JP2009522239A - Triterpene quinones and triterpene phenol derivatives and their application for the treatment of tumors and parasitic diseases - Google Patents

Abstract

  The present invention relates to triterpene quinone and triterpene phenol derivatives as selective blockers of choline kinase enzymes, pharmaceutically acceptable salts, prodrugs, solvates or stereoisomers thereof, pharmaceutical compositions containing them, tumors And their use in the treatment of parasitic diseases or diseases caused by viruses, bacteria or fungi.

Description

Background of the Invention

FIELD OF THE INVENTION The present invention generally blocks phosphorylcholine biosynthesis by selective blockade of choline kinase enzymes in tumor cells or cells affected by parasitic infections, and thus tumors and parasites in animals, including humans. The present invention relates to triterpene quinone and triterpene phenol derivatives and methods for producing the compounds according to the invention, applicable to the treatment of diseases or diseases caused by viruses, bacteria and fungi.

BACKGROUND OF THE INVENTION Choline kinase is the first enzyme in the Kennedy pathway or the phosphatidylcholine (PC) synthesis pathway, using adenosine 5'-triphosphate (ATP) as the phosphate group donor, and converting choline to phosphorylcholine (PCho). Phosphorylates. The Ras gene has been widely studied because it constitutes a family of so-called oncogenes and is activated in 25-30% of all human tumors and in 90% of severe ones. Ras proteins play an important role in intracellular signal transduction by participating in the regulation of cell proliferation, terminal differentiation and senescence. Among the malignant transformations mediated by various oncogenes, the ras oncogene is prominent and induces high levels of choline kinase activity, resulting in an abnormal increase in the intracellular level of the product PCho. Supplementary facts are also due to the fact that studies using nuclear magnetic resonance (NMR) technology have shown higher PCho levels than normal tissues, especially in human tumor tissues including breast cancer, colon cancer, lung cancer and prostate cancer This supports the role of ChoK in human tumor tissue. ras is one of the most studied oncogenes in human carcinogenesis and that ChoK inhibition is a new and effective anti-tumor strategy in cells malignantly transformed by oncogenes What is shown is a general view. These initial findings were then postulated in nude mice in vivo.

  In light of these data, the design of compounds that directly affect choline kinase activity, or enzymes that are activated by phosphorylcholine in an individual or combined manner will enable the development of effective antitumor therapies. .

  In this sense, hemicolinium-3 (HC-3) has been identified as a relatively potent and selective substance in the study of ChoK inhibitors [Cuadrado A., Carnero A., Dolfi F., Jimenez B. and Lacal JC Oncogene 8, 2959-2968 (1993); Jimenez B., del Peso L., Montaner S., Esteve P. and Lacal JCJ Cell Biochem. 57, 141-149 (1995); Hernandez-Alcoceba, R., Saniger, L., Campos, J., Nunez, MC, Khaless, F., Gallo, MA, Espinosa, A., Lacal, JC Oncogene, 15, 2289-2301 (1997)]. This choline homologue with a biphenyl structure has been used to design new anti-tumor drugs, but again, because HC-3 is a powerful respiratory palsy, for use in clinical settings Not a good candidate. The synthesis of some derivatives has been based on structural modifications of HC-3 that enhance the inhibitory activity of the ChoK enzyme and partially eliminate its toxic effects.

  Bis quaternized symmetrical compounds derived from pyridinium have also been used and their ability to inhibit PCho production in whole cells has been evaluated (WO 98/05644). However, these derivatives have a high level of toxicity that limits the expansion of therapeutic applications.

  On the other hand, compounds called celastrol and pristimelin formed by a pentacyclic triterpene structure are known to induce apoptosis, and this activity has been demonstrated in a human leukemia model [Nagase, M., Oto, J. Sugiyama, S., Yube, K., Takaishi, and Sakato, N., Biosci. Biotechnol. Biochem 67, 1883 (2003)]. However, again, these compounds show severe toxicity at the cellular level, making their development as agents in the treatment of tumor symptoms impossible. In this sense, patent application US 2004/0220267 describes celastrol and pristimeline derivatives that can ameliorate the toxicity problem.

  However, there is a strong need to develop compounds that provide high inhibitory activity of ChoK enzymes for the purpose of enabling use in the treatment of tumors and at the same time significantly reduce the toxicity of current compounds in the art. Yes.

Summary of the Invention

  As a result of intensive investigations, the present inventors have shown that blockade of biosynthesis of phosphorylcholine by selective blockade of the choline kinase (ChoK) enzyme by specific modifications in the structure of the previously described compounds celastrol and pristimelin. It has been found that it is possible to provide a compound that acts as a novel and effective anti-tumor strategy in human tumor cells.

［式中、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_７、Ｒ_８、Ｒ_１１およびＲ_１２は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ’）（Ｒ’’）アミノ基（ここで、Ｒ’およびＲ’’は独立に水素またはＣ_１−Ｃ_１２アルキル基である）；ＯＣＯＲ基（ここで、Ｒは（ＣＨ_２）_２ＣＯＯＨまたは（ＣＨ_２）_２ＣＯ_２ＣＨ_２ＣＨ_３である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_９およびＲ_１０は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ’’’基｛ここで、Ｒ’’’は水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｏ−Ｃ_１−Ｃ_１２アルキル；またはＮ（Ｒ^ＩＶ）（Ｒ^Ｖ）アミノ（ここで、Ｒ^ＩＶおよびＲ^Ｖは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；（ＣＨ_２）_ｎ−ＯＨカルビノール基（ここで、ｎは１〜１０の間の整数である）であるか；あるいは一緒にメチレン基を形成し；
結合

は二重結合または単結合を意味し；
三環式構造

は、下記の構造：

から選択され、ここで、
Ｒ_１３、Ｒ_１４、Ｒ_１５、Ｒ_１６、Ｒ_２１、Ｒ_２２およびＲ_２３は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＶＩ）（Ｒ^ＶＩＩ）アミノ基（ここで、Ｒ^ＶＩおよびＲ^ＶＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；ＯＣＯＲ^ＶＩＩＩ基（ここで、Ｒ^ＶＩＩＩは（ＣＨ_２）_２ＣＯＯＨまたは（ＣＨ_２）_２ＣＯ_２ＣＨ_２ＣＨ_３である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができるか、または各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_１７は水素またはメチルであり；
Ｒ_１８およびＲ_１８’は独立に水素；ヒドロキシル；ハロゲン；Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＩＸ｛ここで、Ｒ^ＩＸは水素；ヒドロキシル；Ｃ_１−Ｃ_１２アルキル；Ｎ（Ｒ^Ｘ）（Ｒ^ＸＩ）アミノ（ここで、Ｒ^ＸおよびＲ^ＸＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；またはＣ_１−Ｃ_１２アルコキシルである｝；またはトリフルオロメチルであり；
Ｒ_１９、Ｒ_１９’、Ｒ_２０およびＲ_２０’は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_{１０アリール；またはＮ（Ｒ} ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；トリフルオロメチルであるか；あるいは各１９−１９’または２０−２０’対は、それらが結合している炭素と一緒にＣ＝Ｏ基を形成することができ；
Ｒ_２４およびＲ_２５は独立に水素、ヒドロキシルまたはハロゲンである］
の化合物、またはその薬学上許容される塩、誘導体、プロドラッグ、溶媒和物もしくは立体異性体の使用に関する。 Thus, in one embodiment, the invention provides a compound of formula (I) in the manufacture of a medicament for the treatment and / or prevention of a disease or condition mediated by ChoK:

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or an unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); Where R is (CH ₂ ) ₂ COOH or (CH ₂ ) ₂ CO ₂ CH ₂ CH ₃ ; or each pair together with the carbon to which they are attached (C═O ) Groups can be formed;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
Join

Means a double bond or a single bond;
Tricyclic structure

Has the following structure:

Where
R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₂₁ , R ₂₂ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl N (R ^VI ) (R ^VII ) amino group (where R ^VI and R ^VII are independently hydrogen or a C ₁ -C ₁₂ alkyl group); OCOR ^VIII group (where R ^VIII is (CH ₂ ) ₂ COOH or (CH ₂ ) ₂ CO ₂ CH ₂ CH ₃ ); or is each pair capable of forming a (C═O) group with the carbon to which they are attached? Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₁₇ is hydrogen or methyl;
R ₁₈ and R _{18 ′} are independently hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (where R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl Yes;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C _{10 aryl; or N (R} ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ and R ₂₅ are independently hydrogen, hydroxyl or halogen]
Or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof.

［式中、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_９、Ｒ_１０、Ｒ_１１、Ｒ_１２、Ｒ_１３、Ｒ_１４、Ｒ_１５、Ｒ_１６、Ｒ_１７、Ｒ_１８、Ｒ_１９およびＲ_２０は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（ＲＸ^ＸＶ）（Ｒ^ＸＶＩ）アミノ基（ここで、Ｒ^ＸＶおよびＲ^ＸＶＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒にカルボキシル（Ｃ＝Ｏ）基を形成することができ；
Ｒ_７およびＲ_８は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＸＶＩＩ基｛ここで、Ｒ^ＸＶＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｏ−Ｃ_１−Ｃ_１２アルキル；またはＮ（Ｒ^{ＸＶＩＩＩ}）（Ｒ^ＸＩＸ）アミノ（ここで、Ｒ^{ＸＶＩＩＩ}およびＲ^ＸＩＸは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；（ＣＨ_２）_ｎ−ＯＨカルビノール基（ここで、ｎは１〜１０の間の整数である）であるか；あるいは一緒にメチレン基を形成し、
Ｒ_２１およびＲ_２４は独立に置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＸ基｛ここで、Ｒ^ＸＸは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＸＩ）（Ｒ^ＸＸＩＩ）アミノ（ここで、Ｒ^ＸＸＩおよびＲ^ＸＸＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１〜３の間である）；またはトリフルオロメチルであり；
Ｒ_２２およびＲ_２３は、
Ｒ_２４がＲ_２０に対してパラ位にある場合には、水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^{ＸＸＩＩＩ}基｛ここで、Ｒ^{ＸＸＩＩＩ}は水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＸＩＶ）（Ｒ^ＸＸＶ）アミノ（ここで、Ｒ^ＸＸＩＶおよびＲ^ＸＸＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１〜３の間である）；またはトリフルオロメチルであるか；あるいは
Ｒ_２４がＲ_２０に対してメタ位にある場合には、それぞれＯＲ_２２’およびＯＲ_２３’（ここで、Ｒ_２２’およびＲ_２３’は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＸＶＩ基｛ここで、Ｒ^ＸＸＶＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^{ＸＸＶＩＩ}）（Ｒ^{ＸＸＶＩＩＩ}）アミノ（ここで、Ｒ^{ＸＸＶＩＩ}およびＲ^{ＸＸＶＩＩＩ}は独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；またはトリフルオロメチルである］
の化合物、またはその薬学上許容される塩、誘導体、プロドラッグ、溶媒和物もしくは立体異性体の使用に関する。 In another aspect, the invention provides a compound of formula (II) in the manufacture of a medicament for the treatment and / or prevention of a disease or condition mediated by ChoK:

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₉ , R ₁₀ , R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₁₇ , R ₁₈ , R ₁₉ And R ₂₀ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (RX ^XV ) (R ^XVI ) amino group (where R or ^XV and R ^XVI are are independently hydrogen or C ₁ -C ₁₂ alkyl group); or each pair, to form them bonded to and carboxyl (C = O) group together with the carbon Can;
R ₇ and R ₈ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^XVII group {where R ^XVII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted _C 6 _{-C 10 aryl; O-C} 1 _{-C 12} alkyl; with or ^{N (R XVIII) (R XIX} ) amino ^{(wherein, R XVIII} and ^{R XIX} are independently hydrogen or _{C 1} Is a —C ₁₂ alkyl group)}; (CH ₂ ) _n —OH carbinol group (where n is an integer between 1 and 10); or together forms a methylene group. ,
R ₂₁ and R ₂₄ are independently substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XX group {where R ^XX is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ —C ₁₀ aryl; or N (R ^XXI ) (R ^XXII ) amino, where R ^XXI and R ^XXII are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂₎ alkyl _-O- (C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 to 3); or trifluoromethyl;
R ₂₂ and R ₂₃ are
When R ₂₄ is para to R ₂₀ , hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XXIII group {where R ^XXIII is hydrogen; hydroxyl; substituted or unsubstituted C _1- C ₁₂ alkyl; substituted or unsubstituted _C 6 _{-C 10} aryl; or ^N (R ^{XXIV) (R XXV)} amino ^{(wherein, R XXIV} and ^{R XXV} are independently hydrogen or _C 1 _{-C 12} alkyl group) Or [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); or is trifluoromethyl? Or when R ₂₄ is in the meta position relative to R ₂₀ , OR ₂₂ ′ and OR ₂₃ ′ (wherein R ₂₂ ′ and R ₂₃ ′ are independently hydrogen; Substituted C ₁ -C ₁₂ alkyl; COR ^XXVI group (where R ^XXVI is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XXVII ) (R ^XXVIII ) amino (where R ^XXVII and R ^XXVIII are independently hydrogen or a C ₁ -C ₁₂ alkyl group)}; [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); or trifluoromethyl]
Or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof.

  In certain embodiments, the disease or condition is cancer. In another specific embodiment, the disease is a parasitic disease. In yet another specific embodiment, the disease is a bacterial disease. Finally, in yet another specific embodiment, the disease is a fungal disease.

［式中、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_７、Ｒ_８、Ｒ_１１およびＲ_１２は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ’）（Ｒ’’）アミノ基（ここで、Ｒ’およびＲ’’は独立に水素またはＣ_１−Ｃ_１２アルキル基である）；ＯＣＯＲ基（ここで、Ｒは（ＣＨ_２）_２ＣＯＯＨまたは（ＣＨ_２）_２ＣＯ_２ＣＨ_２ＣＨ_３である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_９およびＲ_１０は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ’’’基｛ここで、Ｒ’’’は水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｏ−Ｃ_１−Ｃ_１２アルキル；またはＮ（Ｒ^ＩＶ）（Ｒ^Ｖ）アミノ（ここで、Ｒ^ＩＶおよびＲ^Ｖは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；（ＣＨ_２）_ｎ−ＯＨカルビノール基（ここで、ｎは１〜１０の間の整数である）であるか；あるいは一緒にメチレン基を形成し；
結合

は二重結合または単結合を意味し；
三環式構造

は、下記の構造：

から選択され、ここで、
Ｒ_１３、Ｒ_１４、Ｒ_１５、Ｒ_１６、Ｒ_２１、Ｒ_２２およびＲ_２３は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＶＩ）（Ｒ^ＶＩＩ）アミノ基（ここで、Ｒ^ＶＩおよびＲ^ＶＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；ＯＣＯＲ^ＶＩＩＩ基（ここで、Ｒ^ＶＩＩＩは（ＣＨ_２）_２ＣＯＯＨまたは（ＣＨ_２）_２ＣＯ_２ＣＨ_２ＣＨ_３である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができるか、または各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_１７は水素またはメチルであり；
Ｒ_１８およびＲ_１８’は独立に水素；ヒドロキシル；ハロゲン；Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＩＸ｛ここで、Ｒ^ＩＸは水素；ヒドロキシル；Ｃ_１−Ｃ_１２アルキル；Ｎ（Ｒ^Ｘ）（Ｒ^ＸＩ）アミノ（ここで、Ｒ^ＸおよびＲ^ＸＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；またはＣ_１−Ｃ_１２アルコキシルである｝；またはトリフルオロメチルであり；
Ｒ_１９、Ｒ_１９’、Ｒ_２０およびＲ_２０’は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；トリフルオロメチルであるか；あるいは各１９−１９’または２０−２０’対は、それらが結合している炭素と一緒にＣ＝Ｏ基を形成することができ；
Ｒ_２４およびＲ_２５は独立に水素、ヒドロキシルまたはハロゲンである］
の化合物、またはその薬学上許容される塩、誘導体、プロドラッグ、溶媒和物もしくは立体異性体
［ただし、
三環式構造が（ａ）である場合、式（Ｉ）の化合物は、
１０−ヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−１１−オキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−２−カルボン酸；
１０−ヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−１１−オキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−２−カルボン酸メチルエステル；
３，１０−ジヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−１１−オキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−２−カルボン酸メチルエステル；
３−ヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−７，８，８ａ，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−デカヒドロ−６ｂＨ，９Ｈ−ピセン−２，１０−ジオン；
３，９−ジヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−７，８，８ａ，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−デカヒドロ−６ｂＨ，９Ｈ−ピセン−２，１０−ジオン；
３，７，９−トリヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−７，８，８ａ，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−デカヒドロ−６ｂＨ，９Ｈ−ピセン−２，１０−ジオン；
１４−ブロモ−３，７，９−トリヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−７，８，８ａ，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−デカヒドロ−６ｂＨ，９Ｈ−ピセン−２，１０−ジオン；
コハク酸モノ−（１０−ヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−３，１１−ジオキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−４−イル）エステル；
コハク酸エチルエステル１０−ヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−３，１１−ジオキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−４−イルエステル；
酢酸９−ヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−２，１０−ジオキソ−２，６ｂ，７，８，８ａ，９，１０，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−テトラデカヒドロ−ピセン−３−イルエステル；
ドデカン酸９−ヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−２，１０−ジオキソ−２，６ｂ，７，８，８ａ，９，１０，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−テトラデカヒドロ−ピセン−３−イルエステル；
ジメチル−カルバミン酸９−ヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−２，１０−ジオキソ−２，６ｂ，７，８，８ａ，９，１０，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−テトラデカヒドロ−ピセン−３−イルエステル；
ニコチン酸９−ヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−２，１０−ジオキソ−２，６ｂ，７，８，８ａ，９，１０，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−テトラデカヒドロ−ピセン−３−イルエステル；
３，１０−ジヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−１１−オキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−２−カルボン酸メチルエステル；
１０−ヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−１１−オキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−２−カルボン酸メチルエステル
でなく、
三環式構造が（ｂ）であり、Ｒ_１９およびＲ_２０が独立に水素またはアシル基である場合、
Ｒ_５はヒドロキシルであるか；または
Ｒ_２１およびＲ_２２はそれらが結合している炭素と一緒にＣ＝Ｏ基を形成し、Ｒ_１０はＣＯＯＨでなく、
三環式構造が（ｃ）であり、Ｒ_１９およびＲ_２０が双方ともＣＨ_３である場合、Ｒ_１５およびＲ_１６はそれらが結合している炭素と一緒にＣ＝Ｏ基を形成しない］
に関する。 In another aspect, the present invention provides compounds of general formula (I):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or an unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); Where R is (CH ₂ ) ₂ COOH or (CH ₂ ) ₂ CO ₂ CH ₂ CH ₃ ; or each pair together with the carbon to which they are attached (C═O ) Groups can be formed;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
Join

Means a double bond or a single bond;
Tricyclic structure

Has the following structure:

Where
R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₂₁ , R ₂₂ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl N (R ^VI ) (R ^VII ) amino group (where R ^VI and R ^VII are independently hydrogen or a C ₁ -C ₁₂ alkyl group); OCOR ^VIII group (where R ^VIII is (CH ₂ ) ₂ COOH or (CH ₂ ) ₂ CO ₂ CH ₂ CH ₃ ); or is each pair capable of forming a (C═O) group with the carbon to which they are attached? Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₁₇ is hydrogen or methyl;
R ₁₈ and R _{18 ′} are independently hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (where R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl Yes;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ and R ₂₅ are independently hydrogen, hydroxyl or halogen]
Or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof [wherein
When the tricyclic structure is (a), the compound of formula (I) is
10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b- Tetradecahydro-picene-2-carboxylic acid;
10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b- Tetradecahydro-picene-2-carboxylic acid methyl ester;
3,10-dihydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester;
3-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene-2,10- Dione;
3,9-dihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene-2, 10-dione;
3,7,9-trihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene -2,10-dione;
14-bromo-3,7,9-trihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH , 9H-picene-2,10-dione;
Succinic acid mono- (10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-3,11-dioxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13 , 14, 14a, 14b-tetradecahydro-picen-4-yl) ester;
Succinic acid ethyl ester 10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-3,11-dioxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13, 14,14a, 14b-tetradecahydro-picen-4-yl ester;
Acetic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14 , 14a-tetradecahydro-picen-3-yl ester;
Dodecanoic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13, 14,14a-tetradecahydro-picen-3-yl ester;
Dimethyl-carbamic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-tetradecahydro-picen-3-yl ester;
Nicotinic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13, 14,14a-tetradecahydro-picen-3-yl ester;
3,10-dihydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester;
10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b- Not tetradecahydro-picene-2-carboxylic acid methyl ester,
When the tricyclic structure is (b) and R ₁₉ and R ₂₀ are independently hydrogen or an acyl group,
R ₅ is hydroxyl; or R ₂₁ and R ₂₂ together with the carbon to which they are attached form a C═O group, R ₁₀ is not COOH,
When the tricyclic structure is (c) and R ₁₉ and R ₂₀ are both CH ₃ , R ₁₅ and R ₁₆ do not form a C═O group with the carbon to which they are attached]
About.

［式中、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_９、Ｒ_１０、Ｒ_１１、Ｒ_１２、Ｒ_１３、Ｒ_１４、Ｒ_１５、Ｒ_１６、Ｒ_１７、Ｒ_１８、Ｒ_１９およびＲ_２０は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（ＲＸ^ＸＶ）（Ｒ^ＸＶＩ）アミノ基（ここで、Ｒ^ＸＶおよびＲ^ＸＶＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒にカルボキシル（Ｃ＝Ｏ）基を形成することができ；
Ｒ_７およびＲ_８は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＸＶＩＩ基｛ここで、Ｒ^ＸＶＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｏ−Ｃ_１−Ｃ_１２アルキル；またはＮ（Ｒ^{ＸＶＩＩＩ}）（Ｒ^ＸＩＸ）アミノ（ここで、Ｒ^{ＸＶＩＩＩ}およびＲ^ＸＩＸは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；（ＣＨ_２）_ｎ−ＯＨカルビノール基（ここで、ｎは１〜１０の間の整数である）であるか；あるいは一緒にメチレン基を形成し、
Ｒ_２１およびＲ_２４は独立に置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＸ基｛ここで、Ｒ^ＸＸは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＸＩ）（Ｒ^ＸＸＩＩ）アミノ（ここで、Ｒ^ＸＸＩおよびＲ^ＸＸＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１〜３の間である）；またはトリフルオロメチルであり；
Ｒ_２２およびＲ_２３は、
Ｒ_２４がＲ_２０に対してパラ位にある場合には、水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^{ＸＸＩＩＩ}基｛ここで、Ｒ^{ＸＸＩＩＩ}は水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＸＩＶ）（Ｒ^ＸＸＶ）アミノ（ここで、Ｒ^ＸＸＩＶおよびＲ^ＸＸＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１〜３の間である）；またはトリフルオロメチルであるか；あるいは
Ｒ_２４がＲ_２０に対してメタ位にある場合には、それぞれＯＲ_２２’およびＯＲ_２３’であり、ここで、Ｒ_２２’およびＲ_２３’は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＸＶＩ基｛ここで、Ｒ^ＸＸＶＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^{ＸＸＶＩＩ}）（Ｒ^{ＸＸＶＩＩＩ}）アミノ（ここで、Ｒ^{ＸＸＶＩＩ}およびＲ^{ＸＸＶＩＩＩ}は独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；またはトリフルオロメチルである］
の化合物、またはその薬学上許容される塩、誘導体、プロドラッグ、溶媒和物もしくは立体異性体に関する。 In another aspect, the present invention provides a compound of formula (II):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₉ , R ₁₀ , R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₁₇ , R ₁₈ , R ₁₉ And R ₂₀ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (RX ^XV ) (R ^XVI ) amino group (where R or ^XV and R ^XVI are are independently hydrogen or C ₁ -C ₁₂ alkyl group); or each pair, to form them bonded to and carboxyl (C = O) group together with the carbon Can;
R ₇ and R ₈ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^XVII group {where R ^XVII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted _C 6 _{-C 10 aryl; O-C} 1 _{-C 12} alkyl; with or ^{N (R XVIII) (R XIX} ) amino ^{(wherein, R XVIII} and ^{R XIX} are independently hydrogen or _{C 1} Is a —C ₁₂ alkyl group)}; (CH ₂ ) _n —OH carbinol group (where n is an integer between 1 and 10); or together forms a methylene group. ,
R ₂₁ and R ₂₄ are independently substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XX group {where R ^XX is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ —C ₁₀ aryl; or N (R ^XXI ) (R ^XXII ) amino, where R ^XXI and R ^XXII are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂₎ alkyl _-O- (C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 to 3); or trifluoromethyl;
R ₂₂ and R ₂₃ are
When R ₂₄ is para to R ₂₀ , hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XXIII group {where R ^XXIII is hydrogen; hydroxyl; substituted or unsubstituted C _1- C ₁₂ alkyl; substituted or unsubstituted _C 6 _{-C 10} aryl; or ^N (R ^{XXIV) (R XXV)} amino ^{(wherein, R XXIV} and ^{R XXV} are independently hydrogen or _C 1 _{-C 12} alkyl group) Or [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); or is trifluoromethyl? Or, when R ₂₄ is in the meta position relative to R ₂₀ , OR ₂₂ ′ and OR ₂₃ ′, respectively, where R ₂₂ ′ and R ₂₃ ′ are independently hydrogen; Here ^{COR XXVI} group ^{{, R XXVI} is ^hydrogen; unsubstituted _C 1 _{-C 12} alkyl hydroxyl; substituted or unsubstituted _C 1 _{-C 12} alkyl; substituted or unsubstituted _C 6 _{-C 10} aryl; or N (R ^XXVII ) (R ^XXVIII ) amino where R ^XXVII and R ^XXVIII are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl-O- (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); or trifluoromethyl]
Or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof.

  In another aspect, the invention provides a compound of formula (I) or a compound of formula (II), or a mixture thereof, or a pharmaceutically acceptable salt, derivative, prodrug, solvate thereof for administration to a patient. Or a stereoisomer is intended for use with a pharmaceutically acceptable carrier, adjuvant or vehicle.

Detailed description of the invention

［式中、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_７、Ｒ_８、Ｒ_１１およびＲ_１２は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ’）（Ｒ’’）アミノ基（ここで、Ｒ’およびＲ’’は独立に水素またはＣ_１−Ｃ_１２アルキル基である）；ＯＣＯＲ基（ここで、Ｒは（ＣＨ_２）_２ＣＯＯＨまたは（ＣＨ_２）_２ＣＯ_２ＣＨ_２ＣＨ_３である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_９およびＲ_１０は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ’’’基｛ここで、Ｒ’’’は水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｏ−Ｃ_１−Ｃ_１２アルキル；またはＮ（Ｒ^ＩＶ）（Ｒ^Ｖ）アミノ（ここで、Ｒ^ＩＶおよびＲ^Ｖは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；（ＣＨ_２）_ｎ−ＯＨカルビノール基（ここで、ｎは１〜１０の間の整数である）であるか；あるいは一緒にメチレン基を形成し；
結合

は二重結合または単結合を意味し；
三環式構造

は、下記の構造：

から選択され、ここで、
Ｒ_１３、Ｒ_１４、Ｒ_１５、Ｒ_１６、Ｒ_２１、Ｒ_２２およびＲ_２３は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＶＩ）（Ｒ^ＶＩＩ）アミノ基（ここで、Ｒ^ＶＩおよびＲ^ＶＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；ＯＣＯＲ^ＶＩＩＩ基（ここで、Ｒ^ＶＩＩＩは（ＣＨ_２）_２ＣＯＯＨまたは（ＣＨ_２）_２ＣＯ_２ＣＨ_２ＣＨ_３である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができるか、または各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_１７は水素またはメチルであり；
Ｒ_１８およびＲ_１８’は独立に水素；ヒドロキシル；ハロゲン；Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＩＸ｛ここで、Ｒ^ＩＸは水素；ヒドロキシル；Ｃ_１−Ｃ_１２アルキル；Ｎ（Ｒ^Ｘ）（Ｒ^ＸＩ）アミノ（ここで、Ｒ^ＸおよびＲ^ＸＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；またはＣ_１−Ｃ_１２アルコキシルである｝；またはトリフルオロメチルであり；
Ｒ_１９、Ｒ_１９’、Ｒ_２０およびＲ_２０’は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；トリフルオロメチルであるか；あるいは各１９−１９’または２０−２０’対は、それらが結合している炭素と一緒にＣ＝Ｏ基を形成することができ；
Ｒ_２４およびＲ_２５は独立に水素、ヒドロキシルまたはハロゲンである］
の化合物、またはその薬学上許容される塩、誘導体、プロドラッグ、溶媒和物もしくは立体異性体の使用である。 One object of the present invention is to formula (I) in the manufacture of a medicament for the treatment and / or prevention of a disease or condition mediated by ChoK:

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or an unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); Where R is (CH ₂ ) ₂ COOH or (CH ₂ ) ₂ CO ₂ CH ₂ CH ₃ ; or each pair together with the carbon to which they are attached (C═O ) Groups can be formed;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
Join

Means a double bond or a single bond;
Tricyclic structure

Has the following structure:

Where
R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₂₁ , R ₂₂ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl N (R ^VI ) (R ^VII ) amino group (where R ^VI and R ^VII are independently hydrogen or a C ₁ -C ₁₂ alkyl group); OCOR ^VIII group (where R ^VIII is (CH ₂ ) ₂ COOH or (CH ₂ ) ₂ CO ₂ CH ₂ CH ₃ ); or is each pair capable of forming a (C═O) group with the carbon to which they are attached? Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₁₇ is hydrogen or methyl;
R ₁₈ and R _{18 ′} are independently hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (where R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl Yes;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ and R ₂₅ are independently hydrogen, hydroxyl or halogen]
Or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof.

［式中、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_７、Ｒ_８、Ｒ_１１およびＲ_１２は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ’）（Ｒ’’）アミノ基（ここで、Ｒ’およびＲ’’は独立に水素またはＣ_１−Ｃ_１２アルキル基である）；ＯＣＯＲ基（ここで、Ｒは（ＣＨ_２）_２ＣＯＯＨまたは（ＣＨ_２）_２ＣＯ_２ＣＨ_２ＣＨ_３である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_９およびＲ_１０は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ’’’基｛ここで、Ｒ’’’は水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｏ−Ｃ_１−Ｃ_１２アルキル；またはＮ（Ｒ^ＩＶ）（Ｒ^Ｖ）アミノ（ここで、Ｒ^ＩＶおよびＲ^Ｖは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；（ＣＨ_２）_ｎ−ＯＨカルビノール基（ここで、ｎは１〜１０の間の整数である）であるか；あるいは一緒にメチレン基を形成し；
Ｒ_１３、Ｒ_１４、Ｒ_１５およびＲ_１６は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＶＩ）（Ｒ^ＶＩＩ）アミノ基（ここで、Ｒ^ＶＩおよびＲ^ＶＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；ＯＣＯＲ^ＶＩＩＩ基（ここで、Ｒ^ＶＩＩＩは（ＣＨ_２）_２ＣＯＯＨまたは（ＣＨ_２）_２ＣＯ_２ＣＨ_２ＣＨ_３である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_１７は水素またはメチルであり；
Ｒ_１８は水素；ヒドロキシル；ハロゲン；Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＩＸ｛ここで、Ｒ^ＩＸは水素；ヒドロキシル；Ｃ_１−Ｃ_１２アルキル；Ｎ（Ｒ^Ｘ）（Ｒ^ＸＩ）アミノ（ここで、Ｒ^ＸおよびＲ^ＸＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；またはＣ_１−Ｃ_１２アルコキシルである｝；またはトリフルオロメチルであり；
Ｒ_１９は水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；またはトリフルオロメチルであり；
結合

は二重結合または単結合を意味する］
の化合物である。 In a particular embodiment of the invention, the compound of formula (I) for use in the prevention and / or treatment of a disease or condition mediated by ChoK is a compound of formula (Ia):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or an unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); Where R is (CH ₂ ) ₂ COOH or (CH ₂ ) ₂ CO ₂ CH ₂ CH ₃ ; or each pair together with the carbon to which they are attached (C═O ) Groups can be formed;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
R ₁₃ , R ₁₄ , R ₁₅ and R ₁₆ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^VI ) (R ^VII ) Amino group (where R ^VI and R ^VII are independently hydrogen or a C ₁ -C ₁₂ alkyl group); OCOR ^VIII group (where R ^VIII is (CH ₂ ) ₂ COOH or (CH ₂ ) ₂ Each pair can form a (C═O) group with the carbon to which they are attached; or CO ₂ CH ₂ CH ₃ ;
R ₁₇ is hydrogen or methyl;
R ₁₈ is hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (wherein R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl;
R ₁₉ is hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ Aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl -O- _(C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 and 3); or trifluoromethyl;
Join

Means a double bond or a single bond]
It is this compound.

［式中、
Ｒ_５はヒドロキシルまたはＯＣＯＲ基であり、ここでＲは（ＣＨ_２）_２ＣＯＯＨまたは（ＣＨ_２）_２ＣＯ_２ＣＨ_２ＣＨ_３であり；
Ｒ_７およびＲ_８は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ’）（Ｒ’’）アミノ基（ここで、Ｒ’およびＲ’’は独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_１２は独立に水素またはハロゲンであり；かつ、
Ｒ_１９は水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩIは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１〜３の間である）；またはトリフルオロメチルであり；かつ、
結合

は、二重結合または単結合を意味する］
を有する構造を含んでなる。 In a preferred embodiment, the compound of formula (Ia) used in the present invention is of formula (Ia ′):

[Where:
R ₅ is a hydroxyl or OCOR group, where R is (CH ₂ ) ₂ COOH or (CH ₂ ) ₂ CO ₂ CH ₂ CH ₃ ;
R ₇ and R ₈ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (here R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or each pair forms a (C═O) group with the carbon to which they are attached. Can do;
R ₁₂ is independently hydrogen or halogen; and
R ₁₉ is hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ Aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl -O- _(C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 to 3); or trifluoromethyl; and,
Join

Means a double bond or a single bond]
The structure which has this.

As a specific example of this structure (Ia ′),
3,9-dihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene-2, 10-dione;
Acetic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14 , 14a-tetradecahydro-picen-3-yl ester;
9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14, 14a-tetradecahydro-picen-3-ylpropionic acid ester (C1);
Dodecanoic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13, 14,14a-tetradecahydro-picen-3-yl ester;
-Dimethyl-carbamic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b , 13,14,14a-tetradecahydro-picen-3-yl ester;
Nicotinic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13, 14,14a-tetradecahydro-picen-3-yl ester;
4-Bromo- (9-hydroxy-6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13 , 14,14a-tetradecahydro-picen-3-yl) benzoic acid ester (C2);
14-bromo-3,7,9-trihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH , 9H-picene-2,10-dione;
12-bromo-9-hydroxy-6b, 8a, 11, 12b, 14a-hexamethyl-2, 10-dioxo-2, 6b, 7, 8, 8a, 9, 10, 11, 12, 12a, 12b, 13, 14,14a-tetradecahydro-picen-3-yldimethyl-carbamic acid ester (C4);
4-Bromo- (12-bromo-9-hydroxy-6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a , 12b, 13, 14, 14a-tetradecahydro-picen-3-yl) benzoic acid ester (C5);
12-bromo-3,9-dihydroxy-6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene- 2,10-dione (C3);
3,9,10-trihydroxy-6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-dodecahydro-6bH-picene -2-one (C6);
Succinic acid mono- (10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-3,11-dioxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13 , 14, 14a, 14b-tetradecahydro-picen-4-yl) ester;
Succinic acid ethyl ester 10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-3,11-dioxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13, There is 14,14a, 14b-tetradecahydro-picen-4-yl ester.

［式中、
Ｒ_７およびＲ_８は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ’）（Ｒ’’）アミノ基（ここで、Ｒ’およびＲ’’は独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_１５は水素またはハロゲンであり；
Ｒ_１９は水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩIは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１〜３の間である）；またはトリフルオロメチルであり；かつ、
結合

は、二重結合または単結合を意味する］
を有する構造を含んでなる。 In another preferred embodiment, the compound of formula (Ia) used in the present invention is of formula (Ia ″):

[Where:
R ₇ and R ₈ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (here R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or each pair forms a (C═O) group with the carbon to which they are attached. Can do;
R ₁₅ is hydrogen or halogen;
R ₁₉ is hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ Aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl -O- _(C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 to 3); or trifluoromethyl; and,
Join

Means a double bond or a single bond]
The structure which has this.

As a specific example of this structure (Ia ″):
14-bromo-3-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene- 2,10-dione (C7);
4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-tetradeca Hydro-picen-3-yl acetate (C8);
4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-tetradeca Hydro-picen-3-ylnicotinic acid ester (C9);
3,10-dihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-dodecahydro-6bH-picene- 2-one (C10);
3-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 12a, 12b, 13,14,14a-octahydro-6bH, 9H-picene-2,10-dione (C11)
There is.

［式中、
Ｒ_７は水素、ヒドロキシル、ハロゲン、置換もしくは非置換Ｃ_１−Ｃ_１２アルキル、置換もしくは非置換Ｃ_６−Ｃ_１０アリール、またはＮ（Ｒ’）（Ｒ’’）アミノ基（ここで、Ｒ’およびＲ’’は独立に水素またはＣ_１−Ｃ_１２アルキル基である）であり；かつ、
Ｒ_１９は置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１〜３の間である）；またはトリフルオロメチルである］を有する構造を含んでなる。 In another preferred embodiment, the compound of formula (Ia) used in the present invention is of formula (Ia ′ ″):

[Where:
R ₇ is hydrogen, hydroxyl, halogen, substituted or unsubstituted C ₁ -C ₁₂ alkyl, substituted or unsubstituted C ₆ -C ₁₀ aryl, or N (R ′) (R ″) amino group (where R ′ And R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); and
R ₁₉ is substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group (where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; Or N (R ^XIII ) (R ^XIV ) amino, where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl-O -(C ₁ -C ₁₂ ) alkyl-] comprises a structure having _n groups, where n is between 1 and 3; or is trifluoromethyl.

As a specific example of this structure (Ia ''')
10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b- Tetradecahydro-picene-2-carboxylic acid methyl ester;
3,10-dihydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester (C12);
2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-10-propionyloxy-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b -Tetradecahydro-picene-2-carboxylic acid methyl ester (C13);
10-dimethylcarbamoyloxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b-Tetradecahydro-picene-2-carboxylic acid methyl ester (C14)
There is.

［式中、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_７、Ｒ_８、Ｒ_１１およびＲ_１２は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ’）（Ｒ’’）アミノ基（ここで、Ｒ’およびＲ’’は独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_９およびＲ_１０は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ’’’基｛ここで、Ｒ’’’は水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｏ−Ｃ_１−Ｃ_１２アルキル；またはＮ（Ｒ^ＩＶ）（Ｒ^Ｖ）アミノ（ここで、Ｒ^ＩＶおよびＲ^Ｖは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；（ＣＨ_２）_ｎ−ＯＨカルビノール基（ここで、ｎは１〜１０の間の整数である）であるか；あるいは一緒にメチレン基を形成し；
Ｒ_１３、Ｒ_１４、Ｒ_１５、Ｒ_１６、Ｒ_２１、Ｒ_２２およびＲ_２３は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＶＩ）（Ｒ^ＶＩＩ）アミノ基（ここで、Ｒ^ＶＩおよびＲ^ＶＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_１７は水素またはメチルであり；
Ｒ_１８は水素；ヒドロキシル；ハロゲン；Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＩＸ｛ここで、Ｒ^ＩＸは水素；ヒドロキシル；Ｃ_１−Ｃ_１２アルキル；Ｎ（Ｒ^Ｘ）（Ｒ^ＸＩ）アミノ（ここで、Ｒ^ＸおよびＲ^ＸＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；またはＣ_１−Ｃ_１２アルコキシルである｝；またはトリフルオロメチルであり；
Ｒ_１９およびＲ_２０は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；またはトリフルオロメチルであり；
結合

は二重結合または単結合を意味する］
の化合物である。 In another specific embodiment of the invention, the compound of formula (I) for use in the prevention and / or treatment of a disease or condition mediated by ChoK is of formula (Ib):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or is unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or C ₁ -C ₁₂ alkyl group) Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₂₁ , R ₂₂ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl Are N (R ^VI ) (R ^VII ) amino groups, where R ^VI and R ^VII are independently hydrogen or C ₁ -C ₁₂ alkyl groups; or each pair is Can form a (C═O) group with the carbon present;
R ₁₇ is hydrogen or methyl;
R ₁₈ is hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (wherein R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl;
R ₁₉ and R ₂₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂₎ alkyl _-O- (C 1 _{-C 12)} alkyl - _{in] n} group (where, n is between 1 and 3); or trifluoromethyl;
Join

Means a double bond or a single bond]
It is this compound.

［式中、
Ｒ_１９およびＲ_２０は独立に置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；またはトリフルオロメチルである］
を有する構造を含んでなる。 In a preferred embodiment, the compound of formula (Ib) used in the present invention is of formula (Ib ′):

[Where:
R ₁₉ and R ₂₀ are independently substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ —C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂₎ alkyl _-O- (C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 and 3); or trifluoromethyl]
The structure which has this.

  Specific examples of this structure (Ib ′) include 4-nitro- (3-dimethylcarbamoyloxy-5,9-dihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-10-oxo-5, 6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-tetradecahydro-picen-2-yl) benzoic acid ester (C15).

［式中、
Ｒ_１８は水素；ヒドロキシル；ハロゲン；Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＩＸ｛ここで、Ｒ^ＩＸは水素；ヒドロキシル；Ｃ_１−Ｃ_１２アルキル；Ｎ（Ｒ^Ｘ）（Ｒ^ＸＩ）アミノ（ここで、Ｒ^ＸおよびＲ^ＸＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；またはＣ_１−Ｃ_１２アルコキシルである｝；またはトリフルオロメチルであり；
Ｒ_１９は水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；またはトリフルオロメチルであり；
Ｒ_２３は水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＶＩ）（Ｒ^ＶＩＩ）アミノ基（ここで、Ｒ^ＶＩおよびＲ^ＶＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である］
を有する構造を含んでなる。 In another preferred embodiment, the compound of formula (Ib) has the formula (Ib ″):

[Where:
R ₁₈ is hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (wherein R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl;
R ₁₉ is hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ Aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl -O- _(C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 and 3); or trifluoromethyl;
R ₂₃ is hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^VI ) (R ^VII ) amino group (where R ^VI and R ^VII is a is) independently hydrogen or _C 1 _{-C 12} alkyl radical
The structure which has this.

As a specific example of this structure (Ib ″),
7,10,11-trihydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-8-oxo-1,2,3,4,4a, 5,6,6a, 8,12b, 13,14 , 14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester (F16);
9-formyl-10,11-dihydroxy-2,4a, 6a, 12b, 14a-pentamethyl-8-oxo-1,2,3,4,4a, 5,6,6a, 8,12b, 13,14, 14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester (C17);
11-hydroxy-10- (2-methoxy-ethoxymethoxy) -2,4a, 6a, 9,12b, 14a-hexamethyl-8-oxo-1,2,3,4,4a, 5,6,6a, 8 , 12b, 13, 14, 14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester (C18)
There is.

［式中、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_７、Ｒ_８、Ｒ_１１およびＲ_１２は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ’）（Ｒ’’）アミノ基（ここで、Ｒ’およびＲ’’は独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_９およびＲ_１０は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ’’’基｛ここで、Ｒ’’’は水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｏ−Ｃ_１−Ｃ_１２アルキル；またはＮ（Ｒ^ＩＶ）（Ｒ^Ｖ）アミノ（ここで、Ｒ^ＩＶおよびＲ^Ｖは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；（ＣＨ_２）_ｎ−ＯＨカルビノール基（ここで、ｎは１〜１０の間の整数である）であるか；あるいは一緒にメチレン基を形成し；
Ｒ_１３、Ｒ_１４、Ｒ_１５、Ｒ_１６、Ｒ_２１およびＲ_２３は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＶＩ）（Ｒ^ＶＩＩ）アミノ基（ここで、Ｒ^ＶＩおよびＲ^ＶＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_１８は水素；ヒドロキシル；ハロゲン；Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＩＸ｛ここで、Ｒ^ＩＸは水素；ヒドロキシル；Ｃ_１−Ｃ_１２アルキル；Ｎ（Ｒ^Ｘ）（Ｒ^ＸＩ）アミノ（ここで、Ｒ^ＸおよびＲ^ＸＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；またはＣ_１−Ｃ_１２アルコキシルである｝；またはトリフルオロメチルであり；
Ｒ_１９およびＲ_２０は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；またはトリフルオロメチルであり；
結合

は、二重結合または単結合を意味する］
の化合物である。 In another specific embodiment of the invention, the compound of formula (I) for use in the prevention and / or treatment of a disease or condition mediated by ChoK is of formula (Ic):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or is unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or C ₁ -C ₁₂ alkyl group) Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₂₁ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N ( R ^VI ) (R ^VII ) amino group (where R ^VI and R ^VII are independently hydrogen or C ₁ -C ₁₂ alkyl groups); or each pair is bound to the carbon to which they are attached. Together can form a (C═O) group;
R ₁₈ is hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (wherein R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl;
R ₁₉ and R ₂₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂₎ alkyl _-O- (C 1 _{-C 12)} alkyl - _{in] n} group (where, n is between 1 and 3); or trifluoromethyl;
Join

Means a double bond or a single bond]
It is this compound.

［式中、
Ｒ_１９およびＲ_２０は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；またはトリフルオロメチルであり；
結合

は、二重結合または単結合を意味する］
を有する構造を含んでなる。 In one embodiment, the compound of formula (Ic) used in the present invention is of formula (Ic ′):

[Where:
R ₁₉ and R ₂₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂₎ alkyl _-O- (C 1 _{-C 12)} alkyl - _{in] n} group (where, n is between 1 and 3); or trifluoromethyl;
Join

Means a double bond or a single bond]
The structure which has this.

As a specific example of this structure (Ic ′),
10,11-dihydroxy-2,4a, 6a, 9,14a-pentamethyl-1,4,4a, 5,6,6a, 13,14,14a, 14b-decahydro-2H-picen-3-one (C19) ;
10,11-dihydroxy-2,4a, 6a, 9,14a-pentamethyl-4a, 5,6,6a, 13,14,14a, 14b-octahydro-4H-picen-3-one (C20)
There is.

［式中、
Ｒ_１９およびＲ_２０は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；またはトリフルオロメチルである］
を有する構造を含んでなる。 In another preferred embodiment, the compound of formula (Ic) used in the present invention is of formula (Ic ″):

[Where:
R ₁₉ and R ₂₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ —C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); or trifluoromethyl]
The structure which has this.

  Specific examples of this structure (Ic ″) include 10,11-dihydroxy-2,4a, 6a, 9,14a-pentamethyl-1,2,3,4,4a, 5,6,6a, 13, There is 14,14a, 14b-dodecahydro-picene-2-carboxylic acid methyl ester.

［式中、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_７、Ｒ_８、Ｒ_１１およびＲ_１２は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ’）（Ｒ’’）アミノ基（ここで、Ｒ’およびＲ’’は独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_９およびＲ_１０は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ’’’基｛ここで、Ｒ’’’は水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｏ−Ｃ_１−Ｃ_１２アルキル；またはＮ（Ｒ^ＩＶ）（Ｒ^Ｖ）アミノ（ここで、Ｒ^ＩＶおよびＲ^Ｖは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；（ＣＨ_２）_ｎ−ＯＨカルビノール基（ここで、ｎは１〜１０の間の整数である）であるか；あるいは一緒にメチレン基を形成し；
Ｒ_１３、Ｒ_１５、Ｒ_２１およびＲ_２３は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＶＩ）（Ｒ^ＶＩＩ）アミノ基（ここで、Ｒ^ＶＩおよびＲ^ＶＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_１８は水素；ヒドロキシル；ハロゲン；Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＩＸ｛ここで、Ｒ^ＩＸは水素；ヒドロキシル；Ｃ_１−Ｃ_１２アルキル；Ｎ（Ｒ^Ｘ）（Ｒ^ＸＩ）アミノ（ここで、Ｒ^ＸおよびＲ^ＸＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；またはＣ_１−Ｃ_１２アルコキシルである｝；またはトリフルオロメチルであり；
Ｒ_１９、Ｒ_１９’、Ｒ_２０およびＲ_２０’は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；トリフルオロメチルであるか；あるいは各１９−１９’または２０−２０’対は、それらが結合している炭素と一緒にＣ＝Ｏ基を形成することができ；
Ｒ_２４およびＲ_２５は独立に水素、ヒドロキシルまたはハロゲンであり；
結合

は、二重結合または単結合を意味する］
の化合物である。 In another specific embodiment of the invention, the compound of formula (I) for use in the prevention and / or treatment of a disease or condition mediated by ChoK is of formula (Id):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or is unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or C ₁ -C ₁₂ alkyl group) Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
R ₁₃ , R ₁₅ , R ₂₁ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^VI ) (R ^VII ) An amino group (where R ^VI and R ^VII are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or each pair together with the carbon to which they are attached (C═O ) Groups can be formed;
R ₁₈ is hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (wherein R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ and R ₂₅ are independently hydrogen, hydroxyl or halogen;
Join

Means a double bond or a single bond]
It is a compound of this.

［式中、
Ｒ_５およびＲ_６は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ’）（Ｒ’’）アミノ基（ここで、Ｒ’およびＲ’’は独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_１９、Ｒ_１９’、Ｒ_２０およびＲ_２０’は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；トリフルオロメチルであるか；あるいは各１９−１９’または２０−２０’対は、それらが結合している炭素と一緒にＣ＝Ｏ基を形成することができ；
Ｒ_２４およびＲ_２５は独立に水素、ヒドロキシルまたはハロゲンである］
を有する構造を含んでなる。 In a preferred embodiment, the compound of formula (Id) used in the present invention is of formula (Id ′):

[Where:
R ₅ and R ₆ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (here R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or each pair forms a (C═O) group with the carbon to which they are attached. Can do;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ and R ₂₅ are independently hydrogen, hydroxyl or halogen]
The structure which has this.

As a specific example of this structure (Id ′):
1-bromo-9-hydroxy-4,6b, 8a, 11,12b, 14b-hexamethyl-6b, 7,8,8a, 9,11,12,12a, 12b, 14b-decahydro-1H-picene-2, 3,10-trione (C22);
1-bromo-4,6b, 8a, 11,12b, 14b-hexamethyl-6b, 7,8,8a, 9,11,12,12a, 12b, 14b-decahydro-1H-picene-2,3,10- Trion (C23)
There is.

［式中、
Ｒ_１９、Ｒ_１９’、Ｒ_２０およびＲ_２０’は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；トリフルオロメチルであるか；あるいは各１９−１９’または２０−２０’対は、それらが結合している炭素と一緒にＣ＝Ｏ基を形成することができ；
Ｒ_２４およびＲ_２５は独立に水素、ヒドロキシルまたはハロゲンである］
を有する構造を含んでなる。 In another preferred embodiment, the compound of formula (Id) used in the present invention is of formula (Id ″):

[Where:
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ and R ₂₅ are independently hydrogen, hydroxyl or halogen]
The structure which has this.

  Specific examples of this structure (Id ″) include 12-bromo-2,4a, 6a, 9,12a, 14a-hexamethyl-10,11-dioxo-1,2,3,4,4a, 5 6,6a, 10,11,12,12a, 14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester (C24).

［式中、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_７、Ｒ_８、Ｒ_１１およびＲ_１２は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ’）（Ｒ’’）アミノ基（ここで、Ｒ’およびＲ’’は独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_９およびＲ_１０は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ’’’基｛ここで、Ｒ’’’は水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｏ−Ｃ_１−Ｃ_１２アルキル；またはＮ（Ｒ^ＩＶ）（Ｒ^Ｖ）アミノ（ここで、Ｒ^ＩＶおよびＲ^Ｖは独立に水素またはアルキル基Ｃ_１−Ｃ_１２である）である｝；カルビノール基（ＣＨ_２）_ｎ−ＯＨ（ここで、ｎは１〜１０の間の整数である）であるか；あるいは一緒にメチレン基を形成し；
Ｒ_１３、Ｒ_１４、Ｒ_１５、Ｒ_１６、Ｒ_２１およびＲ_２３は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＶＩ）（Ｒ^ＶＩＩ）アミノ基（ここで、Ｒ^ＶＩおよびＲ^ＶＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_１８およびＲ_１８’は独立に水素；ヒドロキシル；ハロゲン；Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＩＸ｛ここで、Ｒ^ＩＸは水素；ヒドロキシル；Ｃ_１−Ｃ_１２アルキル；Ｎ（Ｒ^Ｘ）（Ｒ^ＸＩ）アミノ（ここで、Ｒ^ＸおよびＲ^ＸＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；またはＣ_１−Ｃ_１２アルコキシルである｝；またはトリフルオロメチルであり；
Ｒ_１９、Ｒ_１９’、Ｒ_２０およびＲ_２０’は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；トリフルオロメチルであるか；あるいは各１９−１９’または２０−２０’対は、それらが結合している炭素と一緒にＣ＝Ｏ基を形成することができ；
Ｒ_２４は水素、ヒドロキシルまたはハロゲンであり；
結合

は、二重結合または単結合を意味する］
の化合物である。 In another specific embodiment of the invention, the compound of formula (I) for use in the prevention and / or treatment of a disease or condition mediated by ChoK is of formula (Ie):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or is unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or C ₁ -C ₁₂ alkyl group) Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently Is a hydrogen or alkyl group C ₁ -C ₁₂ )}; a carbinol group (CH ₂ ) _n —OH (where n is an integer between 1 and 10); or together with methylene Forming a group;
R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₂₁ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N ( R ^VI ) (R ^VII ) amino groups, where R ^VI and R ^VII are independently hydrogen or C ₁ -C ₁₂ alkyl groups; or each pair is attached to the carbon to which they are attached. Together can form a (C═O) group;
R ₁₈ and R _{18 ′} are independently hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (where R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl Yes;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ is hydrogen, hydroxyl or halogen;
Join

Means a double bond or a single bond]
It is a compound of this.

［式中、
Ｒ_１８およびＲ_１８’は独立に水素；ヒドロキシル；ハロゲン；Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＩＸ｛ここで、Ｒ^ＩＸは水素；ヒドロキシル；Ｃ_１−Ｃ_１２アルキル；Ｎ（Ｒ^Ｘ）（Ｒ^ＸＩ）アミノ（ここで、Ｒ^ＸおよびＲ^ＸＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；またはＣ_１−Ｃ_１２アルコキシルである｝；またはトリフルオロメチルであり；
Ｒ_１９、Ｒ_１９’、Ｒ_２０およびＲ_２０’は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；トリフルオロメチルであるか；あるいは各１９−１９’または２０−２０’対は、それらが結合している炭素と一緒にＣ＝Ｏ基を形成することができ；
Ｒ_２４は水素、ヒドロキシルまたはハロゲンである］
を有する構造を含んでなる。 In a preferred embodiment, the compound of formula (Ie) used in the present invention is of formula (Ie ′):

[Where:
R ₁₈ and R _{18 ′} are independently hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (where R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl Yes;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ is hydrogen, hydroxyl or halogen]
The structure which has this.

  Specific examples of this structure (Ie ′) include 9-hydroxy-2,4a, 6a, 9,12b-hexamethyl-10,11-dioxo-1,2,3,4,4a, 5,6,6a. 9, 10, 11, 12b, 13, 14, 14a, 14b-hexadecahydro-picene-2-carboxylic acid methyl ester (C25).

［式中、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_７、Ｒ_８、Ｒ_１１およびＲ_１２は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ’）（Ｒ’’）アミノ基（ここで、Ｒ’およびＲ’’は独立に水素またはＣ_１−Ｃ_１２アルキル基である）；であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_９およびＲ_１０は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ’’’基｛ここで、Ｒ’’’は水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｏ−Ｃ_１−Ｃ_１２アルキル；またはＮ（Ｒ^ＩＶ）（Ｒ^Ｖ）アミノ（ここで、Ｒ^ＩＶおよびＲ^Ｖは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；（ＣＨ_２）_ｎ−ＯＨカルビノール基（ここで、ｎは１〜１０の間の整数である）であるか；あるいは一緒にメチレン基を形成し；
Ｒ_１３、Ｒ_１４、Ｒ_１５、Ｒ_２１およびＲ_２３は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＶＩ）（Ｒ^ＶＩＩ）アミノ基（ここで、Ｒ^ＶＩおよびＲ^ＶＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_１８およびＲ_１８’は独立に水素；ヒドロキシル；ハロゲン；Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＩＸ｛ここで、Ｒ^ＩＸは水素；ヒドロキシル；Ｃ_１−Ｃ_１２アルキル；Ｎ（Ｒ^Ｘ）（Ｒ^ＸＩ）アミノ（ここで、Ｒ^ＸおよびＲ^ＸＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；またはＣ_１−Ｃ_１２アルコキシルである｝；またはトリフルオロメチルであり；
Ｒ_１９、Ｒ_１９’、Ｒ_２０およびＲ_２０’は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基（ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリールである）；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；トリフルオロメチルであるか；あるいは各１９−１９’または２０−２０’対は、それらが結合している炭素と一緒にＣ＝Ｏ基を形成することができ；
Ｒ_２４は独立に水素、ヒドロキシルまたはハロゲンであり；
結合

は、二重結合または単結合を意味する］
の化合物である。 In another specific embodiment of the invention, the compound of formula (I) for use in the prevention and / or treatment of a disease or condition mediated by ChoK is of formula (If):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or an unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group, where R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group; Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
R ₁₃ , R ₁₄ , R ₁₅ , R ₂₁ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^VI ) (R ^VII ) an amino group, where R ^VI and R ^VII are independently hydrogen or a C ₁ -C ₁₂ alkyl group; or each pair together with the carbon to which they are attached ( C = O) groups can be formed;
R ₁₈ and R _{18 ′} are independently hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (where R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl Yes;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group (where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C _1- C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl); or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ is independently hydrogen, hydroxyl or halogen;
Join

Means a double bond or a single bond]
It is this compound.

［式中、
Ｒ_１８およびＲ_１８’は独立に水素；ヒドロキシル；ハロゲン；Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＩＸ｛ここで、Ｒ^ＩＸは水素；ヒドロキシル；Ｃ_１−Ｃ_１２アルキル；Ｎ（Ｒ^Ｘ）（Ｒ^ＸＩ）アミノ（ここで、Ｒ^ＸおよびＲ^ＸＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；またはＣ_１−Ｃ_１２アルコキシルである｝；またはトリフルオロメチルであり；
Ｒ_１９、Ｒ_１９’、Ｒ_２０およびＲ_２０’は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基（ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリールである）；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；トリフルオロメチルであるか；あるいは各１９−１９’または２０−２０’対は、それらが結合している炭素と一緒にＣ＝Ｏ基を形成することができ；
Ｒ_２４は独立に水素、ヒドロキシルまたはハロゲンである］
を有する構造を含んでなる。 In a preferred embodiment, the compound of formula (If) used in the present invention is of formula (If ′):

[Where:
R ₁₈ and R _{18 ′} are independently hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (where R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl Yes;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group (where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C _1- C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl); or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ is independently hydrogen, hydroxyl or halogen.
The structure which has this.

  Specific examples of this structure (If ′) include 9-hydroxy-2,4a, 6a, 6b, 9-hexamethyl-10,11-dioxo-1,2,3,4,4a, 5,6,6a. , 6b, 8a, 9, 10, 11, 14, 14a, 14b-hexadecahydro-picene-2-carboxylic acid methyl ester (C26).

［式中、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_９、Ｒ_１０、Ｒ_１１、Ｒ_１２、Ｒ_１３、Ｒ_１４、Ｒ_１５、Ｒ_１６、Ｒ_１７、Ｒ_１８、Ｒ_１９およびＲ_２０は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＸＶ）（Ｒ^ＸＶＩ）アミノ基（ここで、Ｒ^ＸＶおよびＲ^ＸＶＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_７およびＲ_８は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＸＶＩＩ基｛ここで、Ｒ^ＸＶＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｏ−Ｃ_１−Ｃ_１２アルキル；またはＮ（Ｒ^{ＸＶＩＩＩ}）（Ｒ^ＸＩＸ）アミノ（ここで、Ｒ^{ＸＶＩＩＩ}およびＲ^ＸＩＸは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；（ＣＨ_２）_ｎ−ＯＨカルビノール基（ここで、ｎは１〜１０の間の整数である）であるか；あるいは一緒にメチレン基を形成し；
Ｒ_２１およびＲ_２４は独立に置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＸ基（ここで、Ｒ^ＸＸは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＸＩ）（Ｒ^ＸＸＩＩ）アミノ（ここで、Ｒ^ＸＸＩおよびＲ^ＸＸＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；またはトリフルオロメチルであり；
Ｒ_２２およびＲ_２３は、
Ｒ_２４がＲ_２０に対してパラ位にある場合には、水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^{ＸＸＩＩＩ}基｛ここで、Ｒ^{ＸＸＩＩＩ}は水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＸＩＶ）（Ｒ^ＸＸＶ）アミノ（ここで、Ｒ^ＸＸＩＶおよびＲ^ＸＸＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１〜３の間である）；またはトリフルオロメチルであるか；あるいは
Ｒ_２４がＲ_２０に対してメタ位にある場合には、それぞれＯＲ_２２’およびＯＲ_２３’であり、ここで、Ｒ_２２’およびＲ_２３’は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＸＶＩ基｛ここで、Ｒ^ＸＸＶＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^{ＸＸＶＩＩ}）（Ｒ^{ＸＸＶＩＩＩ}）アミノ（ここで、Ｒ^{ＸＸＶＩＩ}およびＲ^{ＸＸＶＩＩＩ}は独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；またはトリフルオロメチルである］
の化合物である。 In another specific embodiment of the invention, the compound of formula (II) used for the prevention and / or treatment of a disease or condition mediated by ChoK is of formula (IIa):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₉ , R ₁₀ , R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₁₇ , R ₁₈ , R ₁₉ And R ₂₀ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^XV ) (R ^XVI ) amino group (where R ^XV and R ^XVI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or each pair can form a (C═O) group with the carbon to which they are attached. ;
R ₇ and R ₈ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^XVII group {where R ^XVII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted _C 6 _{-C 10 aryl; O-C} 1 _{-C 12} alkyl; with or ^{N (R XVIII) (R XIX} ) amino ^{(wherein, R XVIII} and ^{R XIX} are independently hydrogen or _{C 1} Is a —C ₁₂ alkyl group)}; (CH ₂ ) _n —OH carbinol group (where n is an integer between 1 and 10); or together forms a methylene group. ;
R ₂₁ and R ₂₄ are independently substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XX group (where R ^XX is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ —C ₁₀ aryl; or N (R ^XXI ) (R ^XXII ) amino, where R ^XXI and R ^XXII are independently hydrogen or a C ₁ -C ₁₂ alkyl group; and [(C ₁ -C ₁₂ ) alkyl. -O- _(C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 and 3); or trifluoromethyl;
R ₂₂ and R ₂₃ are
When R ₂₄ is para to R ₂₀ , hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XXIII group {where R ^XXIII is hydrogen; hydroxyl; substituted or unsubstituted C _1- C ₁₂ alkyl; substituted or unsubstituted _C 6 _{-C 10} aryl; or ^N (R ^{XXIV) (R XXV)} amino ^{(wherein, R XXIV} and ^{R XXV} are independently hydrogen or _C 1 _{-C 12} alkyl group) Or [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); or is trifluoromethyl? Or, when R ₂₄ is in the meta position relative to R ₂₀ , OR ₂₂ ′ and OR ₂₃ ′, respectively, where R ₂₂ ′ and R ₂₃ ′ are independently hydrogen; Here ^{COR XXVI} group ^{{, R XXVI} is ^hydrogen; unsubstituted _C 1 _{-C 12} alkyl hydroxyl; substituted or unsubstituted _C 1 _{-C 12} alkyl; substituted or unsubstituted _C 6 _{-C 10} aryl; or N (R ^XXVII ) (R ^XXVIII ) amino where R ^XXVII and R ^XXVIII are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl-O- (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); or trifluoromethyl]
It is this compound.

［式中、
Ｒ_１９およびＲ_２０は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＸＶ）（Ｒ^ＸＶＩ）アミノ基（ここで、Ｒ^ＸＶおよびＲ^ＸＶＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）カルボキシル基を形成することができ；
Ｒ_２１およびＲ_２４は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＸＸＩ）（Ｒ^ＸＸＩＩ）アミノ基（ここで、Ｒ^ＸＸＩおよびＲ^ＸＸＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか、あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）カルボキシル基を形成することができ；
Ｒ_２２およびＲ_２３は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＸＸＩＶ）（Ｒ^ＸＸＶ）アミノ基（ここで、Ｒ^ＸＸＩＶおよびＲ^ＸＸＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか、あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）カルボキシル基を形成することができる］
を有する構造を含んでなる。 In a preferred embodiment, the compound of formula (IIa) used in the present invention is of formula (IIa ′):

[Where:
R ₁₉ and R ₂₀ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^XV ) (R ^XVI ) amino group (where , R ^XV and R ^XVI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or each pair forms a (C═O) carboxyl group with the carbon to which they are attached. It is possible;
R ₂₁ and R ₂₄ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^XXI ) (R ^XXII ) amino group (where , R ^XXI and R ^XXII are independently hydrogen or a C ₁ -C ₁₂ alkyl group) or each pair together with the carbon to which they are attached (C═O) forms a carboxyl group It is possible;
R ₂₂ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^XXIV ) (R ^XXV ) amino group (where , R ^XXIV and R ^XXV are independently hydrogen or a C ₁ -C ₁₂ alkyl group), or each pair forms a (C═O) carboxyl group with the carbon to which they are attached. be able to]
The structure which has this.

  A specific example of this structure (IIa ′) is 8- [2- (6,7-dihydroxy-1,5-dimethyl-naphthalen-2-yl) -ethyl] -2,4a-tetramethyl-1, There is 2,3,4,4a, 5,6,7-octahydro-naphthalene-2-carboxylic acid methyl ester (C27).

  The compounds according to the invention act as blockers of phosphorylcholine biosynthesis by selective blockade of the choline kinase (ChoK) enzyme and do not affect normal cells at the same intensity and are therefore sufficient for greater efficacy in tumor therapy. In particular, it showed a selective effect on signal transduction pathways required for malignant transformation by specific oncogenes.

  Thus, in a particular embodiment, the ChoK mediated disease or condition to be prevented or treated is a cancer, preferably a cancer selected from breast cancer, lung cancer, colorectal cancer and pancreatic cancer.

  On the other hand, several parasites such as Plasmodium falciparum or Trypanosoma cruci, several viruses such as adenovirus, bacteria such as Streptococcus pneumoniae, and Candida albicans Since the Candida slbicans fungus requires a metabolic phosphatidylcholine synthesis pathway via choline kinase to complete its infection cycle in humans and animals, the bioassays performed are viral, parasite, bacterial and fungal symptoms The use of the compounds described in this invention can be extended to the treatment of In this sense, the technical background is the role of the ChoK enzyme in the intracellular metabolism of certain nucleosides in Hep-G2 cells, the use of the enzyme as an enzyme marker in parasitic diseases, and in viruses, bacteria and fungi. Supports its involvement in the biosynthesis of important phospholipids.

  As a result, in another embodiment, the ChoK-mediated disease or condition to be prevented and / or treated is that caused by a viral disease, preferably an adenovirus.

  In another embodiment, the ChoK mediated disease or condition to be prevented and / or treated is one caused by a parasitic disease, preferably Plasmodium or Trypanosoma.

  In another embodiment, the ChoK mediated disease or condition to be prevented and / or treated is one caused by a bacterial disease, preferably Streptococcus.

  In another embodiment, the ChoK-mediated disease or condition to be prevented and / or treated is one caused by a fungal disease, preferably Candida.

［式中、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_７、Ｒ_８、Ｒ_１１およびＲ_１２は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ’）（Ｒ’’）アミノ基（ここで、Ｒ’およびＲ’’は独立に水素またはＣ_１−Ｃ_１２アルキル基である）；ＯＣＯＲ基（ここで、Ｒは（ＣＨ_２）_２ＣＯＯＨまたは（ＣＨ_２）_２ＣＯ_２ＣＨ_２ＣＨ_３である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_９およびＲ_１０は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ’’’基｛ここで、Ｒ’’’は水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｏ−Ｃ_１−Ｃ_１２アルキル；またはＮ（Ｒ^ＩＶ）（Ｒ^Ｖ）アミノ（ここで、Ｒ^ＩＶおよびＲ^Ｖは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；（ＣＨ_２）_ｎ−ＯＨカルビノール基（ここで、ｎは１〜１０の間の整数である）であるか；あるいは一緒にメチレン基を形成し；
結合

は二重結合または単結合を意味し；
三環式構造

は、下記の構造：

から選択され、ここで、
Ｒ_１３、Ｒ_１４、Ｒ_１５、Ｒ_１６、Ｒ_２１、Ｒ_２２およびＲ_２３は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＶＩ）（Ｒ^ＶＩＩ）アミノ基（ここで、Ｒ^ＶＩおよびＲ^ＶＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；ＯＣＯＲ^ＶＩＩＩ基（ここで、Ｒ^ＶＩＩＩは（ＣＨ_２）_２ＣＯＯＨまたは（ＣＨ_２）_２ＣＯ_２ＣＨ_２ＣＨ_３である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができるか、または各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_１７は水素またはメチルであり；
Ｒ_１８およびＲ_１８’は独立に水素；ヒドロキシル；ハロゲン；Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＩＸ｛ここで、Ｒ^ＩＸは水素；ヒドロキシル；Ｃ_１−Ｃ_１２アルキル；Ｎ（Ｒ^Ｘ）（Ｒ^ＸＩ）アミノ（ここで、Ｒ^ＸおよびＲ^ＸＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；またはＣ_１−Ｃ_１２アルコキシルである｝；またはトリフルオロメチルであり；
Ｒ_１９、Ｒ_１９’、Ｒ_２０およびＲ_２０’は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；トリフルオロメチルであるか；あるいは各１９−１９’または２０−２０’対は、それらが結合している炭素と一緒にＣ＝Ｏ基を形成することができ；
Ｒ_２４およびＲ_２５は独立に水素、ヒドロキシルまたはハロゲンである］
の化合物、またはその薬学上許容される塩、誘導体、プロドラッグ、溶媒和物もしくは立体異性体
［ただし、
三環式構造が（ａ）である場合、式（Ｉ）の化合物は、
１０−ヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−１１−オキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−２−カルボン酸；
１０−ヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−１１−オキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−２−カルボン酸メチルエステル；
３，１０−ジヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−１１−オキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−２−カルボン酸メチルエステル；
３−ヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−７，８，８ａ，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−デカヒドロ−６ｂＨ，９Ｈ−ピセン−２，１０−ジオン；
３，９−ジヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−７，８，８ａ，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−デカヒドロ−６ｂＨ，９Ｈ−ピセン−２，１０−ジオン；
３，７，９−トリヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−７，８，８ａ，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−デカヒドロ−６ｂＨ，９Ｈ−ピセン−２，１０−ジオン；
１４−ブロモ−３，７，９−トリヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−７，８，８ａ，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−デカヒドロ−６ｂＨ，９Ｈ−ピセン−２，１０−ジオン；
コハク酸モノ−（１０−ヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−３，１１−ジオキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−４−イル）エステル；
コハク酸エチルエステル１０−ヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−３，１１−ジオキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−４−イルエステル；
酢酸９−ヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−２，１０−ジオキソ−２，６ｂ，７，８，８ａ，９，１０，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−テトラデカヒドロ−ピセン−３−イルエステル；
ドデカン酸９−ヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−２，１０−ジオキソ−２，６ｂ，７，８，８ａ，９，１０，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−テトラデカヒドロ−ピセン−３−イルエステル；
ジメチル−カルバミン酸９−ヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−２，１０−ジオキソ−２，６ｂ，７，８，８ａ，９，１０，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−テトラデカヒドロ−ピセン−３−イルエステル；
ニコチン酸９−ヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−２，１０−ジオキソ−２，６ｂ，７，８，８ａ，９，１０，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−テトラデカヒドロ−ピセン−３−イルエステル；
３，１０−ジヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−１１−オキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−２−カルボン酸メチルエステル；
１０−ヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−１１−オキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−２−カルボン酸メチルエステル
でなく、
三環式構造が（ｂ）であり、Ｒ_１９およびＲ_２０が独立に水素またはアシル基である場合、
Ｒ_５はヒドロキシルであるか；または
Ｒ_２１およびＲ_２２はそれらが結合している炭素と一緒にＣ＝Ｏ基を形成し、Ｒ_１０はＣＯＯＨでなく、
三環式構造が（ｃ）であり、Ｒ_１９およびＲ_２０が双方ともＣＨ_３である場合、Ｒ_１５およびＲ_１６はそれらが結合している炭素と一緒にＣ＝Ｏ基を形成しない］
に関する。 Another object of the present invention is the general formula (I):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or an unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); Where R is (CH ₂ ) ₂ COOH or (CH ₂ ) ₂ CO ₂ CH ₂ CH ₃ ; or each pair together with the carbon to which they are attached (C═O ) Groups can be formed;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
Join

Means a double bond or a single bond;
Tricyclic structure

Has the following structure:

Where
R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₂₁ , R ₂₂ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl N (R ^VI ) (R ^VII ) amino group (where R ^VI and R ^VII are independently hydrogen or a C ₁ -C ₁₂ alkyl group); OCOR ^VIII group (where R ^VIII is (CH ₂ ) ₂ COOH or (CH ₂ ) ₂ CO ₂ CH ₂ CH ₃ ); or is each pair capable of forming a (C═O) group with the carbon to which they are attached? Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₁₇ is hydrogen or methyl;
R ₁₈ and R _{18 ′} are independently hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (where R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl Yes;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ and R ₂₅ are independently hydrogen, hydroxyl or halogen]
Or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof [wherein
When the tricyclic structure is (a), the compound of formula (I) is
10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b- Tetradecahydro-picene-2-carboxylic acid;
10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b- Tetradecahydro-picene-2-carboxylic acid methyl ester;
3,10-dihydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester;
3-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene-2,10- Dione;
3,9-dihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene-2, 10-dione;
3,7,9-trihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene -2,10-dione;
14-bromo-3,7,9-trihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH , 9H-picene-2,10-dione;
Succinic acid mono- (10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-3,11-dioxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13 , 14, 14a, 14b-tetradecahydro-picen-4-yl) ester;
Succinic acid ethyl ester 10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-3,11-dioxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13, 14,14a, 14b-tetradecahydro-picen-4-yl ester;
Acetic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14 , 14a-tetradecahydro-picen-3-yl ester;
Dodecanoic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13, 14,14a-tetradecahydro-picen-3-yl ester;
Dimethyl-carbamic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-tetradecahydro-picen-3-yl ester;
Nicotinic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13, 14,14a-tetradecahydro-picen-3-yl ester;
3,10-dihydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester;
10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b- Not tetradecahydro-picene-2-carboxylic acid methyl ester,
When the tricyclic structure is (b) and R ₁₉ and R ₂₀ are independently hydrogen or an acyl group,
R ₅ is hydroxyl; or R ₂₁ and R ₂₂ together with the carbon to which they are attached form a C═O group, R ₁₀ is not COOH,
When the tricyclic structure is (c) and R ₁₉ and R ₂₀ are both CH ₃ , R ₁₅ and R ₁₆ do not form a C═O group with the carbon to which they are attached]
About.

［式中、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_７、Ｒ_８、Ｒ_１１およびＲ_１２は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ’）（Ｒ’’）アミノ基（ここで、Ｒ’およびＲ’’は独立に水素またはＣ_１−Ｃ_１２アルキル基である）；ＯＣＯＲ基（ここで、Ｒは（ＣＨ_２）_２ＣＯＯＨまたは（ＣＨ_２）_２ＣＯ_２ＣＨ_２ＣＨ_３である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_９およびＲ_１０は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ’’’基｛ここで、Ｒ’’’は水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｏ−Ｃ_１−Ｃ_１２アルキル；またはＮ（Ｒ^ＩＶ）（Ｒ^Ｖ）アミノ（ここで、Ｒ^ＩＶおよびＲ^Ｖは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；（ＣＨ_２）_ｎ−ＯＨカルビノール基（ここで、ｎは１〜１０の間の整数である）であるか；あるいは一緒にメチレン基を形成し；
Ｒ_１３、Ｒ_１４、Ｒ_１５およびＲ_１６は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＶＩ）（Ｒ^ＶＩＩ）アミノ基（ここで、Ｒ^ＶＩおよびＲ^ＶＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；ＯＣＯＲ^ＶＩＩＩ基（ここで、Ｒ^ＶＩＩＩは（ＣＨ_２）_２ＣＯＯＨまたは（ＣＨ_２）_２ＣＯ_２ＣＨ_２ＣＨ_３である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_１７は水素またはメチルであり；
Ｒ_１８は水素；ヒドロキシル；ハロゲン；Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＩＸ｛ここで、Ｒ^ＩＸは水素；ヒドロキシル；Ｃ_１−Ｃ_１２アルキル；Ｎ（Ｒ^Ｘ）（Ｒ^ＸＩ）アミノ（ここで、Ｒ^ＸおよびＲ^ＸＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；またはＣ_１−Ｃ_１２アルコキシルである｝；またはトリフルオロメチルであり；
Ｒ_１９は水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；またはトリフルオロメチルであり；
結合

は二重結合または単結合を意味する］
の化合物
［ただし、式（Ｉａ）の化合物は、
１０−ヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−１１−オキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−２−カルボン酸；
１０−ヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−１１−オキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−２−カルボン酸メチルエステル；
３，１０−ジヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−１１−オキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−２−カルボン酸メチルエステル；
３−ヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−７，８，８ａ，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−デカヒドロ−６ｂＨ，９Ｈ−ピセン−２，１０−ジオン；
３，９−ジヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−７，８，８ａ，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−デカヒドロ−６ｂＨ，９Ｈ−ピセン−２，１０−ジオン；
３，７，９−トリヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−７，８，８ａ，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−デカヒドロ−６ｂＨ，９Ｈ−ピセン−２，１０−ジオン；
１４−ブロモ−３，７，９−トリヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−７，８，８ａ，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−デカヒドロ−６ｂＨ，９Ｈ−ピセン−２，１０−ジオン；
コハク酸モノ−（１０−ヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−３，１１−ジオキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−４−イル）エステル；
コハク酸エチルエステル１０−ヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−３，１１−ジオキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−４−イルエステル；
酢酸９−ヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−２，１０−ジオキソ−２，６ｂ，７，８，８ａ，９，１０，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−テトラデカヒドロ−ピセン−３−イルエステル；
ドデカン酸９−ヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−２，１０−ジオキソ−２，６ｂ，７，８，８ａ，９，１０，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−テトラデカヒドロ−ピセン−３−イルエステル；
ジメチル−カルバミン酸９−ヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−２，１０−ジオキソ−２，６ｂ，７，８，８ａ，９，１０，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−テトラデカヒドロ−ピセン−３−イルエステル；
ニコチン酸９−ヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−２，１０−ジオキソ−２，６ｂ，７，８，８ａ，９，１０，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−テトラデカヒドロ−ピセン−３−イルエステル
でない］
を対象とする。 In one particular embodiment, the invention provides a compound of formula (Ia):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or an unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); Where R is (CH ₂ ) ₂ COOH or (CH ₂ ) ₂ CO ₂ CH ₂ CH ₃ ; or each pair together with the carbon to which they are attached (C═O ) Groups can be formed;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
R ₁₃ , R ₁₄ , R ₁₅ and R ₁₆ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^VI ) (R ^VII ) Amino group (where R ^VI and R ^VII are independently hydrogen or C ₁ -C ₁₂ alkyl group); OCOR ^VIII group (where R ^VIII is (CH ₂ ) ₂ COOH or (CH ₂ ) ₂ Each pair can form a (C═O) group with the carbon to which they are attached; or CO ₂ CH ₂ CH ₃ ;
R ₁₇ is hydrogen or methyl;
R ₁₈ is hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (wherein R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl;
R ₁₉ is hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ Aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl -O- _(C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 and 3); or trifluoromethyl;
Join

Means a double bond or a single bond]
Wherein the compound of formula (Ia) is
10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b- Tetradecahydro-picene-2-carboxylic acid;
10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b- Tetradecahydro-picene-2-carboxylic acid methyl ester;
3,10-dihydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester;
3-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene-2,10- Dione;
3,9-dihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene-2, 10-dione;
3,7,9-trihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene -2,10-dione;
14-bromo-3,7,9-trihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH , 9H-picene-2,10-dione;
Succinic acid mono- (10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-3,11-dioxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13 , 14, 14a, 14b-tetradecahydro-picen-4-yl) ester;
Succinic acid ethyl ester 10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-3,11-dioxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13, 14,14a, 14b-tetradecahydro-picen-4-yl ester;
Acetic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14 , 14a-tetradecahydro-picen-3-yl ester;
Dodecanoic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13, 14,14a-tetradecahydro-picen-3-yl ester;
Dimethyl-carbamic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-tetradecahydro-picen-3-yl ester;
Nicotinic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13, Not 14,14a-tetradecahydro-picen-3-yl ester]
Is targeted.

［式中、
Ｒ_５はヒドロキシルまたはＯＣＯＲ基であり、ここでＲは（ＣＨ_２）_２ＣＯＯＨまたは（ＣＨ_２）_２ＣＯ_２ＣＨ_２ＣＨ_３であり；
Ｒ_７およびＲ_８は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ’）（Ｒ’’）アミノ基（ここで、Ｒ’およびＲ’’は独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_１２は独立に水素またはハロゲンであり；かつ、
Ｒ_１９は水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩIは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１〜３の間である）；またはトリフルオロメチルであり；かつ、
結合

は、二重結合または単結合を意味する］
を有する構造を含んでなり、
ただし、式（Ｉａ’）の化合物は、
１０−ヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−１１−オキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−２−カルボン酸；
１０−ヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−１１−オキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−２−カルボン酸メチルエステル；
３，１０−ジヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−１１−オキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−２−カルボン酸メチルエステル；
３−ヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−７，８，８ａ，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−デカヒドロ−６ｂＨ，９Ｈ−ピセン−２，１０−ジオン；
３，９−ジヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−７，８，８ａ，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−デカヒドロ−６ｂＨ，９Ｈ−ピセン−２，１０−ジオン；
３，７，９−トリヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−７，８，８ａ，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−デカヒドロ−６ｂＨ，９Ｈ−ピセン−２，１０−ジオン；
１４−ブロモ−３，７，９−トリヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−７，８，８ａ，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−デカヒドロ−６ｂＨ，９Ｈ−ピセン−２，１０−ジオン；
コハク酸モノ−（１０−ヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−３，１１−ジオキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−４−イル）エステル；
コハク酸エチルエステル１０−ヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−３，１１−ジオキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−４−イルエステル；
酢酸９−ヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−２，１０−ジオキソ−２，６ｂ，７，８，８ａ，９，１０，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−テトラデカヒドロ−ピセン−３−イルエステル；
ドデカン酸９−ヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−２，１０−ジオキソ−２，６ｂ，７，８，８ａ，９，１０，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−テトラデカヒドロ−ピセン−３−イルエステル；
ジメチル−カルバミン酸９−ヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−２，１０−ジオキソ−２，６ｂ，７，８，８ａ，９，１０，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−テトラデカヒドロ−ピセン−３−イルエステル；
ニコチン酸９−ヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−２，１０−ジオキソ−２，６ｂ，７，８，８ａ，９，１０，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−テトラデカヒドロ−ピセン−３−イルエステル；
３，１０−ジヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−１１−オキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−２−カルボン酸メチルエステル；
１０−ヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−１１−オキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−２−カルボン酸メチルエステル
でない。 In a preferred embodiment, the compound of formula (Ia) is of formula (Ia ′)

[Where:
R ₅ is a hydroxyl or OCOR group, where R is (CH ₂ ) ₂ COOH or (CH ₂ ) ₂ CO ₂ CH ₂ CH ₃ ;
R ₇ and R ₈ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (here R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or each pair forms a (C═O) group with the carbon to which they are attached. Can do;
R ₁₂ is independently hydrogen or halogen; and
R ₁₉ is hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ Aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl -O- _(C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 to 3); or trifluoromethyl; and,
Join

Means a double bond or a single bond]
Comprising a structure having
Provided that the compound of formula (Ia ′) is
10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b- Tetradecahydro-picene-2-carboxylic acid;
10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b- Tetradecahydro-picene-2-carboxylic acid methyl ester;
3,10-dihydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester;
3-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene-2,10- Dione;
3,9-dihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene-2, 10-dione;
3,7,9-trihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene -2,10-dione;
14-bromo-3,7,9-trihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH , 9H-picene-2,10-dione;
Succinic acid mono- (10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-3,11-dioxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13 , 14, 14a, 14b-tetradecahydro-picen-4-yl) ester;
Succinic acid ethyl ester 10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-3,11-dioxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13, 14,14a, 14b-tetradecahydro-picen-4-yl ester;
Acetic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14 , 14a-tetradecahydro-picen-3-yl ester;
Dodecanoic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13, 14,14a-tetradecahydro-picen-3-yl ester;
Dimethyl-carbamic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-tetradecahydro-picen-3-yl ester;
Nicotinic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13, 14,14a-tetradecahydro-picen-3-yl ester;
3,10-dihydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester;
10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b- Not tetradecahydro-picene-2-carboxylic acid methyl ester.

As a specific example of this structure (Ia ′),
9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14, 14a-tetradecahydro-picen-3-ylpropionic acid ester (C1);
4-Bromo- (9-hydroxy-6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13 , 14,14a-tetradecahydro-picen-3-yl) benzoic acid ester (C2);
12-bromo-3,9-dihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H- Picene-2,10-dione (C3);
12-bromo-9-hydroxy-6b, 8a, 11, 12b, 14a-hexamethyl-2, 10-dioxo-2, 6b, 7, 8, 8a, 9, 10, 11, 12, 12a, 12b, 13, 14,14a-tetradecahydro-picen-3-yldimethyl-carbamic acid ester (C4);
4-Bromo- (12-bromo-9-hydroxy-6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a , 12b, 13, 14, 14a-tetradecahydro-picen-3-yl) benzoic acid ester (C5);
3,9,10-trihydroxy-6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-dodecahydro-6bH-picene -2-one (C6)
There is.

［式中、
Ｒ_７およびＲ_８は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ’）（Ｒ’’）アミノ基（ここで、Ｒ’およびＲ’’は独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_１５は水素またはハロゲンであり；
Ｒ_１９は水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩIは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１〜３の間である）；またはトリフルオロメチルであり；かつ、
結合

は、二重結合または単結合を意味する］
を有する構造を含んでなり、
ただし、式（Ｉａ’’）の化合物は、
３−ヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−７，８，８ａ，９，１０，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−ドデカヒドロ−６ｂＨ−ピセン−２−オン；
３−ヒドロキシ−４，６ｂ，８ａ，１１，１２ｂ，１４ａ−ヘキサメチル−７，８，８ａ，１１，１２，１２ａ，１２ｂ，１３，１４，１４ａ−デカヒドロ−６ｂＨ，９Ｈ−ピセン−２，１０−ジオン
でない。 In another preferred embodiment, the compound of formula (Ia) is of formula (Ia ″):

[Where:
R ₇ and R ₈ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (here R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or each pair forms a (C═O) group with the carbon to which they are attached. Can do;
R ₁₅ is hydrogen or halogen;
R ₁₉ is hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ Aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl -O- _(C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 to 3); or trifluoromethyl; and,
Join

Means a double bond or a single bond]
Comprising a structure having
Provided that the compound of formula (Ia ″) is
3-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-dodecahydro-6bH-picene-2- on;
3-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene-2,10- Not dione.

As a specific example of this structure (Ia ″):
14-bromo-3-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene- 2,10-dione (C7);
4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-tetradeca Hydro-picen-3-yl acetate (C8);
4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-tetradeca Hydro-picen-3-ylnicotinic acid ester (C9);
3,10-dihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-dodecahydro-6bH-picene- 2-one (C10);
3-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 12a, 12b, 13,14,14a-octahydro-6bH, 9H-picene-2,10-dione (C11)
There is.

［式中、
Ｒ_７は水素、ヒドロキシル、ハロゲン、置換もしくは非置換Ｃ_１−Ｃ_１２アルキル、置換もしくは非置換Ｃ_６−Ｃ_１０アリール、またはＮ（Ｒ’）（Ｒ’’）アミノ基（ここで、Ｒ’およびＲ’’は独立に水素またはＣ_１−Ｃ_１２アルキル基である）であり；かつ、
Ｒ_１９は置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１〜３の間である）；またはトリフルオロメチルである］
を有する構造を含んでなり、
ただし、式（Ｉａ’’’）の化合物は、
３，１０−ジヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−１１−オキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−２−カルボン酸メチルエステル；
１０−ヒドロキシ−２，４ａ，６ａ，９，１２ｂ，１４ａ−ヘキサメチル−１１−オキソ−１，２，３，４，４ａ，５，６，６ａ，１１，１２ｂ，１３，１４，１４ａ，１４ｂ−テトラデカヒドロ−ピセン−２−カルボン酸メチルエステル
でない。 In another preferred embodiment, the compound of formula (Ia) has the formula (Ia ′ ″):

[Where:
R ₇ is hydrogen, hydroxyl, halogen, substituted or unsubstituted C ₁ -C ₁₂ alkyl, substituted or unsubstituted C ₆ -C ₁₀ aryl, or N (R ′) (R ″) amino group (where R ′ And R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); and
R ₁₉ is substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group (where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; Or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl-O -(C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); or trifluoromethyl]
Comprising a structure having
Provided that the compound of formula (Ia ′ ″) is
3,10-dihydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester;
10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b- Not tetradecahydro-picene-2-carboxylic acid methyl ester.

As a specific example of this structure (Ia ''')
2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-10-propionyloxy-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b -Tetradecahydro-picene-2-carboxylic acid methyl ester (C13);
10-dimethylcarbamoyloxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b-Tetradecahydro-picene-2-carboxylic acid methyl ester (C14)
There is.

［式中、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_７、Ｒ_８、Ｒ_１１およびＲ_１２は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ’）（Ｒ’’）アミノ基（ここで、Ｒ’およびＲ’’は独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_９およびＲ_１０は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ’’’基｛ここで、Ｒ’’’は水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｏ−Ｃ_１−Ｃ_１２アルキル；またはＮ（Ｒ^ＩＶ）（Ｒ^Ｖ）アミノ（ここで、Ｒ^ＩＶおよびＲ^Ｖは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；（ＣＨ_２）_ｎ−ＯＨカルビノール基（ここで、ｎは１〜１０の間の整数である）であるか；あるいは一緒にメチレン基を形成し；
Ｒ_１３、Ｒ_１４、Ｒ_１５、Ｒ_１６、Ｒ_２１、Ｒ_２２およびＲ_２３は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＶＩ）（Ｒ^ＶＩＩ）アミノ基（ここで、Ｒ^ＶＩおよびＲ^ＶＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_１７は水素またはメチルであり；
Ｒ_１８は水素；ヒドロキシル；ハロゲン；Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＩＸ｛ここで、Ｒ^ＩＸは水素；ヒドロキシル；Ｃ_１−Ｃ_１２アルキル；Ｎ（Ｒ^Ｘ）（Ｒ^ＸＩ）アミノ（ここで、Ｒ^ＸおよびＲ^ＸＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；またはＣ_１−Ｃ_１２アルコキシルである｝；またはトリフルオロメチルであり；
Ｒ_１９およびＲ_２０は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；またはトリフルオロメチルであり；
結合

は二重結合または単結合を意味し、
ただし、Ｒ_１９およびＲ_２０が独立に水素またはアシル基である場合、
Ｒ_５はヒドロキシルであるか、または
Ｒ_２１およびＲ_２２はそれらが結合している炭素と一緒にＣ＝Ｏ基を形成し、かつ、Ｒ_１０はＣＯＯＨでない］
の化合物を対象とする。 In another specific embodiment, the invention provides a compound of formula (Ib):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or is unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or C ₁ -C ₁₂ alkyl group) Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₂₁ , R ₂₂ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl Are N (R ^VI ) (R ^VII ) amino groups, where R ^VI and R ^VII are independently hydrogen or C ₁ -C ₁₂ alkyl groups; or each pair is Can form a (C═O) group with the carbon present;
R ₁₇ is hydrogen or methyl;
R ₁₈ is hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (wherein R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl;
R ₁₉ and R ₂₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂₎ alkyl _-O- (C 1 _{-C 12)} alkyl - _{in] n} group (where, n is between 1 and 3); or trifluoromethyl;
Join

Means a double bond or a single bond,
Provided that when R ₁₉ and R ₂₀ are independently hydrogen or an acyl group,
R ₅ is hydroxyl, or R ₂₁ and R ₂₂ together with the carbon to which they are attached form a C═O group, and R ₁₀ is not COOH]
The target compounds are as follows.

［式中、
Ｒ_１９およびＲ_２０は独立に置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；またはトリフルオロメチルである］
を有する構造を含んでなる。 In another preferred embodiment, the compound of formula (Ib) has the formula (Ib ′):

[Where:
R ₁₉ and R ₂₀ are independently substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ —C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂₎ alkyl _-O- (C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 and 3); or trifluoromethyl]
The structure which has this.

  Specific examples of this structure (Ib ′) include 4-nitro- (3-dimethylcarbamoyloxy-5,9-dihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-10-oxo-5, 6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-tetradecahydro-picen-2-yl) benzoic acid ester (C15).

［式中、
Ｒ_１８は水素；ヒドロキシル；ハロゲン；Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＩＸ｛ここで、Ｒ^ＩＸは水素；ヒドロキシル；Ｃ_１−Ｃ_１２アルキル；Ｎ（Ｒ^Ｘ）（Ｒ^ＸＩ）アミノ（ここで、Ｒ^ＸおよびＲ^ＸＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；またはＣ_１−Ｃ_１２アルコキシルである｝；またはトリフルオロメチルであり；
Ｒ_１９は水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；またはトリフルオロメチルであり；
Ｒ_２３は水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＶＩ）（Ｒ^ＶＩＩ）アミノ基（ここで、Ｒ^ＶＩおよびＲ^ＶＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である］
を有する構造を含んでなる。 In another preferred embodiment, the compound of formula (Ib) has the formula (Ib ″):

[Where:
R ₁₈ is hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (wherein R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl;
R ₁₉ is hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ Aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl -O- _(C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 and 3); or trifluoromethyl;
R ₂₃ is hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^VI ) (R ^VII ) amino group (where R ^VI and R ^VII is a is) independently hydrogen or _C 1 _{-C 12} alkyl radical
The structure which has this.

As a specific example of this structure (Ib ″),
7,10,11-trihydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-8-oxo-1,2,3,4,4a, 5,6,6a, 8,12b, 13,14 , 14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester (F16);
9-formyl-10,11-dihydroxy-2,4a, 6a, 12b, 14a-pentamethyl-8-oxo-1,2,3,4,4a, 5,6,6a, 8,12b, 13,14, 14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester (C17);
11-hydroxy-10- (2-methoxy-ethoxymethoxy) -2,4a, 6a, 9,12b, 14a-hexamethyl-8-oxo-1,2,3,4,4a, 5,6,6a, 8 , 12b, 13, 14, 14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester (C18)
There is.

［式中、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_７、Ｒ_８、Ｒ_１１およびＲ_１２は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ’）（Ｒ’’）アミノ基（ここで、Ｒ’およびＲ’’は独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_９およびＲ_１０は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ’’’基｛ここで、Ｒ’’’は水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｏ−Ｃ_１−Ｃ_１２アルキル；またはＮ（Ｒ^ＩＶ）（Ｒ^Ｖ）アミノ（ここで、Ｒ^ＩＶおよびＲ^Ｖは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；（ＣＨ_２）_ｎ−ＯＨカルビノール基（ここで、ｎは１〜１０の間の整数である）であるか；あるいは一緒にメチレン基を形成し；
Ｒ_１３、Ｒ_１４、Ｒ_１５、Ｒ_１６、Ｒ_２１およびＲ_２３は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＶＩ）（Ｒ^ＶＩＩ）アミノ基（ここで、Ｒ^ＶＩおよびＲ^ＶＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_１８は水素；ヒドロキシル；ハロゲン；Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＩＸ｛ここで、Ｒ^ＩＸは水素；ヒドロキシル；Ｃ_１−Ｃ_１２アルキル；Ｎ（Ｒ^Ｘ）（Ｒ^ＸＩ）アミノ（ここで、Ｒ^ＸおよびＲ^ＸＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；またはＣ_１−Ｃ_１２アルコキシルである｝；またはトリフルオロメチルであり；
Ｒ_１９およびＲ_２０は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；またはトリフルオロメチルであり；
結合

は、二重結合または単結合を意味し、
ただし、Ｒ_１９およびＲ_２０が双方ともＣＨ_３である場合、Ｒ_１５およびＲ_１６はそれらが結合している炭素と一緒にＣ＝Ｏ基を形成しない］
の化合物を対象とする。 In another specific aspect, the invention provides a compound of formula (Ic):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or is unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or C ₁ -C ₁₂ alkyl group) Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₂₁ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N ( R ^VI ) (R ^VII ) amino group (where R ^VI and R ^VII are independently hydrogen or C ₁ -C ₁₂ alkyl groups); or each pair is bound to the carbon to which they are attached. Together can form a (C═O) group;
R ₁₈ is hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (wherein R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl;
R ₁₉ and R ₂₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂₎ alkyl _-O- (C 1 _{-C 12)} alkyl - _{in] n} group (where, n is between 1 and 3); or trifluoromethyl;
Join

Means a double bond or a single bond,
However, when R ₁₉ and R ₂₀ are both CH ₃ , R ₁₅ and R ₁₆ do not form a C═O group with the carbon to which they are attached.]
The target compounds are as follows.

［式中、
Ｒ_１９およびＲ_２０は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；またはトリフルオロメチルであり；
結合

は、二重結合または単結合を意味する］
を有する構造を含んでなる。 In a preferred embodiment, the compound of formula (Ic) has the formula (Ic ′):

[Where:
R ₁₉ and R ₂₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂₎ alkyl _-O- (C 1 _{-C 12)} alkyl - _{in] n} group (where, n is between 1 and 3); or trifluoromethyl;
Join

Means a double bond or a single bond]
The structure which has this.

As a specific example of this structure (Ic ′),
10,11-dihydroxy-2,4a, 6a, 9,14a-pentamethyl-1,4,4a, 5,6,6a, 13,14,14a, 14b-decahydro-2H-picen-3-one (C19) ;
10,11-dihydroxy-2,4a, 6a, 9,14a-pentamethyl-4a, 5,6,6a, 13,14,14a, 14b-octahydro-4H-picen-3-one (C20)
There is.

［式中、
Ｒ_１９およびＲ_２０は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；またはトリフルオロメチルである］
を有する構造を含んでなる。 In another preferred embodiment, the compound of formula (Ic) has the following formula (Ic ″):

[Where:
R ₁₉ and R ₂₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ —C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); or trifluoromethyl]
The structure which has this.

  Specific examples of this structure (Ic ″) include 10,11-dihydroxy-2,4a, 6a, 9,14a-pentamethyl-1,2,3,4,4a, 5,6,6a, 13, There is 14,14a, 14b-dodecahydro-picene-2-carboxylic acid methyl ester (C21).

［式中、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_７、Ｒ_８、Ｒ_１１およびＲ_１２は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ’）（Ｒ’’）アミノ基（ここで、Ｒ’およびＲ’’は独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_９およびＲ_１０は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ’’’基｛ここで、Ｒ’’’は水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｏ−Ｃ_１−Ｃ_１２アルキル；またはＮ（Ｒ^ＩＶ）（Ｒ^Ｖ）アミノ（ここで、Ｒ^ＩＶおよびＲ^Ｖは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；（ＣＨ_２）_ｎ−ＯＨカルビノール基（ここで、ｎは１〜１０の間の整数である）であるか；あるいは一緒にメチレン基を形成し；
Ｒ_１３、Ｒ_１５、Ｒ_２１およびＲ_２３は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＶＩ）（Ｒ^ＶＩＩ）アミノ基（ここで、Ｒ^ＶＩおよびＲ^ＶＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_１８は水素；ヒドロキシル；ハロゲン；Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＩＸ｛ここで、Ｒ^ＩＸは水素；ヒドロキシル；Ｃ_１−Ｃ_１２アルキル；Ｎ（Ｒ^Ｘ）（Ｒ^ＸＩ）アミノ（ここで、Ｒ^ＸおよびＲ^ＸＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；またはＣ_１−Ｃ_１２アルコキシルである｝；またはトリフルオロメチルであり；
Ｒ_１９、Ｒ_１９’、Ｒ_２０およびＲ_２０’は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；トリフルオロメチルであるか；あるいは各１９−１９’または２０−２０’対は、それらが結合している炭素と一緒にＣ＝Ｏ基を形成することができ；
Ｒ_２４およびＲ_２５は独立に水素、ヒドロキシルまたはハロゲンであり；
結合

は、二重結合または単結合を意味する］
の化合物を対象とする。 In another specific aspect, the invention provides a compound of formula (Id):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or is unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or C ₁ -C ₁₂ alkyl group) Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
R ₁₃ , R ₁₅ , R ₂₁ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^VI ) (R ^VII ) An amino group (where R ^VI and R ^VII are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or each pair together with the carbon to which they are attached (C═O ) Groups can be formed;
R ₁₈ is hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (wherein R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ and R ₂₅ are independently hydrogen, hydroxyl or halogen;
Join

Means a double bond or a single bond]
The target compounds are as follows.

［式中、
Ｒ_５およびＲ_６は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ’）（Ｒ’’）アミノ基（ここで、Ｒ’およびＲ’’は独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_１９、Ｒ_１９’、Ｒ_２０およびＲ_２０’は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；トリフルオロメチルであるか；あるいは各１９−１９’または２０−２０’対は、それらが結合している炭素と一緒にＣ＝Ｏ基を形成することができ；
Ｒ_２４およびＲ_２５は独立に水素、ヒドロキシルまたはハロゲンである］
を有する構造を含んでなる。 In a preferred embodiment, the compound of formula (Id) has the formula (Id ′):

[Where:
R ₅ and R ₆ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (here R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or each pair forms a (C═O) group with the carbon to which they are attached. Can do;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ and R ₂₅ are independently hydrogen, hydroxyl or halogen]
The structure which has this.

As a specific example of this structure (Id ′):
1-bromo-9-hydroxy-4,6b, 8a, 11,12b, 14b-hexamethyl-6b, 7,8,8a, 9,11,12,12a, 12b, 14b-decahydro-1H-picene-2, 3,10-trione (C22);
1-bromo-4,6b, 8a, 11,12b, 14b-hexamethyl-6b, 7,8,8a, 9,11,12,12a, 12b, 14b-decahydro-1H-picene-2,3,10- Trion (C23)
There is.

［式中、
Ｒ_１９、Ｒ_１９’、Ｒ_２０およびＲ_２０’は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；トリフルオロメチルであるか；あるいは各１９−１９’または２０−２０’対は、それらが結合している炭素と一緒にＣ＝Ｏ基を形成することができ；
Ｒ_２４およびＲ_２５は独立に水素、ヒドロキシルまたはハロゲンである］
を有する構造を含んでなる。 In another preferred embodiment, the compound of formula (Id) has the formula (Id ″):

[Where:
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ and R ₂₅ are independently hydrogen, hydroxyl or halogen]
The structure which has this.

  Specific examples of this structure (Id ″) include 12-bromo-2,4a, 6a, 9,12a, 14a-hexamethyl-10,11-dioxo-1,2,3,4,4a, 5 6,6a, 10,11,12,12a, 14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester (C24).

［式中、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_７、Ｒ_８、Ｒ_１１およびＲ_１２は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ’）（Ｒ’’）アミノ基（ここで、Ｒ’およびＲ’’は独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_９およびＲ_１０は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ’’’基｛ここで、Ｒ’’’は水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｏ−Ｃ_１−Ｃ_１２アルキル；またはＮ（Ｒ^ＩＶ）（Ｒ^Ｖ）アミノ（ここで、Ｒ^ＩＶおよびＲ^Ｖは独立に水素またはアルキル基Ｃ_１−Ｃ_１２である）である｝；カルビノール基（ＣＨ_２）_ｎ−ＯＨ（ここで、ｎは１〜１０の間の整数である）であるか；あるいは一緒にメチレン基を形成し；
Ｒ_１３、Ｒ_１４、Ｒ_１５、Ｒ_１６、Ｒ_２１およびＲ_２３は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＶＩ）（Ｒ^ＶＩＩ）アミノ基（ここで、Ｒ^ＶＩおよびＲ^ＶＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_１８およびＲ_１８’は独立に水素；ヒドロキシル；ハロゲン；Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＩＸ｛ここで、Ｒ^ＩＸは水素；ヒドロキシル；Ｃ_１−Ｃ_１２アルキル；Ｎ（Ｒ^Ｘ）（Ｒ^ＸＩ）アミノ（ここで、Ｒ^ＸおよびＲ^ＸＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；またはＣ_１−Ｃ_１２アルコキシルである｝；またはトリフルオロメチルであり；
Ｒ_１９、Ｒ_１９’、Ｒ_２０およびＲ_２０’は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；トリフルオロメチルであるか；あるいは各１９−１９’または２０−２０’対は、それらが結合している炭素と一緒にＣ＝Ｏ基を形成することができ；
Ｒ_２４は水素、ヒドロキシルまたはハロゲンであり；
結合

は、二重結合または単結合を意味する］
の化合物を対象とする。 In another specific aspect, the invention provides a compound of formula (Ie):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or is unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or C ₁ -C ₁₂ alkyl group) Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently Is a hydrogen or alkyl group C ₁ -C ₁₂ )}; a carbinol group (CH ₂ ) _n —OH (where n is an integer between 1 and 10); or together with methylene Forming a group;
R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₂₁ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N ( R ^VI ) (R ^VII ) amino group (where R ^VI and R ^VII are independently hydrogen or C ₁ -C ₁₂ alkyl groups); or each pair is bound to the carbon to which they are attached. Together can form a (C═O) group;
R ₁₈ and R _{18 ′} are independently hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (where R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl Yes;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ is hydrogen, hydroxyl or halogen;
Join

Means a double bond or a single bond]
The target compounds are as follows.

［式中、
Ｒ_１８およびＲ_１８’は独立に水素；ヒドロキシル；ハロゲン；Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＩＸ｛ここで、Ｒ^ＩＸは水素；ヒドロキシル；Ｃ_１−Ｃ_１２アルキル；Ｎ（Ｒ^Ｘ）（Ｒ^ＸＩ）アミノ（ここで、Ｒ^ＸおよびＲ^ＸＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；またはＣ_１−Ｃ_１２アルコキシルである｝；またはトリフルオロメチルであり；
Ｒ_１９、Ｒ_１９’、Ｒ_２０およびＲ_２０’は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基｛ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；トリフルオロメチルであるか；あるいは各１９−１９’または２０−２０’対は、それらが結合している炭素と一緒にＣ＝Ｏ基を形成することができ；
Ｒ_２４は水素、ヒドロキシルまたはハロゲンである］
を有する構造を含んでなる。 In a preferred embodiment, the compound of formula (Ie) has the formula (Ie ′):

[Where:
R ₁₈ and R _{18 ′} are independently hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (where R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl Yes;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ is hydrogen, hydroxyl or halogen]
The structure which has this.

  Specific examples of this structure (Ie ′) include 9-hydroxy-2,4a, 6a, 9,12b-hexamethyl-10,11-dioxo-1,2,3,4,4a, 5,6,6a. 9, 10, 11, 12b, 13, 14, 14a, 14b-hexadecahydro-picene-2-carboxylic acid methyl ester (C25).

［式中、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_７、Ｒ_８、Ｒ_１１およびＲ_１２は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ’）（Ｒ’’）アミノ基（ここで、Ｒ’およびＲ’’は独立に水素またはＣ_１−Ｃ_１２アルキル基である）；であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_９およびＲ_１０は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ’’’基｛ここで、Ｒ’’’は水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｏ−Ｃ_１−Ｃ_１２アルキル；またはＮ（Ｒ^ＩＶ）（Ｒ^Ｖ）アミノ（ここで、Ｒ^ＩＶおよびＲ^Ｖは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；（ＣＨ_２）_ｎ−ＯＨカルビノール基（ここで、ｎは１〜１０の間の整数である）であるか；あるいは一緒にメチレン基を形成し；
Ｒ_１３、Ｒ_１４、Ｒ_１５、Ｒ_２１およびＲ_２３は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＶＩ）（Ｒ^ＶＩＩ）アミノ基（ここで、Ｒ^ＶＩおよびＲ^ＶＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_１８およびＲ_１８’は独立に水素；ヒドロキシル；ハロゲン；Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＩＸ｛ここで、Ｒ^ＩＸは水素；ヒドロキシル；Ｃ_１−Ｃ_１２アルキル；Ｎ（Ｒ^Ｘ）（Ｒ^ＸＩ）アミノ（ここで、Ｒ^ＸおよびＲ^ＸＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；またはＣ_１−Ｃ_１２アルコキシルである｝；またはトリフルオロメチルであり；
Ｒ_１９、Ｒ_１９’、Ｒ_２０およびＲ_２０’は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基（ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリールである）；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；トリフルオロメチルであるか；あるいは各１９−１９’または２０−２０’対は、それらが結合している炭素と一緒にＣ＝Ｏ基を形成することができ；
Ｒ_２４は独立に水素、ヒドロキシルまたはハロゲンであり；
結合

は、二重結合または単結合を意味する］
の化合物を対象とする。 In another specific aspect, the invention provides a compound of formula (If):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or an unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group, where R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group; Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
R ₁₃ , R ₁₄ , R ₁₅ , R ₂₁ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^VI ) (R ^VII ) an amino group, where R ^VI and R ^VII are independently hydrogen or a C ₁ -C ₁₂ alkyl group; or each pair together with the carbon to which they are attached ( C = O) groups can be formed;
R ₁₈ and R _{18 ′} are independently hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (where R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl Yes;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group (where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C _1- C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl); or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ is independently hydrogen, hydroxyl or halogen;
Join

Means a double bond or a single bond]
The target compounds are as follows.

［式中、
Ｒ_１８およびＲ_１８’は独立に水素；ヒドロキシル；ハロゲン；Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＩＸ｛ここで、Ｒ^ＩＸは水素；ヒドロキシル；Ｃ_１−Ｃ_１２アルキル；Ｎ（Ｒ^Ｘ）（Ｒ^ＸＩ）アミノ（ここで、Ｒ^ＸおよびＲ^ＸＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；またはＣ_１−Ｃ_１２アルコキシルである｝；またはトリフルオロメチルであり；
Ｒ_１９、Ｒ_１９’、Ｒ_２０およびＲ_２０’は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＩＩ基（ここで、Ｒ^ＸＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリールである）；またはＮ（Ｒ^ＸＩＩＩ）（Ｒ^ＸＩＶ）アミノ（ここで、Ｒ^ＸＩＩＩおよびＲ^ＸＩＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；トリフルオロメチルであるか；あるいは各１９−１９’または２０−２０’対は、それらが結合している炭素と一緒にＣ＝Ｏ基を形成することができ；
Ｒ_２４は独立に水素、ヒドロキシルまたはハロゲンである］
を有する構造を含んでなる。 In a preferred embodiment, the compound of formula (If) has the formula (If ′):

[Where:
R ₁₈ and R _{18 ′} are independently hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (where R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl Yes;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group (where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C _1- C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl); or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ is independently hydrogen, hydroxyl or halogen.
The structure which has this.

  Specific examples of this structure (If ′) include 9-hydroxy-2,4a, 6a, 6b, 9-hexamethyl-10,11-dioxo-1,2,3,4,4a, 5,6,6a. , 6b, 8a, 9, 10, 11, 14, 14a, 14b-hexadecahydro-picene-2-carboxylic acid methyl ester (C26).

［式中、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_９、Ｒ_１０、Ｒ_１１、Ｒ_１２、Ｒ_１３、Ｒ_１４、Ｒ_１５、Ｒ_１６、Ｒ_１７、Ｒ_１８、Ｒ_１９およびＲ_２０は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（ＲＸ^ＸＶ）（Ｒ^ＸＶＩ）アミノ基（ここで、Ｒ^ＸＶおよびＲ^ＸＶＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒にカルボキシル（Ｃ＝Ｏ）基を形成することができ；
Ｒ_７およびＲ_８は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＸＶＩＩ基｛ここで、Ｒ^ＸＶＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｏ−Ｃ_１−Ｃ_１２アルキル；またはＮ（Ｒ^{ＸＶＩＩＩ}）（Ｒ^ＸＩＸ）アミノ（ここで、Ｒ^{ＸＶＩＩＩ}およびＲ^ＸＩＸは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；（ＣＨ_２）_ｎ−ＯＨカルビノール基（ここで、ｎは１〜１０の間の整数である）であるか；あるいは一緒にメチレン基を形成し、
Ｒ_２１およびＲ_２４は独立に置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＸ基｛ここで、Ｒ^ＸＸは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＸＩ）（Ｒ^ＸＸＩＩ）アミノ（ここで、Ｒ^ＸＸＩおよびＲ^ＸＸＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１〜３の間である）；またはトリフルオロメチルであり；
Ｒ_２２およびＲ_２３は、
Ｒ_２４がＲ_２０に対してパラ位にある場合には、水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^{ＸＸＩＩＩ}基｛ここで、Ｒ^{ＸＸＩＩＩ}は水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＸＩＶ）（Ｒ^ＸＸＶ）アミノ（ここで、Ｒ^ＸＸＩＶおよびＲ^ＸＸＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１〜３の間である）；またはトリフルオロメチルであるか；あるいは
Ｒ_２４がＲ_２０に対してメタ位にある場合には、それぞれＯＲ_２２’およびＯＲ_２３’であり、ここで、Ｒ_２２’およびＲ_２３’は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＸＶＩ基｛ここで、Ｒ^ＸＸＶＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^{ＸＸＶＩＩ}）（Ｒ^{ＸＸＶＩＩＩ}）アミノ（ここで、Ｒ^{ＸＸＶＩＩ}およびＲ^{ＸＸＶＩＩＩ}は独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；またはトリフルオロメチルである］
の化合物、またはその薬学上許容される塩、誘導体、プロドラッグ、溶媒和物もしくは立体異性体である。 Another aspect of the invention is a compound of formula (II):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₉ , R ₁₀ , R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₁₇ , R ₁₈ , R ₁₉ And R ₂₀ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (RX ^XV ) (R ^XVI ) amino group (where R or ^XV and R ^XVI are are independently hydrogen or C ₁ -C ₁₂ alkyl group); or each pair, to form them bonded to and carboxyl (C = O) group together with the carbon Can;
R ₇ and R ₈ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^XVII group {where R ^XVII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted _C 6 _{-C 10 aryl; O-C} 1 _{-C 12} alkyl; with or ^{N (R XVIII) (R XIX} ) amino ^{(wherein, R XVIII} and ^{R XIX} are independently hydrogen or _{C 1} Is a —C ₁₂ alkyl group)}; (CH ₂ ) _n —OH carbinol group (where n is an integer between 1 and 10); or together forms a methylene group. ,
R ₂₁ and R ₂₄ are independently substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XX group {where R ^XX is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ —C ₁₀ aryl; or N (R ^XXI ) (R ^XXII ) amino, where R ^XXI and R ^XXII are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂₎ alkyl _-O- (C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 to 3); or trifluoromethyl;
R ₂₂ and R ₂₃ are
When R ₂₄ is para to R ₂₀ , hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XXIII group {where R ^XXIII is hydrogen; hydroxyl; substituted or unsubstituted C _1- C ₁₂ alkyl; substituted or unsubstituted _C 6 _{-C 10} aryl; or ^N (R ^{XXIV) (R XXV)} amino ^{(wherein, R XXIV} and ^{R XXV} are independently hydrogen or _C 1 _{-C 12} alkyl group) Or [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); or is trifluoromethyl? Or, when R ₂₄ is in the meta position relative to R ₂₀ , OR ₂₂ ′ and OR ₂₃ ′, respectively, where R ₂₂ ′ and R ₂₃ ′ are independently hydrogen; Here ^{COR XXVI} group ^{{, R XXVI} is ^hydrogen; unsubstituted _C 1 _{-C 12} alkyl hydroxyl; substituted or unsubstituted _C 1 _{-C 12} alkyl; substituted or unsubstituted _C 6 _{-C 10} aryl; or N (R ^XXVII ) (R ^XXVIII ) amino where R ^XXVII and R ^XXVIII are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl-O- (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); or trifluoromethyl]
Or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof.

［式中、
Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_９、Ｒ_１０、Ｒ_１１、Ｒ_１２、Ｒ_１３、Ｒ_１４、Ｒ_１５、Ｒ_１６、Ｒ_１７、Ｒ_１８、Ｒ_１９およびＲ_２０は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＸＶ）（Ｒ^ＸＶＩ）アミノ基（ここで、Ｒ^ＸＶおよびＲ^ＸＶＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）基を形成することができ；
Ｒ_７およびＲ_８は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；Ｃ_６−Ｃ_１０アリール；ＣＯＲ^ＸＶＩＩ基｛ここで、Ｒ^ＸＶＩＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｏ−Ｃ_１−Ｃ_１２アルキル；またはＮ（Ｒ^{ＸＶＩＩＩ}）（Ｒ^ＸＩＸ）アミノ（ここで、Ｒ^{ＸＶＩＩＩ}およびＲ^ＸＩＸは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；（ＣＨ_２）_ｎ−ＯＨカルビノール基（ここで、ｎは１〜１０の間の整数である）であるか；あるいは一緒にメチレン基を形成し；
Ｒ_２１およびＲ_２４は独立に置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＸ基（ここで、Ｒ^ＸＸは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＸＩ）（Ｒ^ＸＸＩＩ）アミノ（ここで、Ｒ^ＸＸＩおよびＲ^ＸＸＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；またはトリフルオロメチルであり；
Ｒ_２２およびＲ_２３は、
Ｒ_２４がＲ_２０に対してパラ位にある場合には、水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^{ＸＸＩＩＩ}基｛ここで、Ｒ^{ＸＸＩＩＩ}は水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^ＸＸＩＶ）（Ｒ^ＸＸＶ）アミノ（ここで、Ｒ^ＸＸＩＶおよびＲ^ＸＸＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１〜３の間である）；またはトリフルオロメチルであるか；あるいは
Ｒ_２４がＲ_２０に対してメタ位にある場合には、それぞれＯＲ_２２’およびＯＲ_２３’であり、ここで、Ｒ_２２’およびＲ_２３’は独立に水素；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；ＣＯＲ^ＸＸＶＩ基｛ここで、Ｒ^ＸＸＶＩは水素；ヒドロキシル；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；またはＮ（Ｒ^{ＸＸＶＩＩ}）（Ｒ^{ＸＸＶＩＩＩ}）アミノ（ここで、Ｒ^{ＸＸＶＩＩ}およびＲ^{ＸＸＶＩＩＩ}は独立に水素またはＣ_１−Ｃ_１２アルキル基である）である｝；［（Ｃ_１−Ｃ_１２）アルキル−Ｏ−（Ｃ_１−Ｃ_１２）アルキル−］_ｎ基（ここで、ｎは１から３の間である）；またはトリフルオロメチルである］
の化合物を対象とする。 In one particular embodiment, the invention provides a compound of formula (IIa):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₉ , R ₁₀ , R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₁₇ , R ₁₈ , R ₁₉ And R ₂₀ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^XV ) (R ^XVI ) amino group (where R ^XV and R ^XVI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or each pair can form a (C═O) group with the carbon to which they are attached. ;
R ₇ and R ₈ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^XVII group {where R ^XVII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted _C 6 _{-C 10 aryl; O-C} 1 _{-C 12} alkyl; with or ^{N (R XVIII) (R XIX} ) amino ^{(wherein, R XVIII} and ^{R XIX} are independently hydrogen or _{C 1} Is a —C ₁₂ alkyl group)}; (CH ₂ ) _n —OH carbinol group (where n is an integer between 1 and 10); or together forms a methylene group. ;
R ₂₁ and R ₂₄ are independently substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XX group (where R ^XX is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ —C ₁₀ aryl; or N (R ^XXI ) (R ^XXII ) amino, where R ^XXI and R ^XXII are independently hydrogen or a C ₁ -C ₁₂ alkyl group; and [(C ₁ -C ₁₂ ) alkyl. -O- _(C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 and 3); or trifluoromethyl;
R ₂₂ and R ₂₃ are
When R ₂₄ is para to R ₂₀ , hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XXIII group {where R ^XXIII is hydrogen; hydroxyl; substituted or unsubstituted C _1- C ₁₂ alkyl; substituted or unsubstituted _C 6 _{-C 10} aryl; or ^N (R ^{XXIV) (R XXV)} amino ^{(wherein, R XXIV} and ^{R XXV} are independently hydrogen or _C 1 _{-C 12} alkyl group) Or [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); or is trifluoromethyl? Or, when R ₂₄ is in the meta position relative to R ₂₀ , OR ₂₂ ′ and OR ₂₃ ′, respectively, where R ₂₂ ′ and R ₂₃ ′ are independently hydrogen; Here ^{COR XXVI} group ^{{, R XXVI} is ^hydrogen; unsubstituted _C 1 _{-C 12} alkyl hydroxyl; substituted or unsubstituted _C 1 _{-C 12} alkyl; substituted or unsubstituted _C 6 _{-C 10} aryl; or N (R ^XXVII ) (R ^XXVIII ) amino where R ^XXVII and R ^XXVIII are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl-O- (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); or trifluoromethyl]
The target compounds are as follows.

［式中、
Ｒ_１９およびＲ_２０は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＸＶ）（Ｒ^ＸＶＩ）アミノ基（ここで、Ｒ^ＸＶおよびＲ^ＸＶＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか；あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）カルボキシル基を形成することができ；
Ｒ_２１およびＲ_２４は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＸＸＩ）（Ｒ^ＸＸＩＩ）アミノ基（ここで、Ｒ^ＸＸＩおよびＲ^ＸＸＩＩは独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか、あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）カルボキシル基を形成することができ；
Ｒ_２２およびＲ_２３は独立に水素；ヒドロキシル；ハロゲン；置換もしくは非置換Ｃ_１−Ｃ_１２アルキル；置換もしくは非置換Ｃ_６−Ｃ_１０アリール；Ｎ（Ｒ^ＸＸＩＶ）（Ｒ^ＸＸＶ）アミノ基（ここで、Ｒ^ＸＸＩＶおよびＲ^ＸＸＶは独立に水素またはＣ_１−Ｃ_１２アルキル基である）であるか、あるいは各対は、それらが結合している炭素と一緒に（Ｃ＝Ｏ）カルボキシル基を形成することができる］
を有する構造を含んでなる。 In a preferred embodiment, the compound of formula (IIa) has the formula (IIa ′):

[Where:
R ₁₉ and R ₂₀ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^XV ) (R ^XVI ) amino group (where , R ^XV and R ^XVI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or each pair forms a (C═O) carboxyl group with the carbon to which they are attached. It is possible;
R ₂₁ and R ₂₄ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^XXI ) (R ^XXII ) amino group (where , R ^XXI and R ^XXII are independently hydrogen or a C ₁ -C ₁₂ alkyl group), or each pair together with the carbon to which they are attached (C═O) forms a carboxyl group It is possible;
R ₂₂ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^XXIV ) (R ^XXV ) amino group (where R ^XXIV and R ^XXV are independently hydrogen or a C ₁ -C ₁₂ alkyl group) or each pair together with the carbon to which they are attached (C═O) forms a carboxyl group be able to]
The structure which has this.

  A specific example of this structure (IIa ′) is 8- [2- (6,7-dihydroxy-1,5-dimethyl-naphthalen-2-yl) -ethyl] -2,4a-tetramethyl-1, There is 2,3,4,4a, 5,6,7-octahydro-naphthalene-2-carboxylic acid methyl ester (C27).

In another aspect, the invention relates to a process for the preparation of a compound of formula (I) comprising the following characteristics:
a) The conventional method of chemoselective introduction at the C-3 hydroxyl of the natural Friedelane derivative of the pristimerin-related methylenetriterpene quinone of this chemical family includes analysis of the basic conditions for the extraction of phenolic protons and subsequent demonstration Reaction with an acylating agent or another type of drug is required. If pH control is not appropriate, reactions at C-6 occur that complicate the synthesis process.
b) The method of chemoselective introduction of the indicated group at C-23 is carried out by controlled oxidation with reagents specific for the allylic aromatic system and subsequent rearrangement of the functional groups thus obtained.
c) The methods already studied allow C-25 to be rearranged in the fluoromethyl group and reach the group indicated by the subsequent rearrangement of the functional group.
d) The use of heterolytic and homolytic halogenation reactions in conjunction with chemoselective oxidation processes and the introduction of nitrogen by the use of azides is part of any method used to obtain the target.
e) Utilizing the functionalization at C-11, the C11-C12 double bond can be obtained using the methodology studied so far, which is the FGT (functional group rearrangement) for the purpose of producing the intended compound. ) As a functional group for applying to them.
f) Positions C15 and C16 are functionalized from the double bond of ring E or ring C and further from the previous EGT application by carrying out an allyl oxidation reaction.
g) Some starting substrates can be partially functionalized at the C-19, C-20, C-21 and C-22 positions, and chemical methods for the introduction of functional groups in the ring. Has been extensively detailed.

  Although specific examples of the present invention are described in the Preparation Examples section, one of ordinary skill in the art can achieve the synthesis of the described compounds with conventional synthetic compounds present in the art.

  “Pharmaceutically acceptable salt, solvate, prodrug” refers to a pharmaceutically acceptable salt (directly or indirectly) that results in a compound as described herein when administered to a recipient. An acceptable salt, ester, solvate or any other compound. However, pharmaceutically unacceptable salts are also within the scope of the present invention as they can be useful in the manufacture of pharmaceutically acceptable salts. The production of salts, prodrugs and derivatives can be carried out by methods known in the art.

  For example, pharmaceutically acceptable salts of the compounds provided herein are synthesized from the original compound which contains a basic or acidic residue by conventional chemical methods. Such salts are generally prepared, for example, by reacting the free acid or base of the compound with a stoichiometric amount of a suitable base or acid in water or an organic solvent or a mixture of both. Non-aqueous solvents such as ether, ethyl acetate, ethanol, isopropanol or acetonitrile are generally preferred. Examples of acid addition salts include inorganic acid addition salts such as hydrochloride, hydrobromide, hydroiodide, sulfate, nitrate, phosphate, and the like, for example acetate, maleate, fumaric acid Acid addition salts such as organic acid addition salts such as salts, citrate, oxalate, succinate, tartrate, malate, mandelate, methanesulfonate and p-toluenesulfonate. Examples of basic acid addition salts include inorganic acids such as sodium, potassium, calcium, ammonium, magnesium, aluminum and lithium, as well as, for example, ethylenediamine, ethanolamine, N, N-dialkyleneethanolamine, triethanolamine, glucamine and Organic base salts such as basic amino acid salts can be mentioned.

  Particularly preferred derivatives or prodrugs increase the bioavailability of the compounds of the invention when such compounds are administered to a patient (eg, by making the orally administered compounds readily absorbed by the blood) Or it enhances the release of the original compound in the biological compartment (eg brain or lymphatic system) over the original species.

  Any compound that is a prodrug of a compound of formula (I) or formula (II) is within the scope of the invention. "Prodrug" is used in its broadest sense and includes derivatives that are converted in vivo to the compounds of the invention. Such derivatives will be apparent to those skilled in the art and are not limited by the functional groups present in the molecule, but include the following derivatives of this compound: esters, amino acid esters, phosphate esters, metal sulfonate esters. , Carbamates and amides. Examples of methods for producing prodrugs of certain active compounds are known to those skilled in the art and can be found, for example, in Krogsgaard-Larsen et al. “Textbook of Drug design and Discovery” Taylor & Francis (April 2002).

  The compounds of the present invention may exist in crystalline form as free compounds or solvates, both of which are within the scope of the present invention. Solvation methods are generally known in the art. Suitable solvates are pharmaceutically acceptable solvates. In certain embodiments, the solvate is a hydrate.

  The compounds of the invention of formula (I) described so far are enantiomers depending on the presence of chiral centers on C, or isomers depending on the presence of multiple bonds (eg Z, E). The individual isomers, enantiomers or diastereoisomers and mixtures thereof are also included within the scope of the present invention.

  The various substituents selected for the various compounds of the invention result in a series of factors that significantly affect the value of log P. Thus, the hydroxyl group acts as a hydrogen bond donor and intermolecular or intramolecular bonds can be established even in the case of phenol. The presence of a carbonyl group or a carboxyl group gives rise to a proton accepting group in the molecule. The presence of halogen results in very imperfect carbon and greatly alters biological properties. Amino groups produce good nucleophilic atoms on the molecule, in most cases significantly altering their polarity and polarizability, and the presence of additional alkyl and / or aryl groups increases the lipophilicity of the molecule.

  The present invention further provides formula (I), (Ia), (Ia ′), (Ia ″), (Ia ′ ″), (Ib), (Ib ′), (Ib) for administration to a patient. ''), (Ic), (Ic ′), (Ic ″), (Id), (Id ′), (Id ″), (Ie), (Ie ′), (If), (If ′) ), (II), (IIa), (IIa ′) or mixtures thereof, pharmaceutically acceptable salts, derivatives, prodrugs, solvates or stereoisomers thereof, pharmaceutically acceptable carriers, adjuvants or vehicles A pharmaceutical composition comprising is provided.

  These pharmaceutical compositions may be administered by any suitable route of administration, including, for example, oral, topical, rectal or parenteral routes (including subcutaneous, intraperitoneal, intradermal, intramuscular and intravenous routes).

  Dosage forms suitable for oral administration include solid compositions (tablets, pastilles, capsules, granules, etc.) or liquid compositions (solutions, suspensions, emulsions, syrups, etc.), for example syrup, gum arabic Binders such as lactose, saccharides, corn starch, calcium fosfate, calcium fosfate, sorbitol or glycine; eg lubricants for the manufacture of tablets such as magnesium stearate Including conventional excipients known in the art such as disintegrants such as starch, polyvinylpyrrolidone, sodium starch glycolate or microcrystalline cellulose; or pharmaceutically acceptable wetting agents such as sodium lauryl sulfate obtain.

  Solid oral compositions can be prepared by conventional methods of mixing, filling or tableting. Repeated mixing operations can be used to distribute the active ingredient throughout the composition by using large amounts of bulking agent. Such operations are routine in the art. Tablets can be prepared, for example, by wet or dry granulation, and if desired may be coated according to methods well known in normal pharmaceutical practice, in particular enteric coated.

  These pharmaceutical compositions can also be adapted for parenteral administration, such as sterile solutions, suspensions or lyophilized products as suitable unit pharmaceutical forms. Suitable excipients such as drug substances, buffers or surfactants can be used.

  The above-described formulations are prepared using conventional methods such as those described or referenced in the Spanish and US Pharmacopeia and equivalent reference textbooks.

  Administration of the compounds or compositions used in the present invention can be performed by any suitable method such as intravenous infusion, oral formulation, and intraperitoneal and intravenous administration. However, the preferred route of administration depends on the patient's condition. Oral administration is preferred in terms of patient comfort and the chronicity of the disease being treated.

  For their application in therapy, the compounds of formula (I) and formula (II) are found in pharmaceutically acceptable or substantially pure form, ie compounds of formula (I) and formula (II) Preferably contains a pharmaceutically acceptable excipient, but has a pharmaceutically acceptable purity level that does not contain substances that are considered toxic at normal dosage levels. The purity level of the compound of formula (I) or of the compound of formula (II) is preferably more than 50%, more preferably more than 70%, more preferably more than 90%. In preferred embodiments they are greater than 95%.

  The therapeutically effective amount of a compound of formula (I) or formula (II) to be administered will generally be selected among other factors, the individual being treated, the severity of the disease the individual is suffering from, and the dosage chosen. It depends on the shape. For this reason, the doses described in the present invention should be considered as a guide to those skilled in the art and must be adjusted according to the variables mentioned so far. However, the compound of formula (I) may be used at least once a day, for example once, twice, three times or four times, between 1 and 200 mg / kg body weight / day, preferably between 1 and 10 mg / kg body weight / day Can be administered in typical daily total doses. Similarly, the compound of formula (II) is also once or more daily, for example once, twice, three times or four times, 1 to 200 mg / kg body weight / day, preferably 1 to 10 mg / kg body weight / day. Can be administered in a typical total daily dose.

  The compounds described in the present invention, their pharmaceutically acceptable salts, prodrugs and / or solvates, and pharmaceutical compositions containing them should be used in combination therapy with other additional drugs. Can do. The additional agent can form part of the same pharmaceutical composition or comprises a compound of formula (I) or formula (II), or a pharmaceutically acceptable prodrug, solvate or salt thereof. It can also be provided in the form of separate compositions for simultaneous or non-co-administration with the pharmaceutical composition.

  These other agents can form part of the same composition or can be provided as separate compositions for administration at the same time or at different times.

  The final object of the present invention is the use of formulas (I), (Ia), (Ia ′), (Ia ″), (Ia ′) for the treatment of cancer, parasitic diseases, bacterial diseases or fungal diseases. ''), (Ib), (Ib ′), (Ib ″), (Ic), (Ic ′), (Ic ″), (Id), (Id ′), (Id ″), ( Ie), (Ie ′), (If), (If ′), (II), (IIa), (IIa ′) or a mixture thereof, or a pharmaceutically acceptable salt, derivative, prodrug, solvent thereof Consists of Japanese or stereoisomers.

  The following examples are given merely as further illustrations of the invention and should not be construed as limitations of the invention as defined in the claims.

Production example
Example 1
Compound C3: 12-bromo-3,9-dihydroxy-6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H -The bark of the root of Maytenus amazonica of 300 g of picene-2,10-dione was extracted with 2 liters of n-hexane-ethyl ether 1: 1 solvent mixture under reflux with a Soxhlet apparatus for 48 hours. After evaporation of 70 g of a reddish solid was obtained. The extract, as eluent n- hexane -CHCl ₃ -MeOH2: 1: chromatographed on Sephadex LH-20 column using a 1 mixture. A total of 41 fractions were obtained, which were combined into several groups by thin layer chromatography (A, B, C, D, E, F and G). These groups are then fractionated on a Sephadex LH-20 column with medium pressure silica gel columns and preparation plates, and then the starting compound 22β-hydroxy-tingenone or [3,9-hydroxy-6b, 8a, 11, 12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene-2,10-dione].

Under inert atmosphere at 0 ° C., 342 mg (0.78 mmol) of 22β-hydroxy-tingenone in 50 ml of dry CH ₂ Cl _{2 was} treated with 1.5 equivalents of BBr ₃ (1M). The reaction mixture was followed by thin layer chromatography and stirred for 30 minutes until no starting product was present. Then 50 ml of cold distilled water was added and the mixture was stirred for another 30 minutes. Next, extraction with CH ₂ Cl ₂ was performed. The organic phase was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by LH-20 Sephadex chromatography using n-hexane: chloroform: methanol 2: 1: 1 mixture as eluent and silica gel chromatography column using n-hexane-ethyl acetate 7: 3 as eluent. . 111 mg (27%) of product C3 was obtained.

¹ H NMR (300 MHz, CDCl ₃ ) δ 0.50 (3H, s, Me-27); 1.16 (3H, d, J = 5.9 Hz, Me-30); 1.29 (3H, s, Me-26); 1.36 (3H, s, Me-28); 1.44 (3H, s, Me-25); 2.20 (3H, s, Me-23); 2.61 (1H, m, H-20); 3.70 (1H, d, J = 2.9 Hz, H-22); 4.03 (1H, dd, J ₁ = 2.6, J ₂ = 10.2 Hz, H− 19); 6.32 (1H, d, J = 7.2 Hz, H-7); 6.50 (1H, d, J = 1.3 Hz, H-1); 7.00 (1H, dd, J _{1 = 1.3, J 2 = 7.1Hz} , H-6). ¹³ C NMR (75 MHz, CDCl ₃ ) δ 10.2 (c, C-23); 20.3 (c, C-27); 20.9 (c, C-30); 21.7 (c, C -26); 27.9 (t, C-16); 28.0 (t, C-15); 28.9 (t, C-12); 30.9 (c, c-28); 4 (t, C-11); 37.9 (c, c-25); 40.0 (d, C-20); 40.4 (s, C-14); 42.7 (s, c- 9); 44.4 (s, C-13); 45.5 (s, C-17); 48.7 (d, C-18); 76.6 (d, C-19); 77.2 (D, C-22); 118.6 (d, C-7); 119.6 (d, C-1); 127.7 (s, C-5); 133.7 (d, C-6) ); 146.1 (s, C-4); 149.5 (s, C-3); 1 64.1 (s, C-10); 167.9 (s, C-8); 178.4 (s, C-2); 216.5 (s, C-21). High resolution MS C ₂₈ H ₃₆ O ₄ Theoretical 436.2614, Found 436.2695.

Example 2
Compound C7: 14-bromo-3-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H -Picene-2,10-dione 100 mg (0.23 mmol) of 22β-hydroxy-tingenone obtained according to Example 1 was dissolved in 10 ml of CH ₂ Cl ₂ and 82 mg of NBS (2 eq) at room temperature for 2 hours. Was processed. The mixture was followed by TLC and extracted with CH ₂ Cl ₂ when no starting product was present. The organic phase was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography using n-hexane: AcOEt mixture of increasing polarity from 10% to 60% as eluent, and 1.2 mg (1%) of a mixture of compound C7 and other compounds was obtained. Obtained.

¹ H NMR (300 MHz, CDCl ₃ ) δ 0.99 (3H, s, Me-28); 1.00 (3H, d, J = 5.2 Hz, Me-30); 1.01 (3H, s, 1.38 (3H, s, Me-25); 1.76 (3H, s, Me-25); 2.20 (3H, s, Me-23); 4.82 (1H, Me-27); dd, J ₁ = 6.7 Hz, J ₂ = 12.0 Hz, H-11); 6.28 (1H, d, J = 7.0 Hz, H-7); 6.89 (1H, d, J = 7.0 Hz, H-6); 7.35 (1H, s, H-1). ¹³ C NMR (75 MHz, CDCl ₃ ) δ 10.2 (c, C-23); 14.9 (c, C-30); 19.7 (c, C-27); 21.2 (c, C -26); 28.3 (t, C-15); 31.7 (t, C-16); 32.0 (c, c-28); 35.0 (t, C-19); 6 (c, c-25); 38.1 (s, C-13); 41.6 (d, c-18); 42.4 (s, C-14); 42.8 (d, C- 20); 44.3 (s, C-17); 44.9 (t, C-12); 42.8 (s, C-9); 51.6 (t, c-22); 58.3 (D, C-11); 117.9 (s, C-4); 118.4 (d, C-7); 121.1 (d, C-1); 129.6 (s, C-5) 131.4 (d, C-6); 152.9 (s, C-3); 1 62.7 (s, C-10); 165.4 (s, C-8); 178.3 (s, C-2); 212.8 (s, C-21). High resolution MS C ₂₈ H ₃₅ BrO ₃ Theoretical 498.1770, Found 498.1801.

Example 3
Compound C8: (4, 6b, 8a, 11, 12b, 14a-hexamethyl-2, 10-dioxo-2, 6b, 7, 8, 8a, 9, 10, 11, 12, 12a, 12b, 13, 14, 14a-tetradecahydro-picen-3-yl) acetic acid ester 300 g of Metenus Amazonica root bark was extracted with 2 liters of n-hexane-ethyl ether 1: 1 solvent mixture under reflux in a Soxhlet apparatus for 48 hours. After evaporation of the solvent, 70 g of a reddish solid was obtained. The extract, as eluent n- hexane -CHCl ₃ -MeOH2: 1: chromatographed on Sephadex LH-20 column using a 1 mixture. A total of 41 fractions were obtained, which were combined into several groups by thin layer chromatography (A, B, C, D, E, F and G). Next, these groups were fractionated on a Sephadex LH-20 column with a medium pressure silica gel column and a preparation plate to obtain a starting compound called tingenone.

40 mg (0.096 mmol) of tingenone in 10 ml of dry CH ₂ Cl ₂ was treated with 0.04 ml (3 eq) of dry Et ₃ N and 0.01 ml (1.5 eq) of acetyl chloride. The reaction was performed at room temperature, followed by TLC and stirred for 2 hours. The method described in the previous reaction was followed. The crude product was purified by preparative silica gel column chromatography using n-hexane: AcOEt (2: 3) as the mobile phase to give 24 mg (54%) of product C8. The rest was the starting product.

¹ H NMR (300 MHz, CDCl ₃ ) δ 7.08 (1H, dd, J ₁ = 1.3, J ₂ = 7.0 Hz, H-6); 6.50 (1H, d, J = 1.4 Hz) , H-1); 6.35 (1H, d, J = 7.1 Hz, H-7); 2.49 (1H, m, H-20); 2.36 (3H, s, Me-COO) 2.16 (3H, s, Me-23); 1.52 (3H, s, Me-25); 1.35 (3H, s, Me-26); 1.00 (3H, s, Me-) 27); 0.99 (3H, d, J = 6.2 Hz, Me-30); 0.98 (3H, s, Me-28). ¹³ C NMR (75 MHz, CDCl ₃ ) δ 11.1 (c, C-23); 14.8 (c, C-30); 19.5 (c, C-27); 20.3 (c, CH ₃ COO); 21.6 (c, C-26); 28.2 (t, C-15); 29.6 (t, C-12); 31.8 (t, C-19); 3 (c, c-28); 33.6 (t, C-11); 35.2 (t, c-16); 37.9 (s, C-17); 38.8 (c, C-) 25); 40.2 (s, C-13); 41.7 (d, c-20); 42.2 (s, C-9); 43.3 (d, C-18); 44.6 (S, C-14); 52.3 (t, c-22); 117.6 (d, C-7); 122.9 (d, C-1); 126.4 (s, C-5) ); 133.5 (s, C-4); 134.9 (d, C-6) ; 142.8 (s, C-3 ); 162.9 (s, C-10); 168.5 (s, CH 3 COO); 170.4 (s, C-8); 177.3 (s , C-2); 213.4 (s, C-21). High resolution MS C ₃₀ H ₃₈ O ₄ Theoretical 462.2770, Found 462.2784.

Example 4
Compound C9: (4, 6b, 8a, 11, 12b, 14a-hexamethyl-2, 10-dioxo-2, 6b, 7, 8, 8a, 9, 10, 11, 12, 12a, 12b, 13, 14, 14a-tetradecahydro-picen-3-yl) nicotinic acid ester 98 mg (0.23 mmol) of tingenone (obtained according to Example 3) was dissolved in 10 ml of dry CH ₂ Cl ₂ to give 0.097 ml (3 Eq.) Dry Et ₃ N, 62.12 mg (1.5 eq.) Nicotyl chloride and a catalytic amount of DMAP. The reaction was performed at room temperature, followed by TLC and stirred for 20 minutes. The crude product was purified by preparative silica gel chromatography using CH ₂ Cl ₂ : AcOEt (1: 1) as the mobile phase according to the method described in the previous reaction to give 55 mg (46%) of product C9. It was. The rest was the starting product.

¹ H NMR (300 MHz, CDCl ₃ ) δ 9.37 (1H, dd, J ₁ = 0.9, J ₂ = 2.1 Hz, H _a ); 8.81 (1H, dd, J ₁ = 1.7) , J ₂ = 4.9 Hz, H _d ); 8.43 (1H, dd, J ₁ = 1.9, J ₂ = 8.2 Hz, H _b ); 7.44 (1H, m, H _c ); 7.13 (1H, dd, J ₁ = 1.2, J ₂ = 7.0 Hz, H-6); 6.53 (1H, d, J = 1.3 Hz, H−1); 6.38 ( 1H, d, J = 7.1 Hz, H-7); 2.49 (1H, m, H-20); 2.22 (3H, s, Me-23); 1.54 (3H, s, Me) -25); 1.35 (3H, s, Me-26); 0.99 (3H, s, Me-27); 0.99 (3H, d, J = 6.2 Hz, Me-30); 0 .98 (3H, s, Me-27); 0.97 (3H, d, J = 6.6 Hz, Me-30); 0.95 (3H, s, Me-28). ¹³ C NMR (75 MHz, CDCl ₃ ) δ 11.23 (c, C-23); 14.84 (c, C-30); 19.54 (c, C-27); 21.59 (c, C -26); 28.26 (t, C-15); 29.63 (t, C-12); 31.78 (t, C-19); 32.30 (c, c-28); 69 (t, C-11); 35.23 (t, c-16); 37.91 (s, C-17); 38.81 (c, C-25); 40.23 (s, C- 13); 41.65 (d, c-20); 42.29 (s, C-9); 43.26 (d, C-18); 44.64 (s, C-14); (T, c-22); 117.6 (d, C-7); 123.0 (d, C-1); 123.2 (d, CH-Ar); 125.0 (s, C-Ar) ); 126.3 ( s, c-5); 133.8 (s, C-4); 135.2 (d, C-6); 137.6 (d, CH-Ar); 142.7 (s, C-3) 151.3 (d, N-CH); 153.7 (d, N-CH); 162.8 (s, C-10); 162.9 (s, OCO-Nic); 170.7 (s , C-8); 176.8 (s, C-2); 213.3 (s, C-21). High resolution MS C ₃₄ H ₃₉ NO ₄ Theoretical 525.2879, Found 525.2899.

Example 5
Compound C12: 3,10-dihydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14 , 14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester 1500 g of Salacia root bark is extracted with 2 liters of n-hexane-ethyl ether 1: 1 solvent mixture and the solvent is evaporated After allowing 5 grams of reddish extract to be obtained. This extract was chromatographed on several silica gel columns to give compound C12.

Example 6
Compound C14: 10-dimethylcarbamoyloxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14 , 14a, 14b-Tetradecahydro-picene-2-carboxylic acid methyl ester 300 g of Metenus Amazonica root bark under reflux in a Soxhlet apparatus for 48 hours, 2 liters of n-hexane-ethyl ether 1: 1 solvent mixture After extraction and evaporation of the solvent, 70 g of a reddish solid were obtained. The extract, as eluent n- hexane -CHCl ₃ -MeOH2: 1: chromatographed on Sephadex LH-20 column using a 1 mixture. A total of 41 fractions were obtained, which were combined into several groups by thin layer chromatography (A, B, C, D, E, F and G). Next, these groups were fractionated on a Sephadex LH-20 column with a medium pressure silica gel column and a preparation plate, from which a starting compound called pristimelin was obtained.

In 5 ml of dry CH ₂ Cl ₂ , 65 mg (0.14 mmol) of pristimeline 0.062 ml (3 eq) dry Et ₃ N, 0.02 ml (1.5 eq) N, N-dimethylcarbamoyl chloride and Treated with catalytic amount of DMAP. The reaction was carried out at 0 ° C. under an inert atmosphere, followed by TLC and stirred for 24 hours. Next, 5% dilute hydrochloric acid was added until neutralized. The organic phase was then extracted with CH ₂ Cl ₂ and dried over anhydrous magnesium sulfate. This was filtered and concentrated under reduced pressure. The crude product was purified by preparative column chromatography using n-hexane: AcOEt (2: 3) as the mobile phase to give 36 mg (48%) of product C14. The rest was the starting product.

¹ H NMR (300 MHz, CDCl ₃ ) δ 7.00 (1H, dd, J ₁ =, J ₂ = 7.0 Hz, H-6); 6.46 (1H, d, J = 1.4 Hz, H− 1); 6.29 (1H, d, J = 7.2 Hz, H-7); 3.56 (3H, s, OMe); 3.13 (s, N—CH ₃ ); 3.00 (s) _{, N-CH 3); 2.17} (3H, s, Me-23); 1.46 (3H, s, Me-25); 1.26 (3H, s, Me-26); 1.17 ( 3H, s, Me-30); 1.09 (3H, s, Me-28); 0.54 (3H, s, Me-27). ¹³ C NMR (75 MHz, CDCl ₃ ) δ 10.97 (c, C-23); 18.09 (c, C-27); 21.63 (c, C-26); 28.39 (t, C -15); 29.38 (t, C-12); 29.67 (t, C-21); 30.29 (s, C-17); 30.61 (t, C-19); 34 (c, c-28); 32.40 (c, C-30); 33.45 (t, C-11); 34.49 (t, c-22); 36.15 (s, C- _{16); 36.57 (c, N} -CH 3); 36.58 (c, N-CH 3); 37.99 (c, C-25); 38.99 (s, C-13); 40 .14 (d, c-20); 42.23 (s, C-9); 44.07 (d, C-18); 44.87 (s, C-14); 51.34 (q, OCH ₃ ); 1 17.5 (d, C-7); 122.9 (d, C-1); 126.5 (s, C-4); 133.1 (s, C-5); 134.5 (d, C-6); 143.0 (s, C-3); 153.9 (s, OCON); 162.6 (s, C-10); 170.8 (s, C-2); 178.4 (S, C-29). High resolution MS C ₃₃ H ₄₅ NO ₅ Theoretical 535.3298, Found 535.3294.

Ex vivo assay for human CHOK activity
For ex vivo assays, in E. coli in the presence of methyl [ ¹⁴ C] -choline chloride (50-60 μCi / mmol) in assay buffer (100 mM Tris-HCl pH 8.0, 100 mM MgCl ₂ , 10 mM ATP and 200 μM choline). The expressed recombinant human alpha-1 choline kinase was used. The reaction was performed at 37 ° C. for 30 minutes and stopped with ice-cold trichloroacetic acid having a final concentration of 16%. The sample was washed with diethyl ether saturated with water and lyophilized. This hydrophilic choline derivative was resolved on a thin layer chromatography plate according to the method described [Ramirez, A., Penalva, V., Lucas, L., Lacal, JC Oncogene 21, 937-946 (2002)].

  These assays were performed with compounds C3, C7, C8, C9, C10, C12 and C14 of the present invention and another 8 compounds known in the state of the art (IS 2 117 950). The results are summarized in Table I.

  From the results obtained, it is concluded that the compounds of the present invention significantly and selectively reduce the activity of the choline kinase (ChoK) enzyme in a cell model.

Cell proliferation assay HT-29 cells were seeded in 24-well plates (35H 10 ³ cells / well) and cultured for 24 hours. These cells were then treated with various concentrations of ChoK inhibitor in normal culture medium. After 3 days, each well was aspirated and both fresh media and additional drug were added and the cells were maintained for an additional 3 days. The amount of cells remaining in each well was quantified with a slight modification to the crystal violet method [Gillies, RJ, Didier, N., Denton, M. Anal. Biochem. 159, 109-113 (1986)] [Hernandez- Alcoceba, R., Saniger, L., Campos, J., Nunez, M. C, Khaless, F., Gallo, MA, Espinosa, A., Lacal, JC Oncogene, 15, 2289-2301 (1997)] It was. Briefly, cells were washed with TD buffer and fixed with 1% glutaraldehyde for 15 minutes. After washing again with TD, the cell nuclei were stained with 0.1% crystal violet for at least 30 minutes and washed 3 times with distilled water. The absorbed dye was resuspended in 10% acetic acid and the absorbance was measured with a spectrophotometer at 595 nm. The results obtained are summarized in the form of IC ₅₀ values, ie the concentration of compound required to produce 50% inhibition. This value is determined by iterative adjustment of the curve. Two values were determined for each point on the curve and the experiment was repeated 2 or 3 times to evaluate the average value. Although rare, if these two values differed by more than 50%, a third experiment was performed to determine the true value. IC ₅₀ values are used as indicators of potency to correlate the biological activity of compounds with their chemical structure.

  These assays were performed with compounds C3, C7, C8, C9, C10, C12 and C14 of the present invention and another 8 compounds known in the state of the art (IS 2 117 950). The results are summarized in Table I.

  The table below summarizes the results obtained from the assays performed and presented as examples.

  From the data in Table I, the compounds of the present invention appear to have comparable antiproliferative values against cells derived from cultured tumors.

Claims (71)

Formula (I) in the manufacture of a medicament for the treatment and / or prevention of a disease or condition mediated by ChoK:

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or an unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); Where R is (CH ₂ ) ₂ COOH or (CH ₂ ) ₂ CO ₂ CH ₂ CH ₃ ; or each pair together with the carbon to which they are attached (C═O ) Groups can be formed;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
Join

Means a double bond or a single bond;
Tricyclic structure

Has the following structure:

Where
R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₂₁ , R ₂₂ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl N (R ^VI ) (R ^VII ) amino group (where R ^VI and R ^VII are independently hydrogen or a C ₁ -C ₁₂ alkyl group); OCOR ^VIII group (where R ^VIII is (CH ₂ ) ₂ COOH or (CH ₂ ) ₂ CO ₂ CH ₂ CH ₃ ); or is each pair capable of forming a (C═O) group with the carbon to which they are attached? Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₁₇ is hydrogen or methyl;
R ₁₈ and R _{18 ′} are independently hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (where R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl Yes;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ and R ₂₅ are independently hydrogen, hydroxyl or halogen]
Or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof. A compound of formula (I) is of formula (Ia):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or an unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); Where R is (CH ₂ ) ₂ COOH or (CH ₂ ) ₂ CO ₂ CH ₂ CH ₃ ; or each pair together with the carbon to which they are attached (C═O ) Groups can be formed;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
R ₁₃ , R ₁₄ , R ₁₅ and R ₁₆ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^VI ) (R ^VII ) Amino group (where R ^VI and R ^VII are independently hydrogen or a C ₁ -C ₁₂ alkyl group); OCOR ^VIII group (where R ^VIII is (CH ₂ ) ₂ COOH or (CH ₂ ) ₂ Each pair can form a (C═O) group with the carbon to which they are attached; or CO ₂ CH ₂ CH ₃ ;
R ₁₇ is hydrogen or methyl;
R ₁₈ is hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (wherein R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl;
R ₁₉ is hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ Aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl -O- _(C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 and 3); or trifluoromethyl;
Join

Means a double bond or a single bond]
The use according to claim 1, which is a compound of A compound of formula (Ia) is of formula (Ia ′):

[Where:
R ₅ is a hydroxyl or OCOR group, where R is (CH ₂ ) ₂ COOH or (CH ₂ ) ₂ CO ₂ CH ₂ CH ₃ ;
R ₇ and R ₈ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (here R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or each pair forms a (C═O) group with the carbon to which they are attached. Can do;
R ₁₂ is independently hydrogen or halogen; and
R ₁₉ is hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ Aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl -O- _(C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 to 3); or trifluoromethyl; and,
Join

Means a double bond or a single bond]
The use according to claim 2, which is a compound of The compound of formula (Ia ′) is
3,9-dihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene-2, 10-dione;
Acetic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14 , 14a-tetradecahydro-picen-3-yl ester;
9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14, 14a-tetradecahydro-picen-3-ylpropionic acid ester;
Dodecanoic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13, 14,14a-tetradecahydro-picen-3-yl ester;
-Dimethyl-carbamic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b , 13,14,14a-tetradecahydro-picen-3-yl ester;
Nicotinic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13, 14,14a-tetradecahydro-picen-3-yl ester;
4-Bromo- (9-hydroxy-6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13 , 14,14a-tetradecahydro-picen-3-yl) benzoic acid ester;
14-bromo-3,7,9-trihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH , 9H-picene-2,10-dione;
12-bromo-9-hydroxy-6b, 8a, 11, 12b, 14a-hexamethyl-2, 10-dioxo-2, 6b, 7, 8, 8a, 9, 10, 11, 12, 12a, 12b, 13, 14,14a-tetradecahydro-picen-3-yldimethyl-carbamic acid ester;
4-Bromo- (12-bromo-9-hydroxy-6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a , 12b, 13, 14, 14a-tetradecahydro-picen-3-yl) benzoic acid ester;
12-bromo-3,9-dihydroxy-6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene- 2,10-dione;
3,9,10-trihydroxy-6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-dodecahydro-6bH-picene -2-one;
Succinic acid mono- (10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-3,11-dioxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13 , 14,14a, 14b-tetradecahydro-picen-4-yl) ester; or succinic acid ethyl ester 10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-3,11-dioxo-1, Use according to claim 3, which is 2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b-tetradecahydro-picen-4-yl ester. A compound of formula (Ia) is of formula (Ia ″):

[Where:
R ₇ and R ₈ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (here R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or each pair forms a (C═O) group with the carbon to which they are attached. Can do;
R ₁₅ is hydrogen or halogen;
R ₁₉ is hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ Aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl -O- _(C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 to 3); or trifluoromethyl; and,
Join

Means a double bond or a single bond]
The use according to claim 2, which is a compound of The compound of formula (Ia ″) is
14-bromo-3-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene- 2,10-dione;
4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-tetradeca Hydro-picen-3-yl acetate ester;
4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-tetradeca Hydro-picen-3-ylnicotinic acid ester;
3,10-dihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-dodecahydro-6bH-picene- 2-one; or 3-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 12a, 12b, 13,14,14a-octahydro-6bH, 9H-picene-2,10 -Use according to claim 5, which is dione. A compound of formula (Ia) is of formula (Ia ′ ″):

[Where:
R ₇ is hydrogen, hydroxyl, halogen, substituted or unsubstituted C ₁ -C ₁₂ alkyl, substituted or unsubstituted C ₆ -C ₁₀ aryl, or N (R ′) (R ″) amino group (where R ′ And R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); and
R ₁₉ is substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group (where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; Or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl-O - _(C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 to 3); or trifluoromethyl;
However, when R ₁₉ is hydrogen, R ₇ is not hydrogen]
The use according to claim 2, which is a compound of The compound of formula (Ia ′ ″) is
10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b- Tetradecahydro-picene-2-carboxylic acid methyl ester;
3,10-dihydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester;
2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-10-propionyloxy-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b -Tetradecahydro-picene-2-carboxylic acid methyl ester; or 10-dimethylcarbamoyloxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5 , 6, 6a, 11, 12b, 13, 14, 14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester. A compound of formula (I) is of formula (Ib):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or is unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or C ₁ -C ₁₂ alkyl group) Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₂₁ , R ₂₂ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl Are N (R ^VI ) (R ^VII ) amino groups, where R ^VI and R ^VII are independently hydrogen or C ₁ -C ₁₂ alkyl groups; or each pair is Can form a (C═O) group with the carbon present;
R ₁₇ is hydrogen or methyl;
R ₁₈ is hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (wherein R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl;
R ₁₉ and R ₂₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂₎ alkyl _-O- (C 1 _{-C 12)} alkyl - _{in] n} group (where, n is between 1 and 3); or trifluoromethyl;
Join

Means a double bond or a single bond]
The use according to claim 1, which is a compound of A compound of formula (Ib) is of formula (Ib ′):

[Where:
R ₁₉ and R ₂₀ are independently substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ —C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂₎ alkyl _-O- (C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 and 3); or trifluoromethyl]
The use according to claim 9, which is a compound of   The compound of formula (Ib ′) is 4-nitro- (3-dimethylcarbamoyloxy-5,9-dihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-10-oxo-5,6b, 7, Use according to claim 10, which is 8,8a, 9,10,11,12,12a, 12b, 13,14,14a-tetradecahydro-picen-2-yl) benzoic acid ester. A compound of formula (Ib) is of formula (Ib ″):

[Where:
R ₁₈ is hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (wherein R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl;
R ₁₉ is hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ Aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl -O- _(C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 and 3); or trifluoromethyl;
R ₂₃ is hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^VI ) (R ^VII ) amino group (where R ^VI and R ^VII is a is) independently hydrogen or _C 1 _{-C 12} alkyl radical
The use according to claim 9, which is a compound of The compound of formula (Ib ″) is
7,10,11-trihydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-8-oxo-1,2,3,4,4a, 5,6,6a, 8,12b, 13,14 , 14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester;
9-formyl-10,11-dihydroxy-2,4a, 6a, 12b, 14a-pentamethyl-8-oxo-1,2,3,4,4a, 5,6,6a, 8,12b, 13,14, 14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester; or 11-hydroxy-10- (2-methoxy-ethoxymethoxy) -2,4a, 6a, 9,12b, 14a-hexamethyl-8-oxo -1,2,3,4,4a, 5,6,6a, 8,12b, 13,14,14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester according to claim 12. use. The compound of formula (I) is of formula (Ic):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or is unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or C ₁ -C ₁₂ alkyl group) Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₂₁ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N ( R ^VI ) (R ^VII ) amino group (where R ^VI and R ^VII are independently hydrogen or C ₁ -C ₁₂ alkyl groups); or each pair is bound to the carbon to which they are attached. Together can form a (C═O) group;
R ₁₈ is hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (wherein R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl;
R ₁₉ and R ₂₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂₎ alkyl _-O- (C 1 _{-C 12)} alkyl - _{in] n} group (where, n is between 1 and 3); or trifluoromethyl;
Join

Means a double bond or a single bond]
The use according to claim 1, which is a compound of A compound of formula (Ic) is of formula (Ic ′):

[Where:
R ₁₉ and R ₂₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂₎ alkyl _-O- (C 1 _{-C 12)} alkyl - _{in] n} group (where, n is between 1 and 3); or trifluoromethyl;
Join

Means a double bond or a single bond]
15. Use according to claim 14, wherein the compound is The compound of formula (Ic ′) is
10,11-dihydroxy-2,4a, 6a, 9,14a-pentamethyl-1,4,4a, 5,6,6a, 13,14,14a, 14b-decahydro-2H-picen-3-one; or 10 , 11-dihydroxy-2,4a, 6a, 9,14a-pentamethyl-4a, 5,6,6a, 13,14,14a, 14b-octahydro-4H-picen-3-one. Use of. A compound of formula (Ic) is of formula (Ic ″):

[Where:
R ₁₉ and R ₂₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ —C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); or trifluoromethyl]
15. Use according to claim 14, wherein the compound is   The compound of formula (Ic ″) is 10,11-dihydroxy-2,4a, 6a, 9,14a-pentamethyl-1,2,3,4,4a, 5,6,6a, 13,14,14a, Use according to claim 17, which is 14b-dodecahydro-picene-2-carboxylic acid methyl ester. A compound of formula (I) is of formula (Id):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or is unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or C ₁ -C ₁₂ alkyl group) Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
R ₁₃ , R ₁₅ , R ₂₁ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^VI ) (R ^VII ) An amino group (where R ^VI and R ^VII are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or each pair together with the carbon to which they are attached (C═O ) Groups can be formed;
R ₁₈ is hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (wherein R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ and R ₂₅ are independently hydrogen, hydroxyl or halogen;
Join

Means a double bond or a single bond]
The use according to claim 1, which is a compound of A compound of formula (Id) is of formula (Id ′):

[Where:
R ₅ and R ₆ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (here R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or each pair forms a (C═O) group with the carbon to which they are attached. Can do;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ and R ₂₅ are independently hydrogen, hydroxyl or halogen]
The use according to claim 19, which is a compound of The compound of formula (Id ′) is
1-bromo-9-hydroxy-4,6b, 8a, 11,12b, 14b-hexamethyl-6b, 7,8,8a, 9,11,12,12a, 12b, 14b-decahydro-1H-picene-2, 3,10-trione; or 1-bromo-4,6b, 8a, 11,12b, 14b-hexamethyl-6b, 7,8,8a, 9,11,12,12a, 12b, 14b-decahydro-1H-picene 21. Use according to claim 20, which is -2,3,10-trione. A compound of formula (Id) is of formula (Id ″):

[Where:
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ and R ₂₅ are independently hydrogen, hydroxyl or halogen]
The use according to claim 19, which is a compound of   The compound of formula (Id ″) is 12-bromo-2,4a, 6a, 9,12a, 14a-hexamethyl-10,11-dioxo-1,2,3,4,4a, 5,6,6a, 23. Use according to claim 22, which is 10,11,12,12a, 14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester. A compound of formula (I) is of formula (Ie):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or is unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or C ₁ -C ₁₂ alkyl group) Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently Is a hydrogen or alkyl group C ₁ -C ₁₂ )}; a carbinol group (CH ₂ ) _n —OH (where n is an integer between 1 and 10); or together with methylene Forming a group;
R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₂₁ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N ( R ^VI ) (R ^VII ) amino group (where R ^VI and R ^VII are independently hydrogen or C ₁ -C ₁₂ alkyl groups); or each pair is bound to the carbon to which they are attached. Together can form a (C═O) group;
R ₁₈ and R _{18 ′} are independently hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (where R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl Yes;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ is hydrogen, hydroxyl or halogen;
Join

Means a double bond or a single bond]
The use according to claim 1, which is a compound of A compound of formula (Ie) is of formula (Ie ′):

[Where:
R ₁₈ and R _{18 ′} are independently hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (where R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl Yes;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ is hydrogen, hydroxyl or halogen]
The use according to claim 24, which is a compound of   The compound of formula (Ie ′) is 9-hydroxy-2,4a, 6a, 9,12b-hexamethyl-10,11-dioxo-1,2,3,4,4a, 5,6,6a, 9,10 , 11, 12b, 13, 14, 14a, 14b-Hexadecahydro-picene-2-carboxylic acid methyl ester. A compound of formula (I) is represented by formula (If):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or an unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group, where R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group; Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
R ₁₃ , R ₁₄ , R ₁₅ , R ₂₁ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^VI ) (R ^VII ) an amino group, where R ^VI and R ^VII are independently hydrogen or a C ₁ -C ₁₂ alkyl group; or each pair together with the carbon to which they are attached ( C = O) groups can be formed;
R ₁₈ and R _{18 ′} are independently hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (where R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl Yes;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group (where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C _1- C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl); or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ is independently hydrogen, hydroxyl or halogen;
Join

Means a double bond or a single bond]
The use according to claim 1, which is a compound of A compound of formula (If) is of formula (If ′):

[Where:
R ₁₈ and R _{18 ′} are independently hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (where R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl Yes;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group (where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C _1- C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl); or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ is independently hydrogen, hydroxyl or halogen.
28. The use according to claim 27, wherein   The compound of formula (If ′) is 9-hydroxy-2,4a, 6a, 6b, 9-hexamethyl-10,11-dioxo-1,2,3,4,4a, 5,6,6a, 6b, 8a. , 9, 10, 11, 14, 14a, 14b-Hexadecahydro-picene-2-carboxylic acid methyl ester. Formula (II) in the manufacture of a medicament for the prevention and / or treatment of a disease or condition mediated by ChoK:

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₉ , R ₁₀ , R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₁₇ , R ₁₈ , R ₁₉ And R ₂₀ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (RX ^XV ) (R ^XVI ) amino group (where R or ^XV and R ^XVI are are independently hydrogen or C ₁ -C ₁₂ alkyl group); or each pair, to form them bonded to and carboxyl (C = O) group together with the carbon Can;
R ₇ and R ₈ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^XVII group {where R ^XVII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted _C 6 _{-C 10 aryl; O-C} 1 _{-C 12} alkyl; with or ^{N (R XVIII) (R XIX} ) amino ^{(wherein, R XVIII} and ^{R XIX} are independently hydrogen or _{C 1} Is a —C ₁₂ alkyl group)}; (CH ₂ ) _n —OH carbinol group (where n is an integer between 1 and 10); or together forms a methylene group. ,
R ₂₁ and R ₂₄ are independently substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XX group {where R ^XX is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ —C ₁₀ aryl; or N (R ^XXI ) (R ^XXII ) amino, where R ^XXI and R ^XXII are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂₎ alkyl _-O- (C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 to 3); or trifluoromethyl;
R ₂₂ and R ₂₃ are
When R ₂₄ is para to R ₂₀ , hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XXIII group {where R ^XXIII is hydrogen; hydroxyl; substituted or unsubstituted C _1- C ₁₂ alkyl; substituted or unsubstituted _C 6 _{-C 10} aryl; or ^N (R ^{XXIV) (R XXV)} amino ^{(wherein, R XXIV} and ^{R XXV} are independently hydrogen or _C 1 _{-C 12} alkyl group) Or [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); or is trifluoromethyl? Or, when R ₂₄ is in the meta position relative to R ₂₀ , OR ₂₂ ′ and OR ₂₃ ′, respectively, where R ₂₂ ′ and R ₂₃ ′ are independently hydrogen; Here ^{COR XXVI} group ^{{, R XXVI} is ^hydrogen; unsubstituted _C 1 _{-C 12} alkyl hydroxyl; substituted or unsubstituted _C 1 _{-C 12} alkyl; substituted or unsubstituted _C 6 _{-C 10} aryl; or N (R ^XXVII ) (R ^XXVIII ) amino where R ^XXVII and R ^XXVIII are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl-O- (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); or trifluoromethyl]
Or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof. The compound of formula (II) is of formula (IIa):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₉ , R ₁₀ , R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₁₇ , R ₁₈ , R ₁₉ And R ₂₀ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^XV ) (R ^XVI ) amino group (where R ^XV and R ^XVI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or each pair can form a (C═O) group with the carbon to which they are attached. ;
R ₇ and R ₈ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^XVII group {where R ^XVII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted _C 6 _{-C 10 aryl; O-C} 1 _{-C 12} alkyl; with or ^{N (R XVIII) (R XIX} ) amino ^{(wherein, R XVIII} and ^{R XIX} are independently hydrogen or _{C 1} Is a —C ₁₂ alkyl group)}; (CH ₂ ) _n —OH carbinol group (where n is an integer between 1 and 10); or together forms a methylene group. ;
R ₂₁ and R ₂₄ are independently substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XX group (where R ^XX is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ —C ₁₀ aryl; or N (R ^XXI ) (R ^XXII ) amino, where R ^XXI and R ^XXII are independently hydrogen or a C ₁ -C ₁₂ alkyl group; and [(C ₁ -C ₁₂ ) alkyl. -O- _(C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 and 3); or trifluoromethyl;
R ₂₂ and R ₂₃ are
When R ₂₄ is para to R ₂₀ , hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XXIII group {where R ^XXIII is hydrogen; hydroxyl; substituted or unsubstituted C _1- C ₁₂ alkyl; substituted or unsubstituted _C 6 _{-C 10} aryl; or ^N (R ^{XXIV) (R XXV)} amino ^{(wherein, R XXIV} and ^{R XXV} are independently hydrogen or _C 1 _{-C 12} alkyl group) Or [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); or is trifluoromethyl? Or, when R ₂₄ is in the meta position relative to R ₂₀ , OR ₂₂ ′ and OR ₂₃ ′, respectively, where R ₂₂ ′ and R ₂₃ ′ are independently hydrogen; Here ^{COR XXVI} group ^{{, R XXVI} is ^hydrogen; unsubstituted _C 1 _{-C 12} alkyl hydroxyl; substituted or unsubstituted _C 1 _{-C 12} alkyl; substituted or unsubstituted _C 6 _{-C 10} aryl; or N (R ^XXVII ) (R ^XXVIII ) amino where R ^XXVII and R ^XXVIII are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl-O- (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); or trifluoromethyl]
The use according to claim 30, which is a compound of The compound of formula (IIa) is of formula (IIa ′):

[Where:
R ₁₉ and R ₂₀ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^XV ) (R ^XVI ) amino group (where , R ^XV and R ^XVI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or each pair forms a (C═O) carboxyl group with the carbon to which they are attached. It is possible;
R ₂₁ and R ₂₄ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^XXI ) (R ^XXII ) amino group (where , R ^XXI and R ^XXII are independently hydrogen or a C ₁ -C ₁₂ alkyl group), or each pair together with the carbon to which they are attached (C═O) forms a carboxyl group It is possible;
R ₂₂ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^XXIV ) (R ^XXV ) amino group (where R ^XXIV and R ^XXV are independently hydrogen or a C ₁ -C ₁₂ alkyl group) or each pair together with the carbon to which they are attached (C═O) forms a carboxyl group be able to]
32. Use according to claim 31, wherein the compound is   The compound of formula (IIa ′) is 8- [2- (6,7-dihydroxy-1,5-dimethyl-naphthalen-2-yl) -ethyl] -2,4a-tetramethyl-1,2,3. Use according to claim 32, which is 4,4a, 5,6,7-octahydro-naphthalene-2-carboxylic acid methyl ester.   34. Use according to any one of claims 1 to 33, wherein the ChoK mediated disease or condition to be prevented and / or treated is selected from cancer, preferably breast cancer, lung cancer, colorectal cancer and pancreatic cancer.   34. Use according to any of claims 1-33, wherein the ChoK-mediated disease or condition to be prevented and / or treated is a parasitic disease, preferably a parasitic disease caused by plasmodium or trypanosoma. .   The ChoK-mediated disease or condition to be prevented and / or treated is a parasitic disease, more preferably a parasitic disease caused by a bacterial disease, preferably caused by streptococci. 34. Use according to any one of 33.   34. Use according to any one of claims 1 to 33, wherein the ChoK-mediated disease or condition to be prevented and / or treated is a fungal disease, preferably a fungal disease caused by Candida. Formula (I):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or an unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); Where R is (CH ₂ ) ₂ COOH or (CH ₂ ) ₂ CO ₂ CH ₂ CH ₃ ; or each pair together with the carbon to which they are attached (C═O ) Groups can be formed;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
Join

Means a double bond or a single bond;
Tricyclic structure

Has the following structure:

Where
R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₂₁ , R ₂₂ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl N (R ^VI ) (R ^VII ) amino group (where R ^VI and R ^VII are independently hydrogen or a C ₁ -C ₁₂ alkyl group); OCOR ^VIII group (where R ^VIII is (CH ₂ ) ₂ COOH or (CH ₂ ) ₂ CO ₂ CH ₂ CH ₃ ); or is each pair capable of forming a (C═O) group with the carbon to which they are attached? Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₁₇ is hydrogen or methyl;
R ₁₈ and R _{18 ′} are independently hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (where R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl Yes;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ and R ₂₅ are independently hydrogen, hydroxyl or halogen]
Or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof [wherein
When the tricyclic structure is (a), the compound of formula (I) is
10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b- Tetradecahydro-picene-2-carboxylic acid;
10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b- Tetradecahydro-picene-2-carboxylic acid methyl ester;
3,10-dihydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester;
3-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene-2,10- Dione;
3,9-dihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene-2, 10-dione;
3,7,9-trihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene -2,10-dione;
14-bromo-3,7,9-trihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH , 9H-picene-2,10-dione;
Succinic acid mono- (10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-3,11-dioxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13 , 14, 14a, 14b-tetradecahydro-picen-4-yl) ester;
Succinic acid ethyl ester 10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-3,11-dioxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13, 14,14a, 14b-tetradecahydro-picen-4-yl ester;
Acetic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14 , 14a-tetradecahydro-picen-3-yl ester;
Dodecanoic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13, 14,14a-tetradecahydro-picen-3-yl ester;
Dimethyl-carbamic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-tetradecahydro-picen-3-yl ester;
Nicotinic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13, 14,14a-tetradecahydro-picen-3-yl ester;
3,10-dihydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester;
10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b- Not tetradecahydro-picene-2-carboxylic acid methyl ester,
When the tricyclic structure is (b) and R ₁₉ and R ₂₀ are independently hydrogen or an acyl group,
R ₅ is hydroxyl; or R ₂₁ and R ₂₂ together with the carbon to which they are attached form a C═O group, R ₁₀ is not COOH,
When the tricyclic structure is (c) and R ₁₉ and R ₂₀ are both CH ₃ , R ₁₅ and R ₁₆ together with the carbon to which they are attached do not form a C═O group]. Formula (Ia):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or an unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); Where R is (CH ₂ ) ₂ COOH or (CH ₂ ) ₂ CO ₂ CH ₂ CH ₃ ; or each pair together with the carbon to which they are attached (C═O ) Groups can be formed;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
R ₁₃ , R ₁₄ , R ₁₅ and R ₁₆ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^VI ) (R ^VII ) Amino group (where R ^VI and R ^VII are independently hydrogen or a C ₁ -C ₁₂ alkyl group); OCOR ^VIII group (where R ^VIII is (CH ₂ ) ₂ COOH or (CH ₂ ) ₂ Each pair can form a (C═O) group with the carbon to which they are attached; or CO ₂ CH ₂ CH ₃ ;
R ₁₇ is hydrogen or methyl;
R ₁₈ is hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (wherein R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl;
R ₁₉ is hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ Aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl -O- _(C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 and 3); or trifluoromethyl;
Join

Means a double bond or a single bond]
A compound of claim 38 wherein the compound of formula (Ia) is
10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b- Tetradecahydro-picene-2-carboxylic acid;
10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b- Tetradecahydro-picene-2-carboxylic acid methyl ester;
3,10-dihydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester;
3-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene-2,10- Dione;
3,9-dihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene-2, 10-dione;
3,7,9-trihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene -2,10-dione;
14-bromo-3,7,9-trihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH , 9H-picene-2,10-dione;
Succinic acid mono- (10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-3,11-dioxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13 , 14, 14a, 14b-tetradecahydro-picen-4-yl) ester;
Succinic acid ethyl ester 10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-3,11-dioxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13, 14,14a, 14b-tetradecahydro-picen-4-yl ester;
Acetic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14 , 14a-tetradecahydro-picen-3-yl ester;
Dodecanoic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13, 14,14a-tetradecahydro-picen-3-yl ester;
Dimethyl-carbamic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-tetradecahydro-picen-3-yl ester;
Nicotinic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13, 14,14a-tetradecahydro-picen-3-yl ester;
3,10-dihydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester;
10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b- Not tetradecahydro-picene-2-carboxylic acid methyl ester]. Formula (Ia ′):

[Where:
R ₅ is a hydroxyl or OCOR group, where R is (CH ₂ ) ₂ COOH or (CH ₂ ) ₂ CO ₂ CH ₂ CH ₃ ;
R ₇ and R ₈ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (here R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or each pair forms a (C═O) group with the carbon to which they are attached. Can do;
R ₁₂ is independently hydrogen or halogen; and
R ₁₉ is hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ Aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl -O- _(C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 to 3); or trifluoromethyl; and,
Join

Means a double bond or a single bond]
40. The compound of claim 39, wherein the compound of formula (Ia ′) is
3,9-dihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene-2, 10-dione;
14-bromo-3,7,9-trihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH , 9H-picene-2,10-dione;
Succinic acid mono- (10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-3,11-dioxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13 , 14, 14a, 14b-tetradecahydro-picen-4-yl) ester;
Succinic acid ethyl ester 10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-3,11-dioxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13, 14,14a, 14b-tetradecahydro-picen-4-yl ester;
Acetic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14 , 14a-tetradecahydro-picen-3-yl ester;
Dodecanoic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13, 14,14a-tetradecahydro-picen-3-yl ester;
Dimethyl-carbamic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-tetradecahydro-picen-3-yl ester;
Nicotinic acid 9-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13, Not 14,14a-tetradecahydro-picen-3-yl ester]. 9-hydroxy-4, 6b, 8a, 11, 12b, 14a-hexamethyl-2, 10-dioxo-2, 6b, 7, 8, 8a, 9, 10, 11, 12, 12a, 12b, 13, 14, 14a-tetradecahydro-picen-3-ylpropionic acid ester;
4-Bromo- (9-hydroxy-6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13 , 14,14a-tetradecahydro-picen-3-yl) benzoic acid ester;
12-bromo-3,9-dihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H- Picene-2,10-dione;
12-bromo-9-hydroxy-6b, 8a, 11, 12b, 14a-hexamethyl-2, 10-dioxo-2, 6b, 7, 8, 8a, 9, 10, 11, 12, 12a, 12b, 13, 14,14a-tetradecahydro-picen-3-yldimethyl-carbamic acid ester;
4-Bromo- (12-bromo-9-hydroxy-6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a , 12b, 13,14,14a-tetradecahydro-picen-3-yl) benzoic acid ester; or 3,9,10-trihydroxy-6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a 41, The compound of claim 40, which is 9,10,11,12,12a, 12b, 13,14,14a-dodecahydro-6bH-picen-2-one. Formula (Ia ″):

[Where:
R ₇ and R ₈ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (here R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or each pair forms a (C═O) group with the carbon to which they are attached. Can do;
R ₁₅ is hydrogen or halogen;
R ₁₉ is hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ Aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl -O- _(C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 to 3); or trifluoromethyl; and,
Join

Means a double bond or a single bond]
A compound of claim 39 wherein the compound of formula (Ia ″) is
3-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-dodecahydro-6bH-picene-2- on;
3-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene-2,10- Not dione]. 14-bromo-3-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 11,12,12a, 12b, 13,14,14a-decahydro-6bH, 9H-picene- 2,10-dione;
4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-tetradeca Hydro-picen-3-yl acetate ester;
4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-tetradeca Hydro-picen-3-ylnicotinic acid ester;
3,10-dihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a-dodecahydro-6bH-picene- 2-one; or 3-hydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-7,8,8a, 12a, 12b, 13,14,14a-octahydro-6bH, 9H-picene-2,10 43. The compound of claim 42, which is a dione. Formula (Ia ′ ″):

[Where:
R ₇ is hydrogen, hydroxyl, halogen, substituted or unsubstituted C ₁ -C ₁₂ alkyl, substituted or unsubstituted C ₆ -C ₁₀ aryl, or N (R ′) (R ″) amino group (where R ′ And R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); and
R ₁₉ is substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group (where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; Or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl-O -(C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); or trifluoromethyl]
40. The compound of claim 39, wherein the compound of formula (Ia ′ ″) is
3,10-dihydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester;
10-hydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b- Not tetradecahydro-picene-2-carboxylic acid methyl ester]. 2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-10-propionyloxy-1,2,3,4,4a, 5,6,6a, 11,12b, 13,14,14a, 14b -Tetradecahydro-picene-2-carboxylic acid methyl ester; or 10-dimethylcarbamoyloxy-2,4a, 6a, 9,12b, 14a-hexamethyl-11-oxo-1,2,3,4,4a, 5 45, The compound of claim 44, which is methyl tetradecahydro-picene-2-carboxylic acid methyl ester, 6, 6a, 11, 12b, 13, 14, 14a, 14b. Formula (Ib):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or is unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or C ₁ -C ₁₂ alkyl group) Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₂₁ , R ₂₂ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl Are N (R ^VI ) (R ^VII ) amino groups, where R ^VI and R ^VII are independently hydrogen or C ₁ -C ₁₂ alkyl groups; or each pair is Can form a (C═O) group with the carbon present;
R ₁₇ is hydrogen or methyl;
R ₁₈ is hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (wherein R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl;
R ₁₉ and R ₂₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂₎ alkyl _-O- (C 1 _{-C 12)} alkyl - _{in] n} group (where, n is between 1 and 3); or trifluoromethyl;
Join

Means a double bond or a single bond,
Provided that when R ₁₉ and R ₂₀ are independently hydrogen or an acyl group,
R ₅ is hydroxyl, or R ₂₁ and R ₂₂ together with the carbon to which they are attached form a C═O group, and R ₁₀ is not COOH]
40. The compound of claim 38. Formula (Ib ′):

[Where:
R ₁₉ and R ₂₀ are independently substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ —C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂₎ alkyl _-O- (C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 and 3); or trifluoromethyl]
47. The compound of claim 46.   4-nitro- (3-dimethylcarbamoyloxy-5,9-dihydroxy-4,6b, 8a, 11,12b, 14a-hexamethyl-10-oxo-5,6b, 7,8,8a, 9,10,11 48. The compound of claim 47, which is a benzoate ester, 12,12a, 12b, 13,14,14a-tetradecahydro-picen-2-yl) benzoate. Formula (Ib ″):

[Where:
R ₁₈ is hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (wherein R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl;
R ₁₉ is hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ Aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl -O- _(C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 and 3); or trifluoromethyl;
R ₂₃ is hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^VI ) (R ^VII ) amino group (where R ^VI and R ^VII is a is) independently hydrogen or _C 1 _{-C 12} alkyl radical
47. The compound of claim 46. 7,10,11-trihydroxy-2,4a, 6a, 9,12b, 14a-hexamethyl-8-oxo-1,2,3,4,4a, 5,6,6a, 8,12b, 13,14 , 14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester;
9-formyl-10,11-dihydroxy-2,4a, 6a, 12b, 14a-pentamethyl-8-oxo-1,2,3,4,4a, 5,6,6a, 8,12b, 13,14, 14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester; or 11-hydroxy-10- (2-methoxy-ethoxymethoxy) -2,4a, 6a, 9,12b, 14a-hexamethyl-8-oxo 50. The method of claim 49, which is -1,2,3,4,4a, 5,6,6a, 8,12b, 13,14,14a, 14b-tetradecahydro-picene-2-carboxylic acid methyl ester. Compound. Formula (Ic):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or is unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or C ₁ -C ₁₂ alkyl group) Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₂₁ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N ( R ^VI ) (R ^VII ) amino group (where R ^VI and R ^VII are independently hydrogen or C ₁ -C ₁₂ alkyl groups); or each pair is bound to the carbon to which they are attached. Together can form a (C═O) group;
R ₁₈ is hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (wherein R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl;
R ₁₉ and R ₂₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂₎ alkyl _-O- (C 1 _{-C 12)} alkyl - _{in] n} group (where, n is between 1 and 3); or trifluoromethyl;
Join

Means a double bond or a single bond,
However, when R ₁₉ and R ₂₀ are both CH ₃ , R ₁₅ and R ₁₆ do not form a C═O group with the carbon to which they are attached.]
40. The compound of claim 38. Formula (Ic ′):

[Where:
R ₁₉ and R ₂₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂₎ alkyl _-O- (C 1 _{-C 12)} alkyl - _{in] n} group (where, n is between 1 and 3); or trifluoromethyl;
Join

Means a double bond or a single bond]
52. The compound of claim 51. 10,11-dihydroxy-2,4a, 6a, 9,14a-pentamethyl-1,4,4a, 5,6,6a, 13,14,14a, 14b-decahydro-2H-picen-3-one; or 10 53, 11-dihydroxy-2,4a, 6a, 9,14a-pentamethyl-4a, 5,6,6a, 13,14,14a, 14b-octahydro-4H-picen-3-one. Compound. Formula (Ic ″):

[Where:
R ₁₉ and R ₂₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ —C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); or trifluoromethyl]
52. The compound of claim 51.   10,11-dihydroxy-2,4a, 6a, 9,14a-pentamethyl-1,2,3,4,4a, 5,6,6a, 13,14,14a, 14b-dodecahydro-picene-2-carboxylic acid 55. The compound of claim 54, which is a methyl ester. Formula (Id):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or is unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or C ₁ -C ₁₂ alkyl group) Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
R ₁₃ , R ₁₅ , R ₂₁ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^VI ) (R ^VII ) An amino group (where R ^VI and R ^VII are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or each pair together with the carbon to which they are attached (C═O ) Groups can be formed;
R ₁₈ is hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (wherein R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ and R ₂₅ are independently hydrogen, hydroxyl or halogen;
Join

Means a double bond or a single bond]
40. The compound of claim 38. Formula (Id ′):

[Where:
R ₅ and R ₆ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (here R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or each pair forms a (C═O) group with the carbon to which they are attached. Can do;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ and R ₂₅ are independently hydrogen, hydroxyl or halogen]
57. The compound of claim 56. 1-bromo-9-hydroxy-4,6b, 8a, 11,12b, 14b-hexamethyl-6b, 7,8,8a, 9,11,12,12a, 12b, 14b-decahydro-1H-picene-2, 3,10-trione; or 1-bromo-4,6b, 8a, 11,12b, 14b-hexamethyl-6b, 7,8,8a, 9,11,12,12a, 12b, 14b-decahydro-1H-picene 58. The compound of claim 57, which is -2,3,10-trione. Formula (Id ″):

[Where:
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ and R ₂₅ are independently hydrogen, hydroxyl or halogen]
57. The compound of claim 56.   12-bromo-2,4a, 6a, 9,12a, 14a-hexamethyl-10,11-dioxo-1,2,3,4,4a, 5,6,6a, 10,11,12,12a, 14a, 60. The compound of claim 59, which is 14b-tetradecahydro-picene-2-carboxylic acid methyl ester. Formula (Ie):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or is unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group (where R ′ and R ″ are independently hydrogen or C ₁ -C ₁₂ alkyl group) Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently Is a hydrogen or alkyl group C ₁ -C ₁₂ )}; a carbinol group (CH ₂ ) _n —OH (where n is an integer between 1 and 10); or together with methylene Forming a group;
R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₂₁ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N ( R ^VI ) (R ^VII ) amino group (where R ^VI and R ^VII are independently hydrogen or C ₁ -C ₁₂ alkyl groups); or each pair is bound to the carbon to which they are attached. Together can form a (C═O) group;
R ₁₈ and R _{18 ′} are independently hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (where R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl Yes;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ is hydrogen, hydroxyl or halogen;
Join

Means a double bond or a single bond]
40. The compound of claim 38. Formula (Ie ′):

[Where:
R ₁₈ and R _{18 ′} are independently hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (where R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl Yes;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group {where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ − C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ is hydrogen, hydroxyl or halogen]
62. The compound of claim 61.   9-hydroxy-2,4a, 6a, 9,12b-hexamethyl-10,11-dioxo-1,2,3,4,4a, 5,6,6a, 9,10,11,12b, 13,14, 64. The compound of claim 62, which is 14a, 14b-hexadecahydro-picene-2-carboxylic acid methyl ester. Formula (If):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted Or an unsubstituted C ₆ -C ₁₀ aryl; N (R ′) (R ″) amino group, where R ′ and R ″ are independently hydrogen or a C ₁ -C ₁₂ alkyl group; Or each pair can form a (C═O) group with the carbon to which they are attached;
R ₉ and R ₁₀ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ′ ″ group {where R ′ ″ is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; O—C ₁ -C ₁₂ alkyl; or N (R ^IV ) (R ^V ) amino (where R ^IV and R ^V are independently it is hydrogen or a _C 1 _{-C 12} alkyl _{group)}; (CH 2)} in n -OH carbinol group (where either is n is an integer between 1 and 10); or methylene together Forming a group;
R ₁₃ , R ₁₄ , R ₁₅ , R ₂₁ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^VI ) (R ^VII ) an amino group, where R ^VI and R ^VII are independently hydrogen or a C ₁ -C ₁₂ alkyl group; or each pair together with the carbon to which they are attached ( C = O) groups can be formed;
R ₁₈ and R _{18 ′} are independently hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (where R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl Yes;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group (where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C _1- C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl); or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ is independently hydrogen, hydroxyl or halogen;
Join

Means a double bond or a single bond]
40. The compound of claim 38. Formula (If ′):

[Where:
R ₁₈ and R _{18 ′} are independently hydrogen; hydroxyl; halogen; C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^IX {where R ^IX is hydrogen; hydroxyl; C ₁ -C ₁₂ alkyl; N (R ^X ) (R ^XI ) amino (where R ^X and R ^XI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or C ₁ -C ₁₂ alkoxyl}; or trifluoromethyl Yes;
R ₁₉ , R _{19 ′} , R ₂₀ and R _{20 ′} are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XII group (where R ^XII is hydrogen; hydroxyl; substituted or unsubstituted C _1- C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl); or N (R ^XIII ) (R ^XIV ) amino where R ^XIII and R ^XIV are independently hydrogen or a C ₁ -C ₁₂ alkyl group [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); is trifluoromethyl; Alternatively, each 19-19 ′ or 20-20 ′ pair can form a C═O group with the carbon to which they are attached;
R ₂₄ is independently hydrogen, hydroxyl or halogen.
65. The compound of claim 64.   9-hydroxy-2,4a, 6a, 6b, 9-hexamethyl-10,11-dioxo-1,2,3,4,4a, 5,6,6a, 6b, 8a, 9,10,11,14, 66. The compound of claim 65, which is 14a, 14b-hexadecahydro-picene-2-carboxylic acid methyl ester. Formula (II):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₉ , R ₁₀ , R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₁₇ , R ₁₈ , R ₁₉ And R ₂₀ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (RX ^XV ) (R ^XVI ) amino group (where R or ^XV and R ^XVI are are independently hydrogen or C ₁ -C ₁₂ alkyl group); or each pair, to form them bonded to and carboxyl (C = O) group together with the carbon Can;
R ₇ and R ₈ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^XVII group {where R ^XVII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted _C 6 _{-C 10 aryl; O-C} 1 _{-C 12} alkyl; with or ^{N (R XVIII) (R XIX} ) amino ^{(wherein, R XVIII} and ^{R XIX} are independently hydrogen or _{C 1} Is a —C ₁₂ alkyl group)}; (CH ₂ ) _n —OH carbinol group (where n is an integer between 1 and 10); or together forms a methylene group. ,
R ₂₁ and R ₂₄ are independently substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XX group {where R ^XX is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ —C ₁₀ aryl; or N (R ^XXI ) (R ^XXII ) amino, where R ^XXI and R ^XXII are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂₎ alkyl _-O- (C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 to 3); or trifluoromethyl;
R ₂₂ and R ₂₃ are
When R ₂₄ is para to R ₂₀ , hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XXIII group {where R ^XXIII is hydrogen; hydroxyl; substituted or unsubstituted C _1- C ₁₂ alkyl; substituted or unsubstituted _C 6 _{-C 10} aryl; or ^N (R ^{XXIV) (R XXV)} amino ^{(wherein, R XXIV} and ^{R XXV} are independently hydrogen or _C 1 _{-C 12} alkyl group) Or [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); or is trifluoromethyl? Or, when R ₂₄ is in the meta position relative to R ₂₀ , OR ₂₂ ′ and OR ₂₃ ′, respectively, where R ₂₂ ′ and R ₂₃ ′ are independently hydrogen; Here ^{COR XXVI} group ^{{, R XXVI} is ^hydrogen; unsubstituted _C 1 _{-C 12} alkyl hydroxyl; substituted or unsubstituted _C 1 _{-C 12} alkyl; substituted or unsubstituted _C 6 _{-C 10} aryl; or N (R ^XXVII ) (R ^XXVIII ) amino where R ^XXVII and R ^XXVIII are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl-O- (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); or trifluoromethyl]
Or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof. Formula (IIa):

[Where:
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₉ , R ₁₀ , R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₁₇ , R ₁₈ , R ₁₉ And R ₂₀ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^XV ) (R ^XVI ) amino group (where R ^XV and R ^XVI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or each pair can form a (C═O) group with the carbon to which they are attached. ;
R ₇ and R ₈ are independently hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; C ₆ -C ₁₀ aryl; COR ^XVII group {where R ^XVII is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted _C 6 _{-C 10 aryl; O-C} 1 _{-C 12} alkyl; with or ^{N (R XVIII) (R XIX} ) amino ^{(wherein, R XVIII} and ^{R XIX} are independently hydrogen or _{C 1} Is a —C ₁₂ alkyl group)}; (CH ₂ ) _n —OH carbinol group (where n is an integer between 1 and 10); or together forms a methylene group. ;
R ₂₁ and R ₂₄ are independently substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XX group (where R ^XX is hydrogen; hydroxyl; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ —C ₁₀ aryl; or N (R ^XXI ) (R ^XXII ) amino, where R ^XXI and R ^XXII are independently hydrogen or a C ₁ -C ₁₂ alkyl group; and [(C ₁ -C ₁₂ ) alkyl. -O- _(C 1 _{-C 12)} alkyl _{-] n} group (where, n is between 1 and 3); or trifluoromethyl;
R ₂₂ and R ₂₃ are
When R ₂₄ is para to R ₂₀ , hydrogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; COR ^XXIII group {where R ^XXIII is hydrogen; hydroxyl; substituted or unsubstituted C _1- C ₁₂ alkyl; substituted or unsubstituted _C 6 _{-C 10} aryl; or ^N (R ^{XXIV) (R XXV)} amino ^{(wherein, R XXIV} and ^{R XXV} are independently hydrogen or _C 1 _{-C 12} alkyl group) Or [(C ₁ -C ₁₂ ) alkyl-O— (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); or is trifluoromethyl? Or, when R ₂₄ is in the meta position relative to R ₂₀ , OR ₂₂ ′ and OR ₂₃ ′, respectively, where R ₂₂ ′ and R ₂₃ ′ are independently hydrogen; Here ^{COR XXVI} group ^{{, R XXVI} is ^hydrogen; unsubstituted _C 1 _{-C 12} alkyl hydroxyl; substituted or unsubstituted _C 1 _{-C 12} alkyl; substituted or unsubstituted _C 6 _{-C 10} aryl; or N (R ^XXVII ) (R ^XXVIII ) amino where R ^XXVII and R ^XXVIII are independently hydrogen or a C ₁ -C ₁₂ alkyl group}; [(C ₁ -C ₁₂ ) alkyl-O- (C ₁ -C ₁₂ ) alkyl-] _n group (where n is between 1 and 3); or trifluoromethyl]
68. The compound of claim 67. Formula (IIa ′):

[Where:
R ₁₉ and R ₂₀ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^XV ) (R ^XVI ) amino group (where , R ^XV and R ^XVI are independently hydrogen or a C ₁ -C ₁₂ alkyl group); or each pair forms a (C═O) carboxyl group with the carbon to which they are attached. It is possible;
R ₂₁ and R ₂₄ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^XXI ) (R ^XXII ) amino group (where , R ^XXI and R ^XXII are independently hydrogen or a C ₁ -C ₁₂ alkyl group), or each pair together with the carbon to which they are attached (C═O) forms a carboxyl group It is possible;
R ₂₂ and R ₂₃ are independently hydrogen; hydroxyl; halogen; substituted or unsubstituted C ₁ -C ₁₂ alkyl; substituted or unsubstituted C ₆ -C ₁₀ aryl; N (R ^XXIV ) (R ^XXV ) amino group (where R ^XXIV and R ^XXV are independently hydrogen or a C ₁ -C ₁₂ alkyl group) or each pair together with the carbon to which they are attached (C═O) forms a carboxyl group be able to]
69. The compound of claim 68.   70. A compound of formula (I) or (II) as defined in any one of claims 38 to 69 or a mixture thereof, or a pharmaceutically acceptable salt, derivative, prodrug, solvent thereof for administration to a patient. A pharmaceutical composition comprising a solvate or stereoisomer together with a pharmaceutically acceptable carrier, adjuvant or vehicle.   70. A compound or mixture thereof as defined in any one of claims 38 to 69, or a pharmaceutically acceptable salt, derivative, prodrug, solvate thereof for use in the treatment of a disease or condition mediated by ChoK. Product or stereoisomer.