KR20080032105A

KR20080032105A - 홉산의 무기염을 포함하는 조성물 및 홉산의 무기염생산방법

홉산의 무기염을 포함하는 조성물 및 홉산의 무기염생산방법 Download PDF

Info

Publication number: KR20080032105A
Authority: KR; South Korea
Prior art keywords: acid; composition; slurry; salt; calcium
Prior art date: 2005-06-21
Legal status : Withdrawn

Application number

KR1020087001569A

Other languages

English (en)

Korean (ko)

Inventor

케빈 케이. 매드센

마크 엠. 보서트

미츠노리 오노

Original Assignee

존 아이 하스 인코퍼레이티드

Priority date

2005-06-21

Filing date

2006-06-21

Publication date

2008-04-14

2006-06-21 Application filed by 존 아이 하스 인코퍼레이티드 filed Critical 존 아이 하스 인코퍼레이티드

2008-04-14 Publication of KR20080032105A publication Critical patent/KR20080032105A/ko

Status Withdrawn legal-status Critical Current

Links

239000002253 acid Substances 0.000 title claims abstract description 243
239000000203 mixture Substances 0.000 title claims abstract description 159
229910017053 inorganic salt Inorganic materials 0.000 title claims description 33
238000004519 manufacturing process Methods 0.000 title claims description 28
238000000034 method Methods 0.000 claims abstract description 126
230000008569 process Effects 0.000 claims abstract description 23
239000003814 drug Substances 0.000 claims abstract description 15
150000001875 compounds Chemical class 0.000 claims description 97
150000007513 acids Chemical class 0.000 claims description 75
QRDZSRWEULKVNW-UHFFFAOYSA-N 6-hydroxy-2-oxo-1h-quinoline-4-carboxylic acid Chemical compound C1=C(O)C=C2C(C(=O)O)=CC(=O)NC2=C1 QRDZSRWEULKVNW-UHFFFAOYSA-N 0.000 claims description 65
239000002002 slurry Substances 0.000 claims description 64
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 62
-1 coupulone Chemical compound 0.000 claims description 49
150000003839 salts Chemical class 0.000 claims description 43
238000001035 drying Methods 0.000 claims description 42
229910052749 magnesium Inorganic materials 0.000 claims description 41
239000011777 magnesium Substances 0.000 claims description 41
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 40
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 34
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 34
229910052791 calcium Inorganic materials 0.000 claims description 34
239000011575 calcium Substances 0.000 claims description 34
VMSLCPKYRPDHLN-UHFFFAOYSA-N (R)-Humulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)C(O)(CC=C(C)C)C1=O VMSLCPKYRPDHLN-UHFFFAOYSA-N 0.000 claims description 28
238000011282 treatment Methods 0.000 claims description 28
239000012670 alkaline solution Substances 0.000 claims description 27
230000002829 reductive effect Effects 0.000 claims description 27
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 26
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 26
229910052802 copper Inorganic materials 0.000 claims description 26
239000010949 copper Substances 0.000 claims description 26
239000007864 aqueous solution Substances 0.000 claims description 25
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
229910052700 potassium Inorganic materials 0.000 claims description 24
159000000007 calcium salts Chemical class 0.000 claims description 23
239000011734 sodium Substances 0.000 claims description 23
229910052744 lithium Inorganic materials 0.000 claims description 22
159000000003 magnesium salts Chemical class 0.000 claims description 22
229910052708 sodium Inorganic materials 0.000 claims description 22
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 21
201000010099 disease Diseases 0.000 claims description 21
229910052709 silver Inorganic materials 0.000 claims description 21
239000004332 silver Substances 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 18
239000011591 potassium Substances 0.000 claims description 18
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 17
229910052742 iron Inorganic materials 0.000 claims description 17
238000003756 stirring Methods 0.000 claims description 17
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 claims description 16
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 16
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201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 15
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229910052725 zinc Inorganic materials 0.000 claims description 15
239000011701 zinc Substances 0.000 claims description 15
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 14
229910052794 bromium Inorganic materials 0.000 claims description 14
150000001768 cations Chemical class 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 14
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 13
229910052788 barium Inorganic materials 0.000 claims description 13
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 13
229910052804 chromium Inorganic materials 0.000 claims description 13
239000011651 chromium Substances 0.000 claims description 13
229910017052 cobalt Inorganic materials 0.000 claims description 13
239000010941 cobalt Substances 0.000 claims description 13
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 13
LSDULPZJLTZEFD-UHFFFAOYSA-N lupulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O LSDULPZJLTZEFD-UHFFFAOYSA-N 0.000 claims description 13
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 13
238000002156 mixing Methods 0.000 claims description 13
229910052759 nickel Inorganic materials 0.000 claims description 13
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical group [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 12
229910052793 cadmium Inorganic materials 0.000 claims description 12
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 12
229910052740 iodine Inorganic materials 0.000 claims description 12
OLHLJBVALXTBSQ-UHFFFAOYSA-N Lupulone Natural products CC(C)CC(=O)C1C(=O)C(CC=C(C)C)C(=O)C(CC=C(C)C)(CC=C(C)C)C1=O OLHLJBVALXTBSQ-UHFFFAOYSA-N 0.000 claims description 10
230000003110 anti-inflammatory effect Effects 0.000 claims description 10
WPVSVIXDXMNGGN-UHFFFAOYSA-N beta-bitter acid Natural products CC(C)CC(=O)C1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(CC=C(C)C)=C1O WPVSVIXDXMNGGN-UHFFFAOYSA-N 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
229940124597 therapeutic agent Drugs 0.000 claims description 9
150000003751 zinc Chemical class 0.000 claims description 9
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 8
206010012601 diabetes mellitus Diseases 0.000 claims description 8
238000001914 filtration Methods 0.000 claims description 8
239000003937 drug carrier Substances 0.000 claims description 7
208000035143 Bacterial infection Diseases 0.000 claims description 6
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 claims description 6
208000022362 bacterial infectious disease Diseases 0.000 claims description 6
229910052943 magnesium sulfate Inorganic materials 0.000 claims description 6
235000019341 magnesium sulphate Nutrition 0.000 claims description 6
238000001694 spray drying Methods 0.000 claims description 6
208000002874 Acne Vulgaris Diseases 0.000 claims description 5
241000894006 Bacteria Species 0.000 claims description 5
206010000496 acne Diseases 0.000 claims description 5
238000001816 cooling Methods 0.000 claims description 5
238000002036 drum drying Methods 0.000 claims description 5
238000001291 vacuum drying Methods 0.000 claims description 5
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 4
206010020751 Hypersensitivity Diseases 0.000 claims description 4
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229910000019 calcium carbonate Inorganic materials 0.000 claims description 4
239000001110 calcium chloride Substances 0.000 claims description 4
229910001628 calcium chloride Inorganic materials 0.000 claims description 4
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 4
239000000920 calcium hydroxide Substances 0.000 claims description 4
229910001861 calcium hydroxide Inorganic materials 0.000 claims description 4
MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims description 4
208000019622 heart disease Diseases 0.000 claims description 4
QXPOWGXRDUFAQW-LJQANCHMSA-N Adlupulone Natural products O=C([C@@H](CC)C)C=1C(=O)C(C/C=C(\C)/C)(C/C=C(\C)/C)C(O)=C(C/C=C(\C)/C)C=1O QXPOWGXRDUFAQW-LJQANCHMSA-N 0.000 claims description 3
QXPOWGXRDUFAQW-UHFFFAOYSA-N adlupulone Chemical compound CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O QXPOWGXRDUFAQW-UHFFFAOYSA-N 0.000 claims description 3
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FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 claims description 3
229960000268 spectinomycin Drugs 0.000 claims description 3
UNFWWIHTNXNPBV-WXKVUWSESA-N spectinomycin Chemical compound O([C@@H]1[C@@H](NC)[C@@H](O)[C@H]([C@@H]([C@H]1O1)O)NC)[C@]2(O)[C@H]1O[C@H](C)CC2=O UNFWWIHTNXNPBV-WXKVUWSESA-N 0.000 claims description 3
229960001082 trimethoprim Drugs 0.000 claims description 3
IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 claims description 3
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HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 claims description 2
GEXOPZHAKQAGLU-UHFFFAOYSA-N Colupulone Natural products CC(C)C(=O)C1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(CC=C(C)C)=C1O GEXOPZHAKQAGLU-UHFFFAOYSA-N 0.000 claims description 2
241000186427 Cutibacterium acnes Species 0.000 claims description 2
JWCSIUVGFCSJCK-CAVRMKNVSA-N Disodium Moxalactam Chemical compound N([C@]1(OC)C(N2C(=C(CSC=3N(N=NN=3)C)CO[C@@H]21)C(O)=O)=O)C(=O)C(C(O)=O)C1=CC=C(O)C=C1 JWCSIUVGFCSJCK-CAVRMKNVSA-N 0.000 claims description 2
OJMMVQQUTAEWLP-UHFFFAOYSA-N Lincomycin Natural products CN1CC(CCC)CC1C(=O)NC(C(C)O)C1C(O)C(O)C(O)C(SC)O1 OJMMVQQUTAEWLP-UHFFFAOYSA-N 0.000 claims description 2
RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 claims description 2
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229930195708 Penicillin V Natural products 0.000 claims description 2
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208000026935 allergic disease Diseases 0.000 claims description 2
201000010105 allergic rhinitis Diseases 0.000 claims description 2
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AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims description 2
239000003242 anti bacterial agent Substances 0.000 claims description 2
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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 claims description 2
229940041011 carbapenems Drugs 0.000 claims description 2
QYIYFLOTGYLRGG-GPCCPHFNSA-N cefaclor Chemical compound C1([C@H](C(=O)N[C@@H]2C(N3C(=C(Cl)CS[C@@H]32)C(O)=O)=O)N)=CC=CC=C1 QYIYFLOTGYLRGG-GPCCPHFNSA-N 0.000 claims description 2
229960005361 cefaclor Drugs 0.000 claims description 2
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MLYYVTUWGNIJIB-BXKDBHETSA-N cefazolin Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 MLYYVTUWGNIJIB-BXKDBHETSA-N 0.000 claims description 2
229960001668 cefuroxime Drugs 0.000 claims description 2
JFPVXVDWJQMJEE-IZRZKJBUSA-N cefuroxime Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 JFPVXVDWJQMJEE-IZRZKJBUSA-N 0.000 claims description 2
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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 claims description 2
UNCDMWKTFLUPHZ-UHFFFAOYSA-N colupulone Chemical compound CC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O UNCDMWKTFLUPHZ-UHFFFAOYSA-N 0.000 claims description 2
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229960000433 latamoxef Drugs 0.000 claims description 2
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229960000515 nafcillin Drugs 0.000 claims description 2
GPXLMGHLHQJAGZ-JTDSTZFVSA-N nafcillin Chemical compound C1=CC=CC2=C(C(=O)N[C@@H]3C(N4[C@H](C(C)(C)S[C@@H]43)C(O)=O)=O)C(OCC)=CC=C21 GPXLMGHLHQJAGZ-JTDSTZFVSA-N 0.000 claims description 2
UWYHMGVUTGAWSP-JKIFEVAISA-N oxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=CC=CC=C1 UWYHMGVUTGAWSP-JKIFEVAISA-N 0.000 claims description 2
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BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 claims description 2
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MYPYJXKWCTUITO-LYRMYLQWSA-O vancomycin(1+) Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C([O-])=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)[NH2+]C)[C@H]1C[C@](C)([NH3+])[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-O 0.000 claims description 2
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