CA2601640C - Use of macrolides for treating intestinal inflammation - Google Patents
Use of macrolides for treating intestinal inflammation Download PDFInfo
- Publication number
- CA2601640C CA2601640C CA2601640A CA2601640A CA2601640C CA 2601640 C CA2601640 C CA 2601640C CA 2601640 A CA2601640 A CA 2601640A CA 2601640 A CA2601640 A CA 2601640A CA 2601640 C CA2601640 C CA 2601640C
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- pharmaceutically acceptable
- disease
- acceptable salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000003120 macrolide antibiotic agent Substances 0.000 title description 15
- 206010061218 Inflammation Diseases 0.000 title description 7
- 230000004054 inflammatory process Effects 0.000 title description 7
- 230000000968 intestinal effect Effects 0.000 title description 7
- 229940041033 macrolides Drugs 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims abstract description 22
- 238000011282 treatment Methods 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 239000003814 drug Substances 0.000 claims abstract description 12
- 206010009944 Colon cancer Diseases 0.000 claims abstract description 7
- 208000029742 colonic neoplasm Diseases 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 230000002265 prevention Effects 0.000 claims abstract description 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 7
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 7
- 208000011231 Crohn disease Diseases 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 201000010099 disease Diseases 0.000 description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
- 206010009887 colitis Diseases 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 8
- OVOJUAKDTOOXRF-UHFFFAOYSA-N 2,4-dinitrobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O OVOJUAKDTOOXRF-UHFFFAOYSA-N 0.000 description 7
- 230000006378 damage Effects 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 230000003110 anti-inflammatory effect Effects 0.000 description 5
- 210000001072 colon Anatomy 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 210000004877 mucosa Anatomy 0.000 description 5
- 239000008194 pharmaceutical composition Substances 0.000 description 5
- 206010028980 Neoplasm Diseases 0.000 description 4
- 201000011510 cancer Diseases 0.000 description 4
- 230000000112 colonic effect Effects 0.000 description 4
- 229960003957 dexamethasone Drugs 0.000 description 4
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000003873 salicylate salts Chemical class 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- NHJVRSWLHSJWIN-UHFFFAOYSA-N 2,4,6-trinitrobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O NHJVRSWLHSJWIN-UHFFFAOYSA-N 0.000 description 2
- 206010012735 Diarrhoea Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 229920003091 Methocel™ Polymers 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- 229940124599 anti-inflammatory drug Drugs 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 239000003246 corticosteroid Substances 0.000 description 2
- 229960001334 corticosteroids Drugs 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 210000002429 large intestine Anatomy 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002483 medication Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- -1 pessaries Substances 0.000 description 2
- 238000011552 rat model Methods 0.000 description 2
- 210000000664 rectum Anatomy 0.000 description 2
- 210000000813 small intestine Anatomy 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 206010064147 Gastrointestinal inflammation Diseases 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010020565 Hyperaemia Diseases 0.000 description 1
- UETNIIAIRMUTSM-UHFFFAOYSA-N Jacareubin Natural products CC1(C)OC2=CC3Oc4c(O)c(O)ccc4C(=O)C3C(=C2C=C1)O UETNIIAIRMUTSM-UHFFFAOYSA-N 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- 108091006629 SLC13A2 Proteins 0.000 description 1
- 238000010161 Student-Newman-Keuls test Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 206010054094 Tumour necrosis Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000004931 aggregating effect Effects 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000001949 anaesthesia Methods 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 230000001142 anti-diarrhea Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940125714 antidiarrheal agent Drugs 0.000 description 1
- 239000003793 antidiarrheal agent Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001713 cholinergic effect Effects 0.000 description 1
- 230000006020 chronic inflammation Effects 0.000 description 1
- 208000037976 chronic inflammation Diseases 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000008951 colonic inflammation Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 238000002651 drug therapy Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 238000013401 experimental design Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 239000008141 laxative Substances 0.000 description 1
- 229940125722 laxative agent Drugs 0.000 description 1
- 150000002617 leukotrienes Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000007433 macroscopic evaluation Methods 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 1
- 229960004963 mesalazine Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000002474 noradrenergic effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- QQBDLJCYGRGAKP-FOCLMDBBSA-N olsalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=C(C(O)=CC=2)C(O)=O)=C1 QQBDLJCYGRGAKP-FOCLMDBBSA-N 0.000 description 1
- 229960004110 olsalazine Drugs 0.000 description 1
- 238000001543 one-way ANOVA Methods 0.000 description 1
- 229940126701 oral medication Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 229940124641 pain reliever Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229960004618 prednisone Drugs 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- NCEXYHBECQHGNR-QZQOTICOSA-N sulfasalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 0.000 description 1
- 229960001940 sulfasalazine Drugs 0.000 description 1
- NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 230000008673 vomiting Effects 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
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05102244 | 2005-03-21 | ||
| EP05102244.0 | 2005-03-21 | ||
| PCT/EP2006/060709 WO2006100195A1 (en) | 2005-03-21 | 2006-03-14 | Use of macrolides for treating intestinal inflammation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2601640A1 CA2601640A1 (en) | 2006-09-28 |
| CA2601640C true CA2601640C (en) | 2013-10-22 |
Family
ID=36649815
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2601640A Expired - Fee Related CA2601640C (en) | 2005-03-21 | 2006-03-14 | Use of macrolides for treating intestinal inflammation |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20080249034A1 (https=) |
| EP (1) | EP1868619A1 (https=) |
| JP (1) | JP2008533186A (https=) |
| CN (1) | CN101212980A (https=) |
| AU (1) | AU2006226381B2 (https=) |
| BR (1) | BRPI0614009A2 (https=) |
| CA (1) | CA2601640C (https=) |
| EA (1) | EA012309B1 (https=) |
| IT (1) | ITMI20060460A1 (https=) |
| MX (1) | MX2007011544A (https=) |
| WO (1) | WO2006100195A1 (https=) |
| ZA (1) | ZA200708423B (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2343748T3 (es) * | 2005-07-06 | 2010-08-09 | Zambon S.P.A. | Formas cristalinas de compuestos macrolidos dotados de una actividad antiinflamatoria. |
| WO2008065636A2 (en) * | 2006-12-01 | 2008-06-05 | University College York - National University Of Ireland, Cork | Treatment of disease by modulating cf5 protein |
| KR20240004268A (ko) * | 2021-02-26 | 2024-01-11 | 팬더릭스 인코포레이티드 | 안정화된 초유 조성물 |
| CN113209084A (zh) * | 2021-05-18 | 2021-08-06 | 南开大学 | 化合物cp0119在制备用于治疗炎性肠病的药物中的应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2089219C1 (ru) * | 1994-02-22 | 1997-09-10 | Александра Леонидовна Бурмистрова | Способ лечения неспецифического язвенного колита |
| US5712253A (en) * | 1996-06-18 | 1998-01-27 | Abbott Laboratories | Macrocyclic 13-membered ring derivatives of erythromycins A and B |
| US6551632B2 (en) * | 1997-04-01 | 2003-04-22 | Thomas Julius Borody | Methods and compositions for treating inflammatory bowel disease |
| IT1306205B1 (it) * | 1999-01-15 | 2001-05-30 | Zambon Spa | Macrolidi ad attivita' antiinfiammatoria. |
| HRP20010018A2 (en) * | 2001-01-09 | 2002-12-31 | Pliva D D | Novel anti-inflammatory compounds |
| ITMI20021726A1 (it) * | 2002-08-01 | 2004-02-02 | Zambon Spa | Macrolidi ad attivita' antiinfiammatoria. |
| ITMI20040124A1 (it) * | 2004-01-29 | 2004-04-29 | Zambon Spa | Macrolidi ad attivita' antiinfiammatoria |
-
2005
- 2005-03-14 US US11/908,550 patent/US20080249034A1/en not_active Abandoned
-
2006
- 2006-03-14 CA CA2601640A patent/CA2601640C/en not_active Expired - Fee Related
- 2006-03-14 CN CNA2006800126183A patent/CN101212980A/zh active Pending
- 2006-03-14 MX MX2007011544A patent/MX2007011544A/es not_active Application Discontinuation
- 2006-03-14 WO PCT/EP2006/060709 patent/WO2006100195A1/en not_active Ceased
- 2006-03-14 AU AU2006226381A patent/AU2006226381B2/en not_active Ceased
- 2006-03-14 BR BRPI0614009-2A patent/BRPI0614009A2/pt not_active IP Right Cessation
- 2006-03-14 EP EP06725052A patent/EP1868619A1/en not_active Withdrawn
- 2006-03-14 EA EA200702036A patent/EA012309B1/ru not_active IP Right Cessation
- 2006-03-14 JP JP2008502380A patent/JP2008533186A/ja active Pending
- 2006-03-15 IT IT000460A patent/ITMI20060460A1/it unknown
-
2007
- 2007-10-02 ZA ZA200708423A patent/ZA200708423B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EA200702036A1 (ru) | 2008-02-28 |
| AU2006226381A1 (en) | 2006-09-28 |
| CN101212980A (zh) | 2008-07-02 |
| ZA200708423B (en) | 2009-03-25 |
| CA2601640A1 (en) | 2006-09-28 |
| WO2006100195A1 (en) | 2006-09-28 |
| AU2006226381B2 (en) | 2011-09-08 |
| JP2008533186A (ja) | 2008-08-21 |
| ITMI20060460A1 (it) | 2006-09-22 |
| BRPI0614009A2 (pt) | 2011-03-01 |
| EP1868619A1 (en) | 2007-12-26 |
| MX2007011544A (es) | 2008-03-11 |
| US20080249034A1 (en) | 2008-10-09 |
| EA012309B1 (ru) | 2009-08-28 |
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