UA71962C2 - Halo derivatives of 9-deoxo-9a-aza-9a-homoerythromycin a, a method for the preparation thereof and a pharmaceutical composition - Google Patents
Halo derivatives of 9-deoxo-9a-aza-9a-homoerythromycin a, a method for the preparation thereof and a pharmaceutical composition Download PDFInfo
- Publication number
- UA71962C2 UA71962C2 UA2001118221A UA2001118221A UA71962C2 UA 71962 C2 UA71962 C2 UA 71962C2 UA 2001118221 A UA2001118221 A UA 2001118221A UA 2001118221 A UA2001118221 A UA 2001118221A UA 71962 C2 UA71962 C2 UA 71962C2
- Authority
- UA
- Ukraine
- Prior art keywords
- oxygen
- same
- sulfur
- compound according
- halo
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 125000001475 halogen functional group Chemical group 0.000 title abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 26
- 239000001301 oxygen Substances 0.000 claims abstract description 26
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 21
- 239000011593 sulfur Substances 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 12
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- 235000005985 organic acids Nutrition 0.000 claims abstract description 8
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- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 5
- 230000002265 prevention Effects 0.000 claims abstract description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 4
- 238000011282 treatment Methods 0.000 claims abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 41
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- 239000000654 additive Substances 0.000 claims description 7
- 230000000996 additive effect Effects 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
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- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 16
- 125000005843 halogen group Chemical group 0.000 claims 11
- 239000000460 chlorine Substances 0.000 claims 9
- 229910052801 chlorine Inorganic materials 0.000 claims 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
- 229910052794 bromium Inorganic materials 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 239000011737 fluorine Substances 0.000 claims 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 abstract 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 1
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- 238000005481 NMR spectroscopy Methods 0.000 description 8
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 7
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- XQACWEBGSZBLRG-UHFFFAOYSA-N 1-bromo-4-isothiocyanatobenzene Chemical compound BrC1=CC=C(N=C=S)C=C1 XQACWEBGSZBLRG-UHFFFAOYSA-N 0.000 description 1
- JINSQUCXLLEHSU-UHFFFAOYSA-N 1-chloro-2-(fluoromethyl)-4-isocyanatobenzene Chemical compound FCC1=CC(N=C=O)=CC=C1Cl JINSQUCXLLEHSU-UHFFFAOYSA-N 0.000 description 1
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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
- A61K31/7048—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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Communicable Diseases (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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HR990130A HRP990130B1 (en) | 1999-05-03 | 1999-05-03 | HALOGEN DERIVATIVES 9a-N-(N'-ARYLCARBAMOYL)- AND 9a-N-(N'-ARYLTHIOCARBAMOYL)-9-DEOXO-9a-AZA-9a OF HOMOERYTHROMYCIN A |
| PCT/HR2000/000013 WO2000066603A1 (en) | 1999-05-03 | 2000-05-02 | Halo derivatives of 9-deoxo-9a-aza-9a-homerythromycin a |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA71962C2 true UA71962C2 (en) | 2005-01-17 |
Family
ID=10946916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2001118221A UA71962C2 (en) | 1999-05-03 | 2000-02-05 | Halo derivatives of 9-deoxo-9a-aza-9a-homoerythromycin a, a method for the preparation thereof and a pharmaceutical composition |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US6872707B1 (is) |
| EP (1) | EP1175429B1 (is) |
| JP (1) | JP2002543213A (is) |
| KR (1) | KR100714740B1 (is) |
| CN (1) | CN1140535C (is) |
| AT (1) | ATE244258T1 (is) |
| AU (1) | AU767681B2 (is) |
| BG (1) | BG106173A (is) |
| BR (1) | BR0010231A (is) |
| CA (1) | CA2372977A1 (is) |
| CZ (1) | CZ20013913A3 (is) |
| DE (1) | DE60003671T2 (is) |
| DK (1) | DK1175429T3 (is) |
| EA (1) | EA005214B1 (is) |
| EE (1) | EE05007B1 (is) |
| ES (1) | ES2202107T3 (is) |
| GE (1) | GEP20032928B (is) |
| HK (1) | HK1045522B (is) |
| HR (1) | HRP990130B1 (is) |
| HU (1) | HUP0201146A3 (is) |
| IL (2) | IL145986A0 (is) |
| IS (1) | IS6115A (is) |
| MX (1) | MXPA01011038A (is) |
| NO (1) | NO320138B1 (is) |
| NZ (1) | NZ515278A (is) |
| PL (1) | PL351402A1 (is) |
| PT (1) | PT1175429E (is) |
| SI (1) | SI1175429T1 (is) |
| SK (1) | SK284513B6 (is) |
| TR (1) | TR200103143T2 (is) |
| UA (1) | UA71962C2 (is) |
| WO (1) | WO2000066603A1 (is) |
| ZA (1) | ZA200108484B (is) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP20010146B1 (en) * | 2001-02-28 | 2005-10-31 | Pliva D.D. | 9a-N-(N'-(PHENYLSULFONYL)CARBAMOYL) DERIVATIVES OF 9-DEOXO-9-DIHYDRO-9a-AZA-9a-HOMOERYTHROMYCIN A AND OF 5-O-DESOSAMINYL-9-DEOXO-9-DIHYDRO-9a-AZA-9a-HOMOERYTHRONOLIDE A |
| HRP20020886A2 (en) * | 2002-11-11 | 2005-06-30 | PLIVA-ISTRAŽIVAČKI INSTITUT d.o.o. | SUBSTITUTED 9a-N-[N'-(BENZENSULFONYL)CARBAMOYL-γ-AMINOPROPYL) AND 9a-N(N' -(?-CYANOETHIL)-N' -(b |
| HRP20020885B1 (en) * | 2002-11-11 | 2007-05-31 | GlaxoSmithKline istra�iva�ki centar Zagreb d.o.o. | SUBSTITUTED 9a-N-{N'-[4-(SULFONYL)PHENYLCARBAMOYL]}DERIVATIVES 9-DEOXO-9-DIHYDRO-9a-AZA-9a-HOMOERITHROMYCIN A AND 5-O-DESOZAMINYL-9-DEOXO-9-DIHYDRO-9a-AZA-9a-HOMOERITHRONOLIDE A |
| HRP20020991A2 (en) * | 2002-12-12 | 2005-02-28 | Pliva-Istra�iva�ki institut d.o.o. | N"-Substituted 9a-N-(N'-carbamoyl-Gamma-aminopropyl), 9a-N-(N'? -thiocarbamoyl-Gamma-aminopropyl), 9a-N-(N'-((Beta-cyanoethyl)-N'-carbamoyl-Gamma? -aminopropyl) and 9a-N-(N'-(Beta-cyanoethyl)-N'-thiocarbamoyl-Gamma? -aminopropyl) derivatives of 9-de |
| HRP20030381B1 (en) * | 2003-05-14 | 2007-05-31 | GlaxoSmithKline istra�iva�ki centar Zagreb d.o.o. | 3-DECLADINOZYL 9a-N-CARBAMOYL AND 9a-N-THIOCARBAMOYL DERIVATIVES 9-DEOXO-9-DIHYDRO-9a-AZA-9a-HOMOERYTHROMICYNE A |
| EP1841437B1 (en) * | 2005-01-14 | 2009-04-29 | GlaxoSmithKline istrazivacki centar Zagreb d.o.o. | 9a-carbamoyl and thiocarbamoyl azalides with antimalarial activity |
| CA2699733C (en) * | 2007-09-17 | 2013-01-22 | Enanta Pharmaceuticals, Inc. | 6,11-bridged biaryl macrolides |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU43116B (en) * | 1979-04-02 | 1989-04-30 | Pliva Pharm & Chem Works | Process for preparing 11-aza-4-o-cladinosyl-6-o-desosaminyl-15-ethyl-7,13,14-trihydroxy-3,5,7,9,12,14-hexamethyl-oxacyclopentadecane-2-one(11-aza-10-deox |
| WO1992006991A1 (fr) * | 1990-10-15 | 1992-04-30 | Taisho Pharmaceutical Co., Ltd. | Erythromycine modifiee en 2' ou derive de cette substance |
| 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 |
-
1999
- 1999-05-03 HR HR990130A patent/HRP990130B1/xx not_active IP Right Cessation
-
2000
- 2000-02-05 UA UA2001118221A patent/UA71962C2/uk unknown
- 2000-05-02 DE DE60003671T patent/DE60003671T2/de not_active Expired - Fee Related
- 2000-05-02 EA EA200101170A patent/EA005214B1/ru not_active IP Right Cessation
- 2000-05-02 PL PL00351402A patent/PL351402A1/xx unknown
- 2000-05-02 IL IL14598600A patent/IL145986A0/xx active IP Right Grant
- 2000-05-02 KR KR1020017014046A patent/KR100714740B1/ko not_active IP Right Cessation
- 2000-05-02 PT PT00920940T patent/PT1175429E/pt unknown
- 2000-05-02 CZ CZ20013913A patent/CZ20013913A3/cs unknown
- 2000-05-02 US US09/959,662 patent/US6872707B1/en not_active Expired - Fee Related
- 2000-05-02 AU AU41350/00A patent/AU767681B2/en not_active Ceased
- 2000-05-02 MX MXPA01011038A patent/MXPA01011038A/es active IP Right Grant
- 2000-05-02 SI SI200030188T patent/SI1175429T1/xx unknown
- 2000-05-02 TR TR2001/03143T patent/TR200103143T2/xx unknown
- 2000-05-02 SK SK1570-2001A patent/SK284513B6/sk not_active IP Right Cessation
- 2000-05-02 EP EP00920940A patent/EP1175429B1/en not_active Expired - Lifetime
- 2000-05-02 CN CNB008071500A patent/CN1140535C/zh not_active Expired - Fee Related
- 2000-05-02 CA CA002372977A patent/CA2372977A1/en not_active Abandoned
- 2000-05-02 BR BR0010231-8A patent/BR0010231A/pt not_active IP Right Cessation
- 2000-05-02 NZ NZ515278A patent/NZ515278A/xx unknown
- 2000-05-02 HU HU0201146A patent/HUP0201146A3/hu unknown
- 2000-05-02 JP JP2000615632A patent/JP2002543213A/ja active Pending
- 2000-05-02 DK DK00920940T patent/DK1175429T3/da active
- 2000-05-02 EE EEP200100582A patent/EE05007B1/xx not_active IP Right Cessation
- 2000-05-02 AT AT00920940T patent/ATE244258T1/de not_active IP Right Cessation
- 2000-05-02 WO PCT/HR2000/000013 patent/WO2000066603A1/en active IP Right Grant
- 2000-05-02 GE GEAP20006227A patent/GEP20032928B/en unknown
- 2000-05-02 ES ES00920940T patent/ES2202107T3/es not_active Expired - Lifetime
-
2001
- 2001-10-16 ZA ZA200108484A patent/ZA200108484B/xx unknown
- 2001-10-17 IL IL145986A patent/IL145986A/en unknown
- 2001-10-19 IS IS6115A patent/IS6115A/is unknown
- 2001-11-01 NO NO20015346A patent/NO320138B1/no unknown
- 2001-12-03 BG BG106173A patent/BG106173A/bg unknown
-
2002
- 2002-09-26 HK HK02107027.0A patent/HK1045522B/zh not_active IP Right Cessation
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