IL127833A - Preparation of the crystalline form II of clarithromycin - Google Patents

Preparation of the crystalline form II of clarithromycin

Info

Publication number: IL127833A
Authority: IL; Israel
Prior art keywords: methylerythromycin; carbon atoms; solvent; water; crystal form
Prior art date: 1996-07-29

Application number

IL12783397A

Other languages

English (en)

Hebrew (he)

Other versions

IL127833A0 (en

Original Assignee

Abbott Lab

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.)

1996-07-29

Filing date

1997-07-28

Publication date

2004-06-20

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=27102712&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=IL127833(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1996-07-29 Priority claimed from US08/681,695 external-priority patent/US5844105A/en

1997-07-28 Application filed by Abbott Lab filed Critical Abbott Lab

1999-10-28 Publication of IL127833A0 publication Critical patent/IL127833A0/xx

2004-06-20 Publication of IL127833A publication Critical patent/IL127833A/en

Links

AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin 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)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 title claims abstract description 108
229960002626 clarithromycin Drugs 0.000 title claims abstract description 73
239000013078 crystal Substances 0.000 title claims abstract description 53
238000002360 preparation method Methods 0.000 title abstract description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 78
239000002904 solvent Substances 0.000 claims abstract description 68
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 58
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 52
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 49
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 41
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 34
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 29
125000000217 alkyl group Chemical group 0.000 claims abstract description 23
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 claims abstract description 17
229930006677 Erythromycin A Natural products 0.000 claims abstract description 17
229960003276 erythromycin Drugs 0.000 claims abstract description 17
239000003960 organic solvent Substances 0.000 claims abstract description 17
125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims abstract description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
125000001424 substituent group Chemical group 0.000 claims abstract description 11
229940011051 isopropyl acetate Drugs 0.000 claims abstract description 10
GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims abstract description 10
150000001875 compounds Chemical class 0.000 claims abstract description 9
239000003880 polar aprotic solvent Substances 0.000 claims abstract description 6
238000000034 method Methods 0.000 claims description 47
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 24
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
238000001953 recrystallisation Methods 0.000 claims description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
150000001733 carboxylic acid esters Chemical class 0.000 claims description 14
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 10
150000002576 ketones Chemical class 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 9
150000001335 aliphatic alkanes Chemical class 0.000 claims description 8
150000001555 benzenes Chemical group 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
FFOPEPMHKILNIT-UHFFFAOYSA-N butyric acid isopropyl ester Natural products CCCC(=O)OC(C)C FFOPEPMHKILNIT-UHFFFAOYSA-N 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical group CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
239000008096 xylene Substances 0.000 claims description 5
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical group CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 4
229940072049 amyl acetate Drugs 0.000 claims description 4
PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims description 4
MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 3
BCUMPULZWNQMKD-UHFFFAOYSA-N methanol;propan-2-yl acetate Chemical compound OC.CC(C)OC(C)=O BCUMPULZWNQMKD-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 2
ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 claims description 2
BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 claims description 2
XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 claims description 2
KYTWXIARANQMCA-RWJQBGPGSA-N (3r,4s,5s,6r,7r,9r,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-oxacyclotetradecan-2 Chemical class O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=NO)[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-RWJQBGPGSA-N 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
150000002148 esters Chemical class 0.000 claims 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
229930195733 hydrocarbon Natural products 0.000 abstract description 11
239000004215 Carbon black (E152) Substances 0.000 abstract description 10
125000001475 halogen functional group Chemical group 0.000 abstract 3
239000007787 solid Substances 0.000 description 29
238000010992 reflux Methods 0.000 description 28
239000000706 filtrate Substances 0.000 description 23
239000000725 suspension Substances 0.000 description 23
238000001914 filtration Methods 0.000 description 13
239000000203 mixture Substances 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
239000005457 ice water Substances 0.000 description 8
238000000634 powder X-ray diffraction Methods 0.000 description 8
150000002430 hydrocarbons Chemical class 0.000 description 7
230000011987 methylation Effects 0.000 description 7
238000007069 methylation reaction Methods 0.000 description 7
239000000843 powder Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
125000006239 protecting group Chemical group 0.000 description 6
238000003386 deoximation reaction Methods 0.000 description 5
238000001757 thermogravimetry curve Methods 0.000 description 5
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000010511 deprotection reaction Methods 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000003814 drug Substances 0.000 description 4
238000002329 infrared spectrum Methods 0.000 description 4
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
150000002923 oximes Chemical class 0.000 description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
239000011877 solvent mixture Substances 0.000 description 3
MWBJRTBANFUBOX-SQYJNGITSA-N (3r,4s,5s,6r,7r,9r,10e,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-10-hydroxyimino-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclot 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)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MWBJRTBANFUBOX-SQYJNGITSA-N 0.000 description 2
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
125000004183 alkoxy alkyl group Chemical group 0.000 description 2
229940100198 alkylating agent Drugs 0.000 description 2
239000002168 alkylating agent Substances 0.000 description 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
XNLICIUVMPYHGG-UHFFFAOYSA-N methyl n-propyl ketone Natural products CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
238000006485 reductive methylation reaction Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
-1 6-O-methylerythromycin A oxime Chemical class 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
241000192125 Firmicutes Species 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
241000204031 Mycoplasma Species 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
241000187747 Streptomyces Species 0.000 description 1
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
OCLXJTCGWSSVOE-UHFFFAOYSA-N ethanol etoh Chemical compound CCO.CCO OCLXJTCGWSSVOE-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002443 hydroxylamines Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
238000011835 investigation Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
238000002955 isolation Methods 0.000 description 1
OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
239000003120 macrolide antibiotic agent Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
238000006146 oximation reaction Methods 0.000 description 1
125000005429 oxyalkyl group Chemical group 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
241001148471 unidentified anaerobic bacterium Species 0.000 description 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Medicinal Chemistry (AREA)
Biotechnology (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Molecular Biology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Genetics & Genomics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biochemistry (AREA)
Pulmonology (AREA)
Bioinformatics & Cheminformatics (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL12783397A 1996-07-29 1997-07-28 Preparation of the crystalline form II of clarithromycin IL127833A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US08/681,695 US5844105A (en)	1996-07-29	1996-07-29	Preparation of crystal form II of clarithromycin
US90027197A	1997-07-25	1997-07-25
PCT/US1997/013166 WO1998004574A1 (en)	1996-07-29	1997-07-28	Preparation of crystal form ii of clarithromycin

Publications (2)

Publication Number	Publication Date
IL127833A0 IL127833A0 (en)	1999-10-28
IL127833A true IL127833A (en)	2004-06-20

Family

ID=27102712

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL12783397A IL127833A (en)	1996-07-29	1997-07-28	Preparation of the crystalline form II of clarithromycin

Country Status (12)

Country	Link
EP (1)	EP0915899B1 (da)
JP (4)	JP4104660B2 (da)
KR (1)	KR100524214B1 (da)
AT (1)	ATE272646T1 (da)
AU (1)	AU733646B2 (da)
CA (1)	CA2261732C (da)
DE (3)	DE69730138T2 (da)
DK (1)	DK0915899T3 (da)
ES (1)	ES2173057T3 (da)
IL (1)	IL127833A (da)
PT (1)	PT915899E (da)
WO (1)	WO1998004574A1 (da)

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1997
- 1997-07-28 DE DE69730138T patent/DE69730138T2/de not_active Revoked
- 1997-07-28 IL IL12783397A patent/IL127833A/en not_active IP Right Cessation
- 1997-07-28 EP EP97934319A patent/EP0915899B1/en not_active Revoked
- 1997-07-28 JP JP50903898A patent/JP4104660B2/ja not_active Expired - Lifetime
- 1997-07-28 KR KR10-1999-7000654A patent/KR100524214B1/ko not_active Expired - Lifetime
- 1997-07-28 DE DE0000915899T patent/DE97934319T1/de active Pending
- 1997-07-28 PT PT97934319T patent/PT915899E/pt unknown
- 1997-07-28 AU AU37405/97A patent/AU733646B2/en not_active Expired
- 1997-07-28 CA CA002261732A patent/CA2261732C/en not_active Expired - Lifetime
- 1997-07-28 DK DK97934319T patent/DK0915899T3/da active
- 1997-07-28 DE DE29724846U patent/DE29724846U1/de not_active Expired - Lifetime
- 1997-07-28 AT AT97934319T patent/ATE272646T1/de active
- 1997-07-28 ES ES97934319T patent/ES2173057T3/es not_active Expired - Lifetime
- 1997-07-28 WO PCT/US1997/013166 patent/WO1998004574A1/en not_active Ceased
2005
- 2005-12-12 JP JP2005357782A patent/JP2006137765A/ja active Pending
2009
- 2009-06-15 JP JP2009141790A patent/JP2009242411A/ja not_active Withdrawn
2013
- 2013-04-03 JP JP2013077418A patent/JP2013151542A/ja active Pending

Also Published As

Publication number	Publication date
AU733646B2 (en)	2001-05-17
CA2261732C (en)	2001-07-24
JP2013151542A (ja)	2013-08-08
DK0915899T3 (da)	2004-11-29
AU3740597A (en)	1998-02-20
PT915899E (pt)	2004-11-30
CA2261732A1 (en)	1998-02-05
IL127833A0 (en)	1999-10-28
KR20000029591A (ko)	2000-05-25
ATE272646T1 (de)	2004-08-15
JP2006137765A (ja)	2006-06-01
JP4104660B2 (ja)	2008-06-18
DE97934319T1 (de)	2004-08-26
EP0915899A1 (en)	1999-05-19
ES2173057T1 (es)	2002-10-16
JP2009242411A (ja)	2009-10-22
JP2002514171A (ja)	2002-05-14
DE69730138D1 (de)	2004-09-30
KR100524214B1 (ko)	2005-11-01
EP0915899B1 (en)	2004-08-04
DE29724846U1 (de)	2004-12-16
WO1998004574A1 (en)	1998-02-05
DE69730138T2 (de)	2005-03-03
ES2173057T3 (es)	2004-11-16

Legal Events

Date	Code	Title
2010-10-31	FF	Patent granted
2010-11-30	KB	Patent renewed
2015-07-30	KB	Patent renewed
2018-02-28	EXP	Patent expired

Publication	Publication Date	Title
US5844105A (en)	1998-12-01	Preparation of crystal form II of clarithromycin
EP0915899B1 (en)	2004-08-04	Preparation of crystal form ii of clarithromycin
US5858986A (en)	1999-01-12	Crystal form I of clarithromycin
EP1280535B1 (en)	2005-02-09	Processes for preparing clarithromycin polymorphs
CA2277274C (en)	2003-05-27	Crystal form 0 of clarithromycin
AU783055B2 (en)	2005-09-22	Processes for preparing clarithromycin polymorphs and novel polymorph IV
CA2386527C (en)	2003-05-27	Crystal form i of clarithromycin
CA2488397C (en)	2008-07-08	Crystal form ii of clarithromycin
AU777612B2 (en)	2004-10-21	Crystal form I of clarithromycin
CA2386534C (en)	2003-05-27	Crystal form ii of clarithromycin and uses thereof
CA2526732A1 (en)	2004-12-09	Q-alkyl macrolide and azalide derivatives and regioselective process for their preparation
HK1118294A (en)	2009-02-06	Diphosphate salt of a 4"-substituted-9-deoxo-9a-aza-9a-homoerythromycin derivative and its pharmaceutical composition
HK1089182A (en)	2006-11-24	Crystal form i of clarithromycin