JP5232143B2 - モチリン受容体アンタゴニストとしてのベンジルピペラジン誘導体 - Google Patents
モチリン受容体アンタゴニストとしてのベンジルピペラジン誘導体 Download PDFInfo
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- JP5232143B2 JP5232143B2 JP2009514801A JP2009514801A JP5232143B2 JP 5232143 B2 JP5232143 B2 JP 5232143B2 JP 2009514801 A JP2009514801 A JP 2009514801A JP 2009514801 A JP2009514801 A JP 2009514801A JP 5232143 B2 JP5232143 B2 JP 5232143B2
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- Prior art keywords
- methyl
- phenyl
- amino
- formula
- piperidinecarboxamide
- Prior art date
- Legal status (The legal status 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 status listed.)
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- 102000057413 Motilin receptors Human genes 0.000 title description 7
- 108700040483 Motilin receptors Proteins 0.000 title description 7
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical class C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 title description 2
- 239000002464 receptor antagonist Substances 0.000 title 1
- 229940044551 receptor antagonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 191
- 238000000034 method Methods 0.000 claims abstract description 60
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- 230000008569 process Effects 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims description 40
- -1 (piperazinyl) methylene substituent Chemical group 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 16
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- VAHGCBIEHWKWMD-IBGZPJMESA-N 4-(3-fluoroanilino)-n-methyl-n-[4-[[(3s)-3-methylpiperazin-1-yl]methyl]phenyl]piperidine-1-carboxamide Chemical compound C1CN[C@@H](C)CN1CC1=CC=C(N(C)C(=O)N2CCC(CC2)NC=2C=C(F)C=CC=2)C=C1 VAHGCBIEHWKWMD-IBGZPJMESA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 238000006268 reductive amination reaction Methods 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- 230000009467 reduction Effects 0.000 claims description 5
- 238000006722 reduction reaction Methods 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- CBGQNRZLQSNQNS-FQEVSTJZSA-N 4-(3-cyanophenyl)-n-methyl-n-[4-[[(3s)-3-methylpiperazin-1-yl]methyl]phenyl]piperidine-1-carboxamide Chemical compound C1CN[C@@H](C)CN1CC1=CC=C(N(C)C(=O)N2CCC(CC2)C=2C=C(C=CC=2)C#N)C=C1 CBGQNRZLQSNQNS-FQEVSTJZSA-N 0.000 claims description 4
- QEJHPRPCSRIROF-SFHVURJKSA-N 4-(3-fluoroanilino)-n-methyl-n-[6-[[(3s)-3-methylpiperazin-1-yl]methyl]pyridin-3-yl]piperidine-1-carboxamide Chemical compound C1CN[C@@H](C)CN1CC1=CC=C(N(C)C(=O)N2CCC(CC2)NC=2C=C(F)C=CC=2)C=N1 QEJHPRPCSRIROF-SFHVURJKSA-N 0.000 claims description 4
- ZMIHIMYJXRASEQ-IBGZPJMESA-N 4-(3-fluorophenyl)-n-methyl-n-[4-[[(3s)-3-methylpiperazin-1-yl]methyl]phenyl]piperidine-1-carboxamide Chemical compound C1CN[C@@H](C)CN1CC1=CC=C(N(C)C(=O)N2CCC(CC2)C=2C=C(F)C=CC=2)C=C1 ZMIHIMYJXRASEQ-IBGZPJMESA-N 0.000 claims description 4
- OJJXMMVVELBULF-IBGZPJMESA-N 4-(4-fluorophenyl)-n-methyl-n-[4-[[(3s)-3-methylpiperazin-1-yl]methyl]phenyl]piperidine-1-carboxamide Chemical compound C1CN[C@@H](C)CN1CC1=CC=C(N(C)C(=O)N2CCC(CC2)C=2C=CC(F)=CC=2)C=C1 OJJXMMVVELBULF-IBGZPJMESA-N 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- UGSIGXWFIZZAAR-FQEVSTJZSA-N 4-(3-fluoroanilino)-n-methyl-n-[3-methyl-4-[[(3s)-3-methylpiperazin-1-yl]methyl]phenyl]piperidine-1-carboxamide Chemical compound C1CN[C@@H](C)CN1CC1=CC=C(N(C)C(=O)N2CCC(CC2)NC=2C=C(F)C=CC=2)C=C1C UGSIGXWFIZZAAR-FQEVSTJZSA-N 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- AEMCAHYRZPQHGI-IBGZPJMESA-N 4-(2-carbamoylanilino)-n-methyl-n-[4-[[(3s)-3-methylpiperazin-1-yl]methyl]phenyl]piperidine-1-carboxamide Chemical compound C1CN[C@@H](C)CN1CC1=CC=C(N(C)C(=O)N2CCC(CC2)NC=2C(=CC=CC=2)C(N)=O)C=C1 AEMCAHYRZPQHGI-IBGZPJMESA-N 0.000 claims description 2
- NOOCUGDSASZTIW-FQEVSTJZSA-N 4-(2-cyanoanilino)-n-methyl-n-[4-[[(3s)-3-methylpiperazin-1-yl]methyl]phenyl]piperidine-1-carboxamide Chemical compound C1CN[C@@H](C)CN1CC1=CC=C(N(C)C(=O)N2CCC(CC2)NC=2C(=CC=CC=2)C#N)C=C1 NOOCUGDSASZTIW-FQEVSTJZSA-N 0.000 claims description 2
- RVEDDKMAENNWSJ-IBGZPJMESA-N 4-(2-fluoroanilino)-n-methyl-n-[4-[[(3s)-3-methylpiperazin-1-yl]methyl]phenyl]piperidine-1-carboxamide Chemical compound C1CN[C@@H](C)CN1CC1=CC=C(N(C)C(=O)N2CCC(CC2)NC=2C(=CC=CC=2)F)C=C1 RVEDDKMAENNWSJ-IBGZPJMESA-N 0.000 claims description 2
- POTIXHFLOMRIPL-UHFFFAOYSA-N 4-(3-cyanoanilino)-n-methyl-n-[4-(piperazin-1-ylmethyl)phenyl]piperidine-1-carboxamide Chemical compound C=1C=C(CN2CCNCC2)C=CC=1N(C)C(=O)N(CC1)CCC1NC1=CC=CC(C#N)=C1 POTIXHFLOMRIPL-UHFFFAOYSA-N 0.000 claims description 2
- YTEWUWUUWKZUEH-FQEVSTJZSA-N 4-(3-cyanoanilino)-n-methyl-n-[4-[[(3s)-3-methylpiperazin-1-yl]methyl]phenyl]piperidine-1-carboxamide Chemical compound C1CN[C@@H](C)CN1CC1=CC=C(N(C)C(=O)N2CCC(CC2)NC=2C=C(C=CC=2)C#N)C=C1 YTEWUWUUWKZUEH-FQEVSTJZSA-N 0.000 claims description 2
- WMSXCTMDOXKYEK-IBGZPJMESA-N 4-(3-fluoro-4-methoxyanilino)-n-methyl-n-[4-[[(3s)-3-methylpiperazin-1-yl]methyl]phenyl]piperidine-1-carboxamide Chemical compound C1=C(F)C(OC)=CC=C1NC1CCN(C(=O)N(C)C=2C=CC(CN3C[C@H](C)NCC3)=CC=2)CC1 WMSXCTMDOXKYEK-IBGZPJMESA-N 0.000 claims description 2
- GBDNMGFJZHEWJK-UHFFFAOYSA-N 4-(3-fluoroanilino)-n-methyl-n-[4-(piperazin-1-ylmethyl)phenyl]piperidine-1-carboxamide Chemical compound C=1C=C(CN2CCNCC2)C=CC=1N(C)C(=O)N(CC1)CCC1NC1=CC=CC(F)=C1 GBDNMGFJZHEWJK-UHFFFAOYSA-N 0.000 claims description 2
- VAHGCBIEHWKWMD-LJQANCHMSA-N 4-(3-fluoroanilino)-n-methyl-n-[4-[[(3r)-3-methylpiperazin-1-yl]methyl]phenyl]piperidine-1-carboxamide Chemical compound C1CN[C@H](C)CN1CC1=CC=C(N(C)C(=O)N2CCC(CC2)NC=2C=C(F)C=CC=2)C=C1 VAHGCBIEHWKWMD-LJQANCHMSA-N 0.000 claims description 2
- MHWVNOWZAYMLBI-IBGZPJMESA-N 4-(3-fluorophenoxy)-n-methyl-n-[4-[[(3s)-3-methylpiperazin-1-yl]methyl]phenyl]piperidine-1-carboxamide Chemical compound C1CN[C@@H](C)CN1CC1=CC=C(N(C)C(=O)N2CCC(CC2)OC=2C=C(F)C=CC=2)C=C1 MHWVNOWZAYMLBI-IBGZPJMESA-N 0.000 claims description 2
- VBSRCXCGKMBKIV-FQEVSTJZSA-N 4-(4-cyanoanilino)-n-methyl-n-[4-[[(3s)-3-methylpiperazin-1-yl]methyl]phenyl]piperidine-1-carboxamide Chemical compound C1CN[C@@H](C)CN1CC1=CC=C(N(C)C(=O)N2CCC(CC2)NC=2C=CC(=CC=2)C#N)C=C1 VBSRCXCGKMBKIV-FQEVSTJZSA-N 0.000 claims description 2
- FQQOBLHOKLMWSN-IBGZPJMESA-N 4-(4-fluoro-3-methoxyanilino)-n-methyl-n-[4-[[(3s)-3-methylpiperazin-1-yl]methyl]phenyl]piperidine-1-carboxamide Chemical compound C1=C(F)C(OC)=CC(NC2CCN(CC2)C(=O)N(C)C=2C=CC(CN3C[C@H](C)NCC3)=CC=2)=C1 FQQOBLHOKLMWSN-IBGZPJMESA-N 0.000 claims description 2
- PDPFEGLNWDJQTL-UHFFFAOYSA-N 4-(4-fluoroanilino)-n-methyl-n-[4-(piperazin-1-ylmethyl)phenyl]piperidine-1-carboxamide Chemical compound C=1C=C(CN2CCNCC2)C=CC=1N(C)C(=O)N(CC1)CCC1NC1=CC=C(F)C=C1 PDPFEGLNWDJQTL-UHFFFAOYSA-N 0.000 claims description 2
- OKKIPMUUMQAQDL-IBGZPJMESA-N 4-(4-fluoroanilino)-n-methyl-n-[4-[[(3s)-3-methylpiperazin-1-yl]methyl]phenyl]piperidine-1-carboxamide Chemical compound C1CN[C@@H](C)CN1CC1=CC=C(N(C)C(=O)N2CCC(CC2)NC=2C=CC(F)=CC=2)C=C1 OKKIPMUUMQAQDL-IBGZPJMESA-N 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- LOZWNVRRUMVRHD-BGYRXZFFSA-N n-[4-[[(3s,5r)-3,5-dimethylpiperazin-1-yl]methyl]phenyl]-4-(3-fluoroanilino)-n-methylpiperidine-1-carboxamide Chemical compound C1[C@@H](C)N[C@@H](C)CN1CC1=CC=C(N(C)C(=O)N2CCC(CC2)NC=2C=C(F)C=CC=2)C=C1 LOZWNVRRUMVRHD-BGYRXZFFSA-N 0.000 claims description 2
- 101001132878 Homo sapiens Motilin receptor Proteins 0.000 abstract description 21
- 102100033818 Motilin receptor Human genes 0.000 abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 6
- 230000001404 mediated effect Effects 0.000 abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 139
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 129
- 239000000243 solution Substances 0.000 description 53
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 52
- 239000000203 mixture Substances 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- 239000002904 solvent Substances 0.000 description 41
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 32
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 238000004440 column chromatography Methods 0.000 description 28
- 235000019439 ethyl acetate Nutrition 0.000 description 26
- 239000010410 layer Substances 0.000 description 23
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- 239000007787 solid Substances 0.000 description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 20
- 239000012044 organic layer Substances 0.000 description 20
- 239000003921 oil Substances 0.000 description 19
- 235000019198 oils Nutrition 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 239000003643 water by type Substances 0.000 description 18
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
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- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 14
- 239000000556 agonist Substances 0.000 description 14
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 13
- 229920006395 saturated elastomer Polymers 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
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- 101800002372 Motilin Proteins 0.000 description 11
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- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
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- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
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- OLIDKJBMRLAXQA-UHFFFAOYSA-N n-(3-fluorophenyl)piperidin-4-amine Chemical compound FC1=CC=CC(NC2CCNCC2)=C1 OLIDKJBMRLAXQA-UHFFFAOYSA-N 0.000 description 6
- 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 6
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- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 5
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
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- 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
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- 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
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- 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
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Nutrition Science (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0611907.7A GB0611907D0 (en) | 2006-06-15 | 2006-06-15 | Compounds |
| GB0611907.7 | 2006-06-15 | ||
| PCT/EP2007/055890 WO2007144400A1 (en) | 2006-06-15 | 2007-06-14 | Benzylpiperazine derivatives as motilin receptor antagonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009539938A JP2009539938A (ja) | 2009-11-19 |
| JP2009539938A5 JP2009539938A5 (https=) | 2013-03-21 |
| JP5232143B2 true JP5232143B2 (ja) | 2013-07-10 |
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| EP (1) | EP2029538B1 (https=) |
| JP (1) | JP5232143B2 (https=) |
| AT (1) | ATE542795T1 (https=) |
| ES (1) | ES2379658T3 (https=) |
| GB (1) | GB0611907D0 (https=) |
| WO (1) | WO2007144400A1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9142971B2 (en) | 2006-03-07 | 2015-09-22 | Server Technology, Inc. | Power distribution, management, and monitoring systems and methods |
| US9952261B2 (en) | 2009-03-04 | 2018-04-24 | Server Technology, Inc. | Monitoring power-related parameters in a power distribution unit |
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| GB0611907D0 (en) * | 2006-06-15 | 2006-07-26 | Glaxo Group Ltd | Compounds |
| AU2006274212B2 (en) | 2005-07-26 | 2011-06-09 | Glaxo Group Limited | Benzylpiperazine derivates and their medical use |
| GB0524814D0 (en) * | 2005-12-05 | 2006-01-11 | Glaxo Group Ltd | Compounds |
| DE602007006019D1 (de) | 2006-06-28 | 2010-06-02 | Glaxo Group Ltd | Für die behandlung von durch den gpr38-rezeptor vermittelten krankheiten geeignete piperazinylderivate |
| US9452980B2 (en) * | 2009-12-22 | 2016-09-27 | Hoffmann-La Roche Inc. | Substituted benzamides |
| PL2560658T3 (pl) | 2010-04-21 | 2017-08-31 | Ventirx Pharmaceuticals, Inc. | Wzmacnianie cytotoksyczności komórkowej zależnej od przeciwciał |
| MY157542A (en) | 2010-09-27 | 2016-06-15 | Daiichi Sankyo Co Ltd | Cyclohexane derivative compound |
| WO2012109267A2 (en) | 2011-02-07 | 2012-08-16 | The Trustees Of The University Of Pennsylvania | Novel peptides and methods using same |
| WO2017157873A1 (en) | 2016-03-17 | 2017-09-21 | F. Hoffmann-La Roche Ag | 5-ethyl-4-methyl-pyrazole-3-carboxamide derivative having activity as agonist of taar |
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| AU2006274212B2 (en) | 2005-07-26 | 2011-06-09 | Glaxo Group Limited | Benzylpiperazine derivates and their medical use |
| GB0524814D0 (en) * | 2005-12-05 | 2006-01-11 | Glaxo Group Ltd | Compounds |
| DE602007006019D1 (de) * | 2006-06-28 | 2010-06-02 | Glaxo Group Ltd | Für die behandlung von durch den gpr38-rezeptor vermittelten krankheiten geeignete piperazinylderivate |
| GB0723317D0 (en) * | 2007-11-28 | 2008-01-09 | Glaxo Group Ltd | Compounds |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9142971B2 (en) | 2006-03-07 | 2015-09-22 | Server Technology, Inc. | Power distribution, management, and monitoring systems and methods |
| US9952261B2 (en) | 2009-03-04 | 2018-04-24 | Server Technology, Inc. | Monitoring power-related parameters in a power distribution unit |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007144400A1 (en) | 2007-12-21 |
| EP2029538B1 (en) | 2012-01-25 |
| GB0611907D0 (en) | 2006-07-26 |
| US8236953B2 (en) | 2012-08-07 |
| US20110275815A1 (en) | 2011-11-10 |
| US8012981B2 (en) | 2011-09-06 |
| ES2379658T3 (es) | 2012-04-30 |
| ATE542795T1 (de) | 2012-02-15 |
| US20090131453A1 (en) | 2009-05-21 |
| EP2029538A1 (en) | 2009-03-04 |
| JP2009539938A (ja) | 2009-11-19 |
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