TWI293631B - - Google Patents
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- TWI293631B TWI293631B TW090107676A TW90107676A TWI293631B TW I293631 B TWI293631 B TW I293631B TW 090107676 A TW090107676 A TW 090107676A TW 90107676 A TW90107676 A TW 90107676A TW I293631 B TWI293631 B TW I293631B
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- 239000013078 crystal Substances 0.000 claims abstract description 135
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 10
- 238000002425 crystallisation Methods 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 230000008025 crystallization Effects 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 20
- -1 aminosulfonylaminomethyl Chemical group 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 239000000843 powder Substances 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 230000002079 cooperative effect Effects 0.000 claims description 7
- FYZUENZXIZCLAZ-UHFFFAOYSA-N 2-methylhept-2-enoic acid Chemical compound CCCCC=C(C)C(O)=O FYZUENZXIZCLAZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000004458 analytical method Methods 0.000 claims description 6
- 238000002347 injection Methods 0.000 claims description 6
- 239000007924 injection Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 238000002050 diffraction method Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
- 239000005864 Sulphur Substances 0.000 claims 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
- 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 235000011149 sulphuric acid Nutrition 0.000 claims 1
- 239000001117 sulphuric acid Substances 0.000 claims 1
- XLJMOHKQRRPBDS-IENPIDJESA-N (5S)-4-pyrrolidin-1-ylsulfanyl-1-azabicyclo[3.2.0]hept-2-en-7-one Chemical class N1(CCCC1)SC1C=CN2[C@H]1CC2=O XLJMOHKQRRPBDS-IENPIDJESA-N 0.000 abstract 1
- 238000005259 measurement Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 11
- 238000002441 X-ray diffraction Methods 0.000 description 10
- 238000003860 storage Methods 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 238000004321 preservation Methods 0.000 description 6
- 239000012086 standard solution Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000004682 monohydrates Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 3
- 240000004244 Cucurbita moschata Species 0.000 description 3
- 235000009854 Cucurbita moschata Nutrition 0.000 description 3
- 235000009852 Cucurbita pepo Nutrition 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
- 238000000354 decomposition reaction Methods 0.000 description 3
- 150000004683 dihydrates Chemical class 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000012488 sample solution Substances 0.000 description 3
- 235000020354 squash Nutrition 0.000 description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- PMMYEEVYMWASQN-UHFFFAOYSA-N 4-hydroxyproline Chemical compound OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 206010036790 Productive cough Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- FKCMADOPPWWGNZ-YUMQZZPRSA-N [(2r)-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@H](N)C(=O)N1CCC[C@H]1B(O)O FKCMADOPPWWGNZ-YUMQZZPRSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- AVAACINZEOAHHE-VFZPANTDSA-N doripenem Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)S[C@@H]1CN[C@H](CNS(N)(=O)=O)C1 AVAACINZEOAHHE-VFZPANTDSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229960005489 paracetamol Drugs 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 229940127557 pharmaceutical product Drugs 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 208000024794 sputum Diseases 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 239000003860 topical agent Substances 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241000206601 Carnobacterium mobile Species 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 244000241257 Cucumis melo Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007707 calorimetry Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001782 cephems Chemical class 0.000 description 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000012812 general test Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 229910001410 inorganic ion Inorganic materials 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 229940127554 medical product Drugs 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229940097496 nasal spray Drugs 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- UXXOQTFUSYIPBI-UHFFFAOYSA-N nonadecyl decanoate Chemical compound C(CCCCCCCCC)(=O)OCCCCCCCCCCCCCCCCCCC UXXOQTFUSYIPBI-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
- C07D477/16—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hetero atoms or carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 3
- C07D477/20—Sulfur atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000099868 | 2000-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI293631B true TWI293631B (OSRAM) | 2008-02-21 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW090107676A TWI293631B (OSRAM) | 2000-03-31 | 2001-03-30 |
Country Status (17)
| Country | Link |
|---|---|
| US (5) | US20030153191A1 (OSRAM) |
| EP (1) | EP1270575B1 (OSRAM) |
| JP (1) | JP3375084B2 (OSRAM) |
| KR (1) | KR100472842B1 (OSRAM) |
| CN (1) | CN1192030C (OSRAM) |
| AT (1) | ATE304014T1 (OSRAM) |
| AU (2) | AU4469201A (OSRAM) |
| BR (1) | BRPI0109712B8 (OSRAM) |
| CA (1) | CA2404703C (OSRAM) |
| CY (2) | CY1105674T1 (OSRAM) |
| DE (1) | DE60113243T2 (OSRAM) |
| DK (1) | DK1270575T3 (OSRAM) |
| ES (1) | ES2252205T3 (OSRAM) |
| MX (1) | MXPA02009592A (OSRAM) |
| TW (1) | TWI293631B (OSRAM) |
| WO (1) | WO2001072750A1 (OSRAM) |
| ZA (1) | ZA200207675B (OSRAM) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3375084B2 (ja) * | 2000-03-31 | 2003-02-10 | 塩野義製薬株式会社 | ピロリジルチオカルバペネム誘導体の新型結晶 |
| JP5004355B2 (ja) * | 2001-05-10 | 2012-08-22 | 塩野義製薬株式会社 | アセチルチオピロリジン誘導体の製法 |
| CN1608066A (zh) * | 2001-11-16 | 2005-04-20 | 兰贝克赛实验室有限公司 | 结晶亚胺培南的制备方法 |
| TWI353855B (en) * | 2005-05-26 | 2011-12-11 | Shionogi & Co | Method for preparing an aqueous solution of doripe |
| KR20090007572A (ko) * | 2006-04-28 | 2009-01-19 | 카네카 코포레이션 | 카르바페넴 항생 물질 중간체의 개량된 정석 방법 |
| CN101466713A (zh) * | 2006-07-03 | 2009-06-24 | 成都地奥九泓制药厂 | 多尼培南的新结晶及其制备方法和用途 |
| CN101191787B (zh) * | 2006-11-21 | 2011-07-27 | 上海医药工业研究院 | 高效液相色谱法测定多利培南含量的方法 |
| WO2009118680A1 (en) | 2008-03-24 | 2009-10-01 | Ranbaxy Laboratories Limited | Process for the preparation of sterile doripenem |
| CN103025733B (zh) * | 2010-06-03 | 2015-11-25 | 山东轩竹医药科技有限公司 | 碳青霉烯类衍生物或其水合物的晶型及其制备方法与用途 |
| CN102977101A (zh) * | 2011-09-07 | 2013-03-20 | 中国人民解放军军事医学科学院毒物药物研究所 | 多尼培南一水合物、其药物组合物、其制备方法和用途 |
| CN102285988B (zh) * | 2011-09-08 | 2012-09-05 | 上海希迈医药科技有限公司 | 一种多尼培南水合物晶体及其制备方法 |
| WO2013068910A1 (en) * | 2011-11-08 | 2013-05-16 | Ranbaxy Laboratories Limited | Process for the preparation of polymorphs of doripenem |
| CN104072497B (zh) * | 2013-03-29 | 2017-10-03 | 石药集团中奇制药技术（石家庄）有限公司 | 一种多尼培南新结晶及其制备方法 |
| CN103389347B (zh) * | 2013-07-26 | 2015-12-09 | 深圳市海滨制药有限公司 | 高效液相色谱法测定多尼培南的方法 |
| WO2015167148A1 (ko) * | 2014-04-28 | 2015-11-05 | 제이더블유중외제약 주식회사 | 도리페넴의 신규한 결정 및 이의 제조방법 |
| KR20160007679A (ko) | 2016-01-04 | 2016-01-20 | 제일약품주식회사 | 도리페넴의 신규한 결정형 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5317016A (en) * | 1991-08-20 | 1994-05-31 | Shionogi Seiyaku Kabushiki Kaisha | Pyrrolidylthiocarbapenem derivative |
| US5539102A (en) * | 1992-02-21 | 1996-07-23 | Shionogi Seiyaku Kabushiki Kaisha | Production method for sulfamide |
| DE69528166T2 (de) * | 1994-05-02 | 2003-04-30 | Shionogi & Co., Ltd. | Kristalline pyrrolidylthiocarbapenem derivate, lyophilisierste präparationen dieser kristalle und verfahren zu deren herstellung |
| JP3558684B2 (ja) * | 1994-06-28 | 2004-08-25 | 塩野義製薬株式会社 | ピロリジルチオカルバペネム誘導体の乾燥方法 |
| JP3375084B2 (ja) * | 2000-03-31 | 2003-02-10 | 塩野義製薬株式会社 | ピロリジルチオカルバペネム誘導体の新型結晶 |
| WO2004072073A1 (ja) * | 2003-02-14 | 2004-08-26 | Shionogi & Co., Ltd. | カルバペネム合成中間体の結晶 |
| WO2010097686A1 (en) | 2009-02-26 | 2010-09-02 | Orchid Chemicals & Pharmaceuticals Ltd | An improved process for the preparation of carbapenem antibiotic |
-
2001
- 2001-03-30 JP JP2001570660A patent/JP3375084B2/ja not_active Expired - Lifetime
- 2001-03-30 BR BR0109712-1 patent/BRPI0109712B8/pt not_active IP Right Cessation
- 2001-03-30 CN CNB01810309XA patent/CN1192030C/zh not_active Ceased
- 2001-03-30 AU AU4469201A patent/AU4469201A/xx active Pending
- 2001-03-30 KR KR10-2002-7012979A patent/KR100472842B1/ko not_active Expired - Lifetime
- 2001-03-30 TW TW090107676A patent/TWI293631B/zh not_active IP Right Cessation
- 2001-03-30 ES ES01917764T patent/ES2252205T3/es not_active Expired - Lifetime
- 2001-03-30 AT AT01917764T patent/ATE304014T1/de active
- 2001-03-30 MX MXPA02009592A patent/MXPA02009592A/es active IP Right Grant
- 2001-03-30 WO PCT/JP2001/002834 patent/WO2001072750A1/ja active IP Right Grant
- 2001-03-30 AU AU2001244692A patent/AU2001244692B2/en not_active Ceased
- 2001-03-30 DK DK01917764T patent/DK1270575T3/da active
- 2001-03-30 CA CA002404703A patent/CA2404703C/en not_active Expired - Fee Related
- 2001-03-30 DE DE60113243T patent/DE60113243T2/de not_active Expired - Lifetime
- 2001-03-30 EP EP01917764A patent/EP1270575B1/en not_active Expired - Lifetime
- 2001-03-30 US US10/240,465 patent/US20030153191A1/en not_active Abandoned
-
2002
- 2002-09-25 ZA ZA200207675A patent/ZA200207675B/xx unknown
-
2005
- 2005-11-28 CY CY20051101453T patent/CY1105674T1/el unknown
-
2006
- 2006-11-10 US US11/595,348 patent/US20070060562A1/en not_active Abandoned
-
2008
- 2008-02-05 US US12/012,932 patent/US8247402B2/en not_active Expired - Fee Related
-
2009
- 2009-01-23 CY CY200900001C patent/CY2009001I1/el unknown
-
2012
- 2012-08-14 US US13/585,611 patent/US20130059831A1/en not_active Abandoned
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2014
- 2014-02-21 US US14/187,010 patent/US9221823B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20130059831A1 (en) | 2013-03-07 |
| ZA200207675B (en) | 2003-09-25 |
| CN1192030C (zh) | 2005-03-09 |
| WO2001072750A1 (fr) | 2001-10-04 |
| EP1270575B1 (en) | 2005-09-07 |
| US9221823B2 (en) | 2015-12-29 |
| KR100472842B1 (ko) | 2005-03-10 |
| US20030153191A1 (en) | 2003-08-14 |
| US20080207586A1 (en) | 2008-08-28 |
| EP1270575A4 (en) | 2004-02-18 |
| DE60113243D1 (de) | 2005-10-13 |
| AU2001244692B2 (en) | 2004-10-14 |
| CY1105674T1 (el) | 2010-07-28 |
| DE60113243T2 (de) | 2006-02-16 |
| JP3375084B2 (ja) | 2003-02-10 |
| ES2252205T3 (es) | 2006-05-16 |
| KR20020087446A (ko) | 2002-11-22 |
| EP1270575A1 (en) | 2003-01-02 |
| BRPI0109712B8 (pt) | 2021-05-25 |
| US8247402B2 (en) | 2012-08-21 |
| BRPI0109712B1 (pt) | 2017-10-24 |
| US20150031664A1 (en) | 2015-01-29 |
| BR0109712A (pt) | 2003-04-29 |
| CN1432016A (zh) | 2003-07-23 |
| CA2404703C (en) | 2007-06-05 |
| AU4469201A (en) | 2001-10-08 |
| CY2009001I2 (el) | 2009-11-04 |
| CY2009001I1 (el) | 2009-11-04 |
| DK1270575T3 (da) | 2006-01-16 |
| ATE304014T1 (de) | 2005-09-15 |
| MXPA02009592A (es) | 2003-03-12 |
| CA2404703A1 (en) | 2002-09-26 |
| US20070060562A1 (en) | 2007-03-15 |
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