RU2243230C2 - Макролиды и фармацевтический состав на их основе - Google Patents
Макролиды и фармацевтический состав на их основеInfo
- Publication number
- RU2243230C2 RU2243230C2 RU2001118831/04A RU2001118831A RU2243230C2 RU 2243230 C2 RU2243230 C2 RU 2243230C2 RU 2001118831/04 A RU2001118831/04 A RU 2001118831/04A RU 2001118831 A RU2001118831 A RU 2001118831A RU 2243230 C2 RU2243230 C2 RU 2243230C2
- Authority
- RU
- Russia
- Prior art keywords
- formula
- oxime
- dehydroerythromycin
- compound
- compounds
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 4
- 239000003120 macrolide antibiotic agent Substances 0.000 title abstract description 17
- 229940041033 macrolides Drugs 0.000 title abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 70
- 150000002923 oximes Chemical class 0.000 claims abstract description 27
- 230000003110 anti-inflammatory effect Effects 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 229920006395 saturated elastomer Chemical group 0.000 claims abstract description 5
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 7
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- 239000002260 anti-inflammatory agent Substances 0.000 abstract description 6
- 239000003242 anti bacterial agent Substances 0.000 abstract description 4
- 229940088710 antibiotic agent Drugs 0.000 abstract description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000007721 medicinal effect Effects 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
- -1 hydrochloric Chemical class 0.000 description 27
- 229960003276 erythromycin Drugs 0.000 description 24
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 23
- 239000000243 solution Substances 0.000 description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
- 229930006677 Erythromycin A Natural products 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 13
- 210000004027 cell Anatomy 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
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- 241000700159 Rattus Species 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
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- ZGTFNNUASMWGTM-UHFFFAOYSA-N 1,3-thiazole-2-carbaldehyde Chemical compound O=CC1=NC=CS1 ZGTFNNUASMWGTM-UHFFFAOYSA-N 0.000 description 3
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- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 2
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- KNJDBYZZKAZQNG-UHFFFAOYSA-N lucigenin Chemical compound [O-][N+]([O-])=O.[O-][N+]([O-])=O.C12=CC=CC=C2[N+](C)=C(C=CC=C2)C2=C1C1=C(C=CC=C2)C2=[N+](C)C2=CC=CC=C12 KNJDBYZZKAZQNG-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI99A000061 | 1999-01-15 | ||
| IT1999MI000061A IT1306205B1 (it) | 1999-01-15 | 1999-01-15 | Macrolidi ad attivita' antiinfiammatoria. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2001118831A RU2001118831A (ru) | 2003-06-10 |
| RU2243230C2 true RU2243230C2 (ru) | 2004-12-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2001118831/04A RU2243230C2 (ru) | 1999-01-15 | 2000-01-12 | Макролиды и фармацевтический состав на их основе |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6455576B1 (https=) |
| EP (1) | EP1144427B1 (https=) |
| JP (1) | JP4568433B2 (https=) |
| CN (1) | CN1151165C (https=) |
| AT (1) | ATE308552T1 (https=) |
| AU (1) | AU769006B2 (https=) |
| BR (1) | BR0007514A (https=) |
| CA (1) | CA2368400C (https=) |
| DE (1) | DE60023647T2 (https=) |
| ES (1) | ES2251966T3 (https=) |
| HU (1) | HU229228B1 (https=) |
| IL (2) | IL144044A0 (https=) |
| IT (1) | IT1306205B1 (https=) |
| MX (1) | MXPA01007164A (https=) |
| NO (1) | NO318982B1 (https=) |
| RU (1) | RU2243230C2 (https=) |
| SK (1) | SK286772B6 (https=) |
| WO (1) | WO2000042055A2 (https=) |
| ZA (1) | ZA200105748B (https=) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA014711B1 (ru) * | 2005-05-24 | 2011-02-28 | Пфайзер Инк. | Мотилидные соединения, содержащая их фармацевтическая композиция, их применение, способ лечения заболевания со сниженной моторикой желудочно-кишечного тракта и способ индукции сокращения ткани |
| RU2455309C2 (ru) * | 2010-07-20 | 2012-07-10 | Открытое Акционерное Общество "Татхимфармпрепараты" | Способ получения аморфной формы рокситромицина |
| RU2811591C1 (ru) * | 2020-03-12 | 2024-01-15 | ЗОЕТИС СЕРВИСИЗ ЭлЭлСи | Иммуномодулирующие азалиды на основе мочевины |
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| HRP20010018A2 (en) | 2001-01-09 | 2002-12-31 | Pliva D D | Novel anti-inflammatory compounds |
| AU2003264917A1 (en) | 2002-07-08 | 2004-01-23 | Pliva - Istrazivacki Institut D.O.O. | Hybrid molecules of macrolides with steroid/non-steroid anti-inflammatory, antineoplastic and antiviral active molecules |
| RS20050008A (sr) | 2002-07-08 | 2007-06-04 | Pliva-Istraživački Institut D.O.O., | Nova jedinjenja,kompozicije i metode za lečenje inflamatornih oboljenja i stanja |
| EP1521763A2 (en) * | 2002-07-08 | 2005-04-13 | Pliva - Istrazivacki Institut d.o.o. | Novel nonsteroidal anti-inflammatory substances, compositions and methods for their use |
| ITMI20021726A1 (it) | 2002-08-01 | 2004-02-02 | Zambon Spa | Macrolidi ad attivita' antiinfiammatoria. |
| TW200420573A (en) | 2002-09-26 | 2004-10-16 | Rib X Pharmaceuticals Inc | Bifunctional heterocyclic compounds and methods of making and using same |
| ITMI20022292A1 (it) * | 2002-10-29 | 2004-04-30 | Zambon Spa | 9a-azalidi ad attivita' antiinfiammatoria. |
| BRPI0410638A (pt) * | 2003-04-17 | 2006-06-13 | Sandoz Ag | derivados de azitromicina |
| HRP20030324A2 (en) | 2003-04-24 | 2005-02-28 | Pliva-Istra�iva�ki institut d.o.o. | Compounds of antiinflammatory effect |
| ITMI20040124A1 (it) * | 2004-01-29 | 2004-04-29 | Zambon Spa | Macrolidi ad attivita' antiinfiammatoria |
| WO2006130128A2 (en) * | 2004-02-18 | 2006-12-07 | Chiron Corporation | Methods of identifying anti-inflammatory macrolides |
| EP1723159B1 (en) | 2004-02-27 | 2019-06-12 | Melinta Therapeutics, Inc. | Macrocyclic compounds and methods of making and using the same |
| WO2006035301A2 (en) * | 2004-09-27 | 2006-04-06 | Ranbaxy Laboratories Limited | Erythromycin a derivatives as antibacterial agents |
| ES2337915T3 (es) | 2004-10-27 | 2010-04-30 | Glaxosmithkline Istrazivacki Centar Zagreb D.O.O. | Conjugados con adtividad antiinflamatoria. |
| US20080249034A1 (en) * | 2005-03-21 | 2008-10-09 | Zambon S.P.A. | Use of Macrolides for Treating Intestinal Inflammation |
| US20110178287A1 (en) | 2010-01-19 | 2011-07-21 | Cerulean Pharma Inc. | Cyclodextrin-based polymers for therapeutic delivery |
| GB201608236D0 (en) | 2016-05-11 | 2016-06-22 | Fidelta D O O | Seco macrolide compounds |
| TWI830987B (zh) | 2020-03-12 | 2024-02-01 | 美商碩騰服務公司 | 免疫調節脲氮雜內酯 |
| WO2021195126A1 (en) | 2020-03-24 | 2021-09-30 | Burnet Michael W | Anti-infective and anti-viral compounds and compositions |
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| RU2114859C1 (ru) * | 1992-11-05 | 1998-07-10 | Руссель Юклаф | Производные эритромицина, фармацевтическая композиция, способ получения производных эритромицина |
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| IT1189285B (it) * | 1982-05-28 | 1988-02-04 | Nuovo Consor Sanitar Nazionale | Sali dell'antibiotico eritromicina e del suo estere propionico con acidi ad attivita' terapeutica coadiuvante |
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| KR19980701895A (ko) * | 1995-03-08 | 1998-06-25 | 이라우치지마 가즈다카 | 면역관련병 처치제 및 그의 탐색 방법 |
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- 2000-01-12 AT AT00904899T patent/ATE308552T1/de not_active IP Right Cessation
- 2000-01-12 EP EP00904899A patent/EP1144427B1/en not_active Expired - Lifetime
- 2000-01-12 HU HU0105105A patent/HU229228B1/hu not_active IP Right Cessation
- 2000-01-12 AU AU26636/00A patent/AU769006B2/en not_active Ceased
- 2000-01-12 CN CNB008027676A patent/CN1151165C/zh not_active Expired - Fee Related
- 2000-01-12 JP JP2000593622A patent/JP4568433B2/ja not_active Expired - Fee Related
- 2000-01-12 CA CA002368400A patent/CA2368400C/en not_active Expired - Fee Related
- 2000-01-12 ES ES00904899T patent/ES2251966T3/es not_active Expired - Lifetime
- 2000-01-12 DE DE60023647T patent/DE60023647T2/de not_active Expired - Lifetime
- 2000-01-12 MX MXPA01007164A patent/MXPA01007164A/es unknown
- 2000-01-12 BR BR0007514-0A patent/BR0007514A/pt not_active IP Right Cessation
- 2000-01-12 SK SK981-2001A patent/SK286772B6/sk not_active IP Right Cessation
- 2000-01-12 IL IL14404400A patent/IL144044A0/xx active IP Right Grant
- 2000-01-12 RU RU2001118831/04A patent/RU2243230C2/ru not_active IP Right Cessation
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- 2001-06-28 IL IL144044A patent/IL144044A/en not_active IP Right Cessation
- 2001-07-12 ZA ZA200105748A patent/ZA200105748B/en unknown
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA014711B1 (ru) * | 2005-05-24 | 2011-02-28 | Пфайзер Инк. | Мотилидные соединения, содержащая их фармацевтическая композиция, их применение, способ лечения заболевания со сниженной моторикой желудочно-кишечного тракта и способ индукции сокращения ткани |
| RU2455309C2 (ru) * | 2010-07-20 | 2012-07-10 | Открытое Акционерное Общество "Татхимфармпрепараты" | Способ получения аморфной формы рокситромицина |
| RU2811591C1 (ru) * | 2020-03-12 | 2024-01-15 | ЗОЕТИС СЕРВИСИЗ ЭлЭлСи | Иммуномодулирующие азалиды на основе мочевины |
| RU2811591C9 (ru) * | 2020-03-12 | 2024-03-26 | ЗОЕТИС СЕРВИСИЗ ЭлЭлСи | Иммуномодулирующие азалиды на основе мочевины |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1151165C (zh) | 2004-05-26 |
| AU2663600A (en) | 2000-08-01 |
| ATE308552T1 (de) | 2005-11-15 |
| DE60023647T2 (de) | 2006-08-10 |
| ES2251966T3 (es) | 2006-05-16 |
| NO20013517D0 (no) | 2001-07-16 |
| JP4568433B2 (ja) | 2010-10-27 |
| HUP0105105A2 (hu) | 2002-04-29 |
| EP1144427B1 (en) | 2005-11-02 |
| CA2368400A1 (en) | 2000-07-20 |
| BR0007514A (pt) | 2001-11-20 |
| IL144044A (en) | 2006-12-31 |
| MXPA01007164A (es) | 2002-03-27 |
| IL144044A0 (en) | 2002-04-21 |
| IT1306205B1 (it) | 2001-05-30 |
| SK286772B6 (sk) | 2009-05-07 |
| HU229228B1 (en) | 2013-09-30 |
| ZA200105748B (en) | 2002-10-14 |
| EP1144427A2 (en) | 2001-10-17 |
| HUP0105105A3 (en) | 2003-05-28 |
| JP2002534531A (ja) | 2002-10-15 |
| DE60023647D1 (de) | 2005-12-08 |
| US6455576B1 (en) | 2002-09-24 |
| CN1336932A (zh) | 2002-02-20 |
| ITMI990061A1 (it) | 2000-07-15 |
| SK9812001A3 (en) | 2002-01-07 |
| WO2000042055A2 (en) | 2000-07-20 |
| EP1144427A3 (en) | 2002-08-28 |
| WO2000042055A3 (en) | 2001-09-07 |
| NO20013517L (no) | 2001-07-16 |
| NO318982B1 (no) | 2005-05-30 |
| AU769006B2 (en) | 2004-01-15 |
| CA2368400C (en) | 2007-06-05 |
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