OA11713A - 13-Membered azalides and their use as antibiotic agents. - Google Patents
13-Membered azalides and their use as antibiotic agents. Download PDFInfo
- Publication number
- OA11713A OA11713A OA1200100120A OA1200100120A OA11713A OA 11713 A OA11713 A OA 11713A OA 1200100120 A OA1200100120 A OA 1200100120A OA 1200100120 A OA1200100120 A OA 1200100120A OA 11713 A OA11713 A OA 11713A
- Authority
- OA
- OAPI
- Prior art keywords
- alkyl
- alkenyl
- alkynyl
- hydrogen
- alkenyi
- Prior art date
Links
- 230000003115 biocidal effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 49
- 238000000034 method Methods 0.000 claims abstract 7
- 208000015181 infectious disease Diseases 0.000 claims abstract 6
- 125000000217 alkyl group Chemical group 0.000 claims 182
- 229910052739 hydrogen Inorganic materials 0.000 claims 127
- 239000001257 hydrogen Substances 0.000 claims 123
- 125000000304 alkynyl group Chemical group 0.000 claims 114
- 125000003342 alkenyl group Chemical group 0.000 claims 111
- 229910052799 carbon Inorganic materials 0.000 claims 108
- 150000002431 hydrogen Chemical class 0.000 claims 91
- -1 2-pyrimidyl Chemical group 0.000 claims 61
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 42
- 125000003118 aryl group Chemical group 0.000 claims 41
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 40
- 125000004093 cyano group Chemical group *C#N 0.000 claims 37
- 125000003545 alkoxy group Chemical group 0.000 claims 28
- 125000005843 halogen group Chemical group 0.000 claims 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 26
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 20
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims 19
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 17
- 125000001072 heteroaryl group Chemical group 0.000 claims 17
- 125000000623 heterocyclic group Chemical group 0.000 claims 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 15
- 125000001424 substituent group Chemical group 0.000 claims 15
- 229910052760 oxygen Inorganic materials 0.000 claims 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 14
- 125000004429 atom Chemical group 0.000 claims 10
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 7
- 125000004414 alkyl thio group Chemical group 0.000 claims 7
- 206010011416 Croup infectious Diseases 0.000 claims 6
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 230000015572 biosynthetic process Effects 0.000 claims 6
- 201000010549 croup Diseases 0.000 claims 6
- 239000001301 oxygen Substances 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 229920006395 saturated elastomer Polymers 0.000 claims 6
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 4
- 208000035143 Bacterial infection Diseases 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- 239000005864 Sulphur Substances 0.000 claims 4
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 4
- 208000022362 bacterial infectious disease Diseases 0.000 claims 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 241000251468 Actinopterygii Species 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 3
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims 3
- 238000010438 heat treatment Methods 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 229910014585 C2-Ce Inorganic materials 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- 239000003586 protic polar solvent Substances 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 claims 1
- MCNQUWLLXZZZAC-UHFFFAOYSA-N 4-cyano-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-n-piperidin-1-ylpyrazole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=C(C#N)C(C(=O)NN2CCCCC2)=NN1C1=CC=C(Cl)C=C1Cl MCNQUWLLXZZZAC-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 1
- 241000872931 Myoporum sandwicense Species 0.000 claims 1
- SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229960004592 isopropanol Drugs 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 150000004780 naphthols Chemical class 0.000 claims 1
- 229940099990 ogen Drugs 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 230000001580 bacterial effect Effects 0.000 abstract 2
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Biotechnology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Genetics & Genomics (AREA)
- Public Health (AREA)
- Biochemistry (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Pyridine Compounds (AREA)
- Pyrane Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicinal Preparation (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10939998P | 1998-11-20 | 1998-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA11713A true OA11713A (en) | 2005-01-25 |
Family
ID=22327457
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA1200100120A OA11713A (en) | 1998-11-20 | 1999-11-09 | 13-Membered azalides and their use as antibiotic agents. |
Country Status (46)
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HN1998000086A (es) | 1997-06-11 | 1999-03-08 | Pfizer Prod Inc | Derivados de 9 - desofo - 9 aza - 9a - homoeritromicina a - c - 4 sustituidos. |
| AP9801420A0 (en) * | 1998-01-02 | 1998-12-31 | Pfizer Prod Inc | Novel macrolides. |
| UA70972C2 (uk) * | 1998-11-20 | 2004-11-15 | Пфайзер Продактс Інк. | 13-членні азаліди і їх застосування як антибіотиків |
| OA11945A (en) * | 1999-05-24 | 2006-04-13 | Pfizer Prod Inc | 13-Methyl erythromycin derivatives. |
| US6465437B1 (en) * | 1999-06-30 | 2002-10-15 | Pfizer Inc. | Diphosphate salt of a 4″-substituted-9-deoxo-9A-AZA-9A- homoerythromycin derivative and its pharmaceutical composition |
| EA200200995A1 (ru) * | 2000-04-27 | 2003-04-24 | Пфайзер Продактс Инк. | Применение композиций азалидных антибиотиков для лечения или предупреждения бактериальных или протозойных инфекций у млекопитающих |
| RU2263117C2 (ru) * | 2001-04-27 | 2005-10-27 | Пфайзер Продактс Инк. | Способ получения 4"-замещенных производных 9-деоксо-9а-аза-9а-гомоэритромицина а |
| WO2003014136A1 (en) * | 2001-08-08 | 2003-02-20 | Taisho Pharmaceutical Co., Ltd. | 11a-AZALIDE COMPOUNDS AND PROCESS FOR PRODUCING THE SAME |
| CA2529817C (en) * | 2003-03-10 | 2013-02-12 | Optimer Pharmaceuticals, Inc. | Novel antibacterial agents |
| WO2004108744A2 (en) * | 2003-05-19 | 2004-12-16 | Prasad K Deshpande | Azalides and azaketolides having antimicrobial activity |
| CA2546195A1 (en) * | 2003-11-21 | 2005-06-02 | Pfizer Products Inc. | The use of anti biotics as vaccine adjuvants |
| WO2007091393A1 (ja) * | 2006-02-07 | 2007-08-16 | Taisho Pharmaceutical Co., Ltd. | １０ａ－アザライド化合物 |
| JPWO2009019868A1 (ja) * | 2007-08-06 | 2010-10-28 | 大正製薬株式会社 | １０ａ、１２位架橋型１０ａ−アザライド化合物 |
| JPWO2009139181A1 (ja) | 2008-05-15 | 2011-09-15 | 大正製薬株式会社 | ４員環構造を有する１０ａ−アザライド化合物 |
| JP5908479B2 (ja) * | 2010-09-20 | 2016-04-26 | ノバルティス ティーアゲズントハイト アーゲー | クラジノース環のＣ−４”をエポキシド基で修飾した９−デオキソ−９ａ−アザ−９ａ−ホモエリスロマイシンＡの新規製造方法 |
| CN102295672B (zh) * | 2011-07-13 | 2014-06-04 | 武汉回盛生物科技有限公司 | 一种泰拉菌素的合成方法 |
| WO2013013834A1 (en) | 2011-07-27 | 2013-01-31 | Farma Grs, D.O.O. | New crystalline forms of tulathromycin |
| CN102786569B (zh) * | 2012-09-07 | 2016-12-07 | 安徽中升药业有限公司 | 泰拉霉素中间体及其制备方法与泰拉霉素的制备方法 |
| EP3027634B1 (en) * | 2013-07-31 | 2018-03-21 | Farma GRS, d.o.o. | Process for preparation of tulathromycin |
| CN105085590A (zh) * | 2014-05-16 | 2015-11-25 | 普莱柯生物工程股份有限公司 | 一种大环内酯类化合物 |
| CN104725446B (zh) * | 2015-03-26 | 2017-10-27 | 宁夏泰瑞制药股份有限公司 | 一种从泰拉霉素粗品中分离泰拉霉素a和泰拉霉素b的方法 |
| AU2019385333B2 (en) * | 2018-11-19 | 2025-04-17 | President And Fellows Of Harvard College | C10-alkylene substituted 13-membered macrolides and uses thereof |
| KR20210123288A (ko) * | 2018-11-19 | 2021-10-13 | 지카니 테라퓨틱스, 인크. | C11-환식 치환된 13-원 마크롤라이드 및 이의 용도 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI7910768A8 (en) | 1979-04-02 | 1996-06-30 | Pliva Pharm & Chem Works | Process for pripering 11-aza-4-0-cladinosyl-6-0-desosaminyl-15-ethyl- 7,13,14-trihydroxy-3,5,7,9,12,14-hexamethyl- oxacyclopentadecane-2-one and their derivatives |
| SI8110592A8 (en) * | 1981-03-06 | 1996-06-30 | Pliva Pharm & Chem Works | Process for preparing of n-methyl-11-aza-10-deoxo-10-dihydroerythromycine a and derivatives thereof |
| US4474768A (en) * | 1982-07-19 | 1984-10-02 | Pfizer Inc. | N-Methyl 11-aza-10-deoxo-10-dihydro-erytromycin A, intermediates therefor |
| YU44599B (en) * | 1986-09-12 | 1990-10-31 | Pliva Pharm & Chem Works | Process for preparing complex of n-methyl-11-aza-10-deoxo-10-dihydroeritromicine a and 11-aza-10-deoxo-10-dihydroeritromicine a with metals |
| US5106961A (en) | 1987-05-26 | 1992-04-21 | Eli Lilly And Company | Erythromycin ring-contracted derivatives |
| SI9011409A (en) | 1990-07-18 | 1995-10-31 | Pliva Pharm & Chem Works | O-methyl azitromycin derivates, methods and intermediates for their preparation and methods for preparation of pharmaceuticals products which comprise them |
| HRP931480B1 (en) * | 1993-12-08 | 1997-08-31 | Sour Pliva | 9a-N-(N'-CARBAMONYL) and 9a-N-(N'-THIOCARBAMONYL) DERIVATES OF 9-DEOXO-9a-HOMOERYTHROMYCIN A |
| GB2327084A (en) * | 1997-07-08 | 1999-01-13 | Merck & Co Inc | 9a-Aza-3-ketolide antibiotics |
| UA70972C2 (uk) * | 1998-11-20 | 2004-11-15 | Пфайзер Продактс Інк. | 13-членні азаліди і їх застосування як антибіотиків |
-
1999
- 1999-09-11 UA UA2001053376A patent/UA70972C2/uk unknown
- 1999-11-09 AP APAP/P/2001/002142A patent/AP2001002142A0/en unknown
- 1999-11-09 EP EP99954277A patent/EP1131331B1/en not_active Expired - Lifetime
- 1999-11-09 SI SI9930572T patent/SI1131331T1/xx unknown
- 1999-11-09 NO NO20012464A patent/NO319796B1/no not_active IP Right Cessation
- 1999-11-09 KR KR10-2001-7006301A patent/KR100477774B1/ko not_active Expired - Lifetime
- 1999-11-09 CZ CZ20011754A patent/CZ303099B6/cs not_active IP Right Cessation
- 1999-11-09 RS YUP-334/01A patent/RS50302B/sr unknown
- 1999-11-09 AU AU10686/00A patent/AU766106B2/en not_active Expired
- 1999-11-09 HR HR20010374A patent/HRP20010374B1/xx not_active IP Right Cessation
- 1999-11-09 CA CA002351429A patent/CA2351429C/en not_active Expired - Lifetime
- 1999-11-09 AT AT99954277T patent/ATE260927T1/de active
- 1999-11-09 ME MEP-2008-719A patent/ME00467B/me unknown
- 1999-11-09 DK DK99954277T patent/DK1131331T3/da active
- 1999-11-09 SK SK663-2001A patent/SK284607B6/sk not_active IP Right Cessation
- 1999-11-09 ES ES99954277T patent/ES2216581T3/es not_active Expired - Lifetime
- 1999-11-09 WO PCT/IB1999/001803 patent/WO2000031097A1/en not_active Ceased
- 1999-11-09 BR BRPI9915480A patent/BRPI9915480B1/pt not_active IP Right Cessation
- 1999-11-09 EA EA200100416A patent/EA005156B1/ru not_active IP Right Cessation
- 1999-11-09 ID IDW00200101093A patent/ID28548A/id unknown
- 1999-11-09 PT PT99954277T patent/PT1131331E/pt unknown
- 1999-11-09 HK HK02102807.7A patent/HK1041269A1/zh unknown
- 1999-11-09 EA EA200400701A patent/EA009729B1/ru not_active IP Right Cessation
- 1999-11-09 DE DE1999615336 patent/DE69915336T2/de not_active Expired - Lifetime
- 1999-11-09 PL PL347784A patent/PL198580B1/pl unknown
- 1999-11-09 IL IL14263199A patent/IL142631A0/xx unknown
- 1999-11-09 JP JP2000583925A patent/JP3842973B2/ja not_active Expired - Lifetime
- 1999-11-09 CN CN99813464A patent/CN1326460A/zh active Pending
- 1999-11-09 OA OA1200100120A patent/OA11713A/en unknown
- 1999-11-09 CN CNA2008100813586A patent/CN101367853A/zh active Pending
- 1999-11-09 BR BRPI9915480A patent/BRPI9915480B8/pt not_active IP Right Cessation
- 1999-11-09 NZ NZ511199A patent/NZ511199A/en not_active IP Right Cessation
- 1999-11-09 HU HU0104313A patent/HU229008B1/hu active Protection Beyond IP Right Term
- 1999-11-15 TW TW088119885A patent/TWI243824B/zh not_active IP Right Cessation
- 1999-11-15 TW TW092131563A patent/TWI243825B/zh not_active IP Right Cessation
- 1999-11-17 DZ DZ990244A patent/DZ2944A1/xx active
- 1999-11-17 EG EG147699A patent/EG23823A/xx active
- 1999-11-17 MA MA25850A patent/MA26707A1/fr unknown
- 1999-11-17 UY UY25805A patent/UY25805A1/es not_active Application Discontinuation
- 1999-11-17 TN TNTNSN99214A patent/TNSN99214A1/fr unknown
- 1999-11-17 PA PA19998485601A patent/PA8485601A1/es unknown
- 1999-11-18 US US09/442,530 patent/US6329345B1/en not_active Expired - Lifetime
- 1999-11-18 CO CO99072704A patent/CO5380019A1/es active IP Right Grant
- 1999-11-18 AR ARP990105876A patent/AR019496A1/es active IP Right Grant
- 1999-11-18 GT GT199900198A patent/GT199900198A/es unknown
- 1999-11-18 MY MYPI99005021A patent/MY122353A/en unknown
- 1999-11-18 PE PE1999001166A patent/PE20001378A1/es not_active Application Discontinuation
-
2001
- 2001-04-16 IL IL142631A patent/IL142631A/en not_active IP Right Cessation
- 2001-04-17 IS IS5918A patent/IS2350B/is unknown
- 2001-05-17 ZA ZA200104019A patent/ZA200104019B/en unknown
- 2001-06-14 BG BG105600A patent/BG65107B1/bg unknown
-
2005
- 2005-02-18 NO NO20050904A patent/NO329629B1/no not_active IP Right Cessation
- 2005-02-18 NO NO20050893A patent/NO330249B1/no not_active IP Right Cessation
-
2007
- 2007-02-15 AR ARP070100663A patent/AR059524A2/es active IP Right Grant
- 2007-02-15 AR ARP070100662A patent/AR059523A2/es active IP Right Grant
-
2008
- 2008-02-11 IL IL189430A patent/IL189430A/en not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| OA11713A (en) | 13-Membered azalides and their use as antibiotic agents. | |
| KR100396168B1 (ko) | 4″-치환된-9-데옥소-9ａ-아자-9ａ-호모에리트로마이신 Ａ유도체 | |
| KR101566053B1 (ko) | 항균 활성을 갖는 케톨라이드 | |
| OA11753A (en) | Ketolide antibiotics. | |
| CA2293335A1 (en) | 9-oxime erythromycin derivatives | |
| US6162794A (en) | Erythromycin derivatives | |
| US6248719B1 (en) | Tricyclic 3-keto derivatives of 6-O-methylerthromycin | |
| US20020151507A1 (en) | 9-oxime erythromycin derivatives | |
| EP0952157B1 (en) | 9A, 11B-Dehydro derivatives of 9-oxime-3-keto-6-0-methylerythromycin | |
| NZ526120A (en) | 13-membered azalides and their use as antibiotic agents | |
| MXPA01005055A (en) | 13-membered azalides and their use as antibiotic agents |