UA71591C2 - 4-(aminomethyl)piperidine benzamide derivatives, pharmaceutical composition based thereon, a process for preparing thereof (variants), an intermediary compound and a method for preparing thereof - Google Patents

4-(aminomethyl)piperidine benzamide derivatives, pharmaceutical composition based thereon, a process for preparing thereof (variants), an intermediary compound and a method for preparing thereof Download PDF

Info

Publication number: UA71591C2
Authority: UA; Ukraine
Prior art keywords: formula; alkyl; compound; group; hydrogen
Prior art date: 1998-12-22

Application number

UA2001064399A

Other languages

English (en)

Ukrainian (uk)

Inventor

Jean-Paul Rene Mari An Bosmans

Klein Michel Anna Joseph De

Henrikus Jacobus Maria Guisen

Original Assignee

Janssen Pharmaceutica Nv

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.)

1998-12-22

Filing date

1999-12-14

Publication date

2004-12-15

1999-12-14 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2004-12-15 Publication of UA71591C2 publication Critical patent/UA71591C2/uk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 242
238000000034 method Methods 0.000 title claims abstract description 25
239000008194 pharmaceutical composition Substances 0.000 title claims description 7
238000004519 manufacturing process Methods 0.000 title description 5
SZVHQUMEPYZZTA-UHFFFAOYSA-N benzamide;piperidin-4-ylmethanamine Chemical class NCC1CCNCC1.NC(=O)C1=CC=CC=C1 SZVHQUMEPYZZTA-UHFFFAOYSA-N 0.000 title 1
239000001257 hydrogen Substances 0.000 claims abstract description 64
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 64
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 39
150000003839 salts Chemical class 0.000 claims abstract description 34
239000002253 acid Substances 0.000 claims abstract description 24
150000002431 hydrogen Chemical group 0.000 claims abstract description 24
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 20
125000003386 piperidinyl group Chemical group 0.000 claims abstract description 20
125000003118 aryl group Chemical group 0.000 claims abstract description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
125000004193 piperazinyl group Chemical group 0.000 claims abstract description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 46
238000006243 chemical reaction Methods 0.000 claims description 42
239000011541 reaction mixture Substances 0.000 claims description 39
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 29
150000004820 halides Chemical class 0.000 claims description 28
125000003277 amino group Chemical group 0.000 claims description 25
125000006239 protecting group Chemical group 0.000 claims description 20
125000001424 substituent group Chemical group 0.000 claims description 20
239000003054 catalyst Substances 0.000 claims description 17
239000002585 base Substances 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 9
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 8
239000012634 fragment Substances 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 6
239000012458 free base Substances 0.000 claims description 6
239000012442 inert solvent Substances 0.000 claims description 6
229910052740 iodine Inorganic materials 0.000 claims description 6
125000003373 pyrazinyl group Chemical group 0.000 claims description 6
125000002098 pyridazinyl group Chemical group 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 5
238000005804 alkylation reaction Methods 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
229940002612 prodrug Drugs 0.000 claims description 5
239000000651 prodrug Substances 0.000 claims description 5
238000010992 reflux Methods 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
238000009835 boiling Methods 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
229940126601 medicinal product Drugs 0.000 claims description 2
150000003512 tertiary amines Chemical class 0.000 claims description 2
BQNIFTLCQBTDOH-UHFFFAOYSA-N 2-[4-(aminomethyl)piperidin-1-yl]benzamide Chemical class C1CC(CN)CCN1C1=CC=CC=C1C(N)=O BQNIFTLCQBTDOH-UHFFFAOYSA-N 0.000 claims 3
240000008415 Lactuca sativa Species 0.000 claims 1
150000001299 aldehydes Chemical class 0.000 claims 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
150000002576 ketones Chemical class 0.000 claims 1
235000012045 salad Nutrition 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 77
-1 oxoC5-6cycloalkyl Chemical group 0.000 abstract description 49
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 13
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 6
239000003814 drug Substances 0.000 abstract description 5
229910052760 oxygen Inorganic materials 0.000 abstract description 3
208000018522 Gastrointestinal disease Diseases 0.000 abstract description 2
238000009472 formulation Methods 0.000 abstract description 2
125000004356 hydroxy functional group Chemical group O* 0.000 abstract 2
125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 abstract 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 abstract 1
125000000815 N-oxide group Chemical group 0.000 abstract 1
125000001475 halogen functional group Chemical group 0.000 abstract 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
229910052717 sulfur Inorganic materials 0.000 abstract 1
RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 1
239000000543 intermediate Substances 0.000 description 150
239000002904 solvent Substances 0.000 description 57
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 40
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
150000003254 radicals Chemical class 0.000 description 34
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 27
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
239000000243 solution Substances 0.000 description 25
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
239000003480 eluent Substances 0.000 description 22
239000000741 silica gel Substances 0.000 description 20
229910002027 silica gel Inorganic materials 0.000 description 20
238000004587 chromatography analysis Methods 0.000 description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
239000012044 organic layer Substances 0.000 description 16
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 15
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
108010037444 diisopropylglutathione ester Proteins 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
239000000706 filtrate Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000002552 dosage form Substances 0.000 description 8
238000005984 hydrogenation reaction Methods 0.000 description 8
239000007788 liquid Substances 0.000 description 8
239000000796 flavoring agent Substances 0.000 description 7
238000002347 injection Methods 0.000 description 7
239000007924 injection Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
230000002159 abnormal effect Effects 0.000 description 6
229910000085 borane Inorganic materials 0.000 description 6
201000006549 dyspepsia Diseases 0.000 description 6
235000019441 ethanol Nutrition 0.000 description 6
235000003599 food sweetener Nutrition 0.000 description 6
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
230000035945 sensitivity Effects 0.000 description 6
239000003765 sweetening agent Substances 0.000 description 6
239000003826 tablet Substances 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
230000009286 beneficial effect Effects 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 5
239000002775 capsule Substances 0.000 description 5
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 5
235000013355 food flavoring agent Nutrition 0.000 description 5
239000000047 product Substances 0.000 description 5
239000012279 sodium borohydride Substances 0.000 description 5
229910000033 sodium borohydride Inorganic materials 0.000 description 5
239000007858 starting material Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
241000396377 Tranes Species 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
230000003042 antagnostic effect Effects 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
235000019634 flavors Nutrition 0.000 description 4
230000002496 gastric effect Effects 0.000 description 4
230000007661 gastrointestinal function Effects 0.000 description 4
239000011521 glass Substances 0.000 description 4
208000024798 heartburn Diseases 0.000 description 4
230000000968 intestinal effect Effects 0.000 description 4
208000002551 irritable bowel syndrome 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
239000000843 powder Substances 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
206010010774 Constipation Diseases 0.000 description 3
206010012735 Diarrhoea Diseases 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
206010017943 Gastrointestinal conditions Diseases 0.000 description 3
206010020651 Hyperkinesia Diseases 0.000 description 3
208000000269 Hyperkinesis Diseases 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
208000002193 Pain Diseases 0.000 description 3
241000700159 Rattus Species 0.000 description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
238000005810 carbonylation reaction Methods 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
210000001035 gastrointestinal tract Anatomy 0.000 description 3
235000012907 honey Nutrition 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052759 nickel Inorganic materials 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
229940081974 saccharin Drugs 0.000 description 3
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000375 suspending agent Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
239000006188 syrup Substances 0.000 description 3
KWEISZMWJPDOFR-UHFFFAOYSA-N (1-benzyl-3,6-dihydro-2h-pyridin-4-yl)methanol Chemical compound C1CC(CO)=CCN1CC1=CC=CC=C1 KWEISZMWJPDOFR-UHFFFAOYSA-N 0.000 description 2
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
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 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
241000566113 Branta sandvicensis Species 0.000 description 2
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
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206010015137 Eructation Diseases 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
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NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
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FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
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KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
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238000010521 absorption reaction Methods 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000000654 additive Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
239000002168 alkylating agent Substances 0.000 description 2
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239000008365 aqueous carrier Substances 0.000 description 2
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239000012298 atmosphere Substances 0.000 description 2
208000027687 belching Diseases 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
239000000292 calcium oxide Substances 0.000 description 2
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
229910002091 carbon monoxide Inorganic materials 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
229940008406 diethyl sulfate Drugs 0.000 description 2
125000000532 dioxanyl group Chemical group 0.000 description 2
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238000002474 experimental method Methods 0.000 description 2
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239000008103 glucose Substances 0.000 description 2
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 2
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
LFKYBJLFJOOKAE-UHFFFAOYSA-N imidazol-2-ylidenemethanone Chemical class O=C=C1N=CC=N1 LFKYBJLFJOOKAE-UHFFFAOYSA-N 0.000 description 2
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GAGALXYDHSHHCD-RKDXNWHRSA-N tert-butyl (3s,4r)-4-(aminomethyl)-3-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[C@H](CN)[C@H](O)C1 GAGALXYDHSHHCD-RKDXNWHRSA-N 0.000 description 1
GAGALXYDHSHHCD-DTWKUNHWSA-N tert-butyl (3s,4s)-4-(aminomethyl)-3-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[C@@H](CN)[C@H](O)C1 GAGALXYDHSHHCD-DTWKUNHWSA-N 0.000 description 1
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230000017105 transposition Effects 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/10—Laxatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Nutrition Science (AREA)
Hospice & Palliative Care (AREA)
Otolaryngology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

UA2001064399A 1998-12-22 1999-12-14 4-(aminomethyl)piperidine benzamide derivatives, pharmaceutical composition based thereon, a process for preparing thereof (variants), an intermediary compound and a method for preparing thereof UA71591C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP98204411		1998-12-22
PCT/EP1999/010064 WO2000037461A1 (en)	1998-12-22	1999-12-14	4-(aminomethyl)-piperidine benzamides for treating gastrointestinal disorders

Publications (1)

Publication Number	Publication Date
UA71591C2 true UA71591C2 (en)	2004-12-15

Family

ID=8234539

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2001064399A UA71591C2 (en)	1998-12-22	1999-12-14	4-(aminomethyl)piperidine benzamide derivatives, pharmaceutical composition based thereon, a process for preparing thereof (variants), an intermediary compound and a method for preparing thereof

Country Status (34)

Country	Link
US (2)	US6544997B1 (id)
EP (1)	EP1140915B1 (id)
JP (1)	JP4615725B2 (id)
KR (1)	KR100633680B1 (id)
CN (1)	CN1150190C (id)
AR (1)	AR024240A1 (id)
AT (1)	ATE297917T1 (id)
AU (1)	AU770397B2 (id)
BG (1)	BG64953B1 (id)
BR (1)	BR9916491A (id)
CA (1)	CA2355857C (id)
CZ (1)	CZ300851B6 (id)
DE (1)	DE69925865T2 (id)
DK (1)	DK1140915T3 (id)
EA (1)	EA003608B1 (id)
EE (1)	EE200100335A (id)
ES (1)	ES2245131T3 (id)
HK (1)	HK1039114B (id)
HR (1)	HRP20010445A2 (id)
HU (1)	HUP0104838A3 (id)
ID (1)	ID28953A (id)
IL (1)	IL143858A (id)
MY (1)	MY121852A (id)
NO (1)	NO321324B1 (id)
NZ (1)	NZ512871A (id)
PL (1)	PL197409B1 (id)
PT (1)	PT1140915E (id)
SI (1)	SI1140915T1 (id)
SK (1)	SK285829B6 (id)
TR (1)	TR200101962T2 (id)
TW (1)	TW570920B (id)
UA (1)	UA71591C2 (id)
WO (1)	WO2000037461A1 (id)
ZA (1)	ZA200105135B (id)

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1999
- 1999-12-03 TW TW088121125A patent/TW570920B/zh not_active IP Right Cessation
- 1999-12-14 TR TR2001/01962T patent/TR200101962T2/xx unknown
- 1999-12-14 IL IL14385899A patent/IL143858A/xx not_active IP Right Cessation
- 1999-12-14 BR BR9916491-4A patent/BR9916491A/pt not_active Application Discontinuation
- 1999-12-14 EA EA200100710A patent/EA003608B1/ru not_active IP Right Cessation
- 1999-12-14 SK SK859-2001A patent/SK285829B6/sk not_active IP Right Cessation
- 1999-12-14 HU HU0104838A patent/HUP0104838A3/hu unknown
- 1999-12-14 DK DK99967956T patent/DK1140915T3/da active
- 1999-12-14 HK HK02100161.1A patent/HK1039114B/en not_active IP Right Cessation
- 1999-12-14 WO PCT/EP1999/010064 patent/WO2000037461A1/en not_active Ceased
- 1999-12-14 AU AU24328/00A patent/AU770397B2/en not_active Ceased
- 1999-12-14 EP EP99967956A patent/EP1140915B1/en not_active Expired - Lifetime
- 1999-12-14 JP JP2000589532A patent/JP4615725B2/ja not_active Expired - Fee Related
- 1999-12-14 US US09/857,905 patent/US6544997B1/en not_active Expired - Lifetime
- 1999-12-14 KR KR1020017005055A patent/KR100633680B1/ko not_active Expired - Fee Related
- 1999-12-14 CN CNB998147699A patent/CN1150190C/zh not_active Expired - Fee Related
- 1999-12-14 UA UA2001064399A patent/UA71591C2/uk unknown
- 1999-12-14 NZ NZ512871A patent/NZ512871A/xx unknown
- 1999-12-14 HR HR20010445A patent/HRP20010445A2/hr not_active Application Discontinuation
- 1999-12-14 ES ES99967956T patent/ES2245131T3/es not_active Expired - Lifetime
- 1999-12-14 PT PT99967956T patent/PT1140915E/pt unknown
- 1999-12-14 ID IDW00200101336A patent/ID28953A/id unknown
- 1999-12-14 AT AT99967956T patent/ATE297917T1/de not_active IP Right Cessation
- 1999-12-14 EE EEP200100335A patent/EE200100335A/xx unknown
- 1999-12-14 SI SI9930822T patent/SI1140915T1/sl unknown
- 1999-12-14 CZ CZ20012117A patent/CZ300851B6/cs not_active IP Right Cessation
- 1999-12-14 DE DE69925865T patent/DE69925865T2/de not_active Expired - Lifetime
- 1999-12-14 PL PL348417A patent/PL197409B1/pl unknown
- 1999-12-14 CA CA002355857A patent/CA2355857C/en not_active Expired - Fee Related
- 1999-12-17 MY MYPI99005534A patent/MY121852A/en unknown
- 1999-12-21 AR ARP990106644A patent/AR024240A1/es active IP Right Grant
2001
- 2001-06-07 BG BG105571A patent/BG64953B1/bg unknown
- 2001-06-08 NO NO20012858A patent/NO321324B1/no not_active IP Right Cessation
- 2001-06-21 ZA ZA200105135A patent/ZA200105135B/en unknown
2003
- 2003-01-29 US US10/353,307 patent/US7205410B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
HK1039114A1 (en)	2002-04-12
KR20010080293A (ko)	2001-08-22
SK8592001A3 (en)	2002-02-05
TR200101962T2 (tr)	2002-04-22
BG64953B1 (bg)	2006-10-31
ATE297917T1 (de)	2005-07-15
ES2245131T3 (es)	2005-12-16
CA2355857C (en)	2008-10-28
IL143858A0 (en)	2002-04-21
PT1140915E (pt)	2005-11-30
BR9916491A (pt)	2001-09-04
JP2002533337A (ja)	2002-10-08
US7205410B2 (en)	2007-04-17
HUP0104838A2 (hu)	2002-07-29
DE69925865D1 (de)	2005-07-21
EP1140915A1 (en)	2001-10-10
EE200100335A (et)	2002-08-15
EP1140915B1 (en)	2005-06-15
US20030181456A1 (en)	2003-09-25
WO2000037461A1 (en)	2000-06-29
US6544997B1 (en)	2003-04-08
CZ300851B6 (cs)	2009-08-26
ZA200105135B (en)	2002-06-21
CA2355857A1 (en)	2000-06-29
NO321324B1 (no)	2006-04-24
NZ512871A (en)	2002-11-26
HUP0104838A3 (en)	2003-05-28
BG105571A (en)	2002-01-31
AR024240A1 (es)	2002-09-25
DK1140915T3 (da)	2005-10-10
CN1150190C (zh)	2004-05-19
DE69925865T2 (de)	2006-05-11
HK1039114B (en)	2005-08-19
SI1140915T1 (sl)	2005-12-31
PL197409B1 (pl)	2008-03-31
CN1331690A (zh)	2002-01-16
IL143858A (en)	2005-03-20
NO20012858L (no)	2001-06-08
MY121852A (en)	2006-02-28
JP4615725B2 (ja)	2011-01-19
HRP20010445A2 (en)	2002-06-30
PL348417A1 (en)	2002-05-20
SK285829B6 (sk)	2007-09-06
TW570920B (en)	2004-01-11
ID28953A (id)	2001-07-19
KR100633680B1 (ko)	2006-10-11
EA200100710A1 (ru)	2001-12-24
AU770397B2 (en)	2004-02-19
EA003608B1 (ru)	2003-06-26
AU2432800A (en)	2000-07-12
NO20012858D0 (no)	2001-06-08
CZ20012117A3 (cs)	2001-10-17

Publication	Publication Date	Title
UA71591C2 (en)	2004-12-15	4-(aminomethyl)piperidine benzamide derivatives, pharmaceutical composition based thereon, a process for preparing thereof (variants), an intermediary compound and a method for preparing thereof
DE69820065T2 (de)	2004-08-26	Gastrokinetische monocyclische benzamide von 3- oder 4-substituierte 4-(aminomethyl)-piperidinderivative
CA2979504C (en)	2023-10-10	Benzimidazole derivatives as bromodomain inhibitors
AU2006332124B2 (en)	2011-03-03	3 , 5-substitgammaued piperidine compounds as renin inhibitors
NZ332777A (en)	2000-06-23	3,6-bi-phenyl substituted spiro-piperidine derivatives
NO339158B1 (no)	2016-11-14	Salt av arylamidin-derivat og anti-soppmiddel inneholdende dette
JP5805792B2 (ja)	2015-11-10	ヒスタミンｈ３レセプターリガンドとしての新規な化合物
US7091354B2 (en)	2006-08-15	Processes for the preparation of peripheral opioid antagonist compounds and intermediates thereto
JP2013224263A (ja)	2013-10-31	４−イソプロピルフェニルグルシトール化合物
DE69513846T2 (de)	2000-07-06	N-substituierte piperidinyl bicyclische benzoatderivate
EA009259B1 (ru)	2007-12-28	Аминосульфонилзамещенные 4-(аминометил)пиперидинбензамиды в качестве 5ht-антагонистов
EP0449195A2 (en)	1991-10-02	Aminobenzene compounds, their production and use
WO1996030372A1 (en)	1996-10-03	Diazabicyclo[3.3.1]nonane derivatives and intermediates thereof, medicinal use of the same, and processes for producing the same
DE69714413T2 (de)	2003-04-24	Ester von 3-hydroxy-piperidinmethanol-derivaten
CA2165947A1 (en)	1995-01-05	N-substituted azaheterocyclic carboxylic acids and esters thereof
JPS6360958A (ja)	1988-03-17	非イオン造影剤合成用中間体
EA009464B1 (ru)	2007-12-28	Бензамиды 4-(аминометил)пиперидина, замещённого гидроксикарбонилфенилом, в качестве антагонистов 5нт-рецепторов
MXPA00000418A (en)	2001-11-21	Gastrokinetic monocyclic benzamides of 3- or 4-substituted 4-(aminomethyl)-piperidine derivatives
NZ622539B2 (en)	2015-09-01	Diphenoxyphenyl derivative
NZ622539A (en)	2015-05-29	Diphenoxyphenyl derivative
MXPA01006409A (en)	2001-12-13	4-(aminomethyl)-piperidine benzamides for treating gastrointestinal disorders
HK1025093B (en)	2004-04-02	Gastrokinetic monocyclic benzamides of 3- or 4-substituted 4-(aminomethyl)-piperidine derivatives