Banyu Pharmaceutical Co. Ltd

Sds Biotech K.k.

Takashi Nomoto

Masahiro Hayashi

Yoshimi Tsuchiya

Yoshikazu Iwasawa

Yasufumi Nagata

Morihiro Mitsuya

Katsumasa Nonoshita

Masaru Nishikibe

Kumiko Kawakami

Yoshiaki Iida

Kenji Ohwaki

Hirokazu Ohsawa

Toshio Kamei

Toshihiko Satoh

Mitsuru Ohkubo

Masaaki Sakai

Ryutaro Katsuki

Tomoko Muraki

Satohiro Midorikawa

Hitoshi Masaki

Yumiko Sakuma

Tomoaki Matsumura

Yoshio Sawasaki

Agri-horticultural pest control compositions having outstanding control effect on pests, in particular, agri-horticultural pests, which comprise as active ingredients one or more 4-(3-butynyl)aminopyrimidine derivatives represented by the general formula [I], namely, 

Agri-horticultural pest control compositions comprising 4-(3-butynyl)aminopyrimidine derivatives

Novel 4-(3-butynyl)aminopyrimidine derivatives represented by general formula [I] are useful as pest control agents. In general formula [I], Ris a mono- or bi-cyclic ring which may contain 0 to 3 heteroatoms, for example, phenyl or oxazolyl; Ris a hydrogen atom, &#x2014;R, &#x2014;OR, &#x2014;C(O)OR, &#x2014;C(O)NHR, &#x2014;CONR(wherein R is straight-chain or branched Calkyl, or the like), hydroxyalkyl, or the like; Ris a hydrogen atom, a halogen atom, acyloxy represented by (straight-chain or branched Caliphatic hydrocarbon group) &#x2014;CO&#x2014;O&#x2014;, or the like; and Ris a hydrogen atom, a halogen atom, Calkyl, or the like, or alternatively, Rand Rtogether with the carbon atoms on the pyrimidine ring may form a thiophene ring, a pyrrole ring, an imidazole ring, a benzene ring, a pyrimidine ring, a furan ring, a pyrazine ring, or a pyrrolidine ring.

4-(3-butynyl)aminopyrimidine derivatives as pest control agents for agricultural and horticultural use

The invention relates to compounds represented by the general formula [I] ##STR1## [wherein Ar means an aryl group or a heteroaryl group which may have a substitutive group selected from a group consisting of a halogen atom, a lower alkyl group and a lower alkoxy group; R.sup.1 means a C.sub.3 -C.sub.6 cycloalkyl group which is substitutable with a fluorine atom; R.sup.2 and R.sup.4 mean hydrogen atoms, groups represented by --(A.sup.1).sub.m --NH--B or the like; R.sup.3 and R.sup.5 mean hydrogen atoms, C.sub.1 -C.sub.6 aliphatic hydrocarbon groups or the like which are substitutable with a lower alkyl group(s); n means 0 or 1; and X means an oxygen atom or a sulfur atom]. Compounds according to the invention, since they not only have potent selective antagonistic activity against muscarinic M.sub.3 receptors but also exhibit excellent oral activity, durability of action and pharmacokinetics, are very useful as safe and effective remedies against respiratory, urinary and digestive diseases with little adverse side effects.

N-acyl cyclic amine derivatives

In the production of fluorine-containing 1,4-disubstituted piperidine derivatives by the reaction of a carboxylic acid of formula where Ar represents aryl or heteroaryl and R.sup.10 represents C.sub.3 -C.sub.6 cycloalkyl in which up to 4 hydrogen atoms are substituted with fluorine or C.sub.3 -C.sub.6 cycloalkyl having 1 to 2 protected or unprotected hydroxyl or oxo groups, or a reactive derivative thereof, with a piperidine derivative of formula [IV] as defined in the specification, especially useful results are obtained using 4-amino-1-(6-aminopyridin-2-ylmethyl)piperidine or a salt thereof, e.g., trihydrochloride, as the piperidine derivative.

Fluorine-containing 1, 4-disubstituted piperidine derivatives

Novel fluorine-containing 1,4-disubstituted piperidine derivatives, represented by general formula �I! ##STR1## such as, for example, (2R)-N-�1-(6-aminopyridin-2-ylmethyl)piperidin-4-yl!-2-�(1R)-3,3-difluoroc yclopentyl!-2-hydroxy-2-phenylacetamide or pharmaceutically acceptable salt thereof, are potent and selective antagonists for muscarinic M.sub.3 receptors with little side effects. The compounds of formula �I! exhibit excellent oral activity, duration of activity and pharmacolkinetics. They are useful for treatment and prophylaxis of respiratory diseases, such as chronic obstructive pulmonary diseases; urinary diseases, such as urinary incontinence; and digestive diseases, such as irritable bowel syndrome, and motion sickness.

Fluorine-containing 1,4-disubstituted piperidine derivatives

A compound of the formula (I) or its pharmaceutically acceptable salt or ester: ##STR1## wherein each of ##STR2## which are the same or different, is an aryl group or a heteroaromatic ring group; A is a C.sub.3-8 linear saturated or unsaturated aliphatic hydrocarbon group which may have substituent(s) selected from the group consisting of a lower alkyl group, a hydroxyl group, a lower alkoxy group, a carboxyl group, an aryl group and an aralkyl group; Q is a single bond or a group of the formula --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --OCH.sub.2 --, --SCH.sub.2 --, --CH.sub.2 O-- or --CH.sub.2 S--; each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 which are the same or different, is a hydrogen atom, a halogen atom, a lower alkyl group, a hydroxyl group, a lower alkoxy group, or an aryl or heteroaromatic ring group which may have substituent(s) selected from the group consisting of a halogen atom, a lower alkyl group and a lower alkoxy group; each of R.sup.5, R.sup.6 and R.sup.7 which are the same or different, is a hydrogen atom or a lower alkyl group; and R.sup.8 is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group or an aralkyl group, provided that when Q is a single bond, ##STR3## are not simultaneously 4-chlorophenyl groups.

Substituted amic acid derivatives

1,4-di-substituted piperidine derivatives

A compound of the formula (I) or its pharmaceutically acceptable salt or ester: ##STR1## wherein each of the substituents are herein defined.

A compound of the formula (I) or its pharmaceutically acceptable salt or ester: ##STR1## and intermediates thereof.

Substitute amic acid derivatives

Substituted heterocyclic derivative having squalene epoxidase inhibition

Substituted amine derivatives represented by the general formula ##STR1## wherein Q is --C--D--E--F--G--M-- or --N--H--I--J--K--L-- [C, D, E, F, G, H, I, J, K and L are each O, S, a carbonyl group, --CHR.sup.a --, --R.sup.b .dbd. or --NR.sup.c -- (R.sup.a, R.sup.b and R.sup.c are each H or a lower alkyl group), M and N are each an aromatic ring of 5-6 members optionally having a halogen, OH, LN, a lower alkyl group or a lower alkoxy group, provided that L is not O, S, or --NR.sup.c --]; R is a heterocyclic ring of 5-6 members; R.sup.1 is H, a lower alkyl group, a lower haloalkyl group, a lower alkenyl group, a lower alkynyl group or a cycloalkyl group; R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are each H, a halogen or a lower alkyl group or two of them denote a single bond; R.sup.8 and R.sup.9 are each F, CF.sub.3 or a lower alkyl group or are a cycloalkane in combination thereof; and R.sup.10 is H, F, CF.sub.3 an acetoxy group, a lower alkyl group or a lower alkoxy group. These compounds inhibit biosynthesis of cholesterol in mammals by inhibiting their squalene epoxidase, and thereby lower their blood cholesterol values. Therefore, these compounds are expected to be effective as an agent for treatment and prophylaxis of diseases caused by excess of cholesterol, for example, obesity, hyperlipemia and arteriosclerosis and heart and encephalic diseases accompanying them.

Substituted amine derivatives having anti-hyperlipemia activity

Substituted amine derivatives represented by the general formula ##STR1## wherein Q is -C-D-E- F-G-M- or -N-H-I-J-K-L- [C, D, E, F, G, H, I, J, K and L are each O, S, a carbonyl group, -CHR.sup.2 -, -R.sup.b = or -NR.sup.c - (R.sup.a, R.sup.b and R.sup.c are each H or a lower alkyl group), M and N are each an aromatic ring of 5-6 members optionally having a halogen, OH, LN, a lower alkyl group or a lower alkoxy group, provided that L is not O, S, or -NR.sup.c -]; R is a heterocyclic ring of 5-6 members; R.sup.1 is H, a lower alkyl group, a lower haloalkyl group, a lower alkenyl group, a lower alkynyl group or a cycloalkyl group; R.sup.2, R.sup.3, R.sup.4, R.sup.5 R.sup.6 and R.sup.7 are each H, a halogen or a lower alkyl group or two of them denote a single bond; R.sup.8 and R.sup.9 are each F, CF.sub.3 or a lower alkyl group or are a cycloalkane in combination thereof; and R.sup.10 is H, F, CF.sub. 3 an acetoxy group, a lower alkyl group or a lower alkoxy group. These compounds inhibit biosynthesis of cholesterol in mammals by inhibiting their squalene epoxidase, and thereby lower their blood cholesterol values. Therefore, these compounds are expected to be effective as an agent for treatment and prophylaxis of diseases caused by excess of cholesterol, for example, obesity, hyperlipemia and arteriosclerosis and heart and encephalic diseases accompanying them.

Growing community of inventors

Tsukuba, Japan

Takashi Nomoto