Fused pyramidine derivative and use thereof

TECHNICAL FIELD

The present invention relates to a fused pyrimidine derivative having excellent antagonistic activity against gonadotropin releasing hormone.

BACKGROUND ART

Secretion of anterior pituitary hormones is regulated by peripheral hormones secreted from target organs of the respective hormones and by secretion-promoting or secretion-inhibiting hormones secreted from the hypothalamus, which is the upper central organ of the anterior lobe of the pituitary (hereinafter, these hormones are collectively called “hypothalamic hormones” in the present specification). So far, the existence of nine species of hypothalamic hormones has been confirmed, including, for example, thyrotropin releasing hormone (TRH), gonadotropin releasing hormone [GnRH, sometimes called LH-RH (luteinizing hormone releasing hormone)] and the like. These hypothalamic hormones are believed to show their actions via the receptors that are considered to exist in the anterior lobe of the pituitary, and analysis of the receptor gene which is specific to these hormones, including for humans, is being made. Accordingly, antagonists or agonists specifically and selectively acting on these receptors should control the action of the hypothalamic hormones and the secretion of anterior pituitary hormones. As a result, such antagonists or agonists are expected to be useful in preventing or treating anterior pituitary hormone-dependent diseases.

As the compounds having GnRH-antagonizing activity, there are known GnRH-derived linear peptides (Patent Document 1 and Patent Document 2), a cyclic hexapeptide derivative (Patent Document 3), a bicyclic peptide derivative (Non-Patent Document 1) and the like. Non-peptidic compounds having GnRH-antagonizing activity include the compounds described in Patent Documents 4 through 11.

Further, as the compounds having an aromatic group having amide or sulfonamide bound via a nitrogen atom of a fused pyrimidine ring, the following compounds may be mentioned.

Patent Document 12 describes compounds represented by the formula:
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as a neurovascularization inhibitor.

Patent Document 13 describes compounds represented by the formula:
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as a cysteine protease inhibitor.

Patent Document 14 describes a compound represented by the formula:
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as a vasopressin antagonist as well as a vasopressin agonist.

Non-Patent Document 2 describes synthesis of compounds represented by the formula:
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Patent Document 15 describes a compound represented by the formula:
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as a carbonic anhydrase inhibitor.

Non-Patent Document 3 describes synthesis of a compound represented by the formula:
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Non-Patent Document 4 describes synthesis of compounds represented by the formula:
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Non-Patent Document 5 describes synthesis of a compound represented by the formula:
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Non-Patent Document 6 describes compounds represented by the formula:
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as compounds having antibacterial activity.

Non-Patent Document 7 describes synthesis of compounds represented by the formula:
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Non-Patent Document 8 describes synthesis of a compound represented by the formula:
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Patent Document 16 describes a compound represented by the formula:
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as a starting material for the synthesis of medicine, dye and insecticide.

Non-Patent Document 9 describes the following compounds as LT00082529 and LT00082554:
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Patent Document 17 describes a method for synthesis of the following indole derivatives as chymase inhibitors:
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Patent Document 18 describes compounds represented by the formula:
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as colorants or color-forming agents.

Patent Document 19 describes compounds represented by the formula:
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as Cdk2 and Cdk5 kinase inhibitors for the prevention of cell growth-related diseases.

Non-Patent Document 10 describes a method for solid phase synthesis of compounds represented by the formula:
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Non-Patent Document 11 describes a compound represented by the formula:
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[Patent Document 1] U.S. Pat. No. 5,140,009

[Patent Document 2] U.S. Pat. No. 5,171,835

[Patent Document 3] JP-A No. 61-191698

[Patent Document 4] JP-A No. 8-295693 (WO 95/28405)

[Patent Document 5] JP-A No. 9-169768 (WO 96124597)

[Patent Document 6] JP-A No. 9-169735 (WO 97/14682)

[Patent Document 7] JP-A No. 9-169767 (WO 97/14697)

[Patent Document 8] JP-A No. 11-315079 (WO 99/33831)

[Patent Document 9] JP-A No. 2000-219691 (WO 00/00493)

[Patent Document 10] JP-A No. 2001-278884 (WO 00/56739)

[Patent Document 11] JP-A No. 2002-30087

[Patent Document 12] JP-A No. 10-259176

[Patent Document 13] DE 19650975 A

[Patent Document 14] JP-A No. 9-221476 (WO 95/34540)

[Patent Document 15] WO 91/14430

[Patent Document 16] GB 753171 A

[Patent Document 17] WO 2001/032621

[Patent Document 18] DE 3420799

[Patent Document 19] WO 2003/101985

[Non-Patent Document 1] Journal of Medicinal Chemistry, Vol. 36, pp. 3265-3273 (1993)

[Non-Patent Document 2] Journal of Heterocyclic Chemistry, Vol. 32(4), pp. 1181-1183 (1995)

[Non-Patent Document 3] Journal of the Chemical Society, Perkin Transaction 1, Vol. 11, pp. 2884-2889 (1981)

[Non-Patent Document 4] Acta Chimica Academiae Scientiarum Hungaricae, Vol. 107(1), pp. 57-66 (1981)

[Non-Patent Document 5] Journal of Organic Chemistry, Vol. 41(16), pp. 2728-2731 (1976)

[Non-Patent Document 6] Pharmazie, Vol. 30(4), pp. 254-255 (1975)

[Non-Patent Document 7] Acta Chimica Academiae Scientiarum Hungaricae, Vol. 48(1), pp. 77-87 (1966)

[Non-Patent Document 8] Chemische Berichte, Vol. 99(5), pp. 1532-1540 (1966)

[Non-Patent Document 9] LaboTest Stock catalogue, published on Jan. 2, 2002

[Non-Patent Document 10] Tetrahedron, Vol. 59(29), pp. 5603-5608 (2003)

[Non-Patent Document 11] Journal of Heterocyclic 25 Chemistry, Vol. 27(5), pp. 1341-1344 (1990)

DISCLOSURE OF THE INVENTION

Peptidic compounds have many problems to be resolved in the aspects of oral absorption, administration mode, dosage, drug stability, sustained action, metabolic stability and the like. There is a strong demand for a GnRH antagonist having excellent oral absorption, especially a non-peptidic antagonist, which has excellent therapeutic effect on hormone-dependent cancers such as prostate cancer, endometriosis, precocious puberty and the like, and which does not show transient pituitary-gonadotropic action (acute action).

The inventors of the present invention have diligently conducted research and, as a result, have found that a compound represented by the formula:
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wherein R^1ais a hydrocarbon group which may be substituted or a hydrogen atom,

ring A^ais a 6-membered aromatic ring which may be further substituted,

ring B^ais a homocyclic or heterocyclic ring which may be further substituted,

W^ais an oxygen atom or a sulfur atom,

X^a1and X^a2, which may be identical or different, are each a hydrogen atom, a hydrocarbon group which may be substituted, or a heterocyclic group which may be substituted, or X^a1and X^a2together may form an oxygen atom, a sulfur atom, or NR^3a(wherein R^3ais a hydrocarbon group which may be substituted or a hydrogen atom), and

Y^ais C_1-6alkylene which may be substituted or a bond, (hereinafter, may be briefly referred to as Compound (II)) or a salt thereof has unexpectedly excellent GnRH antagonizing activity, especially strong antagonist activity. Furthermore, they have found that the precursor of Compound (II) also is converted to Compound (II) in a mixture to be tested during testing (during the evaluation of compound activity) or in vivo, and thus, exhibits unexpectedly excellent GnRH antagonizing activity, especially strong antagonist activity. Moreover, they have also found for the first time that these compounds have low toxicity and are sufficiently satisfactory as medicines having GnRH antagonizing activity.

The inventors have also synthesized for the first time a fused pyrimidine derivative [hereinafter, may be briefly referred to as Compound (I). In addition, Compound (I) includes the compound represented by Formula (I-a) (hereinafter, may be briefly referred to as Compound (I-a)), and the compound represented by Formula (I-b) (hereinafter, may be briefly referred to as Compound (I-b)), and in the present specification, Compound (I) refers to both or either of Compound (I-a) and Compound (I-b)] represented by Formula (I-a):
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wherein ring A is a 6-membered aromatic ring which may be further substituted,

X is an oxygen atom, a sulfur atom or NR³(wherein R³is a hydrocarbon group which may be substituted or a hydrogen atom),

R¹is a hydrocarbon group which may be substituted or a hydrogen atom, and

R²is

(1) a group represented by the formula:
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[wherein ring B¹is a benzene ring which may be further substituted; Z¹is C_1-6alkylene which may be substituted or a bond; R⁴is (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; and R⁵is (a) a hydrocarbon group which may be substituted, or (b) a heterocyclic group which may be substituted; or R⁴and R⁵may form a ring together with the adjacent nitrogen atom],

(2) a group represented by the formula:
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[wherein ring B²is a benzene ring which may be further substituted; Z²is C_1-6alkylene which may be substituted or a bond; R⁶is (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; and R⁷is (a) a hydrocarbon group which may be substituted, or (b) a heterocyclic group which may be substituted; or R⁶and R⁷may form a ring together with the adjacent nitrogen atom],

(3) a group represented by the formula:
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[wherein ring B³is a benzene ring which may be further substituted; Z³is C₁-₆alkylene which may be substituted or a bond; R⁸is (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; and R⁹is (a) a hydrocarbon group which may be substituted, or (b) a heterocyclic group which may be substituted; or R⁸and R⁹may form a ring together with the adjacent nitrogen atom, provided that when R⁸is a hydrogen atom, R⁹is (a) an aryl group which may be substituted, (b) an aralkyl group which may be substituted, or (c) an alkyl group substituted with a heterocyclic group which may be substituted],

(4) a group represented by the formula:
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[wherein ring B⁴is a benzene ring which may be further substituted; Z⁴is C_1-6alkylene which may be substituted or a bond; R¹⁰is (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; and R¹¹is (a) an aromatic group which may be substituted, (b) an aralkyl group which may be substituted, or (c) an alkyl group substituted with a heterocyclic group which may be substituted; or R¹⁰and R¹¹may form, together with the adjacent nitrogen atom, a heterocyclic ring comprising carbon and nitrogen atoms as ring-constituting moieties],

(5) a group represented by the formula:
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[wherein ring B⁵is a benzene ring which may be further substituted; Z⁵is C_1-6alkylene which may be substituted or a bond; and R¹²and R¹³, which may be identical or different, are each (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; or R¹²and R¹³may form a ring together with the adjacent nitrogen atom],

(6) a group represented by the formula:
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[wherein ring B⁶is a benzene ring which may be further substituted; Z⁶is C_1-6alkylene which may be substituted or a bond; and R¹⁴and R¹⁵, which may be identical or different, are each (a) a hydrocarbon group which may be substituted, or (b) a heterocyclic group which may be substituted; or R¹⁴and R¹⁵may form a ring together with the adjacent nitrogen atom],

(7) a group represented by the formula:
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[wherein ring B⁷is a C_10-14aryl ring which may be further substituted, or an aromatic heterocycle which may be further substituted; Z⁷is C_1-6alkylene which may be substituted or a bond; R¹⁶is (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; and R¹⁷is (a) a hydrocarbon group which may be substituted, or (b) a heterocyclic group which may be substituted; or R¹⁶and R¹⁷may form a ring together with the adjacent nitrogen atom],

(8) a group represented by the formula:
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[wherein ring B8 is a C_10-14aryl ring which may be further substituted, or an aromatic heterocycle which may be further substituted; Z⁸is C_1-6alkylene which may be substituted or a bond; R¹⁸is (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; and R¹⁹is (a) a hydrocarbon group which may be substituted, or (b) a heterocyclic group which may be substituted; or R¹⁸and R¹⁹may form a ring together with the adjacent nitrogen atom], or

(9) a group represented by the formula:
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[wherein ring B⁹is a C_6-14aryl ring which may be further substituted, or an aromatic heterocycle which may be further substituted, provided that when X is an oxygen atom, ring B⁹is not an indole ring; Z⁹is C_1-6alkylene which may be substituted or a bond; R²⁰is a hydrocarbon group which may be substituted, or a heterocyclic group which may be substituted; and n is an integer from 0 to 2]; or

Formula (1-b):
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wherein ring A is a 6-membered aromatic ring which may be further substituted,

R¹is a hydrocarbon group which may be substituted or a hydrogen atom,

R²¹and R²², which may be identical or different, are each a hydrocarbon group which may be substituted or a hydrogen atom, and

R²³is

(1) a group represented by the formula:
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[wherein ring B¹⁰is a benzene ring which may be further substituted; Z¹⁰is C_1-6alkylene which may be substituted or a bond; and R²⁴and R²⁵, which may be identical or different, are each (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; or R²⁴and R²⁵may form a ring together with the adjacent nitrogen atom],

(2) a group represented by the formula:
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[wherein ring B¹¹is a benzene ring which may be further substituted; Z¹¹is C_1-6alkylene which may be substituted or a bond; and R²⁶and R²⁷, which may be identical or different, are each (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; or R²⁶and R²⁷may form a ring together with the adjacent nitrogen atom],

(3) a group represented by the formula:
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[wherein ring B¹²is a benzene ring which may be further substituted; Z¹²is C_1-6alkylene which may be substituted or a bond; and R²⁸and R²⁹, which may be identical or different, are each (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; or R²⁸and R²⁹may form a ring together with the adjacent nitrogen atom],

(4) a group represented by the formula:
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[wherein ring B¹³is a benzene ring which may be further substituted; Z¹³is C_1-6alkylene which may be substituted or a bond; and R³⁰and R³¹, which may be identical or different, are each (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; or R³⁰and R³¹may form a ring together with the adjacent nitrogen atom],

(5) a group represented by the formula:
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[wherein ring B¹⁴is a benzene ring which may be further substituted; Z¹⁴is C_1-6alkylene which may be substituted or a bond; and R³²and R³³, which may be identical or different, are each (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; or R³²and R³³may form a ring together with the adjacent nitrogen atom],

(6) a group represented by the formula:
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[wherein ring B¹⁵is a benzene ring which may be further substituted; Z¹⁵is C_1-6alkylene which may be substituted or a bond; and R³⁴and R³⁵, which may be identical or different, are each (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; or R³⁴and R³⁵may form a ring together with the adjacent nitrogen atom],

(7) a group represented by the formula:
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[wherein ring B¹⁶is a C_10-14aryl ring which may be further substituted, or an aromatic heterocycle which may be further substituted; Z¹⁶is C_1-6alkylene which may be substituted or a bond; and R³⁶and R³⁷, which may be identical or different, are each (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; or R³⁶and R³⁷may form a ring together with the adjacent nitrogen atom],

(8) a group represented by the formula:
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[wherein ring B¹⁷is a C_10-14aryl ring which may be further substituted, or an aromatic heterocycle which may be further substituted; Z¹⁷is C_1-6alkylene which may be substituted or a bond; and R³⁸and R³⁹, which may be identical or different, are each (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; or R³⁸and R³⁹may form a ring together with the adjacent nitrogen atom], or

(9) a group represented by the formula:
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[wherein ring B¹⁸is a C_6-14aryl ring which may be further substituted, or an aromatic heterocycle which may be further substituted; Z18 is C_1-6alkylene which may be substituted or a bond; R⁴⁰is a hydrocarbon group which may be substituted, or a heterocyclic group which may be substituted; and n is an integer from 0 to 2, provided that the case where R²¹and R²²are each a hydrogen atom, ring B¹⁸is a thiazole ring, Z¹⁸is methylene, and n is 2, and the case where R²¹and R²²are each a dimethylaminophenyl, are excluded],

which is characterized in having a sulfonamide or amide, or thioether, sulfinyl or sulfonyl structure at the end of side chains, or a salt thereof. The inventors have also found for the first time that these compounds have unexpectedly excellent GnRH antagonizing activity, especially strong antagonist activity, based on their specific chemical structures, and that these compounds have very low toxicity and are sufficiently satisfactory as medicines having GnRH antagonizing activity, thus completing the invention based on these findings.

Thus, the invention relates to the following [1] through [31]:

[1] A gonadotropin releasing hormone antagonist which comprises a compound represented by the formula:
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wherein R^1ais a hydrocarbon group which may be substituted or a hydrogen atom,

ring A^ais a 6-membered aromatic ring which may be further substituted,

ring B^ais a homocyclic or heterocyclic ring which may be further substituted,

W^ais an oxygen atom or a sulfur atom,

X^a1and X^a2, which may be identical or different, are each a hydrogen atom, a hydrocarbon group which may be substituted or a heterocyclic group which may be substituted, or X^a1and X^a2together may form an oxygen atom, a sulfur atom or NR^3a(wherein R^3ais a hydrocarbon group which may be substituted or a hydrogen atom), and

Y^ais C_1-6alkylene which may be substituted or a bond, or a salt or prodrug thereof;

[2] The gonadotropin releasing hormone antagonist according to [1] above, wherein X^a1and X^a2together form an oxygen atom, a sulfur atom, or NR^3a(wherein R^3ais a hydrocarbon group which may be substituted or a hydrogen atom);

[3] The gonadotropin releasing hormone antagonist according to [1] or [2] above, which is a prophylactic and/or therapeutic agent for prostatomegaly, hysteromyoma, endometriosis, metrofibroma, precocious puberty, amenorrhea, premenstrual syndrome, dysmenorrhea, polycystic ovary syndrome, acne, baldness, Alzheimer's disease, infertility, irritable bowel syndrome, prostate cancer, uterine cancer, breast cancer or pituitary tumor, a reproduction regulator, a contraceptive, an ovulation inducing agent, or a preventive agent for post-operative recurrence of sex hormone-dependent cancers;

[4] A method for prevention and/or treatment of prostatomegaly, hysteromyoma, endometriosis, metrofibroma, precocious puberty, amenorrhea, premenstrual syndrome, dysmenorrhea, polycystic ovary syndrome, acne, baldness, Alzheimer's disease, infertility or irritable bowel syndrome, a lo method for reproduction regulation, a method for contraception, or a method for ovulation induction, which comprises administering an effective amount of a compound represented by the formula:
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wherein R^1ais a hydrocarbon group which may be substituted or a hydrogen atom,

ring A^ais a 6-membered aromatic ring which may be further substituted,

ring B^ais a homocyclic or heterocyclic ring which may be further substituted,

W^ais an oxygen atom or a sulfur atom,

Y^ais C_1-6alkylene which may be substituted or a bond, or a salt or prodrug thereof to a mammal;

[5] The method according to [4] above, wherein X^a1and X^a2together form an oxygen atom, a sulfur atom, or NR^3a(wherein R^3ais a hydrocarbon group which may be substituted or a hydrogen atom);

[6] Use of a compound represented by the formula:
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wherein R^1ais a hydrocarbon group which may be substituted or a hydrogen atom,

ring A^ais a 6-membered aromatic ring which may be further substituted,

ring B^ais a homocyclic or heterocyclic ring which may be further substituted,

W^ais an oxygen atom or a sulfur atom,

Y^ais C_1-6alkylene which may be substituted or a bond, or a salt or prodrug thereof for the manufacture of a prophylactic and/or therapeutic agent for prostatomegaly, hysteromyoma, endometriosis, metrofibroma, precocious puberty, amenorrhea, premenstrual syndrome, dysmenorrhea, polycystic ovary syndrome, acne, baldness, Alzheimer's disease, infertility or irritable bowel syndrome, a reproduction regulating agent, a contraceptive, or an ovulation inducing agent;

[7] The use according to [6] above, wherein X^a1and X^a2together form an oxygen atom, a sulfur atom or NR^3a(wherein R^3ais a hydrocarbon group which may be substituted or a hydrogen atom);

[8] A compound represented by Formula (I-a):
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wherein ring A is a 6-membered aromatic ring which may be further substituted,

X is an oxygen atom, a sulfur atom or NR³(wherein R³is a hydrocarbon group which may be substituted or a hydrogen atom),

R¹is a hydrocarbon group which may be substituted or a hydrogen atom, and

R²is

(1) a group represented by the formula:
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(2) a group represented by the formula:
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(3) a group represented by the formula:
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[wherein ring B³is a benzene ring which may be further substituted; Z³is C_1-6alkylene which may be substituted or a bond; R⁸is (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; and R⁹is (a) a hydrocarbon group which may be substituted, or (b) a heterocyclic group which may be substituted; or R⁸and R⁹may form a ring together with the adjacent nitrogen atom, provided that when R⁸is a hydrogen atom, R⁹is (a) an aryl group which may be substituted, (b) an aralkyl group which may be substituted, or (c) an alkyl group substituted with a heterocyclic group which may be substituted],

(4) a group represented by the formula:
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[wherein ring B⁴is a benzene ring which may be further substituted; Z⁴is C_1-6alkylene which may be substituted or a bond; R¹⁰is (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; and R¹¹is (a) an aromatic group which may be substituted, (b) an aralkyl group which may be substituted, or (c) an alkyl group substituted with a heterocyclic group which may be substituted; or R¹⁰and R¹¹together with the adjacent nitrogen atom may form a heterocyclic ring comprising carbon and nitrogen atoms as ring-constituting moieties],

(5) a group represented by the formula:
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(6) a group represented by the formula:
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(7) a group represented by the formula:
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(8) a group represented by the formula:
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[wherein ring B8 is a C_10-14aryl ring which may be further substituted, or an aromatic heterocycle which may be further substituted; Z⁸is C_1-6alkylene which may be substituted or a bond; R¹⁰is (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; and R¹⁹is (a) a hydrocarbon group which may be substituted, or (b) a heterocyclic group which may be substituted; or R¹⁸and R¹⁹may form a ring together with the adjacent nitrogen atom], or

(9) a group represented by the formula:
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[wherein ring B⁹is a C_6-14aryl ring which may be further substituted, or an aromatic heterocycle which may be further substituted, provided that when X is an oxygen atom, ring B⁹is not an indole ring; Z⁹is C_1-6alkylene which may be substituted or a bond; R²⁰is a hydrocarbon group which may be substituted, or a heterocyclic group which may be substituted; and n is an integer from 0 to 2]; or

Formula (I-b):
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wherein ring A is a 6-membered aromatic ring which may be further substituted,

R¹is a hydrocarbon group which may be substituted or a hydrogen atom,

R²¹and R²², which may be identical or different, are each a hydrocarbon group which may be substituted or-a hydrogen atom, and

R²³is

(1) a group represented by the formula:
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[wherein ring B¹⁰is a benzene ring which may be further substituted; Z¹⁹is C_1-6alkylene which may be substituted or a bond; and R²⁴and R²⁵, which may be identical or different, are each (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; or R²⁴and R²⁵may form a ring together with the adjacent nitrogen atom],

(2) a group represented by the formula:
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(3) a group represented by the formula:
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(4) a group represented by the formula:
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(5) a group represented by the formula:
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(6) a group represented by the formula:
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(7) a group represented by the formula:
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(8) a group represented by the formula:
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(9) a group represented by the formula:
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[wherein ring B¹⁸is a C_6-14aryl ring which may be further substituted, or an aromatic heterocycle which may be further substituted; Z¹⁸is C_1-6alkylene which may be substituted or a bond; R⁴⁰is a hydrocarbon group which may be substituted, or a heterocyclic group which may be substituted; and n is an integer from 0 to 2, provided that the case where R²¹and R²²are each a hydrogen atom, ring B¹⁸is a thiazole ring, Z¹⁸is methylene, and n is 2, and the case where R²¹and R²²are each dimethylaminophenyl, are excluded],

or a salt thereof;

provided that the following are excluded:

2-[2-(5-chloro-2,4-dioxo-1,2,3,4-tetrahydro-3-quinazolinyl)phenyl]-N-(1-naphthylmethyl)acetamide,

2-[3-(5-chloro-2,4-dioxo-1,2,3,4-tetrahydro-3-quinazolinyl)phenyl]-N-(1-naphthylmethyl)acetamide,

3-(5-chloro-2,4-dioxo-1,2,3,4-tetrahydro-3-quinazolinyl)-N-(1-naphthylmethyl)benzamide,

7-chloro-1-[4-(1,4-dihydro-2,4-dioxo-3(2H)-quinazolinyl)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine,

N,N-dibutyl-4-(1,4-dihydro-2,4-dioxo-3(2H)-quinazolinyl)benzenesulfonamide,

3,3′-(6,6′-sulfonyldibenzothiazole-2,2′-diyl)bis(2,4-dioxo-1,2,3,4-tetrahydroquinazoline),

N-[4-(benzyloxy)phenyl]-3-methoxy-4-(2-oxo-1,4-dihydroquinazolin-3(2H)-yl)benzamide, and

N-[4-(benzyloxy)phenyl]-4-(6,7-dimethoxy-2-oxo-1,4-dihydroquinazolin-3(2H)-yl)-3-methoxybenzamide;

[9] The compound according to [8] above, represented by the formula:
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wherein ring A is a 6-membered aromatic ring which may be further substituted,

X is an oxygen atom, a sulfur atom or NR³(wherein R³is a hydrocarbon group which may be substituted or a hydrogen atom),

R¹is a hydrocarbon group which may be substituted or a hydrogen atom, and

R²is

(1) a group represented by the formula:
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(2) a group represented by the formula:
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(3) a group represented by the formula:
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(4) a group represented by the formula:
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(5) a group represented by the formula:
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(6) a group represented by the formula:
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(7) a group represented by the formula:
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(8) a group represented by the formula:
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7-chloro-1-[4-(1,4-dihydro-2,4-dioxo-3(2H)-quinazolinyl)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine, and

N,N-dibutyl-4-(1,4-dihydro-2,4-dioxo-3(2H)-quinazolinyl)benzenesulfonamide;

[10] The compound according to [8] or [9] above, wherein

R¹is (1) a hydrogen atom, or (2) C_1-6alkyl which may be substituted with 1 to 3 substituents selected from (a) C_6-14aryl which may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen, (b) cyano, (c) hydroxy, (d) carboxy, (e) nitro, (f) C_1-6alkyl which may be substituted with di-C_1-6alkylamino, (g) C_1-6alkoxy, (h) C_1-6alkyl-carbonyloxy, (i) C_1-6alkylthio, (j) C_1-6alkylsulfinyl, (k) C_1-6alkylsulfonyl, (l) halogen, (m) amino, (n) mono-C_1-6alkylamino, (o) di-C_1-6alkylamino, (p) a 5-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5-membered ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (q) a 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 6-membered ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (r) a bicyclic or tricyclic fused ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this bicyclic or tricyclic fused ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (s) C_1-6alkoxycarbonyl, (t) carbamoyl, (u) N-mono-C_1-6alkylcarbamoyl, (v) N,N-di-C_1-6alkylcarbamoyl, and (w) C_1-2alkylenedioxy;

[11] The compound according to [8] or [9] above, wherein X is an oxygen atom or NR³(wherein R³is (1) a hydrogen atom, (2) C_1-6alkyl which may be substituted with 1 to 3 substituents selected from (a) C_6-14aryl which may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen, (b) cyano, (c) hydroxy, (d) carboxy, (e) nitro, (f) C_1-6alkyl which may be substituted with di-C_1-6alkylamino, (g) C_1-6alkoxy, (h) C_1-6alkyl-carbonyloxy, (i) C_1-6alkylthio, (j) C_1-6alkylsulfinyl, (k) C_1-6alkylsulfonyl, (l) halogen, (m) amino, (n) mono-C_1-6alkylamino, (o) di-C_1-6alkylamino, (p) a 5-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5-membered ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (q) a 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 6-membered ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (r) a bicyclic or tricyclic fused ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this bicyclic or tricyclic fused ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (s) C_1-6alkoxycarbonyl, (t) carbamoyl, (u) N-mono-C_1-6alkylcarbamoyl, (v) N,N-di-C_1-6alkylcarbamoyl, and (w) C_1-2alkylenedioxy (hereinafter (a)-(w) are briefly referred to as Substituent Group A), (3) C_2-6alkenyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (4) C_2-6alkynyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (5) C_3-8cycloalkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (6) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (7) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A);

[12] The compound according to [8] above, wherein ring A is a benzene ring substituted with one substituent selected from (a) hydroxy, (b) cyano, (c) carboxyl, (d) mono- or dialkylcarbamoyl, (e) acylamino, (f) alkylamino, and (g) alkoxycarbonyl, or a benzene ring substituted with a hydrocarbon group substituted with a substituent selected from the above substituent groups;

[13] The compound according to [8] above, wherein ring B², ring B⁵, ring B¹¹and ring B¹⁴, which may be identical or different, are each a benzene ring which may be further substituted with 1 to 3 substituents selected from (a) C_6-14aryl which may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen, (b) cyano, (c) hydroxy, (d) carboxy, (e) nitro, (f) C_1-6alkyl which may be substituted with di-C_1-6alkylamino, (g) C_1-6alkoxy, (h) C_1-6alkylcarbonyloxy, (i) C_1-6alkylthio, (j) C_1-6alkylsulfinyl, (k) C_1-6alkylsulfonyl, (l) halogen, (m) amino, (n) mono-C_1-6alkylamino, (o) di-C_1-6alkylamino, (p) a 5-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5-membered ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (q) a 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 6-membered ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (r) a bicyclic or tricyclic fused ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this bicyclic or tricyclic fused ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (s) C_1-6alkoxycarbonyl, (t) carbamoyl, (u) N-mono-C_1-6alkylcarbamoyl, (v) N,N-di-C_1-6alkylcarbamoyl, and (w) C₁₂alkylenedioxy (hereinafter (a)-(w) are briefly referred to as Substituent Group A);

ring B⁷, ring B⁸, ring B¹⁶and ring B¹⁷, which may be identical or different, are each an aromatic heterocycle which may be further substituted with 1 to 3 substituents selected from the Substituent Group A;

Z², Z⁵, Z⁷, Z⁸, Z¹¹, Z¹⁴, Z¹⁶and Z¹⁷, which may be identical or different, are each C_1-6alkylene which may be substituted or a bond;

R⁶, R¹², R¹⁶, R¹⁸, R²⁶, R³², R³⁶and R³⁸, which may be identical or different, are each (a) a hydrogen atom, (b) C_1-6alkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (c) C_2-6alkenyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (d) C_2-6alkynyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (e) C_3-8cycloalkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (f) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (g) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (h) a 5- or 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A), provided that R¹²is not a hydrogen atom; and

R⁷, R¹³, R¹⁷, R¹⁹, R²⁷, R³³, R³⁷and R³⁹, which may be identical or different, are each (a) C_1-10alkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (b) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (c) a 5- or 6-membered aromatic ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); or

R⁶and R⁷, R¹²and R¹³, R¹⁶and R¹⁷, R¹⁸and R¹⁹, R²⁶and R²⁷, R³²and R³³, R³⁶and R³⁷, and R³⁸and R³⁹may respectively form a ring together with the adjacent nitrogen atom;

[14] The compound according to [8] above, wherein ring A is a benzene ring, X is an oxygen atom or NH, R¹is a hydrogen atom or C_1-6alkyl;

ring B², ring B⁵, ring B¹¹and ring B¹⁴, which may be identical or different, are each a benzene ring which may be further substituted with one substituent selected from halogen, lower alkyl and cyano;

ring B⁷, ring B⁸, ring B¹⁶and ring B¹⁷, which may be identical or different, are each a thiophene ring or a furan ring which may be further substituted;

Z², Z⁵, Z⁷, Z⁸, Z¹¹, Z¹⁴, Z¹⁶and Z¹⁷, which may be identical or different, are each C_1-6alkylene which may be substituted or a bond;

R⁶, R¹², R¹⁶, R¹⁸, R²⁶, R³², R³⁶and R³⁸, which may be identical or different, are each C_1-6alkyl which may be substituted with cyano; and

R⁶and R⁷, R¹²and R¹³, R¹⁶and R¹⁷, R¹⁸and R¹⁹, R²⁶and R²⁷, R³²and R³³, R³⁶and R³⁷, and R³⁸and R³⁹may respectively form, together with the adjacent nitrogen atom, (1) 1,2,3,4-tetrahydroquinolin-1-yl which may be substituted with C_1-6alkyl, halogen or C_1-6alkoxy, (2) 2,3-dihydro-1H-indol-1-yl which may be substituted with C_1-6alkyl, (3) 2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl which may be substituted with C_1-6alkyl, or (4) 3,4-dihydro-2H-1,4-benzoxazin-1-yl;

[15] The compound according to [13] or [14] above, wherein Z², Z⁵, Z⁷, Z⁸, Z¹¹, Z¹⁴, Z¹⁶and Z¹⁷are each a bond;

[16] The compound according to [9] above, wherein R²is

(1) a group represented by the formula:
embedded image

[wherein ring B²′ is a benzene ring which may be further substituted with 1 to 3 substituents selected from (a) C_6-14aryl which may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen, (b) cyano, (c) hydroxy, (d) carboxy, (e) nitro, (f) C_1-6alkyl which may be substituted with di-C_1-6alkylamino, (g) C_1-6alkoxy, (h) C_1-6alkyl-carbonyloxy, (i) C_1-6alkylthio, (j) C_1-6alkylsulfinyl, (k) C_1-6alkylsulfonyl, (l) halogen, (m) amino, (n) mono-C_1-6alkylamino, (o) di-C_1-6alkylamino, (p) a 5-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5-membered ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (q) a 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 6-membered ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (r) a bicyclic or tricyclic fused ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this bicyclic or tricyclic fused ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (s) C_1-6alkoxycarbonyl, (t) carbamoyl, (u) N-mono-C_1-6alkylcarbamoyl, (v) N,N-di-C_1-6alkylcarbamoyl, and (w) C_1-2alkylenedioxy (hereinafter (a)-(w) are briefly referred to as Substituent Group A);

R⁶′ is (a) a hydrogen atom, (b) C_1-6alkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (c) C_2-6alkenyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (d) C_2-6alkynyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (e) C_3-8cycloalkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (f) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (g) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (h) a 5- or 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); and

R⁷′ is (a) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (b) a 5- or 6-membered aromatic ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); or

R⁶′ and R⁷′ may form a ring together with the adjacent nitrogen atom],

(2) a group represented by the formula:
embedded image

[wherein ring B⁵′ is a benzene ring which may be further substituted with 1 to 3 substituents selected from the Substituent Group A;

R¹²′ is (a) C_1-6alkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (b) C_2-6alkenyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (c) C_2-6alkynyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (d) C_3-8cycloalkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (e) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (f) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (g) a 5- or 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); and

R¹³′ is (a) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (b) a 5- or 6-membered aromatic ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); or

R¹²′ and R¹³′ may form a ring together with the adjacent nitrogen atom], or

(3) a group represented by the formula:
embedded image

[wherein ring B⁷′ is an aromatic heterocycle which may be further substituted with 1 to 3 substituents selected from the Substituent Group A;

R¹⁶′ is (a) a hydrogen atom, (b) C_1-6alkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (c) C_2-6alkenyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (d) C_2-6alkynyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (e) C_3-8cycloalkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (f) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (g) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (h) a 5- or 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); and

R¹⁷′ is (a) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (b) a 5- or 6-membered aromatic ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); or

R¹⁶′ and R¹⁷′ may form a ring together with the adjacent nitrogen atom);

[17] The compound according to [9] above, wherein ring A is a benzene ring, X is an oxygen atom or NH, R¹is a hydrogen atom or C_1-6alkyl, and R²is

(1) a group represented by the formula:
embedded image

[wherein ring B²″ is a benzene ring which may be further substituted with halogen, R⁶″ is C_1-6alkyl which may be substituted with cyano, and R⁷″ is C_6-14aryl or pyridyl which may be substituted with halogen, or R⁶″ and R⁷″ form, together with the adjacent nitrogen atom, (1) 1,2,3,4-tetrahydroquinolin-1-yl which may be substituted with C_1-6alkyl, halogen or C_1-6alkoxy, (2) 2,3-dihydro-1H-indol-1-yl which may be substituted with C_1-6alkyl, (3) 2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl which may be substituted with C_1-6alkyl, or (4) 3,4-dihydro-2H-1,4-benzoxazin-1-yl];

(2) a group represented by the formula:
embedded image

[wherein ring B⁵″ is a benzene ring which may be further substituted with halogen, R¹²″ is C_1-6alkyl which may be substituted with cyano, and R¹³″ is C_6-14aryl or pyridyl which may be substituted with halogen, or R¹²″ and R¹³″ form, together with the adjacent nitrogen atom, (1) 1,2,3,4-tetrahydroquinolin-1-yl which may be substituted with C_1-6alkyl, halogen or C_1-6alkoxy, (2) 2,3-dihydro-1H-indol-1-yl which may be substituted with C_1-6alkyl, (3) 2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl which may be substituted with C_1-6alkyl, or (4) 3,4-dihydro-2H-1,4-benzoxazin-1-yl]; or

(3) a group represented by the formula:
embedded image

[wherein ring B⁷″ is a thiophene ring which may be further substituted with halogen, R¹⁶″ is C_1-6alkyl which may be substituted with cyano, and R¹⁷″ is C_6-14aryl or pyridyl which may be substituted with halogen, or R¹⁶″ and R¹⁷″ form, together with the adjacent nitrogen atom, (1) 1,2,3,4-tetrahydroquinolin-1-yl which may be substituted with C_1-6alkyl, halogen or C_1-6alkoxy, (2) 2,3-dihydro-1H-indol-1-yl which may be substituted with C_1-6alkyl, (3) 2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl which may be substituted with C_1-6alkyl, or (4) 3,4-dihydro-2H-1,4-benzoxazin-1-yl];

[18] 3-(2-chloro-5-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)phenyl)quinazoline-2,4(1H,3H)-dione,

4-chloro-3-(2,4-dioxo-1,4-dihydro-3(2H)-quinazolinyl)-N-methyl-N-2-pyridinylbenzenesulfonamide trifluoroacetate,

3-(2-chloro-5-(2,3,4,5-tetrahydro-1H-1-benzazepin-1-ylsulfonyl)phenyl)-2,4(1H,3H)-quinazolinedione,

3-(2-chloro-5-(3,4-dihydro-1,5-benzoxazepin-5(2H)-ylsulfonyl)phenyl)-2,4(1H,3H)-quinazolinedione,

4-chloro-3-(4-imino-2-oxo-1,4-dihydro-3(2H)-quinazolinyl)-N-methyl-N-phenylbenzenesulfonamide trifluoroacetate, or

3-(2-chloro-5-(3,4-dihydro-1(2H)-quinolinylsulfonyl)phenyl)-4-imino-3,4-dihydro-2(1H)-quinazolinone trifluoroacetate;

[19] 3-[5-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)-2-fluorophenyl]quinazoline-2,4(1H,3H)-dione,

3-[2-chloro-5-(5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepin-4-ylsulfonyl)phenyl]quinazoline-2,4(1H,3H)-dione,

4-chloro-3-(2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl)-N-methyl-N-phenylbenzamide,

5-chloro-4-[5-(hydroxymethyl)-2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl]-N-methyl-N-phenylthiophene-2-carboxamide,

Methyl 3-[2-chloro-5-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)phenyl]-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-5-carboxylate,

3-[2-chloro-5-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)phenyl]-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-5-carboxylic acid,

3-[2-chloro-5-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)phenyl]-5-(hydroxymethyl)quinazoline-2,4(1H,3H)-dione,

3-(2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl)-5-(2,3,4,5-tetrahydro-1H-1-benzazepin-1-ylsulfonyl)thiophene-2-carbonitrile,

4-chloro-3-[5-(hydroxymethyl)-2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl]-N-methyl-N-phenylbenzamide,

4-chloro-3-[5-(hydroxymethyl)-2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl]-N-methyl-N-pyridin-2-ylbenzamide,

3-[2-chloro-5-(2,3,4,5-tetrahydro-1H-1-benzazepin-1-ylsulfonyl)-3-thienyl]-5-(hydroxymethyl)quinazoline-2,4(1H,3H)-dione,

5-chloro-N-cyclohexyl-4-[5-(hydroxymethyl)-2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl]-N-methylthiophene-2-carboxamide,

5-chloro-N-(2-chlorophenyl)-4-[5-(hydroxymethyl)-2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl]-N-methylthiophene-2-carboxamide,

5-chloro-N-(3-chlorophenyl)-4-[5-(hydroxymethyl)-2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl]-N-methylthiophene-2-carboxamide,

5-chloro-N-(4-chlorophenyl)-4-[5-(hydroxymethyl)-2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl]-N-methylthiophene-2-carboxamide,

5-chloro-4-[5-(hydroxymethyl)-2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl]-N-methyl-N-(2-methylphenyl)thiophene-2-carboxamide,

5-chloro-4-[5-(hydroxymethyl)-2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl]-N-methyl-N-(3-methylphenyl)thiophene-2-carboxamide,

3-[2-chloro-5-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)phenyl]-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-5-carboxamide,

3-[2-chloro-5-(3,4-dihydroquinolin-1(2H) -ylsulfonyl)phenyl]-3,4-dihydroquinazolin-2(1H) -one,

3-[2-chloro-5-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)phenyl]-2-oxo-1,2,3,4-tetrahydroquinazoline-5-carboxylic acid,

5-chloro-4-[5-(hydroxymethyl)-2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl]-N-isobutyl-N-methylthiophene-2-carboxamide, or

3-[2-chloro-5-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)phenyl]-5-(1-hydroxy-1-methylethyl)quinazoline-2,4(1H,3H)-dione;

[20] A prodrug of the compound according to [8] or [9] above;

[21] A medicine which comprises the compound according to [8] or [9] above, or a prodrug thereof;

[22] A prophylactic and/or therapeutic agent for sex hormone-dependent diseases, containing the compound according to [8] above or a prodrug thereof;

[23] A prophylactic and/or therapeutic agent for prostatomegaly, hysteromyoma, endometriosis, metrofibroma, precocious puberty, amenorrhea, premenstrual syndrome, dysmenorrhea, polycystic ovary syndrome, acne, baldness, Alzheimer's disease, infertility, irritable bowel syndrome, prostate cancer, uterine cancer, breast cancer or pituitary tumor, a reproduction regulator, a contraceptive, an ovulation inducing agent, or a preventive agent for post-operative recurrence of sex hormone-dependent cancers, which contains the compound according to [8] above or a prodrug thereof;

[24] A prophylactic and/or therapeutic agent for prostate cancer, uterine cancer, breast cancer or pituitary tumor, or a preventive agent for post-operative recurrence of sex hormone-dependent cancers, which contains the compound according to [8] or [9] above, or a prodrug thereof;

[25] A method for prevention and/or treatment of prostatomegaly, hysteromyoma, endometriosis, metrofibroma, precocious puberty, amenorrhea, premenstrual syndrome, dysmenorrhea, polycystic ovary syndrome, acne, baldness, Alzheimer's disease, infertility, irritable bowel syndrome, prostate cancer, uterine cancer, breast cancer or pituitary tumor, a method for reproduction regulation, a method for contraception, a method for ovulation induction, or a method for prevention of post-operative recurrence of sex hormone-dependent cancers, which comprises administering an effective amount of the compound according to [8] above or a prodrug thereof to a mammal;

[26] A method for prevention and/or treatment of prostate cancer, uterine cancer, breast cancer or pituitary tumor, or a method for prevention of post-operative recurrence of sex hormone-dependent cancers, which comprises administering an effective amount of the compound according to [8] or [9], or a prodrug thereof to a mammal;

[27] Use of the compound according to [8] above or a prodrug thereof for the manufacture of a prophylactic and/or therapeutic agent for prostatomegaly, hysteromyoma, endometriosis, metrofibroma, precocious puberty, amenorrhea, premenstrual syndrome, dysmenorrhea, polycystic ovary syndrome, acne, baldness, Alzheimer's disease, infertility, irritable s bowel syndrome, prostate cancer, uterine cancer, breast cancer or pituitary tumor, a reproduction regulator, a contraceptive, an ovulation inducing agent, or a preventive agent for post-operative recurrence of sex hormone-dependent cancers;

[28] Use of the compound according to [8] or [9] above, or a prodrug thereof for the manufacture of a prophylactic and/or therapeutic agent for prostate cancer, uterine cancer, breast cancer or pituitary tumor, or a preventive agent for post-operative recurrence of sex hormone-dependent cancers;

[29] The compound according to [9] above, wherein ring A is (1) a benzene ring which may be substituted with 1 to 4 substituents selected from (a) C_6-14aryl which may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen, (b) cyano, (c) hydroxy, (d) 2o carboxyl, (e) nitro, (f) C_1-6alkyl which may be substituted with di-C_1-6alkylamino, (g) C_1-6alkoxy, (h) C_1-6alkylcarbonyloxy, (i) C_1-6alkylthio, (j) C_1-6alkylsulfinyl, (k) C_1-6alkylsulfonyl, (l) halogen, (m) amino, (n) mono-C_1-6alkylamino, (o) di-C_1-6alkylamino, (p) a 5-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5-membered ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and 30 (vi) halogen), (q) a 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 6-membered ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (r) a bicyclic or tricyclic fused ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this bicyclic or tricyclic fused ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (s) C_1-6alkoxycarbonyl, (t) carbamoyl, (u) N-mono-C_1-6alkylcarbamoyl, (v) N,N-di-C_1-6alkylcarbamoyl, and (w) C_1-2alkylenedioxy (hereinafter (a)-(w) are briefly referred to as Substituent Group A), (2) a pyridine ring which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (3) a pyrazine ring which may be substituted with 1 or 2 substituents selected from the Substituent Group A, (4) a pyrimidine ring which may be substituted with 1 or 2 substituents selected from the Substituent Group A, or (5) a pyridazine ring which may be substituted with 1 or 2 substituents selected from the Substituent Group A;

X is an oxygen atom, a sulfur atom or NR³(wherein R³is (1) a hydrogen atom, (2) C_1-6alkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (3) C_2-6alkenyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (4) C_2-6alkynyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (5) C_3-8cycloalkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (6) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (7) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A);

R¹is (1) a hydrogen atom, (2) C_1-6alkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (3) C_2-6alkenyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (4) C_2-6alkynyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (5) C_3-8cycloalkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (6) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (7) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A;

R²is (1) a group represented by the formula:
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[wherein ring B¹is a benzene ring which may be further substituted with 1 to 3 substituents selected from the Substituent Group A; Z¹is C_1-6alkylene which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or a bond; R⁴is (a) a hydrogen atom, (b) C_1-6alkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (C) C_2-6alkenyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (d) C_2-6alkynyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (e) C_3-8cycloalkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (f) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (g) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (h) a 5- or 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); and R⁵is (a) C_1-6alkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (b) C_2-6alkenyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (C) C_2-6alkynyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (d) C_3-8cycloalkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (e) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (f) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (g) a 5- or 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring group may be substituted lo with a substituent selected from the Substituent Group A); or R⁴and R⁵may form a ring together with the adjacent nitrogen atom],

(2) a group represented by the formula:
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[wherein ring B²is a benzene ring which may be further substituted with 1 to 3 substituents selected from the Substituent Group A; Z²is C_1-6alkylene which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or a bond; R⁶is (a) a hydrogen atom, (b) C_1-6alkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (c) C_2-6alkenyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (d) C_2-6alkynyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (e) C_3-8cycloalkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (f) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (g) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (h) a 5- or 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); and R⁷is (a) C_1-6alkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (b) C_2-6alkenyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (c) C_2-6alkynyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (d) C_3-8cycloalkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (e) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (f) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (g) a 5- or 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); or R⁶and R⁷may form a ring together with the adjacent nitrogen atom],

(3) a group represented by the formula:
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[wherein ring B³is a benzene ring which may be further substituted with 1 to 3 substituents selected from the Substituent Group A; Z³is C_1-6alkylene which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or a bond; R⁸is (a) a hydrogen atom, (b) C_1-6alkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (c) C_2-6alkenyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (d) C_2-6alkynyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (e) C_3-8cycloalkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (f) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (g) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (h) a 5- or 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); and R⁹is (a) C_1-6alkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (b) C_2-6alkenyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (c) C_2-6alkynyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (d) C_3-8cycloalkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (e) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (f) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (g) a 5- or 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); or R⁸and R⁹may form a ring together with the adjacent nitrogen atom, provided that when R⁸is a hydrogen atom, R⁹is (a) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (b) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (c) C_1-6alkyl substituted with a heterocyclic group selected from (i) a 5-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms, (ii) a 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms, and (iii) a bicyclic or tricyclic fused ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this heterocyclic group may be substituted with 1 to 3 substituents selected from (i′) hydroxy, (ii′) amino, (iii′) mono-C_1-6alkylamino, (iv′) di-C_1-6alkylamino, (v′) C_1-6alkoxy, and (vi′) halogen)],

(4) a group represented by the formula:
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[wherein ring B⁴is a benzene ring which may be further substituted with 1 to 3 substituents selected from the Substituent Group A; Z⁴is C_1-6alkylene which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or a bond; R¹⁰is (a) a hydrogen atom, (b) C_1-6alkyl which may be substituted with 1 to 3 substituents is selected from the Substituent Group A, (c) C_2-6alkenyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (d) C_2-6alkynyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (e) C_3-8cycloalkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (f) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (g) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (h) a 5- or 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); and R¹¹is (a) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (b) a 5- or 6-membered aromatic ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituents from the Substituent Group A), (c) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (d) C_1-6alkyl substituted with a heterocyclic group selected from (i) a 5-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms, (ii) a 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms, and (iii) a bicyclic or tricyclic fused ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this heterocyclic group may be substituted with 1 to 3 substituents selected from (i′) hydroxy, (ii′) amino, (iii′) mono-C_1-6alkylamino, (iv′) di-C_1-6alkylamino, (v′) C_1-6alkoxy, and (vi′) halogen); or R¹⁰and R¹¹may form, together with the adjacent nitrogen atom, a heterocyclic ring comprising carbon and nitrogen atoms as ring-constituting moieties],

(5) a group represented by the formula:
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[wherein ring B⁵is a benzene ring which may be further substituted with 1 to 3 substituents selected from the Substituent Group A; Z⁵is C_1-6alkylene which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or a bond; and R¹²and R¹³, which may be identical or different, are each (a) a hydrogen atom, (b) C_1-6alkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (c) C_2-6alkenyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (d) C_2-6alkynyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (e) C_3-8cycloalkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (f) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (g) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (h) a 5- or 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); or R¹²and R¹³may form a ring together with the adjacent nitrogen atom],

(6) a group represented by the formula:
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[wherein ring B⁶is a benzene ring which may be further substituted with 1 to 3 substituents selected from the Substituent Group A; Z⁶is C_1-6alkylene which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or a bond; and R¹⁴and R¹⁵, which may be identical or different, are each (a) C_1-6alkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (b) C_2-6alkenyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (c) C_2-6alkynyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (d) C_3-8cycloalkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (e) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (f) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (g) a 5- or 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); or R¹⁴and R¹⁵may form a ring together with the adjacent nitrogen atom],

(7) a group represented by the formula:
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[wherein ring B⁷is a C_10-14aryl ring which may be further substituted with 1 to 3 substituents selected from the Substituent Group A, or an aromatic heterocycle which may be further substituted with 1 to 3 substituents selected from the Substituent Group A; Z⁷is C_1-6alkylene which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or a bond; R¹⁶is (a) a hydrogen atom, (b) C_1-6alkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (c) C_2-6alkenyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (d) C_2-6alkynyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (e) C_3-8cycloalkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (f) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (g) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (h) a 5- or 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); and R¹⁷is (a) C_1-6alkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (b) C_2-6alkenyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (c) C_2-6alkynyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (d) C_3-8cycloalkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (e) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (f) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (g) a 5- or 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); or R¹⁶and R¹⁷may form a ring together with the adjacent nitrogen atom], or

(8) a group represented by the formula:
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[wherein ring B⁸is a C_10-14aryl ring which may be further substituted with 1 to 3 substituents selected from the Substituent Group A, or an aromatic heterocycle which may be further substituted with 1 to 3 substituents selected from the Substituent Group A; Z⁸is C_1-6alkylene which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or a bond; R¹⁸is (a) a hydrogen atom, (b) C_1-6alkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (c) C_2-6alkenyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (d) C_2-6alkynyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (e) C_3-8cycloalkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (f) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (g) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (h) a 5- or 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); and R¹⁹is (a) C_1-6alkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (b) C_2-6alkenyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (c) C_2-6alkynyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (d) C_3-8cycloalkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (e) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (f) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (g) a 5- or 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); or R¹⁸and R¹⁹may form a ring together with the adjacent nitrogen atom];

[30] The compound according to [9] above, wherein ring A is a benzene ring which may be substituted with 1 to 4 substituents selected from the Substituent Group A; and

[31] The compound according to [9] above, wherein R²is

(1) a group represented by the formula:
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(2) a group represented by the formula:
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(3) a group represented by the formula:
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DETAILED EXPLANATION OF THE INVENTION

The compound of the invention has an excellent antagonistic activity against gonadotropin releasing hormone. Furthermore, the compound exhibits good oral absorption and is excellent in the aspects of stability and pharmacokinetics. It also has low toxicity and is excellent in view of safety. Therefore, the compound can be used as, for example, a prophylactic or therapeutic agent for hormone-dependent diseases. Specifically, the compound is effective as a medicine such as a prophylactic or therapeutic agent for sex hormone-dependent cancers (e.g., prostate cancer, uterine cancer, breast cancer, pituitary tumor, etc.), prostatomegaly, hysteromyoma, endometriosis, metrofibroma, precocious puberty, amenorrhea (syndrome), premenstrual syndrome, dysmenorrhea, polycystic ovary syndrome, acne, baldness, Alzheimer's disease and the like, or as a reproduction regulator, a birth control agent (e.g., a contraceptive (agent), an ovulation inducing agent, etc.), a prophylactic or therapeutic agent for infertility, a menstrual regulator, a prophylactic and/or therapeutic agent for irritable bowel syndrome, or a preventive agent for post-operative recurrence of sex hormone-dependent cancers. It is also effective as an agent for regulation of animal's estrus, improvement in the table meat quality or regulation of animal growth in the field of stockbreeding, or as a promoting agent for fish spawning in the field of fishery.

BEST MODE FOR CARRYING OUT THE INVENTION

In Compound (I), ring A is “a 6-membered aromatic ring which may be further substituted.” The “6-membered aromatic ring” of the “6-membered aromatic ring which may be further substituted” refers to a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring or the like. Specifically, Compound (I) is a compound represented by the formulas:
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wherein ring A¹through ring A¹¹may be substituted, and other reference symbols have the meanings as defined above.

Examples of the substituent which may be further carried by ring A include:

(a) cyano,

(b) hydroxy which may be protected by a protective group (e.g., tert-butyl(dimethyl)silyl [TBDMS], etc.),

(d) nitro,

(e) a hydrocarbon group

[wherein the hydrocarbon group may be exemplified by a hydrocarbon group having 1 to 20 carbon atoms such as an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an aralkyl group or an aryl group.

The “alkyl group” that can be used may be exemplified by a “straight-chained or branched C_1-15alkyl group” such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, tridecyl, tetradecyl or pentadecyl. Preferably, the “alkyl group” is C_1-6alkyl (e.g., methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, etc.).

The “cycloalkyl group” that can be used may be exemplified by a “C_3-8cycloalkyl group” such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.

The “alkenyl group” that can be used may be exemplified by a “C_2-18alkenyl group” such as vinyl, allyl, isopropenyl, 3-butenyl, 3-octenyl or 9-octadecenyl.

The “cycloalkenyl group” that can be used may be exemplified by a “C_3-8cycloalkenyl group” such as cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl or cyclooctenyl.

The “alkynyl group” that can be used may be exemplified by a “C_2-18alkynyl group” such as ethynyl, propynyl, 1-butynyl, 2-butynyl, 1-pentynyl, 2-pentynyl or 3-pentynyl.

The “aralkyl group” may be exemplified by C_7-14aralkyl, for example, a phenyl-C_1-6alkyl group such as benzyl, phenethyl, 3-phenylpropyl or 4-phenylbutyl, and a naphthyl-C_1-6alkyl group such as (1-naphthyl)methyl, 2-(1-naphthyl)ethyl or 2-(2-naphthyl)ethyl.

The “aryl group” that can be used may be exemplified by an aromatic monocyclic, bicyclic or tricyclic C_6-14aryl group such as phenyl, 1-naphthyl, 2-naphthyl, phenanthryl or anthryl.],

(f) C_1-6alkoxy (e.g., methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, etc.),

(g) C_6-14aryloxy (e.g., phenyloxy, 1-naphthyloxy, 2-naphthyloxy, phenanthryloxy, anthryloxy, etc.),

(h) heterocyclic oxy

[wherein the heterocyclic ring bound to the oxy may be exemplified by an aromatic heterocycle or a non-aromatic heterocycle.

The aromatic heterocycle may be exemplified by a 5- to 7-membered monocyclic aromatic heterocycle or fused aromatic heterocycle containing 1 to 4 heteroatoms selected from oxygen, s sulfur and nitrogen atoms in addition to carbon atoms, as the ring-constituting atom. The fused aromatic heterocycle may be exemplified by a ring in which one of these 5- to 7-membered monocyclic aromatic heterocycles is fused with a 6-membered ring containing 1 or 2 nitrogen atoms, a benzene ring or a 5-membered ring containing 1 sulfur atom, or the like. Suitable examples of the aromatic heterocycle include furan, thiophene, pyridine, pyrimidine, pyridazine, pyrazine, pyrrole, imidazole, pyrazole, isoxazole, isothiazole, oxazole, thiazole, oxadiazole, thiadiazole, triazole, tetrazole, quinoline, quinazoline, quinoxaline, benzofuran, benzothiophene, benzoxazole, benzothiazole, benzimidazole, indole, 1H-indazole, 1H-pyrrolo[2,3-b]pyrazine, 1H-pyrrolopyridine, 1H-imidazopyridine, 1H-imidazopyrazine, triazine, isoquinoline, benzothiadiazole and the like. The aromatic heterocycle is preferably a 5- or 6-membered aromatic heterocycle, and more preferably furan, thiophene, pyridine, pyrimidine, pyrazole, oxazole, thiazole or the like.

The non-aromatic heterocycle may be exemplified by a 5- to 7-membered monocyclic non-aromatic heterocycle or fused non-aromatic heterocycle containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms in addition to carbon atoms as the ring-constituting atom. The non-aromatic fused heterocyclic ring may be exemplified by a ring in which one of these 5- to 7-membered monocyclic non-aromatic heterocycles is fused with a 6-membered ring containing 1 or 2 nitrogen atom, a benzene ring or a 5-membered ring containing 1 sulfur atom, or the like. Suitable examples of the non-aromatic heterocycle include pyrrolidine, pyrroline, pyrazolidine, piperidine, piperazine, morpholine, thiomorpholine, piperazine, hexamethyleneimine, oxazolidine, thiazolidine, imidazolidine, imidazoline, tetrahydrofuran, azepane, tetrahydropyridine and the like.],

(i) C_1-6alkyl-carbonyloxy (e.g., methylcarbonyloxy, ethylcarbonyloxy, propylcarbonyloxy, isopropylcarbonyloxy, butylcarbonyloxy, isobutylcarbonyloxy, sec-butylcarbonyloxy, tert-butylcarbonyloxy, pentylcarbonyloxy, hexylcarbonyloxy, etc.),

(j) C_1-6alkylthio (e.g., methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, sec-butylthio, tert-butylthio, pentylthio, hexylthio, etc.),

(k) C_6-14arylthio (e.g., phenylthio, 1-naphthylthio, 2-naphthylthio, phenanthrylthio, anthrylthio, etc.),

(l) heterocyclic thio

[wherein the heterocyclic ring bound to the thio may be exemplified by the heterocyclic rings listed for the heterocyclic rings bound to the oxy in the above-described “heterocyclic oxy”],

(m) C_1-6alkylsulfinyl (e.g., methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl, pentylsulfinyl, hexylsulfinyl, etc.),

(n) C_6-14arylsulfinyl (e.g., phenylsulfinyl, 1-naphthylsulfinyl, 2-naphthylsulfinyl, phenanthrylsulfinyl, anthrylsulfinyl, etc.),

(o) heterocyclic sulfinyl

[wherein the heterocyclic ring bound to the sulfinyl may be exemplified by the heterocyclic rings listed for the heterocyclic rings bound to the oxy in the above-described “heterocyclic oxy”],

(p) C_1-6alkylsulfonyl (e.g., methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl, pentylsulfonyl, hexylsulfonyl, etc.),

(q) C_6-14arylsulfonyl (e.g., phenylsulfonyl, 1-naphthylsulfonyl, 2-naphthylsulfonyl, phenanthrylsulfonyl, anthrylsulfonyl, etc.),

(r) heterocyclic sulfonyl

[wherein the heterocyclic ring bound to the sulfonyl may be exemplified by the heterocyclic rings listed for the heterocyclic rings bound to the oxy in the above-described. “heterocyclic oxy”],

(s) halogen (e.g., fluorine, chlorine, bromine, iodine, etc.),

(t) amino which may be protected by C_1-20acyl (when the amino is protected by an acyl, it may be briefly referred to as C_1-20acylamino)

[wherein the “C_1-20acyl” that can be used may be exemplified by a C_1-20acyl group obtained by removing an OH group from a carboxylic acid such as R¹′COOH or R¹′OCOOH, a sulfonic acid such as R¹′SO₃H, a sulfinic acid such as R¹′SO₂H, a carbamic acid such as R¹′N(R²′)COOH (wherein R¹′is a hydrogen atom, a hydrocarbon group which may be substituted, or a heterocyclic group which may be substituted, and R²is a hydrocarbon group which may be substituted or a hydrogen atom), or the like. Specifically, the “C_1-20acyl” may be R¹″CO—, R¹′OCO—, R¹′SO₂—, R¹′SO—, R¹′N(R²′)CO— (wherein R¹′ is a hydrocarbon group which may be substituted, or a heterocyclic group which may be substituted, and R²is a hydrocarbon group which may be substituted or a hydrogen atom).

The “hydrocarbon group which may be substituted” represented by R¹and R²may be exemplified by the “hydrocarbon groups” mentioned as the “substituent which may be further carried by ring A,” or the like.

The “heterocyclic group which may be substituted” represented by R¹may be exemplified by the heterocyclic rings listed for the heterocyclic rings bound to the oxy in the “heterocyclic oxy” mentioned as the “substituent which may be further carried by ring A,” or the like.],

(u) mono-C_1-6alkylamino (e.g., methylamino, ethylamino, propylamino, isopropylamino, butylamino, isobutylamino, sec-butylamino, tert-butylamino, pentylamino, hexylamino, etc.),

(v) di-C_1-6alkylamino (e.g., dimethylamino, diethylamino, dipropylamino, diisopropylamino, butylamino, dibutylamino, etc.),

(w) a 5-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (e.g., 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-pyrrolyl, 3-pyrrolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-(1,2,4-oxadiazolyl), 5-(1,2,4-oxadiazolyl), 1,3,4-oxadiazolyl, 3-(1,2,4-thiadiazolyl), 5-(1,2,4-thiadiazolyl), 1,3,4-thiadiazolyl, 4-(1,2,3-thiadiazolyl), 5-(1,2,3-thiadiazolyl), 1,2,5-thiadiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1H-tetrazolyl, 2H-tetrazolyl, oxoimidazinyl, dioxotriazinyl, pyrrolidinyl, etc.) (wherein this 5-membered ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen),

(x) a 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (e.g., 2-pyridyl, 3-pyridyl, 4-pyridyl, N-oxido-2-pyridyl, N-oxido-3-pyridyl, N-oxido-4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, N-oxido-2-pyrimidinyl, N-oxido-4-pyrimidinyl, N-oxido-5-pyrimidinyl, 2-thiomorpholinyl, 3-thiomorpholinyl, 2-morpholinyl, 3-morpholinyl, piperidinyl, pyranyl, thiopyranyl, 1,4-oxazinyl, 1,4-thiazinyl, 1,3-thiazinyl, 2-piperazinyl, 3-piperazinyl, triazinyl, oxotriazinyl, 3-pyridazinyl, 4-pyridazinyl, pyrazinyl, N-oxido-3-pyridazinyl, N-oxido-4-pyridazinyl, etc.) (wherein this 6-membered ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen),

(y) a bicyclic or tricyclic fused ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms in addition to carbon atoms (e.g., benzofuryl, benzothiazolyl, benzoxazolyl, tetrazolo[1,5-b]pyridazinyl, triazolo[4,5-b]pyridazinyl, benzoimidazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, indolizinyl, quinolizinyl, 1,8-naphthyridinyl, purinyl, pteridinyl, dibenzofuranyl, carbazolyl, acridinyl, phenanthridinyl, chromanyl, benzoxazinyl, phenazinyl, phenothiazinyl, phenoxazinyl, etc.) (wherein this bicyclic or tricyclic fused ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen),

(z) C_1-6alkoxycarbonyl (e.g., methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, etc.),

(A) carbamoyl,

(B) N-mono-C_1-6alkylcarbamoyl (e.g., methylcarbamoyl, ethylcarbamoyl, propylcarbamoyl, isopropylcarbamoyl, butylcarbamoyl, isobutylcarbamoyl, sec-butylcarbamoyl, tert-butylcarbamoyl, pentylcarbamoyl, hexylcarbamoyl, etc.) [the C_1-6alkyl moiety may be substituted with 1 to 5, preferably 1 or 2, substituents selected from (1) C_1-6alkoxy (e.g., methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, etc.), (2) phenyl, (3) amino, (4) di-C_1-6alkylamino (e.g., dimethylamino, diethylamino, dipropylamino, diisopropylamino, butylamino, dibutylamino, etc.), (5) hydroxy, (6) carboxy, (7) C_1-6alkoxycarbonyl (e.g., tert-butoxycarbonyl, etc.) and the like],

(C) N,N-di-C_1-6alkylcarbamoyl (e.g., dimethylcarbamoyl, diethylcarbamoyl, dipropylcarbamoyl, diisopropylcarbamoyl, butylcarbamoyl, dibutylcarbamoyl, etc.),

(D) N-mono-C_6-14arylcarbamoyl (e.g., phenylcarbamoyl, 1-naphthylcarbamoyl, 2-naphthylcarbamoyl, phenanthrylcarbamoyl, anthrylcarbamoyl, etc.),

(E) N-monoheterocyclic carbamoyl

(F) N,N-di-C_6-14arylcarbamoyl (e.g., diphenylcarbamoyl, di(1-naphthyl)carbamoyl, di(2-naphthyl)carbamoyl, di(phenanthryl)carbamoyl, di(anthryl)carbamoyl, N-phenyl-N-(1-naphthyl)carbamoyl, etc.),

(G) N,N-diheterocyclic carbamoyl

(H) N—C_6-14aryl-N-heterocyclic carbamoyl

[wherein the heterocyclic ring bound to the nitrogen atom of the carbamoyl may be exemplified by the heterocyclic rings listed for the heterocyclic rings bound to the oxy of the “heterocyclic oxy”, and the aryl bound to the nitrogen atom of the carbamoyl may be exemplified by phenyl, 1-naphthyl, 2-naphthyl, phenanthryl, anthryl or the like],

(I) C_1-2alkylenedioxy (e.g., methylenedioxy, ethylenedioxy),

(J) oxo,

(K) formyl,

(L) C_1-6alkyl-carbonyl (e.g., acetyl, ethylcarbonyl, propylcarbonyl, isopropylcarbonyl, butylcarbonyl, isobutylcarbonyl, sec-butylcarbonyl, tert-butylcarbonyl, pentylcarbonyl, hexylcarbonyl, etc.),

(M) C_6-14arylcarbonyl (e.g., benzoyl, 1-naphthylcarbonyl, 2-naphthylcarbonyl, phenanthrylcarbonyl, anthrylcarbonyl, etc.),

(N) a 5-membered ring containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (e.g., 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-pyrrolyl, 3-pyrrolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-(1,2,4-oxadiazolyl), 5-(1,2,4-oxadiazolyl), 1,3,4-oxadiazolyl, 3-(1,2,4-thiadiazolyl), 5-(1,2,4-thiadiazolyl), 1,3,4-thiadiazolyl, 4-(1,2,3-thiadiazolyl), 5-(1,2,3-thiadiazolyl), 1,2,5-thiadiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1H-tetrazolyl, 2H-tetrazolyl, oxoimidazinyl, dioxotriazinyl, pyrrolidinyl, etc.)-carbonyl,

(O) a 6-membered ring containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (e.g., 2-pyridyl, 3-pyridyl, 4-pyridyl, N-oxido-2-pyridyl, N-oxido-3-pyridyl, N-oxido-4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, N-oxido-2-pyrimidinyl, N-oxido-4-pyrimidinyl, N-oxido-5-pyrimidinyl, 2-thiomorpholinyl, 3-thiomorpholinyl, 2-morpholinyl, 3-morpholinyl, piperidinyl, pyranyl, thiopyranyl, 1,4-oxazinyl, 1,4-thiazinyl, 1,3-thiazinyl, 2-piperazinyl, 3-piperazinyl, triazinyl, oxotriazinyl, 3-pyridazinyl, 4-pyridazinyl, pyrazinyl, N-oxido-3-pyridazinyl, N-oxido-4-pyridazinyl, etc.)-carbonyl,

(P) a bicyclic or tricyclic fused ring containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms in addition to carbon atoms (e.g., benzofuryl, benzothiazolyl, benzoxazolyl, tetrazolo[1,5-b]pyridazinyl, triazolo[4,5-b]pyridazinyl, benzoimidazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, indolizinyl, quinolizinyl, 1,8-naphthyridinyl, purinyl, pteridinyl, dibenzofuranyl, carbazolyl, acridinyl, phenanthridinyl, chromanyl, benzoxazinyl, phenazinyl, phenothiazinyl, phenoxazinyl, etc.)-carbonyl,

(Q) R³′O—N═CH— (wherein R³is a hydrocarbon group which may be substituted or a hydrogen atom, and the “hydrocarbon group which may be substituted” may be exemplified by the “hydrocarbon groups” mentioned as the “substituents which may be further carried by ring A”),

and the like. These substituents may be present at substitutable positions, and the number of substituents is 1 to 4 when ring A is a benzene ring, and 1 to 3 when ring A is some other ring. These substituents may be further substituted with the above-defined substituents at the substitutable position thereof, and the number of substituents is not particularly limited.

The “substituent” of the “hydrocarbon group” may be preferably exemplified by

(1) mono- or di-C_1-6alkylamino (e.g., methylamino, ethylamino, propylamino, isopropylamino, butylamino, isobutylamino, sec-butylamino, tert-butylamino, pentylamino, hexylamino, dimethylamino, diethylamino, dipropylamino, diisopropylamino, butylamino, dibutylamino, etc.), (2) C_6-14aryl (e.g., phenyl, 1-naphthyl, 2-naphthyl, phenanthryl, anthryl, etc.), (3) hydroxy which may be protected by a protective group (e.g., tert-butyl(dimethyl)silyl [TBDMS], etc.), (4) halogen (e.g., fluorine, chlorine, bromine, iodine, etc.), (5) cyano, (6) carboxyl, (7) C_1-6alkylthio (e.g., methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, sec-butylthio, tert-butylthio, pentylthio, hexylthio, etc.), (8) C_1-6alkylsulfonyl (e.g., methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl, pentylsulfonyl, hexylsulfonyl, etc.), (9) C_1-6alkoxycarbonyl (e.g., methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, etc.), (10) carbamoyl, (11) N-mono-C_1-6alkylcarbamoyl (e.g., methylcarbamoyl, ethylcarbamoyl, propylcarbamoyl, isopropylcarbamoyl, butylcarbamoyl, isobutylcarbamoyl, sec-butylcarbamoyl, tert-butylcarbamoyl, pentylcarbamoyl, hexylcarbamoyl, etc.), (12) N,N-di-C_1-6alkylcarbamoyl (e.g., dimethylcarbamoyl, diethylcarbamoyl, dipropylcarbamoyl, diisopropylcarbamoyl, butylcarbamoyl, dibutylcarbamoyl, etc.), (13) a 5-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (e.g., 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-pyrrolyl, 3-pyrrolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-(1,2,4-oxadiazolyl), 5-(1,2,4-oxadiazolyl), 1,3,4-oxadiazolyl, 3-(1,2,4-thiadiazolyl), 5-(1,2,4-thiadiazolyl), 1,3,4-thiadiazolyl, 4-(1,2,3-thiadiazolyl), 5-(1,2,3-thiadiazolyl), 1,2,5-thiadiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1H-tetrazolyl, 2H-tetrazolyl, oxoimidazinyl, dioxotriazinyl, pyrrolidinyl, etc.), (14) C_1-20acylamino, or the like.

The “hydrocarbon group” is preferably C_6-14aryl (e.g., phenyl, 1-naphthyl, 2-naphthyl, anthryl, phenanthryl, etc.) which may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino (e.g., methylamino, ethylamino, propylamino, isopropylamino, butylamino, isobutylamino, sec-butylamino, tert-butylamino, pentylamino, hexylamino, etc.), (iv) di-C_1-6alkylamino (e.g., dimethylamino, diethylamino, dipropylamino, diisopropylamino, butylamino, dibutylamino, etc.), (v) C_1-6alkoxy (e.g., methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, etc.), and (vi) halogen (e.g., fluorine, chlorine, bromine, iodine).

The hydrocarbon group is preferably C_1-6alkyl or C_3-8cycloalkyl.

Preferably, the substituents which may be further carried by ring A may be exemplified by

(a) C_6-14aryl (e.g., phenyl, 1-naphthyl, 2-naphthyl, anthryl, phenanthryl, etc.) which may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino (e.g., methylamino, ethylamino, propylamino, isopropylamino, butylamino, isobutylamino, sec-butylamino, tert-butylamino, pentylamino, hexylamino, etc.), (iv) di-C_1-6alkylamino (e.g., dimethylamino, diethylamino, dipropylamino, diisopropylamino, butylamino, dibutylamino, etc.), (v) C_1-6alkoxy (e.g., methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, etc.), and (vi) halogen (e.g., fluorine, chlorine, bromine, iodine),

(b) cyano,

(d) carboxy,

(e) nitro,

(f) C_1-6alkyl (e.g., methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, etc.) which may be substituted with di-C_1-6alkylamino (e.g., dimethylamino, diethylamino, dipropylamino, diisopropylamino, butylamino, dibutylamino, etc.),

(g) C_1-6alkoxy (e.g., methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, etc.),

(h) C_1-6alkyl-carbonyloxy (e.g., methylcarbonyloxy, ethylcarbonyloxy, propylcarbonyloxy, isopropylcarbonyloxy, butylcarbonyloxy, isobutylcarbonyloxy, sec-butylcarbonyloxy, tert-butylcarbonyloxy, pentylcarbonyloxy, hexylcarbonyloxy, etc.),

(i) C_1-6alkylthio (e.g., methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, sec-butylthio, tert-butylthio, pentylthio, hexylthio, etc.),

(j) C_1-6alkylsulfinyl (e.g., methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl, pentylsulfinyl, hexylsulfinyl, etc.),

(k) C_1-6alkylsulfonyl (e.g., methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl, pentylsulfonyl, hexylsulfonyl, etc.),

(l) halogen (e.g., fluorine, chlorine, bromine, iodine),

(m) amino,

(n) mono-C_1-6alkylamino (e.g., methylamino, ethylamino, propylamino, isopropylamino, butylamino, isobutylamino, sec-butylamino, tert-butylamino, pentylamino, hexylamino, etc.),

(o) di-C_1-6alkylamino (e.g., dimethylamino, diethylamino, dipropylamino, diisopropylamino, butylamino, dibutylamino, etc.),

(p) a 5-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (e.g., 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-pyrrolyl, 3-pyrrolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-(1,2,4-oxadiazolyl), 5-(1,2,4-oxadiazolyl), 1,3,4-oxadiazolyl, 3-(1,2,4-thiadiazolyl), 5-(1,2,4-thiadiazolyl), 1,3,4-thiadiazolyl, 4-(1,2,3-thiadiazolyl), 5-(1,2,3-thiadiazolyl), 1,2,5-thiadiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1H-tetrazolyl, 2H-tetrazolyl, oxoimidazinyl, dioxotriazinyl, pyrrolidinyl, etc.) (wherein this 5-membered ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen),

(q) a 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (e.g., 2-pyridyl, 3-pyridyl, 4-pyridyl, N-oxido-2-pyridyl, N-oxido-3-pyridyl, N-oxido-4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, N-oxido-2-pyrimidinyl, N-oxido-4-pyrimidinyl, N-oxido-5-pyrimidinyl, 2-thiomorpholinyl, 3-thiomorpholinyl, 2-morpholinyl, 3-morpholinyl, piperidinyl, pyranyl, thiopyranyl, 1,4-oxazinyl, 1,4-thiazinyl, 1,3-thiazinyl, 2-piperazinyl, 3-piperazinyl, triazinyl, oxotriazinyl, 3-pyridazinyl, 4-pyridazinyl, pyrazinyl, N-oxido-3-pyridazinyl, N-oxido-4-pyridazinyl, etc.) (wherein this 6-membered ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen),

(r) a bicyclic or tricyclic fused ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms in addition to carbon atoms (e.g., benzofuryl, benzothiazolyl, benzoxazolyl, tetrazolo[1,5-b]pyridazinyl, triazolo[4,5-b]pyridazinyl, benzoimidazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, indolizinyl, quinolizinyl, 1,8-naphthyridinyl, purinyl, pteridinyl, dibenzofuranyl, carbazolyl, acridinyl, phenanthridinyl, chromanyl, benzoxazinyl, phenazinyl, phenothiazinyl, phenoxazinyl, etc.) (wherein this bicyclic or tricyclic fused ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen),

(s) C_1-6alkoxycarbonyl (e.g., methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, etc.),

(t) carbamoyl,

(u) N-mono-C_1-6alkylcarbamoyl (e.g., methylcarbamoyl, ethylcarbamoyl, propylcarbamoyl, isopropylcarbamoyl, butylcarbamoyl, isobutylcarbamoyl, sec-butylcarbamoyl, tert-butylcarbamoyl, pentylcarbamoyl, hexylcarbamoyl, etc.),

(v) N,N-di-C_1-6alkylcarbamoyl (e.g., dimethylcarbamoyl, diethylcarbamoyl, dipropylcarbamoyl, diisopropylcarbamoyl, butylcarbamoyl, dibutylcarbamoyl, etc.), and

(w) C_1-2alkylenedioxy (e.g., methylenedioxy and ethylenedioxy).

Ring A is preferably a benzene ring which may be substituted with 1 to 4 substituents selected from (a) C_6-14aryl which may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen, (b) cyano, (c) hydroxy, (d) carboxyl, (e) nitro, (f) C_1-6alkyl which may be substituted with di-C_1-6alkylamino, (g) C_1-6alkoxy, (h) C_1-6alkyl-carbonyloxy, (i) C_1-6alkylthio, (j) C_1-6alkylsulfinyl, (k) C_1-6alkylsulfonyl, (l) halogen, (m) amino, (n) mono-C_1-6alkylamino, (o) di-C_1-6alkylamino, (p) a 5-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5-membered ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) s mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (q) a 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 6-membered ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (r) a bicyclic or tricyclic fused ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms in addition to carbon atoms (wherein this bicyclic or tricyclic fused ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (S) C_1-6alkoxycarbonyl, (t) carbamoyl, (u) N-mono-C_1-6alkylcarbamoyl, (v) N,N-di-C_1-6alkylcarbamoyl, and (w) C_1-2alkylenedioxy.

Furthermore, ring A is preferably a benzene ring which may be substituted with 1 to 4 substituents selected from (a) hydroxy, (b) cyano, (c) carboxyl, (d) mono- or dialkylcarbamoyl (i.e., the above-described N-mono-C_1-6alkylcarbamoyl and N,N-di-C_1-6alkylcarbamoyl), (e) acylamino (i.e., the above-described C_1-20acylamino), (f) alkylamino (i.e., the above-described mono-C_1-6alkylamino and di-C_1-6alkylamino), and (g) alkoxycarbonyl (i.e., the above-described C_1-6alkoxycarbonyl), or a benzene ring which may be substituted with a hydrocarbon group substituted with 1 to 4 of the aforementioned substituents. The positions of the substituents in the benzene ring are not particularly limited.

The “hydrocarbon group” of the above-described benzene ring which may be substituted with a hydrocarbon group is preferably, for example, (1) C_1-6alkyl (e.g., methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, etc.), (2) C_2-6alkenyl (e.g., vinyl, allyl, 1-butenyl, 2-butenyl, etc.), (3) C_2-6alkynyl (e.g., ethynyl, propargyl, 2-butynyl, 5-hexynyl, etc.), (4) C_3-8cycloalkyl (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc.), (5) C_6-14aryl (e.g., phenyl, 1-naphthyl, 2-naphthyl, anthryl, phenanthryl, etc.), (6) C_7-14aralkyl (e.g., benzyl, phenethyl, etc.), or the like.

In Compound (I-a), X is an oxygen atom, a sulfur atom or NR³, wherein R³is a hydrocarbon group which may be substituted or a hydrogen atom. The “hydrocarbon group” of the “hydrocarbon group which may be substituted” represented by R³may be exemplified by (1) C_1-6alkyl (e.g., methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, etc.), (2) C_2-6alkenyl (e.g., vinyl, allyl, 1-butenyl, 2-butenyl, etc.), (3) C_2-6alkynyl (e.g., ethynyl, propargyl, 2-butynyl, 5-hexynyl, etc.), (4) C_3-8cycloalkyl which may be fused with a C_6-14aryl ring (e.g., benzene, naphthalene, anthracene, phenanthrene, etc.) (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, 1,2,3,4-tetrahydronaphthalen-1-yl, 2,3-dihydro-1H-inden-1-yl, 6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-yl, etc.), (5) C_6-14aryl which may be fused with a C_3-8cycloalkane (e.g., cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, etc.) (e.g., phenyl, 1-naphthyl, 2-naphthyl, anthryl, phenanthryl, 5,6,7,8-tetrahydronaphthalen-1-yl, etc.), (6) C_7-14aralkyl (e.g., benzyl, phenethyl, etc.), or the like.

The “substituent” of the hydrocarbon group which may be substituted represented by R³may be exemplified by those mentioned as the substituents which may be further carried by ring A, and the number of substituents is from 1 to 3.

X is preferably an oxygen atom or NR³, wherein R³is a hydrocarbon group which may be substituted or a hydrogen atom.

More preferably, X is an oxygen atom or NR³, wherein R³is (1) a hydrogen atom, (2) C_1-6alkyl which may be substituted with 1 to 3 substituents selected from (a) C_6-14aryl which may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen, (b) cyano, (c) hydroxy, (d) carboxy, (e) nitro, (f) C_1-6alkyl which may be substituted with di-C_1-6alkylamino, (g) C_1-6alkoxy, (h) C_1-6alkylcarbonyloxy, (i) C_1-6alkylthio, (j) C_1-6alkylsulfinyl, (k) C_1-6alkylsulfonyl, (l) halogen, (m) amino, (n) mono-C_1-6alkylamino, (o) di-C_1-6alkylamino, (p) a 5-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5-membered ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (q) a 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 6-membered ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (r) a bicyclic or tricyclic fused ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this bicyclic or tricyclic fused ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (s) C_1-6alkoxycarbonyl, (t) carbamoyl, (u) N-mono-C_1-6alkylcarbamoyl, (v) N,N-di-C_1-6alkylcarbamoyl, and (w) C_1-2alkylenedioxy (hereinafter (a)-(w) are briefly referred to as Substituent Group A), (3) C_2-6alkenyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (4) C_2-6alkynyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (5) C_3-8cycloalkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (6) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (7) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A. Among these, X is preferably an oxygen atom or NH.

In Compound (I), R¹is a hydrocarbon group which may be substituted or a hydrogen atom. The “hydrocarbon group which may be substituted” represented by R¹may be exemplified by those mentioned as the “hydrocarbon group which may be substituted” represented by R³.

R¹is preferably (1) a hydrogen atom, or (2) C_1-6alkyl which may be substituted with 1 to 3 substituents selected from (a) C_6-14aryl which may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen, (b) cyano, (c) hydroxy, (d) carboxy, (e) nitro, (f) C_1-6alkyl which may be substituted with di-C_1-6alkylamino, (g) C_1-6alkoxy, (h) C_1-6alkyl-carbonyloxy, (i) C_1-6alkylthio, (j) C_1-6alkylsulfinyl, (k) C_1-6alkylsulfonyl, (l) halogen, (m) amino, (n) mono-C_1-6alkylamino, (o) di-C_1-6alkylamino, (p) a 5-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5-membered ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (q) a 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 6-membered ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (r) a bicyclic or tricyclic fused ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this bicyclic or tricyclic fused ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (s) C_1-6alkoxycarbonyl, (t) carbamoyl, (u) N-mono-C_1-6alkylcarbamoyl, (v) N,N-di-C_1-6alkylcarbamoyl, and (w) C_1-2alkylenedioxy, and among these, a hydrogen atom or C_1-6alkyl, particularly a hydrogen atom, is preferred.

In Compound (I), R²is

(1) a group represented by the formula:
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(2) a group represented by the formula:
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(3) a group represented by the formula:
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(4) a group represented by the formula:
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(5) a group represented by the formula:
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(6) a group represented by the formula:
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(7) a group represented by the formula:
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(8) a group represented by the formula:
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[wherein ring B⁸is a C_10-14aryl ring which may be further substituted, or an aromatic heterocycle which may be further substituted; Z⁸is C_1-6alkylene which may be substituted or a bond; R¹⁸is (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; and R¹⁹is (a) a hydrocarbon group which may be substituted, or (b) a heterocyclic group which may be substituted; or R¹⁸and R¹⁹may form a ring together with the adjacent nitrogen atom], or

(9) a group represented by the formula:
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The “substituent” of the “benzene ring which may be further substituted” represented by ring B¹through ring B⁶may be exemplified by those mentioned as the substituents which may be further carried by ring A, and the number of substituents is from 1 to 3.

The “C_10-14aryl ring” of the “C_10-14aryl ring which may be further substituted” represented by ring B⁷or ring B⁸may be exemplified by a naphthalene ring, a phenanthrene ring, an anthracene ring or the like.

The “substituent” of the “C_10-14aryl ring which may be further substituted” represented by ring B⁷or ring B⁸may be exemplified by those mentioned as the substituents which may be further carried by ring A, and the number of substituents is from 1 to 3.

The “C_6-14aryl ring” of the “C_6-14aryl ring which may be further substituted” represented by ring B⁹may be exemplified by a benzene ring, a naphthalene ring, a phenanthrene ring, an anthracene ring or the like.

The “substituent” of the “C_6-14aryl ring which may be further substituted” represented by ring B⁹may be exemplified by those mentioned as the substituents which may be further carried by ring A, and the number of substituents is from 1 to 3.

The “aromatic heterocycle” of the “aromatic heterocycle which may be further substituted” represented by ring B⁷, ring B⁸or ring B⁹may be exemplified by a 5-membered aromatic heterocycle (e.g., a thiophene ring, a furan ring, a pyrrole ring, an oxazole ring, a thiazole ring, a pyrazole ring, an imidazole ring, an isoxazole ring, an isothiazole ring, a 1,2,4-oxadiazole ring, a 1,3,4-oxadiazole ring, a 1,2,4-thiadiazole ring, a 1,3,4-thiadiazole ring, a 1,2,3-triazole ring, a 1,2,4-triazole ring, a 1H-tetrazole ring, a 2H-tetrazole ring, etc.), a 6-membered aromatic heterocycle (e.g., a pyridine ring, a pyrimidine ring, a triazinine ring, a pyridazine ring, a pyrazine ring, etc.), a bicyclic or tricyclic fused aromatic heterocycle (e.g., a benzofuran ring, a benzothiazole ring, a benzoxazole ring, a tetrazolo[1,5-b]pyridazine ring, a triazolo[4,5-b]pyridazine ring, a benzoimidazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a phthalazine ring, a quinazoline ring, a quinoxaline ring, an indolizine ring, a quinolizine ring, a 1,8-naphthyridine ring, a purine ring, a pteridine ring, a dibenzofuran ring, a carbazole ring, an acridine ring, a phenanthridine ring, a chromane ring, a benzoxazine ring, a phenazine ring, a phenothiazine ring, a phenoxazine ring, etc.), an indole ring or the like.

The “substituent” of the aromatic heterocycle which may be further substituted represented by ring B⁷, ring B⁸or ring B⁹may be exemplified by those mentioned as the substituents which may be further carried by ring A, and the number of substituents is from 1 to 3.

The “C_1-6alkylene” of the “C_1-6alkylene which may be substituted” represented by Z¹through Z⁹may be exemplified by —CH₂—, —CH₂CH₂—, —CH₂CH₂CH₂—, —CH₂CH₂CH₂CH₂—, —CH₂CH₂CH₂CH₂CH₂— or —CH₂CH₂CH₂CH₂CH₂CH₂—.

The “substituent” of the C_1-6alkylene which may be substituted, represented by Z¹through Z⁹may be exemplified by those mentioned as the substituents which may be further carried by ring A, and the number of substituents is from 1 to 3.

The “hydrocarbon group which may be substituted” represented by R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹and R²⁰may be exemplified by those mentioned as the “hydrocarbon group which may be substituted” represented by R³.

The “heterocyclic group” of the “heterocyclic group which may be substituted” represented by R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹and R²⁰may be exemplified by a 5- or 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (e.g., a 5-membered ring group such as 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-pyrrolyl, 3-pyrrolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-(1,2,4-oxadiazolyl), 5-(1,2,4-oxadiazolyl), 1,3,4-oxadiazolyl, 3-(1,2,4-thiadiazolyl), 5-(1,2,4-thiadiazolyl), 1,3,4-thiadiazolyl, 4-(1,2,3-thiadiazolyl), 5-(1,2,3-thiadiazolyl), 1,2,5-thiadiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1H-tetrazolyl, 2H-tetrazolyl, oxoimidazinyl, dioxotriazinyl or pyrrolidinyl; a 6-membered ring group such as 2-pyridyl, 3-pyridyl, 4-pyridyl, N-oxido-2-pyridyl, N-oxido-3-pyridyl, N-oxido-4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, N-oxido-2-pyrimidinyl, N-oxido-4-pyrimidinyl, N-oxido-5-pyrimidinyl, 2-thiomorpholinyl, 3-thiomorpholinyl, 2-morpholinyl, 3-morpholinyl, piperidinyl, pyranyl, thiopyranyl, 1,4-oxazinyl, 1,4-thiazinyl, 1,3-thiazinyl, 2-piperazinyl, 3-piperazinyl, triazinyl, oxotriazinyl, 3-pyridazinyl, 4-pyridazinyl, pyrazinyl, N-oxido-3-pyridazinyl or N-oxido-4-pyridazinyl), or the like.

The “substituent” of the “heterocyclic group which may be substituted” may be exemplified by those mentioned as the substituents which may be further carried by ring A, and the number of substituents is from 1 to 3.

When R⁴and R⁵, R⁶and R⁷, R⁸and R⁹, R¹²and R¹³, R¹⁴and R¹⁵, R¹⁶and R¹⁷, and R¹⁸and R¹⁹respectively form a ring together with the adjacent nitrogen ring, the groups represented by —NR⁴R⁵, —NR⁶R⁷, —NR⁸R⁹, —NR¹²R¹³, —NR¹⁴R¹⁵, —NR¹⁶R¹⁷and —NR¹⁸R¹⁹are respectively a cyclic group represented by 1-pyrrolidinyl, 1-pyrrolinyl, 1-pyrrolyl, azepan-1-yl, 1-imidazolidinyl, 1-imidazolinyl, 1-imidazolyl, 2-pyrazolidinyl, 2-pyrazolinyl, 1-pyrazolyl, 1-indolinyl, 1-indolyl, 2-isoindolinyl, 2-isoindolyl, 2,3-dihydro-1H-indol-1-yl, 1-piperidyl, 3,4-dihydro-1,5-naphthyridin-1(2H)-yl, 1,2,3,4-tetrahydroquinolin-1-yl, 3,4-dihydroquinolin-1(2H)-yl, 3,4-dihydroisoquinolin-2(1H)-yl, 1-piperazinyl, octahydroquinolin-1(2H)-yl, octahydroisoquinolin-2(1H)-yl, 3,4-dihydroquinoxalin-1(2H)-yl, 1H-azepin-1-yl, 2,3,4,5,6,7-hexahydro-1H-azepin-1-yl, 2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl, 1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl, 3,4,5,6-tetrahydro-1-benzazocin-1(2H)-yl, 2,3-dihydro-4,1-benzothiazepin-1(5H)-yl, 3,4-dihydro-1,5-benzothiazepin-5(2H)-yl, 2,3-dihydro-4,1-benzothiazepin-1(5H)-yl, 2,3-dihydro-4,1-benzoxazepin-1(5H)-yl, 1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-1-yl, 2,3-dihydro-4H-1,4-benzoxazin-4-yl, 3,4-dihydro-2H-1,4-benzoxazin-1-yl, 3,4-dihydro-1,5-benzoxazepin-5(2H)-yl, 5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepin-4-yl, 4-morpholinyl, 4-thiomorpholinyl, 2,3-dihydro-4H-pyrido[3,2-b][1,4]oxazin-4-yl, 2,3-dihydro-4H-1,4-benzothiazin-4-yl, 5,6,7,8-tetrahydropyrazolo[4,3-b]azepin-4(1H)-yl and the like. The cyclic groups may be substituted, and the substituent for the cyclic groups may be exemplified by those mentioned as the substituents which may be further carried by ring A, while the number of substituents is from 1 to 3.

The “aromatic group” of the “aromatic group which may be substituted” represented by R¹¹may be exemplified by an aromatic hydrocarbon group or an aromatic heterocyclic group.

The aromatic hydrocarbon group may be exemplified by C_6-14aryl such as phenyl, 1-naphthyl, 2-naphthyl, anthryl or phenanthryl. The aromatic heterocyclic group may be exemplified by a 5- or 6-membered aromatic heterocyclic group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (e.g., a 5-membered aromatic heterocyclic group such as 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-pyrrolyl, 3-pyrrolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-(1,2,4-oxadiazolyl), 5-(1,2,4-oxadiazolyl), 1,3,4-oxadiazolyl, 3-(1,2,4-thiadiazolyl), 5-(1,2,4-thiadiazolyl), 1,3,4-thiadiazolyl, 4-(1,2,3-thiadiazolyl), 5-(1,2,3-thiadiazolyl), 1,2,5-thiadiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1H-tetrazolyl, 2H-tetrazolyl, oxoimidazinyl, dioxotriazinyl or pyrrolidinyl; a 6-membered aromatic heterocyclic group such as 2-pyridyl, 3-pyridyl, 4-pyridyl, N-oxido-2-pyridyl, N-oxido-3-pyridyl, N-oxido-4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, N-oxido-2-pyrimidinyl, N-oxido-4-pyrimidinyl, N-oxido-5-pyrimidinyl, triazinyl, oxotriazinyl, 3-pyridazinyl, 4-pyridazinyl, pyrazinyl, N-oxido-3-pyridazinyl or N-oxido-4-pyridazinyl), or a fused ring in which such a 5- or 6-membered aromatic heterocycle is fused with a benzene ring, or the like.

The “substituent” of the “aromatic group which may be substituted” represented by R¹¹may be exemplified by those mentioned as the substituents which may be further carried by ring A, and the number of substituents is from 1 to 3.

The “aralkyl group” of the “aralkyl group which may be substituted” represented by R¹¹may be exemplified by C_7-14aralkyl such as benzyl or phenethyl.

The “substituent” of the “aralkyl group which may be substituted” represented by R¹¹may be exemplified by those mentioned as the substituents which may be further carried by ring A, and the number of substituents is from 1 to 3.

The “alkyl group” of the “alkyl group substituted with a heterocyclic group which may be substituted” represented by R¹¹may be exemplified by C_1-6alkyl such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl or hexyl.

The “heterocyclic group” of the “alkyl group substituted with a heterocyclic group which may be substituted” represented by R¹¹may be exemplified by (i) a 5-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (e.g., 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-pyrrolyl, 3-pyrrolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-(1,2,4-oxadiazolyl), 5-(1,2,4-oxadiazolyl), 1,3,4-oxadiazolyl, 3-(1,2,4-thiadiazolyl), 5-(1,2,4-thiadiazolyl), 1,3,4-thiadiazolyl, 4-(1,2,3-thiadiazolyl), 5-(1,2,3-thiadiazolyl), 1,2,5-thiadiazolyl, 1,2,3-triazolyl, 25 1,2,4-triazolyl, 1H-tetrazolyl, 2H-tetrazolyl, oxoimidazinyl, dioxotriazinyl, pyrrolidinyl, etc.), (ii) a 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (e.g., 2-pyridyl, 3-pyridyl, 4-pyridyl, N-oxido-2-pyridyl, N-oxido-3-pyridyl, N-oxido-4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, N-oxido-2-pyrimidinyl, N-oxido-4-pyrimidinyl, N-oxido-5-pyrimidinyl, 2-thiomorpholinyl, 3-thiomorpholinyl, 2-morpholinyl, 3-morpholinyl, piperidinyl, pyranyl, thiopyranyl, 1,4-oxazinyl, 1,4-thiazinyl, 1,3-thiazinyl, 2-piperazinyl, 3-piperazinyl, triazinyl, oxotriazinyl, 3-pyridazinyl, 4-pyridazinyl, pyrazinyl, N-oxido-3-pyridazinyl, N-oxido-4-pyridazinyl, etc.), or (iii) a bicyclic or tricyclic fused ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (e.g., benzofuryl, benzothiazolyl, benzoxazolyl, tetrazolo[1,5-b]pyridazinyl, triazolo[4,5-b]pyridazinyl, benzoimidazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, indolizinyl, quinolizinyl, 1,8-naphthyridinyl, purinyl, pteridinyl, dibenzofuranyl, carbazolyl, acridinyl, phenanthridinyl, chromanyl, benzoxazinyl, phenazinyl, phenothiazinyl, phenoxazinyl, etc.).

The “substituent” of the “alkyl group substituted with a heterocyclic group which may be substituted” represented by R¹¹may be exemplified by (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino (e.g., methylamino, ethylamino, propylamino, isopropylamino, butylamino, isobutylamino, sec-butylamino, tert-butylamino, pentylamino, hexylamino, etc.), (iv) di-C_1-6alkylamino (e.g., dimethylamino, diethylamino, dipropylamino, diisopropylamino, butylamino, dibutylamino, etc.), (v) C_1-6alkoxy (e.g., methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, etc.), (vi) halogen (e.g., fluorine, chlorine, bromine, iodine), or the like, and the heterocyclic group may have 1 to 3 of such substituents at substitutable positions.

When R¹⁰and R¹¹together with the adjacent nitrogen atom form a heterocyclic ring consisting of carbon and nitrogen atoms as ring-constituting moieties , the group represented by —NR¹⁰R¹¹is a cyclic group selected from 1-pyrrolidinyl, 1-pyrrolinyl, 1-pyrrolyl, 1-imidazolidinyl, 1-imidazolinyl, 1-imidazolyl, 2-pyrazolidinyl, 2-pyrazolinyl, 1-pyrazolyl, 1-indolinyl, 1-indolyl, 2-isoindolinyl, 2-isoindolyl, 1-piperidyl, 3,4-dihydroquinolin-1(2H)-yl, 3,4-dihydroisoquinolin-2(1H)-yl, 1-piperazinyl, 3,4-dihydroquinoxalin-1(2H)-yl, 1H-azepin-1-yl, 2,3,4,5,6,7-hexahydro-1H-azepin-1-yl, 2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl, 1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl, 1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl, and the like. These cyclic groups may be substituted, and the substituent for the cyclic groups may be exemplified by those mentioned as the substituents which may be further carried by ring A described above, while the number of substituents is from 1 to 3.

R²is preferably (1) a group represented by the formula:
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wherein each reference symbol has the meaning as defined above,

(2) a group represented by the formula:
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wherein each reference symbol has the meaning as defined above, or

(3) a group represented by the formula:
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wherein each reference symbol has the meaning as defined above.

Among these, R²is preferably

(1) a group represented by the formula:
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wherein ring B²′ is a benzene ring which may be further substituted with 1 to 3 substituents selected from (a) C_6-14aryl which may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen, (b) cyano, (c) hydroxy, (d) carboxy, (e) nitro, (f) C_1-6alkyl which may be substituted with di-C_1-6alkylamino, (g) C_1-6alkoxy, (h) C_1-6alkyl-carbonyloxy, (i) C_1-6alkylthio, (j) C_1-6alkylsulfinyl, (k) C_1-6alkylsulfonyl, (l) halogen, (m) amino, (n) mono-C_1-6alkylamino, (o) di-C_1-6alkylamino, (p) a 5-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5-membered ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (q) a 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 6-membered ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (r) a bicyclic or tricyclic fused ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this bicyclic or tricyclic fused ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (s) C_1-6alkoxycarbonyl, (t) carbamoyl, (u) N-mono-C_1-6alkylcarbamoyl, (v) N,N-di-C_1-6alkylcarbamoyl, and (w) C_1-2alkylenedioxy (hereinafter (a)-(w) are briefly referred to as Substituent Group A); R⁶′ is (a) a hydrogen atom, (b) C_1-6alkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (c) C_2-6alkenyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (d) C_2-6alkynyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (e) C_3-8cycloalkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (f) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (g) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (h) a 5- or 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); and R⁷′ is (a) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (g) a 5- or 6-membered aromatic ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); or R⁶and R⁷may form a ring together with the adjacent nitrogen atom,

(2) a group represented by the formula:
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wherein ring B⁵′ is a benzene ring which may be further substituted with 1 to 3 substituents selected from the Substituent Group A; R¹²is (a) C_1-6alkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (b) C_2-6alkenyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (C) C_2-6alkynyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (d) C_3-8cycloalkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (e) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (f) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (g) a 5- or 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); and R¹³′ is (a) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (b) a 5- or 6-membered aromatic ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); or R¹²′ and R¹³′ may form a ring together with the adjacent nitrogen atom, or

(3) a group represented by the formula:
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wherein ring B⁷′ is an aromatic heterocycle which may be substituted with 1 to 3 substituents selected from the Substituent Group A; R¹⁶′ is (a) a hydrogen atom, (b) C_1-6alkyl which may be substituted with 1 to 3 substituents selected fro the Substituent Group A, (c) C_2-6alkenyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (d) C_2-6alkynyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (e) C_3-8cycloalkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (f) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (g) C_7-14aralkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (h) a 5- or 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); and R¹⁷′ is (a) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, or (b) a 5- or 6-membered aromatic ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); or R¹⁶′ and R¹⁷′ may form a ring together with the adjacent nitrogen atom.

When R⁶′and R⁷′, R¹²′ and R¹³′, and R¹⁶α and R¹⁷′ respectively form a ring together with the adjacent nitrogen atom, the groups represented by —NR⁶′R⁷′, —NR¹²′R¹³′ and —NR¹⁶′R¹⁷′ are respectively a cyclic group selected from 1-pyrrolidinyl, 1-pyrrolinyl, 1-pyrrolyl, 1-imidazolidinyl, 1-imidazolinyl, 1-imidazolyl, 2-pyrazolidinyl, 2-pyrazolinyl, 1-pyrazolyl, 1-indolinyl, 1-indolyl, 2-isoindolinyl, 2-isoindolyl, 1-piperidyl, 3,4-dihydroquinolin-1(2H)-yl, 3,4-dihydroisoquinolin-2(1H)-yl, 1-piperazinyl, 3,4-dihydroquinoxalin-1(2H)-yl, 1H-azepin-1-yl, 2,3,4,5,6,7-hexahydro-1H-azepin-1-yl, 2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl, 1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl, 1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl, 2,3-dihydro-4H-1,4-benzoxazin-4-yl, 3,4-dihydro-1,5-benzoxazepin-5(2H)-yl, 4-morpholinyl, 4-thiomorpholinyl, and the like. These cyclic groups may be substituted, and the substituents for the cyclic groups may be exemplified by those mentioned as the substituents which may be further carried by ring A described above, while the number of substituents is from 1 to 3.

Furthermore, in Formula (I-b):
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ring A and R¹are as defined above.

R²¹and R²², which may be identical or different, are each a hydrocarbon group which may be substituted or a hydrogen atom.

The “hydrocarbon group which may be substituted” represented by R²¹and R²²may be exemplified by those mentioned as the “hydrocarbon group which may be substituted” represented by R³described above.

R²³is

(1) a group represented by the formula:
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wherein ring B¹⁰is a benzene ring which may be further substituted, Z¹⁰is C_1-6alkylene which may be substituted or a bond; and R²⁴and R²⁵, which may be identical or different, are each (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; or R²⁴and R²⁵may form a ring together with the adjacent nitrogen atom,

(2) a group represented by the formula:
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wherein ring B¹¹is a benzene ring which may be further substituted; Z¹¹is C_1-6alkylene which may be substituted or a bond; and R²⁶and R²⁷, which may be identical or different, are each (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; or R²⁶and R²⁷may form a ring together with the adjacent nitrogen atom,

(3) a group represented by the formula:
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wherein ring B¹²is a benzene ring which may be further substituted; Z¹²is C_1-6alkylene which may be substituted or a bond; and R²⁸and R²⁹, which may be identical or different, are each (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; or R²⁸and R²⁹may form a ring together with the adjacent nitrogen atom,

(4) a group represented by the formula:
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wherein ring B¹³is a benzene ring which may be further substituted; Z¹³is C_1-6alkylene which may be substituted or a bond; and R³⁰and R³¹, which may be identical or different, are each (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; or R³⁰and R³¹may form a ring together with the adjacent nitrogen atom,

(5) a group represented by the formula:
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wherein ring B¹⁴is a benzene ring which may be further substituted; Z¹⁴is C_1-6alkylene which may be substituted or a bond; and R³²and R³³, which may be identical or different, are each (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; or R³²and R³³may form a ring together with the adjacent nitrogen atom,

(6) a group represented by the formula:
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wherein ring B¹⁵is a benzene ring which may be further substituted; Z¹⁵is C_1-6alkylene which may be substituted or a bond; and R³⁴and R³⁵, which may be identical or different, are each (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; or R³⁴and R³⁵may form a ring together with the adjacent nitrogen atom,

(7) a group represented by the formula:
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wherein ring B¹⁶is a C_10-14aryl ring which may be further substituted, or an aromatic heterocycle which may be further substituted; Z¹⁶is C_1-6alkylene which may be substituted or a bond; and R³⁶and R³⁷, which may be identical or different, are each (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; or R³⁶and R³⁷may form a ring together with the adjacent nitrogen atom,

(8) a group represented by the formula:
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wherein ring B¹⁷is a C_10-14aryl ring which may be further substituted, or an aromatic heterocycle which may be further substituted; Z¹⁷is C_1-6alkylene which may be substituted or a bond; and R³⁸and R³⁹, which may be identical or different, are each (a) a hydrogen atom, (b) a hydrocarbon group which may be substituted, or (c) a heterocyclic group which may be substituted; or R³⁸and R³⁹may form a ring together with the adjacent nitrogen atom, or

(9) a group represented by the formula:
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The “substituent” of the “benzene ring which may be further substituted” represented by ring B¹⁰through ring B¹⁵may be exemplified by those mentioned as the substituents which may be further carried by ring A described above, and the number of substituents is from 1 to 3.

The “C_10-14aryl ring” of the “C_10-14aryl ring which may be further substituted” represented by ring B¹⁶and ring B¹⁷may be exemplified by a naphthalene ring, a phenanthrene ring, an anthracene ring or the like.

The “substituent” of the “C_10-14aryl ring which may be further substituted” represented by B¹⁶and ring B¹⁷may be exemplified by those mentioned as the substituents which may be further carried by ring A described above, and the number of substituents is from 1 to 3.

The “C_6-14aryl ring” of the “C_6-14aryl ring which may be further substituted” represented by ring B18 may be exemplified by a benzene ring, a naphthalene ring, a phenanthrene ring, an anthracene ring or the like.

The “substituent” of the “C_6-14aryl ring which may be further substituted” represented by ring B¹⁸may be exemplified by those mentioned as the substituents which may be further carried by ring A described above, and the number of substituents is from 1 to 3.

The “aromatic heterocycle” of the “aromatic cyclic ring which may be further substituted” represented by ring B¹⁶, ring B¹⁷and ring B¹⁸may be exemplified by a 5-membered aromatic heterocycle (e.g., a thiophene ring, a furan ring, a pyrrole ring, an oxazole ring, a thiazole ring, a pyrazole ring, an imidazole ring, an isoxazole ring, an isothiazole ring, a 1,2,4-oxadiazole ring, a 1,3,4-oxadiazole ring, a 1,2,4-thiadiazole ring, a 1,3,4-thiadiazole ring, a 1,2,3-triazole ring, a 1,2,4-triazole ring, a 1H-tetrazole ring, a 2H-tetrazole ring, etc.), a 6-membered aromatic heterocycle (e.g., a pyridine ring, a pyrimidine ring, a triazinine ring, a pyridazine ring, a pyrazine ring, etc.), a bicyclic or tricyclic fused aromatic heterocycle (e.g., a benzofuran ring, a benzothiazole ring, a benzoxazole ring, a tetrazolo[1,5-b]pyridazine ring, a triazolo[4,5-b]pyridazine ring, a benzoimidazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a phthalazine ring, a quinazoline ring, a quinoxaline ring, an indolizine ring, a quinolizine ring, a 1,8-naphthyridine ring, a purine ring, a pteridine ring, a dibenzofuran ring, a carbazole ring, an acridine ring, a phenanthridine ring, a chromane ring, a benzoxazine ring, a phenazine ring, a phenothiazine ring, a phenoxazine ring, an indole ring, etc.), or the like.

The “substituent” of the “aromatic heterocycle which may be further substituted” represented by ring B¹⁶, ring B¹⁷and ring B¹⁸may be exemplified by those mentioned as the substituents which may be further carried by ring A described above, and the number of substituents is from 1 to 3.

The “C_1-6alkylene” of the “C_1-6alkylene which may be substituted” represented by Z¹⁰through Z¹⁸may be exemplified by —CH₂—, —CH₂CH₂—, —CH₂CH₂CH₂—, —CH₂CH₂CH₂CH₂—, —CH₂CH₂CH₂CH₂CH₂—, or —CH₂CH₂CH₂CH₂CH₂CH₂—.

The “substituent” of the C_1-6alkylene which may be substituted, represented by Z¹⁰through Z¹⁸may be exemplified by those mentioned as the substituents which may be further carried by ring A described above, and the number of substituents is from 1 to 3.

The “hydrocarbon group which may be substituted” represented by R²⁴, R²⁵, R²⁶, R²⁷, R²⁸, R²⁹, R³⁰, R³¹, R³², R³³, R³⁴, R³⁵, R³⁶, R³⁷, R³⁸, R³⁹and R⁴⁰may be exemplified by those mentioned as the “hydrocarbon group which may be substituted” represented by R³above.

The “heterocyclic group” of the “heterocyclic group which may be substituted” represented by R²⁴, R²⁵, R²⁶, R²⁷, R²⁸, R²⁹, R³⁰, R³¹, R³², R³³, R³⁴, R³⁵, R³⁶, R³⁷, R³⁸, R³⁹and R⁴⁰may be exemplified by a 5- or 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (e.g., a 5-membered ring group such as 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-pyrrolyl, 3-pyrrolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-(1,2,4-oxadiazolyl), 5-(1,2,4-oxadiazolyl), 1,3,4-oxadiazolyl, 3-(1,2,4-thiadiazolyl), 5-(1,2,4-thiadiazolyl), 1,3,4-thiadiazolyl, 4-(1,2,3-thiadiazolyl), 5-(1,2,3-thiadiazolyl), 1,2,5-thiadiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1H-tetrazolyl, 2H-tetrazolyl, oxoimidazinyl, dioxotriazinyl or-pyrrolidinyl; a 6-membered ring group such as 2-pyridyl, 3-pyridyl, 4-pyridyl, N-oxido-2-pyridyl, N-oxido-3-pyridyl, N-oxido-4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, N-oxido-2-pyrimidinyl, N-oxido-4-pyrimidinyl, N-oxido-5-pyrimidinyl, 2-thiomorpholinyl, 3-thiomorpholinyl, 2-morpholinyl, 3-morpholinyl, piperidinyl, pyranyl, thiopyranyl, 1,4-oxazinyl, 1,4-thiazinyl, 1,3-thiazinyl, 2-piperazinyl, 3-piperazinyl, triazinyl, oxotriazinyl, 3-pyridazinyl, 4-pyridazinyl, pyrazinyl, N-oxido-3-pyridazinyl or N-oxido-4-pyridazinyl), or the like.

The “substituent” of the “heterocyclic group which may be substituted” may be exemplified by those mentioned as the substituents which may be further carried by ring A described above, and the number of substituents is from 1 to 3.

When R²⁴and R²⁵, R²⁶and R²⁷, R²⁸and R²⁹, R³⁰and R³¹, R³²and R³³, R³⁴and R³⁵, R³⁶and R³⁷, and R³⁸and R³⁹respectively form a ring together with the adjacent nitrogen atom, the group represented by —NR²⁴R²⁵, —NR²⁶R²⁷, —NR²⁸R²⁹, —NR³⁰R³¹, —NR³²R³³, —NR³⁴R³⁵, —NR³⁶R³⁷and —NR³⁸R³⁹is a cyclic group selected from 1-pyrrolidinyl, 1-pyrrolinyl, 1-pyrrolyl, azepan-1-yl, 1-imidazolidinyl, 1-imidazolinyl, 1-imidazolyl, 2-pyrazolidinyl, 2-pyrazolinyl, 1-pyrazolyl, 1-indolinyl, 1-indolyl, 2-isoindolinyl, 2-isoindolyl, 2,3-dihydro-1H-indol-1-yl, 1-piperidyl, 3,4-dihydro-1,5-naphthyridin-1(2H)-yl, 1,2,3,4-tetrahydroquinolin-1-yl, 3,4-dihydroquinolin-1(2H)-yl, 3,4-dihydroisoquinolin-2(1H)-yl, 1-piperazinyl, octahydroquinolin-1(2H)-yl, octahydroisoquinolin-2(1H)-yl, 3,4-dihydroquinoxalin-1(2H)-yl, 1H-azepin-1-yl, 2,3,4,5,6,7-hexahydro-1H-azepin-1-yl, 2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl, 1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl, 3,4,5,6-tetrahydro-1-benzazocin-1(2H)-yl, 2,3-dihydro-4,1-benzothiazepin-1(5H)-yl, 3,4-dihydro-1,5-benzothiazepin-5(2H)-yl, 2,3-dihydro-4,1-benzothiazepin-1(5H)-yl, 2,3-dihydro-4,1-benzoxazepin-1(5H)-yl, 1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-1-yl, 2,3-dihydro-4H-1,4-benzoxazin-4-yl, 3,4-dihydro-2H-1,4-benzoxazin-1-yl, 3,4-dihydro-1,5-benzoxazepin-5(2H)-yl, 5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepin-4-yl, 4-morpholinyl, 4-thiomorpholinyl, 2,3-dihydro-4H-pyrido[3,2-b][1,4]oxazin-4-yl, 2,3-dihydro-4H-1,4-benzothiazin-4-yl, 5,6,7,8-tetrahydropyrazolo[4,3-b]azepin-4(1H)-yl and the like. These cyclic groups may be substituted, and the substituent for the cyclic groups may be exemplified by those mentioned as the substituents which may be further carried by ring A described above, while the number of substituents is from 1 to 3.

As a preferred embodiment of Compound (I), mention may be made of Compound (I-a).

As a preferred embodiment of Compound (I), mention may be made of a compound represented by the formula:
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wherein ring A, X and R¹are as defined above,

R²is

(1) a group represented by the formula:
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[wherein ring B¹, Z¹, R⁴and R⁵are as defined above],

(2) a group represented by the formula:
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[wherein ring B², Z², R⁶and R⁷are as defined above],

(3) a group represented by the formula:
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[wherein ring B³, Z³, R⁸and R⁹are as defined above, provided that when R⁸is a hydrogen atom, R⁹is (a) an aryl group which may be substituted, (b) an aralkyl group which may be substituted, or (c) an alkyl group substituted with a heterocyclic group which may be substituted],

(4) a group represented by the formula:
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[wherein ring B⁴, Z⁴, R¹⁰and R¹¹are as defined above],

(5) a group represented by the formula:
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[wherein ring B⁵, Z⁵, R¹²and R¹³are as defined above],

(6) a group represented by the formula:
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[wherein ring B⁶, Z⁶, R¹⁴and R¹⁵are as defined above],

(7) a group represented by the formula:
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[wherein ring B⁷, Z⁷, R¹⁶and R¹⁷are as defined above], or

(8) a group represented by the formula:
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[wherein ring B⁸, Z⁸, R¹⁸and R¹⁹are as defined above]; provided that

7-chloro-1-[4-(1,4-dihydro-2,4-dioxo-3(2H)-quinazolinyl)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine, and

N,N-dibutyl-4-(1,4-dihydro-2,4-dioxo-3(2H)-quinazolinyl)benzenesulfonamide are excluded.

As another preferred embodiment of Compound (I), mention may be made of compounds wherein

ring B², ring B⁵, ring B¹¹and ring B¹⁴, which may be identical or different, are further substituted with (a) C_6-14aryl which may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen, (b) cyano, (c) hydroxy, (d) carboxy, (e) nitro, (f) C_1-6alkyl which may be substituted with di-C_1-6alkylamino, (g) C_1-6alkoxy, (h) C_1-6alkylcarbonyloxy, (i) C_1-6alkylthio, (j) C_1-6alkylsulfinyl, (k) C_1-6alkylsulfonyl, (l) halogen, (m) amino, (n) mono-C_1-6alkylamino, (o) di-C_1-6alkylamino, (p) a 5-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5-membered ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (q) a 6-membered ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 6-membered ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (r) a bicyclic or tricyclic fused ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this bicyclic or tricyclic fused ring group may be substituted with 1 to 3 substituents selected from (i) hydroxy, (ii) amino, (iii) mono-C_1-6alkylamino, (iv) di-C_1-6alkylamino, (v) C_1-6alkoxy and (vi) halogen), (s) C_1-6alkoxycarbonyl, (t) carbamoyl, (u) N-mono-C_1-6alkylcarbamoyl, (v) N,N-di-C_1-6alkylcarbamoyl, and (w) C_1-2alkylenedioxy (hereinafter (a)-(w) are briefly referred to as Substituent Group A);

Z², Z⁵, Z⁷, Z⁸, Z¹¹, Z¹⁴, Z¹⁶and Z¹⁷, which may be identical or different, are each C_1-6alkylene which may be substituted or a bond;

R⁷, R¹³, R¹⁷, R¹⁹, R²⁷, R³³, R³⁷and R³⁹, which may be identical or different, are each (a) C_1-10alkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (b) C_6-14aryl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (c) a 5- or 6-membered aromatic ring group containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and the like in addition to carbon atoms (wherein this 5- or 6-membered ring may be substituted with a substituent selected from the Substituent Group A); or

R⁶and R⁷, R¹²and R¹³, R¹⁶and R¹⁷, R¹⁸and R¹⁹, R²⁶and R²⁷, R³²and R³³, R³⁶and R³⁷, and R³⁸and R³⁹may respectively form a ring together with the adjacent nitrogen atom.

As another preferred embodiment of Compound (I), mention may be made of compounds wherein

ring A is a benzene ring; X is an oxygen atom or NH; R¹is a hydrogen atom or C_1-6alkyl;

ring B², ring B⁵, ring B¹¹and ring B¹⁴may be identical or different, and are each a benzene ring which may be further substituted with one substituent selected from halogen (e.g., a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.), lower alkyl (e.g., C_1-6alkyl, etc.) and cyano;

ring B⁷, ring B⁸, ring B¹⁶and ring B¹⁷may be identical or different, and are each a thiophene ring or furan ring which may be further substituted;

Z², Z⁵, Z⁷, Z⁸, Z¹¹, Z¹⁴, Z¹⁶and Z¹⁷may be identical or different, and are each C_1-6alkylene which may be substituted or a bond;

R⁶, R¹², R¹⁶, R¹⁸, R²⁶, R³², R³⁶and R³⁸may be identical or different, and are each C_1-6alkyl which may be substituted with cyano; and

R⁷, R¹³, R¹⁷, R¹⁹, R²⁷, R³³, R³⁷and R³⁹may be identical or different, and are each (a) C_1-10alkyl which may be substituted with 1 to 3 substituents selected from the Substituent Group A, (b) C_6-14aryl which may be substituted with halogen, or (c) pyridyl; or

R⁶and R⁷, R¹²and R¹³, R¹⁶and R¹⁷, R¹⁸and R¹⁹, R²⁶and R²⁷, R³²and R³³, R³⁶and R³⁷, and R³⁸and R³⁹may respectively form, together with the adjacent nitrogen atom, (1) 1,2,3,4-tetrahydroquinolin-1-yl which may be substituted with C_1-6alkyl, halogen (e.g., a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.) or C_1-6alkoxy, (2) 2,3-dihydro-1H-indol-1-yl which may be substituted with C_1-6alkyl, (3) 2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl which may be substituted with C_1-6alkyl, or (4) 3,4-dihydro-2H-1,4-benzoxazin-1-yl.

In particular, Compound (I) wherein X is NH and R¹is a hydrogen atom, is preferred.

Further, Compound (I) wherein ring B², ring B⁵, ring B¹¹and ring B¹⁴, which may be identical or different, are each a benzene ring which may be further substituted with one chlorine atom, is preferred, and Compound (I) wherein the above-mentioned rings are each an unsubstituted benzene ring, is particularly preferred.

Furthermore, Compound (I) wherein ring B⁷, ring B⁸, ring B¹⁶and ring B¹⁷, which may be identical or different, are each a thiophene ring or furan ring which may be further substituted with one substituent selected from halogen, cyano and methyl, is preferred, and Compound (I) wherein the above-mentioned rings are each a thiophene ring or furan ring which may be substituted with one substituent selected from a chlorine atom and cyano, is particularly preferred.

As another preferred embodiment of Compound (I), mention may be made of compounds wherein Z², Z⁵, Z⁷, Z⁸, Z¹¹, Z¹⁴, Z¹⁶and Z¹⁷are each a bond.

As another preferred embodiment of Compound (I), for example, mention may be made of Compound (I) wherein ring A is a benzene ring; X is an oxygen atom or NH; R¹is a hydrogen atom or C_1-6alkyl; R²is

(1) a group represented by the formula:
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[wherein ring B^2″ is a benzene ring which may be further substituted with halogen, R^6″ is C_1-6alkyl which may be substituted with cyano, and R^7″ is C_6-14aryl or pyridyl which may be substituted with halogen, or R^6″ and R^7″ form, together with the adjacent nitrogen atom, (1) 1,2,3,4-tetrahydroquinolin-1-yl which may be substituted with C_1-6alkyl, halogen or C_1-6alkoxy, (2) 2,3-dihydro-1H-indol-1-yl which may be substituted with C_1-6alkyl, (3) 2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl which may be substituted with C_1-6alkyl, or (4) 3,4-dihydro-2H-1,4-benzoxazin-1-yl],

(2) a group represented by the formula:
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[wherein ring B^5″ is a benzene ring which may be further substituted with halogen, R^12″ is C_1-6alkyl which may be substituted with cyano, and R^13″ is C_6-14aryl or pyridyl which may be substituted with halogen, or R^12″ and R^13″ form, together with the adjacent nitrogen atom, (1) 1,2,3,4-tetrahydroquinolin-1-yl which may be substituted with C_1-6alkyl, halogen or C_1-6alkoxy, (2) 2,3-dihydro-1H-indol-1-yl which may be substituted with C_1-6alkyl, (3) 2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl which may be substituted with C_1-6alkyl, or (4) 3,4-dihydro-2H-1,4-benzoxazin-1-yl], or

(3) a group represented by the formula:
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[wherein ring B^7″ is a thiophene ring which may be further substituted with halogen, R^16″ is C_1-6alkyl which may be substituted with cyano, and R^17″ is C_6-14aryl or pyridyl which may be substituted with halogen, or R^16″ and R^17″ form, together with the adjacent nitrogen atom, (1) 1,2,3,4-tetrahydroquinolin-1-yl which may be substituted with C_1-6alkyl, halogen or C_1-6alkoxy, (2) 2,3-dihydro-1H-indol-1-yl which may be substituted with C_1-6alkyl, (3) 2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl which may be substituted with C_1-6alkyl, or (4) 3,4-dihydro-2H-1,4-benzoxazin-1-yl], or the like.

More specifically, mention may be made of

3-(2-chloro-5-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)phenyl)quinazoline-2,4(1H,3H)-dione,

4-chloro-3-(2,4-dioxo-1,4-dihydro-3(2H)-quinazolinyl)-N-methyl-N-2-pyridinylbenzenesulfonamide,

3-(2-chloro-5-((2-methyl-3,4-dihydro-1(2H)-quinolinyl)sulfonyl)phenyl)-2,4(1H,3H)-quinazolinedione,

3-(2-chloro-5-(2,3-dihydro-4H-1,4-benzoxazin-4-ylsulfonyl)phenyl)-2,4(1H,3H)-quinazolinedione,

3-(2-chloro-5-(2,3,4,5-tetrahydro-1H-1-benzazepin-1-ylsulfonyl)phenyl)-2,4(1H,3H)-quinazolinedione,

3-(2-chloro-5-(3,4-dihydro-1,5-benzoxazepin-5(2H)-ylsulfonyl)phenyl)-2,4(1H,3H)-quinazolinedione,

4-chloro-3-(4-imino-2-oxo-1,4-dihydro-3(2H)-quinazolinyl)-N-methyl-N-phenylbenzenesulfonamide trifluoroacetate,

3-(2-chloro-5-(3,4-dihydro-1(2H)-quinolinylsulfonyl)phenyl)-4-imino-3,4-dihydro-2(1H)-quinazolinone trifluoroacetate,

3-(2-chloro-5-(2,3-dihydro-1H-indol-1-ylsulfonyl)phenyl)-4-imino-3,4-dihydro-2(1H)-quinazolinone,

3-(2-chloro-5-(3,4-dihydro-1(2H)-quinolinylcarbonyl)phenyl)-2,4(1H,3H)-quinazolinedione and the like.

More preferred compounds are

3-(2-chloro-5-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)phenyl)quinazoline-2,4(1H,3H)-dione,

4-chloro-3-(2,4-dioxo-1,4-dihydro-3(2H)-quinazolinyl)-N-methyl-N-2-pyridinylbenzenesulfonamide trifluoroacetate,

3-(2-chloro-5-(2,3,4,5-tetrahydro-1H-1-benzazepin-1-ylsulfonyl)phenyl)-2,4(1H,3H)-quinazolinedione,

3-(2-chloro-5-(3,4-dihydro-1,5-benzoxazepin-5(2H)-ylsulfonyl)phenyl)-2,4(1H,3H)-quinazolinedione,

4-chloro-3-(4-imino-2-oxo-1,4-dihydro-3(2H)-quinazolinyl)-N-methyl-N-phenylbenzenesulfonamide trifluoroacetate, and

3-(2-chloro-5-(3,4-dihydro-1(2H)-quinolinylsulfonyl)phenyl)-4-imino-3,4-dihydro-2(1H)-quinazolinone trifluoroacetate.

For salts of Compound (I), salts of Compound (I) are preferably physiologically acceptable acid addition salts. Examples of such salt include salts with inorganic acids (e.g., hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid, etc.), or salts with organic acids (e.g., formic acid, acetic acid, trifluoroacetic acid (TFA), fumaric acid, oxalic acid, tartaric acid, maleic acid, citric acid, succinic acid, malic acid, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, etc.), and the like. When Compound (I) has an acidic group, the compound may form a physiologically acceptable salt with an inorganic base (e.g., alkali metals or alkaline earth metals such as sodium, potassium, calcium and magnesium, ammonia, etc.), or an organic base (e.g., trimethylamine, triethylamine, pyridine, picoline, ethanolamine, diethanolamine, triethanolamine, dicyclohexylamine, N,N′-dibenzylethylenediamine, etc.).

Compound (I) or a salt thereof is particularly preferably

3-[5-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)-2-fluorophenyl]quinazoline-2,4(1H,3H)-dione,