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 PDFInfo
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- UA71591C2 UA71591C2 UA2001064399A UA2001064399A UA71591C2 UA 71591 C2 UA71591 C2 UA 71591C2 UA 2001064399 A UA2001064399 A UA 2001064399A UA 2001064399 A UA2001064399 A UA 2001064399A UA 71591 C2 UA71591 C2 UA 71591C2
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- Ukraine
- Prior art keywords
- formula
- alkyl
- compound
- group
- hydrogen
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- 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
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- 235000003599 food sweetener Nutrition 0.000 description 6
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- 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
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- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 5
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- 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
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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- 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
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- 206010020651 Hyperkinesia Diseases 0.000 description 3
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- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
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- 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
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- 210000001035 gastrointestinal tract Anatomy 0.000 description 3
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- 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
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Classifications
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (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)
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 (ja) |
| EP (1) | EP1140915B1 (ja) |
| JP (1) | JP4615725B2 (ja) |
| KR (1) | KR100633680B1 (ja) |
| CN (1) | CN1150190C (ja) |
| AR (1) | AR024240A1 (ja) |
| AT (1) | ATE297917T1 (ja) |
| AU (1) | AU770397B2 (ja) |
| BG (1) | BG64953B1 (ja) |
| BR (1) | BR9916491A (ja) |
| CA (1) | CA2355857C (ja) |
| CZ (1) | CZ300851B6 (ja) |
| DE (1) | DE69925865T2 (ja) |
| DK (1) | DK1140915T3 (ja) |
| EA (1) | EA003608B1 (ja) |
| EE (1) | EE200100335A (ja) |
| ES (1) | ES2245131T3 (ja) |
| HK (1) | HK1039114B (ja) |
| HR (1) | HRP20010445A2 (ja) |
| HU (1) | HUP0104838A3 (ja) |
| ID (1) | ID28953A (ja) |
| IL (1) | IL143858A (ja) |
| MY (1) | MY121852A (ja) |
| NO (1) | NO321324B1 (ja) |
| NZ (1) | NZ512871A (ja) |
| PL (1) | PL197409B1 (ja) |
| PT (1) | PT1140915E (ja) |
| SI (1) | SI1140915T1 (ja) |
| SK (1) | SK285829B6 (ja) |
| TR (1) | TR200101962T2 (ja) |
| TW (1) | TW570920B (ja) |
| UA (1) | UA71591C2 (ja) |
| WO (1) | WO2000037461A1 (ja) |
| ZA (1) | ZA200105135B (ja) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004024143A1 (ja) * | 2002-09-12 | 2004-03-25 | Nagase Chemtex Corporation | 医薬組成物 |
| JO2478B1 (en) | 2003-06-19 | 2009-01-20 | جانسين فارماسوتيكا ان. في. | (Aminomethyl) -biperidine benzamides as 5 HT4 antagonists |
| DE602004009069T2 (de) * | 2003-06-19 | 2008-06-19 | Janssen Pharmaceutica N.V. | 4-(aminomethyl)-piperidinbenzamide als 5ht4-antagonisten |
| ES2336448T3 (es) * | 2003-06-19 | 2010-04-13 | Janssen Pharmaceutica Nv | 4-(aminometil)-piperidina-benzamidas con sustituyentes heterociclicos como antagonistas de 5ht4. |
| EA009464B1 (ru) * | 2003-06-19 | 2007-12-28 | Янссен Фармацевтика Н.В. | Бензамиды 4-(аминометил)пиперидина, замещённого гидроксикарбонилфенилом, в качестве антагонистов 5нт-рецепторов |
| JP4916878B2 (ja) * | 2003-06-19 | 2012-04-18 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | ５ｈｔ４−拮抗薬としてのアミノスルホニル置換４−（アミノメチル）−ピペリジンベンズアミド |
| ES2377484T3 (es) * | 2003-09-03 | 2012-03-28 | Pfizer, Inc. | Compuestos de bencimidazolona que tiene actividad agonista del receptor 5-HT |
| US7964727B2 (en) * | 2003-11-24 | 2011-06-21 | Pfizer Inc. | Quinolonecarboxylic acid compounds having 5-HT4 receptor agonistic activity |
| TW200533348A (en) * | 2004-02-18 | 2005-10-16 | Theravance Inc | Indazole-carboxamide compounds as 5-ht4 receptor agonists |
| US8309575B2 (en) | 2004-04-07 | 2012-11-13 | Theravance, Inc. | Quinolinone-carboxamide compounds as 5-HT4 receptor agonists |
| US7728006B2 (en) * | 2004-04-07 | 2010-06-01 | Theravance, Inc. | Quinolinone-carboxamide compounds as 5-HT4 receptor agonists |
| TWI351282B (en) | 2004-04-07 | 2011-11-01 | Theravance Inc | Quinolinone-carboxamide compounds as 5-ht4 recepto |
| AU2005254800B2 (en) | 2004-06-15 | 2010-12-09 | Pfizer Inc. | Benzimidazolone carboxylic acid derivatives |
| US20060035890A1 (en) * | 2004-08-10 | 2006-02-16 | Amit Banerjee | Compounds and methods for the treatment of ubiquitin conjugating disorders |
| ES2332808T3 (es) * | 2004-11-05 | 2010-02-12 | Theravance, Inc. | Compuestos agonistas del receptor 5-ht4. |
| EP1807423B1 (en) * | 2004-11-05 | 2009-05-20 | Theravance, Inc. | Quinolinone-carboxamide compounds |
| RU2404179C2 (ru) * | 2004-12-22 | 2010-11-20 | Тереванс, Инк. | Индазол-карбоксамидные соединения |
| WO2006094063A1 (en) * | 2005-03-02 | 2006-09-08 | Theravance, Inc. | Quinolinone compounds as 5-ht4 receptor agonists |
| US9101160B2 (en) | 2005-11-23 | 2015-08-11 | The Coca-Cola Company | Condiments with high-potency sweetener |
| US8017168B2 (en) | 2006-11-02 | 2011-09-13 | The Coca-Cola Company | High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith |
| US8377968B2 (en) * | 2008-06-02 | 2013-02-19 | Zalicus Pharmaceuticals, Ltd. | N-piperidinyl acetamide derivatives as calcium channel blockers |
| US10208023B2 (en) | 2013-03-01 | 2019-02-19 | Mark G. DeGiacomo | Heterocyclic inhibitors of the sodium channel |
| CA3001857A1 (en) * | 2015-10-14 | 2017-04-20 | Aquinnah Pharmaceuticals, Inc. | Compounds, compositions and methods of use against stress granules |
| WO2021007487A1 (en) | 2019-07-11 | 2021-01-14 | Praxis Precision Medicines, Inc. | Formulations of t-type calcium channel modulators and methods of use thereof |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ225152A (en) * | 1987-07-17 | 1990-04-26 | Janssen Pharmaceutica Nv | Heterocyclically substituted piperidinyl benzamides as pharmaceuticals |
| CA1317940C (en) * | 1987-09-25 | 1993-05-18 | Georges H. P. Van Daele | Substituted n-(1-alkyl-3-hydroxy-4-piperidinyl)benzamides |
| US5374637A (en) * | 1989-03-22 | 1994-12-20 | Janssen Pharmaceutica N.V. | N-(3-hydroxy-4-piperidinyl)(dihydrobenzofuran, dihydro-2H-benzopyran or dihydrobenzodioxin)carboxamide derivatives |
| CA2116024A1 (en) | 1991-08-20 | 1993-03-04 | Francis David King | 5-ht4 receptor antagonists |
| JP3294611B2 (ja) * | 1991-09-12 | 2002-06-24 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | ５−ｈｔ４レセプター・アンタゴニスト |
| JP2525552B2 (ja) * | 1992-01-23 | 1996-08-21 | 東レ株式会社 | モルヒナン誘導体および医薬用途 |
| CA2129112A1 (en) * | 1992-02-06 | 1993-08-19 | Francis David King | Benzopyran, benzothiopyran and benzofuran derivatives as 5-ht4 antagonists |
| GB9219163D0 (en) | 1992-09-10 | 1992-10-28 | Smithkline Beecham Plc | Pharmaceuticals |
| MX9306311A (es) | 1992-10-13 | 1994-04-29 | Smithkline Beecham Plc | Compuestos antagonistas del receptor de 5-ht4, procedimiento para su preparacion y composiciones farmaceuticas que los contienen |
| JPH08502273A (ja) | 1992-10-13 | 1996-03-12 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | ５−ｈｔ▲下４▼レセプターアンタゴニスト用複素環式エステルまたはアミド |
| EP0667867A1 (en) * | 1992-11-05 | 1995-08-23 | Smithkline Beecham Plc | Piperidine derivatives as 5-ht4 receptor antagonists |
| GB9301660D0 (en) * | 1993-01-28 | 1993-03-17 | Smithkline Beecham Plc | Pharmaceuticals |
| GB9312348D0 (en) | 1993-06-16 | 1993-07-28 | Smithkline Beecham Plc | Pharmaceuticals |
| ES2103675B1 (es) * | 1995-01-10 | 1998-07-01 | Almirall Lab | Nuevas piperidinas sustituidas. |
| IT1275903B1 (it) | 1995-03-14 | 1997-10-24 | Boehringer Ingelheim Italia | Esteri e ammidi della 1,4-piperidina disostituita |
| GB9507882D0 (en) | 1995-04-18 | 1995-05-31 | Pharmacia Spa | Substituted dihydrobenzofuran derivatives as 5-ht4 agonists |
| ES2208870T3 (es) * | 1996-02-15 | 2004-06-16 | Janssen Pharmaceutica N.V. | Uso de antagonistas del receptor 5ht4 para resolver los efectos gastrointestinales de los inhibidores de la reabsorcion de serotonina. |
| TW445263B (en) * | 1996-02-29 | 2001-07-11 | Janssen Pharmaceutica Nv | Novel esters of 1,4-disubstituted piperidine derivatives |
| TW402591B (en) * | 1997-07-11 | 2000-08-21 | Janssen Pharmaceutica Nv | Monocyclic benzamides of 3- or 4-substituted 4-(aminomethyl)-piperidine derivatives |
| KR100413150B1 (ko) * | 1998-09-10 | 2003-12-31 | 에프. 호프만-라 로슈 아게 | 5-에이치티4 수용체 길항제로서의 디하이드로벤조디옥신 카복스아미드 및 케톤 유도체 |
| DE10217868A1 (de) * | 2002-04-22 | 2003-10-30 | Jomed N V | Ballon-Katheter |
-
1999
- 1999-12-03 TW TW088121125A patent/TW570920B/zh not_active IP Right Cessation
- 1999-12-14 DE DE69925865T patent/DE69925865T2/de not_active Expired - Lifetime
- 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 ID IDW00200101336A patent/ID28953A/id unknown
- 1999-12-14 US US09/857,905 patent/US6544997B1/en not_active Expired - Lifetime
- 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 CZ CZ20012117A patent/CZ300851B6/cs not_active IP Right Cessation
- 1999-12-14 PT PT99967956T patent/PT1140915E/pt unknown
- 1999-12-14 DK DK99967956T patent/DK1140915T3/da active
- 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 CN CNB998147699A patent/CN1150190C/zh not_active Expired - Fee Related
- 1999-12-14 HU HU0104838A patent/HUP0104838A3/hu unknown
- 1999-12-14 PL PL348417A patent/PL197409B1/pl unknown
- 1999-12-14 AU AU24328/00A patent/AU770397B2/en not_active Ceased
- 1999-12-14 CA CA002355857A patent/CA2355857C/en not_active Expired - Fee Related
- 1999-12-14 KR KR1020017005055A patent/KR100633680B1/ko not_active IP Right Cessation
- 1999-12-14 NZ NZ512871A patent/NZ512871A/xx unknown
- 1999-12-14 WO PCT/EP1999/010064 patent/WO2000037461A1/en active IP Right Grant
- 1999-12-14 EP EP99967956A patent/EP1140915B1/en not_active Expired - Lifetime
- 1999-12-14 SI SI9930822T patent/SI1140915T1/sl unknown
- 1999-12-14 UA UA2001064399A patent/UA71591C2/uk unknown
- 1999-12-14 SK SK859-2001A patent/SK285829B6/sk not_active IP Right Cessation
- 1999-12-14 JP JP2000589532A patent/JP4615725B2/ja not_active Expired - Fee Related
- 1999-12-14 ES ES99967956T patent/ES2245131T3/es not_active Expired - Lifetime
- 1999-12-17 MY MYPI99005534A patent/MY121852A/en unknown
- 1999-12-21 AR ARP990106644A patent/AR024240A1/es active IP Right Grant
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2001
- 2001-06-07 BG BG105571A patent/BG64953B1/bg unknown
- 2001-06-08 NO NO20012858A patent/NO321324B1/no not_active IP Right Cessation
- 2001-06-14 HR HR20010445A patent/HRP20010445A2/hr not_active Application Discontinuation
- 2001-06-21 ZA ZA200105135A patent/ZA200105135B/en unknown
-
2002
- 2002-01-29 HK HK02100161.1A patent/HK1039114B/zh not_active IP Right Cessation
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2003
- 2003-01-29 US US10/353,307 patent/US7205410B2/en not_active Expired - Fee Related
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