DK0516410T3 - Hidtil ukendt syntese af 19-nor-vitamin D-forbindelser - Google Patents

Hidtil ukendt syntese af 19-nor-vitamin D-forbindelser

Info

Publication number
DK0516410T3
DK0516410T3 DK92304837T DK92304837T DK0516410T3 DK 0516410 T3 DK0516410 T3 DK 0516410T3 DK 92304837 T DK92304837 T DK 92304837T DK 92304837 T DK92304837 T DK 92304837T DK 0516410 T3 DK0516410 T3 DK 0516410T3
Authority
DK
Denmark
Prior art keywords
vitamin
compounds
synthesis
hitherto unknown
alpha
Prior art date
Application number
DK92304837T
Other languages
English (en)
Inventor
Hector Floyd Deluca
Heinrich Konstantine Schnoes
Kato Leonard Perlman
Rolf E Swenson
Original Assignee
Wisconsin Alumni Res Found
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 Wisconsin Alumni Res Found filed Critical Wisconsin Alumni Res Found
Application granted granted Critical
Publication of DK0516410T3 publication Critical patent/DK0516410T3/da

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C401/00Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/18Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804Compounds having Si-O-C linkages
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/50Organo-phosphines
    • C07F9/53Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/532Cycloaliphatic phosphine oxides or thioxides
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
DK92304837T 1991-05-28 1992-05-28 Hidtil ukendt syntese af 19-nor-vitamin D-forbindelser DK0516410T3 (da)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US70591791A 1991-05-28 1991-05-28

Publications (1)

Publication Number Publication Date
DK0516410T3 true DK0516410T3 (da) 1998-10-26

Family

ID=24835479

Family Applications (1)

Application Number Title Priority Date Filing Date
DK92304837T DK0516410T3 (da) 1991-05-28 1992-05-28 Hidtil ukendt syntese af 19-nor-vitamin D-forbindelser

Country Status (11)

Country Link
US (7) US5281731A (da)
EP (1) EP0516410B1 (da)
JP (4) JP2648845B2 (da)
KR (3) KR0160784B1 (da)
AT (1) ATE168996T1 (da)
AU (2) AU650751B2 (da)
CA (2) CA2191993C (da)
DE (1) DE69226402T2 (da)
DK (1) DK0516410T3 (da)
ES (1) ES2118794T3 (da)
IE (1) IE921700A1 (da)

Families Citing this family (66)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1333616C (en) * 1989-03-09 1994-12-20 Hector F. Deluca 19-nor-vitamin d compounds
US5260290A (en) * 1990-02-14 1993-11-09 Wisconsin Alumni Research Foundation Homologated vitamin D2 compounds and the corresponding 1α-hydroxylated derivatives
US20040009958A1 (en) * 1991-01-08 2004-01-15 Bone Care International, Inc. Methods for preparation and use of 1alpha,24(S)-dihydroxyvitamin D2
US6538037B2 (en) 1991-01-08 2003-03-25 Bone Care International, Inc. Methods for preparation and use of 1α,24(S)-dihydroxyvitamin D2
AU650751B2 (en) * 1991-05-28 1994-06-30 Wisconsin Alumni Research Foundation Novel synthesis of 19-nor vitamin D compounds
AU666563B2 (en) * 1992-08-07 1996-02-15 Wisconsin Alumni Research Foundation Preparation of 19-nor-vitamin D compounds
US5464866A (en) * 1992-08-17 1995-11-07 Alcon Laboratories, Inc. Substituted hydrindanes for the treatment of angiogenesis-dependent diseases
CA2096105A1 (en) * 1992-10-07 1994-04-08 Enrico Giuseppe Baggiolini (Deceased) Vitamin d3 fluorinated analogs
US5753638A (en) * 1992-10-07 1998-05-19 Hoffmann-La Roche Inc. Method of treating hyperproliferative skin disease with Vitamin D3 fluorinated analogs
DE69400495T2 (de) * 1993-04-05 1997-04-30 Wisconsin Alumni Res Found 19-Nor-vitamin-D3-Verbindung mit einem Substituent an die 2. Stelle
CA2166898C (en) * 1993-07-09 2004-09-07 Roger Bouillon Novel structural analogues of vitamin d
US5763429A (en) * 1993-09-10 1998-06-09 Bone Care International, Inc. Method of treating prostatic diseases using active vitamin D analogues
US5428029A (en) * 1993-11-24 1995-06-27 Hoffmann-La Roche Inc. Vitamin D3 fluorinated analogs
DE69507714D1 (de) * 1994-11-21 1999-03-18 Wisconsin Alumni Res Found 18,19-dinor-vitamin-d-derivate
US5597815A (en) * 1995-07-13 1997-01-28 Wisconsin Alumni Research Foundation Prevention of hyperphosphatemia in kidney disorder patients
US6573256B2 (en) 1996-12-30 2003-06-03 Bone Care International, Inc. Method of inhibiting angiogenesis using active vitamin D analogues
US20020128240A1 (en) * 1996-12-30 2002-09-12 Bone Care International, Inc. Treatment of hyperproliferative diseases using active vitamin D analogues
US6503893B2 (en) 1996-12-30 2003-01-07 Bone Care International, Inc. Method of treating hyperproliferative diseases using active vitamin D analogues
US6566353B2 (en) * 1996-12-30 2003-05-20 Bone Care International, Inc. Method of treating malignancy associated hypercalcemia using active vitamin D analogues
US5945410A (en) 1997-03-17 1999-08-31 Wisconsin Alumni Research Foundation 2-alkyl-19-nor-vitamin D compounds
US6306844B1 (en) 1997-03-17 2001-10-23 Wisconsin Alumni Research Foundation Use of 2α-methyl-19-nor-20(S)-1α, 25-dihydroxyvitamin D3 to increase bone strength
US6316642B1 (en) 1997-03-17 2001-11-13 Wisconsin Alumni Research Foundation 26,27-Homologated-20-EPI-2alkyl-19-nor-vitamin D compounds
US6392071B1 (en) 1997-03-17 2002-05-21 Wisconsin Alumni: Research Foundation 26,27-homologated-20-EPI-2-alkylidene-19-nor-vitamin D compounds
US5843928A (en) * 1997-03-17 1998-12-01 Wisconsin Alumni Research Foundation 2-alkylidene-19-nor-vitamin D compounds
EP0983221B1 (en) * 1997-05-23 2002-04-03 Basilea Pharmaceutica AG Cyclohexanediol derivatives
US5936105A (en) * 1997-06-13 1999-08-10 Tetrionics, Inc. 14-EPI-19-nor-vitamin D compounds and methods
US6087350A (en) * 1997-08-29 2000-07-11 University Of Pittsburgh Of The Commonwealth System Of Higher Education Use of pretreatment chemicals to enhance efficacy of cytotoxic agents
AU762481C (en) * 1998-03-27 2004-08-19 Oregon Health Sciences University Vitamin D and its analogs in the treatment of tumors and other hyperproliferative disorders
US6080879A (en) * 1998-05-19 2000-06-27 Tetrionics, Inc. Hexafluoro-vitamin synthesis and crystallization method, solvent and product
US6114317A (en) 1998-05-21 2000-09-05 Wisconsin Alumni Research Foundation Method of locking 1α-OH of vitamin D compounds in axial orientation
US5962707A (en) * 1998-08-18 1999-10-05 Wisconsin Alumni Research Foundation 19-nor-vitamin D3 compounds with calcemic activity
US6603030B1 (en) 1999-04-22 2003-08-05 Hoffman-La Roche Inc. Process for producing phosphineoxide vitamin D precursors
US6310262B1 (en) 1999-10-18 2001-10-30 Basilea Pharmaceutica Ag Process for preparing retiferol derivatives
DE10019861A1 (de) * 2000-04-18 2001-10-31 Schering Ag Neues Synthesezwischenprodukt, seine mikrobiologische Herstellung und Verwendung zur Synthese von Vitamin D-Derivaten
WO2001092221A1 (en) 2000-05-31 2001-12-06 Wisconsin Alumni Research Foundation 2-ethyl and 2-ethylidene-19-nor-vitamin d compounds
JP4811547B2 (ja) * 2000-10-24 2011-11-09 史衛 佐藤 光学活性シクロヘキセン化合物の製造法及びこの製造に用いる光学活性シクロヘキセン誘導体
US6683219B2 (en) * 2001-07-30 2004-01-27 Wisconsin Alumni Research Foundation Synthesis of A-ring synthon of 19-nor-1α,25-dihydroxyvitamin D3 from (D)-glucose
US20040258801A1 (en) * 2001-09-27 2004-12-23 Alvin Ling Vitamin fortification of foodstuffs
US6846811B2 (en) * 2002-04-22 2005-01-25 Wisconsin Alumni Research Foundation (20S) 1α-hydroxy-2α-methyl and 2β-methyl-19-nor-vitamin D3 and their uses
US7023347B2 (en) * 2002-08-02 2006-04-04 Symbol Technologies, Inc. Method and system for forming a die frame and for transferring dies therewith
US20060293291A1 (en) 2003-04-10 2006-12-28 Deluca Hector F 2-Propylidene-19-nor-vitamin d compounds
US20050005434A1 (en) * 2003-06-12 2005-01-13 Matrics, Inc. Method, system, and apparatus for high volume transfer of dies
US6894037B2 (en) 2003-07-03 2005-05-17 Wisconsin Alumni Research Foundation 2-methylene-19-nor-20(S)-25-methyl-1α-hydroxycalciferol and its uses
US7713951B2 (en) 2004-04-09 2010-05-11 Wisconsin Alumni Research Foundation 2-alkylidene-18,19-dinor-vitamin D compounds
WO2006012358A2 (en) * 2004-06-29 2006-02-02 Symbol Technologies, Inc. Systems and methods for testing radio frequency identification tags
US7094775B2 (en) * 2004-06-30 2006-08-22 Bone Care International, Llc Method of treating breast cancer using a combination of vitamin D analogues and other agents
US20060003950A1 (en) * 2004-06-30 2006-01-05 Bone Care International, Inc. Method of treating prostatic diseases using a combination of vitamin D analogues and other agents
US20060225273A1 (en) * 2005-03-29 2006-10-12 Symbol Technologies, Inc. Transferring die(s) from an intermediate surface to a substrate
CN101223135A (zh) * 2005-07-18 2008-07-16 特瓦制药工业有限公司 帕立骨化醇的制备
US20070107186A1 (en) * 2005-11-04 2007-05-17 Symbol Technologies, Inc. Method and system for high volume transfer of dies to substrates
US20070131016A1 (en) * 2005-12-13 2007-06-14 Symbol Technologies, Inc. Transferring die(s) from an intermediate surface to a substrate
US20070139057A1 (en) * 2005-12-15 2007-06-21 Symbol Technologies, Inc. System and method for radio frequency identification tag direct connection test
WO2007105773A1 (ja) 2006-03-15 2007-09-20 Mercian Corporation インデン誘導体の製造方法およびその製造中間体
NZ571896A (en) 2006-04-05 2011-09-30 Wisconsin Alumni Res Found 1-Alpha.-hydroxy-2-(3'-hydroxypropylidene)-19-nor-vitamin D compounds and methods of making and use thereof
US20070244657A1 (en) * 2006-04-11 2007-10-18 Drago Randall A Methods and systems for testing radio frequency identification (RFID) tags having multiple antennas
WO2008053961A1 (fr) 2006-11-02 2008-05-08 Mercian Corporation Procédé et intermédiaire pour la fabrication du dérivé 1-hydroxy-19-norcyclovitamine d
JP5480131B2 (ja) * 2007-05-30 2014-04-23 シトクロマ インコーポレイテッド ホスフィンオキシドビタミンd前駆物質の製造方法
US8377913B2 (en) * 2007-11-20 2013-02-19 Abbvie Inc. Vitamin D receptor activators and methods of making
US20090275768A1 (en) 2008-04-30 2009-11-05 Formosa Laboratories, Inc. Preparation of Paricalcitol
CA2639477C (en) * 2008-09-11 2016-03-22 Alphora Research Inc. Paricalcitol purification
US8013176B2 (en) * 2008-09-11 2011-09-06 Alphora Research Inc. Paricalcitol purification
MX339746B (es) 2009-01-27 2016-06-08 Berg Llc Vitamina d3 y análogos de la misma para aliviar efectos secundarios asociados con la quimioterapia.
JP5978130B2 (ja) 2009-08-14 2016-08-24 バーグ エルエルシー 脱毛症を治療するためのビタミンd3およびその類似体
CN101671288B (zh) * 2009-10-14 2013-10-30 兰州大学 帕立骨化醇的中间体的制备方法
WO2014194133A1 (en) 2013-05-29 2014-12-04 Berg Llc Preventing or mitigating chemotherapy induced alopecia using vitamin d
CN107501317B (zh) * 2017-09-13 2019-08-16 上海皓元医药股份有限公司 一种帕立骨化醇中间体的制备方法

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4607118A (en) * 1981-04-30 1986-08-19 Philip Morris Incorporated Flavor-release β-hydroxy-ester compositions
DE3471928D1 (en) * 1983-01-28 1988-07-14 Hoffmann La Roche Process for the preparation of cholecalciferol derivatives
US4508651A (en) * 1983-03-21 1985-04-02 Hoffmann-La Roche Inc. Synthesis of 1α,25-dihydroxyergocalciferol
DE3476195D1 (en) * 1983-05-18 1989-02-23 Ciba Geigy Ag Cyclohexanedione-carboxylic-acid derivatives having a herbicidal and plant growth regulating activity
US4668817A (en) * 1983-12-21 1987-05-26 International Flavors & Fragrances Inc. Alkyl substituted para-carboalkoxy cyclohexanones
US4681976A (en) * 1983-12-21 1987-07-21 International Flavors & Fragrances Inc. Process for preparing alkyl substituted and unsubstituted para-carboalkoxy cyclohexanones
EP0154185B1 (en) * 1984-02-08 1988-10-05 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Calciferol derivatives
US4613594A (en) * 1984-11-16 1986-09-23 Hoffmann-La Roche Inc. Fluorinated vitamin D3 compounds
US4612308A (en) * 1984-11-29 1986-09-16 Hoffmann-La Roche Inc. 25,26-Dehydro-1α,23(S,R)-dihydroxycholecalciferol and its epimers
ZA859138B (en) * 1984-12-19 1986-08-27 Hoffmann La Roche Cholecalciferol derivatives
US4755329A (en) * 1985-06-10 1988-07-05 Wisconsin Alumni Research Foundation Process and intermediates for preparing 1α-hydroxyvitamin D compounds
AU603340B2 (en) * 1985-08-02 1990-11-15 Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab) Novel vitamin d analogues
IL77668A (en) * 1986-01-21 1989-03-31 Teva Pharma Production of cholecalciferol derivatives and novel intermediates used therefor
ZA8923B (en) * 1988-01-20 1989-09-27 Hoffmann La Roche 16-dehydro-vitamin d3-derivatives
US4804502A (en) * 1988-01-20 1989-02-14 Hoffmann-La Roche Inc. Vitamin D compounds
US4847012A (en) * 1988-04-29 1989-07-11 Wisconsin Alumni Research Foundation Vitamin D related compounds and processes for their preparation
US5232836A (en) * 1988-05-04 1993-08-03 Ire-Medgenix S.A. Vitamin D derivatives: therapeutic applications and applications to assays of metabolites of vitamin D
FR2631025B1 (fr) * 1988-05-04 1991-04-12 Ire Medgenix Sa Nouveaux derives de la vitamine d3 et application aux dosages des metabolites de la vitamine d3
GB8904153D0 (en) * 1989-02-23 1989-04-05 Leo Pharm Prod Ltd Chemical compounds
NZ232734A (en) * 1989-03-09 1991-11-26 Wisconsin Alumni Res Found 19-nor vitamin d derivatives and pharmaceutical compositions
AU650751B2 (en) * 1991-05-28 1994-06-30 Wisconsin Alumni Research Foundation Novel synthesis of 19-nor vitamin D compounds
US5086191A (en) * 1991-05-28 1992-02-04 Wisconsin Alumni Research Foundation Intermediates for the synthesis of 19-nor vitamin D compounds

Also Published As

Publication number Publication date
JP2648845B2 (ja) 1997-09-03
US5391755A (en) 1995-02-21
KR920021505A (ko) 1992-12-18
JPH11240891A (ja) 1999-09-07
IE921700A1 (en) 1992-12-02
JPH09118641A (ja) 1997-05-06
EP0516410A2 (en) 1992-12-02
CA2191993C (en) 2002-07-09
JPH05221960A (ja) 1993-08-31
US5616759A (en) 1997-04-01
ES2118794T3 (es) 1998-10-01
US5563286A (en) 1996-10-08
KR0160937B1 (ko) 1999-01-15
AU659774B2 (en) 1995-05-25
CA2069374C (en) 1999-08-31
JP3320025B2 (ja) 2002-09-03
DE69226402D1 (de) 1998-09-03
JP3494637B2 (ja) 2004-02-09
AU650751B2 (en) 1994-06-30
AU5932594A (en) 1994-06-02
AU1712092A (en) 1992-12-03
US5581006A (en) 1996-12-03
KR0160784B1 (ko) 1999-01-15
US5486636A (en) 1996-01-23
DE69226402T2 (de) 1998-12-10
CA2069374A1 (en) 1992-11-29
US5281731A (en) 1994-01-25
US5597932A (en) 1997-01-28
EP0516410A3 (en) 1993-06-30
CA2191993A1 (en) 1992-11-29
EP0516410B1 (en) 1998-07-29
ATE168996T1 (de) 1998-08-15
JP2926008B2 (ja) 1999-07-28
JP2002201197A (ja) 2002-07-16
KR0160936B1 (ko) 1999-01-15

Similar Documents

Publication Publication Date Title
DK0516410T3 (da) Hidtil ukendt syntese af 19-nor-vitamin D-forbindelser
AU4726685A (en) Internal mold release compositions, active hydrogen- containing compositions containing the internal mold release compositions & process for preparing molded polyurethane and
NO874329D0 (no) Hylser for "sommerfugl"-naaler.
DK188590A (da) Forbedring af reproduktionsevne
GR3029334T3 (en) Novel use of 1alpha-hydroxylated-19-nor-vitamin D compounds to treat psoriasis
DE68919653D1 (de) Organopolysiloxanzusammensetzung zur Herstellung einer gehärteten Trennfolie.
ES2085898T3 (es) Tratamiento de la enfermedad hepatobiliar con compuestos 15-cetoprostaglandina.
EP0126651A3 (en) 2,4-dihydro-5-((substituted)phenyl)-4,4-disubstituted-3h-pyrazol-3-ones, 2,4-dihydro-5-((substituted)phenyl)-4, 4-disubstituted-3h-pyrazol-3-thiones, and a process for producing the same
DE3781653D1 (de) Verwendung von cembrane-diterpene verbindungen zur herstellung von zusammensetzungen, die inhibitoren der freigabe von lysosomen enthalten.
DE3061398D1 (en) Substituted alkylammonium salts, their preparation and use in plant growth regulation
IT8109380A0 (it) Procedimento ed attrezzatura per la realizzazione di calzature aperte con fondo stampato in resina, e calzature cosi' realizzate
JPS51124197A (en) A resin composition
ATE117693T1 (de) P-substituierte propanphosphinsäureverbindungen.
DE3683158D1 (de) Faerbende zusammensetzung.
DK96379A (da) Fremgangsmaade til fremstilling af disubstituerede 2,3-dihydroimidazo (1,2-c)-pyrimidiner
JPS52145528A (en) Preparation of gel composition for nail enamel
JPS559465A (en) Light polymerizable resin composition for hybrid ic coating
DE69128763D1 (de) Zusammensetzung, die Polyetherverbindungen enthält, Prozess zu ihrer Herstellung sowie Licht härtbare Harzzusammensetzungen
IT8420577A1 (it) "procedimento per la fabbricazione di suole di scarpe stampo per l'esecuzione di questo procedimento"
ATE32063T1 (de) Iminosulfonamide und verfahren zu ihrer herstellung, die pharmazeutische praeparate solche verbindungen enthalten, sowie die verbindungen zur verwendung.
JPS5325655A (en) Composition used for the formation of film
IT7922201A0 (it) Procedimento per la fabbricazione di stampi per suole di calzature e stampi cosi' ottenuti.
JPS5340746A (en) Organophosphorous compound and chlorine-containing resin composition
DK391482A (da) Fremgangsmaade til fremstilling af ren 6,6-diiodpenicillansyre ved diazotering af 6beta-aminopenicillansyre i naervaer af iod
JPS5432071A (en) Manufacture of semiconductor element