ES2336952T3 - Compuesto de carbamato como agonistas del recepttor 5-ht4. - Google Patents
Compuesto de carbamato como agonistas del recepttor 5-ht4. Download PDFInfo
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- ES2336952T3 ES2336952T3 ES06838207T ES06838207T ES2336952T3 ES 2336952 T3 ES2336952 T3 ES 2336952T3 ES 06838207 T ES06838207 T ES 06838207T ES 06838207 T ES06838207 T ES 06838207T ES 2336952 T3 ES2336952 T3 ES 2336952T3
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- alkyl
- isopropyl
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- -1 CARBAMATE COMPOUND Chemical class 0.000 title claims description 59
- 239000000556 agonist Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 195
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 34
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 239000001257 hydrogen Substances 0.000 claims abstract description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000012453 solvate Substances 0.000 claims abstract description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 10
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 6
- 238000000034 method Methods 0.000 claims description 63
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 36
- 108091005482 5-HT4 receptors Proteins 0.000 claims description 33
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 31
- 239000008194 pharmaceutical composition Substances 0.000 claims description 26
- 230000000694 effects Effects 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 16
- 230000002829 reductive effect Effects 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 14
- 206010010774 Constipation Diseases 0.000 claims description 13
- 241000124008 Mammalia Species 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 10
- 230000004899 motility Effects 0.000 claims description 10
- 206010021518 Impaired gastric emptying Diseases 0.000 claims description 9
- 201000006549 dyspepsia Diseases 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- 230000001684 chronic effect Effects 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 238000000338 in vitro Methods 0.000 claims description 8
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- 230000003111 delayed effect Effects 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 5
- 208000001288 gastroparesis Diseases 0.000 claims description 5
- 206010052105 Gastrointestinal hypomotility Diseases 0.000 claims description 4
- 201000005081 Intestinal Pseudo-Obstruction Diseases 0.000 claims description 4
- 206010054048 Postoperative ileus Diseases 0.000 claims description 4
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- 101710133393 POU domain, class 3, transcription factor 3 Proteins 0.000 claims description 3
- HZWNCWJPJSKCTL-SCSAIBSYSA-N (2r)-2-carbamoylpyrrolidine-1-carboxylic acid Chemical compound NC(=O)[C@H]1CCCN1C(O)=O HZWNCWJPJSKCTL-SCSAIBSYSA-N 0.000 claims description 2
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims description 2
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 11
- 229910003827 NRaRb Inorganic materials 0.000 abstract 2
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- 239000000203 mixture Substances 0.000 description 71
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 61
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- 238000012360 testing method Methods 0.000 description 49
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- 239000002904 solvent Substances 0.000 description 26
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 23
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
- 239000013543 active substance Substances 0.000 description 17
- 238000009472 formulation Methods 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
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- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 13
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 13
- 239000000872 buffer Substances 0.000 description 13
- 239000000018 receptor agonist Substances 0.000 description 13
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- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
- 235000019439 ethyl acetate Nutrition 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
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- 239000012188 paraffin wax Substances 0.000 description 1
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- 230000002093 peripheral effect Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- GGGMTJQCYUFHPX-UHFFFAOYSA-N piperidin-4-yl n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC1CCNCC1 GGGMTJQCYUFHPX-UHFFFAOYSA-N 0.000 description 1
- CXWQAPHDSYDHBR-UHFFFAOYSA-N piperidine-4-carboxamide Chemical compound NC(=O)C1CCNCC1.NC(=O)C1CCNCC1 CXWQAPHDSYDHBR-UHFFFAOYSA-N 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920002744 polyvinyl acetate phthalate Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- ZUFQODAHGAHPFQ-UHFFFAOYSA-N pyridoxine hydrochloride Chemical compound Cl.CC1=NC=C(CO)C(CO)=C1O ZUFQODAHGAHPFQ-UHFFFAOYSA-N 0.000 description 1
- 229960004172 pyridoxine hydrochloride Drugs 0.000 description 1
- 235000019171 pyridoxine hydrochloride Nutrition 0.000 description 1
- 239000011764 pyridoxine hydrochloride Substances 0.000 description 1
- 239000002510 pyrogen Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000003127 radioimmunoassay Methods 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 230000001373 regressive effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 229940100996 sodium bisulfate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- CSMWJXBSXGUPGY-UHFFFAOYSA-L sodium dithionate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)S([O-])(=O)=O CSMWJXBSXGUPGY-UHFFFAOYSA-L 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- MBDNRNMVTZADMQ-UHFFFAOYSA-N sulfolene Chemical compound O=S1(=O)CC=CC1 MBDNRNMVTZADMQ-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- NZJKEPNCNBWESN-PBINXNQUSA-N tert-butyl (1s,5r)-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate Chemical compound C1C(N)C[C@H]2CC[C@@H]1N2C(=O)OC(C)(C)C NZJKEPNCNBWESN-PBINXNQUSA-N 0.000 description 1
- CMIBWIAICVBURI-UHFFFAOYSA-N tert-butyl 3-aminopyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(N)C1 CMIBWIAICVBURI-UHFFFAOYSA-N 0.000 description 1
- MENILFUADYEXNU-UHFFFAOYSA-N tert-butyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate Chemical compound C1C(=O)CC2CCC1N2C(=O)OC(C)(C)C MENILFUADYEXNU-UHFFFAOYSA-N 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229950000339 xinafoate Drugs 0.000 description 1
- XOFLBQFBSOEHOG-UUOKFMHZSA-N γS-GTP Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=S)[C@@H](O)[C@H]1O XOFLBQFBSOEHOG-UUOKFMHZSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/46—8-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
-
- 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
- A61P1/10—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nutrition Science (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73870205P | 2005-11-22 | 2005-11-22 | |
| US738702P | 2005-11-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2336952T3 true ES2336952T3 (es) | 2010-04-19 |
Family
ID=38067868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES06838207T Active ES2336952T3 (es) | 2005-11-22 | 2006-11-21 | Compuesto de carbamato como agonistas del recepttor 5-ht4. |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US7329752B2 (https=) |
| EP (1) | EP1960396B1 (https=) |
| JP (1) | JP2009516745A (https=) |
| KR (1) | KR20080072727A (https=) |
| CN (1) | CN101312967B (https=) |
| AR (1) | AR057627A1 (https=) |
| AT (1) | ATE448224T1 (https=) |
| AU (1) | AU2006318507A1 (https=) |
| BR (1) | BRPI0618835A2 (https=) |
| CA (1) | CA2630222A1 (https=) |
| DE (1) | DE602006010432D1 (https=) |
| EA (1) | EA014819B1 (https=) |
| ES (1) | ES2336952T3 (https=) |
| MY (1) | MY143574A (https=) |
| NO (1) | NO20082597L (https=) |
| NZ (1) | NZ567653A (https=) |
| PE (1) | PE20070954A1 (https=) |
| TW (1) | TW200804366A (https=) |
| WO (1) | WO2007062058A2 (https=) |
| ZA (1) | ZA200804010B (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101163701A (zh) * | 2005-03-02 | 2008-04-16 | 施万制药 | 作为5-ht4受体激动剂的喹啉酮化合物 |
| CN101384588B (zh) * | 2006-02-16 | 2011-08-31 | 施万制药 | 制备5-ht4受体激动剂化合物的中间体的方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5223511A (en) | 1987-09-23 | 1993-06-29 | Boehringer Ingelheim Italia S.P.A. | Benzimidazoline-2-oxo-1-carboxylic acid compounds useful as 5-HT receptor antagonists |
| IT1231413B (it) | 1987-09-23 | 1991-12-04 | Angeli Inst Spa | Derivati dell'acido benzimidazolin-2-osso-1-carbossilico utili come antagonisti dei recettori 5-ht |
| JP3829879B2 (ja) | 1994-05-18 | 2006-10-04 | 大正製薬株式会社 | キノリンカルボン酸誘導体 |
| IT1275903B1 (it) | 1995-03-14 | 1997-10-24 | Boehringer Ingelheim Italia | Esteri e ammidi della 1,4-piperidina disostituita |
| US6069152A (en) * | 1997-10-07 | 2000-05-30 | Eli Lilly And Company | 5-HT4 agonists and antagonists |
| IT1298271B1 (it) | 1998-02-18 | 1999-12-20 | Boehringer Ingelheim Italia | Esteri ed ammidi dell'acido 2-oxo-2,3-diidro-benzimidazol-1- carbossilico |
| EP1173168A2 (en) | 1999-04-28 | 2002-01-23 | Respiratorius AB | Compound for use as a medicament for treatment of disorders involving bronchocontraction |
| IT1313625B1 (it) | 1999-09-22 | 2002-09-09 | Boehringer Ingelheim Italia | Derivati benzimidazolonici aventi affinita' mista per i recettori diserotonina e dopamina. |
| JP4181847B2 (ja) * | 2002-10-25 | 2008-11-19 | エルピーダメモリ株式会社 | タイミング調整回路、半導体装置及びタイミング調整方法 |
| KR100738784B1 (ko) | 2003-09-03 | 2007-07-12 | 화이자 인코포레이티드 | 5-ｈｔ4 수용체 효능 활성을 갖는 벤즈이미다졸론 |
| TW200533348A (en) | 2004-02-18 | 2005-10-16 | Theravance Inc | Indazole-carboxamide compounds as 5-ht4 receptor agonists |
| TWI351282B (en) | 2004-04-07 | 2011-11-01 | Theravance Inc | Quinolinone-carboxamide compounds as 5-ht4 recepto |
| WO2006052889A2 (en) * | 2004-11-05 | 2006-05-18 | Theravance, Inc. | Quinolinone-carboxamide compounds |
| US7399862B2 (en) | 2004-11-05 | 2008-07-15 | Theravance, Inc. | 5-HT4 receptor agonist compounds |
| CA2588037A1 (en) | 2004-12-22 | 2006-06-29 | Theravance, Inc. | Indazole-carboxamide compounds |
| CN101163701A (zh) * | 2005-03-02 | 2008-04-16 | 施万制药 | 作为5-ht4受体激动剂的喹啉酮化合物 |
| US7351304B2 (en) * | 2005-05-24 | 2008-04-01 | General Electric Company | Method and apparatus for reducing surface defects |
| EP1902053B1 (en) | 2005-06-07 | 2011-01-12 | Theravance, Inc. | Benzoimidazolone-carboxamide compounds as 5-ht4 receptor agonists |
-
2006
- 2006-11-09 MY MYPI20064472A patent/MY143574A/en unknown
- 2006-11-15 TW TW095142293A patent/TW200804366A/zh unknown
- 2006-11-21 AT AT06838207T patent/ATE448224T1/de not_active IP Right Cessation
- 2006-11-21 DE DE602006010432T patent/DE602006010432D1/de active Active
- 2006-11-21 JP JP2008542415A patent/JP2009516745A/ja active Pending
- 2006-11-21 EP EP06838207A patent/EP1960396B1/en active Active
- 2006-11-21 NZ NZ567653A patent/NZ567653A/en unknown
- 2006-11-21 EA EA200801402A patent/EA014819B1/ru not_active IP Right Cessation
- 2006-11-21 US US11/602,888 patent/US7329752B2/en active Active
- 2006-11-21 WO PCT/US2006/045099 patent/WO2007062058A2/en not_active Ceased
- 2006-11-21 BR BRPI0618835-4A patent/BRPI0618835A2/pt not_active IP Right Cessation
- 2006-11-21 ES ES06838207T patent/ES2336952T3/es active Active
- 2006-11-21 PE PE2006001486A patent/PE20070954A1/es not_active Application Discontinuation
- 2006-11-21 KR KR1020087014898A patent/KR20080072727A/ko not_active Ceased
- 2006-11-21 CN CN2006800433139A patent/CN101312967B/zh not_active Expired - Fee Related
- 2006-11-21 AU AU2006318507A patent/AU2006318507A1/en not_active Abandoned
- 2006-11-21 CA CA002630222A patent/CA2630222A1/en not_active Abandoned
- 2006-11-22 AR ARP060105125A patent/AR057627A1/es not_active Application Discontinuation
-
2007
- 2007-12-06 US US11/999,609 patent/US7851467B2/en not_active Expired - Fee Related
-
2008
- 2008-05-09 ZA ZA200804010A patent/ZA200804010B/xx unknown
- 2008-06-10 NO NO20082597A patent/NO20082597L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2630222A1 (en) | 2007-05-31 |
| US7851467B2 (en) | 2010-12-14 |
| EP1960396B1 (en) | 2009-11-11 |
| US20080090811A1 (en) | 2008-04-17 |
| ZA200804010B (en) | 2009-02-25 |
| EA014819B1 (ru) | 2011-02-28 |
| EA200801402A1 (ru) | 2008-10-30 |
| NZ567653A (en) | 2011-06-30 |
| CN101312967A (zh) | 2008-11-26 |
| MY143574A (en) | 2011-05-31 |
| DE602006010432D1 (de) | 2009-12-24 |
| WO2007062058A3 (en) | 2007-09-07 |
| PE20070954A1 (es) | 2007-09-10 |
| AU2006318507A1 (en) | 2007-05-31 |
| US20070117796A1 (en) | 2007-05-24 |
| EP1960396A2 (en) | 2008-08-27 |
| ATE448224T1 (de) | 2009-11-15 |
| NO20082597L (no) | 2008-06-10 |
| JP2009516745A (ja) | 2009-04-23 |
| AR057627A1 (es) | 2007-12-05 |
| US7329752B2 (en) | 2008-02-12 |
| CN101312967B (zh) | 2011-08-24 |
| BRPI0618835A2 (pt) | 2011-09-13 |
| WO2007062058A2 (en) | 2007-05-31 |
| TW200804366A (en) | 2008-01-16 |
| KR20080072727A (ko) | 2008-08-06 |
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