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DE122009000031I1 - 11 beta-substituierte progesteron-analoge - Google Patents

11 beta-substituierte progesteron-analoge

Info

Publication number
DE122009000031I1
DE122009000031I1 DE122009000031C DE122009000031C DE122009000031I1 DE 122009000031 I1 DE122009000031 I1 DE 122009000031I1 DE 122009000031 C DE122009000031 C DE 122009000031C DE 122009000031 C DE122009000031 C DE 122009000031C DE 122009000031 I1 DE122009000031 I1 DE 122009000031I1
Authority
DE
Germany
Prior art keywords
beta
alkynyl
alkenyl
alkyl
defined above
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
Application number
DE122009000031C
Other languages
English (en)
Other versions
DE122009000031I2 (de
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
RTI International Inc
Original Assignee
RTI International Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by RTI International Inc filed Critical RTI International Inc
Publication of DE122009000031I1 publication Critical patent/DE122009000031I1/de
Publication of DE122009000031I2 publication Critical patent/DE122009000031I2/de
Active legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0077—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom
    • C07J41/0083—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom substituted in position 11-beta by an optionally substituted phenyl group not further condensed with other rings
    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
    • C07J13/005—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 16 (17)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
    • C07J53/002—Carbocyclic rings fused
    • C07J53/004—3 membered carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
    • C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
    • C07J7/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa
    • C07J7/002—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa not substituted in position 16
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
    • C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
    • C07J7/004—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa
    • C07J7/0045—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa not substituted in position 16
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0036—Nitrogen-containing hetero ring
    • C07J71/0042—Nitrogen only
    • C07J71/0052—Nitrogen only at position 16(17)

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Diabetes (AREA)
  • Endocrinology (AREA)
  • Urology & Nephrology (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Reproductive Health (AREA)
  • Emergency Medicine (AREA)
  • Epidemiology (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Devices For Supply Of Signal Current (AREA)
  • Control Of Eletrric Generators (AREA)
  • Sub-Exchange Stations And Push- Button Telephones (AREA)
  • Light Receiving Elements (AREA)
  • Led Devices (AREA)
  • Junction Field-Effect Transistors (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Seasonings (AREA)
  • Manufacture Of Tobacco Products (AREA)
DE122009000031C 1988-06-23 1989-06-23 11 beta-substituierte progesteron-analoge Active DE122009000031I2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US07/210,503 US4954490A (en) 1988-06-23 1988-06-23 11 β-substituted progesterone analogs
PCT/US1989/002706 WO1989012448A1 (en) 1988-06-23 1989-06-23 11beta-SUBSTITUTED PROGESTERONE ANALOGS

Publications (2)

Publication Number Publication Date
DE122009000031I1 true DE122009000031I1 (de) 2009-11-05
DE122009000031I2 DE122009000031I2 (de) 2011-06-16

Family

ID=22783162

Family Applications (2)

Application Number Title Priority Date Filing Date
DE122009000031C Active DE122009000031I2 (de) 1988-06-23 1989-06-23 11 beta-substituierte progesteron-analoge
DE68927861T Expired - Lifetime DE68927861T2 (de) 1988-06-23 1989-06-23 11 beta-substituierte progesteron-analoge

Family Applications After (1)

Application Number Title Priority Date Filing Date
DE68927861T Expired - Lifetime DE68927861T2 (de) 1988-06-23 1989-06-23 11 beta-substituierte progesteron-analoge

Country Status (13)

Country Link
US (2) US4954490A (de)
EP (1) EP0422100B1 (de)
JP (1) JP2953725B2 (de)
KR (1) KR0161975B1 (de)
AT (1) ATE149839T1 (de)
AU (1) AU635211B2 (de)
CA (1) CA1338906C (de)
DE (2) DE122009000031I2 (de)
DK (1) DK175760B1 (de)
LU (1) LU91575I2 (de)
NL (1) NL300392I2 (de)
NO (2) NO178264C (de)
WO (1) WO1989012448A1 (de)

Families Citing this family (90)

* Cited by examiner, † Cited by third party
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DE3832303A1 (de) * 1988-09-20 1990-04-12 Schering Ag 11ss-phenyl-14ssh-steroide
ES2127181T3 (es) * 1989-08-04 1999-04-16 Schering Ag 11-beta-aril-gona-4,9-dien-3-onas.
USRE34578E (en) * 1990-05-07 1994-04-05 Lubkin; Virginia Drugs for topical application of sex steroids in the treatment of dry eye syndrome, and methods of preparation and application
US5041434A (en) * 1991-08-17 1991-08-20 Virginia Lubkin Drugs for topical application of sex steroids in the treatment of dry eye syndrome, and methods of preparation and application
DE4042004A1 (de) * 1990-12-22 1992-06-25 Schering Ag 14(beta)-h-, 14- u. 15-en-11(beta)-aryl-4-estrene
US5407928A (en) * 1990-08-15 1995-04-18 Schering Aktiengesellschaft 11β-aryl-gona-4,9-dien-3-ones
WO1993020823A1 (en) * 1992-04-21 1993-10-28 The Schepens Eye Research Institute, Inc. Ocular androgen therapy in sjögren's syndrome
US5536725A (en) * 1993-08-25 1996-07-16 Fmc Corporation Insecticidal substituted-2,4-diamino-5,6,7,8-tetrahydroquinazolines
US5780220A (en) * 1994-05-19 1998-07-14 Trustees Of The University Of Pennsylvania Methods and compositions for inhibiting HIV replication
US5639598A (en) * 1994-05-19 1997-06-17 The Trustees Of The University Of Pennsylvania Method and kit for identification of antiviral agents capable of abrogating HIV Vpr-Rip-1 binding interactions
CA2149496C (en) * 1994-05-19 2006-12-19 Ronald Gebhard 11,21-bisphenyl-19-norpregnane derivatives
US5929262A (en) * 1995-03-30 1999-07-27 The United States Of America As Represented By The Department Of Health And Human Services Method for preparing 17α-acetoxy-11β-(4-N, N-dimethylaminophyl)-19-Norpregna-4,9-diene-3, 20-dione, intermediates useful in the method, and methods for the preparation of such intermediates
JP4260886B2 (ja) * 1996-05-01 2009-04-30 アメリカ合衆国 新規の抗プロゲステロンとしての２１―置換プロゲステロン誘導体
US6900193B1 (en) * 1996-05-01 2005-05-31 The United States Of America As Represented By The Department Of Health And Human Services Structural modification of 19-norprogesterone I: 17-α-substituted-11-β-substituted-4-aryl and 21-substituted 19-norpregnadienedione as new antiprogestational agents
WO1998005679A2 (en) * 1996-08-05 1998-02-12 Duke University Mixed agonists of the progesterone receptor and assays therefor
US6090798A (en) * 1997-12-19 2000-07-18 Alcon Laboratories, Inc. Treatment of GLC1A glaucoma with glucocorticoid antagonists
US6020328A (en) * 1998-03-06 2000-02-01 Research Triangle Institute 20-keto-11β-arylsteroids and their derivatives having agonist or antagonist hormonal properties
US5962444A (en) * 1998-05-29 1999-10-05 Research Triangle Institute 17β-nitro-11β-arylsteroids and their derivatives having agonist or antagonist hormonal properties
US6262042B1 (en) 1998-05-29 2001-07-17 Research Triangle Institute 17β-amino and hydroxylamino-11β-arylsteroids and their derivatives having agonist or antagonist hormonal properties
US6172052B1 (en) * 1998-12-04 2001-01-09 Research Triangle Institute 17β-acyl-17α-propynyl-11β-arylsteroids and their derivatives having agonist or antagonist hormonal properties
US6740645B1 (en) * 1999-09-03 2004-05-25 Research Triangle Institute 17β-acyl-17α-propynyl-11β-(cyclic amino) aryl steroids and their derivatives having antagonist hormonal properties
WO2001074840A2 (en) * 2000-03-17 2001-10-11 The Government Of The United States Of America As Represented By The Secretary Of Health And Human Services 17-alpha-substituted-11-beta-substituted-4-aryl and 21-substituted 19-norpregna 21-substituted 19-norpregnadienedione as antiprogestational agents
ATE437853T1 (de) * 2001-02-14 2009-08-15 Karobio Ab Glucocorticoid-rezeptoren-modulatoren
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PT2148681E (pt) * 2007-04-20 2016-06-17 Preglem Sa Moduladores seletivos da progesterona no tratamento da hemorragia uterina
HU228636B1 (en) * 2007-06-27 2013-04-29 Richter Gedeon Nyrt Industrial method for the synthesis of 17-acetoxy-11betha-4[-(dimethylamino)-phenyl]-21-methoxy-19-norpregna-4,9-dien-3,20-dione and the key intermediates of the process
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US8512745B2 (en) * 2008-12-08 2013-08-20 Laboratoire Hra Pharma Ulipristal acetate tablets
AU2010237120B8 (en) 2009-04-14 2015-11-26 Laboratoire Hra-Pharma Method for on-demand contraception
DE102009034362A1 (de) 2009-07-20 2011-01-27 Bayer Schering Pharma Aktiengesellschaft 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-aryl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Behandlung von Krankheiten
DE102009034368A1 (de) 2009-07-20 2011-01-27 Bayer Schering Pharma Aktiengesellschaft 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-acyloxyalkylenphenyl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Behandlung von Krankheiten
DE102009034366A1 (de) 2009-07-20 2011-01-27 Bayer Schering Pharma Aktiengesellschaft 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-methylenoxyalkylenaryl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Behandlung von Krankheiten
DE102009034367A1 (de) 2009-07-20 2011-01-27 Bayer Schering Pharma Aktiengesellschaft 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-benzyliden-Derivate, Verfahren zu deren Herstellung und deren Verwendung zur Behandlung von Krankheiten
DE102009034525A1 (de) 2009-07-21 2011-01-27 Bayer Schering Pharma Aktiengesellschaft 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-aryl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Behandlung von Krankheiten
DE102009034526A1 (de) 2009-07-21 2011-02-10 Bayer Schering Pharma Aktiengesellschaft 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-ethinylphenyl-Derivate, Verfahren zu deren Herstellung und deren Verwendung zur Behandlung von Krankheiten
US8426392B2 (en) 2009-12-09 2013-04-23 Laboratoire Hra-Pharma Method for providing emergency contraception
WO2011091890A1 (en) 2010-02-01 2011-08-04 Laboratoire Hra-Pharma A method for post coital contraception in overweight for obese female subjects using ulipristal acetate
US20130045959A1 (en) 2010-02-01 2013-02-21 Andre Ulmann Method for late post coital contraception using ulipristal acetate
DE102010007719A1 (de) 2010-02-10 2011-08-11 Bayer Schering Pharma Aktiengesellschaft, 13353 Progesteronrezeptorantagonisten
DE102010007722A1 (de) 2010-02-10 2011-08-11 Bayer Schering Pharma Aktiengesellschaft, 13353 Progesteronrezeptorantagonisten
KR20130009990A (ko) * 2010-03-22 2013-01-24 레프로스 쎄라피우틱스 아이엔씨. 항프로게스틴의 비독성 전달을 위한 조성물들과 그 방법들
ES2762243T3 (es) 2010-05-26 2020-05-22 Corcept Therapeutics Inc Tratamiento de distrofia muscular
CN102372760A (zh) * 2010-08-12 2012-03-14 杭州容立医药科技有限公司 一种合成孕酮受体调节剂优力司特的合成方法
UA113283C2 (xx) * 2010-12-23 2017-01-10 19-норстероїди і їх застосування для лікування прогестеронзалежних станів
EP2471537A1 (de) 2010-12-30 2012-07-04 PregLem S.A. Behandlung von Schmerz in Verbindung mit der Dislokation des basalen Endometriums
CN102516345B (zh) 2011-11-01 2014-11-26 上海优拓医药科技有限公司 醋酸乌利司他及其关键中间体的制备方法
CN102617692A (zh) * 2011-01-31 2012-08-01 北京紫竹药业有限公司 甾体化合物及其制备方法和用途
EP2545922A1 (de) 2011-07-12 2013-01-16 PregLem S.A. Behandlung von übermäßiger Monatsblutung im Zusammenhang mit Gebärmutterfibromen
CN102321141B (zh) 2011-07-22 2013-05-15 上海希迈医药科技有限公司 一种17α-乙酰氧基-11β-（4-N,N-二甲氨基苯基）-19-去甲孕甾-4，9-二烯-3,20-二酮的无定形物及其制备方法
CN102344478B (zh) * 2011-07-22 2013-08-07 上海希迈医药科技有限公司 一种17α-乙酰氧基-11β-(4-N,N-二甲氨基苯基)-19-去甲孕甾-4,9-二烯-3,20-二酮的结晶物及其制备方法
CN104628806A (zh) * 2012-01-19 2015-05-20 华润紫竹药业有限公司 甾体化合物及其制备方法和用途
FR2987271B1 (fr) 2012-02-28 2017-08-18 Hra Pharma Lab Combinaison de modulateurs selectifs du recepteur a la progesterone et d'anti-inflammatoires non steroidiens
EP2641602A1 (de) 2012-03-23 2013-09-25 PregLem S.A. Verfahren zur Behandlung gynäkologischer Leiden
CN102675395B (zh) * 2012-04-17 2014-04-30 常州市第四制药厂有限公司 醋酸乌利司他的多晶型及其制备方法
WO2013175009A1 (en) 2012-05-25 2013-11-28 Laboratoire Hra-Pharma Ulipristal acetate for prevention and treatment of breast tumors
MX382986B (es) 2012-05-31 2025-03-13 Repros Therapeutics Inc El uso de una cápsula mucoadherente que comprende pululano y cdb-2914 para el tratamiento de un trastorno dependiente de la progesterona
CN102702296B (zh) * 2012-06-19 2014-09-03 山东诚创医药技术开发有限公司 环-3,20-双(1,2-亚乙基缩醛)-17α-羟基-17β-乙酰基-雌甾-5(10),9(11)-二烯-3-酮的制备方法
JP6200493B2 (ja) 2012-09-28 2017-09-20 あすか製薬株式会社 無定形ウリプリスタール酢酸エステル
JP2015532263A (ja) 2012-09-28 2015-11-09 あすか製薬株式会社 ウリプリスタール酢酸エステルの結晶多形
KR20150063486A (ko) 2012-09-28 2015-06-09 아스카 세이야쿠 가부시키가이샤 울리프리스탈 아세테이트의 결정질 다형 형태
WO2014060888A1 (en) 2012-10-18 2014-04-24 Lupin Limited Novel process and intermediate for preparation of ulipristal
CN103772468B (zh) * 2012-10-19 2017-04-05 华润紫竹药业有限公司 醋酸特拉司酮及其中间体的制备方法和用途
CN104755087A (zh) 2012-11-02 2015-07-01 利普生物药剂公司 治疗孕酮依赖性病况的方法和组合物
FR2997628B1 (fr) * 2012-11-08 2015-01-16 Hra Pharma Lab Produit de co-micronisation comprenant un modulateur selectif des recepteurs a la progesterone
FR2997627B1 (fr) * 2012-11-08 2015-01-16 Hra Pharma Lab Produit de co-micronisation comprenant de l'ulipristal acetate
FR2999081B1 (fr) 2012-12-06 2015-02-27 Hra Pharma Lab Dispersion solide d'un modulateur selectif du recepteur a la progesterone
CN103073612B (zh) * 2013-02-04 2015-11-04 山东大学 醋酸乌利司他关键中间体的制备方法
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NL300392I2 (nl) 2009-10-01
WO1989012448A1 (en) 1989-12-28
KR0161975B1 (ko) 1998-11-16
NO2009014I1 (no) 2009-07-06
US5073548A (en) 1991-12-17
NO178264B (no) 1995-11-13
DK175760B1 (da) 2005-02-14
NO905546D0 (no) 1990-12-21
AU635211B2 (en) 1993-03-18
CA1338906C (en) 1997-02-11
EP0422100A4 (de) 1994-04-27
DE68927861D1 (de) 1997-04-17
EP0422100A1 (de) 1991-04-17
DE122009000031I2 (de) 2011-06-16
NO178264C (no) 1996-02-21
EP0422100B1 (de) 1997-03-12
NO905546L (no) 1990-12-21
LU91575I2 (fr) 2009-08-03
DK305390A (da) 1990-12-21
AU3850689A (en) 1990-01-12
DK305390D0 (da) 1990-12-21
NL300392I1 (nl) 2009-08-03
JP2953725B2 (ja) 1999-09-27
US4954490A (en) 1990-09-04
KR900701820A (ko) 1990-12-04
JPH03505582A (ja) 1991-12-05
NO2009014I2 (no) 2009-12-28
ATE149839T1 (de) 1997-03-15
DE68927861T2 (de) 1997-10-16

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