Takeda Chemical Industries, Inc.

Masayuki Takizawa

Junji Mizoguchi

Takashi Sohda

Tsuneo Yasuma

Yukio Fujisawa

Masakuni Kori

Koji Yoshimura

Toshiro Yamashita

Hiroshi Nara

Shigetoshi Tsubotani

Yoshiaki Shimizu

Mikio Shirasaki

The present invention provides a compound represented by Formula:wherein ring A and ring B may be same or different and each is an optionally substituted homocyclic or heterocyclic ring and the like, each Rmay be same or different and is a hydrogen atom, an optionally substituted hydrocarbon group, an acyl group, an optionally substituted heterocyclic group or SR, etc., Xis a bond, an optionally substituted divalent Caliphatic hydrocarbon group or &#x2014;NR&#x2014;, etc, Xis a bond, an optionally substituted divalent Caliphatic hydrocarbon group, &#x2014;NR&#x2014;, &#x2014;O&#x2014; or &#x2014;S(O)&#x2014; (wherein p is 0, 1 or 2), each Y may be same or different and is a hydrogen atom, an optionally substituted hydrocarbon group, a halogen atom, a carboxyl group, an acyl group, an optionally substituted hydroxy group, an optionally substituted amino group, SR, an oxo group, a thioxo group, an optionally substituted imino group, a nitro group, a cyano group, etc., each m may be same or different and is 0 or 1, n is an integer of 1 to 3, qis an integer of 1 to 2n+4, qis an integer of 0 to 2n+3, and the sum of qand qis 2n+4 or a salt thereof.

Thiol compounds, their production and use

Compounds represented by general formula (1) or salts thereof which have a matrix metalloprotease inhibitory activity and are useful as drugs, wherein the rings A and B represent each an optionally substituted homocycle or heterocycle, etc.; R s are the same or different and each represents hydrogen, optionally substituted hydrocarbyl, acyl, etc.; X represents a bond, optionally substituted divalent aliphatic hydrocarbyl, etc.; X represents a bond, optionally substituted divalent aliphatic hydrocarbyl, &mdash;O&mdash;, etc.; Ys are the same or different represents hydrogen, optionally substituted hydrocarbyl, oxo, etc.; m is 0 or 1; n is an integer of 1 to 3; q is an integer of 1 to 2n&plus;4; and q is an integer of 0 to 2n&plus;3, provided that q &plus;q is 2n&plus;4.

The present invention provides a cathepsin L inhibitor containing a compound of the formula: ##STR1## wherein R.sup.1 is a hydrogen atom or an arylalkyl, heterocyclic-alkyl or lower alkyl group which may be substituted; R.sup.2 and R.sup.3 independently are a hydrogen atom or a hydrocarbon residue which may be substituted; R.sup.4 is an alkanoyl, sulfonyl, carbonyloxy, carbamoyl or thiocarbamoyl group which may be substituted; X is formula: --CHO or --CH.sub.2 OB (wherein B is a hydrogen atom or a protecting group of hydroxyl group); m and n independently are an integer of 0 or 1; provided that R.sup.4 is an alkanoyl group substituted by aryl, a sulfonyl group substituted by aryl having more than 9 carbon atoms or by lower alkyl, or a carbamoyl or thiocarbamoyl group which may be substituted when R.sup.1 is an unsubstituted lower alkyl, arylalkyl on methylthioethyl group, R.sup.2 and R.sup.3 independently are a lower alkyl or arylalkyl, X is --CHO, m is 1 and n is 0 or 1, or a salt thereof.

Method for treating osteoporosis

The present invention provides a cathepsin L inhibitor containing a compound of the formula: ##STR1## wherein R.sup.1 is a hydrogen atom or an arylalkyl, heterocyclic-alkyl or lower alkyl group which may be substituted; R.sup.2 and R.sup.3 independently are a hydrogen atom or a hydrocarbon residue which may be substituted; R.sup.4 is an alkanoyl, sulfonyl, carbonyloxy, carbamoyl or thiocarbamoyl group which may be substituted; X is formula: --CHO or --CH.sub.2 OB (wherein B is a hydrogen atom or a protecting group of hydroxyl group); m and n independently are an integer of 0 or 1; provided that R.sup.4 is an alkanoyl group substituted by aryl, a sulfonyl group substituted by aryl having more than 9 carbon atoms or by lower alkyl, or a carbamoyl or thiocarbamoyl group which may be substituted when R.sup.1 is an unsubstituted lower alkyl, arylalkyl on methylthioethyl group, R.sup.2 and R.sup.3 independently are a lower alkyl or arylalkyl, X is --CHO, m is 1 and n is 0 or 1, or a salt thereof. Compound (I) is useful as a prophylactic/therapeutic agent for osteoporosis.

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Growing community of inventors

Kobe, Japan

Masayuki Takizawa