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Azacycloalkane Derivatives, Absorption Promoters Containing the Derivatives As the Effective Ingredient and External Preparation Containing the Absorption Promoters

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Azacycloalkane Derivatives, Absorption Promoters Containing the Derivatives As the Effective Ingredient and External Preparation Containing the Absorption Promoters Europaisches Patentamt J European Patent Office © Publication number: 0 241 050 Office europeen des brevets A2 (E) EUROPEAN PATENT APPLICATION (5]) number: 87200183.9 C07D 207/27 C07D Application © int. ci* , 21 1/76 , C07D 223/10 , C07D 263/18 , © Date of filing: 07.02.87 C07D C07D 265/30 , 267/10 , C07D 277/14 , C07D 279/12 , C07D 281/08 , A61K 47/00 , A01N 25/32 © Priority: 08.04.86 JP 79174/86 © Applicant: HISAMITSU PHARMACEUTICAL CO., INC. © Date of publication of application: 408, Tashirodaikan-machi 14.10.87 Bulletin 87/42 Tosu-shi Saga-ken(JP) © Designated Contracting States: © Inventor: Tsuji, Masayoshi AT BE CH DE ES FR GB GR IT LI LU NL SE 992-13, Sonezaki-machi Tosu-shi Saga-ken(JP) Inventor: Inoue, Hisataka 1473-10, Tsufukuhonmachi Kurume-shi, Fukuoka-jen(JP) Inventor: Hachiya, Terumi 1000, Wataze, Chiyoda-machi Kanzaki-gun Saga-ken(JP) Inventor: Nakashima, Mikio 2152, Imaizumi-machi Tosu-shi Saga-ken(JP) Inventor: Saita, Masaru 855-75, Kokura Kiyama-machi Miyaki-gun, Saga-ken(JP) inventor: Shimozono, Yuji 833-1, Tashirodaikan-machi Tosu-shi Saga-ken(JP) Inventor: Nakagawa, Akira 970-11, Fujinoki-machi Tosu-shi Saga-ken(JP) Inventor: Sakai, Michinori IN 1412-13, Naratsu, Jyojima-machi Mizuma-gun Fukuoka-ken(JP) D © Representative: Timmermans, Anthonius C.Th., Ir. et al European Patent Attorneys Octrooibureau IM Zuid P.O. Box 2287 NL-5600 CG Eindhoven(NL) JJ© Azacycloalkane derivatives, absorption promoters containing the derivatives as the effective ingredient and external preparation containing the absorption promoters. .erox Copy Centre 0 241 050 (sy An azacycioalkane derivative useful for promoting the absorption of a medicine, an absorption promoting agent comprising at least one of the azacycioalkane derivatives as the effective ingredient for promoting the absorption and an external preparation containing the absorption promoting agent, the derivative being repre- sented by the following formula B CH„ N-(CH_) -R I 2 , 2 n (I) wherein A is -CH2-or -S-for example, B is sulfur or oxygen, R is -SR" in which R* is an alkyl group or aikylthioalkyl group for example, or -OR" in which R" is as defined above, an alkyl group or substituted amino group, R' is a hydrogen atom, alkyl group or alkyloxy group for example, m is an integer of 0-5 and n is an integer of 1-15. 0 241 050 Azacycioalkane Derivatives, Absorption Promoters containing the Derivatives as the Effective Ingre- dient and External Preparations containing the Absorption Promoters BACKGROUND OF THE INVENTION 1 . Field of the Invention 5 This invention relates to azacycioalkane derivatives which increase medicines in permeability and penetrability and have low irritative actions on live body membranes and low systemic toxicities and also to absorption promoters containing said derivative as the effective ingredient. The compounds, azacycloal- kanes, of this invention are useful in not only medicines but also cosmetics, agricultural chemicals, io insecticides and the like which are other than medicines, as an agent for promoting the permeation of medicines. 2. Prior Art 15 Absorption promoters which have now been known, include organic solvents such as dimethylsulfoxide, dimethylacetamide and pyrrolidone, 1-n-dodecylazacycloheptane-2-one (Azone) and the like described in Japanese Patent Appln. Laid-Open Gazette 52-1035, and N-(2-hydroxyethyl) pyrrolidone and the like described in Japanese Patent Applns. Laid-Open Gazettes 60-13711 and 60-36423. 20 In addition, "Z hur. obshchei Khim. 30, 4108 (1960)" reports 1-(2-propylthioethyl) azacyclopentane-2- one and, however, it neither discloses nor suggests anything about the absorption promoting action exhibited by the compounds of this invention. 25 iProbiems intended to be solved by this invention] There have recently been increasingly interested in the development of pharmaceuticals useful for promoting percutaneous absorption. The reason for this is that when there are administered medicines which are expected to have percutaneously topical or systemic pharmacological actions, the efficacy of the 30 medicines can be endured, the absorption rate thereof can be easily adjusted, the prevention of side effects caused by over-administration of the medicines is possible, effects and the like of metabolism due to first- time passage through a liver as in the case of oral administration and the like are slight thereby to enable the effective use of the medicines, and the medicines may be administered with comparative safety even if they are those which will cause liver troubles and the like when used. Because normal body skins naturally 35 have protective actions on irritations from outward, it is deemed comparatively difficult that medicines are absorbed and permeated through the skins. Even if, thus, medicines are administered in the form of an ointment, cream, gel, lotion or plaster, it is difficult at present to permit medicines to be easily absorbed in such a necessary amount as to achieve the desired medicinal efficacy fully. There are not a few medicines which will be difficulty permeable or penetrable through live body to membranes even if they are administered percutaneously, orally, rectally, palatally, nasally or sublingually. Thus, they have low bioavailability. There have accordingly been sought absorption-promoting agents which fully increase the permeability, penetrability and absorbability of medicines through live body membranes such as skins, exhibit satisfac- tory pharmacological effects when used in a practical concentration, have themselves low topical and is systemic toxicities and are highly useful and safe. The presently known absorption promoters are still not satisfactory enough to enhance the bioavailabil- ity of medicines which are poorly permeable and penetrable through live body membranes, and, further, some of them are irritative to the skins and cause the textures to discolor with remarkable side effects when repeatedly administered. Therefore, they are limited in general application and manner of use, this leaving >o the problem of their practicality unsolved. 3 0 241 050 I tie present inventors made intensive studies in attempts to develop compounds which are highly safe and have more excellent absorption-promoting actions in a practical concentration than those of the heretofore known dimethylsulfoxide and azacycioalkane derivatives and, as the result of their studies, they found that the desired compounds are azacycioalkane derivatives wherein one or two ether bonds, thioether 5 bonds or amino bonds are substituted at the N-position, or azacycioalkane derivatives wherein one methylene chain is substituted by an oxygen atom or a sulfur atom. These desired compounds are fully suitable for the purpose of this invention and are the very compounds of this invention. 70 SUMMARY UP THE INVENTION This invention relates to specific azacycioalkane derivatives and also to absorption-promoting agents containing as the effective ingredient at least one compound selected from said specific azacycioalkane derivatives represented by the following formula (I): 13 B CH2 N-CCH2)n-R <J CD wherein A is -CH2-, -S-or -0-, B is sulfur or oxygen, R is -SR" or -OR* (in which R" is an alkyl group, alkyithioalkyi group, alkyloxyalkyl group, substituted aminoaikyl group, phenyl group, substituted phenyl group, benzoyl group, substituted benzoyl group or heterocyclic group), an alkyl group or substituted amino group, R' is a hydrogen atom, alkyl group, alkyloxy group, acyioxy group, alkylthio group, hydroxyl group, carboxylic group or alkyloxycarbonyl group having 1-12 carbon atoms, m is an integer of 0-5 and n is an 30 integer of 1-15 with the proviso that R does not contain an alkyl group. The symbols R, R' and R" in the general formula (I) are explained hereinafter in more detail. The alkyl group represented by the symbol R is a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl or eicosyl group. 35 The substituted amino group represented by the symbol R is (1) -NR-R1 wherein R' means an alkyl group of 1 to 20 carbon atoms, (2) R1 ^ 2 R wherein RT and Rz each mean an alkyl group of 1 to 20 carbon atoms, (3) a cyclic amino group such as 45 pyrrolidino, piperidino, morpholino, piperadino or -rT^N-R3' 50 wherein R3 means a low alkyl group, low alkyl group substituted by hydroxyl group, benzyl group or a substituted benzyl group(e.g. the substituent includes a low alkyl group, low alcoxy group, hydroxyl group, a halogen atom, trifiuoromethyl group, nitro group, amino group, carboxyl group or an ester thereof) or (4) -NR-R* wherein R* includes phenyl group, benzoyl group, a substituted phenyl group, a substituted benzoyl group (e.g. the substituent includes a low alkyl group, low alcoxy group, hydroxyl group, a halogen atom, 55 trifiuoromethyl group, nitro group, amino group, carboxyl group or an ester thereof) or a heterocyclic group (e.g. pyridyi, thiophene, furan, thiazol, isothiazol, isooxazol, pyrimidine, pyrazol, pyrazine, pyran, pyrrol or pyridazine group). I- 0 241 050 I he alkyl group represented by the symbol R' is an alkyl group having 1 to 20 carbon atoms, an alkyloxy group including methoxy, ethoxy, propoxy, butoxy, pentyioxy, hexyloxy, heptyloxy, octyloxy, nonyioxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy, octadecyloxy, nonadecyloxy
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