公开(公告)号：US4916238A

公开(公告)日：1990-04-10

申请号：US283644

申请日：1988-12-13

Applicant: Gary F. Cooper ,  Colin C. Beard ,  David Y. Jackson ,  Douglas L. Wren

Inventor： Gary F. Cooper ,  Colin C. Beard ,  David Y. Jackson ,  Douglas L. Wren

IPC: C07C405/00 ,  C07D309/12 ,  C07F7/18

CPC classification number: C07F7/1856 ,  C07C405/00 ,  C07D309/12 ,  Y02P20/55

Abstract: This invention relates to a novel process for making an allenic prostanoic acid derivative in the form of a single stereoisomer, or a mixture of stereosiomers, represented by the formula (I): ##STR1## wherein R is lower alkyl, R.sup.1 is a protecting group which can be selectively removed in the presence of R.sup.2, R.sup.2 is an acid-labile, base-stable protecting group, X is --(CH.sub.2).sub.2 --, trans --CH.dbd.CH-- or --C.tbd.C--, Y is --C(R.sup.3)(OR.sup.2)CH.sub.2 --, in which --OR.sup.2 is in the .alpha. or .beta. configuration and R.sup.3 is hydrogen or methyl, Z is alkyl, or phenyl, benzyl or phenoxy each optionally substituted on the phenyl ring, and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta..

公开(公告)号：US4804787A

公开(公告)日：1989-02-14

申请号：US785934

申请日：1985-10-09

Applicant: Gary F. Cooper ,  Douglas L. Wren ,  Albert R. Van Horn ,  Tsung-Tee Li ,  Colin C. Beard

Inventor： Gary F. Cooper ,  Douglas L. Wren ,  Albert R. Van Horn ,  Tsung-Tee Li ,  Colin C. Beard

IPC: C07C405/00 ,  C07F7/18 ,  C07C41/00

CPC classification number: C07C405/00 ,  C07C405/0016 ,  C07C405/0025 ,  C07C405/0041 ,  C07F7/1856

Abstract: This invention relates to a process for making an enantiomer or racemic mixture of a compound of the formula ##STR1## wherein R is hydrogen, lower alkyl or a pharmaceutically acceptable, non-toxic salt of a compound wherein R is hydrogen; X is hydrogen, halo, trifluoromethyl, lower alkyl or lower alkoxy, and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta.; novel intermediates useful for preparing these compounds; and processes for making the intermediates.

Abstract translation: 本发明涉及制备下式化合物的对映异构体或外消旋混合物的方法，其中R是氢，其中R是氢的化合物的低级烷基或药学上可接受的无毒盐; X是氢，卤素，三氟甲基，低级烷基或低级烷氧基，波浪线表示α或β构型，条件是当一个波浪线是α时，另一个是β。 用于制备这些化合物的新型中间体; 和制备中间体的方法。

公开(公告)号：US4600785A

公开(公告)日：1986-07-15

申请号：US564386

申请日：1983-12-22

Applicant: Gary F. Cooper ,  Douglas L. Wren ,  Albert R. Van Horn ,  Tsung-Tee Li ,  Colin C. Beard

Inventor： Gary F. Cooper ,  Douglas L. Wren ,  Albert R. Van Horn ,  Tsung-Tee Li ,  Colin C. Beard

IPC: C07B57/00 ,  A61K31/557 ,  A61K31/5575 ,  A61P1/04 ,  C07B31/00 ,  C07B55/00 ,  C07C5/00 ,  C07C67/00 ,  C07C401/00 ,  C07C405/00 ,  C07D309/36 ,  C07F7/08 ,  C07F7/18 ,  C07C177/00

CPC classification number: C07F7/1856 ,  C07C405/00 ,  C07C405/0016 ,  C07C405/0025 ,  C07C405/0041

Abstract: This invention relates to a process for making an enantiomer or racemic mixture of a compound of the formula ##STR1## wherein R is hydrogen, lower alkyl or a pharmaceutically acceptable, non-toxic salt of a compound wherein R is hydrogen; X is hydrogen, halo, trifluoromethyl, lower alkyl or lower alkoxy, and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is a .alpha. the other is .beta.; novel intermediates useful for preparing these compounds; and processes for making the intermediates.

Abstract translation: 本发明涉及制备下式化合物的对映异构体或外消旋混合物的方法，其中R是氢，其中R是氢的化合物的低级烷基或药学上可接受的无毒盐; X是氢，卤素，三氟甲基，低级烷基或低级烷氧基，波浪线表示α或β构型，条件是当一个波浪线是α时，另一个是β; 用于制备这些化合物的新型中间体; 和制备中间体的方法。

公开(公告)号：US4002640A

公开(公告)日：1977-01-11

申请号：US628434

申请日：1975-11-03

Applicant: Colin C. Beard ,  John A. Edwards ,  John H. Fried

Inventor： Colin C. Beard ,  John A. Edwards ,  John H. Fried

IPC: C07C335/38 ,  C07D235/32

CPC classification number: C07C335/38 ,  C07D235/32

Abstract: Benzene ring substituted benzimidazole-2-carbamate derivatives represented by the formula: ##STR1## where R is a lower alkyl group having 1 to 4 carbon atoms; R.sup.1 is -SOR.sup.2, -SO.sub.2 R.sup.2, -SCN, -SR.sup.5, -OR.sup.5 or M'(CH.sub.2).sub.n MR.sup.7 where M and M' are independently O, S, ##STR2## R.sup.7 is lower alkyl having 1 to 4 carbon atoms, or aryl, and n is 1-4; R.sup.2 is lower alkyl having from 1 to 6 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, lower alkenyl or lower alkynyl having 3 to 6 carbon atoms, or aralkyl or aryl; and R.sup.5 is lower alkenyl, lower alkynyl, or aralkyl. The R.sup.1 substitution is at the 5(6)-position.The compounds are useful as pesticides, particularly as anthelmintic and antifungal agents.

Abstract translation: 由下式表示的苯环取代的苯并咪唑-2-氨基甲酸酯衍生物：其中R是具有1至4个碳原子的低级烷基; R1是-SOR2，-SO2R2，-SCN，-SR5，-OR5或M'（CH2）nMR7，其中M和M'独立地为O，S，R7是具有1-4个碳原子的低级烷基，或芳基 ，n为1-4; R2是具有1至6个碳原子的低级烷基，具有3至7个碳原子的环烷基，具有3至6个碳原子的低级链烯基或低级炔基，或芳烷基或芳基; 并且R 5为低级链烯基，低级炔基或芳烷基。 R1取代为5（6）位。

公开(公告)号：US3993769A

公开(公告)日：1976-11-23

申请号：US605704

申请日：1975-08-18

Applicant: Colin C. Beard ,  John A. Edwards ,  John H. Fried

Inventor： Colin C. Beard ,  John A. Edwards ,  John H. Fried

IPC: C07D235/32

Abstract: This application relates to 1,5(6)-disubstituted benzimidazole-2-carbamate derivatives represented by the following formula: ##SPC1##Where R is lower alkyl having 1 to 4 carbon atoms; R.sup.1 is --SOR.sup.2, --SR.sup.5, --OR.sup.5 or M'(CH.sub.2).sub.n MR.sup.7 ; R.sup.2 is lower alkyl having from 1 to 6 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, lower alkenyl or lower alkynyl having 3 to 6 carbon atoms, or aralkyl or aryl; R.sup.5 is lower alkenyl, lower alkynyl or aralkyl; R.sup.7 is lower alkyl having 1 to 4 carbon atoms or aryl;M and M' are independently ##EQU1## n is 1-4; AND R.sup.8 is lower alkyl having 1 to 12 carbon atoms optionally substituted with a --COOR group where R is lower alkyl having 1 to 4 carbon atoms, aryl or aralkyl. The R.sup.1 substitution is at the 5(6)-position.The compounds are useful as pesticides, particularly as anthelmintic and antifungal agents.

Abstract translation: 本申请涉及由下式表示的1,5（6） - 二取代苯并咪唑-2-氨基甲酸酯衍生物：+ q，10，其中R是具有1至4个碳原子的低级烷基; R 1是-SOR 2，-SR 5，-OR 5或M'（CH 2）nMR 7; R2是具有1至6个碳原子的低级烷基，具有3至7个碳原子的环烷基，具有3至6个碳原子的低级链烯基或低级炔基，或芳烷基或芳基; R5是低级烯基，低级炔基或芳烷基; R7是具有1-4个碳原子的低级烷基或芳基; M和M'独立地为O＆amp; O，S，S或S; ＆darr＆＆darr＆OO n为1-4; 且R 8为任选被-COOR基团取代的具有1至12个碳原子的低级烷基，其中R是具有1至4个碳原子的低级烷基，芳基或芳烷基。 R1取代为5（6）位。

公开(公告)号：US3979404A

公开(公告)日：1976-09-07

申请号：US540023

申请日：1975-01-10

Applicant: Colin C. Beard

Inventor： Colin C. Beard

IPC: C07D513/04 ,  C07D417/14

CPC classification number: C07D513/04

Abstract: Novel 2-substituted-1,2,4-thiadiazolo-[2,3-a]-imidazoles of the formula ##SPC1##And the pharmaceutically acceptable salts thereof; and process for their preparation. These 2-substituted-1,2,4-thiadiazolo-[2,3-a]-imidazoles are useful as fungistatic and fungicidal agents.

Abstract translation: 新颖的2-取代-1,2,4-噻二唑并[2,3-a] - 咪唑和其药物接受的盐; 及其制备方法。 这些2-取代-1,2,4-噻二唑并[2,3-a] - 咪唑可用作抑菌和杀真菌剂。

公开(公告)号：US3965113A

公开(公告)日：1976-06-22

申请号：US417968

申请日：1973-11-21

Applicant: Colin C. Beard ,  John A. Edwards ,  John H. Fried

Inventor： Colin C. Beard ,  John A. Edwards ,  John H. Fried

IPC: C07C335/38 ,  C07D235/32

CPC classification number: C07D235/32 ,  C07C335/38

Abstract: Benzene ring substituted benzimidazole-2-carbamate derivatives represented by the formula: ##SPC1##Where R is a lower alkyl group having 1 to 4 carbon atoms; R.sup.1 is --SR.sup.5 or --OR.sup.5 ; and R.sup.5 is aryl. The R.sup.1 substitution is at the 5(6)-position.The compounds are useful as pesticides, particularly as anthelmintic and antifungal agents.

Abstract translation: 由下式表示的苯环取代的苯并咪唑-2-氨基甲酸酯衍生物：

公开(公告)号：US3946031A

公开(公告)日：1976-03-23

申请号：US523765

申请日：1974-11-14

Applicant: Colin C. Beard

Inventor： Colin C. Beard

IPC: C07D235/30 ,  C07D277/60

CPC classification number: C07D235/30

Abstract: Novel 2-substituted-1,2,4-thiadiazolo-[ 2,3-a]-benzimidazoles of the formula ##SPC1##And the pharmaceutically acceptable salts thereof; and process for their preparation. These 2-substituted-1,2,4-thiadiazole-[2,3-a]-benzimidazoles are useful as fungistatic and fungicidal agents.

Abstract translation: 新颖的2-取代-1,2,4-噻二唑并[2,3-a] - 苯并咪唑及其药物接受的盐; 及其制备方法。 这些2-取代-1,2,4-噻二唑 - [2,3-a] - 苯并咪唑可用作抑菌和杀真菌剂。

公开(公告)号：US06215017B1

公开(公告)日：2001-04-10

申请号：US09497537

申请日：2000-02-03

Applicant: Charles A. Dvorak ,  Douglas L. Wren ,  Lawrence E. Fisher ,  Steven D. Axt ,  Eric R. Humphreys ,  Humberto B. Arzeno ,  Colin C. Beard ,  Sam Linh Nguyen ,  Yeun-Kwei Han ,  Christopher R. Roberts ,  Jan P. Lund ,  Paul R. Fatheree

Inventor： Charles A. Dvorak ,  Douglas L. Wren ,  Lawrence E. Fisher ,  Steven D. Axt ,  Eric R. Humphreys ,  Humberto B. Arzeno ,  Colin C. Beard ,  Sam Linh Nguyen ,  Yeun-Kwei Han ,  Christopher R. Roberts ,  Jan P. Lund ,  Paul R. Fatheree

IPC: C07C67743

CPC classification number: C07D473/00 ,  C07D473/18 ,  Y02P20/55

Abstract: Intermediates of Formula (III) wherein Y1 is acyloxy, wherein acyl is of the formula R—C(O)—, wherein R is alkyl of 1-6 carbon atoms, Y2 is aralkyloxy, and Z is benzoyloxy or acyloxy, wherein acyl is as defined above. Intermediates of formula (III) are useful in a novel process for preparing the mono-L-valine ester of 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-1,3-propanediol (ganciclovir). The mono-L-valine ester of ganciclovir and its pharmaceutically acceptable salts are of value as antiviral agents with improved absorption.

Abstract translation: 式（III）的中间体，其中Y1是酰氧基，其中酰基是式RC（O） - ，其中R是1-6个碳原子的烷基，Y2是芳烷氧基，Z是苯甲酰氧基或酰氧基，其中酰基如所定义 式（III）的中间体可用于制备2-（2-氨基-1,6-二氢-6-氧代 - 嘌呤-9-基）甲氧基-1的单-L-缬氨酸酯的新方法 ，3-丙二醇（更昔洛韦）。 更昔洛韦的单-L-缬氨酸酯及其药学上可接受的盐具有改善吸收的抗病毒剂的价值。

公开(公告)号：US5248788A

公开(公告)日：1993-09-28

申请号：US467083

申请日：1990-01-18

Applicant: Gary F. Cooper ,  Colin C. Beard ,  David Y. Jackson ,  Douglas L. Wren

Inventor： Gary F. Cooper ,  Colin C. Beard ,  David Y. Jackson ,  Douglas L. Wren

IPC: C07C405/00 ,  C07D309/12 ,  C07F7/18

CPC classification number: C07C405/00 ,  C07D309/12 ,  C07F7/1856 ,  Y02P20/55

Abstract: This invention relates to a novel process for making an allenic prostanoic acid derivative in the form of a single stereoisomer, or a mixture of stereoisomers, represented by the formula (I): ##STR1## wherein R is lower alkyl, R.sup.1 is a protecting group which can be selectively removed in the presence of R.sup.2, R.sup.2 is an acid-labile, base-stable protecting group, X is --(CH.sub.2).sub.2 --, trans --CH.dbd.CH-- or --C.tbd.C--, Y is --C(R.sup.3)(OR.sup.2)CH.sub.2 --, in which --OR.sup.2 is in the .alpha. or .beta. configuration and R.sup.3 is hydrogen or methyl, Z is alkyl, or phenyl, benzyl or phenoxy each optionally substituted on the phenyl ring, and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta..

Abstract translation: 本发明涉及以式（I）表示的单一立体异构体或立体异构体混合物形式的全氟代前列腺烷酸衍生物的制备方法：其中R为低级烷基，R 1为 在R2存在下可以选择性地除去的保护基，R2是酸不稳定的碱稳定保护基，X是 - （CH 2）2 - ，反-CH = CH-或-C 3 C 是-C（R 3）（OR 2）CH 2 - ，其中-OR 2是α或β构型，R 3是氢或甲基，Z是烷基，或苯基，苄基或苯氧基，其各自任选在苯环上取代， 波浪线表示α或β配置，条件是当一条波浪线为α时，另一条波长为β。