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1. 发明授权

US4870104A 11-haloprostane derivatives, processes for their preparation and their use as medicinal agents 失效
标题翻译： 11-卤代前驱烷衍生物，其制备方法及其作为药物的用途
公开(公告)号：US4870104A
公开(公告)日：1989-09-26
申请号：US929310
申请日：1986-11-12
申请人： Helmut Vorbruggen , Norbert Schwarz , Olaf Loge , Claus-Steffen Sturzebecher , Walter Elger
发明人： Helmut Vorbruggen , Norbert Schwarz , Olaf Loge , Claus-Steffen Sturzebecher , Walter Elger
IPC分类号： C07D317/16 , A61K31/557 , A61K31/5575 , A61P43/00 , C07C67/00 , C07C401/00 , C07C405/00 , C07D263/00 , C07D263/14 , C07D271/00 , C07D271/06 , C07D317/20 , C07D319/12 , C07D321/00 , C07D493/00 , C07D493/08
CPC分类号： C07C405/0016 , C07C405/00 , C07C405/0041 , C07D317/20
摘要： 11-Haloprostane derivatives of general formula I ##STR1## wherein X is F, Cl or Br,R.sub.1 is the residue CH.sub.2 OH or ##STR2## wherein R.sub.2 means a hydrogen atom, an alkyl, cycloalkyl, aryl, phenacyl or heterocyclic residue,A is a --CH.sub.2 --CH.sub.2 -- or cis-CH.dbd.CH-group,B is a --CH.sub.2 --CH.sub.2 -- or trans-CH.dbd.CH-- or a --C.tbd.C-group,W is an ethylenedioxymethylene group or a hydroxymethylene group,D and E together mean a direct bond orD is a C.sub.1-10 -alkylene group,E is an oxygen or sulfur atom, a direct bond, a --C.tbd.C-bond or a --CR.sub.6 .dbd.CR.sub.7 -group with R.sub.6 and R.sub.7 meaning a hydrogen atom, a chlorine atom or an alkyl group,R.sub.4 is a hydroxy group,R.sub.5 is a hydrogen atom, an alkyl, a cycloalkyl, an aryl or a heterocyclic group, andthe salts thereof with physiologically compatible bases, processes for their preparation, and use thereof as agents inhibiting gastric acid secretion.
摘要翻译：其中X是F，Cl或Br，R1是残基CH 2 OH或者其中R 2表示氢原子，烷基，环烷基，芳基，苯甲酰基或杂环残基 A是-CH 2 -CH 2 - 或顺式-CH = CH-基，B是-CH 2 -CH 2 - 或反式-CH = CH-或-C 3 C C基，W是亚乙二氧基亚甲基或羟基亚甲基基团，D和E一起表示直接键合，或D表示C1-10亚烷基，E表示氧或硫原子，直接键，-C3OND C键或-CR6 = CR7-基，R6 R7表示氢原子，氯原子或烷基，R4表示羟基，R5表示氢原子，烷基，环烷基，芳基或杂环基，其盐与生理上相容的碱，工艺用于其制备，并且其用作抑制胃酸分泌的试剂。

2. 发明授权

US4983629A 11-haloprostane derivatives, processes for their preparation and their use as medicinal agents 失效
标题翻译： 11-卤代前驱烷衍生物，其制备方法及其作为药物的用途
公开(公告)号：US4983629A
公开(公告)日：1991-01-08
申请号：US369168
申请日：1989-06-21
申请人： Helmut Vorbruggen , Norbert Schwarz , Olaf Loge , Claus-Steffen Sturzebecher , Walter Elger
发明人： Helmut Vorbruggen , Norbert Schwarz , Olaf Loge , Claus-Steffen Sturzebecher , Walter Elger
IPC分类号： C07C405/00 , C07D317/20
CPC分类号： C07D317/20 , C07C405/00 , C07C405/0016 , C07C405/0041
摘要： 11-Haloprostane derivatives of general Formula I ##STR1## wherein X is F, Cl or Br,R.sub.1 is the residue CH.sub.2 OH or ##STR2## wherein R.sub.2 means a hydrogen atom, an alkyl, cycloalkyl, aryl, phenacyl or heterocyclic residue,A is a --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--group,B is a --CH.sub.2 --CH.sub.2 -- or trans--CH.dbd.CH-- or a --C.tbd.C--group,W is an ethylenedioxymethylene group or a hydroxymethylene group,D and E together mean a direct bond orD is a C.sub.1-10 -alkylene group,E is an oxygen or sulfur atom, a direct bond, a --C.tbd.C--bond or a --CR.sub.6 .dbd.CR.sub.7 -group with R.sub.6 and R.sub.7 meaning a hydrogen atom, a chlorine atom or an alkyl group,R.sub.4 is a hydroxy group,R.sub.5 is a hydrogen atom, an alkyl, a cycloalkyl, an aryl or a heterocyclic group, andthe salts thereof with physiologically compatible bases, processes for their preparation, and use thereof as agents inhibiting gastric acid secretion.
摘要翻译：其中X是F，Cl或Br，R1是残基CH 2 OH或者其中R 2表示氢原子，烷基，环烷基，芳基，苯甲酰基或杂环残基 A是-CH 2 -CH 2 - 或顺式-CH = CH-基，B是-CH 2 -CH 2 - 或反式-CH = CH-或-C 3 C C基，W是亚乙二氧基亚甲基或羟基亚甲基基团，D和E一起表示直接键合，或D表示C1-10亚烷基，E表示氧或硫原子，直接键，-C3OND C键或-CR6 = CR7-基，R6 R7表示氢原子，氯原子或烷基，R4表示羟基，R5表示氢原子，烷基，环烷基，芳基或杂环基，其盐与生理上相容的碱，工艺用于其制备，并且其用作抑制胃酸分泌的试剂。

3. 发明授权

US4489092A Prostanoic acid derivatives and their preparation 失效
标题翻译：前列腺酸衍生物及其制备
公开(公告)号：US4489092A
公开(公告)日：1984-12-18
申请号：US413940
申请日：1982-09-01
申请人： Helmut Vorbruggen , Norbert Schwarz , Olaf Loge , Walter Elger
发明人： Helmut Vorbruggen , Norbert Schwarz , Olaf Loge , Walter Elger
IPC分类号： A61K31/27 , A61K31/19 , A61K31/215 , A61K31/255 , A61K31/275 , A61P43/00 , C07C51/38 , C07C57/03 , C07C57/13 , C07C57/52 , C07C67/00 , C07C401/00 , C07C405/00 , C07D307/935 , C07F9/535 , C07C177/00 , A61K31/557
CPC分类号： C07D307/935 , C07C405/00 , C07C405/0016 , C07C405/0025 , C07C405/0041 , C07C51/38 , C07C57/03 , C07C57/13 , C07C57/52 , C07F9/5352
摘要： Prostanoic acid derivatives of the formula ##STR1## wherein R.sub.1 is an acid, ester, amide or hydroxyalkylene group; R.sub.2 and R.sub.3 are H or alkyl; R.sub.4 and R.sub.5 are both CH.sub.3 or one is Cl and the other is CH.sub.3 ; A is CH.sub.2 CH.sub.2 or --CH.dbd.CH; B is CH.sub.2 CH.sub.2, trans-CH.dbd.CH, --C.tbd.C-- or ##STR2## W is free or functionally modified hydroxyalkylene or carbonyl; Z is free or functionally modified hydroxymethylene or carbonyl; X Y is either ##STR3## or, when Z is free or functionally modified hydroxymethylene, ##STR4## or, when Z is free or functionally modified carbonyl, --CH.dbd.CH--, R.sub.12 being H, CH.sub.3, CH or free or functionally modified hydroxy; and physiologically acceptable salts thereof when R.sub.1 is an acid group, possess pharmacological activity, including abortion triggering activity.
摘要翻译：其中R1是酸，酯，酰胺或羟基亚烷基的式IMA曲前酯衍生物; R2和R3是H或烷基; R4和R5都是CH3，一个是Cl，另一个是CH3; A是CH 2 CH 2或-CH = CH; B是CH 2 CH 2，反式-CH = CH，-C 3 D或W是游离或官能改性的羟基亚烷基或羰基; Z是游离的或官能改性的羟基亚甲基或羰基; 或者当Z是游离的或官能改性的羟基亚甲基时，或者当Z是游离的或官能改性的羰基时，-CH = CH-，R 12是H，CH 3，CH或游离或官能改性的羟基 ; 当R1为酸基时，其生理上可接受的盐具有药理活性，包括流产触发活性。

4. 发明授权

US4359467A Prostanoic acid derivatives and their preparation 失效
标题翻译：前列腺酸衍生物及其制备
公开(公告)号：US4359467A
公开(公告)日：1982-11-16
申请号：US256369
申请日：1981-04-22
申请人： Helmut Vorbruggen , Norbert Schwarz , Olaf Loge , Walter Elger
发明人： Helmut Vorbruggen , Norbert Schwarz , Olaf Loge , Walter Elger
IPC分类号： A61K31/27 , A61K31/19 , A61K31/215 , A61K31/255 , A61K31/275 , A61P43/00 , C07C51/38 , C07C57/03 , C07C57/13 , C07C57/52 , C07C67/00 , C07C401/00 , C07C405/00 , C07D307/935 , C07F9/535 , C07C177/00 , A61K31/557
CPC分类号： C07D307/935 , C07C405/00 , C07C405/0016 , C07C405/0025 , C07C405/0041 , C07C51/38 , C07C57/03 , C07C57/13 , C07C57/52 , C07F9/5352
摘要： Prostanoic acid derivatives of the formula ##STR1## wherein R.sub.1 is an acid, ester, amide or hydroxyalkylene group; R.sub.2 and R.sub.3 are H or alkyl; R.sub.4 and R.sub.5 are both CH.sub.3 or one is Cl and the other is CH.sub.3 ; A is CH.sub.2 CH.sub.2 or --CH.dbd.CH; B is CH.sub.2 CH.sub.2, trans- ##STR2## W is free or functionally modified hydroxyalkylene or carbonyl; Z is free or functionally modified hydroxymethylene or carbonyl; X Y is either ##STR3## or, when Z is free or functionally modified hydroxymethylene, ##STR4## or, when Z is free or functionally modified carbonyl, --CH.dbd.CH--, R.sub.12 being H, CH.sub.3, CN or free or functionally modified hydroxy; and physiologically acceptable salts thereof when R.sub.1 is an acid group, possess pharmacological activity, including abortion triggering activity.
摘要翻译：其中R1是酸，酯，酰胺或羟基亚烷基的式IMA曲前酯衍生物; R2和R3是H或烷基; R4和R5都是CH3，一个是Cl，另一个是CH3; A是CH 2 CH 2或-CH = CH; B是CH 2 CH 2，反式 - W是游离的或官能改性的羟基亚烷基或羰基; Z是游离的或官能改性的羟基亚甲基或羰基; 或者当Z是游离或官能改性的羟基亚甲基时，或者当Z是游离或官能改性羰基时，-CH = CH-，R 12是H，CH 3，CN或游离或官能改性的羟基 ; 当R1为酸基时，其生理上可接受的盐具有药理活性，包括流产触发活性。

5. 发明授权

US4284646A Prostanoic acid derivatives and their preparation 失效
标题翻译：前列腺酸衍生物及其制备
公开(公告)号：US4284646A
公开(公告)日：1981-08-18
申请号：US69193
申请日：1979-08-24
申请人： Helmut Vorbruggen , Norbert Schwarz , Olaf Loge , Walter Elger
发明人： Helmut Vorbruggen , Norbert Schwarz , Olaf Loge , Walter Elger
IPC分类号： A61K31/27 , A61K31/19 , A61K31/215 , A61K31/255 , A61K31/275 , A61P43/00 , C07C51/38 , C07C57/03 , C07C57/13 , C07C57/52 , C07C67/00 , C07C401/00 , C07C405/00 , C07D307/935 , C07F9/535 , C07C177/00
CPC分类号： C07D307/935 , C07C405/00 , C07C405/0016 , C07C405/0025 , C07C405/0041 , C07C51/38 , C07C57/03 , C07C57/13 , C07C57/52 , C07F9/5352
摘要： Prostanoic acid derivatives of the formula ##STR1## wherein R.sub.1 is an acid, ester, amide or hydroxyalkylene group; R.sub.2 and R.sub.3 are H or alkyl; R.sub.4 and R.sub.5 are both CH.sub.3 or one is Cl and the other is CH.sub.3 ; A is CH.sub.2 CH.sub.2 or --CH.dbd.CH; B is CH.sub.2 CH.sub.2, trans-CH.dbd.CH, --C.tbd.C--or ##STR2## W is free or functionally modified hydroxyalkylene or carbonyl; Z is free or functionally modified hydroxymethylene or carbonyl; X Y is either ##STR3## or, when Z is free or functionally modified hydroxymethylene, ##STR4## or, when Z is free or functionally modified carbonyl, --CH.dbd.CH--, R.sub.12 being H, CH.sub.3, CN or free or functionally modified hydroxy; and physiologically acceptable salts thereof when R.sub.1 is an acid group, possess pharmacological activity, including abortion triggering activity.
摘要翻译：其中R1是酸，酯，酰胺或羟基亚烷基的式IMA曲前酯衍生物; R2和R3是H或烷基; R4和R5都是CH3，一个是Cl，另一个是CH3; A是CH 2 CH 2或-CH = CH; B是CH 2 CH 2，反式-CH = CH，-C 3BOND C - 或W是游离或官能改性的羟基亚烷基或羰基; Z是游离的或官能改性的羟基亚甲基或羰基; 或者当Z是游离或官能改性的羟基亚甲基时，或者当Z是游离或官能改性羰基时，-CH = CH-，R 12是H，CH 3，CN或游离或官能改性的羟基 ; 当R1为酸基时，其生理上可接受的盐具有药理活性，包括流产触发活性。

6. 发明授权

US4235930A Novel acetylenic prostaglandins and processes for the preparation thereof 失效
标题翻译：新型炔类前列腺素及其制备方法
公开(公告)号：US4235930A
公开(公告)日：1980-11-25
申请号：US920523
申请日：1978-06-29
申请人： Werner Skuballa , Bernd Raduchel , Helmut Vorbruggen , Walter Elger , Olaf Loge , Ekkehard Schillinger
发明人： Werner Skuballa , Bernd Raduchel , Helmut Vorbruggen , Walter Elger , Olaf Loge , Ekkehard Schillinger
IPC分类号： A61K31/18 , A61K31/215 , A61K31/34 , A61K31/341 , A61K31/343 , A61K31/38 , A61K31/381 , A61K31/435 , A61P43/00 , C07C67/00 , C07C401/00 , C07C405/00 , C07D307/20 , C07D307/935 , C07D309/12 , C07D333/32 , C07F9/40 , C07C177/00 , A61K31/557
CPC分类号： C07D307/935 , C07C405/00 , C07F9/4015 , Y02P20/55
摘要： Prostane derivatives of the formula ##STR1## wherein R.sub.1 is the residue OR.sub.2 and R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or is NHR.sub.3 wherein R.sub.3 is an acyl group derived from a hydrocarbon carboxylic or sulfonic acid of up to 15 carbon atoms;A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--Z is carbonyl or ##STR2## wherein the OR.sub.4 group can be in the .alpha.- or .beta.-position and R.sub.4 is H or a hydroxy-protective groupX Y is ##STR3## wherein R.sub.4 is as defined above, --CH.sub.2 -- CH.sub.2 -- or --CH.sub.2 --CH-- wherein R.sub.5 is alkyl or 1-5 carbon atoms, if Z is R.sub.5 carbonyl or ##STR4## X Y represents --CH.dbd.CH-- if Z is carbonyl: R.sub.6, R.sub.7, R.sub.8, R.sub.9 and R.sub.10 each independently is hydrogen or an alkyl group of 1-5 carbon atoms; andR.sub.11 is alkyl of 1-5 carbon atoms;and if R.sub.2 is hydrogen, the salts thereof with physiologically compatible bases are prostaglandins having prolonged duration of activity and increased selectivity of effectiveness.
摘要翻译：其中R1是残基OR2，R2是氢，烷基，环烷基，芳基或杂环残基的式或者是NHR 3，其中R 3是衍生自至多15个碳原子的烃羧酸或磺酸的酰基; A是-CH 2 -CH 2 - 或顺式-CH = CH-Z是羰基或者其中OR 4基团可以是α或β-位，R 4是H或羟基保护基团XY是其中R 4如上定义，-CH 2 -CH 2 - 或-CH 2 -CH-，其中R 5是烷基或1-5个碳原子，如果Z是R 5羰基或如果Z是羰基，则X代表-CH = CH- R6，R7，R8，R9和R10各自独立地为氢或1-5个碳原子的烷基; R11为1-5个碳原子的烷基; 并且如果R 2是氢，则其与生理上相容的碱的盐是具有延长的活性持续时间和增加的有效性选择性的前列腺素。

7. 发明授权

US4154953A Crystalline prostanoic acid esters 失效
标题翻译：结晶前列腺酸酯
公开(公告)号：US4154953A
公开(公告)日：1979-05-15
申请号：US826908
申请日：1977-08-19
申请人： Werner Skuballa , Bernd Raduchel , Helmut Vorbruggen , Walter Elger , Olaf Loge , Wolfgang Losert
发明人： Werner Skuballa , Bernd Raduchel , Helmut Vorbruggen , Walter Elger , Olaf Loge , Wolfgang Losert
IPC分类号： C07C405/00 , C07C177/00
CPC分类号： C07C405/00
摘要： Prostanoic acid esters of the formulaPG-- CH.sub.2 -- X-- Ywherein PG is the prostanoyloxy radical of a prostaglandin, X is a carbon-carbon single bond, carbonyl or carbonyloxy, and Y is substituted phenyl are easily crystallized compounds at least as active as the unesterified prostanoic acid and useful for the purification of the parent prostaglandin are prepared by reacting, in the presence of an agent which splits off hydrogen halide, the unesterified prostaglandin with a halide of the formula Hal--CH.sub.2 --X--Y, wherein Hal is a halogen atom and X and Y have the values given above.
摘要翻译：式PG-CH2-X-Y的前列腺酸，其中PG是前列腺素的前烷氧基自由基，X是碳 - 碳单键，羰基或羰氧基，Y是取代的苯基，容易结晶化合物至少与通过使未分解的前列腺素与式Hal-CH2-XY的卤化物反应，其中Hal是卤素，其中Hal是卤素原子，X和Y具有上面给出的值。

8. 发明授权

US3962218A Novel prostanoic acid derivatives and processes for the preparation thereof 失效
标题翻译：新型乳酸衍生物及其制备方法
公开(公告)号：US3962218A
公开(公告)日：1976-06-08
申请号：US472738
申请日：1974-05-23
申请人： Bernd Raduchel , Werner Skuballa , Helmut Vorbruggen , Walter Elger , Wolfgang Losert , Olaf Loge
发明人： Bernd Raduchel , Werner Skuballa , Helmut Vorbruggen , Walter Elger , Wolfgang Losert , Olaf Loge
IPC分类号： C07C67/00 , C07C401/00 , C07C405/00 , C07D307/935 , C07D317/30 , C07D317/54 , C07D319/06 , C07C177/00 , C07D317/12 , C07D317/50 , C07D319/04
CPC分类号： C07D307/935 , C07C405/00 , C07C405/0016 , C07D317/30 , C07D317/54 , C07D319/06
摘要： Prostaglandins of the formula ##SPC1##Wherein R.sub.1 is HOCH.sub.2, --COOH, a salt thereof or an ester thereof; R.sub.2 is OH; and R.sub.3 is H or R.sub.2 and R.sub.3 collectively are = O. A is --CH.sub. 2 --CH.sub.2 -- or --(trans)--CH=CH--, B is --CH.sub. 2 CH.sub.2 --or --(cis)--CH=CH-- and R.sub.4 --O--O--R.sub.5 is a ketal group, are superior in physiological activity to the corresponding 15-.alpha.-hydroxy-prostaglandins.

9. 发明授权

US4004020A Novel prostanoic acid derivatives and process for the preparation thereof 失效
标题翻译：新型前列腺酸衍生物及其制备方法
公开(公告)号：US4004020A
公开(公告)日：1977-01-18
申请号：US534483
申请日：1974-12-19
申请人： Werner Skuballa , Bernd Raduchel , Helmut Vorbruggen , Walter Elger , Wolfgang Losert , Olaf Loge
发明人： Werner Skuballa , Bernd Raduchel , Helmut Vorbruggen , Walter Elger , Wolfgang Losert , Olaf Loge
IPC分类号： C07D317/14 , C07D317/46 , C07D317/70 , C07D319/06 , C07D319/08 , C07F9/40 , C07F9/54 , A01N9/28 , A61K31/335
CPC分类号： C07F9/4006 , C07D317/46 , C07D317/70 , C07D319/06 , C07F9/5407
摘要： Prostaglandins of the formula ##STR1## wherein R.sub.1 is hydroxymethyl, carboxy, aryloxycarbonyl, alkoxycarbonyl of 1-8 carbon atoms in the alkoxy group, or the group -COO-CH.sub.2 -U-V wherein U is a direct C-C bond, carbonyl or carbonyloxy and V is phenyl substituted by phenyl, alkoxy of 1-2 carbon atoms or halogen; R.sub.2 is hydroxy and R.sub.3 is a hydrogen atom or R.sub.2 and R.sub.3 collectively are an oxygen atom; A is -CH.sub.2 -CH.sub.2 or trans-CH=CH; B is -CH.sub.2 -CH.sub.2 or CH=CH; one of R.sub.4 and R.sub.5 is hydroxy and the other is a hydrogen atom; R.sub.6 and R.sub.7 each are alkyl of 1-10 carbon atoms or collectively are alkylene of up to 7 carbon atoms and with 2-3 carbon atoms in the chain, phenylene or naphthylene; R.sub.8 is a hydrogen atom or alkyl of 1-5 carbon atoms; ##STR2## when R.sub.2 is hydroxy and R.sub.3 is a hydrogen atom or is ##STR3## or -CH=CH- when R.sub.2 and R.sub.3 collectively are an oxygen atom; or, when R.sub.1 is carboxy, a physiologically acceptable salt thereof with a base, possess the activity of the corresponding natural prostaglandins, including a luteolytic effect, and are useful in triggering abortions and syncronizing the conception cycle of mammals.
摘要翻译：其中R1是羟甲基，羧基，芳氧基羰基，烷氧基中1-8个碳原子的烷氧基羰基或基团-COO-CH2-UV，其中U是直接的CC键，羰基或羰基氧基和V 是被苯基，1-2个碳原子的烷氧基或卤素取代的苯基; R2是羟基，R3是氢原子，R2和R3一起是氧原子; A是-CH 2 -CH 2或反式-CH = CH; B是-CH 2 -CH 2或CH = CH; R4和R5之一是羟基，另一个是氢原子; R6和R7各自为1-10个碳原子的烷基，或者统称为至多7个碳原子的亚烷基，链中有2-3个碳原子，亚苯基或亚萘基; R8是氢原子或1-5个碳原子的烷基; 当R2和R3共同为氧原子时，当R 2为羟基且R 3为氢原子或者为或者-CH = CH-时，或者，当R 1为羧基时，其与碱的生理上可接受的盐具有相应的天然前列腺素的活性，包括溶血性作用，并且可用于触发哺乳动物的受孕循环的流产和同步化。

10. 发明授权

US4256745A New prostane derivatives and process for their preparation 失效
标题翻译：新的前列腺衍生物及其制备方法
公开(公告)号：US4256745A
公开(公告)日：1981-03-17
申请号：US882687
申请日：1978-03-02
申请人： Werner Skuballa , Bernd Raduchel , Helmut Vorbruggen , Walter Elger , Olaf Loge , Eckehard Schillinger
发明人： Werner Skuballa , Bernd Raduchel , Helmut Vorbruggen , Walter Elger , Olaf Loge , Eckehard Schillinger
IPC分类号： A61K31/21 , A61K31/27 , C07C67/00 , C07C401/00 , C07C405/00 , C07D309/12 , C07C177/00 , C07C69/02
CPC分类号： C07C405/0016 , C07C405/0025 , C07D309/12
摘要： Prostan-1-ol esters and intermediates for their preparation are described; the former compounds exhibit improved organ specificity and a longer duration of activity at lower dosages than the corresponding non-esterified prostaglandins and are useful, inter alia, in triggering abortion, inducing labor and regulating the menstrual cycle.
摘要翻译：描述了用于其制备的丙烷-1-醇酯和中间体; 前者的化合物表现出改善的器官特异性和较低的剂量比相应的未酯化的前列腺素更长的活性持续时间，并且尤其用于触发流产，诱导劳动和调节月经周期。

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