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PT81118B - Process for preparing novel antibiotics and pharmaceutical compositions therefrom - Google Patents

Process for preparing novel antibiotics and pharmaceutical compositions therefrom Download PDF

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Publication number
PT81118B
PT81118B PT81118A PT8111885A PT81118B PT 81118 B PT81118 B PT 81118B PT 81118 A PT81118 A PT 81118A PT 8111885 A PT8111885 A PT 8111885A PT 81118 B PT81118 B PT 81118B
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PT
Portugal
Prior art keywords
pharmaceutically acceptable
called
pharmaceutical compositions
compound
formula
Prior art date
Application number
PT81118A
Other languages
English (en)
Other versions
PT81118A (en
Inventor
Anne Camille Horan
Jerzy Golik
James Andrew Matson
Mahesh Gordhandas Patel
Original Assignee
Schering Corp
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 Schering Corp filed Critical Schering Corp
Publication of PT81118A publication Critical patent/PT81118A/pt
Publication of PT81118B publication Critical patent/PT81118B/pt

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P1/00—Preparation of compounds or compositions, not provided for in groups C12P3/00 - C12P39/00, by using microorganisms or enzymes
    • C12P1/02—Preparation of compounds or compositions, not provided for in groups C12P3/00 - C12P39/00, by using microorganisms or enzymes by using fungi
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/26—Preparation of nitrogen-containing carbohydrates
    • C12P19/28—N-glycosides
    • C12P19/38—Nucleosides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/044—Pyrrole radicals
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/44—Preparation of O-glycosides, e.g. glucosides
    • C12P19/58—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical directly bound through only acyclic carbon atoms to a non-saccharide heterocyclic ring, e.g. bleomycin, phleomycin

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Microbiology (AREA)
  • General Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Mycology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Saccharide Compounds (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Compounds Of Unknown Constitution (AREA)

Description

Descrição: Sólido amorfo amarelo de cristais
I de agulha finos
Fórmula Molecular:
C34H35C1N4°9
Peso Molecular: 679,17 Determinado por Espectrometria de Massa de Ionização Quimica, utilizando CH4 como gâs reagente. /"IQ-em-ch4_7
Espectro Ultravioleta: Xmax(c, 0,2290 g/L CHgOH);
Máximos eabsorvâncias observados (entre parêntesis) = 200 nm(45,5)
235 mn (58,9), 283 nm (50,6), 316 nm (67,2), 395 nm (5,7).
Espectro Infravermelho: λ max (KBr); 3425, 3362, 2940, 1750
1696, 1581, 1475, 1462, 1442, 1382, 1335, 1277, 1242, 1194, 1128, 1078, 1052, 768, 759 cm-1.
RMN 360 ΜΗζ Espectro de Ressonância Magnética Nuclear: Deslocamentos Químicos Observados e Descrição Padrão (dimetil sulfóxido-dg):
10.64 (s, IH, N5’-H), 9.27 (d, IH, Cl-H «OU ΟΡΗ), 9^18 (d, IH, Cl'-H OU Cl-H), 7.88 (d, IH, C4’-H),
7.73 (m, 2H, C3-H and C3'-H), 7.49 (m, 2H, C2-H e C2'H), 6-91, (d, IH, C1H-H), 5^48 (sl, IH, C3"-OH), 5;13 (m, IH, Cl"'-H), .5^06 (sl, IH, C2"-OH), 4,81 (sl, IH, C3"'-OH), 4^21 (dl, IH, C6a"-H), 4;08 (dl, IH, C5"-H), 3.99 (dd, IH, C6b"-H), 3.77 idd, lH, C3"’-H), 3*60-3,70
i i I ,
(rn, 6H, C2"-H, C3"-H, C4"-H, 3H,C4-H"-OCH3), 3.40 (m, lH, 3.25 (s, 3H, Νβ-ςΐ^), 2.,30 (m (s, 3H, C4---NÇH3), 1?78 (m,
C5a-'-H.C5b*’-H), 3/68 (s,
~H .sobrepõe-se com* 1 ·
, 2H, C4"’-NH, C2"'—H), 2.22 IH, C2b"’-H). Z
I
i
13
C RMN 90 MHz Espectro de Ressonância Magnética Nuclear
Variações Quimicas Observadas e Denominações £ *’ c Denominação
(dimetil sulfóxido-dg): PPM
PPM Denominação
169,0 C7 117,6 C5b
169,0 C7* 116,4 C4
140,2 C4a. 112,1 C4'
'138,1 C4a' 99,0 Cl" '
130,0 C5a 84,7 Cl"
129,7 C3’ 78,8 C3"
129,5 C5a' 78.1 C4"
127,8 C3 77,5 C5" ·
125,3 C5c 72,2 C2"
124,6 Cl' 66,5 C3"'
123,4 Cl 66,0 C6"
122,4 G2 61,8 C5" '
121,4 C5c' 61,7 C4" '
121,3 C6 60,1 C4"-OÇH3
121,0 C2' 37,0 C2" '
119,2 C6' 33,9 C4"'-NCH3
118,4 C5b’ ’ 23,6 N8-CH3
Espectro de Massa (IQ FM-CH^): M/Z=679/“M+l7+
QUADRO VIII
AT 2433A,: Composto de fórmula I em
que X ê Cl e R ê H.
Descrição: sólido amorfo amarelo
Fórmula Molecular: CggH^ClN^Og
Peso Molecular: 665,10 Espectrometria de Massa de Alta
' e Baixa Resolução de Desadsorção de Campo.
Espectro Ultravioleta: X max (c, 0,0158 g/L CHgOH);
máximo e adsorvências observadas (entre parêntesis) = 298 nm (45,9) 233,5 mn 58,2), 286 nm (50,6),
314 nm (66,1), 394 nm (5,2).
Espectro Infravermelho: Â max (KBr); 3420, 3355, 2930,
1745, 1691, 1575, 1472, 1458,
1438, 1380, 1330, 1278, 1240, 1140 1120, 1080, 1045, 765, 755 cm"* 1.
RMN 360 MHz Espectro de Ressonância Magnética Nuclear:
í Deslocamentos Químicos Observados e Descrição Padrão (4f H
I (dimetil sulfóxido-dg
10/64 (s, ÍH, N5'-H), 9/27 (d, ÍH, Cl-H ou C1‘j H), 9.18 (d, ÍH, C1'-HOU Cl-H), 7,.88 (d, lH, C4'-H),
I 7,33 (m, 2H, C3-H e C3'-H), 7,49 (m, 2H, C2-H θ' C2'H), 6,91, (d, ÍH, Cl"-H), 5.48 (sl, ÍH,
C3“-OH),, 5.14 (m, 1H, Cl'“’-Η), .5,06 (sl, lH, C2“-OH_),
4.81 (sl>r ÍH, C3"*-OH) 4^21 (dl, ÍH, C6a"-H), 4,.08
i (dl, ÍH, C5"-H), 3,.99 (dd, ÍH, C6b"-H), 3,68 (S, 3H,C4"OCH3)» 3^72-3^30 (m, 7H, C2"-H, C3"-H, C4"-tf, C3'"-H,
C4"'-H, C5a" 1-H,C5b"'-H sobrepõe-se com J^O), 3?25 (s, 3H, N8-CH3), 2/55 (m, 2H, C4"'-NH2), 2^32 (m, ÍH, C2a"’-H),
1,73 (m, ÍH, C2b"’-H).
Espectros de Massa: Medidas de Alta e Baixa Resolução de Desadsorção de campo:
DC-BR-EM: m/z 664 í~_ M7+
m/z 687 /~M+Na7+
DC-AR-EM: m/z 664,1795 observado
664, 1936 esperado para C33H33C1N4°9
EXEMPLO 4
Resolução de AT 2433 Bj e B2:
Numa coluna Glenco com 2,65 cm (d.i.) x 60 cm introduziu-se gel de silica Baker C-18 (0,040 mm de dimensão média de partículas/ empastada em metanol. A coluna foi inserida no sistema de CLa média pressão e equilibrada com 600 ml do eluente seguinte: 3 partes de acetonitrilo, 3 partes de acetonitrilo, 3 partes de metanol e 4 partes de acetato de amónio 0,1 M. Colocou-se uma amostra de 360 mg de AT 2433 B obtida do Exemplo 2D em 2 ml de dimetilsulfóxido no laço de amostra e bombeou-se sobre a coluna com eluente. A eluição iniciou-se observando o eluente a 405 nm e 435 nm com o detector uv ISCO e colhendo fracções de 50 ml. Experimentaram-se partes (5 yjl) das fracções 14 a 19 por meio de clap utilizando uma coluna yu-Bondapak C-18 e um eluente de 4 partes de acetonitrilo, 3 partes de metanol e 3 partes de acetato de amónio 0,1 M. As fracções 14 a 16 foram reunidas e extraídas com 500 ml de clorofórmio. A fase inferior (clorofórmio) foi separada a concentrada atê secagem para dar AT 2433 B2. As fracções 17 a 24 foram reu-
-53-
nidas e extraídas com 500 ml de clorofórmio. A fase inferior (clorofórmio) foi separada e concentrada até secagem para dar AT 2433 B^ impuro. 0 AT 2433 B^ impuro foi recromatografado e isolado exactamente conforme descrito acima para dar aproximadamente 180 mg de AT 2433 B^ puro.
As propriedades físicas e químicas de AT 2433 Bj e B2 estão indicadas nos Quadros IX e X respectivamente
QUADRO IX
..AT 2433 Bp Composto de fórmula I
em que X ê H e R ê CHg.
Descrição: Sólido amorfo amarelo
Fórmula:Molecular: C34H36N4°9
Peso Molecular: 644,68 Determinado.por Espectrometria
de Massa de Alta e Baixa Resolução de Desadsorção de Campo e por IQ-EM-CH^.
Espectro Ultravioleta: λ max (c,0,0222 g/L CHgOH); Máximos Observados e adsorvências (entre parêntesis) = 202 nm (45,0), 234 mn (64,1), 284 nm (52,2), 316 nm (72,9 ), 400 nm (6,3).
Espectro Infravermelho: /max (KBr); 3363, 2940, 1750, 1692, 1575, 1475, 1460, 1435, 1380, 1332, 1240, 1185, 1105, 1010, 750 cm"1.
22¾ .
1
H RMN 360 MHz Espectro de Ressonância Magnética Nuclear
•SS;
WSM· MURMoç^
Deslocamentos Quimicos Observados e Descrição Padrão J H
(dimetil sulfóxido-dg)
10/50 (dl, 1H, N5'-H), 9,32 (d, 1H, Cl-H ou 9.21 (d, 1H, Cl'-H ou Cl-H), 8,14 (d, 1H, C4-H),
7/86 (d, 1H, C4'-H), 7,.68 (m, 2H, Ç3-H e C3'-H), 7,48 <m, ,2H, G2-H e C2'-H), 6/44, (d? ΙΗ, Cl^H), 5,6-4.6 (ml, m · 4H, C3"-OH, Çl"»-H, C2"-OH, C3"-QH), 4,3-3.2 (m, JLOH, C2"-H, C3"-H, C4*-H, C5"-H, C6a"-H, C6b"-H, C3H’-H, C4*'-H, C5a"'-H, C5b"’-H), 3,68 (s, 3H, 04--00^), 3.25 (s, 3H, N8—ÇH_2), 2Z35 (m, 1H, C4'”-NH_), 2/30<s,3H,C4" 1-NCH3), 2.03 (nt, 1H, C2a"'-H), 1.60 (m, iH, C2b**-H). - · '
1 3
C RMN 90 MHz Espectro de Ressonância Magnética Nuclear: 9 (dimetil sulfóxido-dg)
Deslocamentos Quimicos Observados (PPM):
169,6, 169,5, 140,5, 139/5, 127,4, 127,2, 127..0, 126.7, 124.5, 124.3, 124.2, 120.9, 120.3, 114.7, 111.7, 97.8, 86.5, 79.1, 76.2, 76,0, 71,1, 66.3, 65.7, 61.9, 60.3, 60.0, 38.0, 23.6.
Ionização Quimica-CH^: m/z=645,/~M+í7+
Medidas de Alta e Baixa Resolução
de desadsorção de campo
m/z=644, /“M7+
m/z=667, /"M+Na7+
m/z=644,2401 observado,
644,2476 espectro para £34^35^4.09
Espectros de massa
Br-EM:
BR-EM:
QUADRO X
AT 2433B2: Compsto de fórmula I
em que X ê H e R ê H.
Descrição: Sólido amorfo amarelo
Fórmula Molecular.
33H34N4°9
Peso Molecular.
630,65 Determinado por Espectrometria de Massa de Alta Resolução e de Baixo Campo de Desadsorção
Espectro Ultravioleta: max (c, 0,0184 g/L CHgOH);
Máximos observados e absorvências (entre parêntesis) = 201 nm (48,9) 233 mn (65,2), 282 nm (53,0), 315 nm (74,5), 400 nm(6,3).
Espectro de Infravermelho
Ãmax(KBr_); 3500sh, 3365, 2940,
1750, 1692, 1578, 1478, 1462,
1437, 1381, 1332, 1277, 1241,
1115, 1085, 1055, 1012, 995, 750
-1 cm .
RMN 360 MHz Espectro de Ressonância Magnética Nuclear:
Deslocamentos Químicos Observados (PPM) e Descrição padrão
^(dimetil sulfóxido-dg):'
10f50 . (sl, ÍH, N5'-H>, 9,32 (d, ÍH, Cl-H ou Cl'-H), 9,21 (d, ÍH, Cl’-H ou Cl-H), 8,14 (d, lH, C4-H), 7^,86 (d, ÍH, C4’-H), 7,68 (m, 2H, C3-H s C3'-H), 7.48 (m, 2H, C2-H e*C2'-H), 6.44 (d, ÍH, Cl'-H), 5,.6-4..6 (ml, C3"-ÓH, Cl"'-H, C2--OH, C3"-OH), 4,3-3,2 (m, 10H, C2"-H, C3"-H, C4"-H, C5"-H, C6a"-H, C6b"-H, C3"'-H, C4'"H, (Z5a"'-H'/ C5b"'-H), 3,68 (s, 3H,C4"-OCH3), 3,25 (.S,
3H, Ne-CHg), 2,55 (m,2H,C41''-NH^), 2.03 (m, lH, C2a"'H), 1.60 (m, ÍH, C2b"'-H).
Espectro de Massa: Pedidos de Alta e Baixa Resolução de Desadsorção do Campo:
BR-EM. m/z=630 /"M7+
m/z=653 /“M+Na7+ m/z=630,2224 observado 630,2316 Esperado por
AR-EM

Claims (3)

  1. REIVINDICAÇÕES
    lâ. - Processo para a preparação de
    um composto que a fórmula
    no qual X é H ou Cl e R ê H ou CH^, em forma racêmica ou ópticamente activa, e dos seus sais farmaceuticamente aceitáveis, caracterizado pelo facto de compreender a cultura de uma estirpe de Actinomadura mel 1iaura capaz de produzir esse(s) composto(s) num meio nutriente aquoso até lhe ser conferida actividade antibaeteriana substancial, e o isolamento de pelo menos um dos compostos como tal ou na forma de um sal farmaceutiacmente aceitável.
    -582â. - Processo de acordo com a reivindicação 1, caracterizado pelo facto de ser cultivado Actinomadura mel 1iaura ATCC 39691 ou um seu mutante.
  2. 3â. - Processo de acordo com as
    reivindicações 1 ou 2, caracterizado pelo facto de ser preparado um composto de fórmula I no qual (a) X ê Cl e R ê CHg denominado AT 2433 Ap ou (b) X ê Cl e R é H, denominado AT 2433 A2, ou (c) X ê H e R ê CHg, denominado AT 2433 Rp ou (d) X ê H e R é H, denominado AT 2433 B2, ou (e) complexo
    AT 2433 que compreende os quatro compostos (a) e (d) ou (f)
    uma mistura que compreende AT 2433 Aj e AT 2433 A2 ou (g)
    uma mistura que compreende AT 2433 Bj e AT 2433 B2 e os seus
    sais farmaceuticamente aceitáveis.
  3. 4ã. - Processo para a preparação de
    composições farmacêuticas, caracterizado pelo facto de pelo menos um dos compostos definidos em qualquer das reivindicações 1 a 3 ser misturado com um veiculo ou excipiente farmaceuticamente aceitável.
PT81118A 1984-09-17 1985-09-12 Process for preparing novel antibiotics and pharmaceutical compositions therefrom PT81118B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US06/651,498 US4743594A (en) 1984-09-17 1984-09-17 Antibiotic, antitumor compounds and their use

Publications (2)

Publication Number Publication Date
PT81118A PT81118A (en) 1985-10-01
PT81118B true PT81118B (en) 1987-07-06

Family

ID=24613073

Family Applications (1)

Application Number Title Priority Date Filing Date
PT81118A PT81118B (en) 1984-09-17 1985-09-12 Process for preparing novel antibiotics and pharmaceutical compositions therefrom

Country Status (18)

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US (1) US4743594A (pt)
EP (1) EP0175284B1 (pt)
JP (1) JPS61106592A (pt)
KR (1) KR860002574A (pt)
AT (1) ATE42305T1 (pt)
AU (1) AU4741785A (pt)
CA (1) CA1315230C (pt)
DE (1) DE3569538D1 (pt)
DK (1) DK415185A (pt)
ES (1) ES8703931A1 (pt)
FI (1) FI853506L (pt)
GR (1) GR852224B (pt)
HK (1) HK4992A (pt)
HU (1) HU194315B (pt)
NO (1) NO853567L (pt)
PT (1) PT81118B (pt)
YU (1) YU147385A (pt)
ZA (1) ZA857003B (pt)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3835842A1 (de) * 1988-10-21 1990-04-26 Goedecke Ag Indolocarbazol-derivate, verfahren zu deren herstellung und deren verwendung als arzneimittel
US5015578A (en) * 1989-03-23 1991-05-14 Bristol-Myers Squibb Company BMY-41950 antitumor antibiotic
JPH07504674A (ja) * 1992-03-20 1995-05-25 ザ・ウエルカム・ファウンデーション・リミテッド 抗ウイルス活性を有する更なるインドール誘導体

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5918035A (ja) * 1982-07-20 1984-01-30 Katsuyuki Taniguchi ダンプ車の荷箱の支点構造
US4487925A (en) * 1983-01-28 1984-12-11 Bristol-Myers Company Rebeccamycin and process for its preparation
US4524145A (en) * 1984-09-04 1985-06-18 Bristol-Myers Company 4'-Deschlororebeccamycin pharmaceutical composition and method of use

Also Published As

Publication number Publication date
NO853567L (no) 1986-03-18
DK415185D0 (da) 1985-09-12
ES8703931A1 (es) 1987-03-01
JPH0558440B2 (pt) 1993-08-26
ES546915A0 (es) 1987-03-01
FI853506A0 (fi) 1985-09-13
YU147385A (en) 1988-06-30
KR860002574A (ko) 1986-04-26
FI853506L (fi) 1986-03-18
AU4741785A (en) 1986-04-24
PT81118A (en) 1985-10-01
GR852224B (pt) 1986-01-13
DE3569538D1 (en) 1989-05-24
ZA857003B (en) 1986-12-30
DK415185A (da) 1986-03-18
EP0175284B1 (en) 1989-04-19
EP0175284A3 (en) 1986-12-17
JPS61106592A (ja) 1986-05-24
HK4992A (en) 1992-01-17
CA1315230C (en) 1993-03-30
HUT42527A (en) 1987-07-28
EP0175284A2 (en) 1986-03-26
ATE42305T1 (de) 1989-05-15
HU194315B (en) 1988-01-28
US4743594A (en) 1988-05-10

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