BG64357B1 - С-4"-заместени макролидни производни - Google Patents

С-4"-заместени макролидни производни Download PDF

Info

Publication number: BG64357B1
Authority: BG; Bulgaria
Prior art keywords: compound; groups; hydroxy; formula; alkyl
Prior art date: 1997-06-11

Application number

BG103969A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG103969A (en

Inventor

Brian Bronk

Takushi Kaneko

Michael LETAVIC

Hengmiao Cheng

Edward Glazer

Bingwei YANG

Original Assignee

Pfizer Products Inc.

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.)

1997-06-11

Filing date

1999-12-08

Publication date

2004-11-30

1999-12-08 Application filed by Pfizer Products Inc. filed Critical Pfizer Products Inc.

2000-07-31 Publication of BG103969A publication Critical patent/BG103969A/xx

2004-11-30 Publication of BG64357B1 publication Critical patent/BG64357B1/bg

Links

239000003120 macrolide antibiotic agent Substances 0.000 title description 19
150000001875 compounds Chemical class 0.000 claims abstract description 272
238000000034 method Methods 0.000 claims abstract description 57
150000003839 salts Chemical class 0.000 claims abstract description 39
238000002360 preparation method Methods 0.000 claims abstract description 19
208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 17
208000035143 Bacterial infection Diseases 0.000 claims abstract description 16
238000011282 treatment Methods 0.000 claims abstract description 12
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
-1 3-methoxypropyl Chemical group 0.000 claims description 79
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 78
229920006395 saturated elastomer Polymers 0.000 claims description 50
229910052799 carbon Inorganic materials 0.000 claims description 36
229910052739 hydrogen Inorganic materials 0.000 claims description 30
125000000217 alkyl group Chemical group 0.000 claims description 28
125000003118 aryl group Chemical group 0.000 claims description 28
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 27
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 20
125000005843 halogen group Chemical group 0.000 claims description 20
125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 19
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
125000001072 heteroaryl group Chemical group 0.000 claims description 18
125000001424 substituent group Chemical group 0.000 claims description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 14
229910052717 sulfur Inorganic materials 0.000 claims description 14
241000124008 Mammalia Species 0.000 claims description 13
125000004093 cyano group Chemical group *C#N 0.000 claims description 13
241000251468 Actinopterygii Species 0.000 claims description 12
206010037075 Protozoal infections Diseases 0.000 claims description 12
241000271566 Aves Species 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 claims description 9
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims description 8
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 7
125000002971 oxazolyl group Chemical group 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
239000012312 sodium hydride Substances 0.000 claims description 7
229910000104 sodium hydride Inorganic materials 0.000 claims description 7
125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 claims description 6
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 6
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
125000002950 monocyclic group Chemical group 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000003367 polycyclic group Chemical group 0.000 claims description 6
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 4
SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 claims description 3
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
229920002554 vinyl polymer Polymers 0.000 claims description 3
125000006019 1-methyl-1-propenyl group Chemical group 0.000 claims description 2
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 claims description 2
125000002346 iodo group Chemical group I* 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000001425 triazolyl group Chemical group 0.000 claims description 2
230000000844 anti-bacterial effect Effects 0.000 abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 113
239000000243 solution Substances 0.000 description 98
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
239000000460 chlorine Substances 0.000 description 43
239000011541 reaction mixture Substances 0.000 description 34
239000012267 brine Substances 0.000 description 30
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 30
208000015181 infectious disease Diseases 0.000 description 29
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
235000019439 ethyl acetate Nutrition 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
239000011734 sodium Chemical group 0.000 description 25
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
239000000203 mixture Substances 0.000 description 23
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
239000007787 solid Substances 0.000 description 20
239000002904 solvent Substances 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 17
238000010898 silica gel chromatography Methods 0.000 description 17
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 16
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
230000001580 bacterial effect Effects 0.000 description 15
239000000284 extract Substances 0.000 description 14
239000000047 product Substances 0.000 description 14
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 13
239000010410 layer Substances 0.000 description 13
125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000002585 base Substances 0.000 description 12
235000017557 sodium bicarbonate Nutrition 0.000 description 12
229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
238000003756 stirring Methods 0.000 description 12
238000012360 testing method Methods 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 11
238000004458 analytical method Methods 0.000 description 11
239000012044 organic layer Substances 0.000 description 11
230000002829 reductive effect Effects 0.000 description 11
238000000926 separation method Methods 0.000 description 11
229910052727 yttrium Inorganic materials 0.000 description 11
229910004298 SiO 2 Inorganic materials 0.000 description 10
239000002253 acid Substances 0.000 description 10
239000008186 active pharmaceutical agent Substances 0.000 description 10
238000001704 evaporation Methods 0.000 description 10
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
241001465754 Metazoa Species 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000012043 crude product Substances 0.000 description 9
230000008020 evaporation Effects 0.000 description 9
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
241000283690 Bos taurus Species 0.000 description 8
239000003153 chemical reaction reagent Substances 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
239000003960 organic solvent Substances 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
239000007858 starting material Substances 0.000 description 8
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class 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 7
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
241000606856 Pasteurella multocida Species 0.000 description 7
241000193996 Streptococcus pyogenes Species 0.000 description 7
229940079593 drug Drugs 0.000 description 7
238000001035 drying Methods 0.000 description 7
230000000694 effects Effects 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
241000193998 Streptococcus pneumoniae Species 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
125000003277 amino group Chemical group 0.000 description 6
PKSROMPNLONTJT-UHFFFAOYSA-N azanium;chloroform;methanol;hydroxide Chemical compound N.O.OC.ClC(Cl)Cl PKSROMPNLONTJT-UHFFFAOYSA-N 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
230000004048 modification Effects 0.000 description 6
238000012986 modification Methods 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
229910052700 potassium Inorganic materials 0.000 description 6
239000011591 potassium Substances 0.000 description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
238000000746 purification Methods 0.000 description 6
229940031000 streptococcus pneumoniae Drugs 0.000 description 6
241000588724 Escherichia coli Species 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
241001293418 Mannheimia haemolytica Species 0.000 description 5
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
241000191967 Staphylococcus aureus Species 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
239000007788 liquid Substances 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
239000001632 sodium acetate Substances 0.000 description 5
235000017281 sodium acetate Nutrition 0.000 description 5
239000000725 suspension Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
241000194017 Streptococcus Species 0.000 description 4
150000001414 amino alcohols Chemical class 0.000 description 4
239000003242 anti bacterial agent Substances 0.000 description 4
229940088710 antibiotic agent Drugs 0.000 description 4
229960004099 azithromycin Drugs 0.000 description 4
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
230000003197 catalytic effect Effects 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
238000001816 cooling Methods 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
238000005516 engineering process Methods 0.000 description 4
238000000605 extraction Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000012467 final product Substances 0.000 description 4
239000011777 magnesium Substances 0.000 description 4
229910052749 magnesium Inorganic materials 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
150000007522 mineralic acids Chemical class 0.000 description 4
231100000252 nontoxic Toxicity 0.000 description 4
230000003000 nontoxic effect Effects 0.000 description 4
150000007524 organic acids Chemical class 0.000 description 4
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 4
229910003446 platinum oxide Inorganic materials 0.000 description 4
238000003752 polymerase chain reaction Methods 0.000 description 4
PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
241000193403 Clostridium Species 0.000 description 3
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MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Tropical Medicine & Parasitology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

BG103969A 1997-06-11 1999-12-08 С-4"-заместени макролидни производни BG64357B1 (bg)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US4998097P	1997-06-11	1997-06-11

Publications (2)

Publication Number	Publication Date
BG103969A BG103969A (en)	2000-07-31
BG64357B1 true BG64357B1 (bg)	2004-11-30

Family

ID=21962765

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG103969A BG64357B1 (bg)	1997-06-11	1999-12-08	С-4"-заместени макролидни производни

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EP (1)	EP0988309B1 (is)
JP (1)	JP3262806B2 (is)
KR (1)	KR100369959B1 (is)
CN (1)	CN1145636C (is)
AP (1)	AP1189A (is)
AR (1)	AR013085A1 (is)
AT (1)	ATE310742T1 (is)
AU (1)	AU745006C (is)
BG (1)	BG64357B1 (is)
BR (1)	BR9810097A (is)
CA (1)	CA2293397C (is)
CO (1)	CO4950584A1 (is)
DE (1)	DE69832486T2 (is)
DZ (1)	DZ2515A1 (is)
EA (1)	EA002440B1 (is)
ES (1)	ES2251081T3 (is)
GT (1)	GT199800075A (is)
HN (1)	HN1998000074A (is)
HR (1)	HRP980315A2 (is)
HU (1)	HUP0004076A3 (is)
ID (1)	ID24530A (is)
IL (1)	IL132808A (is)
IS (1)	IS1979B (is)
MA (1)	MA24563A1 (is)
MY (1)	MY133027A (is)
NO (1)	NO315560B1 (is)
NZ (1)	NZ500652A (is)
OA (1)	OA11226A (is)
PA (1)	PA8452001A1 (is)
PE (1)	PE79999A1 (is)
PL (1)	PL337497A1 (is)
SK (1)	SK168299A3 (is)
TN (1)	TNSN98084A1 (is)
TW (2)	TW200418871A (is)
UA (1)	UA70298C2 (is)
UY (1)	UY25041A1 (is)
WO (1)	WO1998056801A1 (is)
YU (1)	YU62999A (is)
ZA (1)	ZA985016B (is)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6339063B1 (en)	1997-09-10	2002-01-15	Merck & Co., Inc.	9a-azalides as veterinary antimicrobial agents
EP1779853A3 (en) *	1997-09-10	2010-01-27	Merial Ltd.	9a-azalides as veterinary antimicrobial agents
DK1011689T3 (da) *	1997-09-10	2007-05-21	Merial Ltd	Anvendelse af 9a-azalider som veterinære antimikrobielle midler
AP9801420A0 (en) *	1998-01-02	1998-12-31	Pfizer Prod Inc	Novel macrolides.
US6043227A (en) *	1998-08-19	2000-03-28	Pfizer Inc.	C11 carbamates of macrolide antibacterials
EP1437360A3 (en) *	1998-08-19	2005-04-06	Pfizer Products Inc.	C11 Carbamates of macrolide antibacterials
US6100240A (en) *	1998-10-09	2000-08-08	Pfizer Inc	Macrolide derivatives
KR20010083944A (ko)	1998-11-03	2001-09-03	실버스타인 아써 에이.	신규 마크롤라이드 항생물질
CA2292359C (en) *	1999-01-28	2004-09-28	Pfizer Products Inc.	Novel azalides and methods of making same
US6764996B1 (en)	1999-08-24	2004-07-20	Abbott Laboratories	9a-azalides with antibacterial activity
PT1206476E (pt) *	1999-08-24	2006-05-31	Abbott Lab	9a-azalidos com actividade antibacteriana
MXPA02007305A (es) *	2000-01-27	2002-11-29	Pfizer Prod Inc	Composiciones antiboticas de azalida.
JP4104463B2 (ja) *	2001-04-27	2008-06-18	ファイザー・プロダクツ・インク	４’’−置換された−９−デオキソ−９ａ−アザ−９ａ−ホモエリスロマイシン誘導体を製造するための方法
JP2003040782A (ja) *	2001-05-31	2003-02-13	Pfizer Prod Inc	アザリド抗生物質組成物
PL374646A1 (en) *	2002-07-08	2005-10-31	Pliva-Istrazivacki Institutt D.O.O.	Novel nonsteroidal anti-inflammatory substances, compositions and methods for their use
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Also Published As

Publication number	Publication date
BR9810097A (pt)	2000-08-08
GT199800075A (es)	1999-11-30
KR20010013633A (ko)	2001-02-26
CA2293397A1 (en)	1998-12-17
CN1145636C (zh)	2004-04-14
BG103969A (en)	2000-07-31
OA11226A (en)	2003-07-16
ID24530A (id)	2000-07-20
WO1998056801A1 (en)	1998-12-17
HK1025974A1 (en)	2000-12-01
AR013085A1 (es)	2000-12-13
EA002440B1 (ru)	2002-04-25
KR100369959B1 (ko)	2003-02-12
EP0988309A1 (en)	2000-03-29
CN1259955A (zh)	2000-07-12
NO996107L (no)	2000-02-10
AP1189A (en)	2003-07-16
CO4950584A1 (es)	2000-09-01
HRP980315A2 (en)	1999-04-30
PE79999A1 (es)	1999-08-25
TWI224106B (en)	2004-11-21
JP3262806B2 (ja)	2002-03-04
IS1979B (is)	2005-01-14
AU7228198A (en)	1998-12-30
EP0988309B1 (en)	2005-11-23
EA199901014A1 (ru)	2000-06-26
MA24563A1 (fr)	1998-12-31
PA8452001A1 (es)	2000-05-24
TNSN98084A1 (fr)	2005-03-15
UA70298A (uk)	2004-10-15
IL132808A (en)	2004-08-31
AU745006C (en)	2006-02-23
DE69832486T2 (de)	2006-07-27
DE69832486D1 (de)	2005-12-29
HUP0004076A2 (hu)	2001-04-28
CA2293397C (en)	2004-08-31
PL337497A1 (en)	2000-08-28
TW200418871A (en)	2004-10-01
ZA985016B (en)	1999-12-10
NO996107D0 (no)	1999-12-10
YU62999A (sh)	2002-10-18
IS5250A (is)	1999-11-16
IL132808A0 (en)	2001-03-19
JP2000514097A (ja)	2000-10-24
NO315560B1 (no)	2003-09-22
HUP0004076A3 (en)	2003-05-28
AU745006B2 (en)	2002-03-07
ATE310742T1 (de)	2005-12-15
UA70298C2 (uk)	2004-10-15
SK168299A3 (en)	2000-09-12
UY25041A1 (es)	2000-09-29
NZ500652A (en)	2001-10-26
AP9801254A0 (en)	1998-06-30
HN1998000074A (es)	1999-01-08
ES2251081T3 (es)	2006-04-16
MY133027A (en)	2007-10-31
DZ2515A1 (fr)	2003-02-01

Publication	Publication Date	Title
EP0988309B1 (en)	2005-11-23	C-4''-substituted macrolide derivatives
US6420536B1 (en)	2002-07-16	4″-substituted-9-deoxo-9a-aza-9a-homoerythromycin a derivatives
EP1131331B1 (en)	2004-03-03	13-membered azalides and their use as antibiotic agents
US6576749B2 (en)	2003-06-10	C-4″-substituted macrolide derivatives
US6043227A (en)	2000-03-28	C11 carbamates of macrolide antibacterials
MXPA99011496A (en)	2000-07-01	C-4''-substituted macrolide derivatives
CZ438999A3 (cs)	2000-05-17	C-4"- substituované makrolidové deriváty
MXPA99011495A (en)	2001-05-17	4"-substituted-9-deoxo-9a-aza-9a-homoerythromycin a derivatives
HK1088014B (en)	2010-09-30	4"-substituted-9-deoxo-9a-aza-9a-homoerythromy a derivatives