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)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (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 |
| ATE139697T1 (de) * | 1991-04-09 | 1996-07-15 | Abbott Lab | Macrozyklische laktam-prokinetika |
| US5554605A (en) * | 1991-04-09 | 1996-09-10 | Abbott Laboratories | Macrocyclic lactam prokinetic agents |
| 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 |
| DE69317877T2 (de) * | 1992-01-21 | 1998-10-29 | Abbott Lab | 4''-deoxyerythromycinderivate |
| DE69302938T2 (de) * | 1992-03-19 | 1996-10-17 | Kitasato Inst | Erythromycinderivate, Herstellung und Verwendung davon |
| 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 |
| US6020521A (en) * | 1998-08-26 | 2000-02-01 | Abbott Laboratories | 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 |
| 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 |
| CA2386828C (en) | 2000-08-17 | 2006-01-24 | The Kitasato Institute | Novel pseudoerythromycin derivatives |
| 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 |
| WO2004039823A1 (ja) * | 2002-10-29 | 2004-05-13 | The Kitasato Institute | 抗真菌活性増強作用を有する新規マクロライド誘導体 |
| CA2528375C (en) | 2003-06-18 | 2013-11-19 | Tranzyme Pharma, Inc. | Macrocyclic antagonists of the motilin receptor |
| NZ568763A (en) * | 2005-12-08 | 2010-04-30 | Pfizer | Method for demethylating the 3'-dimethylamino group of erythromycin compounds |
| EP2431380A3 (en) | 2006-09-11 | 2013-07-03 | Tranzyme Pharma, Inc. | Macrocyclic antagonist of the motilin receptor for treatment of gastrointestinal dysmotility disorders |
| 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 |
| EP0215355B1 (en) * | 1985-08-31 | 1994-04-06 | Kitasato Kenkyusho | Erythromycin derivative and process for preparing the same |
| 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 PT PT90293A patent/PT90293B/pt not_active IP Right Cessation
- 1989-04-17 CA CA000596863A patent/CA1328257C/en not_active Expired - Fee Related
- 1989-04-17 NZ NZ228768A patent/NZ228768A/xx unknown
- 1989-04-17 AU AU33107/89A patent/AU616746B2/en not_active Ceased
- 1989-04-17 IL IL8999689A patent/IL89996A/en not_active IP Right Cessation
- 1989-04-17 DK DK183589A patent/DK183589A/da not_active Application Discontinuation
- 1989-04-17 ZA ZA892801A patent/ZA892801B/xx unknown
- 1989-04-17 IE IE122489A patent/IE72969B1/en not_active IP Right Cessation
- 1989-04-17 AR AR89313685A patent/AR244699A1/es active
- 1989-04-17 PH PH38516A patent/PH26391A/en unknown
- 1989-04-17 HU HU891879A patent/HU206365B/hu not_active IP Right Cessation
- 1989-04-18 DE DE68926728T patent/DE68926728T2/de not_active Expired - Fee Related
- 1989-04-18 MX MX1570189A patent/MX15701A/es unknown
- 1989-04-18 JP JP1099889A patent/JPH0825882B2/ja not_active Expired - Lifetime
- 1989-04-18 KR KR89005088A patent/KR970009580B1/ko not_active Expired - Fee Related
- 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 CN CN89102358A patent/CN1023017C/zh not_active Expired - Fee Related
- 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 |
|---|---|
| ZA892801B (en) | 1990-12-28 |
| DE68926728D1 (de) | 1996-08-01 |
| AU616746B2 (en) | 1991-11-07 |
| EP0349100A3 (en) | 1991-11-13 |
| DK183589D0 (da) | 1989-04-17 |
| US4920102A (en) | 1990-04-24 |
| IE891224L (en) | 1989-10-18 |
| IL89996A0 (en) | 1989-12-15 |
| PH26391A (en) | 1992-07-02 |
| AR244699A1 (es) | 1993-11-30 |
| GR3020604T3 (en) | 1996-10-31 |
| RU2086560C1 (ru) | 1997-08-10 |
| KR970009580B1 (en) | 1997-06-14 |
| MX15701A (es) | 1993-11-01 |
| KR900016220A (ko) | 1990-11-12 |
| PT90293B (pt) | 1994-07-29 |
| CA1328257C (en) | 1994-04-05 |
| DK183589A (da) | 1989-10-19 |
| CN1037517A (zh) | 1989-11-29 |
| EP0349100B1 (en) | 1996-06-26 |
| ATE139782T1 (de) | 1996-07-15 |
| JPH0825882B2 (ja) | 1996-03-13 |
| PT90293A (pt) | 1989-11-10 |
| ES2088388T3 (es) | 1996-08-16 |
| EP0349100A2 (en) | 1990-01-03 |
| IE72969B1 (en) | 1997-05-07 |
| AU3310789A (en) | 1989-10-19 |
| CN1023017C (zh) | 1993-12-08 |
| DE68926728T2 (de) | 1996-11-28 |
| JPH01311096A (ja) | 1989-12-15 |
| HU206365B (en) | 1992-10-28 |
| HUT49625A (en) | 1989-10-30 |
| NZ228768A (en) | 1990-10-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RH | Patent void |