公开(公告)号：US3894025A

公开(公告)日：1975-07-08

申请号：US45319574

申请日：1974-03-21

申请人： UPJOHN CO

发明人： HESTER JR JACKSON B

IPC分类号： A23K1/16 ,  C07D487/04 ,  C07D57/02

CPC分类号： C07D487/04

摘要： 1-piperazino-6-phenyl-4H-s-triazolo(4,3-a)(1,4)benzodiazepines of the formula II:

wherein R is hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, or Beta -hydroxyethyl; wherein R1 is hydrogen or alkyl defined as above; and wherein R2, R3, R4 and R5 are hydrogen, alkyl as defined above, fluoro, chloro, bromo, nitro or trifluoromethyl, are obtained by reacting a compound of the formula I:

wherein R1, R2, R3, R4 and R5 are defined as above, with a piperazine of the formula:

WHEREIN R is defined as above. The compounds of the formula II and their pharmacologically acceptable acid addition salts thereof, have tranquilizing, sedative and anti-depressant effects, and are useful for suppression of anxiety and depression in mammals and birds.

摘要翻译： 具有式II的1-哌嗪基-6-苯基-4H-s-三唑并[4,3-a] [1,4]苯并二氮杂：

公开(公告)号：US3883544A

公开(公告)日：1975-05-13

申请号：US48150474

申请日：1974-06-21

申请人： UPJOHN CO

发明人： HESTER JR JACKSON B ,  GALL MARTIN

IPC分类号： C07D249/08 ,  C07D55/06 ,  C07D57/00

CPC分类号： C07C251/72 ,  C07C243/00

摘要： A process for the production of novel 4-( Alpha -(phenyl)-otoly)-4H-1,2,4-triazoles and 2-(4H-1,2,4-triazol-4-yl)benzophenones from 2-aminobenzophenones by a multistep process. The novel compounds, of this process, are useful for the production of known highly active tranquilizing phenyltriazolobenzodiazepines.

摘要翻译： 制备新的4- [α-（苯基） - 对 - ] -4H-1,2,4-三唑和2-（4H-1,2,4-三唑-4-基） - 二苯甲酮的方法 由2-氨基二苯甲酮通过多步法。 该方法的新化合物可用于生产已知的高活性稳定苯基 - 三唑并苯并二氮杂。

公开(公告)号：US3330835A

公开(公告)日：1967-07-11

申请号：US34349364

申请日：1964-02-10

申请人： UPJOHN CO

发明人： HESTER JR JACKSON B

IPC分类号： C07D209/18 ,  C07D471/06

CPC分类号： C07D471/06 ,  C07D209/18 ,  Y10S514/886

公开(公告)号：US3927016A

公开(公告)日：1975-12-16

申请号：US39551273

申请日：1973-09-10

申请人： UPJOHN CO

发明人： HESTER JR JACKSON B ,  HANZE ARTHUR R

IPC分类号： C07D487/04

摘要： Novel 6-substituted 4H-imidazo(1,2-a)(1,4)benzodiazepines, the intermediate 5-substituted-2-(2-alkynylamino)-3H-1,4benzodiazepines, pharmacologically acceptable acid addition salts thereof, and processes for their production. The compounds of this invention and the pharmacologically acceptable acid addition salts thereof are central nervous system depressants. They are useful as sedatives, hypnotics, tranquilizers, muscle relaxants and anticonvulsants, and also as feed additives for increasing growth rate and feed efficiency of livestock and poultry, milk production in the mammalian species and egg production in avian species.

摘要翻译： 新的6-取代的4H-咪唑并[1,2-a] [1,4]苯并二氮杂，中间体5-取代-2-（2-炔基氨基）-3H-1,4-苯并二氮杂，其药学上可接受的酸加成盐， 和生产过程。 本发明化合物及其药理学上可接受的酸加成盐是中枢神经系统抑制剂。 它们可用作镇静剂，催眠药，镇定剂，肌肉松弛剂和抗惊厥剂，还可用作饲料添加剂，用于提高牲畜和家禽的生长速度和饲料效率，哺乳动物物种中的牛奶生产和禽类种类的产蛋。

公开(公告)号：US3891666A

公开(公告)日：1975-06-24

申请号：US39164773

申请日：1973-08-27

申请人： UPJOHN CO

发明人： HESTER JR JACKSON B

IPC分类号： A23K1/16 ,  A61K31/55 ,  A61P21/02 ,  A61P25/20 ,  C07D249/08 ,  C07D487/04 ,  C07D55/06 ,  C07D57/02

CPC分类号： C07D249/08 ,  C07C251/72 ,  C07D487/04

摘要： Compounds of the formula III:

wherein R is hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, or cycloalkyl of 3 to 7 carbon atoms inclusive; wherein R1 is hydrogen and alkyl defined as above; and wherein R2, R3, R4, and R5 are hydrogen, alkyl defined as above, fluorine, chlorine, bromine, nitro or alkylthio of 1 to 3 carbon atoms inclusive, are prepared by treating a compound of the formula

WHEREIN X is chlorine or bromine, and R, R2, R3, R4, and R5 are defined as above with anhydrous hydrazine or a hydrazine mineral acid salt and a base to give the compound of formula IIIA which is like III with R1 as hydrogen. Alkylation of IIIA (R1 is hydrogen) by conventional method gives the 4-N-alkylderivatives. Compounds II are produced from non-halogenated compounds I by halogenation with N-haloacid amides. The compounds of formula III (including IIIA) are sedative compounds which can be used for tranquilization of mammals.

摘要翻译： 式III化合物：

公开(公告)号：US3886175A

公开(公告)日：1975-05-27

申请号：US44110774

申请日：1974-02-11

申请人： UPJOHN CO

发明人： HESTER JR JACKSON B ,  SZMUSZKOVICZ JACOB

IPC分类号： C07D487/04 ,  C07D57/02 ,  C07D57/04 ,  C07D99/02

CPC分类号： C07D487/04

摘要： IN WHICH N IS DEFINED ABOVE, R7 and R8 are each selected from the group consisting of hydrogen and alkyl as defined above, or

TOGETHER IS PYRROLIDINO OR PIPERIDINO; WHEREIN R2 is selected from the group consisting of hydrogen, alkyl, defined as above, hydroxymethyl,

IN WHICH N'' IS 0 TO 4, INCLUSIVE, AND R is hydrogen or alkyl defined as above or R2 is

IN WHICH N'' IS DEFINED AS ABOVE, AND R7 and R8 are each selected from the group consisting of hydrogen and alkyl as defined above, or

TOGETHER IS PYRROLIDINO, OR PIPERIDINO; WHEREIN R3 and R4 are selected from the group consisting of hydrogen, fluoro, chloro, bromo, nitro, alkyl, defined as above, trifluoromethyl, and alkoxy, in which the carbon moiety is of 1 to 3 carbon atoms, inclusive, are prepared by reacting a thio compound of formula 1

D R A W I N G


wherein R1 is selected from the group consisting of hydrogen, alkyl of 1 to 3 carbons, inclusive,

IN WHICH N IS 1 TO 4, INCLUSIVE, AND R is hydrogen or alkyl defined as above, or R1 is

D R A W I N G
WHEREIN R3 and R4 are defined as above, with formic acid hydrazide or, in two steps, with hydrazine and then triethylorthoformate. The resulting products 11 can be further modified to yield the other compounds corresponding to formula III, as defined above. Compounds of formula III and the pharmacologically acceptable acid addition salts and N-oxides thereof have central nervous system antidepressant activity and can be used in mammals and birds.
Compounds of the formula III:

摘要翻译： 式III化合物：

公开(公告)号：US3347866A

公开(公告)日：1967-10-17

申请号：US46610265

申请日：1965-06-22

申请人： UPJOHN CO

发明人： HESTER JR JACKSON B

IPC分类号： C07D401/04 ,  C07D403/04

CPC分类号： C07D401/04 ,  C07D403/04

公开(公告)号：US3249623A

公开(公告)日：1966-05-03

申请号：US39906964

申请日：1964-09-24

申请人： UPJOHN CO

发明人： HESTER JR JACKSON B

IPC分类号： C07D487/06

CPC分类号： C07D487/06

公开(公告)号：US3214433A

公开(公告)日：1965-10-26

申请号：US35412064

申请日：1964-03-23

申请人： UPJOHN CO

发明人： HESTER JR JACKSON B

IPC分类号： C07D471/04 ,  C07D499/00

CPC分类号： C07D471/04 ,  C07D499/00

公开(公告)号：US3912753A

公开(公告)日：1975-10-14

申请号：US47368474

申请日：1974-05-28

申请人： UPJOHN CO

发明人： HESTER JR JACKSON B

IPC分类号： C07D487/04

CPC分类号： C07D487/04 ,  Y10S514/906

摘要： This invention relates to novel compounds of the formula

WHEREIN Z is selected from the group consisting of O, S and NR'''''' wherein R'''''' is lower alkyl of 1 through 3 carbon atoms; R, R0 and R1 are selected from the group consisting of hydrogen and lower alkyl of 1 through 3 carbon atoms; R'' and R'''' are selected from the group consisting of hydrogen, lower alkyl of 1 through 3 carbon atoms and when taken together with

is a saturated heterocyclic amino radical selected from the group consisting of pyrrolidino, piperidino, morpholino, and 4lower alkylpiperazino wherein lower alkyl is of 1 through 3 carbon atoms, with the proviso that R'' and R'''' cannot be hydrogen when Z is N-R''''''; R2, R3, R4 and R5 are selected from the group consisting of hydrogen, lower alkyl of 1 through 3 carbon atoms, fluorine, chlorine, bromine, nitro, trifluoromethyl, and lower alkylthio of 1 through 3 carbon atoms; and pharmacologically acceptable acid addition salts thereof. The new products of Formula I, including their pharmacologically acceptable acid addition salts, are useful as sedatives, tranquilizers, muscle relaxants, hypnotics, anti-convulsants, anxiolytics in mammals and birds.

摘要翻译： 本发明涉及式WHEREIN Z的新化合物，其选自O，S和N-R“'，其中R”是1至3个碳原子的低级烷基; R，R 0和R 1选自氢和1至3个碳原子的低级烷基; R'和R“选自氢，1至3个碳原子的低级烷基，当与R'一起使用时，N- R”是饱和杂环氨基，其选自吡咯烷子基， 哌啶子基，吗啉代和4-低级烷基哌嗪基，其中低级烷基具有1至3个碳原子，条件是当Z是N-R“时，R'和R”不能是氢; R2，R3，R4和R5选自氢，1至3个碳原子的低级烷基，氟，氯，溴，硝基，三氟甲基和1至3个碳原子的低级烷硫基; 及其药理学上可接受的酸加成盐。