EP0524974A1 - Pyridines utiles comme medicaments - Google Patents

Pyridines utiles comme medicaments

Info

Publication number
EP0524974A1
EP0524974A1 EP91907002A EP91907002A EP0524974A1 EP 0524974 A1 EP0524974 A1 EP 0524974A1 EP 91907002 A EP91907002 A EP 91907002A EP 91907002 A EP91907002 A EP 91907002A EP 0524974 A1 EP0524974 A1 EP 0524974A1
Authority
EP
European Patent Office
Prior art keywords
compounds
alkyl
formula
salts
grouping
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.)
Withdrawn
Application number
EP91907002A
Other languages
German (de)
English (en)
Inventor
Peter Zimmermann
Wolf-Rüdiger Ulrich
Kurt Klemm
Karl Sanders
Rainer Boer
Hildegard Boss
Klaus-Dieter Beller
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.)
Takeda GmbH
Original Assignee
Byk Gulden Lomberg Chemische Fabrik GmbH
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 Byk Gulden Lomberg Chemische Fabrik GmbH filed Critical Byk Gulden Lomberg Chemische Fabrik GmbH
Publication of EP0524974A1 publication Critical patent/EP0524974A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Definitions

  • the invention relates to new pyridines, processes for their preparation, their use and medicaments containing them.
  • the compounds according to the invention are used in the pharmaceutical industry for the production of medicaments.
  • the invention relates to new pyridines of the formula I.
  • R2 is hydrogen, 1-6C-alkyl or together with R3 2-3C-alkylene,
  • R3 is 1-4C-alkyl, 1-4C-alkoxy, 3-5C-alkoxyalkyl, 3-5C-alkoxyalkoxy or together with R22-3C-alkylene,
  • R4 denotes phenyl substituted by R41 and R42
  • ERS R41 is hydrogen, hydroxy, halogen, nitro, cyano, trifluoromethyl, 1-4C-alkyl, 1-4C-alkoxy, completely or partially substituted by fluorine-1-4C-alkoxy, 1-4C-alkoxycarbonyl, 2-5C-acyl, amino or mono- or di-1-4C-alkylamino,
  • R42 is hydrogen, hydroxy, halogen, nitro, cyano, trifluoromethyl, 1-4C-alkyl, 1-4C-alkoxy, completely or partially substituted by fluorine-1-4C-alkoxy, 1-4C-alkoxycarbonyl, 2-5C-acyl, amino or mono- or di-1-4C-alkylamino,
  • AI means a bond line or 2-4C-alkylene
  • A2 is 2-4C-alkylene or 2C-alkyleneoxy-2C-al ylene
  • R6a and R6b together and including the nitrogen atom to which both are attached form a radical of the formula
  • R7 is hydrogen (H) or aryl and R8 is aryl, or R7 and R8 together are di arylmethyls, R9 is di aryl-1-4C-alkyl and RIO Aryl-1-4C-alkyl means, where aryl for a ring of the formula
  • R11 and R12 are the same or different and have the meaning hydrogen (H), 1-4C-alkyl, 1-4C-alkoxy, halogen, hydroxy, trifluoromethyl or together methylenedioxy, and the salts of these compounds.
  • 1-6C-A1 yl is straight-chain or branched and means, for example, a hexyl, neopentyl, isopentyl, butyl, i-butyl, sec-butyl, t-butyl, propyl, isopropyl or in particular ethyl or methyl radical.
  • 2-3C-Alkylene is ethylene or propylene, so that R2 and R3, if they together have this meaning, together with the carbonyl group form a 5- or 6-ring fused to the dihydropyridine ring.
  • 1-4C-A1kyl is straight-chain or branched and means, for example, a butyl, i-butyl, sec-butyl, t-butyl, propyl, isopropyl, ethyl or in particular methyl radical.
  • 1-4C-alkoxy contains one of the 1-4C-alkyl radicals mentioned above.
  • Preferred. 1-4C-Alkoxy radicals R41, R42, R11 and R12 are the methoxy and the ethoxy radical.
  • Preferred 1-4C-alkoxy radicals R3 are the isopropoxy and the t-butoxy radical.
  • 3-5C-alkoxyalkyl stands for example for a methoxyethyl, ethoxyethyl, propoxyethyl or ethoxymethyl radical.
  • 3-5C-alkoxyalkoxy stands for example for a methoxyethoxy, ethoxyethoxy or propoxyethoxy radical.
  • Halogen in the sense of the invention means bromine, fluorine and especially chlorine.
  • 1-4C-Alkoxy which is wholly or partly substituted by fluorine is, for example, 1,1,2,2-tetrafluoroethoxy, trfluoromethoxy, 2,2,2-trifluoroethoxy or in particular difluoromethoxy.
  • 1-4C-alkoxycarbonyl contains one of the 1-4C-alkoxy radicals mentioned above.
  • 2-5C-acyl contains one of the 1-4C-alkyl radicals mentioned above.
  • the acetyl radical is preferred.
  • mono- or di-1-4C-alkylamino contains one or two of the 1-4C-alkyl esters mentioned above.
  • Di-1-4C-alkylamino is preferred, and in particular dimethyl-, diethyl- or diisopropylamino.
  • Straight-chain or branched 1-7C-alkylene is, for example, methylene (-CH 2 -), ethylene (-CH 2 -CH 2 -), trimethylene (-CH 2 -CH 2 -CH 2 -), tetramethylene (-CH 2 -CH 2 -CH 2 -CH 2 -), 1,2-dimethylethylene [-CH (CH 3 ) -CH (CH 3 ) -], 1,1-dimethylethylene [-C (CH 3 ) 2 -CH 2 - ], 1,1-dimethylpropylene [-C (CH 3 ) 2 -CH 2 -CH 2 -], 2,2-dimethylethylene [-CH 2 -C (CH 3 ) 2 -], isopropylidene [-C ( CH 3 ) 2 -], 1-methylethylene [-CH (CH 3 ) CH 2 -], pentamethylene (-CH 2 -CH 2 -CH 2 -CH 2 -) and hexamethylene (-CHCHCH 2
  • 2-4C-alkylene stands for ethylene (-CH 2 -CH 2 -), trimethylene (-CH 2 -CH 2 -CH 2 -) and tetramethylene (-CH 2 -CH 2 -CH 2 -CH 2 -), with ethylene being preferred.
  • 2C-Alkyleneoxy-2C-alkylene stands for ethylene which is substituted by ethyleneoxy (-CH 2 -CH 2 -0-CH 2 -CH 2 -).
  • Aryl stands for R11 and R12 substituted phenyl.
  • aryl radicals which may be mentioned are: phenyl, 4-methoxyphenyl, 4-chlorophenyl, 4-methylphenyl, 4-fluorophenyl, 3-fluorophenyl, 3-chlorophenyl, 2-chlorophenyl, 3-methoxyphenyl, 2-methoxyphenyl, 2-ethoxyphenyl, 2-methylphenyl, 3-chloro-4-methylphenyl, 3,4-dichlorophenyl, 3,6-dichlorophenyl, 2,4-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3 , 4-methylenedioxyphenyl, 2-trifluoromethylphenyl and 3-trifluoromethylphenyl.
  • Diaryl-1-4C-alkyl is 1-4C-alkyl which is substituted by two aryl radicals. Diaryl-1-4C-alkyl is especially diphenylmethyl (benzhydryl), or substituted benzhydryl, e.g. 4,4'-difluorobenzhydryl, 4,4'-dimethylbenzhydryl, 4,4'-dimethoxybenzhydryl or 4,4'Dichlorbenzhydryl.
  • Aryl-1-4C-alkyl represents 1-4C-alkyl which is substituted by aryl.
  • aryl-1-4C-alkyl radicals which may be mentioned are: 4-methylbenzyl, 4-methoxybenzyl, 4-chlorobenzyl, 1-phenethyl, 2-phenylethyl, 3-phenylpropyl, 3-chlorobenzyl, 2,5-dimethylbenzyl , 4-fluorobenzyl, 3-methylbenzyl and in particular benzyl.
  • Suitable as such are, for example, water-soluble and water-insoluble acid addition salts, such as the hydrochloride, hydrobromide, hydroiodide, phosphate, nitrate, sulfate, acetate, citrate, gluconate, benzoate, hibenzate, fendizoate, butyrate, sulfosalicylate, maleate, laurate, malate , Fuma rat, succinate, oxalate, tartrate, amsonate, metembonate, stearate, tosilate, 2-hydroxy-3-naphthoate, 3-hydroxy-2-naphthoate or mesilate.
  • water-soluble and water-insoluble acid addition salts such as the hydrochloride, hydrobromide, hydroiodide, phosphate, nitrate, sulfate, acetate, citrate, gluconate, benzoate, hibenzate, fendizoate, butyrate, sul
  • One embodiment (embodiment a) of the invention is compounds of the formula Ia
  • Rl 1-6C-A1 means kyl and R2, R3, R4, El, E2, R6a and R6b the above
  • a further embodiment (embodiment b) of the invention are compounds of the formula Ib
  • Rl 1-6C-A1kyl means and R2, R3, R4, El, E2, R6a and R6b have the meanings given above, and the salts of these compounds.
  • REPLACEMENT LEAF Compounds to be emphasized are those of the formula I in which one of the radicals Rl and R5 denotes 1-6C-alkyl and the other the grouping -El-E2-N (R6a) R6b, R2 1-4C-alkyl or together with R3 2- 3C-alkylene means R3 1-4C-A1kyl, branched-chain 3-4C-alkoxy or together with R2 means 2-3C-A1kylene, R4 means phenyl substituted by R41 and R42, R41 means hydrogen, chlorine or nitro, R42 means hydrogen or means chlorine, El means methylene (CH 2 ), E2 means ethylene, propylene, tetramethylene, pentamethylene, hexamethylene or the
  • AI means a bond line
  • A2 means ethylene
  • R7 is hydrogen or phenyl and R8 is phenyl, or R7 and R8 together are diphenylmethylene, R9 is diphenylmethyl (benzhydryl) and RIO is benzyl or 4-chlorobenzyl, and the salts of these compounds .
  • REPLACEMENT LEAF Preferred compounds of the formula I are those in which one of the radicals R1 and R5 denotes 1-4C-A1kyl and the other denotes the group -El-E2-N (R6a) R6b, R2 1-4C-A1kyl or together with R32-3C Alkylene means R3 1-4C-alkyl, branched chain 3-4C-alkoxy or together with R22-3C-alkylene, R4 means 3-nitrophenyl or 2,3-dichlorophenyl, El means methylene, E2 propylene, tetramethylene, Pentamethylene, hexamethylene or the grouping
  • AI means a bond line
  • A2 means ethylene
  • R7 is -CH 2 -CH 2 -C (R7) R8-CH 2 -CH 2 -, R7 is phenyl and R8 is phenyl, or R7 and R8 together are diphenylmethylene, and the salts of these compounds.
  • Preferred compounds of the embodiments a and b are those of the formulas Ia and Ib, in which Rl is 1-4C-A1kyl and R2, R3, R4, El, E2, AI, A2, R6a, R6b, A, R7 and R8 are those for the preferred compounds have the meanings given.
  • the invention further relates to a process for the preparation of the compounds of the formula I and their salts.
  • the process is characterized in that compounds of the formula II
  • R 1, R 2, R 3, R 4 and R 5 have the meanings given above.
  • the oxidation is carried out in a manner familiar per se to the person skilled in the art in inert solvents, such as, for example, dichloromethane, at temperatures between 0 ° C. and 200 ° C., preferably between 0 ° C. and 50 ° C.
  • inert solvents such as, for example, dichloromethane
  • inorganic and organic oxidizing agents such as, for example, manganese dioxide, nitric acid, chromium (VI) oxide or alkali dichroate, nitrogen oxides, chloranil, tetracyanobenzoquinone or anodic oxidation in the presence of a suitable electrolyte system are suitable.
  • the dihydropyridines of the formula II are new and likewise the subject of the invention. You can e.g. in analogy to the processes described in the patent applications EP-A-176956 EP-A-138505, EP-A-242829, EP-A-314038 or DE-OS 3627742, but preferably according to the following reaction scheme,
  • Rl is 1-6C-A1kyl
  • X is a leaving group (preferably a halogen atom, especially bromine or chlorine)
  • R2, R3, R4, El, E2, R6a and R6b have the meanings given above.
  • REPLACEMENT LEAF 9 3-Acetyl-5-tert-butoxycarbonyl-2- [2- (4,4-diphenyl-l-piperidinyl) -1-ethyloxy] methyl-6-methyl-4- (3-nitrophenyl) pyridine
  • REPLACEMENT LEAF concentrated and chromatographed the residue on silica gel with toluene / acetone 2/8.
  • the product thus obtained is taken up in 120 ml of isopropanol and diluted with 150 ml of diethyl ether.
  • the title compound is precipitated by adding ethereal hydrochloric acid. Yield: 4.6 g (52%). M.p .: 225-227 C (acetone tril).
  • the compounds of the formula I and their salts have valuable properties which make them commercially usable. They are primarily antineoplastic agents with interesting cytostatic activity. They can be used in the treatment of tumor diseases, for example to reduce or prevent the formation of metastases and tumor growth in mammals. They can not only be used in combination with other cytostatics to overcome the so-called 'drug resistance' or 'multidrug resistance'. Rather, due to their antineoplastic properties, they are per se suitable for the treatment of tumors that are considered resistant to therapy.
  • compounds of the formula I and their salts differ in surprising and advantageously from known cancer chemotherapy drugs. Although the compounds of the formula I and their salts have only a slight calcium channel-blocking effect, they have the pronounced ability to inhibit the growth of tumor cells in vitro, from which a corresponding in vivo effect can be concluded.
  • the low calcium channel blocking activity of compounds of formula I comes from the comparatively small influence of these compounds on the cardiovascular system, e.g. on blood pressure and heart rate, expressed.
  • This weak cardiovascular activity of compounds of the formula I and their salts permits their use in human medicine as potent agents for inhibiting tumor growth and preventing metastasis, since they are administered in therapeutically effective doses to the cardiovascular system without the risk of undesirable side effects can.
  • chemotherapeutic agents for the treatment of tumors, e.g. of ovarian carcinomas, testicular tumors, prostate carcinomas, bladder tumors, esophageal carcinomas and other malignant neoplasms, in particular of colon cancer, breast cancer, bronchial carcinomas and lung carcinomas.
  • tumors e.g. of ovarian carcinomas, testicular tumors, prostate carcinomas, bladder tumors, esophageal carcinomas and other malignant neoplasms, in particular of colon cancer, breast cancer, bronchial carcinomas and lung carcinomas.
  • the invention therefore furthermore relates to a method for the treatment of mammals, in particular humans, who are suffering from one of the diseases mentioned.
  • the method is characterized in that the diseased individual is administered a therapeutically effective and pharmacologically acceptable amount of one or more compounds of the formula I and / or their pharmacologically acceptable salts.
  • the invention also relates to the compounds of the formula I and their pharmacologically tolerable salts for use in the treatment of the abovementioned diseases.
  • the invention also encompasses the use of compounds of the formula I and their pharmacologically tolerable salts in the production of medicaments which are used to combat the diseases mentioned.
  • the invention further relates to medicaments which contain one or more compounds of the general formula I and / or their pharmacologically tolerable salts.
  • the medicaments are produced by processes known per se and familiar to the person skilled in the art.
  • auxiliaries which are suitable for the desired pharmaceutical formulations on the basis of his specialist knowledge.
  • active substance carriers for example antioxidants, dispersants, emulsifiers, defoamers, flavoring agents, preservatives, solubilizers, colorants or in particular permeation promoters and complexing agents (eg cyclodextrins) can be used.
  • the active substances can be administered rectally, by inhalation, parenterally (perlingually, intravenously, percutaneously) or orally.
  • the active ingredient (s) when given orally in a daily dose of about 0.5 to 30 mg / kg body weight, if desired in the form of several, preferably 1 to 4, single doses to achieve the desired result administer.
  • similar or generally lower doses in particular when the active compounds are administered intravenously can be used.
  • the pharmaceutical preparations can also contain one or more other pharmacologically active constituents of other groups of medicaments.
  • the treatment with the medicaments according to the invention can be combined with the administration of other cytostatics with different activity spectra. It may also be expedient to carry out the treatment according to the principle of cyclic cytostatic therapy. A recovery phase is inserted after each treatment.
  • the respective ZeilSuspension - ZR-75 or Amnion - (50000 cells / ml in RIMEN + 10% FCS + insulin) is incubated in culture dishes in the incubator for 24 h. After this time the cells have grown, the medium is aspirated and replaced by new medium without (control) or with test substance.
  • the medium used for the measurement of the substance effects (RIMEN) contains 2% estrogen-free FCS (estrogen-free by dextran / activated carbon treatment) and no insulin.
  • the cell lines are treated with test substance for 6 days each. The medium is replaced after 72 hours. After 6 days of substance incubation, cell growth is quantified by determining the DNA content according to BURTON (J. Steroid Biochem. 20, 1083-1088, 1984).
  • the compound 5-acety1-2,6-dimethyl-3- [5- (4,4-diphenyl-1-piperidinyl) pentanoyl] -4- (3-nitrophenyl) pyridine fumarate inhibits cell proliferation with a IC value of 0.8 ⁇ M (ZR-75) or> 5 ⁇ M (Amnion).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Des dihydropyridines ayant la formule (I), dans laquelle les substituants et les symboles ont les notations données dans la description, constituent de nouvelles substances ayant des propriétés pharmacologiques intéressantes.
EP91907002A 1990-04-10 1991-04-08 Pyridines utiles comme medicaments Withdrawn EP0524974A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1222/90 1990-04-10
CH122290 1990-04-10

Publications (1)

Publication Number Publication Date
EP0524974A1 true EP0524974A1 (fr) 1993-02-03

Family

ID=4205352

Family Applications (1)

Application Number Title Priority Date Filing Date
EP91907002A Withdrawn EP0524974A1 (fr) 1990-04-10 1991-04-08 Pyridines utiles comme medicaments

Country Status (6)

Country Link
US (1) US5352684A (fr)
EP (1) EP0524974A1 (fr)
JP (1) JPH05506216A (fr)
AU (1) AU652747B2 (fr)
CA (1) CA2080127A1 (fr)
WO (1) WO1991015484A1 (fr)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW232013B (fr) * 1992-04-24 1994-10-11 Takeda Pharm Industry Co Ltd
US5455253A (en) * 1992-10-20 1995-10-03 Zeneca Limited Heterocyclic derivatives
EP0634169B1 (fr) * 1993-06-29 2000-01-05 Takeda Chemical Industries, Ltd. Dérivés quinolines ou quinazolines et leur utilisation dans la fabrication d'un médicament pour le traitement de l'ostéoporose
CA2184392A1 (fr) * 1994-03-08 1995-09-14 Takashi Sohda Derives de la quinoline ou de la quinazoline, agents anti-inflammatoires, particulierement utiles pour traiter l'arthrite
RU2065299C1 (ru) * 1994-07-15 1996-08-20 Акционерное общество закрытого типа "Олвик" Ноотропное и транквилизирующее средство
DE19624704A1 (de) * 1996-06-20 1998-01-08 Klinge Co Chem Pharm Fab Neue Pyridylalkansäureamide
US6451816B1 (en) 1997-06-20 2002-09-17 Klinge Pharma Gmbh Use of pyridyl alkane, pyridyl alkene and/or pyridyl alkine acid amides in the treatment of tumors or for immunosuppression
DE19624668A1 (de) * 1996-06-20 1998-02-19 Klinge Co Chem Pharm Fab Verwendung von Pyridylalkan-, Pyridylalken- bzw. Pyridylalkinsäureamiden
DE19624659A1 (de) 1996-06-20 1998-01-08 Klinge Co Chem Pharm Fab Neue Pyridylalken- und Pyridylalkinsäureamide
HU221810B1 (hu) * 1997-08-12 2003-01-28 EGIS Gyógyszergyár Rt. Eljárás amlodipin-bezilát előállítására és az eljárás intermedierjei
DE19756235A1 (de) 1997-12-17 1999-07-01 Klinge Co Chem Pharm Fab Neue piperidinylsubstituierte Pyridylalkan- alken- und -alkincarbonsäureamide
DE19756261A1 (de) 1997-12-17 1999-07-01 Klinge Co Chem Pharm Fab Neue arylsubstituierte Pyridylalkan-, alken- und alkincarbonsäureamide
DE19756212A1 (de) 1997-12-17 1999-07-01 Klinge Co Chem Pharm Fab Neue, mit einem cyclischen Imid substituierte Pyridylalkan-, alken- und -alkincarbonsäureamide
US6903118B1 (en) 1997-12-17 2005-06-07 Klinge Pharma Gmbh Piperazinyl-substituted pyridylalkane, alkene and alkine carboxamides
EP1031564A1 (fr) 1999-02-26 2000-08-30 Klinge Pharma GmbH Inhibiteurs de la formation du nicotinamide mononucléotide et leur utilisation dans le traitement du cancer
SE9902765D0 (sv) 1999-07-21 1999-07-21 Astra Pharma Prod Novel compounds
KR100354806B1 (ko) * 2000-06-21 2002-10-05 한국유나이티드제약 주식회사 암로디핀 베실레이트의 신규 중간체 및 그의 제조방법
CA2659747C (fr) 2006-08-03 2015-09-08 Trustees Of Tufts College Analogues de la niacine sans effets de bouffees congestives et procedes d'utilisation
US20110123470A1 (en) * 2007-05-04 2011-05-26 Aquapharm Bio-Discovery Ltd. Natural bioactive compounds

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US4975440A (en) * 1984-09-28 1990-12-04 Byk Gulden Lomberg Chemische Fabrik Gmbh Optically-active 1,4-dihydropyridine
EP0176956B1 (fr) * 1984-09-28 1994-06-15 Byk Gulden Lomberg Chemische Fabrik GmbH Composés diaryliques
FI880990A (fi) * 1987-03-05 1988-09-06 Yamanouchi Pharma Co Ltd Pyridinderivat, deras framstaellning, dessa innehaollande aemnen foer att skoeta och foerebygga leverskador, och metod foer att skoeta och foerebygga leverskador genom att anvaenda dessa aemnen.
AU7652391A (en) * 1990-04-10 1991-10-30 Byk Gulden Lomberg Chemische Fabrik Gmbh Novel pyridine esters

Non-Patent Citations (1)

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Title
See references of WO9115484A1 *

Also Published As

Publication number Publication date
CA2080127A1 (fr) 1991-10-11
US5352684A (en) 1994-10-04
JPH05506216A (ja) 1993-09-16
AU652747B2 (en) 1994-09-08
AU7566091A (en) 1991-10-30
WO1991015484A1 (fr) 1991-10-17

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