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    • 2. 发明授权
      US4056537A Process for making pyrano- and thiopyranoindole derivatives 失效
    • Process for making pyrano- and thiopyranoindole derivatives
    • 制备吡喃和噻喃并吲哚衍生物的方法
    • US4056537A
    • 1977-11-01
    • US733829
    • 1976-10-18
    • Christopher A. Demerson , Leslie G. Humber , Andre A. Asselin , Ivo Jirkovsky , Thomas A. Dobson
    • Christopher A. Demerson , Leslie G. Humber , Andre A. Asselin , Ivo Jirkovsky , Thomas A. Dobson
    • C07D491/04 , C07D491/052 , C07D495/04
    • C07D491/04 , C07D495/04
    • Pyranoindole and thiopyranoindole derivatives characterized by having an amino(lower)alkyl radical attached to either or both the 1 and 9 position of a pyrano[3,4-b]indole or thiopyrano[3,4-b]indole nucleus are disclosed. The amino portion of the amino(lower)alkyl radical may be further substituted with one or two lower alkyl groups or incorporated into a heterocyclic amine radical. The derivatives having the amino(lower)alkyl radical only at position 1 are further substituted at position 1 and may be optionally substituted at positions 3, 4, 5, 6, 7, 8, and 9. The derivatives having the amino(lower)alkyl radical only at position 9 possess two substituents at position 1 and may be optionally substituted at position 3, 4, 5, 6, 7, and 8. The derivatives having an amino(lower)alkyl radical at both positions 1 and 9 are further substituted at position 1 and may be optionally substituted at positions 3, 4, 5, 6, 7 and 8. The pyrano- and thiopyranoindole derivatives of this invention are useful antidepressant and antiulcer agents. Methods for the preparation and use of these derivatives are also disclosed.
    • 公开了以吡喃并吲哚和噻喃并吲哚衍生物为特征的具有连接于吡喃并[3,4-b]吲哚或噻喃并[3,4-b]吲哚核的1位和9位的氨基（低级）烷基。 氨基（低级）烷基的氨基部分可进一步被一个或两个低级烷基取代或并入杂环胺基中。 仅在位置1具有氨基（低级）烷基的衍生物在位置1处进一步被取代，并且可以在3,4,5,6,7,8和9位任意被取代。具有氨基（低级） 仅在位置9的烷基基团在位置1具有两个取代基，并且可以任选地在3,4,5,6,7和8位被取代。在位置1和9位置具有氨基（低级）烷基的衍生物进一步 在位置1被取代，并且可以任选地在3,4,5,6,7和8位上被取代。本发明的吡喃和噻喃并吲哚衍生物是有用的抗抑郁剂和抗溃疡剂。 还公开了这些衍生物的制备和使用方法。
    • 基本信息 添加关注 加入工作空间 PDF全文 PDF下载 全文下载 相似专利 双屏查看 权利要求书 说明书全文 Espacenet 法律信息 同族专利 专利引用
    • 3. 发明授权
      US4036856A Cyclopentanone derivatives 失效
    • Cyclopentanone derivatives
    • US4036856A
    • 1977-07-19
    • US741096
    • 1976-11-11
    • Nedumparambil A. Abraham , Jehan F. Bagli , Tibor Bogri
    • Nedumparambil A. Abraham , Jehan F. Bagli , Tibor Bogri
    • C07C405/00 , C07D307/88
    • C07C405/00
    • A process for preparing 11-deoxyprostaglandin E.sub.1, E.sub.2 and E.sub.3 and analogs thereof is realized by treating an appropriate di(lower)alkyl 3-(optionally substituted)-2-formylcyclopropane-1,1-dicarboxylate with an ylid prepared from a Wittig reagent of formula (AlkO).sub.2 POCH.sub.2 CO-(c)-CH.sub.3 in which Alk is an alkyl containing one to three carbon atoms and (c) is either (CH.sub.2).sub.q wherein q is an integer from 1 to 6 or cis CH.sub.2 CH=CH(CH.sub.2).sub.r wherein r is an integer from 0 to 3 to obtain the corresponding compound of formula: ##STR1## in which R.sup.2 is hydrogen, lower alkyl or CH.sub.2 OR.sup.3 wherein R.sup.3 is lower alkanoyl, R.sup.4 is lower alkyl and (c) is as defined herein. The latter compound is reduced with an alkali metal borohydride to yield the corresponding alcohol derivative. Condensation of this alcohol derivative or preferably its corresponding tetrahydropyran-2-yl ether derivative with a triester of formula CH(COOR.sup.6).sub.2 --(a)-(CH.sub.2)pCOOR in which R and R.sup.6 are lower alkyl, (a) is CH.sub.2 CH.sub.2, cis CH=CH or C.tbd.C and p is an integer from 2 to 4, gives the corresponding cyclopentanonetriester of formula ##STR2## in which (a), (c), p, R, R.sup.4 and R.sup.6 are as defined herein, R.sup.5 is hydrogen or tetrahydropyran-2-yl, respectively, and R.sup.7 is hydrogen or lower alkyl; the lactonized form of the cyclopentanonetriester being obtained from said alcohol derivative in which R.sup.2 is CH.sub.2 OR.sup.3 wherein R.sup.3 is lower alkanoyl. In the instance when R.sup.5 is tetrahydropyran-2-yl the cyclopentanonetriester is treated with an acid to give the corresponding compound in which R.sup.5 is hydrogen. The instant compound is then treated with a base under aqueous conditions, followed by optional esterification and acylation to give the desired 11-deoxyprostaglandin derivatives of formula ##STR3## in which (a), (c) and p, are as defined herein, (b) is trans CH=CH, R is hydrogen or lower alkyl, R.sup.1 is hydrogen or lower alkanoyl and R.sup.2 is hydrogen, lower alkyl or CH.sub.2 OR.sup.3 wherein R.sup.3 is hydrogen or lower alkanoyl. The derivatives possess prostaglandin-like biological activity and methods for their use are given.
    • 基本信息 添加关注 加入工作空间 PDF全文 PDF下载 全文下载 相似专利 双屏查看 权利要求书 说明书全文 Espacenet 法律信息 同族专利 专利引用
    • 4. 发明授权
      US4006136A Prostaglandin intermediates 失效
    • Prostaglandin intermediates
    • US4006136A
    • 1977-02-01
    • US489856
    • 1974-07-19
    • Nedumparambil A. Abraham , Jehan F. Bagli , Tibor Bogri
    • Nedumparambil A. Abraham , Jehan F. Bagli , Tibor Bogri
    • C07C45/67 , C07C49/20 , C07C49/203 , C07C405/00 , C07C69/74
    • C07C405/00 , C07C45/673 , C07C49/20 , C07C49/203
    • A process for preparing 11-deoxyprostaglandin E.sub.1, E.sub.2 and E.sub.3 and analogs thereof is realized by treating an appropriate di(lower)alkyl 3-(optionally substituted)-2-formylcyclopropane-1,1-dicarboxylate with an ylid prepared from a Wittig reagent of formula (AlkO).sub.2 PCCH.sub.2 CO-(c)-CH.sub.3 in which Alk is an alkyl containing one to three carbon atoms and (c) is either (CH.sub.2).sub.q wherein q is an integer from 1 to 6 or cis CH.sub.2 CH=CH(CH.sub.2).sub.r wherein r is an integer from 0 to 3 to obtain the corresponding compound of formula: ##STR1## in which R.sup.2 is hydrogen, lower alkyl or CH.sub.2 OR.sup.3 wherein R.sup.3 is lower alkanoyl, R.sup.4 is lower alkyl and (c) is as defined herein. The latter compound is reduced with an alkali metal borehydride to yield the corresponding alcohol derivative. Condensation of this alcohol derivative or preferably its corresponding tetrahydropyran-2-yl ether derivative with a triester of formula CH(COOR.sup.6).sub.2 -(a)-(CH.sub.2)pCOOR in which R and R.sup.6 are lower alkyl, (a) is CH.sub.2 CH.sub.2, cis CH=CH or CaC and p is an integer from 2 to 4, gives the corresponding cyclopentanonetriester of formula ##STR2## in which (a), (c), p, R, R.sup.4 and R.sup.6 are as defined herein, R.sup.5 is hydrogen or tetrahydropyran-2-yl, respectively, and R.sup.7 is hydrogen or lower alkyl; the lactonized form of the cyclopentanone-triester being obtained from said alcohol derivative in which R.sup.2 is CH.sub.2 OR.sup.3 wherein R.sup.3 is lower alkanoyl. In the instance when R.sup.5 is tetrahydropyran-2-yl the cyclopentanonetriester is treated with an acid to give the corresponding compound in which R.sup.5 is hydrogen. The instant compound is then treated with a base under aqueous conditions, followed by optional esterification and acylation to give the desired 11-deoxy-prostaglandin derivatives of the formula ##STR3## in which (a), (c) and p, are as defined herein, (b) is trans CH=CH, R is hydrogen or lower alkyl, R.sup.1 is hydrogen or lower alkanoyl and R.sup.2 is hydrogen, lower alkyl or CH.sub.2 OR.sup.3 wherein R.sup.3 is hydrogen or lower alkanoyl. The derivatives possess prostaglandin-like biological activity and methods for their use are given.
    • 基本信息 添加关注 加入工作空间 PDF全文 PDF下载 全文下载 相似专利 双屏查看 权利要求书 说明书全文 Espacenet 法律信息 同族专利 专利引用
    • 5. 发明授权
      US4003913A Pyrano- and thiopyranoindole derivatives, compositions and methods of use 失效
    • Pyrano- and thiopyranoindole derivatives, compositions and methods of use
    • 吡喃和噻喃并吲哚衍生物，组合物和使用方法
    • US4003913A
    • 1977-01-18
    • US555906
    • 1975-03-05
    • Christopher A. Demerson , Lesie G. Humber , Andre A. Asselin , Ivo Jirkovsky , Thomas A. Dobson
    • Christopher A. Demerson , Lesie G. Humber , Andre A. Asselin , Ivo Jirkovsky , Thomas A. Dobson
    • C07D209/08 , C07D495/04
    • C07D209/08 , Y10S514/925
    • Pyranoindole and thiopyranoindole derivatives characterized by having an amino(lower)alkyl radical attached to either or both the 1 and 9 position of a pyrano[3,4-b]indole or thiopyrano[3,4-b]indole nucleus or having said radical attached to the 1 position of a pyrano[4,3-b]indole or thiopyrano[4,3-b]indole nucleus are disclosed. The amino portion of the amino(lower)alkyl radical may be further substituted with one or two lower alkyl groups or incorporated into a heterocyclic amine radical. The derivatives having the amino(lower)alkyl radical only at position 1 are further substituted at position 1 and may be optionally substituted at positions 3,4,5,6,7,8, and 9. The pyrano[3,4-b]indole or thiopyrano[3,4-b]indole derivatives having the amino(lower)alkyl radical only at position 9 possess two substituents at position 1 and may be optionally substituted at position 3,4,5,6,7, and 8; the derivatives having an amino(lower)alkyl radical at both positions 1 and 9 are further substituted at position 1 and may be optionally substituted at positions 3,4,5,6,7 and 8. The pyrano-and thiopyranoindole derivatives of this invention are useful antidepressant and antiulcer agents. Methods for the preparation and use of these derivatives are also disclosed.
    • 吡喃并吲哚和噻喃并吲哚衍生物，其特征在于具有连接于吡喃并[3,4-b]吲哚或噻喃并[3,4-b]吲哚核的1位和9位的氨基（低级）烷基，或具有所述基团 公开了连接于吡喃并[4,3-b]吲哚或噻喃并[4,3-b]吲哚核的1位的化合物。 氨基（低级）烷基的氨基部分可进一步被一个或两个低级烷基取代或并入杂环胺基中。 仅在位置1具有氨基（低级）烷基的衍生物在位置1处进一步被取代，并且可以在3,4,5,6,7,8和9位任意被取代。吡喃并[3,4-b ]吲哚或噻喃并[3,4-b]吲哚衍生物，其仅在位置9具有氨基（低级）烷基，在位置1具有两个取代基，并且可以任选在3,4,5,6,7和8位上被取代 ; 具有位置1和9位置上的氨基（低级）烷基的衍生物在位置1处进一步被取代，并且可以在3,4,5,6,7和8位任意被取代。本发明的吡喃和噻喃并吲哚衍生物 是有用的抗抑郁药和抗溃疡剂。 还公开了这些衍生物的制备和使用方法。
    • 基本信息 添加关注 加入工作空间 PDF全文 PDF下载 全文下载 相似专利 双屏查看 权利要求书 说明书全文 Espacenet 法律信息 同族专利 专利引用
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