公开(公告)号：KR790000046B1

公开(公告)日：1979-02-28

申请号：KR730001943

申请日：1973-11-21

Applicant: HOECHST AG

Inventor： AUMUELLER W ,  HERR H ,  WEYER R ,  HITZEL V

Abstract: Title compds. [I; R = lower alkyl, lower alkoxy, halogen, - NH2, trifluoromethyl, acetyl or acylaminoalkyl (acyl = aliphatic, cycloaliphatic aromatic, heterocyclic carboxyl or carbaminic aicd, alkyl = having 1-4 carbon atoms) R1 = lower alkyl, cycloalkyl, cycloalkenyl, R2 = hydrogen or 5-7 atomic ring with R1 and neighboring nitrogen atom, R3 = alkyl having 1-3 carbon atoms , useful as hypoglycemic agent, were prepd. by reacting benzenesulfonyl-isourea ether with organic base.

公开(公告)号：KR800000452B1

公开(公告)日：1980-05-29

申请号：KR770003053

申请日：1977-12-27

Applicant: HOECHST AG

Inventor： BEYER R ,  AUMUELLER W ,  HITSEL V

IPC: C07D213/36

Abstract: Title compds.(I, R = C1-3 alkyl; R1 = C3-6 alkyl, C5-9 cycloalkyl, alkylcycloalky, cycloalkenyl, bicyclohetyl, bicycloheptenyl, nortricyclyl, benzyl), useful for lowering the blood sugar concentration, were prepd. by reaction of compds. II(Z =halogen, hydroxy, o-alkali metal group) with III in the presence of acid-condensation agent. Thus, N- 4-(β-N'-methyl-N'-2-pyridylureidoethyl)-benzenesulfonyl -N'-cyclohexylurea was prepd. by reacting 3.2 g 4-(β-N'methyl-N'-pyridyl -ureidoethyl_-benzenesulfinic acid with 1.6 g N-cyclohexyl-N'-hydroxyurea in 40ml dioxane at 60≦̸C for 2hrs.

公开(公告)号：KR790000180B1

公开(公告)日：1979-03-26

申请号：KR730001284

申请日：1973-08-07

Applicant: HOECHST AG

Inventor： WEYER R ,  HITZEL V ,  AUMUELLER W

Abstract: Benzenesulfonylureas (I; X = 2-quinolyl, 4-methyl-2-quinoyl, 2-pyridyl, R = Me, Et, Pr, R1 = alkyl, cycloalkyl, cycloalkylmethyl, Benzyl) were prepd. by heating 5.6g 4-(β-N'- 2-quinolyl-N'-methylureidoethyl)-benzenesulfonylmethylcarbamate and a mixt. of 1.lg cyclopentylamine and 75ml dioxane. When I was administered orally to rabbits at 10mg/kg, the blood sugar level was decreased by 4.3% after one hr, 49% after 24hr, and 18% after 47hr.

公开(公告)号：KR800000449B1

公开(公告)日：1980-05-29

申请号：KR770003049

申请日：1977-12-27

Applicant: HOECHST AG

Inventor： BEYER R ,  AUMUELLER W ,  HITSEL V

IPC: C07D213/36

Abstract: Title compds.(I, X = pyridyl, quinolyl, benzothiazolyl, etc. ; R = C1-3 alkyl; R1 = C3-6 alkyl, C5-9 cycloalkyl etc.), useful as hypoglycemic agent, were prepd. by treating compd. II with H2O. Thus, 2.4 g N-[4-β-N'-methyl-N'-2-pyridyl-ureid-oethyl) benzenesulfonyl -N' -cyclo hexylthiourea and 1.04 g dicyclohexyl-carbodiimide were treated at room temp. in 20 ml dioxane for several days and filtrated, following by adding 5ml H2O, and treated with steam to give N[4- (β-N'-methyl-N'-2-pyridyl-rureidoethyl)benzenesulfonyl -N'-cyclohexyl urea.

公开(公告)号：KR800000489B1

公开(公告)日：1980-06-04

申请号：KR770003050

申请日：1977-12-27

Applicant: HOECHST AG

Inventor： BEYER R ,  AUMUELLER W ,  HITSEL V ,  SCHMIDT F

IPC: C07D213/36

Abstract: Benzenesulfonyl ures and its salts(I; x = pyridyl, pyrimidinyl, quinolyl, benzothiazolyl, benzoxazolyl; R = C1-3 alkyl; R1 = C3-6 alkyl, C5-9 cycloalkenyl, cycloalkenyl, bicycloheptyl, bicycloheptenyl, adamantyl, benzyl), useful as hyperglycemic agent, were prepd. by oxidn. of benzenesulfinyl urea and benzenesulfenyl uresa. Thus, 3.4 g 4-(β-(N'-methyl-N'-pyridyl -ureidoethyl)-benzenesulfinic chloride and 1.7 g cyclohexyl urea were treaed at room temp. for 20 min in 20ml pyridine to give N-[4-(β-(N'-methyl-N'-pyridyl-ureidoethyl)-benzenesulfonyl urea.

公开(公告)号：KR800000450B1

公开(公告)日：1980-05-29

申请号：KR770003051

申请日：1977-12-27

Applicant: HOECHST AG

Inventor： BEYER R ,  AUMUELLER W ,  HITSEL V

IPC: C07D213/36

Abstract: Title compds.(I, X = pyridyl, quinolyl, benzothiazolyl; R = C1-3 alkyl; R1 = C3-6 alkyl, C5-9 cycloalkyl, cycloalkenyl, bicyclohetyl, adamantyl or benzyl) useful as hypoglycemic agent, were prepd. by adding a group(III, X and R are given) to benzenesulfonylurea(II). Thus, 1.8g N-methyl-N-2-pyridyl-carbamic chloride was added to a mixt. 3.25gN-[4-β-aminoethyl) -benzenesulfonyl -N' -cyclohexylurea and 1 g pyridine in DMF, and heated to steam to give N-[4- (β-N'-methyl-N'-2-pyridyl-ureidoethyl)-benzenesulfonyl -N'-cyclohexylurea.

公开(公告)号：US3790630A

公开(公告)日：1974-02-05

申请号：US3790630D

申请日：1969-07-28

Applicant: HOECHST AG

Inventor： SCHMIDT F ,  WEBER H ,  MUTH K ,  WEYER R ,  AUMUELLER W

IPC: C07C311/58 ,  C07C303/36 ,  C07C303/38 ,  C07C311/59 ,  C07D233/96 ,  C07D333/20 ,  C07C127/00

CPC classification number: C07D233/96 ,  C07C303/36 ,  C07C2601/16 ,  Y10S514/866 ,  C07C311/59

Abstract: BENZENESULFONYL-UREAS OF THE FORMULA

1-(X-CO-NH-CH2-CH2-),4-(2-CYCLOHEXEN-1-YL-NH-CO-NH-SO2-)

BENZENE

WHICH IN THE FREE FROM OR IN THE FORM OF THEIR SALTS HAVE BLOOD SUGAR LOWERING PROPERTIES AND ARE DISTINGUISHED BY A STRONG AND LONG-LASTING HYPOGLYCEMIC ACTION. IN THE FORMULA X REPRESENTS (R-O-),Z-PHENYL OR 3-(R-O-),5-Z''-THIEN-2-YL WHEREIN R STANDS FOR AN ALKYL GROUP HAVING 1 TO 4 CARBON ATOMS, Z STANDS FOR A HALOGEN ATOM, AN ALKYL OR ALKOXY GROUP BOTH HAVING 1 TO 4 CARBON ATOMS, AND Z'' STANDS FOR A HALOGEN ATOM OR AN ALKYL GROUP HAVING 1 TO 4 CARBON ATOMS.

公开(公告)号：US3813398A

公开(公告)日：1974-05-28

申请号：US14974671

申请日：1971-06-03

Applicant: HOECHST AG

Inventor： AUMUELLER W ,  WEYER R ,  HEERDT R

IPC: A61K31/175 ,  A61K31/47 ,  A61K31/64 ,  C07D215/48 ,  C07D33/00

CPC classification number: A61K31/47 ,  C07D215/48

Abstract: HYPOGLYCEMICALLY ACTIIVE BENZENESULFONYL - SEMICARBAZIDES OF THE FORMULA

1-((X-QUINOL-8-YL)-CO-NH-Y-),4-(R-NH-CO-NH-SO2-),Z-

BENZENE

WHEREIN X IS HYDROGEN, CHLORINE, BROMINE, METYL OR METHOXY, Y IS -CH(CH3)-CH3-, PREFERABLY

-CH2-CH2-,

Z IS HYDROGEN OR A HYDROCARBON RADICAL OF 1 OR 2 CARBON ATOMS, WHICH FORMS TOGETHER WITH A 5- OR 6-MEMBERED RING, R IS ALKYLENE-IMINO OF 3 TO 7 CARBON ATOMS IN THE RING WHICH MAY BE UNSATURATED OR SUBSTITUTED BY 1 OR 2 METHYL OR LOWER ALKYL OR METHOXY, PENTAMETHYLENIMINO SUBSTITUTED BY ENDOALKYLENE OF 1 TO 3 CARBON ATOMS, HEXAMETHYLENE-IMINO SUBSTITUTED BY ENDOETHYLENE IN B-EPOSITIONS, TETRAHYDRO-ISO-INDOLINE, 4,7 - ENDOALKYLENE-HEXAHYDRO- OR -TETRAHYDRO-ISO-INDOLINE, THE ENDOALKYLENE CONTAINING 1 OR 2 CARBON ATOMS AND THE DOUBLE BOND OF THE TETRAHYDRO COMPOUND BEING IN 5,6 POSITION, AND THE SALTS THEREOF.

公开(公告)号：KR800000944B1

公开(公告)日：1980-09-15

申请号：KR770003047

申请日：1977-12-27

Applicant: HOECHST AG

Inventor： HITZEL V ,  WEYER R ,  AUMUELLER W

IPC: C07D239/26 ,  C07C311/58 ,  C07C311/59 ,  C07C311/60 ,  C07D213/75 ,  C07D215/38 ,  C07D239/42 ,  C07D263/58 ,  C07D277/82 ,  C07D213/02 ,  C07D215/02

Abstract: The title compds. (I; X=pyridyl, pyrimidinyl, quinolyl, benzthiazolyl, benzoxazolyl; R=C1-3 alkyl; R1=C3-6 alkyl, C5-9 cycloalkyl, alkylcycloalkyl, cycloalkenyl, bicycloheptyl, bicycloheptenyl, ada-antyl, benzyl) were prepd. by hydrolysis of II (A=urea substitutent such as isourea ether). Thus, N-4-(-(N'-methvl-N'-2-pyridyl-ureido)-ethyl) benzenesulfonyl-N'-cyclohexyl thiourea was treated with HgO, COCl2 and conc. HCl to geve I(X=pyridyl; R=Me; R1=C6H11) which at 10mg/kg orally in rabbits decreased the blood sugar level by 43%, after 1 hr, 49% after 24 hr and 18% after 48 hr

公开(公告)号：KR800000488B1

公开(公告)日：1980-06-04

申请号：KR770003048

申请日：1977-12-27

Applicant: HOECHST AG

Inventor： BEYER R ,  AUMUELLER W ,  HITSEL V ,  SCHMIDT F

IPC: C07D213/36

Abstract: Benzenesulfonyl ureas (I; X = pyridyl, pyrimidinyl, quinolyl, benzothiazolyl, benzoxazolyl; R = C1-3 alkyl; R1 = C3-6 alkyl, C5-9 cycloalkenyl, cycloalkeny, bicycloheptyl, adamantyl, benzyl), useful as hyperglycemic agent, were prepd. by substituting S with O from II-substituted benzenesulfonylthiourea. Thus, 5 g N-[4-(β-(N'-methyl-N'-pyridyl-ureido)-ethyl) benzenesulfonyl -N'-cyclohexyl-thiourea(4(β-