NO312896B1 - Nye 4-(1-piperazinyl)benzosyrederivater, fremgangsmåte for fremstilling derav, samt farmasöytiske preparater som omfatter dem - Google Patents

Nye 4-(1-piperazinyl)benzosyrederivater, fremgangsmåte for fremstilling derav, samt farmasöytiske preparater som omfatter dem Download PDF

Info

Publication number: NO312896B1
Authority: NO; Norway
Prior art keywords: general formula; compound; group; benzoic acid; piperazinyl
Prior art date: 1996-12-18

Application number

NO19992968A

Other languages

English (en)

Norwegian (no)

Other versions

NO992968D0 (no

NO992968L (no

Inventor

Gerard Moinet

Gerard Botton

Liliane Doare

Micheline Kergoat

Didier Messangeau

Original Assignee

Merck Patent Gmbh

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-12-18

Filing date

1999-06-17

Publication date

2002-07-15

1999-06-17 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

1999-06-17 Publication of NO992968D0 publication Critical patent/NO992968D0/no

1999-08-17 Publication of NO992968L publication Critical patent/NO992968L/no

2002-07-15 Publication of NO312896B1 publication Critical patent/NO312896B1/no

Links

238000002360 preparation method Methods 0.000 title description 6
238000000034 method Methods 0.000 title description 3
IAGYKSQGLCAAAD-UHFFFAOYSA-N 4-piperazin-1-ylbenzoic acid Chemical class C1=CC(C(=O)O)=CC=C1N1CCNCC1 IAGYKSQGLCAAAD-UHFFFAOYSA-N 0.000 title description 2
239000008194 pharmaceutical composition Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 37
150000003839 salts Chemical class 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
-1 tetrahydroquinolyl group Chemical group 0.000 claims description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
239000000825 pharmaceutical preparation Substances 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
WQRHBWPFLIMKBV-UHFFFAOYSA-N 4-[4-[2-(2,6-dimethylanilino)-2-oxoethyl]piperazin-1-yl]benzoic acid Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(C=2C=CC(=CC=2)C(O)=O)CC1 WQRHBWPFLIMKBV-UHFFFAOYSA-N 0.000 claims description 2
DCIMQUKHQAATIV-UHFFFAOYSA-N 4-[4-[2-[2,6-di(propan-2-yl)anilino]-2-oxoethyl]piperazin-1-yl]benzoic acid Chemical compound CC(C)C1=CC=CC(C(C)C)=C1NC(=O)CN1CCN(C=2C=CC(=CC=2)C(O)=O)CC1 DCIMQUKHQAATIV-UHFFFAOYSA-N 0.000 claims description 2
KXTCDVCBTFRBNJ-UHFFFAOYSA-N 4-[4-[2-oxo-2-(n-propan-2-ylanilino)ethyl]piperazin-1-yl]benzoic acid Chemical group C=1C=CC=CC=1N(C(C)C)C(=O)CN(CC1)CCN1C1=CC=C(C(O)=O)C=C1 KXTCDVCBTFRBNJ-UHFFFAOYSA-N 0.000 claims description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
150000004982 aromatic amines Chemical class 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
239000012453 solvate Substances 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
239000007787 solid Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 5
239000002253 acid Substances 0.000 description 5
241001465754 Metazoa Species 0.000 description 4
206010012601 diabetes mellitus Diseases 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
ZFDXBBFPJMOXLX-UHFFFAOYSA-N 4-[4-[2-(4-chloroanilino)-2-oxoethyl]piperazin-1-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1CCN(CC(=O)NC=2C=CC(Cl)=CC=2)CC1 ZFDXBBFPJMOXLX-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
239000002775 capsule Substances 0.000 description 3
125000004494 ethyl ester group Chemical group 0.000 description 3
239000000243 solution Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
208000001072 type 2 diabetes mellitus Diseases 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
UDRCRMHFHHTVSN-UHFFFAOYSA-N 2-chloro-n-(4-chlorophenyl)acetamide Chemical compound ClCC(=O)NC1=CC=C(Cl)C=C1 UDRCRMHFHHTVSN-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 2
230000003178 anti-diabetic effect Effects 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
OQEHTFFLOHTFSB-UHFFFAOYSA-N ethyl 4-piperazin-1-ylbenzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N1CCNCC1 OQEHTFFLOHTFSB-UHFFFAOYSA-N 0.000 description 2
238000011835 investigation Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
239000000203 mixture Substances 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000012360 testing method Methods 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
CUGDYSSBTWBKII-LXGUWJNJSA-N (2r,3r,4r,5s)-6-(dimethylamino)hexane-1,2,3,4,5-pentol Chemical compound CN(C)C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO CUGDYSSBTWBKII-LXGUWJNJSA-N 0.000 description 1
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
229920000881 Modified starch Polymers 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
ZSJLQEPLLKMAKR-UHFFFAOYSA-N Streptozotocin Natural products O=NN(C)C(=O)NC1C(O)OC(CO)C(O)C1O ZSJLQEPLLKMAKR-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
WPYMKLBDIGXBTP-VQEHIDDOSA-N benzoic acid Chemical compound OC(=O)C1=CC=C[13CH]=C1 WPYMKLBDIGXBTP-VQEHIDDOSA-N 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000012043 crude product Substances 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229940050411 fumarate Drugs 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000644 isotonic solution Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical class [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
239000004137 magnesium phosphate Substances 0.000 description 1
235000010994 magnesium phosphates Nutrition 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
229940049920 malate Drugs 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
239000000155 melt Substances 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019426 modified starch Nutrition 0.000 description 1
229940105631 nembutal Drugs 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical class [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000002904 solvent Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 1
229960001052 streptozocin Drugs 0.000 description 1
239000000126 substance Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/08—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms with acylated ring nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Diabetes (AREA)
General Chemical & Material Sciences (AREA)
Emergency Medicine (AREA)
Hematology (AREA)
Obesity (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Endocrinology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Furan Compounds (AREA)

NO19992968A 1996-12-18 1999-06-17 Nye 4-(1-piperazinyl)benzosyrederivater, fremgangsmåte for fremstilling derav, samt farmasöytiske preparater som omfatter dem NO312896B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9615588A FR2757158B1 (fr)	1996-12-18	1996-12-18	Nouveaux derives d'acide 4-(1-piperazinyl) benzoique, leur procede de preparation et leurs applications therapeutiques
PCT/EP1997/007046 WO1998027078A1 (en)	1996-12-18	1997-12-15	New 4-(1-piperazinyl)benzoic acid derivatives, process for preparing them and their therapeutic applications

Publications (3)

Publication Number	Publication Date
NO992968D0 NO992968D0 (no)	1999-06-17
NO992968L NO992968L (no)	1999-08-17
NO312896B1 true NO312896B1 (no)	2002-07-15

Family

ID=9498818

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19992968A NO312896B1 (no)	1996-12-18	1999-06-17	Nye 4-(1-piperazinyl)benzosyrederivater, fremgangsmåte for fremstilling derav, samt farmasöytiske preparater som omfatter dem

Country Status (26)

Country	Link
US (1)	US6281215B1 (da)
EP (1)	EP0937054B1 (da)
JP (1)	JP2001506645A (da)
KR (1)	KR20000069544A (da)
CN (1)	CN1073102C (da)
AR (1)	AR013889A1 (da)
AT (1)	ATE218558T1 (da)
AU (1)	AU726640B2 (da)
BR (1)	BR9713587A (da)
CA (1)	CA2275346A1 (da)
CZ (1)	CZ218999A3 (da)
DE (1)	DE69713128T2 (da)
DK (1)	DK0937054T3 (da)
ES (1)	ES2178039T3 (da)
FR (1)	FR2757158B1 (da)
HU (1)	HUP0000586A3 (da)
ID (1)	ID23671A (da)
NO (1)	NO312896B1 (da)
PL (1)	PL334187A1 (da)
PT (1)	PT937054E (da)
RU (1)	RU2178786C2 (da)
SK (1)	SK282841B6 (da)
TR (1)	TR199901367T2 (da)
UA (1)	UA56206C2 (da)
WO (1)	WO1998027078A1 (da)
ZA (1)	ZA9711329B (da)

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Publication number	Priority date	Publication date	Assignee	Title
FR2763334A1 (fr) *	1997-05-13	1998-11-20	Lipha	Derives anthraniliques
GB0013346D0 (en) *	2000-06-01	2000-07-26	Glaxo Group Ltd	Therapeutic benzamide derivatives
US6476046B1 (en)	2000-12-04	2002-11-05	Sepracor, Inc.	Diazabicyclo[4.3.0]nonanes, and methods of use thereof
CN101417988B (zh) *	2007-10-24	2011-04-27	山东轩竹医药科技有限公司	双胍哌嗪类二肽酰肽酶ⅳ抑制剂
CN101781273B (zh) *	2009-01-21	2012-07-04	山东轩竹医药科技有限公司	含有胍基的二肽酰肽酶ⅳ抑制剂

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FR2346011A1 (fr) *	1976-02-02	1977-10-28	Orsymonde	Acetanilido-piperazines
DE3139970A1 (de) *	1981-10-08	1983-04-28	Boehringer Mannheim Gmbh, 6800 Mannheim	Neue carbonsaeurederivate, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel
US5364849A (en) *	1989-04-22	1994-11-15	John Wyeth & Brother, Limited	1-[3 or 4-[1-[4-piperazinyl]]-2 arylpropionyl or butryl]-heterocyclic derivatives
FR2693722B1 (fr) *	1992-07-16	1994-10-14	Meram Lab	Dérivés de la N-cycloalkylpipérazine, procédé d'obtention et compositions pharmaceutiques les contenant.
GB9221931D0 (en) *	1992-10-17	1992-12-02	Wyeth John & Brother Ltd	Piperazine derivatives
FR2707984B1 (fr) *	1993-07-23	1995-09-01	Adir	Nouvelles pipérazines substituées, leur procédé de préparation et les compositions les contenant.
US5607936A (en) *	1994-09-30	1997-03-04	Merck & Co., Inc.	Substituted aryl piperazines as neurokinin antagonists
IT1278960B1 (it) *	1995-02-24	1997-12-02	Elitas S N C Di Belluzzi Lino	Macchina tamponatrice per impregnare superficialmente pelli o simili.
US5723475A (en) *	1995-02-28	1998-03-03	Suntory Limited	Arylpiperidine and arylpiperazine derivatives and medicament containing the same

1996
- 1996-12-18 FR FR9615588A patent/FR2757158B1/fr not_active Expired - Fee Related
1997
- 1997-12-15 DE DE69713128T patent/DE69713128T2/de not_active Expired - Fee Related
- 1997-12-15 PT PT97953824T patent/PT937054E/pt unknown
- 1997-12-15 TR TR1999/01367T patent/TR199901367T2/xx unknown
- 1997-12-15 AT AT97953824T patent/ATE218558T1/de not_active IP Right Cessation
- 1997-12-15 HU HU0000586A patent/HUP0000586A3/hu unknown
- 1997-12-15 ES ES97953824T patent/ES2178039T3/es not_active Expired - Lifetime
- 1997-12-15 KR KR1019997005478A patent/KR20000069544A/ko not_active Ceased
- 1997-12-15 SK SK785-99A patent/SK282841B6/sk unknown
- 1997-12-15 EP EP97953824A patent/EP0937054B1/en not_active Expired - Lifetime
- 1997-12-15 WO PCT/EP1997/007046 patent/WO1998027078A1/en not_active Ceased
- 1997-12-15 UA UA99074128A patent/UA56206C2/uk unknown
- 1997-12-15 CZ CZ992189A patent/CZ218999A3/cs unknown
- 1997-12-15 CA CA002275346A patent/CA2275346A1/en not_active Abandoned
- 1997-12-15 JP JP52730398A patent/JP2001506645A/ja active Pending
- 1997-12-15 DK DK97953824T patent/DK0937054T3/da active
- 1997-12-15 ID IDW990539A patent/ID23671A/id unknown
- 1997-12-15 US US09/331,155 patent/US6281215B1/en not_active Expired - Fee Related
- 1997-12-15 BR BR9713587-9A patent/BR9713587A/pt unknown
- 1997-12-15 CN CN97181700A patent/CN1073102C/zh not_active Expired - Fee Related
- 1997-12-15 RU RU99115481/04A patent/RU2178786C2/ru not_active IP Right Cessation
- 1997-12-15 PL PL97334187A patent/PL334187A1/xx unknown
- 1997-12-15 AU AU57582/98A patent/AU726640B2/en not_active Ceased
- 1997-12-17 ZA ZA9711329A patent/ZA9711329B/xx unknown
- 1997-12-18 AR ARP970105971A patent/AR013889A1/es unknown
1999
- 1999-06-17 NO NO19992968A patent/NO312896B1/no unknown

Also Published As

Publication number	Publication date
TR199901367T2 (xx)	1999-10-21
DK0937054T3 (da)	2002-09-16
JP2001506645A (ja)	2001-05-22
AU726640B2 (en)	2000-11-16
DE69713128D1 (de)	2002-07-11
HUP0000586A3 (en)	2002-10-28
ID23671A (id)	2000-05-11
AU5758298A (en)	1998-07-15
AR013889A1 (es)	2001-01-31
SK78599A3 (en)	2000-03-13
NO992968D0 (no)	1999-06-17
UA56206C2 (uk)	2003-05-15
CA2275346A1 (en)	1998-06-25
KR20000069544A (ko)	2000-11-25
FR2757158B1 (fr)	1999-04-02
FR2757158A1 (fr)	1998-06-19
CZ218999A3 (cs)	1999-09-15
DE69713128T2 (de)	2003-03-20
WO1998027078A1 (en)	1998-06-25
CN1073102C (zh)	2001-10-17
US6281215B1 (en)	2001-08-28
HUP0000586A2 (hu)	2001-04-28
ZA9711329B (en)	1998-06-24
ATE218558T1 (de)	2002-06-15
RU2178786C2 (ru)	2002-01-27
PL334187A1 (en)	2000-02-14
CN1245494A (zh)	2000-02-23
NO992968L (no)	1999-08-17
PT937054E (pt)	2002-11-29
EP0937054A1 (en)	1999-08-25
BR9713587A (pt)	2000-04-04
SK282841B6 (sk)	2002-12-03
EP0937054B1 (en)	2002-06-05
ES2178039T3 (es)	2002-12-16

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NO312896B1 (no)	2002-07-15	Nye 4-(1-piperazinyl)benzosyrederivater, fremgangsmåte for fremstilling derav, samt farmasöytiske preparater som omfatter dem
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