IL89996A - Macrolide Compounds for the Treatment of Intestinal Disorders The process of making their new microlides - Google Patents
Macrolide Compounds for the Treatment of Intestinal Disorders The process of making their new microlidesInfo
- Publication number
- IL89996A IL89996A IL8999689A IL8999689A IL89996A IL 89996 A IL89996 A IL 89996A IL 8999689 A IL8999689 A IL 8999689A IL 8999689 A IL8999689 A IL 8999689A IL 89996 A IL89996 A IL 89996A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- formula
- alkyl
- bond
- acyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 19
- 239000003120 macrolide antibiotic agent Substances 0.000 title claims description 12
- 208000017228 Gastrointestinal motility disease Diseases 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 11
- 230000008569 process Effects 0.000 title claims description 3
- 229940041033 macrolides Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 69
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 150000005676 cyclic carbonates Chemical class 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 150000007942 carboxylates Chemical class 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 229910002651 NO3 Inorganic materials 0.000 claims description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000005228 aryl sulfonate group Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
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- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 210000003205 muscle Anatomy 0.000 description 4
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 4
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- 239000000725 suspension Substances 0.000 description 4
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- 229920000168 Microcrystalline cellulose Polymers 0.000 description 3
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- 230000003389 potentiating effect Effects 0.000 description 3
- 125000006412 propinylene group Chemical group [H]C#CC([H])([H])* 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
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- 230000032258 transport Effects 0.000 description 3
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- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- JFVYXJKGJMUGRG-KJPZRSJGSA-N Erythromycin a enol ether Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C2=C(C)C[C@](O2)(C)[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 JFVYXJKGJMUGRG-KJPZRSJGSA-N 0.000 description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 2
- 206010021333 Ileus paralytic Diseases 0.000 description 2
- 241000315040 Omura Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
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- TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 description 2
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
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- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229960000829 kaolin Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229960001375 lactose Drugs 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 210000000111 lower esophageal sphincter Anatomy 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229960001855 mannitol Drugs 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003149 muscarinic antagonist Substances 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 230000001769 paralizing effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000007310 pathophysiology Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229940097325 prolactin Drugs 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229960002668 sodium chloride Drugs 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 229960000999 sodium citrate dihydrate Drugs 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CFMYXEVWODSLAX-QOZOJKKESA-N tetrodotoxin Chemical compound O([C@@]([C@H]1O)(O)O[C@H]2[C@@]3(O)CO)[C@H]3[C@@H](O)[C@]11[C@H]2[C@@H](O)N=C(N)N1 CFMYXEVWODSLAX-QOZOJKKESA-N 0.000 description 1
- 229950010357 tetrodotoxin Drugs 0.000 description 1
- CFMYXEVWODSLAX-UHFFFAOYSA-N tetrodotoxin Natural products C12C(O)NC(=N)NC2(C2O)C(O)C3C(CO)(O)C1OC2(O)O3 CFMYXEVWODSLAX-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- 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
-
- 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
- A61P1/12—Antidiarrhoeals
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Nutrition Science (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/182,645 US4920102A (en) | 1988-04-18 | 1988-04-18 | Method for treating gastrointestinal disorders |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL89996A0 IL89996A0 (en) | 1989-12-15 |
| IL89996A true IL89996A (en) | 1994-08-26 |
Family
ID=22669415
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL8999689A IL89996A (en) | 1988-04-18 | 1989-04-17 | Macrolide Compounds for the Treatment of Intestinal Disorders The process of making their new microlides |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4920102A (pt) |
| EP (1) | EP0349100B1 (pt) |
| JP (1) | JPH0825882B2 (pt) |
| KR (1) | KR970009580B1 (pt) |
| CN (1) | CN1023017C (pt) |
| AR (1) | AR244699A1 (pt) |
| AT (1) | ATE139782T1 (pt) |
| AU (1) | AU616746B2 (pt) |
| CA (1) | CA1328257C (pt) |
| DE (1) | DE68926728T2 (pt) |
| DK (1) | DK183589A (pt) |
| ES (1) | ES2088388T3 (pt) |
| GR (1) | GR3020604T3 (pt) |
| HU (1) | HU206365B (pt) |
| IE (1) | IE72969B1 (pt) |
| IL (1) | IL89996A (pt) |
| MX (1) | MX15701A (pt) |
| NZ (1) | NZ228768A (pt) |
| PH (1) | PH26391A (pt) |
| PT (1) | PT90293B (pt) |
| RU (1) | RU2086560C1 (pt) |
| ZA (1) | ZA892801B (pt) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5106961A (en) * | 1987-05-26 | 1992-04-21 | Eli Lilly And Company | Erythromycin ring-contracted derivatives |
| US5068221A (en) * | 1989-05-09 | 1991-11-26 | Mathias John R | Treatment of motility disorders with a gnrh analog |
| US5434136A (en) * | 1990-12-14 | 1995-07-18 | Mathias; John R. | Treatment of motility disorders with a GNRH analog |
| US5523418A (en) * | 1991-04-09 | 1996-06-04 | Abbott Laboratories | Macrocyclic lactam prokinetic agents |
| DE69211845T2 (de) * | 1991-04-09 | 1997-01-23 | Abbott Lab | Macrozyklische laktam-prokinetika |
| DE4200145A1 (de) * | 1992-01-07 | 1993-07-08 | Kali Chemie Pharma Gmbh | 7,10-epoxy-oxacyclododecan-derivate, verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| WO1993013780A1 (en) * | 1992-01-21 | 1993-07-22 | Abbott Laboratories | 4''-deoxyerythromycin derivatives |
| CA2092045C (en) * | 1992-03-19 | 2004-08-10 | Setsuo Harada | Erythromycin derivatives, preparation and use thereof |
| FR2697524B1 (fr) * | 1992-11-05 | 1994-12-23 | Roussel Uclaf | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
| US5712253A (en) * | 1996-06-18 | 1998-01-27 | Abbott Laboratories | Macrocyclic 13-membered ring derivatives of erythromycins A and B |
| DE19644195A1 (de) * | 1996-10-24 | 1998-04-30 | Solvay Pharm Gmbh | 10,13,15-Trioxatricyclo[9.2.1.1.·9·.·6·]-pentadecanon-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US6165985A (en) * | 1998-02-13 | 2000-12-26 | Solvay Pharmaceuticals Gmbh | 11-acetyl-12,13-dioxabicyclo[8.2.1]-tridecenone derivatives, processes for their preparation and pharmaceutical compositions comprising them |
| DE19805822B4 (de) * | 1998-02-13 | 2009-02-05 | Solvay Pharmaceuticals Gmbh | 11-Acetyl-12,13-dioxabicyclo[8.2.1]tridecenon-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US5955440A (en) * | 1998-03-27 | 1999-09-21 | Abbott Laboratories | Macrolide LHRH antagonists |
| US5972898A (en) * | 1998-03-27 | 1999-10-26 | Abbott Laboratories | 3',3-N-bis-substituted macrolide LHRH antagonists |
| US6387885B1 (en) | 1998-08-26 | 2002-05-14 | Abbott Laboratories | 3′,3′-N-bis-desmethyl-3′-N-cycloalkyl erythromycin derivatives as LHRH antagonists |
| US6020521A (en) * | 1998-08-26 | 2000-02-01 | Abbott Laboratories | Macrolide LHRH antagonists |
| US6451806B2 (en) | 1999-09-29 | 2002-09-17 | Adolor Corporation | Methods and compositions involving opioids and antagonists thereof |
| US6469030B2 (en) | 1999-11-29 | 2002-10-22 | Adolor Corporation | Methods for the treatment and prevention of ileus |
| WO2002014338A1 (fr) * | 2000-08-17 | 2002-02-21 | The Kitasato Institute | Nouveaux derives de pseudoerythromycine |
| GB0123400D0 (en) * | 2001-09-28 | 2001-11-21 | Novartis Ag | Organic compounds |
| RU2202351C1 (ru) * | 2001-11-29 | 2003-04-20 | Дальневосточный государственный медицинский университет | Способ коррекции гастропареза после органосохраняющих операций на желудке |
| US20040067896A1 (en) * | 2002-07-25 | 2004-04-08 | The Kitasato Institute | Novel pseudoerythromycin derivatives |
| JP4440108B2 (ja) * | 2002-10-29 | 2010-03-24 | 学校法人北里研究所 | 抗真菌活性増強作用を有する新規マクロライド誘導体 |
| DE602004025569D1 (de) | 2003-06-18 | 2010-04-01 | Tranzyme Pharma Inc | Makrozyklische motilin rezeptorantagonisten |
| BRPI0619556A2 (pt) * | 2005-12-08 | 2011-10-04 | Pfizer | processo para desmetilação de grupo 3' -dimetil amino de compostos eritromicina |
| JP5684474B2 (ja) | 2006-09-11 | 2015-03-11 | オセラ セラピューティクス， インコーポレイテッド | 胃腸の運動障害疾患の治療のためのモチリン受容体の大環状アンタゴニスト |
| US20080287371A1 (en) * | 2007-05-17 | 2008-11-20 | Tranzyme Pharma Inc. | Macrocyclic antagonists of the motilin receptor for modulation of the migrating motor complex |
| FR2995605B1 (fr) * | 2012-09-18 | 2014-09-19 | Sanofi Sa | Derives de macrolides, leur preparation et leur application therapeutique. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4547491A (en) * | 1984-07-18 | 1985-10-15 | Merck & Co., Inc. | C-8A-Oxo-avermectin and milbemycin derivatives, pharmaceutical compositions and method of use |
| JPS6187625A (ja) * | 1984-10-05 | 1986-05-06 | Satoshi Omura | 消化管収縮運動促進剤 |
| DE3689758T2 (de) * | 1985-08-31 | 1994-08-18 | Kitasato Inst | Erythromycinderivat und Verfahren zu dessen Herstellung. |
| CA1321581C (en) * | 1987-05-26 | 1993-08-24 | Herbert A. Kirst | Ring-contracted macrolides |
-
1988
- 1988-04-18 US US07/182,645 patent/US4920102A/en not_active Expired - Lifetime
-
1989
- 1989-04-17 IL IL8999689A patent/IL89996A/en not_active IP Right Cessation
- 1989-04-17 PH PH38516A patent/PH26391A/en unknown
- 1989-04-17 NZ NZ228768A patent/NZ228768A/xx unknown
- 1989-04-17 IE IE122489A patent/IE72969B1/en not_active IP Right Cessation
- 1989-04-17 CA CA000596863A patent/CA1328257C/en not_active Expired - Fee Related
- 1989-04-17 HU HU891879A patent/HU206365B/hu not_active IP Right Cessation
- 1989-04-17 AR AR89313685A patent/AR244699A1/es active
- 1989-04-17 DK DK183589A patent/DK183589A/da not_active Application Discontinuation
- 1989-04-17 AU AU33107/89A patent/AU616746B2/en not_active Ceased
- 1989-04-17 ZA ZA892801A patent/ZA892801B/xx unknown
- 1989-04-17 PT PT90293A patent/PT90293B/pt not_active IP Right Cessation
- 1989-04-18 CN CN89102358A patent/CN1023017C/zh not_active Expired - Fee Related
- 1989-04-18 MX MX1570189A patent/MX15701A/es unknown
- 1989-04-18 DE DE68926728T patent/DE68926728T2/de not_active Expired - Fee Related
- 1989-04-18 KR KR89005088A patent/KR970009580B1/ko not_active Expired - Fee Related
- 1989-04-18 JP JP1099889A patent/JPH0825882B2/ja not_active Expired - Lifetime
- 1989-04-18 AT AT89303813T patent/ATE139782T1/de not_active IP Right Cessation
- 1989-04-18 ES ES89303813T patent/ES2088388T3/es not_active Expired - Lifetime
- 1989-04-18 EP EP89303813A patent/EP0349100B1/en not_active Expired - Lifetime
-
1992
- 1992-08-04 RU SU925052262A patent/RU2086560C1/ru active
-
1996
- 1996-07-23 GR GR960401963T patent/GR3020604T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0825882B2 (ja) | 1996-03-13 |
| PT90293A (pt) | 1989-11-10 |
| IE891224L (en) | 1989-10-18 |
| DE68926728T2 (de) | 1996-11-28 |
| RU2086560C1 (ru) | 1997-08-10 |
| NZ228768A (en) | 1990-10-26 |
| AU3310789A (en) | 1989-10-19 |
| GR3020604T3 (en) | 1996-10-31 |
| AU616746B2 (en) | 1991-11-07 |
| US4920102A (en) | 1990-04-24 |
| ATE139782T1 (de) | 1996-07-15 |
| ES2088388T3 (es) | 1996-08-16 |
| PH26391A (en) | 1992-07-02 |
| PT90293B (pt) | 1994-07-29 |
| IL89996A0 (en) | 1989-12-15 |
| HUT49625A (en) | 1989-10-30 |
| KR900016220A (ko) | 1990-11-12 |
| EP0349100A2 (en) | 1990-01-03 |
| ZA892801B (en) | 1990-12-28 |
| EP0349100B1 (en) | 1996-06-26 |
| MX15701A (es) | 1993-11-01 |
| CN1023017C (zh) | 1993-12-08 |
| IE72969B1 (en) | 1997-05-07 |
| JPH01311096A (ja) | 1989-12-15 |
| EP0349100A3 (en) | 1991-11-13 |
| DK183589A (da) | 1989-10-19 |
| DE68926728D1 (de) | 1996-08-01 |
| CN1037517A (zh) | 1989-11-29 |
| KR970009580B1 (en) | 1997-06-14 |
| DK183589D0 (da) | 1989-04-17 |
| CA1328257C (en) | 1994-04-05 |
| AR244699A1 (es) | 1993-11-30 |
| HU206365B (en) | 1992-10-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RH | Patent void |