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    NOVEL PROPANE DERIVATIVE
    11.
    发明专利
    NOVEL PROPANE DERIVATIVE 失效

    公开(公告)号：JPH01207276A

    公开(公告)日：1989-08-21

    申请号：JP3193188

    申请日：1988-02-16

    Applicant: KOWA CO

    Inventor： TANABE SOHEI ,  SATO SEIICHI ,  KYOTANI YOSHINORI ,  OTA TOMIO ,  UCHIDA YASUYOSHI

    IPC: C07D295/18 ,  A61K31/47 ,  A61K31/472 ,  A61K31/495 ,  A61K31/55 ,  A61P9/00 ,  C07D217/02 ,  C07D243/08 ,  C07D295/192 ,  C07D295/22 ,  C07D295/26

    Abstract: NEW MATERIAL:A propane derivative of formula I (R is lower alkyl; one of A and B is formula II and the other is formula III, but A and B are different from each other; R1 and R2 are H, lower alkyl, aryl or arylalkyl, and R1 and R2 may be the same or different with or from each other; R3 is lower alkyl, aryl or heterocyclic ring residue which may have a substituent; n is 2 or 3; X is sulfonyl or cabonyl) or an acid-added salt thereof. EXAMPLE:1-(3,4-Dimethoxybenzene sulfonyl)-4-(3-isobutoxy-2- methylbenzylaminopropyl)piperazine. USE:Useful as a medical agent acting on circulatory systems. PREPARATION:For example, the compound of formula I is obtained by reacting a compound of formula IV with a compound of formula V preferably in a solvent in the presence of a base at 0-200 deg.C and subsequently reacting the product with a compound of formula VII at 0-100 deg.C as shown in the reaction formula.

    PRODUCTION OF 3,4-DIHYDRO-3-HYDROXY-8-METHOXY-2H-1-BENZOPYRAN
    12.
    发明专利
    PRODUCTION OF 3,4-DIHYDRO-3-HYDROXY-8-METHOXY-2H-1-BENZOPYRAN 失效

    公开(公告)号：JPS6263582A

    公开(公告)日：1987-03-20

    申请号：JP20356485

    申请日：1985-09-17

    Applicant: KOWA CO ,  DAINIPPON INK & CHEMICALS

    Inventor： TAKAGAKI HIDEJI ,  WATANABE MICHIHIRO ,  NAKANISHI SHIGENORI ,  YAMAZAKI KEIJI ,  ISHIHAMA HIROSHI ,  OTA TOMIO ,  KAWAMURA KIYOSHI

    IPC: C07D311/64

    Abstract: PURPOSE:To industrially and advantageously obtain the titled compound useful as an intermediate for antiallergic agents, drugs for cardiovascular systems etc., by converting 8-methoxy-2H-1-benzopyran into a halohydrin, reacting the resultant product with a base and reducing the resultant epoxidized product. CONSTITUTION:8-Methoxy-2H-1-benzopyran expressed by formula II is converted into a halohydrin of trans-3-halogeno-4-hydroxy-8-methoxy-3,4-dihydro-2H- benzopyranexpressedby formula III, which is then reacted with a base and epoxidized to give 3,4-epoxy-3,4-dihydro-8-methoxy-2H-1-benzopyran expressed by formula IV. The resultant compound expressed by formula IV is further reduced to afford the aimed compound expressed by formula I.

    Novel 1,4-dihydropyridine-3,5-dicarboxylic acid ester derivative
    14.
    发明专利
    Novel 1,4-dihydropyridine-3,5-dicarboxylic acid ester derivative 失效
    新的1,4-二氢吡啶-3,5-二羧酸酯衍生物

    公开(公告)号：JPS6147477A

    公开(公告)日：1986-03-07

    申请号：JP16958884

    申请日：1984-08-14

    Applicant: Kowa Co

    Inventor： SHIMIZU NOBORU ,  ISHIWATARI HIROYUKI ,  OTA TOMIO ,  ISHIHAMA HIROSHI ,  UCHIDA YASUYOSHI

    IPC: C07D401/12 ,  A61K31/44 ,  A61K31/4427 ,  A61K31/455 ,  A61P7/02 ,  A61P9/08 ,  A61P9/10 ,  A61P9/12 ,  C07D211/90 ,  C07D401/14

    CPC classification number: C07D211/90

    Abstract: NEW MATERIAL:The compound of formula I [R is imidazolyl or pyridyl; R1 is H, halogen, nitro or CF3; R2 is lower alkyl; X is CH or N; Z is lower alkylene, group of formula II (B is lower alkylene or 0-lower alkylene), formula III (R4 is H or R2) or formula IV; m is 1-3; n is 1 or 2]. EXAMPLE:2,6-Dimethyl-4-( 3-nitrophenyl )-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl ester 5-{2-{4-[2-(1-imidazolyl)-ethoxy]-benzoyloxy}-ethyl}-ester. USE:A drug effective as a vasodilator, hypotensor, antithrombogenetic agent, antiarteriosclerotic agent, etc. PREPARATION:The compound of formula I can be prepared e.g. by reacting the compound of formula V or its N-protected compound with the compound of formula VI (Hal is halogen), and reacting the resultant compound with the compound of formula RH.

    Abstract translation: 新材料：式I化合物[R是咪唑基或吡啶基; R1是H，卤素，硝基或CF3; R2是低级烷基; X是CH或N; Z是低级亚烷基，式II的基团（B是低级亚烷基或O-低级亚烷基），式III（R4是H或R2）或式IV; m为1-3; n为1或2]。 实施例：2,6-二甲基-4-（3-硝基苯基）-1,4-二氢吡啶-3,5-二羧酸3-乙酯将5- {2- {4- [2-（1-咪唑基） - 乙氧基 - 苯甲酰氧基} - 乙基}酯。 用途：作为血管扩张剂，低血压药，抗血栓形成剂，抗动脉粥样硬化剂等有效的药物。制剂：式Ⅰ化合物可以如 通过使式V化合物或其N-保护的化合物与式VI化合物（Hal是卤素）反应，并使所得化合物与式RH化合物反应。

    15.
    发明专利
    失效

    公开(公告)号：JPH05310744A

    公开(公告)日：1993-11-22

    申请号：JP11286392

    申请日：1992-05-01

    Applicant: KOWA CO

    Inventor： KYOTANI YOSHINORI ,  TAIMA TSUTOMU ,  KURIHARA YUJI ,  KITAMURA TAKAHIRO ,  YAMAGUCHI TAKASHI ,  KAMIYA KAZUHIRO ,  ONOKI KAZUHIRO ,  SATO SEIICHI ,  OTA TOMIO ,  UCHIDA YASUYOSHI

    IPC: A61K31/47 ,  A61K31/4741 ,  A61P9/04 ,  A61P9/06 ,  A61P9/08 ,  C07D491/052

    Abstract: PURPOSE:To provide a new pyrano[2,3-f]quinoline derivative having excel lent antiarrhythmic action, cardiac action, vasodilative action, etc., and useful as a cardiac disease therapeutic agent represented by cardiac failures. CONSTITUTION:The compound of formula 1 (R is lower alkyl; R is H, halogen, OH, lower alkylsulfonyloxy, lower alkanoyloxy, lower alkoxy, azido, amino; R is H, lower alkyl; R is H, lower alkyl, OH, lower alkylamino, pyrrolidinyl or piperazinyl which may have a substituent; when a double bond exists between the 3,4 positions, the substituent R does not exist), e.g. 3acetoxy-6-methyl-3,4,7,8- tetrahydro-2H-pyrano[2,3-f]quinoline. The compound of formula 1-1 among the compounds of formula 1 is obtained by reacting a quinoline compound with an allyl halide compound, thermally subjecting the obtained compound of formula 3 to a Claisen rearrangement, reacting the reaction product with an aliphatic acid anhydride, reacting the obtained compound of formula 5 with a peracid, and subsequently treating the produced epoxy compound of formula 6 with an alkali halide.

    NOVEL SULFONAMIDE COMPOUND
    16.
    发明专利
    NOVEL SULFONAMIDE COMPOUND 失效

    公开(公告)号：JPH01211567A

    公开(公告)日：1989-08-24

    申请号：JP3394988

    申请日：1988-02-18

    Applicant: KOWA CO

    Inventor： TANABE SOHEI ,  SATO SEIICHI ,  KYOTANI YOSHINORI ,  OTA TOMIO ,  UCHIDA YASUYOSHI

    IPC: C07D295/12 ,  A61K31/495 ,  A61P9/00 ,  C07D213/74 ,  C07D213/75 ,  C07D241/04 ,  C07D295/13

    Abstract: NEW MATERIAL:A sulfonamide compound shown by the formula (R1 is lower alkyl, lower alkoxy or halogen; R2 is H, lower alkyl, aryl or arylalkyl; R3 is aryl or arylalkyl; R4 and R4' may be the same or different and H, lower alkyl or lower alkoxy; m is 0-3; n is 1-8) and an acid addition salt thereof. EXAMPLE:1-Diphenylmethyl-4-(3-benzenesulfonylaminopropyl)piperazine. USE:Useful as a drug for cardiovascular system. PREPARATION:For example, a compound shown by formula II is reacted with a compound shown by formula III in a solvent such as methylene chloride or chloroform at -10-+100 deg.C, preferably in the presence of a base such as sodium hydroxide to give a compound shown by formula I wherein R2 is H. Further this compound is reacted with a compound shown by the formula R2'Y (R2' is R2 except H; Y is halogen, alkylsulfonyloxy, etc.) and converted to a compound shown by formula I wherein R2 is except H.

    PRODUCTION OF OPTICALLY ACTIVE COMPOUND
    18.
    发明专利
    PRODUCTION OF OPTICALLY ACTIVE COMPOUND 失效

    公开(公告)号：JPH0222272A

    公开(公告)日：1990-01-25

    申请号：JP17081088

    申请日：1988-07-11

    Applicant: KOWA CO

    Inventor： KAWAMURA KIYOSHI ,  YONEDA MICHIAKI ,  OTA TOMIO

    IPC: C12P17/04 ,  C07D311/04 ,  C07D311/64 ,  C12P17/06 ,  C12R1/85 ,  C12R1/865

    Abstract: PURPOSE:To obtain a 3,8-dihydroxy compound by dividing 3,4-dihydro-8-- protected-hydroxy-3-optically active acyloxy-2H-1-benzopyrane into 3R isomer and 3S isomer and eliminating the acyl group and the OH-protecting group. CONSTITUTION:A compound of formula I (A* is acyl group derived from optically active amino acid; Z is H or protecting group) is divided into 3R isomer and 3S isomer by column chromatography and the acyl group and the OH- protecting group are eliminated from the isomers in an arbitrary order to obtain (3R)- or (3S)-3,8-dihydroxy compound. The compound of formula I can be produced by reacting a compound of formula I wherein OA is OH with a compound of formula II (e.g., L-alanine having protected amino group) or by reacting a compound of formula III with a compound of formula II and reacting the product successively with a peracid and an alkali halide, etc. The obtained 3,8-di-OH compound is useful as an intermediate for a drug for circulatory system.

    PRODUCITON OF 3,4-DIHYDRO-2H-1-BENZOPYRAN-3-OL DERIVATIVE
    19.
    发明专利
    PRODUCITON OF 3,4-DIHYDRO-2H-1-BENZOPYRAN-3-OL DERIVATIVE 失效

    公开(公告)号：JPS61204180A

    公开(公告)日：1986-09-10

    申请号：JP4280885

    申请日：1985-03-06

    Applicant: KOWA CO

    Inventor： KAWAMURA KIYOSHI ,  AKASHI TOSHIHIRO ,  SHIRATO SHOZO ,  ISHIHAMA HIROSHI ,  OTA TOMIO

    IPC: C07D311/58

    Abstract: PURPOSE:To obtain the titled substance useful as pharmaceuticals, etc., easily, without producing by-products, by reacting an o-allylphenol acetyl ester with an epoxidizing agent and cyclizing the obtained specific compound in the presence of an alkali halide, etc. CONSTITUTION:The compound of formula I (R is H, lower alkyl, lower alkoxy, halogen or nitro; n is 1-3; plural R groups may be same or different; R is lower acyl) is used as a raw material, and is made to react in the presence of an alkali halide or a quaternary ammonium halide, in a solvent (preferably acetone, etc.) at 50-120 deg.C under refluxing, and if necessary the product is deacylated to obtain the compound of formula II (R is H or acyl). The amount of the alkali halide or quaternary ammonium halide is preferably 0.1-1 mol- equivalent.

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