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公开(公告)号：DE19701032A1
公开(公告)日：1997-07-17
申请号：DE19701032
申请日：1997-01-15
Applicant: DEGUSSA
Inventor： WECKBECKER CHRISTOPH DR , DRAUZ KARLHEINZ PROF DR
IPC: A01N43/90 , C07C243/28 , C07D249/12 , C07D471/04 , C07C243/26 , A01N43/653 , C07D405/04 , C07D409/04 , C07D413/04 , C07D417/04
Abstract: Preparation of 2-(phenyl or benzoheterocyclyl)-4,5-dialkyl-1,2,4-triazolin-3(2H)-(thi)one derivatives of formula (I) involves (i) reacting an amide of formula (IV) with phosgene or thiophosgene (or a substitute), optionally in a solvent, to give an N-(chloro(thio)carbonyl)-chloro-enamine compound of formula (V) and (ii) reacting (V) with a hydrazide of formula QNHNHCOR (VI) or its acid addition salt, optionally in presence of a diluent, optionally initially in presence of a base then in presence of an acid and optionally with elevation of temperature. X = O or S; R = 2-8C alkoxyalkyl, 2-8C haloalkoxyalkyl, alkyl, haloalkyl, cyanoalkyl, 2-8C alkylthioalkyl, 2-8C alkylsulphinylalkyl, 2-8C alkylsulphonylalkyl, 7-8C aralkyl (e.g. benzyl), 2-8C alkenyl, 2-8C haloalkenyl, 2-8C alkynyl, 2-8C haloalkynyl, aryl such as phenyl or naphthyl (optionally substituted by one or more of halogen, 1-3C alkyl and 1-3C alkoxy), or heteroaryl such as pyridyl (optionally substituted by halogen); R ,R = H, 2-6C alkoxyalkyl, 2-6C haloalkoxyalkyl, 1-6C alkyl, 1-6C haloalkyl, (1-6C)cyanoalkyl, 1-6C alkylthio, 2-6C alkylthioalkyl, 2-6C alkylsulphinylalkyl, 2-6C alkylsulphonylalkyl, 2-6C alkenyl, 2-6C haloalkenyl, 2-6C alkynyl or 2-6C haloalkynyl; or aralkyl or optionally substituted aryl as defined for R ; or heteroaryl such as pyridyl; alternatively R +R complete a ring, so that (I) is a bicyclic compound of formula (I'); n,m = 0-3; Z = CR R , O, S, SO, SO2, N(1-4C alkyl), N(1-4C haloalkyl), CO, C=NR or CS; R = H, 1-3C alkyl, halogen, 1-6C alkoxy, 1-6C haloalkyl, 1-6C haloalkoxy, 2-6C alkylcarbonyloxy or 2-6C haloalkylcarbonyloxy; R = H, 1-3C alkyl or halogen; R and R may each substitute the ring in one or more positions, up to a total of 12 substituents (m = n = 3); Q = aryl or benzo-heterocyclic group of formula (Q1)-(Q7); W = O or S; R = H or halogen; R = H, alkyl, haloalkyl, halogen, OH, OR , SH, S(O)pR , COR , COOR , C(O)SR , CONR R , CHO, CR =NOR , CHCR COOR , CH2CHR COOR , COON=CR R , NO2, CN, NHSO2R , NR R , NH2 or phenyl (optionally substituted by R ); p = 0-2; R = 1-2C alkyl, 1-2C haloalkyl, OMe, SMe, OCHF2, halogen, CN or NO2; R = H, 1-3C alkyl or halogen; R = H, 1-3C alkyl, halogen, 1-3C haloalkyl, cyclopropyl, vinyl, ethynyl, CN, COR , COOR , CONR R , CR R CN, CR R COR , CR R COOR , CR R CONR R , CHR OH, CHR OCOR or OCHR OCONR R ; or in (Q2), CR R may be CO; R = H, 1-6C alkyl, 1-6C haloalkyl, 3-6C haloalkenyl, 2-6C alkoxyalkyl, 3-6C alkenyl, 3-6C alkynyl, 3-6C haloalkynyl, 4-7C cycloalkylalkyl, CHR COOR , CHR CN, CHR CH=CHCOOR or glycidyl; R = alkyl, 3-8C cycloalkyl, 3-8C alkenyl, 3-8C alkynyl, haloalkyl, 2-8C alkoxyalkyl, 2-8C alkylthioalkyl, 2-8C alkylsulphinylalkyl, 2-8C alkylsulphonylalkyl, 4-8C alkoxyalkoxyalkyl, 4-8C cycloalkylalkyl, 6-8C cycloalkoxyalkyl, 4-8C alkenyloxyalkyl, 4-8C alkynyloxyalkyl, 3-8C haloalkoxyalkyl, 4-8C haloalkenyloxyalkyl, 4-8C haloalkynyloxyalkyl, 6-8C cycloalkylthioalkyl, 4-8C alkenylthioalkyl, 4-8C alkynylthioalkyl, 1-4C alkyl substituted by phenoxy or benzyloxy (both optionally ring-substituted by halogen, 1-3C alkyl or 1-3C haloalkyl), 4-8C trialkylsilylalkyl, 3-8C cyanoalkyl, 3-8C halocycloalkyl, 3-8C haloalkenyl, 5-8C alkoxyalkenyl, 5-8C haloalkoxyalkenyl, 5-8C alkylthioalkenyl, 3-8C haloalkynyl, 5-8C alkoxyalkynyl, 5-8C haloalkoxyalkynyl, 5-8C alkylthioalkynyl, 2-8C alkylcarbonyl, benzyl (optionally substituted by halogen, 1-3C alkyl or 1-3C haloalkyl), CHR COR , CHR P(O)(OR )2, CHR P(S)(OR )2, P(O)(OR )2, P(S)(OR )2, CHR CONR R , CHR CONH2, CHR COOR , COOR , SO2R , phenyl (optionally substituted by R ), 1,3-dioxolan-2-ylmethyl or glycidyl; R = 1-6C alkyl, 1-6C haloalkyl, 3-6C alkenyl or 3-6C alkynyl; R ,R ,R ,R ,R = H or 1-4C alkyl moieties have 1-8C unless specified otherwise. The following intermediates are new compounds: formic acid N'-(2,4-dichloro-5-hydroxyphenyl)hydrazide (VIb) and formic acid N'-(2,4-dichloro-(5-prop-2-ynyloxy)phenyl)hydrazide (VIa).
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公开(公告)号：DE102011078468A1
公开(公告)日：2013-01-03
申请号：DE102011078468
申请日：2011-06-30
Applicant: EVONIK DEGUSSA GMBH
Inventor： HOPPE CARL-FRIEDRICH DR , NORDSCHILD ANJA , JAKOB HARALD DR , WECKBECKER CHRISTOPH DR , ROTH PHILIPP , MOUSSALLEM IMAD
IPC: C25B3/25 , C07B41/08 , C07C323/52 , C25B9/23
Abstract: Die Erfindung betrifft ein Verfahren zur Herstellung von alpha-substituierten Carbonsäuren ausgewählt aus der Gruppe alpha-Hydroxycarbonsäuren, N-substituierte alpha-Aminocarbonsäuren, umfassend den Schritt einer kathodischen Carboxylierung einer Verbindung R1-C(=X)R in einem Leitsalz und organisches Lösungsmittel enthaltenden Katholyt mit Kohlendioxid an einer Diamantschichtkathode, wobei die Carboxylierung in einer in einen Kathodenraum und einen Anodenraum geteilten Elektrolysezelle abläuft, wobei R1 einen gegebenenfalls substituierten Rest darstellt ausgewählt aus einem linearen, verzweigten oder cyclischen Alkyl-, Arylalkyl-, Aryl- und Heteroarylrest; R2 Wasserstoff oder einen gegebenenfalls substituierten Rest darstellt ausgewählt aus einem linearen, verzweigten oder cyclischen Alkyl-, Arylalkyl-, Aryl- und Heteroarylrest, X = O oder N-R3 darstellt, wobei R3 für OH oder für einen gegebenenfalls substituierten Rest ausgewählt aus einem linearen, verzweigten oder cyclischen Alkyl-, Arylalkyl-, Aryl- und Heteroarylrest steht, wobei an der Anode im Anolyt vorliegendes H2 zu H+-Ionen umgesetzt wird. Weiterhin stellt die Erfindung eine Elektrolysezelle bereit mit einem Trennelement, das den Elektrolysenraum in einen Kathodenraum und einen Anodenraum trennt, wobei eine stoffdurchlässige Anode, eine Kationenaustauschermembran als Trennelement und eine stoffdurchlässige Kathode vorgesehen sind, die planparallel angeordnet sind und die Anode und die Kathode direkt auf dem Trennelement aufliegen.
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公开(公告)号：DE19601189A1
公开(公告)日：1997-07-17
申请号：DE19601189
申请日：1996-01-15
Applicant: DEGUSSA
Inventor： WECKBECKER CHRISTOPH DR , DRAUZ KARLHEINZ PROF DR
IPC: C07D249/12 , C07D403/10 , C07D409/12 , C07D471/04 , C07D401/04 , C07D403/12 , C07D405/12
Abstract: Preparation of 1,2,4-triazolin-3(2H)-ones of formula (I) comprises: (a) reaction of an amide of formula R NHC(=O)CH(R )R (V) with phosgene or thiophosgene (or a substitute for phosgene or thiophosgene) to give a compound of formula (VI); and (b) reaction of (VI) with a compound of formula QNHNHCOR (VII) or its acid addition salt in the presence of a base and finally an acid to give (I). Steps (a) and (b) are optionally conducted in a solvent and step (b) may be at an increased temperature. X = O or S; R = 2-8C alkoxyalkyl, 2-8C haloalkoxyalkyl, 3-8C alkoxycarbonylalkyl, 1-8C alkyl, 1-8C haloalkyl, 1-8C cyanoalkyl, 2-8C alkylthioalkyl, 2-8C alkylsulphinylalkyl, 2-8C alkylsulphonylalkyl, 7-8C arylalkyl (e.g. benzyl), 2-8C alkenyl, 2-8C haloalkenyl, 2-8C alkynyl or 2-8C haloalkynyl; aryl e.g. naphthyl or phenyl optionally substituted by one or more halo, 1-3C alkyl or OCH3; heteroaryl e.g. pyridine optionally substituted by halo; or a group of formula (a)-(c); R , R = H, 1-8C alkyl, 2-8C alkoxyalkyl, 7-8C aryloxyalkyl, 2 -8C alkylthioalkyl, 7-8C arylalkyl (e.g. benzyl), 2-8C alkenyl, 2-8C haloalkenyl, 2-8C alkynyl, 2-8C haloalkynyl, 1-8C cyanoalkyl, naphthyl or phenyl optionally mono- or di-substituted by 1-4C alkyl, 1-4C alkyloxyalkyl, halo or CF3; R , R may also be bonded to a 5-7-membered ring; Q =1-8C alkyl, 1-8C cycloalkyl, CH(Me)CONR R , 1-8C hydroxyalkyl, C(R R )nA or a group of formula (d); R = H, NHCO(1-8C alkyl), halo or NO2; R = H, NO2, NR R , COOR , halo or NHCO(1-4C alkyl); R = H, halo, 1-3C haloalkyl, benzyl or 1-4C alkoxycarbonyl; R = H, 1-4C alkyl or benzyl; R = H or 1-4C alkyl; R = 1-4C alkyl or phenyl optionally substituted by one or more halo or benzyl; A = benzoyl (optionally substituted by one or more halo), CO2R or a group of formula (e); R -R = H or halo; provided that if Q = group (d), then R = groups (a)-(c); R = H, SO2NH(1-6C alkyl), SO2NH(1-6C haloalkyl), SO2NHCOO(1-6C alkyl), SO2NHCO-phenyl optionally mono-, di- or tri-substituted by halo, 1-3C alkyl, 1-3C alkyloxy, 1-3C haloalkyl or 1-3C haloalkyloxy, SO2NHCO-B, 5-tetrazolyl or 1-4C alkoxycarbonyl; R = H, halo or 1-4C alkyl; R = H, halo, 1-4C alkyl or 1-4C alkyloxy; R = H, 1-5C alkyl, 1-5C haloalkyl, 1-5C alkoxy, 1-5C haloalkoxy, 1-8C cycloalkyl, 1-8C cyclohaloalkyl or 1-8C cyclohaloalkoxy; B = furan, thiophene or N-R pyrrole (all substituted by 2 R ); n = 1-4; D, E = CH=CH, N=CH or CH=N; Ar = phenyl optionally mono-, di- or tri-substituted by 1-4C alkyl, 1-4C alkyloxy, halo, trifluoromethyl, nitro, cyano or pyridyl optionally substituted by 1-4C alkyloxy.
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公开(公告)号：DE102010029399A1
公开(公告)日：2011-12-01
申请号：DE102010029399
申请日：2010-05-27
Applicant: EVONIK DEGUSSA GMBH
Inventor： KOBLER CHRISTOPH DR , HAEUSNER THOMAS , WECKBECKER CHRISTOPH DR
IPC: C07K5/12 , A23K1/16 , A61K31/495 , A61P1/00 , C07K5/06
Abstract: Die Erfindung betrifft Futtermitteladditive enthaltend mindestens ein Diketopiperazin mit der folgenden allgemeinen Formel IV oder ein Salz davon:wobei R1 und R2 unabhängig voneinander einen Aminosäurerest R darstellen (vorzugsweise in der L-Konfiguration) ausgewählt aus der Gruppe Methionin (R = -(CH2)2SCH3), Lysin (R = -(CH2)4NH2), Threonin (R = -CH(OH)(CH3)), Tryptophan (R = -indolyl), Histidin (R = -imidazoyl), Valin (R = -CH(CH3)2), Leucin (R = -CH2CH((CH3)2), Isoleucin (R = -CH(CH3)CH2CH3), Phenylalanin (R = -CH2Ph), Arginin (R = -(CH2)3NHC(=NH)CH2), Cystein (R = -CH2SH), wobei gegebenenfalls R1 gleich R2 sein kann; oder enthaltend mindestens eine Verbindung mit der folgenden allgemeinen Formel V oder ein Salz davon, wobei R1 und R2 wie oben definiert sind;sowie das Diketopiperazin selbst und ein Verfahren zu dessen Herstellung.
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公开(公告)号：DK1092700T3
公开(公告)日：2004-02-16
申请号：DK00121161
申请日：2000-09-29
Applicant: DEGUSSA
Inventor： NONGYUAN SHI DR , HUEBNER FRANK DR , DRAPAL BERND , PETER RAINER , KRILL STEFFEN DR , HUTHMACHER KLAUS DR , WECKBECKER CHRISTOPH DR
Abstract: A process for the preparation of unsaturated 4,5-alleneketones comprises reaction of a tertiary propargylalcohol with an alkenylalkylether or a ketal in the presence of an aliphatic sulfonic acid or salt. A process for the preparation of unsaturated 4,5-alleneketones (I) of formula (1) comprises reaction of a tertiary propargylalcohol of formula (2) with an alkenylalkylether of formula (3) or a ketal of formula (4) in the presence of an aliphatic sulfonic acid of formula (5) or sulfonic acid salt of formula (6). An Independent claim is included for a process for the preparation of unsaturated 3,5-dieneketones and their corresponding saturated ketones by isomerization or hydrogenation of 4,5-alleneketones (I) of formula (1). R -O-C(R )=CH-R (3), R SO3H (5), R SO3M (6) R , R = H, 1-20C alkyl, aryl or alkylaryl or R and R may combine to form a 5-6 membered ring; R , R = 1-4C alkyl; R ,R = 1-4C alkyl; R , R = halogen, 1-20C alkyl or cycloalkyl optionally substituted with halogen, R is additionally an optionally substituted aryl; and M = cation of an organic or inorganic base.
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Patent Agency Ranking
公开(公告)号：AT252533T
公开(公告)日：2003-11-15
申请号：AT00121161
申请日：2000-09-29
Applicant: DEGUSSA
Inventor： NONGYUAN SHI DR , HUEBNER FRANK DR , DRAPAL BERND , PETER RAINER , KRILL STEFFEN DR , HUTHMACHER KLAUS DR , WECKBECKER CHRISTOPH DR
Abstract: A process for the preparation of unsaturated 4,5-alleneketones comprises reaction of a tertiary propargylalcohol with an alkenylalkylether or a ketal in the presence of an aliphatic sulfonic acid or salt. A process for the preparation of unsaturated 4,5-alleneketones (I) of formula (1) comprises reaction of a tertiary propargylalcohol of formula (2) with an alkenylalkylether of formula (3) or a ketal of formula (4) in the presence of an aliphatic sulfonic acid of formula (5) or sulfonic acid salt of formula (6). An Independent claim is included for a process for the preparation of unsaturated 3,5-dieneketones and their corresponding saturated ketones by isomerization or hydrogenation of 4,5-alleneketones (I) of formula (1). R -O-C(R )=CH-R (3), R SO3H (5), R SO3M (6) R , R = H, 1-20C alkyl, aryl or alkylaryl or R and R may combine to form a 5-6 membered ring; R , R = 1-4C alkyl; R ,R = 1-4C alkyl; R , R = halogen, 1-20C alkyl or cycloalkyl optionally substituted with halogen, R is additionally an optionally substituted aryl; and M = cation of an organic or inorganic base.
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公开(公告)号：DE19505995A1
公开(公告)日：1996-08-22
申请号：DE19505995
申请日：1995-02-21
Applicant: DEGUSSA
Inventor： KNAUP GUENTER DR , RETZOW STEFAN DR , WECKBECKER CHRISTOPH DR
IPC: C07D331/04
Abstract: It is known that thietanones of general formula (I), in which R -R have the meanings given in the description, can be produced by the cyclisation, using hydrogen sulphide and a base, of the adducts obtainable by the addition of bromine to the ketones of general formula (III) given in the description. The invention obviates the need for toxic hydrogen sulphide and bromine by cyclising beta -oxosulphenyls of general formula (II), in which R -R have the meanings indicated in the description and X represents Cl, Br or J, in an organic solvent under the influence of a base. The invention also concerns intermediate products for the synthesis of dipeptide sweeteners.
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公开(公告)号：DE102010029276A1
公开(公告)日：2011-12-01
申请号：DE102010029276
申请日：2010-05-25
Applicant: EVONIK DEGUSSA GMBH
Inventor： WECKBECKER CHRISTOPH DR , RILEY KEVIN T
Abstract: Die Erfindung betrifft ein Verfahren zur Bekämpfung von Nematoden mit Salzen schwefelhaltiger Verbindungen.
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公开(公告)号：BR0004788A
公开(公告)日：2001-05-22
申请号：BR0004788
申请日：2000-10-11
Applicant: DEGUSSA
Inventor： SHI NONGYUAN DR , HUEBNER FRANK DR , DRAPAL BERND , PETER RAINER , KRILL STEFFEN DR , HUTHMACHER KLAUS DR , WECKBECKER CHRISTOPH DR
Abstract: A process for the preparation of unsaturated 4,5-alleneketones comprises reaction of a tertiary propargylalcohol with an alkenylalkylether or a ketal in the presence of an aliphatic sulfonic acid or salt. A process for the preparation of unsaturated 4,5-alleneketones (I) of formula (1) comprises reaction of a tertiary propargylalcohol of formula (2) with an alkenylalkylether of formula (3) or a ketal of formula (4) in the presence of an aliphatic sulfonic acid of formula (5) or sulfonic acid salt of formula (6). An Independent claim is included for a process for the preparation of unsaturated 3,5-dieneketones and their corresponding saturated ketones by isomerization or hydrogenation of 4,5-alleneketones (I) of formula (1). R -O-C(R )=CH-R (3), R SO3H (5), R SO3M (6) R , R = H, 1-20C alkyl, aryl or alkylaryl or R and R may combine to form a 5-6 membered ring; R , R = 1-4C alkyl; R ,R = 1-4C alkyl; R , R = halogen, 1-20C alkyl or cycloalkyl optionally substituted with halogen, R is additionally an optionally substituted aryl; and M = cation of an organic or inorganic base.
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公开(公告)号：DE19505933A1
公开(公告)日：1996-08-22
申请号：DE19505933
申请日：1995-02-21
Applicant: DEGUSSA
Inventor： DRAUZ KARLHEINZ PROF DR , KNAUP GUENTER DR , RETZOW STEFAN DR , SCHWARM MICHAEL DR , WECKBECKER CHRISTOPH DR
Abstract: The invention concerns a method of producing L-aspartyl-D-alanine-N-(thiethane-3-yl)-amides of general formula (I) by reacting D-alanine-thiethane amides of general formula (II) with oxazolidinone compounds of general formula (III) in an inert organic solvent, wherein R stands for H or a selectively separable protective group, R -R , independently of one another, are identical or different and stand for H or linear or branched C1-C4-alkyl, and R and R , independently of each another, are identical or different and stand for H, linear or branched C1-C4-alkyl, aryl or a group which activates the carbonyl group.
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