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United States Patent (19) 11 Patent Number: 5,952,316 Fujita Et Al

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United States Patent (19) 11 Patent Number: 5,952,316 Fujita Et Al USOO595231.6A United States Patent (19) 11 Patent Number: 5,952,316 Fujita et al. (45) Date of Patent: Sep. 14, 1999 54) 2-AMINO-1,3-PROPANEDIOL COMPOUND 4-6932O 3/1992 Japan . AND IMMUNOSUPPRESSANT 4-173723 6/1992 Japan . 4-224.548 8/1992 Japan . 75 Inventors: Tetsuro Fujita, Muko; Shigeo Sasaki; 5–78294 3/1993 Japan . Masahiko Yoneta, both of Kobe; 92/16236 A2 10/1982 WIPO. Tadashi Mishina, Iruma; Kunitomo OTHER PUBLICATIONS Adachi, Iruma; Kenji Chiba, Iruma, all of Japan Merck Index, No. 460 (2-Amino-2-methyl-1,3-propane diol) p. 73 (1989). 73 Assignees: Yoshitomi Pharmaceutical Industries, Bair et al., J. Med. Chem., “1-Pyrenylmethyl)amino alco Ltd., Osaka; Taito Co., Ltd., Tokyo, hols, a New Class Antitumor DNA Intercalators. Discovery both of Japan and Initial Amine Side Chain Structure-Activity Studies”, 1990, 33, pp. 2385-2393. 21 Appl. No.: 08/911,602 Shetty et al., J. Org. Chem, Nov. 1960, pp. 2057-2059. Derwent Abstract of Japan Patent Unexamined Pub. No. 22 Filed: Aug. 14, 1997 416/1987 published Jan. 1986. Derwent abstract of Japan Patent Unexamined Pub. No. Related U.S. Application Data 192962/1984 published Nov. 1984. Merck Index, 11th Edition, No. 9684 (Tromethamine), pp. 60 Continuation of application No. 08/478,834, Jun. 7, 1995, 1536–1537 (1989). abandoned, which is a division of application No. 08/244, Derwent abstract of Japan Patent Unexamined Pub. 104087/ 942, Jun. 17, 1994, Pat. No. 5,604,229. 1989 published Apr., 1989. 30 Foreign Application Priority Data Rembarz et al., J. Prakt. Chem, 68; Vol. 37 (1-2); pp. 59–63 Oct. 21, 1992 JP Japan .................................... 4-283281 (1968). Jul. 20, 1993 JP Japan .................................... 5-179427 Chemical Abstracts, vol. 85, No. 23, Dec. 6, 1976, Colum bus, Ohio, U.S. abstract No. 177498z, 51) Int. Cl. .......................... A01N 57/00; AO1N 43/60; 2,4-Di-1-aziridinyl-6-amino-s-triazines & Otkrytiya, Izo C07P 401/00; CO7P 211/00 bret., Prom. Obraztsy, Tovarnye Znaki, vol. 53, Nov. 26, 52 U.S. Cl. .......................... 514/114; 514/119, 514/255; 1976, pp. 78-79, Malyugina, L.L. et al., & Chemical 514/357; 514/372; 514/403; 514/477; 514/438: Abstracts 9th coll. Index p. 8505cs, 1,4-Butanediol, 514/459; 514/471; 544/421; 546/210; 546/246; 2-amino-2-(hydroxymethyl). 546/247; 546/334; 548/214; 548/373; 548/516; Merck Index, No. 451 (2-Amino-2-ethyl-1,3-propanediol) 549/75; 549/426; 549/498; 560/11; 560/172; (1989). 564/336; 564/340; 564/342; 564/346; 564/374; Primary Examiner John Kight 564/383; 564/454; 564/123 Assistant Examiner Raymond Covington 58 Field of Search ..................................... 546/210, 246, Attorney, Agent, or Firm Wenderoth, Lind & Ponack, 546/247, 334; 560/172, 11; 556/169; 514/114, LLP. 119,357, 258,372, 403, 427, 438,459, 471; 564/336, 340, 342, 341, 374,383, 57 ABSTRACT 454, 123; 549/75, 426, 498; 548/214, 373.1, 516; 544/421 2-Amino-1,3-propanediol compounds of the formula (I) 56) References Cited (I) U.S. PATENT DOCUMENTS CHOR 3,062,839 11/1962 Shetty et al.......................... 260/347.7 R2R3N-C-CHORS 3,324,043 6/1967 Krum ............... ... 252/.401 R 3,426,042 2/1969 Hostettler et al. ... 260/340.2 3,432,603 3/1969 Zenitz. .................. ... 424/325 3,660,488 5/1972 Cobb ................ ... 260/584 wherein R is an optionally Substituted Straight- or branched 3,928,572 12/1975 Kluepfel et al. ... 424/122 carbon chain, an optionally Substituted aryl, an optionally 4,910,218 3/1990 Bair .................. ... 514/443 substituted cycloalkyl or the like, and R. R. R' and Rare 5,068,247 11/1991 Fujita et al. ............................ 514/440 the same or different and each is a hydrogen, an alkyl, an FOREIGN PATENT DOCUMENTS aralkyl, an acyl or an alkoxycarbonyl, pharmaceutically acceptable Salts thereof and immunosuppressants compris 0044203 A2 1/1982 European Pat. Off.. ing these compounds as active ingredients. O 450 527 A2 10/1991 European Pat. Off.. A-0 410 176 1/1992 European Pat. Off.. The 2-amino-1,3-propanediol compounds of the present 51-54565 5/1976 Japan. 55-21366 2/1982 Japan. invention show immunosuppressive action and are useful for 57-156459 9/1982 Japan. Suppressing rejection in organ or bone marrow tranplanta 58-101108 6/1983 Japan. tion, prevention and treatment of autoimmune diseases or as 63-2904 1/1988 Japan. reagents for use in medicinal and pharmaceutical fields. 63-43140 2/1988 Japan. 4-9309 1/1992 Japan. 8 Claims, No Drawings 5,952,316 1 2 2-AMINO-1,3-PROPANEDIOL COMPOUND An object of the present invention is to provide novel AND IMMUNOSUPPRESSANT 2-amino-1,3-propanediol compounds having Superior immunosuppressive action with leSS Side effects. This application is a continuation of now abandoned application, Ser. No. 08/478,834, filed Jun. 7, 1995, now 5 DISCLOSURE OF THE INVENTION abandoned, which is a divisional of Ser. No. 08/244.942 The present invention relates to filed Jun. 17, 1994, now U.S. Pat. No. 5,604,229. (1) a 2-amino-1,3-propanediol compound of the formula TECHNICAL FIELD (I) The present invention relates to 2-amino-1,3-propanediol 1O CHOR compounds useful as pharmaceuticals, particularly as an 23 5 immunosuppressant. R-R-N-C-CHOR R BACKGROUND ART 15 In recent years, cycloSporin is in use for Suppressing wherein rejection developed in transplanting organs. Inclusive of the R is an optionally Substituted Straight- or branched carbon compounds currently under development, the So-called chain which may have, in the chain, a bond, a hetero immunosuppressants are expected to be useful as therapeutic atom or a group Selected from the group consisting of agents for articular rheumatism and So on. Said cycloSporin, 20 a double bond, a triple bond, Oxygen, Sulfur, Sulfinyl, however, also poses problems of Side effects Such as renal Sulfonyl, -N(R)- where R is hydrogen, alkyl, disorders. aralkyl, acyl or alkoxycarbonyl, carbonyl, optionally Meanwhile, Japanese Patent Unexamined Publication No. Substituted arylene, optionally Substituted 104087/1989 discloses that an immunosuppressive Sub- cycloalkylene, optionally Substituted heteroarylene and stance is obtained from a liquid culture of Isaria Sinclairii an alicycle thereof, and which may be Substituted, at and said substance has been confirmed to be (2S,3R,4R)- the chain end thereof, by a double bond, a triple bond, (E)-2-amino-3,4-dihydroxy-2-hydroxymethyl-14-oxoicosa- optionally Substituted aryl, optionally Substituted 6-enoic acid of the formula cycloalkyl, optionally Substituted heteroaryl or an ali NH2 OH HOHC-C-CH-CH-CH-CH=CH-(CH2) - C-(CH2)5- CH, CO2H OH disclosed in U.S. Pat. No. 3,928,572. In addition, Japanese cycle thereof, an optionally Substituted aryl, an option Patent Unexamined Publication No. 128347/1991 States that ally Substituted cycloalkyl, an optionally Substituted a Series of Said compound has an immunosuppressive action. heteroaryl or an alicycle thereof, and Referring to Merck Index, 11th edition, it is described that 40 R. R. R' and Rare the same or different and each is a 2-amino-2-methyl-1,3-propanediol (Index No. 460), hydrogen, an alkyl, an aralkyl, an acyl or an 2-amino-2-ethyl-1,3-propanediol (Index No. 451) and alkoxycarbonyl, or R' and R may be bonded to form 2-amino-2-hydroxymethyl-1,3-propanediol (also called an alkylene chain which may be Substituted by alkyl, tromethamine, Index No. 9684) can be used as surfactants, aryl or aralkyl, intermediates for. pharmaceuticals, emulsifiers orgas adsor- 5 wherein the optionally substituted straight- or branched bents and that tromethamine is medically usable as an carbon chain may have a Substituent Selected from the group alkalization agent. In Japanese Patent Unexamined Publica- consisting of alkoxy, alkenyloxy, alkynyloxy, aralkyloxy, tion No. 416/1987, a hair dye containing 2-amino-2-(C1-C5 alkylenedioxy, acyl, alkylamino, alkylthio, acylamino, alkyl)-1,3-propanediol is disclosed. U.S. Pat. No. 4,910.218 alkoxycarbonyl, alkoxycarbonylamino, acyloxy, and J. Med. Chem., Vol. 33, 2385-2393 (1990) teach 50 alkylcarbamoyl, haloalkyl, haloalkoxy, nitro, halogen, 2-amino-2-(methyl or ethyl)-1,3-propanediol as an interme- amino, hydroxyimino, hydroxy, carboxy, optionally Substi diate for an antitumor agent. Also, Japanese Patent Unex- tuted aryl, optionally Substituted aryloxy, optionally Substi amined Publication No. 192962/1984 teaches that the afore- tuted cycloalkyl, optionally Substituted heteroaryl and an mentioned 2-amino-2-(C1-C5 alkyl)-1,3-propanediol or alicycle thereof; the aforementioned optionally Substituted 2-amino-1,3-propanediol can be used as a stabilizer for an is arylene, optionally Substituted cycloalkylene, optionally antigen or antibody-Sensitized latex reagent. Moreover, U.S. Pat. No. 3,062,839 teaches 2-methyl- or ethyl-amino-2- Substituted heteroarylene and an alicycle thereof may have (furylmethyl, phenylmethyl or phenylmethyl substituted by a Substituent Selected from the group consisting of alkoxy, lower alkyl, lower alkoxy, chloro, hydroxy or unsubstituted alkenyloxy, alkynyloxy, aralkyloxy, alkylenedioxy, acyl, amine)-1,3-propanediol having a tranquilizer action and J. alkylamino, alkylthio, acylamino, alkoxycarbonyl, Org. Chem., vol. 25, 2057-2059 (1960) teaches 60 alkoxycarbonylamino, acyloxy, alkylcarbamoyl, haloalkyl, 2-methylamino-2-(phenylmethyl or phenylmethyl substi- haloalkoxy, nitro, halogen, amino, hydroxy and carboxy; tuted by 2-methyl, 3-methyl, 4-methyl, 4-methoxy or and the optionally Substituted aryl, optionally Substituted 4-hydroxy)-1,3-propanediol. It is not known, however, that aryloxy, optionally Substituted cycloalkyl, optionally Substi these compounds have immunosuppressive actions Such as tuted heteroaryl and an alicycle thereof may have a Sub suppression of rejection developed in organ transplantation, 65 stituent Selected from the group consisting of alkyl, alkoxy, prevention and treatment of autoimmune diseases and the alkenyloxy, alkynyloxy, aralkyloxy, alkylenedioxy, acyl, like.
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