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KS-506 Compounds and Process for the Production Thereof

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KS-506 Compounds and Process for the Production Thereof Europaisches Patentamt 0 335 386 European Patent Office CO Publication number: A1 Office europeen des brevets EUROPEAN PATENT APPLICATION 153/07 © Application number: 89105611.1 int. ci": C07C 149/36 , C07C , C07C 69/90 , A61K 35/74 , (§) Date of 30.03.89 filing: C12P 1/04 , C12P 7/00 , C12P 11/00 The applicant has filed a statement in Applicant: KYOWA HAKKO KOGYO CO., LTD. accordance with Rule 28 (4) EPC (issue of a 6-1, Ohtemachi 1-chome sample only to an expert). Accession number(s) Chiyoda-ku Tokyo 100(JP) of the deposit(s): FERM BP-1776 Inventor: Kuroda, Kazutoshi Coopo Terada 202 1-2-14, Asahi-cho Priority: 31.03.88 JP 80084/88 Machida-Shi Tokyo(JP) 31.03.88 JP 80085/88 Inventor: Kase, Hiroshi 30.08.88 JP 216044/88 3-35-18, Maehara-cho Koganei-Shi Tokyo(JP) Date of publication of application: Inventor: Ando, Katsuhiko 04.10.89 Bulletin 89/40 Kyowa Apartment B-2 3-9-11, Naka-machi Machida-Shi Tokyo(JP) Designated Contracting States: Inventor: Kawamoto, Isao DE FR GB IT 1-21-2, Fujimino Hiratsuka-shi Kanagawa-ken(JP) Inventor: Yasuzawa, Toru 832, Tokaichiba-cho Midori-ku Yokohama-shi Kanagawa-ken(JP) Inventor: Sano, Hiroshi 7-19-16, Tamagawagakuen Machida-shi Tokyo(JP) Inventor: Goto, Joji 2-13-3, Naruse Machida-shi Tokyo(JP) Inventor: Yamada, Koji 1-12-2, Asahi-machi Machida-shi Tokyo(JP) Representative: Casalonga, Axel et al BUREAU D.A. CASALONGA - JOSSE Morassistrasse 8 D-8000 Munich 5(DE) KS-506 compounds and process for the production thereof. Q.© KS-506a, KS-506x and KS-506g having an activity to inhibit cyclic nucleotide phosphodiesterase and KS- UJ506m and KS-506h having an activity to inhibit histamine release are produced by cuituring a microorganism belonging to the genus Mortierella. Xerox Copy Centre EP 0 335 386 A1 KS-506 COMPOUNDS AND PROCESS FOR THE PRODUCTION THEREOF Background of the Invention The present invention relates to novel physiologically active substances, herein identified as KS-506a, KS-5G6x, KS-506g, KS-506m and KS-506h, and a process for the production thereof. 5 KS-506a, KS-506x and KS-506g have an activity to inhibit cyclic nucleotide phosphodiesterase and are useful as Pharmaceuticals such as bronchodilators, cardiotonics, vasodilators, hormone secretomotor agents and antiallergic agents and also as reagents for the research of cyclic adenosine-3 ,5 -monophosphoric acid (hereinafter referred to as cAMP) and cyclic guanosine-3',5'-monophosphoric acid (hereinafter referred to as cGMP). iq KS-506m and KS-506h have an activity to inhibit histamine release and are useful as Pharmaceuticals such as antiallergic agents and antiinflammatory agents. cAMP and cGMP are substances which play an important role as a second messenger in the signal transduction system in a living body. It is generally considered that they are involved in contraction of smooth muscles of bronchus and blood vessel, contraction of cardiac muscle, secretion of hormone, release 75 of transmitters such as histamine, platelet aggregation, cell growth and differentiation, and the like. Cyclic nucleotide phosphodiesterase (hereinafter referred to as PDE) is an enzyme which hydrolyzes cAMP and cGMP to form adenosine-5'-monophosphoric acid and guanosine-5'-monophosphoric acid, respectively. It has been known that substances inhibiting the enzyme raise the concentration of cAMP and cGMP in a living body and as a result exhibit a bronchodilator action, a smooth muscle-relaxing action, a cardiotonic 20 action, a hormone secretomotor action, an action of inhibiting the release of transmitters such as histamine which is one of the causative substances of allergy, an antithrombotic action, etc. Heretofore, the following substances have been known as substances which are produced by microor- ganisms and have a PDE-inhibiting action: 25 (1)Terferol J. Antibiot. 37, 6-9(1984) 30 HO 35 40 (2) Griseolic acid J. Antibiot. 38, 823(1985) 45 50 EP 0 335 386 A1 10 75 (3) Reticurol J. Antibiot. 28, 558 -560 (1975) 20 HO CH. CH3° 25 OH 0 30 (4) PDE-I, II Agr. Biol. Chem. 42, 1331 - 1336 (12978) 35 R^ ^N OCH. HO 40 OCH. PDE-I : R = -NH2 PDE-II: R = -CH3 45 (5) KS-619-1 J.Antibiot. 40, 1104 - 1110 (1987) 50 55 EP 0 335 386 A1 COOH HO. OH 0 OH 10 (6) K-259-2 75 J. Antibiot. 40, 1092-1100 (1987) 20 OH 0 OH 25 (7) Genistein Agr. Biol. Chem. 51 , 3003 - 3009 "(1987) . 35 OH O Substances (1) to (5), substance (6) and substance (7) are produced by actinomycetes of the genus Streptomyces, the Micromonospora and the genus Streptosporangium, respectively. Further, TPI 40 genus having the following structure has been known as a substance which is produced by a fungus and inhibits PDE: OR OH 45 COOH CH2(CH2)5CH CH2(CH2)5CH3 so TPI-1 : R = 0-D-glucopyranosyl TPI-2 : R = ;8-D-galactopyranosyl TPI-3 : R = 6'-O-acetyl-/S-D-glucopyranosyl 6'-O-acetyl-/S-D-galactopyranosyl 55 TPi-4 : R = TPI-5: R = H (Japanese Published Unexamined Patent Application No. 215551/1987) Furthermore, KS-503c which is produced by a microorganism belonging to the genus Hormonema and EP 0 335 386 A1 has a PDE-inhibiting activity has been disclosed in Japanese Patent Application No. 39225/1988. As chemically synthesized substances, there have been known theophyliine, papaverine and the like used as Pharmaceuticals such as cardiotonics and vasodilators. As compounds which are produced by microorganisms and have an activity to inhibit histamine release, Patent 5 there have been known K-252 (U.S.P. 4,555,402) and KT 5556 (Japanese Published Unexamined Application No. 176531/1986) produced by microorganisms belonging to the genus Nocardiopsis. Summary of the Invention 70 The present invention provides novel compounds KS-506a, KS-506x, KS-506g, KS-506m and KS-506h, which are herein generically referred to as KS-506 compounds. KS-506a, KS-506x and KS-506g have an activity to inhibit PDE and are useful as Pharmaceuticals such as bronchodilators, cardiotonics, vasodilators, hormone secretomotor agents and antiallergic agents and also 75 as reagents for the research of cAMP and cGMP. KS-506m and KS-506h have an activity to inhibit histamine release and are useful as Pharmaceuticals such as antiallergic agents and antiinflammatory agents. KS-506 compounds can be prepared by culturing microorganisms belonging to the genus Mortierella and being capable of producing the compounds in a culture medium. 20 Detailed Description of the Invention KS-506a, KS-506x and KS-506g are represented by the following general formula: 25 ?=3? 0 CH, X -s— s — H3C CH. CH3 H3C *K 30 OH HO H3C CH3 H3C CH. CH, CH. OH OH 35 0 0 II It KS-506a : X=-C- , Y=-C- 0 KS-506x X=-C- Y= single bond 40 : , KS-506g : X= single bond, Y= single bond KS-506m and KS-506h are represented by the following general formula: 45 50 HO CH3 H3C ■H 55 KS-506m : R = -SCH2CH2CCH3 EP 0 335 386 A1 KS-506h : R =-OCH3 The physicochemical properties of KS-506a, KS-506x, KS-506g, KS-506m and KS-506h are as follows. 5 1. KS-506a (1 ) Appearance: white powder (2) Molecular formula: C4.0H+2O12S2 (3) Infrared absorption spectrum: (the solution method, in CHCI3) 70 crrr-: 3630, 3400, 1707, 1655, 1615, 1587, 1460, 1425, 1310, 1167, 1104 (4) 'H-NMR spectrum: (400MHz, in CDCI3) 5(ppm): 11.36(2H, s), 5.32(2H, br s), 5.18(2H, br s), 2.49(6H, s), 2.32(6H, s), 2.17(6H, s), 2.14(61-1, s), 2.12- (6H, s), 2.01 (6H, s) (5) 13C-NMR spectrum: (100MHz, in CDCI3) 15 S(ppm): 188.6, 170.6, 161.1, 157.8, 154.6, 143.7, 138.7, 133.5, 124.1, 121.2, 115.5, 114.9, 107.6, 104.6, 19.1, 16.7,12.0,11.9,9.8,8.0 (6) Mass spectrum: (SIMS) m/z:779(M +1)* (7) Color reaction: positive in each of iodine, 50% suifuric acid, anisaldehyde and nitroprusside 20 reactions; and negative in each of anilinephthalic acid, ninhydrin and Rydon-Smith reactions (8) Solubility: soluble in methanol, ethanol, acetone, ethyl acetate, acetonitrile, dimethylsulfoxide and chloroform; and insoluble in hexane and water 25 2. KS-506x (1 ) Appearance: white powder (2) Molecular formula: C39H4.2O11S2 (3) Infrared absorption spectrum: (KBr tablet) 30 cm"': 3470, 1645, 1613, 1588, 1452, 1280, 1214, 1166, 1100, 790 (4) 1 H-NMR spectrum: (400MHz, in CD3OD) 5(ppm): 2.61 (3H, br s), 2.49(3H, br s), 2.16 (6H, s), 2.12(31-1, s), 2.084(3H, s), 2.080(3H, s), 2.03(3H, s), 1.89- (3H, s), 2.1-1 .8(9H) (5) 13C-NMR spectrum: (100MHz, in CD3OD) 35 5(ppm): 194.2, 172.0, 171.8, 162.3, 161.8, 160.7, 160.4, 157.1, 157.0, 150.9, 145.0, 141.5, 139.3, 139.1, 133.4, 124.9, 123.6, 123.2, 118.5, 117.8(2), 117.2, 117.0, 109.7, 109.5, 105.6, 104.4, 19.8, 19.1, 18.8, 16.6, 13.2, 12.51, 12.49, 12.3, 10.7, 10.2, 8.72, 8.66 (6) Mass spectrum: (SIMS) m/z:751(M +1)* 40 (7) Color reaction: positive in each of iodine, 50% suifuric acid, anisaldehyde and nitroprusside reactions; and negative in each of anilinephthalic acid, ninhydrin and Rydon-Smith reactions (8) Solubility: soluble in methanol, ethanol, acetone, ethyl acetate, acetonitrile, dimethylsulfoxide and chloroform; and insoluble in hexane and water 45 3.
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