A CN1408703A (zh) | 2003-04-09 |
| CN1276911C true CN1276911C (zh) | 2006-09-27 |
Family
ID=4668112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB011282347A Expired - Fee Related CN1276911C (zh) | 2001-09-30 | 2001-09-30 | 具有β2-受体兴奋作用的新型苯乙醇胺类化合物及其制法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7098364B2 (https=) |
| EP (1) | EP1439164B1 (https=) |
| JP (1) | JP3990399B2 (https=) |
| CN (1) | CN1276911C (https=) |
| AT (1) | ATE359261T1 (https=) |
| AU (1) | AU2002338124A1 (https=) |
| DE (1) | DE60219500T2 (https=) |
| DK (1) | DK1439164T3 (https=) |
| ES (1) | ES2284926T3 (https=) |
| RU (1) | RU2264382C1 (https=) |
| WO (1) | WO2003093219A1 (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100497296C (zh) * | 2006-07-07 | 2009-06-10 | 沈阳药科大学 | 旋光活性的苯乙醇胺类化合物及其制法 |
| CN100431535C (zh) * | 2006-09-18 | 2008-11-12 | 锦州九泰药业有限责任公司 | 一种盐酸川丁特罗气雾剂 |
| EP1969929A1 (de) * | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | Substituierte Phenylamidine und deren Verwendung als Fungizide |
| CN102477000B (zh) * | 2010-11-24 | 2013-11-06 | 沈阳药科大学 | 一种苯乙醇胺类化合物的合成方法 |
| US9784726B2 (en) | 2013-01-08 | 2017-10-10 | Atrogi Ab | Screening method, a kit, a method of treatment and a compound for use in a method of treatment |
| CN106279018B (zh) * | 2015-06-26 | 2019-01-29 | 沈阳药科大学 | β2-受体兴奋剂及其制备方法和应用 |
| GB201714736D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201714745D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201714734D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201714740D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201903832D0 (en) | 2019-03-20 | 2019-05-01 | Atrogi Ab | New compounds and methods |
| GB202205895D0 (en) | 2022-04-22 | 2022-06-08 | Atrogi Ab | New medical uses |
| EP4651867A1 (en) | 2023-01-20 | 2025-11-26 | Atrogi AB | Beta 2-adrenergic receptor agonists for treatment or prevention of muscle wasting |
| GB202302225D0 (en) | 2023-02-16 | 2023-04-05 | Atrogi Ab | New medical uses |
| GB202303229D0 (en) | 2023-03-06 | 2023-04-19 | Atrogi Ab | New medical uses |
| GB202403169D0 (en) | 2024-03-05 | 2024-04-17 | Atrogi Ab | New medical uses |
| WO2025238248A1 (en) | 2024-05-17 | 2025-11-20 | Atrogi Ab | USE OF β2-ADRENERGIC RECEPTOR AGONISTS IN TREATING MUSCLE WASTING |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4028398A1 (de) * | 1990-09-07 | 1992-03-12 | Thomae Gmbh Dr K | Phenylethanolamine, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| SG55296A1 (en) * | 1996-04-12 | 1998-12-21 | Kissei Pharmaceutical | Phenylethalolaminotetralincarboxamide derivatives |
| CN1237574A (zh) * | 1998-05-29 | 1999-12-08 | 中国科学院成都有机化学研究所 | 合成苯乙醇胺类化合物的方法 |
-
2001
- 2001-09-30 CN CNB011282347A patent/CN1276911C/zh not_active Expired - Fee Related
-
2002
- 2002-09-25 DK DK02771983T patent/DK1439164T3/da active
- 2002-09-25 AT AT02771983T patent/ATE359261T1/de not_active IP Right Cessation
- 2002-09-25 DE DE60219500T patent/DE60219500T2/de not_active Expired - Lifetime
- 2002-09-25 WO PCT/CN2002/000676 patent/WO2003093219A1/zh not_active Ceased
- 2002-09-25 US US10/491,028 patent/US7098364B2/en not_active Expired - Lifetime
- 2002-09-25 RU RU2004112212/04A patent/RU2264382C1/ru active
- 2002-09-25 AU AU2002338124A patent/AU2002338124A1/en not_active Abandoned
- 2002-09-25 JP JP2004501359A patent/JP3990399B2/ja not_active Expired - Fee Related
- 2002-09-25 ES ES02771983T patent/ES2284926T3/es not_active Expired - Lifetime
- 2002-09-25 EP EP02771983A patent/EP1439164B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1439164A1 (en) | 2004-07-21 |
| US7098364B2 (en) | 2006-08-29 |
| CN1408703A (zh) | 2003-04-09 |
| DK1439164T3 (da) | 2007-08-20 |
| ES2284926T3 (es) | 2007-11-16 |
| WO2003093219A1 (en) | 2003-11-13 |
| JP2005519989A (ja) | 2005-07-07 |
| JP3990399B2 (ja) | 2007-10-10 |
| DE60219500T2 (de) | 2007-12-13 |
| HK1064664A1 (en) | 2005-02-04 |
| ATE359261T1 (de) | 2007-05-15 |
| EP1439164A4 (en) | 2005-12-21 |
| RU2004112212A (ru) | 2005-09-10 |
| AU2002338124A8 (en) | 2003-11-17 |
| US20040266867A1 (en) | 2004-12-30 |
| EP1439164B1 (en) | 2007-04-11 |
| RU2264382C1 (ru) | 2005-11-20 |
| AU2002338124A1 (en) | 2003-11-17 |
| DE60219500D1 (de) | 2007-05-24 |
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