公开(公告)号：US3891677A

公开(公告)日：1975-06-24

申请号：US38031973

申请日：1973-07-18

Applicant: SCHERING CORP

Inventor： TANABE MASATO

IPC: C07J7/00 ,  C07J21/00 ,  C07J41/00 ,  C07J75/00 ,  C07D13/04

CPC classification number: C07J21/00 ,  C07C2603/16 ,  C07J7/0045 ,  C07J7/007 ,  C07J41/0005 ,  C07J75/005

Abstract: Steroidal 5-keto-4,5-seco-3-ynes of the estrane, androstane, and pregnane series are prepared from 3-keto-4-dehydro steroids via the 3-hydrocarbon-sulfonylhydrazono-4,5-oxido derivative thereof which undergoes fission and rearrangement in situ to form the 5keto-4,5-seco-3-yne structure. The 6- and/or 10-hydrocarbon substituted-5-keto-4,5-seco-3-ynes are prepared by reacting a 6and/or 10-unsubstituted-5-keto-4,5-seco-3-yne in an alkylating medium with a hydrocarbon sulfonate or, preferably, a hydrocarbon halide. The steroidal 5-keto-4,5-seco-3-ynes of this invention are useful as intermediates in preparing pharmacologically valuable 6- and/or 10-hydrocarbon substituted-3-keto-4-dehydro steroids, e.g. 1. BY REACTION WITH MERCURIC ACETATE AND SULFURIC ACID IN ACETIC ACID; OR 2. BY REACTION WITH MERCURIC OXIDE AND TRIFLUOROACETIC ACID FOLLOWED BY TREATMENT OF THE THEREBY FORMED 3,5-DIKETO-4,5-SEC. STEROID WITH POTASSIUM T-BUTOXIDE IN T-BUTANOL.

Abstract translation: 通过其3-烃基 - 磺酰基亚肼基-4,5-氧化物衍生物从3-酮-4-脱氢甾类化合物制备雌激素甾烷醇5-酮基-4,5-二硫杂环戊烷和孕烷系列， 在原位进行裂变和重排以形成5-酮-4,5-仲-3-炔结构。 6-和/或10-烃取代-5-酮-4,5-仲-3-炔通过6-和/或10-未取代的-5-酮-4,5-仲-3-基 - 在具有烃磺酸盐或优选烃卤化物的烷基化介质中。

公开(公告)号：US3890306A

公开(公告)日：1975-06-17

申请号：US37288173

申请日：1973-06-20

Applicant: EASTMAN KODAK CO

Inventor： MCCOLLUM ANTHONY W

IPC: B26D7/26 ,  C08B15/10 ,  C08G4/00 ,  C08G63/00 ,  C08G65/16 ,  C08K5/1565 ,  C07D13/04

CPC classification number: C08G4/00 ,  B26D7/26 ,  C08B15/10 ,  C08G63/00 ,  C08G65/16 ,  C08K5/1565

Abstract: 1,1,4,4-Bis(ethylenedioxy)-3,3-dimethyl-1-butene (referred to as ketene acetal) is prepared by reacting ethylene glycol with tetrahydro-2-isopropyl-6,6-dimethylfuro-(2,3-d)-1,3-dioxol-5-ol in the presence of an acid catalyst at a temperature of from about 110* to 170*C. The water of reaction is preferably removed by the use of a solvent which forms an azeotrope that boils between 110* to 170*C. In an alternative two-step process, tetrahydro-2-isopropyl-6,6-dimethylfuro-(2,3-d)-1,3-dioxol-5-ol is reacted with ethylene glycol in the presence of an acid catalyst at a temperature of from about 60* to 110*C. to form 2hydroxy-3,3-dimethylsuccinaldehyde bis(ethylenedioxy)acetal (referred to as hydroxy acetal). The 2-hydroxy-3,3dimethylsuccinaldehyde bis(ethylenedioxy)acetal is then heated to a temperature of from about 110* to 170*C. in the presence of an acid catalyst to give 1,1,4,4-bis(ethylenedioxy)-3,3-dimethyl-1butene. The water from the two-step process is preferably removed from the reaction as it is formed through the use of an azeotropic solvent. The ketene acetal is useful generally because of its reactive nature and for its ability to form oxetane polymers and polyesters. The hydroxy acetal is useful as a gel hardener, as a cross-linking agent for use with cellulose derivatives and polyols, and as a chemical intermediate.

公开(公告)号：US3833612A

公开(公告)日：1974-09-03

申请号：US20197971

申请日：1971-11-24

Applicant: MERCK & CO INC

Inventor： WENDLER N ,  TAUB D ,  SLATES H ,  ZELAWSKI Z

IPC: C07C405/00 ,  C07D307/935 ,  C07D317/72 ,  C07D13/04

CPC classification number: C07D307/935 ,  C07C309/00 ,  C07C405/00 ,  C07D317/72

Abstract: RACEMIC OR OPTICALLY ACTIVE PROSTAGLANDIN E1 IS SYNTHESIZED FROM RACEMIC OR OPTICALLY ACTIVE PRECURSORS IN GOOD YIELD AT THE VARIOUS STEPS FROM 3A,6,7A-TETRAHYDRO4-METHYL-2-OXO-1B-INDANEHEPTANOIC ACID METHYL ESTER PROCEEDING THROUGH 2B-(2-CARBOXYETHYL)-3B-HYDROXY-5OXO-1B-CYCLOPENTANEHEPTANOIC ACID METHYL ESTER, $-LACTONE, 5-CYCLIC ETHYLENE ACETAL, 2A-(2-CARBOXY-2-FORMYLETHYL)3B-HYDROXY-5-OXO-1B-CYCLOPENTANEHEPTANOIC ACID METHYL ESTER, $-LACTONE, 5-CYCLIC ETHYLENE ACETAL, 2A-(2-CARBOXY2-OXOETHYL)-3B-HYDROXY-5-OXO-1B-CYCLOPENTANEHEPTANOIC ACID METHYL ESTER, $-LACTONE, 5-CYCLIC ETHYLEN ACETAL, ANND 3B-HYDROXY-2A-(3-OXO-1-OCTENYL)-5-OXO-1B-CYCLOPENTANEHEPTANOIC ACID METHYL ESTER, 5-CYCLIC ETHYLENE ACETAL.

公开(公告)号：US3821253A

公开(公告)日：1974-06-28

申请号：US22227872

申请日：1972-01-31

Applicant: SYNTEX CORP

Inventor： FRIED J ,  HARRISON I

IPC: C07C57/40 ,  C07C57/46 ,  C07C57/58 ,  C07D317/12 ,  C07D317/16 ,  C07D317/20 ,  C07D317/26 ,  C07D317/30 ,  C07D13/04

CPC classification number: C07D317/30 ,  C07C45/41 ,  C07C57/40 ,  C07C57/46 ,  C07C57/58 ,  C07C251/40 ,  C07C251/80 ,  C07C309/24 ,  C07C323/22 ,  C07C323/48 ,  C07C323/66 ,  C07D317/12 ,  C07D317/16 ,  C07D317/20 ,  C07D317/26 ,  C07C47/277

Abstract: 2-(2''-Naphthyl) acetaldehyde derivatives optionally substituted at the 2 position and/or positions C-1'',4'',5'',7'' or 8''; and/or position C-6'' or positions C-5'' and 7'' exhibit anti-inflammatory, analgesic, antipyretic and anti-pruritic activity.

公开(公告)号：US3795682A

公开(公告)日：1974-03-05

申请号：US3795682D

申请日：1970-07-27

Applicant: UNION CARBIDE CORP

Inventor： DELAVARENNE S

IPC: C07D263/04 ,  C07D317/16 ,  C07D317/20 ,  C07D319/06 ,  C07D321/06 ,  C07D13/04

CPC classification number: C07D263/04 ,  C07D317/16 ,  C07D317/20 ,  C07D319/06 ,  C07D321/06

Abstract: CYCLIC KETALS ARE PRODUCED BY CONTACTING A DEHYDRATING AGENT WITH A COMPOUND OF THE FORMULA:

HO-C(-R2)(-R3)-X1-R1-X2H

WHEREIN X1 REPRESENTS OXY, THIO, OR NITRILO, WHEREIN X2 REPRESENTS OXY, THIO, OR IMINO, PROVIDED THAT AT LEAST ONE OF X1 AND X2 REPRESENTS OXY, WHEREIN R1 REPRESENTS AN ALKYLENE GROUP OF FROM 2 TO 4 CARBON ATOMS OR A 2BUTYLENE GROUP, AND WHEREIN R2 AND R3 INDIVIDUALLY REPRESENT HALOGENATED ALKYL GROUPS THE ALPHA CARBON ATOMS BEING FLUORO, CHLORO, OR BROMO. THE CYCLIC KETALS PROGROUP, THE REMAINDER OF THE HALO GROUPS ON THE ALKYL BEING FLUORO, CHLORO, OR BROMO. THE CYCLIC KETALS PRODUCED ARE REPRESENTED BY THE FORMULA:

R2-C(-R3)
WHEREIN X1, R2, AND R3 ARE AS DEFINED ABOVE, AND WHEREIN R4 REPRESENTS ALKYLENE OF 2 TO 4 CARBON ATOMS OR SUBSTITUTED ALKYLENE. THE DEHYDRATING AGENTS EMPLOYED INCLUDE CARBODIIMIDES AND ALPHA-AMINOACETYLENES. THE PROCCESS OF THE INVENTION IS USEFUL FOR THE PREPARATION OF 1,3DIOXOLANES, 1,3 - DIOXANES, 1,3 - DIOXEPANES, AND THEIR ANALOGUES WHEREIN ONE OF THE OXYGEN ATOMS IN THE HETEROCYCLIC RING IS REPLACED BY EITHER A SULFUR ATOM OR NITRILO GROUP.

公开(公告)号：US3792062A

公开(公告)日：1974-02-12

申请号：US3792062D

申请日：1971-10-26

Applicant: STAUFFER CHEMICAL CO

Inventor： TEACH E

IPC: C07D317/28 ,  C07D319/06 ,  C07D13/04 ,  C07D15/04

CPC classification number: C07D317/28 ,  C07D319/06

Abstract: SUBSTITUTED ANILIDE DIOXOLANES AND DIOXANE COMPOUNDS HAVING THE FORMULA

(R6-C(-R7)
CO-R)-O-C(-R2)(-R3)-)

IN WHICH R IS SELECTED FROM THE GROUP CONSISTING OF ALKYL AND HALOALKYL; R1, R2, R3, R4, R5 AND R7 EACH ARE INDEPPENDENTLY SELECTED FROM THE GROUP CONSISTING OF HYDROGEN AND LOWER ALKYL; R6 IS SELECTED FROM THE GROUP CONSISTING OF ALKYL, HALOALKYL, HYDROGEN, HYDROXYMETHYL, LOWER ALKOXY CARBONYLOXYMETHYL, N-LOWER ALKYL CARBAMOYLOXYMETHYL AND N-PHENYLCARBAMOYLOXYMETHYL; AND N IS 0 TO 1. THESE COMPOUUNDS ARE USEFUL AS HERBICIDES.

公开(公告)号：US3767677A

公开(公告)日：1973-10-23

申请号：US3767677D

申请日：1970-07-08

Applicant: HOFFMANN LA ROCHE

Inventor： WEHRLI P

IPC: C07C45/75 ,  C07C49/12 ,  C07D317/26 ,  C07D13/04

CPC classification number: C07D317/26 ,  C07C45/75 ,  C07C49/12

Abstract: A TWO-STEP PROCESS FOR THE PREPARATION F 6,6-ALKYLENEDIOXYHEPTAN-2-ONE STARTING FROM DIKETENE AND FORMALDEHYDE IS DESCRIBED. IN THE FIRST STEP DIKETENE AND FORMALDEHYDE ARE RELATED TO FORM 2,6-HEPTANEDIONE. SELECTIVE KETALIZATION OF THE LATTER COMPOUND RESULTS IN THE FORMATION OF 6,6-ALKYLENDIOXYHEPTAN-2-ONE AS MAJOR PRODUCT. RECYCLE OF BY-PRODUCT DIKETAL OBTAINED IN THIS STEP IS ALSO DESCRIBED. THE FINAL PRODUCT IS USEFUL AS AN INTERMEDIATE IN THE TOTAL SYNTHESIS OF MEDICINALLY VALUBLE STERIODS.

公开(公告)号：US3741988A

公开(公告)日：1973-06-26

申请号：US3741988D

申请日：1971-04-12

Applicant: ROUSSEL UCLAF

Inventor： ALLAIS A ,  MEIER J ,  DUBE J

IPC: C07C69/738 ,  A61K31/215 ,  A61K31/25 ,  A61K31/335 ,  A61K31/357 ,  A61P25/04 ,  A61P29/00 ,  C07C49/813 ,  C07C51/08 ,  C07C59/88 ,  C07C65/36 ,  C07C67/00 ,  C07C245/14 ,  C07C313/00 ,  C07C323/62 ,  C07D317/24 ,  C07F3/00 ,  C07D13/04

CPC classification number: C07F3/00 ,  C07C49/813 ,  C07C51/08 ,  C07C59/88 ,  C07C65/36 ,  C07C245/14 ,  C07D317/24

Abstract: Racemates and optically active isomers of benzoylphenylacetic acid esters of the formula

WHEREIN R is selected from the group consisting of hydrogen and alkyl of one to seven carbon atoms, R1 and R2 are hydrogen or taken together are

P and Q being alkyl of one to five carbon atoms and the two benzene rings may be optionally substituted with at least one member of the group consisting of chlorine, fluorine, bromine, trifluoromethyl and alkyl and alkoxy and alkylthio of one to seven carbon atoms, intermediates and process for their preparation and their use as analgesics and antiinflammatory agents.

Abstract translation: 式WHEREIN R的苯甲酰基苯基乙酸酯的外消旋物和旋光异构体选自氢和1至7个碳原子的烷基，R 1和R 2是氢或一起是P和Q是一至五个碳的烷基 原子，两个苯环可以任选被至少一个由氯，氟，溴，三氟甲基组成的组中的一个或多个碳原子的烷基和烷氧基和烷硫基取代，中间体及其制备方法及其用途如 镇痛药和抗炎药。

公开(公告)号：US3714202A

公开(公告)日：1973-01-30

申请号：US3714202D

申请日：1969-07-15

Applicant: ATLANTIC RICHFIELD CO

Inventor： NAKAGUCHI G ,  WANG T ,  CASERIO F

IPC: C07D317/14 ,  C07D319/06 ,  C07D13/04

CPC classification number: C07D319/06 ,  C07D317/14

Abstract: Two classes of vinyl cyclic acetal compounds, 2-methyl-5vinyloxy-1,3-dioxane and 2-methyl-4-vinyloxymethyl-1,3-dioxolane in particular, and a process for preparing compounds of these classes by catalytic pyrolysis are disclosed.

Abstract translation: 二级乙烯基环缩醛化合物，2-甲基-5-乙烯基氧基-1,3-二恶烷和2-甲基-4-乙烯基氧基甲基-1,3-二氧戊环，以及通过催化裂解制备这些化合物的方法 被披露。

公开(公告)号：US3708503A

公开(公告)日：1973-01-02

申请号：US3708503D

申请日：1970-01-26

Applicant: CIBA GEIGY CORP

Inventor： ANNER G ,  WIELAND P

IPC: A61K31/12 ,  A61P25/04 ,  C07J63/00 ,  C07J75/00 ,  C07D13/04

CPC classification number: C07J63/00 ,  C07J75/00

Abstract: COMPOUNDS OF THE FORMULA

1-(R1=),7-OXO,8-R2,12A-(H3C-)-1,2,3,3A,3B,4,5,10A,10B,11,

12,12A-CYCLOHEPTA(A)CYCLOPENTA(F)NAPHTHALENE

WHEREIN R1 IS A FREE OR KETALIZED OXO GROUP OR A B-POSITIONED FREE, ESTERIFIED OR ETHERIFIED HYDROXY GROUP TOGETHER WITH A LOWER ALIPHATIC SATURATED OR UNSATURATED HYDROCARBON RESIDUE, R2 STANDS FOR AN AMINO GROUP OR A FREE, ESTERIFIED OR ETHERIFIED HYDROXYL GROUP, AND THE SALTS OF THE AMINO COMPOUNDS. USE AS AGENTS FOR FERTILITY CONTROL.