KR20070086294A - 산 펌프 길항물질로 유용한 크로만 유도체 - Google Patents
산 펌프 길항물질로 유용한 크로만 유도체 Download PDFInfo
- Publication number
- KR20070086294A KR20070086294A KR1020077013608A KR20077013608A KR20070086294A KR 20070086294 A KR20070086294 A KR 20070086294A KR 1020077013608 A KR1020077013608 A KR 1020077013608A KR 20077013608 A KR20077013608 A KR 20077013608A KR 20070086294 A KR20070086294 A KR 20070086294A
- Authority
- KR
- South Korea
- Prior art keywords
- pyridine
- dihydro
- chromen
- carboxamide
- group
- 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.)
- Abandoned
Links
- 239000002253 acid Substances 0.000 title claims abstract description 35
- 239000005557 antagonist Substances 0.000 title abstract description 17
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical class C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 148
- 238000000034 method Methods 0.000 claims abstract description 50
- 150000003839 salts Chemical class 0.000 claims abstract description 33
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 30
- 201000010099 disease Diseases 0.000 claims abstract description 23
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims abstract description 17
- 201000006549 dyspepsia Diseases 0.000 claims abstract description 12
- 238000011282 treatment Methods 0.000 claims abstract description 11
- 230000001404 mediated effect Effects 0.000 claims abstract description 9
- 208000035475 disorder Diseases 0.000 claims abstract description 7
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims abstract description 6
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims abstract description 6
- 206010019375 Helicobacter infections Diseases 0.000 claims abstract description 5
- 208000010643 digestive system disease Diseases 0.000 claims abstract description 5
- 208000019505 Deglutition disease Diseases 0.000 claims abstract description 4
- 206010013642 Drooling Diseases 0.000 claims abstract description 4
- 208000007882 Gastritis Diseases 0.000 claims abstract description 4
- 208000018522 Gastrointestinal disease Diseases 0.000 claims abstract description 4
- 206010028813 Nausea Diseases 0.000 claims abstract description 4
- 206010030216 Oesophagitis Diseases 0.000 claims abstract description 4
- 208000002193 Pain Diseases 0.000 claims abstract description 4
- 208000008469 Peptic Ulcer Diseases 0.000 claims abstract description 4
- 208000008630 Sialorrhea Diseases 0.000 claims abstract description 4
- 208000007107 Stomach Ulcer Diseases 0.000 claims abstract description 4
- 208000025865 Ulcer Diseases 0.000 claims abstract description 4
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- 208000011580 syndromic disease Diseases 0.000 claims abstract 2
- -1 3,4-dihydro-2H-chromen-4-ylamino Chemical group 0.000 claims description 70
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 32
- 125000005843 halogen group Chemical group 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 230000002401 inhibitory effect Effects 0.000 claims description 14
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 14
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 238000001727 in vivo Methods 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- DDRHDBWMMVYRSJ-UHFFFAOYSA-N 8-(3,4-dihydro-2h-chromen-4-ylamino)-n-(2-hydroxyethyl)-n,2,3-trimethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C1COC2=CC=CC=C2C1NC1=CC(C(=O)N(CCO)C)=CN2C(C)=C(C)N=C21 DDRHDBWMMVYRSJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- KABGBOMCMMYGCG-UHFFFAOYSA-N 8-[(5,7-difluoro-3,4-dihydro-2h-chromen-4-yl)amino]-n,n,2,3-tetramethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C1COC2=CC(F)=CC(F)=C2C1NC1=CC(C(=O)N(C)C)=CN2C(C)=C(C)N=C21 KABGBOMCMMYGCG-UHFFFAOYSA-N 0.000 claims description 4
- BFRZSFTYJGAIHW-UHFFFAOYSA-N 8-[(5-fluoro-3,4-dihydro-2h-chromen-4-yl)amino]-n,n,2,3-tetramethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C1COC2=CC=CC(F)=C2C1NC1=CC(C(=O)N(C)C)=CN2C(C)=C(C)N=C21 BFRZSFTYJGAIHW-UHFFFAOYSA-N 0.000 claims description 4
- DJTJCUFZBWHZNO-UHFFFAOYSA-N 8-[(8-fluoro-3,4-dihydro-2h-chromen-4-yl)amino]-n,n,2,3-tetramethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C1COC2=C(F)C=CC=C2C1NC1=CC(C(=O)N(C)C)=CN2C(C)=C(C)N=C21 DJTJCUFZBWHZNO-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- BOXZTLNZWRCSNF-UHFFFAOYSA-N 8-[(5,7-difluoro-3,4-dihydro-2h-chromen-4-yl)amino]-n-(2-hydroxyethyl)-n,2,3-trimethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C1COC2=CC(F)=CC(F)=C2C1NC1=CC(C(=O)N(CCO)C)=CN2C(C)=C(C)N=C21 BOXZTLNZWRCSNF-UHFFFAOYSA-N 0.000 claims description 2
- RWQGRHVBABJJIS-UHFFFAOYSA-N 8-[(6-fluoro-3,4-dihydro-2h-chromen-4-yl)amino]-n,n,2,3-tetramethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C1COC2=CC=C(F)C=C2C1NC1=CC(C(=O)N(C)C)=CN2C(C)=C(C)N=C21 RWQGRHVBABJJIS-UHFFFAOYSA-N 0.000 claims description 2
- HMQDURLOJGDCAJ-UHFFFAOYSA-N 8-[(7-fluoro-3,4-dihydro-2h-chromen-4-yl)amino]-n,n,2,3-tetramethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C1COC2=CC(F)=CC=C2C1NC1=CC(C(=O)N(C)C)=CN2C(C)=C(C)N=C21 HMQDURLOJGDCAJ-UHFFFAOYSA-N 0.000 claims description 2
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- 150000003018 phosphorus compounds Chemical class 0.000 claims 2
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- 239000000203 mixture Substances 0.000 abstract description 69
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- 208000029493 gastroesophageal disease Diseases 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
- 239000002904 solvent Substances 0.000 description 47
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 30
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 29
- 210000004027 cell Anatomy 0.000 description 28
- 238000009472 formulation Methods 0.000 description 26
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 26
- 238000012360 testing method Methods 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000002585 base Substances 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- 230000003287 optical effect Effects 0.000 description 16
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- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- 230000005764 inhibitory process Effects 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 10
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
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- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 9
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- 230000002285 radioactive effect Effects 0.000 description 1
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- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 1
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- 229960002052 salbutamol Drugs 0.000 description 1
- PGKXDIMONUAMFR-AREMUKBSSA-N saredutant Chemical compound C([C@H](CN(C)C(=O)C=1C=CC=CC=1)C=1C=C(Cl)C(Cl)=CC=1)CN(CC1)CCC1(NC(C)=O)C1=CC=CC=C1 PGKXDIMONUAMFR-AREMUKBSSA-N 0.000 description 1
- 229950004387 saredutant Drugs 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 description 1
- 239000000387 serotonin 5-HT4 receptor agonist Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- FBOUYBDGKBSUES-VXKWHMMOSA-N solifenacin Chemical compound C1([C@H]2C3=CC=CC=C3CCN2C(O[C@@H]2C3CCN(CC3)C2)=O)=CC=CC=C1 FBOUYBDGKBSUES-VXKWHMMOSA-N 0.000 description 1
- 229960003855 solifenacin Drugs 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 229950004825 soraprazan Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 238000003153 stable transfection Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
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- 239000003765 sweetening agent Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
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- 235000020679 tap water Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 239000006068 taste-masking agent Substances 0.000 description 1
- IKBKZGMPCYNSLU-RGVLZGJSSA-N tegaserod Chemical compound C1=C(OC)C=C2C(/C=N/NC(=N)NCCCCC)=CNC2=C1 IKBKZGMPCYNSLU-RGVLZGJSSA-N 0.000 description 1
- 229960002876 tegaserod Drugs 0.000 description 1
- 229960001114 temocillin Drugs 0.000 description 1
- BVCKFLJARNKCSS-DWPRYXJFSA-N temocillin Chemical compound N([C@]1(OC)C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C(C(O)=O)C=1C=CSC=1 BVCKFLJARNKCSS-DWPRYXJFSA-N 0.000 description 1
- 229950008375 tenatoprazole Drugs 0.000 description 1
- 229950006156 teprenone Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- TWVUMMQUXMYOOH-UHFFFAOYSA-N tilisolol Chemical compound C1=CC=C2C(=O)N(C)C=C(OCC(O)CNC(C)(C)C)C2=C1 TWVUMMQUXMYOOH-UHFFFAOYSA-N 0.000 description 1
- 229950008411 tilisolol Drugs 0.000 description 1
- LERNTVKEWCAPOY-DZZGSBJMSA-N tiotropium Chemical compound O([C@H]1C[C@@H]2[N+]([C@H](C1)[C@@H]1[C@H]2O1)(C)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 LERNTVKEWCAPOY-DZZGSBJMSA-N 0.000 description 1
- 229940110309 tiotropium Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 229960000488 tizanidine Drugs 0.000 description 1
- XFYDIVBRZNQMJC-UHFFFAOYSA-N tizanidine Chemical compound ClC=1C=CC2=NSN=C2C=1NC1=NCCN1 XFYDIVBRZNQMJC-UHFFFAOYSA-N 0.000 description 1
- OOGJQPCLVADCPB-HXUWFJFHSA-N tolterodine Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C)C=2)O)=CC=CC=C1 OOGJQPCLVADCPB-HXUWFJFHSA-N 0.000 description 1
- 229960004045 tolterodine Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000006208 topical dosage form Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 229940074410 trehalose Drugs 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 229960000859 tulobuterol Drugs 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
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- BDIAUFOIMFAIPU-UHFFFAOYSA-N valepotriate Natural products CC(C)CC(=O)OC1C=C(C(=COC2OC(=O)CC(C)C)COC(C)=O)C2C11CO1 BDIAUFOIMFAIPU-UHFFFAOYSA-N 0.000 description 1
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- 238000005303 weighing Methods 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61P1/14—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
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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)
- 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)
- Pulmonology (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63696304P | 2004-12-17 | 2004-12-17 | |
| US60/636,963 | 2004-12-17 | ||
| US69577205P | 2005-06-29 | 2005-06-29 | |
| US60/695,772 | 2005-06-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20070086294A true KR20070086294A (ko) | 2007-08-27 |
Family
ID=35995811
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020077013608A Abandoned KR20070086294A (ko) | 2004-12-17 | 2005-12-07 | 산 펌프 길항물질로 유용한 크로만 유도체 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US20090291977A1 (enExample) |
| EP (1) | EP1838309B1 (enExample) |
| JP (1) | JP2008524199A (enExample) |
| KR (1) | KR20070086294A (enExample) |
| AP (1) | AP2007004023A0 (enExample) |
| AT (1) | ATE405262T1 (enExample) |
| AU (1) | AU2005315303A1 (enExample) |
| BR (1) | BRPI0519598A2 (enExample) |
| CA (1) | CA2591412A1 (enExample) |
| DE (1) | DE602005009257D1 (enExample) |
| EA (1) | EA011512B1 (enExample) |
| ES (1) | ES2313444T3 (enExample) |
| IL (1) | IL183602A0 (enExample) |
| MA (1) | MA29095B1 (enExample) |
| MX (1) | MX2007007010A (enExample) |
| NO (1) | NO20072764L (enExample) |
| TN (1) | TNSN07227A1 (enExample) |
| WO (1) | WO2006064339A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007026218A2 (en) * | 2005-09-01 | 2007-03-08 | Pfizer Japan Inc. | Chromane substituted 2-alkyl imidazopyridine derivatives and use thereof as acid pump antagonists |
| KR20080108129A (ko) * | 2006-03-17 | 2008-12-11 | 라퀄리아 파마 인코포레이티드 | 크로메인 유도체 |
| WO2008059373A1 (en) * | 2006-11-17 | 2008-05-22 | Raqualia Pharma Inc. | Imidazo [1, 2-a] pyrazine derivatives and their use as acid pump antagonists |
| MX2016006657A (es) | 2013-11-22 | 2016-10-12 | CL BioSciences LLC | Antagonistas de gastrina (por ejemplo, yf476, netazepido) para el tratamiento y prevencion de osteoporosis. |
| JP6315708B2 (ja) * | 2015-06-22 | 2018-04-25 | 日本電信電話株式会社 | リチウム空気二次電池、リチウム空気二次電池の製造方法及びリチウム空気二次電池を備えた装置 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9801526D0 (sv) * | 1998-04-29 | 1998-04-29 | Astra Ab | New compounds |
| SE0102808D0 (sv) * | 2001-08-22 | 2001-08-22 | Astrazeneca Ab | New compounds |
| EA008304B1 (ru) * | 2002-11-19 | 2007-04-27 | Алтана Фарма Аг | 8-замещённые имидазопиридины |
-
2005
- 2005-12-07 WO PCT/IB2005/003758 patent/WO2006064339A1/en not_active Ceased
- 2005-12-07 KR KR1020077013608A patent/KR20070086294A/ko not_active Abandoned
- 2005-12-07 EA EA200701087A patent/EA011512B1/ru not_active IP Right Cessation
- 2005-12-07 US US11/721,453 patent/US20090291977A1/en not_active Abandoned
- 2005-12-07 DE DE602005009257T patent/DE602005009257D1/de not_active Expired - Fee Related
- 2005-12-07 AU AU2005315303A patent/AU2005315303A1/en not_active Abandoned
- 2005-12-07 ES ES05818222T patent/ES2313444T3/es not_active Expired - Lifetime
- 2005-12-07 JP JP2007546218A patent/JP2008524199A/ja active Pending
- 2005-12-07 BR BRPI0519598-5A patent/BRPI0519598A2/pt not_active IP Right Cessation
- 2005-12-07 EP EP05818222A patent/EP1838309B1/en not_active Expired - Lifetime
- 2005-12-07 AT AT05818222T patent/ATE405262T1/de not_active IP Right Cessation
- 2005-12-07 MX MX2007007010A patent/MX2007007010A/es unknown
- 2005-12-07 CA CA002591412A patent/CA2591412A1/en not_active Abandoned
- 2005-12-07 AP AP2007004023A patent/AP2007004023A0/xx unknown
-
2007
- 2007-05-31 IL IL183602A patent/IL183602A0/en unknown
- 2007-05-31 NO NO20072764A patent/NO20072764L/no not_active Application Discontinuation
- 2007-06-15 TN TNP2007000227A patent/TNSN07227A1/fr unknown
- 2007-06-15 MA MA29996A patent/MA29095B1/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2005315303A1 (en) | 2006-06-22 |
| NO20072764L (no) | 2007-07-03 |
| IL183602A0 (en) | 2007-09-20 |
| MA29095B1 (fr) | 2007-12-03 |
| CA2591412A1 (en) | 2006-06-22 |
| EA200701087A1 (ru) | 2008-02-28 |
| ES2313444T3 (es) | 2009-03-01 |
| EP1838309B1 (en) | 2008-08-20 |
| ATE405262T1 (de) | 2008-09-15 |
| JP2008524199A (ja) | 2008-07-10 |
| EP1838309A1 (en) | 2007-10-03 |
| BRPI0519598A2 (pt) | 2009-03-10 |
| TNSN07227A1 (fr) | 2008-11-21 |
| EA011512B1 (ru) | 2009-04-28 |
| US20090291977A1 (en) | 2009-11-26 |
| DE602005009257D1 (de) | 2008-10-02 |
| MX2007007010A (es) | 2007-07-10 |
| AP2007004023A0 (en) | 2007-06-30 |
| WO2006064339A1 (en) | 2006-06-22 |
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