Kuraray Co., Ltd.

Agency of Industrial Science and Technology

Ministry of International Trade & Industry

Agency of Industrial Science and Technology Ministry of International

Nihon Iyakuhin Kogyo Co., Ltd.

Yoshiaki Omura

Takashi Nishida

Yoshiji Fujita

Fumio Mori

Kazuo Itoi

Takeo Hosogai

Yoshin Tamai

Yoichi Ninagawa

Fumio Wada

Sukeji Aihara

Masao Tanihara

Toshihide Nakashima

Koichi Takakura

Hideaki Yamada

Takashi Ohnishi

Manzo Shiono

Susumu Okabe

Kiichiro Oka

Masahisa Tanomura

Akira Kobayashi

Masao Mizuno

Michitaka Ogawa

Muneo Kobayashi

Hiromasa Nakamoto

Kazuo Kumamoto

Hiroko Murakami

Yuki Nogami

Takashi Hishida

A human IgG.sub.1 type monoclonal antibody which possesses a molecular weight in the range of 180,000.+-.20,000 as measured by the method of polyacrylamide gel electrophoresis performed in the presence of sodium dodecyl sulfate and is specific to nicotinic acetylcholine receptor. The human IgG.sub.1 type monoclonal antibody mentioned above is produced by a method which comprises fusing human cells capable of producing an antibody against nicotinic acetylcholine receptor with propagable human cells thereby giving rise to a hybridoma capable of producing the aforementioned human IgG.sub.1 type monoclonal antibody, selecting the hybridoma from the production of the fusion, culturing the hybridoma thereby giving rise to the aforementioned human IgG.sub.1 type monoclonal antibody, and selecting the antibody from the cultured medium. The hybridoma mentioned above is also identified.

Human IgG.sub.1 monoclonal antibody specific for the nicotinic

There is disclosed an adsorbent, comprising a carrier on which is immobilized a peptide possessing an ability to bind to the human antibody to the nicotinic acetylcholine receptor and represented by the formula:

Adsorbent, method for production thereof, and method for use thereof

A monoclonal anti-idiotypic antibody specific to a human IgG.sub.1 type monoclonal antibody possessing specificity to nicotinic acetylcholine receptor; a method for the production of the aforementioned monoclonal anti-idiotypic antibody by the steps of immunizing an animal with a human IgG.sub.1 type monoclonal antibody specific to nicotinic acetylcholine receptor, collecting antibody-producing cells from the animal, fusing the collected cells with neoplastic cells, selecting from the product of fusion a hybridoma capable of producing a monoclonal anti-idiotypic antibody specific to the human IgG.sub.1 type monoclonal antibody possessing specificity to nicotinic acetylcholine receptor, propagating the selected hybridoma thereby giving rise to said monoclonal anti-idiotypic antibody, and collecting the produced monoclonal anti-idiotypic antibody; and use of the monoclonal anti-idiotypic antibody as a reagent and as an adsorbent.

Monoclonal anti-idiotypic antibody, method for production thereof, and

A peptide is disclosed which is represented by the formula:

Peptide

Novel pesticidal compositions are comprised of a 2,2-dimethyl-3-(substituted ethyl)cyclopropanecarboxylic acid ester as the active ingredient, said cyclopropanecarboxylate having the structural formula: ##STR1## wherein X, Y and Z are the same or different and at least two of same are chlorine or bromine, with the remaining one being hydrogen, methyl, chlorine or bromine; R is an alcohol residue represented by one of the following structural formulae (II), (III), (IV) and (V): ##STR2## where A represents hydrogen, cyano, ethynyl or thiocarbamoyl; Q is hydrogen, chlorine, bromine, fluorine, methyl or trifluoromethyl; R.sup.1 is propargyl or benzyl; R.sup.2 represents 2-halogeno-3-phenyl-1-propen-1-yl, (dihalogenovinyloxy)phenyl, benzylphenyl, phthalimido, thiophthalimido, di- or tetrahydrophthalimido or dialkylmaleimido; R.sup.3 represents allyl, 2,4-pentadienyl, propargyl or benzyl.

Certain cyclopropane carboxylic acid esters and their pesticidal use

A geranylgeranylacetamide compound having a piperazine ring represented by the following formula (I) ##STR1## wherein R represents a member selected from the class consisting of a hydrogen atom, C.sub.1 -C.sub.5 alkyl groups which are unsubstituted or mono-substituted by a halogen atom, C.sub.2 -C.sub.5 alkenyl groups and C.sub.7 -C.sub.8 aralkyl groups, R.sub.1 represents a C.sub.1 -C.sub.3 alkyl group, and n represents 0, 1 or 2, and a pharmaceutically acceptable acid addition salt thereof. The aforesaid compound can be prepared by reacting geranylgeranylacetic acid or its reactive derivative with a piperazine compound, and thereafter, if desired, transforming the free geranylgeranylacetamide compound thus obtained into its pharmaceutically acceptable acid addition salt. A pharmaceutical composition containing said compound exhibits antiulcerogenic activity, particularly excellent antipeptic ulcerogenic activity, and is useful as an agent for treating ulcers.

Geranylgeranylacetamide compounds having a piperazine ring, salts

Novel insecticidal compositions are comprised of an active isovalerate having the structural formula: ##STR1## wherein Z.sup.1 is hydrogen, ##STR2## Z.sup.2 is either ##STR3## when Z.sup.1 is hydrogen, or hydrogen when Z.sup.1 is either ##STR4## A, when Z.sup.1 is ##STR5## is cyano or ethynyl or, when Z.sup.1 is other than ##STR6## is hydrogen, cyano or ethynyl; X and Y which may be the same or different are chlorine or bromine.

Insecticides and insecticidal compositions

2,2-Dimethyl-3-(substituted ethyl)cyclopropane carboxylate pesticidal

A new pyrethroid compound which is low in toxicity to fish and a pesticidal composition containing the same as an active ingredient are provided. The above pyrethroid compound is a substituted cyclopropanecarboxylic acid ester of the general formula: ##STR1## (wherein A is a hydrogen atom or an ethynyl group) Despite its broad pesticidal spectrum and high pesticidal activity, this ester is very low in toxicity to man and domestic animals and especially low in toxicity to fish as compared with the conventional pyrethroid compounds.

Substituted cyclopropanecarboxylic acid esters and pesticidal

Racemic modifications each consisting of specific isomers of .alpha.-cyano-3-phenoxybenzyl cis- or trans-2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropanecarboxylate with the absolute configurations [.alpha.S, 1R] an [.alpha.R, 1S] with respect to the asymmetric carbon atoms in the alcohol and acid moieties, a method of producing the same and pesticidal compositions containing the same as active ingredient are provided. .alpha.-Cyano-3-phenoxybenzyl cis- or trans-2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropanecarboxylate has higher pesticidal activities than those pesticides that are in general use and consequently selective production of the above specific racemic modification as defined by the combinations of the absolute configuration with respect to the asymmetric carbon atom at the position in the alcohol moiety and the absolute configuration with respect to the asymmetric carbon atom in the acid moiety provides compounds having still higher pesticidal activities.

Racemic modification consisting of specific isomers of

Novel farnesylacetic acid amide compounds represented by general formula ##STR1## wherein A is alkylene of at least 2 carbon atoms, R.sup.1 is H or lower alkyl, and R.sup.2 and R.sup.3 are each independently H, alkyl, cycloalkyl, alkenyl, aryl or aralkyl, or either one of R.sup.2 and R.sup.3 is such a group that forms, together with A, a piperidine or pyrrolidine ring which contains as constituent thereof the nitrogen atom lying therebetween, or R.sup.2 and R.sup.3 combinedly represent a group which forms, together with the nitrogen atom to which they are bonded, a piperidine, pyrrolidine or piperazine ring; and salts thereof have antiulcerogenic and antibacterial activities.

Farnesylacetic acid amides

Novel pesticidal compositions are comprised of a 2,2-dimethyl-3-(substituted ethyl)cyclopropanecarboxylic acid ester as the active ingredient, said cyclopropanecarboxylate having the structural formula: ##STR1## wherein X, Y and Z are the same or different and at least two of same are chlorine or bromine, with the remaining one being hyrogen, methyl, chlorine or bromine; R is an alcohol residue represented by one of the following structural formulae (II), (III), (IV) and (V): ##STR2## where A represents hydrogen, cyano, ethynyl or thiocarbamoyl; Q is hydrogen, chlorine, bromine, fluorine, methyl or trifluoromethyl; R.sup.1 is propargyl or benzyl; R.sup.2 represents 2-halogeno-3-phenyl-1-propen-1-yl, (dihalogenovinyloxy)phenyl, benzylphenyl, phthalimido, thiophthalimido, di- or tetrahydrophthalimido or dialkylmaleido; R.sup.3 represents allyl, 2,4-pentadienyl, propargyl or benzyl.

Novel pesticides and pesticidal compositions cyclopropanecarboxylates

Novel farnesylacetic acid ester derivatives containing an amine nitrogen in the alcohol residue thereof and represented by the following general formula exhibit high levels of antiulcerogenic activity and very low levels of toxicity: ##STR1## wherein A is an alkylene radical containing at least 2 carbon atoms; R.sup.1 is H, alkyl, cycloalkyl, aryl, aralkyl or alkenyl; R.sup.2 and R.sup.3 are independently H, alkyl, aryl, aralkyl or alkenyl or one of R.sup.2 and R.sup.3 forms, together with A, a piperidine, pyrrolidine, tetrahydropyrimidine or piperazine ring which contains the nitrogen atom lying therebetween or R.sup.2 and R.sup.3 combine to form, together with the adjacent nitrogen atom, a piperazine ring; provided that the total number of carbon atoms contained in A, R.sup.1, R.sup.2 and R.sup.3 is at least 5.

Farnesylacetic acid ester derivatives

dl-.alpha.-Tocopherol is prepared by condensing trimethylhydroquinone with phytyl halide in a chlorinated lower aliphatic hydrocarbon solvent, in the presence of metallic tin and a Friedel-Crafts catalyst.

Preparation of dl-.alpha.-tocopherol

Novel substituted propargyl alcohols of the formula: ##STR1## novel allylic alcohols of the formula: ##STR2## and; .delta.,.epsilon.-unsaturated ketones of the formula: ##STR3## are provided. In the above formulas, R represents a group of the formula: ##STR4## wherein X.sub.1 and X.sub.2 are both hydrogen atoms or wherein one of X.sub.1 and X.sub.2 is a hydrogen atom, the other jointly with Z represents a bond; Z jointly with X.sub.1 or X.sub.2 represents a bond or separately represent a hydrogen atom, a hydroxyl group or a lower alkoxy group; R.sub.1 and R.sub.2 are the same or different and represents hydrogen atoms or lower alkyl groups; n is 1 or 2; and when n is 2, X.sub.1, X.sub.2, X, R.sub.1 and R.sub.2 may be the same or different. These novel compounds are easily produced and are useful as perfumes and as interrelated intermediates for the production of terpenoid compounds.

Growing community of inventors

Okayama, Japan

Yoshiaki Omura