CS274462B2 - Method of 10-dihydro-10-dexy-11-azarythronolides prepararation - Google Patents

Method of 10-dihydro-10-dexy-11-azarythronolides prepararation Download PDF

Info

Publication number: CS274462B2
Authority: CS; Czechoslovakia
Prior art keywords: dihydro; deoxo; azaerythronolide; optionally; alkyl
Prior art date: 1987-09-03

Application number

CS253388A

Other languages

Czech (cs)

English (en)

Other versions

CS253388A2 (en

Inventor

Slobodan Djokic

Nevenka Lopotar

Gabrijela Kobrehel

Hrvoje Krnjevic

Olga Carevic

Original Assignee

Pliva Pharm & Chem Works

Priority date (The priority date 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 date listed.)

1987-09-03

Filing date

1988-04-13

Publication date

1991-04-11

1987-09-03 Priority claimed from YU163187A external-priority patent/YU44641B/xx

1988-01-18 Priority claimed from YU85/88A external-priority patent/YU45054B/xx

1988-04-13 Application filed by Pliva Pharm & Chem Works filed Critical Pliva Pharm & Chem Works

1989-03-23 Priority to CS181689A priority Critical patent/CS274497B2/cs

1990-09-12 Publication of CS253388A2 publication Critical patent/CS253388A2/cs

1991-04-11 Publication of CS274462B2 publication Critical patent/CS274462B2/cs

Links

238000000034 method Methods 0.000 title claims abstract description 20
150000001875 compounds Chemical class 0.000 claims abstract description 17
150000003839 salts Chemical class 0.000 claims abstract description 16
239000002253 acid Substances 0.000 claims abstract description 14
238000002360 preparation method Methods 0.000 claims abstract description 8
230000007062 hydrolysis Effects 0.000 claims description 10
238000006460 hydrolysis reaction Methods 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 3
-1 aliphatic acid anhydride Chemical class 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims 2
150000008064 anhydrides Chemical class 0.000 claims 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 4
229940121363 anti-inflammatory agent Drugs 0.000 abstract description 2
239000002260 anti-inflammatory agent Substances 0.000 abstract description 2
238000004519 manufacturing process Methods 0.000 abstract description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
239000000047 product Substances 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
VVNCNSJFMMFHPL-VKHMYHEASA-N D-penicillamine Chemical compound CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 description 9
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
229960001639 penicillamine Drugs 0.000 description 9
230000003110 anti-inflammatory effect Effects 0.000 description 8
DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 8
229960001259 diclofenac Drugs 0.000 description 8
230000000694 effects Effects 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
238000010586 diagram Methods 0.000 description 6
238000000605 extraction Methods 0.000 description 6
238000000338 in vitro Methods 0.000 description 6
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230000010933 acylation Effects 0.000 description 5
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239000003242 anti bacterial agent Substances 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
239000000243 solution Substances 0.000 description 5
108090000790 Enzymes Proteins 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 4
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MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[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 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 description 4
239000002026 chloroform extract Substances 0.000 description 4
239000000284 extract Substances 0.000 description 4
150000002596 lactones Chemical class 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
102000003855 L-lactate dehydrogenase Human genes 0.000 description 3
108700023483 L-lactate dehydrogenases Proteins 0.000 description 3
229940088710 antibiotic agent Drugs 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
230000003115 biocidal effect Effects 0.000 description 3
238000006243 chemical reaction Methods 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
239000012043 crude product Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 2
108010055851 Acetylglucosaminidase Proteins 0.000 description 2
102000053187 Glucuronidase Human genes 0.000 description 2
108010060309 Glucuronidase Proteins 0.000 description 2
206010030113 Oedema Diseases 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
102100030122 Protein O-GlcNAcase Human genes 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
238000006640 acetylation reaction Methods 0.000 description 2
229960001138 acetylsalicylic acid Drugs 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
206010003246 arthritis Diseases 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000000099 in vitro assay Methods 0.000 description 2
238000005462 in vivo assay Methods 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
230000002132 lysosomal effect Effects 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229940049954 penicillin Drugs 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
HRKNNHYKWGYTEN-HOQMJRDDSA-N (2r,3s,4r,5r,8r,10r,11r,12s,13s,14r)-11-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,8,10,12,14-hexamethyl-1-oxa-6-azacyclopentadecan-15-one Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)NC[C@H](C)C[C@@](C)(O)[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 HRKNNHYKWGYTEN-HOQMJRDDSA-N 0.000 description 1
KYTWXIARANQMCA-PGYIPVOXSA-N (3r,4s,5s,6r,7r,9r,10z,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradec Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=N\O)/[C@H](C)C[C@@](C)(O)[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 KYTWXIARANQMCA-PGYIPVOXSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
238000006237 Beckmann rearrangement reaction Methods 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
101000651958 Crotalus durissus terrificus Snaclec crotocetin-1 Proteins 0.000 description 1
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[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 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 1
229930006677 Erythromycin A Natural products 0.000 description 1
208000009386 Experimental Arthritis Diseases 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
241000219061 Rheum Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
210000000170 cell membrane Anatomy 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
229960003276 erythromycin Drugs 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
210000000224 granular leucocyte Anatomy 0.000 description 1
230000009610 hypersensitivity Effects 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
210000000265 leukocyte Anatomy 0.000 description 1
239000003120 macrolide antibiotic agent Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
244000000010 microbial pathogen Species 0.000 description 1
244000005700 microbiome Species 0.000 description 1
ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
238000011176 pooling Methods 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000006485 reductive methylation reaction Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
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238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
210000001179 synovial fluid Anatomy 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- 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)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pain & Pain Management (AREA)
Pharmacology & Pharmacy (AREA)
Rheumatology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

CS253388A 1987-09-03 1988-04-13 Method of 10-dihydro-10-dexy-11-azarythronolides prepararation CS274462B2 (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CS181689A CS274497B2 (en)	1988-01-18	1989-03-23	Method of 10-dihydro-10-deoxi-11-azaerythronolides a preparation

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
YU163187A YU44641B (en)	1987-09-03	1987-09-03	Process for preparing derivatives of 10-dihydro-10-deoxo-11-azaeritronolides
YU85/88A YU45054B (en)	1988-01-18	1988-01-18	Process for preparing derivative of 10-dihydro-10-deoxo-11-azaerithronolide a

Publications (2)

Publication Number	Publication Date
CS253388A2 CS253388A2 (en)	1990-09-12
CS274462B2 true CS274462B2 (en)	1991-04-11

Family

ID=27130708

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS253388A CS274462B2 (en)	1987-09-03	1988-04-13	Method of 10-dihydro-10-dexy-11-azarythronolides prepararation

Country Status (12)

Country	Link
US (1)	US4886792A (pl)
EP (1)	EP0283055B1 (pl)
JP (1)	JPH01287076A (pl)
CN (1)	CN1020452C (pl)
BG (1)	BG49825A3 (pl)
CA (1)	CA1296000C (pl)
CS (1)	CS274462B2 (pl)
DE (1)	DE3860503D1 (pl)
HU (1)	HU198913B (pl)
PL (1)	PL155159B1 (pl)
RO (1)	RO105811B1 (pl)
RU (1)	RU2007398C1 (pl)

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US5194605A (en) *	1989-12-08	1993-03-16	Merck & Co., Inc.	Cyclic renin inhibitors containing 2-substituted (3S,4S)-4-amino-5-cyclohexyl-3-hydroxy pentanoic acid, 2-substituted (3S,4S)-5-cyclohexyl-3,4-di-hydroxy pentanoic acid or 2-substituted (4S,5S)-5-amino-6-cyclohexyl-4-hydroxyhexanoic acid or its analogs
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YU45590A (sh) *	1990-03-07	1992-07-20	PLIVA FARMACEVTSKA, KEMIJSKA, PREHRAMBENA I KOZMETIČKA INDUSTRIJA s.p.o.	Novi kompleksi odnosno helati antibiotika s dvovalentnim i/ili trovalentnim metalima i postupci za njihovo dobijanje
US5912331A (en) *	1991-03-15	1999-06-15	Merck & Co., Inc.	Process for the preparation of 9-deoxo-9(Z)-hydroxyiminoerythromycin A
US5985844A (en) *	1992-03-26	1999-11-16	Merck & Co., Inc.	Homoerythromycin A derivatives modified at the 4"-and 8A-positions
US5189159A (en) *	1992-04-02	1993-02-23	Merck & Co., Inc.	8a-AZA-8a-homoerythromycin cyclic iminoethers
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FR2691464B1 (fr) *	1992-05-21	1995-06-02	Roussel Uclaf	Nouveaux dérivés de la 1-oxa 6-azacyclopentadécane 13,15-dione, leur procédé de préparation et leur application comme médicaments.
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WO1999000125A1 (en) *	1997-06-27	1999-01-07	Merck & Co., Inc.	9a-aza-3-ketolides, compositions containing such compounds and methods of treatment
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AP1060A (en) *	1998-01-02	2002-04-23	Pfizer Prod Inc	Novel erythromycin derivatives.
AP9801420A0 (en) *	1998-01-02	1998-12-31	Pfizer Prod Inc	Novel macrolides.
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HRP20010018A2 (en)	2001-01-09	2002-12-31	Pliva D D	Novel anti-inflammatory compounds
AU2003237150A1 (en) *	2002-05-02	2003-11-17	University Hospitals Of Cleveland	Compositions and methods for treating inflammatory connective tissue diseases
US7109176B2 (en) *	2002-07-08	2006-09-19	Pliva-Istrazivacki Institut D.O.O.	Nonsteroidal anti-inflammatory substances, compositions and methods for their use
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
JP4790263B2 (ja) *	2002-07-08	2011-10-12	グラクソグループリミテッド	炎症性の疾患および病態を治療する新規な化合物、組成物および方法
ITMI20022292A1 (it) *	2002-10-29	2004-04-30	Zambon Spa	9a-azalidi ad attivita' antiinfiammatoria.
HRP20030324A2 (en) *	2003-04-24	2005-02-28	Pliva-Istra�iva�ki institut d.o.o.	Compounds of antiinflammatory effect
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ES2337915T3 (es)	2004-10-27	2010-04-30	Glaxosmithkline Istrazivacki Centar Zagreb D.O.O.	Conjugados con adtividad antiinflamatoria.
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CN101917850B (zh)	2007-10-25	2016-01-13	森普拉制药公司	大环内酯类抗菌剂的制备方法
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1988
- 1988-04-08 DE DE8888105626T patent/DE3860503D1/de not_active Expired - Lifetime
- 1988-04-08 EP EP88105626A patent/EP0283055B1/en not_active Expired - Lifetime
- 1988-04-08 HU HU881778A patent/HU198913B/hu not_active IP Right Cessation
- 1988-04-12 US US07/180,491 patent/US4886792A/en not_active Expired - Fee Related
- 1988-04-13 CA CA000564025A patent/CA1296000C/en not_active Expired - Lifetime
- 1988-04-13 CS CS253388A patent/CS274462B2/cs unknown
- 1988-04-14 RO RO144712A patent/RO105811B1/ro unknown
- 1988-04-22 PL PL1988272025A patent/PL155159B1/pl unknown
- 1988-04-26 BG BG083878A patent/BG49825A3/xx unknown
- 1988-05-16 RU SU884355672A patent/RU2007398C1/ru active
- 1988-05-20 CN CN88103197A patent/CN1020452C/zh not_active Expired - Fee Related
- 1988-07-21 JP JP63180450A patent/JPH01287076A/ja active Pending

Also Published As

Publication number	Publication date
CN1031703A (zh)	1989-03-15
CN1020452C (zh)	1993-05-05
EP0283055B1 (en)	1990-08-29
PL155159B1 (en)	1991-10-31
EP0283055A2 (en)	1988-09-21
CS253388A2 (en)	1990-09-12
CA1296000C (en)	1992-02-18
RU2007398C1 (ru)	1994-02-15
RO105811B1 (ro)	1992-12-30
HU198913B (en)	1989-12-28
BG49825A3 (en)	1992-02-14
JPH01287076A (ja)	1989-11-17
DE3860503D1 (de)	1990-10-04
EP0283055A3 (en)	1989-03-15
US4886792A (en)	1989-12-12
PL272025A1 (en)	1989-03-06
HUT47552A (en)	1989-03-28

Publication	Publication Date	Title
CS274462B2 (en)	1991-04-11	Method of 10-dihydro-10-dexy-11-azarythronolides prepararation
FR2473525A1 (fr)	1981-07-17	Nouvelles oximes derivees de l'erythromycine, leur procede de preparation et leur application comme medicaments
US4496717A (en)	1985-01-29	Erythromycin B derivatives
US4567163A (en)	1986-01-28	Salicyclic acid derivatives of N-acetylcysteine and pharmacological use thereof
CA1215713A (en)	1986-12-23	Substituted quinolinecarboxylic acid
EP0080819B1 (en)	1985-01-16	11-0-alkylerythromycin a derivatives
NZ231722A (en)	1992-04-28	Amphotericin beta derivatives, pharmaceutical compositions and preparation thereof
DK159450B (da)	1990-10-15	9-deoxo-9a-methyl-9a-aza-9a-homoerythromycin b og farmaceutisk acceptable syreadditionssalte deraf samt 9-deoxo-9a-aza-9a-homoerythromycin b til anvendelse som mellemprodukt ved fremstilling deraf
EP1307438B1 (en)	2005-09-07	Novel coumarin derivatives and the salts thereof, a process for the preparation thereof and their use in the pharmaceutical field
CA2196878A1 (en)	1996-02-22	Interleukin-5 production inhibitor
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WO2000002559A1 (en)	2000-01-20	Synthesis of aryl glucuronide of 2-hydroxy-n-(5-nitro-2-thiazolyl) benzamide, and pharmaceutical compositions comprising same
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US4283422A (en)	1981-08-11	3-Amino-4-homoisotwistane derivatives
AU2001283959A1 (en)	2002-05-09	Novel coumarin derivatives and the salts thereof, a process for the preparation thereof and their use in the pharmaceutical field
US3947453A (en)	1976-03-30	24-Oxo-14a-aza-D-homo-cholestadiene derivatives
CS274497B2 (en)	1991-04-11	Method of 10-dihydro-10-deoxi-11-azaerythronolides a preparation
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JPH06247996A (ja)	1994-09-06	６−ｏ−メチルエリスロマイシンａ誘導体
JPH0242821B2 (pl)	1990-09-26
DD272647A5 (de)	1989-10-18	Verfahren zur herstellung von 10-dihydro-10-deoxo-11-azaerythronolid-a-verbindungen