JPH06509326A - 大環式ラクタムプロキネティック剤 - Google Patents

大環式ラクタムプロキネティック剤

Info

Publication number: JPH06509326A
Authority: JP; Japan
Prior art keywords: methyl; oxy; hexamethyl; ethyl; trideoxy
Prior art date: 1991-04-09
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.): Pending

Application number

JP4511370A

Other languages

English (en)

Japanese (ja)

Inventor

フレイバーグ，レスリー・エイ

エドワーズ，カーラ

パリザ，リチヤード・ジエイ

ネランス，ヒユー・エヌ

Original Assignee

アボツト・ラボラトリーズ

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1991-04-09

Filing date

1992-03-30

Publication date

1994-10-20

1992-03-30 Application filed by アボツト・ラボラトリーズ filed Critical アボツト・ラボラトリーズ

1994-10-20 Publication of JPH06509326A publication Critical patent/JPH06509326A/ja

Status Pending legal-status Critical Current

Links

150000003951 lactams Chemical class 0.000 title claims description 11
239000002325 prokinetic agent Substances 0.000 title description 11
150000001875 compounds Chemical class 0.000 claims description 142
-1 erythromycin D lactam enol ether Chemical class 0.000 claims description 41
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 claims description 37
229910052739 hydrogen Inorganic materials 0.000 claims description 35
239000001257 hydrogen Substances 0.000 claims description 35
QIVRQFJRUABARQ-UHFFFAOYSA-N pentadec-14-en-7-one Chemical compound CCCCCCC(=O)CCCCCCC=C QIVRQFJRUABARQ-UHFFFAOYSA-N 0.000 claims description 33
239000000126 substance Substances 0.000 claims description 32
125000000217 alkyl group Chemical group 0.000 claims description 30
229960003276 erythromycin Drugs 0.000 claims description 28
238000000034 method Methods 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 20
229930006677 Erythromycin A Natural products 0.000 claims description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
QBEKGNIWIHIMOM-UHFFFAOYSA-N tridec-12-en-5-one Chemical compound CCCCC(=O)CCCCCCC=C QBEKGNIWIHIMOM-UHFFFAOYSA-N 0.000 claims description 11
150000002118 epoxides Chemical class 0.000 claims description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
125000003132 pyranosyl group Chemical group 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 5
125000001589 carboacyl group Chemical group 0.000 claims description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
150000005676 cyclic carbonates Chemical class 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
238000007363 ring formation reaction Methods 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 2
125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 2
238000007142 ring opening reaction Methods 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
229910021386 carbon form Inorganic materials 0.000 claims 1
150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
230000002269 spontaneous effect Effects 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 195
239000000243 solution Substances 0.000 description 124
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 118
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 105
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 94
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 58
239000000203 mixture Substances 0.000 description 58
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 54
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 52
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
239000011541 reaction mixture Substances 0.000 description 47
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
239000000047 product Substances 0.000 description 34
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 31
239000012267 brine Substances 0.000 description 30
235000017557 sodium bicarbonate Nutrition 0.000 description 29
229910000030 sodium bicarbonate Inorganic materials 0.000 description 29
238000006243 chemical reaction Methods 0.000 description 28
239000010410 layer Substances 0.000 description 28
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 26
235000011114 ammonium hydroxide Nutrition 0.000 description 26
239000000908 ammonium hydroxide Substances 0.000 description 25
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 24
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 24
229960000583 acetic acid Drugs 0.000 description 22
239000002904 solvent Substances 0.000 description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
239000012044 organic layer Substances 0.000 description 17
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
239000000741 silica gel Substances 0.000 description 15
229910002027 silica gel Inorganic materials 0.000 description 15
239000002253 acid Substances 0.000 description 14
239000002585 base Substances 0.000 description 14
238000010992 reflux Methods 0.000 description 14
229940079593 drug Drugs 0.000 description 13
239000003814 drug Substances 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
229910021529 ammonia Inorganic materials 0.000 description 12
239000003054 catalyst Substances 0.000 description 12
239000003921 oil Substances 0.000 description 12
235000019198 oils Nutrition 0.000 description 12
238000003756 stirring Methods 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
239000012043 crude product Substances 0.000 description 11
238000001914 filtration Methods 0.000 description 11
230000008602 contraction Effects 0.000 description 10
239000012362 glacial acetic acid Substances 0.000 description 10
210000002784 stomach Anatomy 0.000 description 10
238000012360 testing method Methods 0.000 description 10
238000004458 analytical method Methods 0.000 description 9
239000007864 aqueous solution Substances 0.000 description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
208000035475 disorder Diseases 0.000 description 9
235000019441 ethanol Nutrition 0.000 description 9
239000000463 material Substances 0.000 description 9
230000004899 motility Effects 0.000 description 9
125000001736 nosyl group Chemical group S(=O)(=O)(C1=CC=C([N+](=O)[O-])C=C1)* 0.000 description 9
239000007787 solid Substances 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
238000004364 calculation method Methods 0.000 description 8
235000008504 concentrate Nutrition 0.000 description 8
239000012141 concentrate Substances 0.000 description 8
239000011521 glass Substances 0.000 description 8
210000003127 knee Anatomy 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
239000011734 sodium Substances 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
239000000725 suspension Substances 0.000 description 8
IDRYSCOQVVUBIJ-UHFFFAOYSA-N Erythromycin-B Natural products CC1C(OC2C(C(CC(C)O2)N(C)C)O)C(C)(O)CC(C)C(=O)C(C)C(O)C(C)C(CC)OC(=O)C(C)C1OC1CC(C)(OC)C(O)C(C)O1 IDRYSCOQVVUBIJ-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
238000009472 formulation Methods 0.000 description 7
230000002496 gastric effect Effects 0.000 description 7
238000000746 purification Methods 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 6
239000005695 Ammonium acetate Substances 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
235000019257 ammonium acetate Nutrition 0.000 description 6
229940043376 ammonium acetate Drugs 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
238000000576 coating method Methods 0.000 description 6
JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 6
231100000673 dose–response relationship Toxicity 0.000 description 6
239000000284 extract Substances 0.000 description 6
229910052740 iodine Inorganic materials 0.000 description 6
239000011630 iodine Substances 0.000 description 6
210000003205 muscle Anatomy 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
150000001350 alkyl halides Chemical class 0.000 description 5
239000013078 crystal Substances 0.000 description 5
210000001198 duodenum Anatomy 0.000 description 5
210000003238 esophagus Anatomy 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
235000013305 food Nutrition 0.000 description 5
210000001035 gastrointestinal tract Anatomy 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
229940099584 lactobionate Drugs 0.000 description 5
JYTUSYBCFIZPBE-AMTLMPIISA-N lactobionic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-N 0.000 description 5
230000009467 reduction Effects 0.000 description 5
230000004044 response Effects 0.000 description 5
238000003860 storage Methods 0.000 description 5
210000001519 tissue Anatomy 0.000 description 5
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
244000025254 Cannabis sativa Species 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
MWFRKHPRXPSWNT-UHFFFAOYSA-N Erythromycin-C Natural products CC1C(OC2C(C(CC(C)O2)N(C)C)O)C(C)(O)CC(C)C(=O)C(C)C(O)C(O)(C)C(CC)OC(=O)C(C)C1OC1CC(C)(O)C(O)C(C)O1 MWFRKHPRXPSWNT-UHFFFAOYSA-N 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
206010021518 Impaired gastric emptying Diseases 0.000 description 4
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
230000009102 absorption Effects 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 4
230000008859 change Effects 0.000 description 4
230000001684 chronic effect Effects 0.000 description 4
229940125782 compound 2 Drugs 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
230000018044 dehydration Effects 0.000 description 4
238000006297 dehydration reaction Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000010828 elution Methods 0.000 description 4
IDRYSCOQVVUBIJ-PPGFLMPOSA-N erythromycin B Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@H]([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)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 IDRYSCOQVVUBIJ-PPGFLMPOSA-N 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000006260 foam Substances 0.000 description 4
230000005176 gastrointestinal motility Effects 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
208000003243 intestinal obstruction Diseases 0.000 description 4
239000007788 liquid Substances 0.000 description 4
230000033001 locomotion Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
231100000252 nontoxic Toxicity 0.000 description 4
230000003000 nontoxic effect Effects 0.000 description 4
239000012071 phase Substances 0.000 description 4
239000006187 pill Substances 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
210000000813 small intestine Anatomy 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000003826 tablet Substances 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
238000005406 washing Methods 0.000 description 4
ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
206010010774 Constipation Diseases 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Polymers OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 3
241000124008 Mammalia Species 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
239000004698 Polyethylene Substances 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
239000007868 Raney catalyst Substances 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
229910052776 Thorium Inorganic materials 0.000 description 3
206010047700 Vomiting Diseases 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
229940100198 alkylating agent Drugs 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 3
239000002775 capsule Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
229960005215 dichloroacetic acid Drugs 0.000 description 3
PBWZKZYHONABLN-UHFFFAOYSA-N difluoroacetic acid Chemical compound OC(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
238000001647 drug administration Methods 0.000 description 3
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VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
239000000347 magnesium hydroxide Substances 0.000 description 1
229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
230000001071 malnutrition Effects 0.000 description 1
235000000824 malnutrition Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
239000000155 melt Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
230000003183 myoelectrical effect Effects 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000008693 nausea Effects 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
208000015380 nutritional deficiency disease Diseases 0.000 description 1
229940049964 oleate Drugs 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
235000021542 oral nutrition Nutrition 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000000242 pagocytic effect Effects 0.000 description 1
230000036407 pain Effects 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
VUXXXYMMZBAUSE-UHFFFAOYSA-N pentadecan-7-one Chemical compound CCCCCCCCC(=O)CCCCCC VUXXXYMMZBAUSE-UHFFFAOYSA-N 0.000 description 1
208000000689 peptic esophagitis Diseases 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
239000008055 phosphate buffer solution Substances 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
230000002980 postoperative effect Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 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
239000003755 preservative agent Substances 0.000 description 1
230000008569 process Effects 0.000 description 1
238000012545 processing Methods 0.000 description 1
229940097325 prolactin Drugs 0.000 description 1
230000001141 propulsive effect Effects 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
229910052705 radium Inorganic materials 0.000 description 1
HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 1
239000003087 receptor blocking agent Substances 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
238000004007 reversed phase HPLC Methods 0.000 description 1
235000005713 safflower oil Nutrition 0.000 description 1
239000003813 safflower oil Substances 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000007790 scraping Methods 0.000 description 1
238000012216 screening Methods 0.000 description 1
238000007423 screening assay Methods 0.000 description 1
238000007789 sealing Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
210000002151 serous membrane Anatomy 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
230000016160 smooth muscle contraction Effects 0.000 description 1
AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
JGFYQVQAXANWJU-UHFFFAOYSA-M sodium fluoroacetate Chemical compound [Na+].[O-]C(=O)CF JGFYQVQAXANWJU-UHFFFAOYSA-M 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
229940114926 stearate Drugs 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000000021 stimulant Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000010902 straw Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
YALHCTUQSQRCSX-UHFFFAOYSA-N sulfane sulfuric acid Chemical compound S.OS(O)(=O)=O YALHCTUQSQRCSX-UHFFFAOYSA-N 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 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
230000002194 synthesizing effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000002627 tracheal intubation Methods 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical class CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
210000002438 upper gastrointestinal tract Anatomy 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
230000004580 weight loss Effects 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
210000002417 xiphoid bone Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Polyamides (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Cephalosporin Compounds (AREA)
Hydrogenated Pyridines (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

JP4511370A 1991-04-09 1992-03-30 大環式ラクタムプロキネティック剤 Pending JPH06509326A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US68283691A	1991-04-09	1991-04-09
US682,836		1991-04-09
PCT/US1992/002590 WO1992018134A1 (en)	1991-04-09	1992-03-30	Macrocyclic lactam prokinetic agents

Publications (1)

Publication Number	Publication Date
JPH06509326A true JPH06509326A (ja)	1994-10-20

Family

ID=24741372

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP4511370A Pending JPH06509326A (ja)	1991-04-09	1992-03-30	大環式ラクタムプロキネティック剤

Country Status (15)

Country	Link
US (1)	US5538961A (2)
EP (1)	EP0579770B1 (2)
JP (1)	JPH06509326A (2)
KR (1)	KR100222014B1 (2)
AT (1)	ATE139697T1 (2)
AU (1)	AU663089B2 (2)
CA (1)	CA2103913A1 (2)
DE (1)	DE69211845T2 (2)
DK (1)	DK0579770T3 (2)
ES (1)	ES2091471T3 (2)
GR (1)	GR3020853T3 (2)
IE (1)	IE73236B1 (2)
IL (1)	IL101504A (2)
PT (1)	PT100357B (2)
WO (1)	WO1992018134A1 (2)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1122261A3 (en) *	2000-01-31	2001-09-26	Pfizer Products Inc.	13 and 14-membered antibacterial macrolides
CA2399198A1 (en)	2000-02-18	2001-08-23	Christopher Carreras	Motilide compounds
ATE321770T1 (de)	2000-08-17	2006-04-15	Kitasato Inst	Pseudoerythromycin-derivate
AU2002225724A1 (en) *	2000-12-01	2002-07-08	Kosan Biosciences, Inc.	Motilide compounds
US20020094962A1 (en) *	2000-12-01	2002-07-18	Gary Ashley	Motilide compounds
ES2316805T3 (es) *	2002-08-29	2009-04-16	Pfizer Inc.	Compuestos motilidos.
EP1536841A1 (en) *	2002-09-12	2005-06-08	The University of Chicago	Monitoring and diagnosis of gastric emptying and gastroparesis
US7521420B2 (en)	2003-06-18	2009-04-21	Tranzyme Pharma, Inc.	Macrocyclic antagonists of the motilin receptor
US20050113319A1 (en) *	2003-08-26	2005-05-26	Christopher Carreras	11-Deoxy-6,9-ether erythromycin compounds
US7407941B2 (en) *	2003-08-26	2008-08-05	Pfizer, Inc.	N-desmethyl-N-substituted-11-deoxyerythromycin compounds
US7211568B2 (en) *	2003-12-18	2007-05-01	Kosan Biosciences Incorporated	9-Desoxoerythromycin compounds as prokinetic agents
US7582611B2 (en) *	2005-05-24	2009-09-01	Pfizer Inc.	Motilide compounds
JP2009518396A (ja) *	2005-12-08	2009-05-07	ファイザー・インク	エリスロマイシン化合物の３’−ジメチルアミノ基を脱メチルする方法
EP2054429B1 (en)	2006-09-11	2013-11-06	Tranzyme Pharma, Inc.	Macrocyclic antagonists of the motilin receptor for treatment of gastrointestinal dysmotility disorders
KR101120483B1 (ko) *	2006-12-05	2012-02-29	브리스톨-마이어즈 스퀴브 컴페니	모틸라이드 다형체
US20080287371A1 (en) *	2007-05-17	2008-11-20	Tranzyme Pharma Inc.	Macrocyclic antagonists of the motilin receptor for modulation of the migrating motor complex
ES2609845T3 (es) *	2011-07-29	2017-04-24	Cambridge Epigenetix Limited	Métodos para la detección de modificación de nucleótidos
ES2669512T3 (es)	2012-11-30	2018-05-28	Cambridge Epigenetix Limited	Agente oxidante para nucleótidos modificados
CN115057794B (zh) *	2022-07-07	2023-11-17	桂林理工大学	一种可见光诱导铈催化氧化酰胺去甲基化的方法

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4512982A (en) *	1984-04-13	1985-04-23	Pfizer Inc.	9α-Aza-9α-homoerythromycin compounds, pharmaceutical composition and therapeutic method
US4518590A (en) *	1984-04-13	1985-05-21	Pfizer Inc.	9α-Aza-9α-homoerythromycin compounds, pharmaceutical compositions and therapeutic method
US5008249A (en) *	1985-08-31	1991-04-16	Kitasato Kenkyusho	Therapeutic method of stimulating digestive tract contractile motion in mammals
EP0215355B1 (en) *	1985-08-31	1994-04-06	Kitasato Kenkyusho	Erythromycin derivative and process for preparing the same
US5106961A (en) *	1987-05-26	1992-04-21	Eli Lilly And Company	Erythromycin ring-contracted derivatives
US4958010A (en) *	1988-02-16	1990-09-18	Bristol-Myers Company	Epipodophyllotoxin glucoside lactam derivatives
US4920102A (en) *	1988-04-18	1990-04-24	Eli Lilly And Company	Method for treating gastrointestinal disorders
US5202434A (en) *	1991-04-05	1993-04-13	Merck & Co., Inc.	8a-aza-8a-homoerythromycin lactams
US5189159A (en) *	1992-04-02	1993-02-23	Merck & Co., Inc.	8a-AZA-8a-homoerythromycin cyclic iminoethers

1992
- 1992-03-30 CA CA002103913A patent/CA2103913A1/en not_active Abandoned
- 1992-03-30 AT AT92911585T patent/ATE139697T1/de not_active IP Right Cessation
- 1992-03-30 WO PCT/US1992/002590 patent/WO1992018134A1/en not_active Ceased
- 1992-03-30 DK DK92911585.5T patent/DK0579770T3/da active
- 1992-03-30 EP EP92911585A patent/EP0579770B1/en not_active Expired - Lifetime
- 1992-03-30 JP JP4511370A patent/JPH06509326A/ja active Pending
- 1992-03-30 DE DE69211845T patent/DE69211845T2/de not_active Expired - Fee Related
- 1992-03-30 KR KR1019930703026A patent/KR100222014B1/ko not_active Expired - Fee Related
- 1992-03-30 AU AU19103/92A patent/AU663089B2/en not_active Ceased
- 1992-03-30 US US08/108,659 patent/US5538961A/en not_active Expired - Fee Related
- 1992-03-30 ES ES92911585T patent/ES2091471T3/es not_active Expired - Lifetime
- 1992-04-02 IE IE921045A patent/IE73236B1/en not_active IP Right Cessation
- 1992-04-06 IL IL101504A patent/IL101504A/en not_active IP Right Cessation
- 1992-04-08 PT PT100357A patent/PT100357B/pt not_active IP Right Cessation
1996
- 1996-08-22 GR GR960402210T patent/GR3020853T3/el unknown

Also Published As

Publication number	Publication date
PT100357B (pt)	1999-06-30
DE69211845T2 (de)	1997-01-23
ATE139697T1 (de)	1996-07-15
AU663089B2 (en)	1995-09-28
DE69211845D1 (de)	1996-08-01
CA2103913A1 (en)	1992-10-10
US5538961A (en)	1996-07-23
IE921045A1 (en)	1992-10-21
EP0579770A1 (en)	1994-01-26
DK0579770T3 (da)	1996-11-04
KR100222014B1 (ko)	1999-10-01
AU1910392A (en)	1992-11-17
ES2091471T3 (es)	1996-11-01
IE73236B1 (en)	1997-05-21
EP0579770A4 (2)	1994-03-30
IL101504A (en)	1998-04-05
EP0579770B1 (en)	1996-06-26
GR3020853T3 (en)	1996-11-30
WO1992018134A1 (en)	1992-10-29
IL101504A0 (en)	1992-12-30
PT100357A (pt)	1993-07-30

Publication	Publication Date	Title
JPH06509326A (ja)	1994-10-20	大環式ラクタムプロキネティック剤
KR0166996B1 (ko)	1999-01-15	5-o-데소사미닐에리쓰로노라이드a 유도체
US5712253A (en)	1998-01-27	Macrocyclic 13-membered ring derivatives of erythromycins A and B
EP0349100B1 (en)	1996-06-26	Macrolide compositions for treating gastro-intestinal motility disorders
US5834438A (en)	1998-11-10	4"-deoxyerythromycin derivatives
JPH05504944A (ja)	1993-07-29	巨大環式化合物
HK1010054B (en)	1999-06-11	4"-deoxyerythromycin derivatives
US5554605A (en)	1996-09-10	Macrocyclic lactam prokinetic agents
FI106862B (fi)	2001-04-30	Menetelmä 4,13-dioksabisyklo[8.2.1]tridekenonijohdannaisten ja niiden välituotteiden valmistamiseksi
JPH10130297A (ja)	1998-05-19	エリスロマイシンａの環縮小ｎ−デスメチル−ｎ−イソプロピルスピロアセタール誘導体、その製法及びこの化合物を含有する医薬
KR900008676B1 (ko)	1990-11-26	항균성 9-데옥소-9a-알릴 및 프로파길-9a-아자-9a-호모에리트로마이신 A유도체
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