NL193136C - Kristallijn hydraat van een oraal cefalosporine derivaat, werkwijze voor het bereiden daarvan en farmaceutisch product daaruit. - Google Patents

Kristallijn hydraat van een oraal cefalosporine derivaat, werkwijze voor het bereiden daarvan en farmaceutisch product daaruit. Download PDF

Info

Publication number: NL193136C
Authority: NL; Netherlands
Prior art keywords: solution; crystalline hydrate; derivative; water; hydrate
Prior art date: 1986-07-02

Application number

NL8701507A

Other languages

English (en)

Dutch (nl)

Other versions

NL193136B (nl

NL8701507A (nl

Original Assignee

Shionogi & Co

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.)

1986-07-02

Filing date

1987-06-26

Publication date

1998-12-04

1986-07-02 Priority claimed from JP61156954A external-priority patent/JP2544113B2/ja

1986-09-12 Priority claimed from JP21626086A external-priority patent/JPH0717651B2/ja

1987-06-26 Application filed by Shionogi & Co filed Critical Shionogi & Co

1988-02-01 Publication of NL8701507A publication Critical patent/NL8701507A/nl

1998-08-03 Publication of NL193136B publication Critical patent/NL193136B/xx

1998-12-04 Application granted granted Critical

1998-12-04 Publication of NL193136C publication Critical patent/NL193136C/nl

Links

238000000034 method Methods 0.000 title claims description 22
239000000825 pharmaceutical preparation Substances 0.000 title claims description 8
229940127557 pharmaceutical product Drugs 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title description 5
229940124588 oral cephalosporin Drugs 0.000 title description 3
239000000243 solution Substances 0.000 claims description 39
239000002775 capsule Substances 0.000 claims description 38
108010010803 Gelatin Proteins 0.000 claims description 30
229920000159 gelatin Polymers 0.000 claims description 30
239000008273 gelatin Substances 0.000 claims description 30
235000019322 gelatine Nutrition 0.000 claims description 30
235000011852 gelatine desserts Nutrition 0.000 claims description 30
239000013078 crystal Substances 0.000 claims description 21
238000001035 drying Methods 0.000 claims description 19
238000002441 X-ray diffraction Methods 0.000 claims description 9
239000007864 aqueous solution Substances 0.000 claims description 8
239000007903 gelatin capsule Substances 0.000 claims description 8
229930186147 Cephalosporin Natural products 0.000 claims description 7
229940124587 cephalosporin Drugs 0.000 claims description 7
150000001780 cephalosporins Chemical class 0.000 claims description 7
230000002378 acidificating effect Effects 0.000 claims description 5
-1 2-aminothiazol-4-yl Chemical group 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
239000011261 inert gas Substances 0.000 claims description 4
239000007789 gas Substances 0.000 claims description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
239000000203 mixture Substances 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
239000000843 powder Substances 0.000 description 11
239000007858 starting material Substances 0.000 description 10
230000000694 effects Effects 0.000 description 9
150000004683 dihydrates Chemical class 0.000 description 7
239000004408 titanium dioxide Substances 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
239000001913 cellulose Substances 0.000 description 6
229920002678 cellulose Polymers 0.000 description 6
229940079593 drug Drugs 0.000 description 6
239000003814 drug Substances 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
238000007789 sealing Methods 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
150000004684 trihydrates Chemical class 0.000 description 6
239000002585 base Substances 0.000 description 5
230000000052 comparative effect Effects 0.000 description 5
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 5
239000000725 suspension Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
230000000844 anti-bacterial effect Effects 0.000 description 4
239000000945 filler Substances 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000007902 hard capsule Substances 0.000 description 4
239000000314 lubricant Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
238000012360 testing method Methods 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000000996 additive effect Effects 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
239000002274 desiccant Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 3
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
229920000053 polysorbate 80 Polymers 0.000 description 3
230000007704 transition Effects 0.000 description 3
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
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 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-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
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
230000003078 antioxidant effect Effects 0.000 description 2
239000001045 blue dye Substances 0.000 description 2
239000004203 carnauba wax Substances 0.000 description 2
235000013869 carnauba wax Nutrition 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
RAGZEDHHTPQLAI-UHFFFAOYSA-L disodium;2',4',5',7'-tetraiodo-3-oxospiro[2-benzofuran-1,9'-xanthene]-3',6'-diolate Chemical compound [Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC(I)=C([O-])C(I)=C1OC1=C(I)C([O-])=C(I)C=C21 RAGZEDHHTPQLAI-UHFFFAOYSA-L 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000001630 malic acid Substances 0.000 description 2
235000011090 malic acid Nutrition 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000000049 pigment Substances 0.000 description 2
229940068968 polysorbate 80 Drugs 0.000 description 2
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
230000000717 retained effect Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
HGBLOOKUWXBZBL-UHFFFAOYSA-N 2-benzyl-6-methoxyphenol Chemical compound COC1=CC=CC(CC=2C=CC=CC=2)=C1O HGBLOOKUWXBZBL-UHFFFAOYSA-N 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
229910016523 CuKa Inorganic materials 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
241001465754 Metazoa Species 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
150000008043 acidic salts Chemical class 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
239000003570 air Substances 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
229910021538 borax Inorganic materials 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 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
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
238000007908 dry granulation Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000003780 insertion Methods 0.000 description 1
230000037431 insertion Effects 0.000 description 1
238000011835 investigation Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000004571 lime Substances 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
229960003966 nicotinamide Drugs 0.000 description 1
235000005152 nicotinamide Nutrition 0.000 description 1
239000011570 nicotinamide Substances 0.000 description 1
150000002825 nitriles Chemical class 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
239000003921 oil Substances 0.000 description 1
229940126701 oral medication Drugs 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229950008882 polysorbate Drugs 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000005855 radiation Effects 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000004328 sodium tetraborate Substances 0.000 description 1
235000010339 sodium tetraborate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000013112 stability test Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
238000001757 thermogravimetry curve Methods 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
238000002211 ultraviolet spectrum Methods 0.000 description 1
239000001043 yellow dye Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cephalosporin Compounds (AREA)
Medicinal Preparation (AREA)

NL8701507A 1986-07-02 1987-06-26 Kristallijn hydraat van een oraal cefalosporine derivaat, werkwijze voor het bereiden daarvan en farmaceutisch product daaruit. NL193136C (nl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP15695486		1986-07-02
JP61156954A JP2544113B2 (ja)	1986-07-02	1986-07-02	安定なカプセル製剤
JP21626086A JPH0717651B2 (ja)	1986-09-12	1986-09-12	経口投与用セフアロスポリン水和物結晶
JP21626086		1986-09-12

Publications (3)

Publication Number	Publication Date
NL8701507A NL8701507A (nl)	1988-02-01
NL193136B NL193136B (nl)	1998-08-03
NL193136C true NL193136C (nl)	1998-12-04

Family

ID=26484565

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8701507A NL193136C (nl)	1986-07-02	1987-06-26	Kristallijn hydraat van een oraal cefalosporine derivaat, werkwijze voor het bereiden daarvan en farmaceutisch product daaruit.

Country Status (27)

Country	Link
US (2)	US4812561A (da)
KR (1)	KR950005302B1 (da)
CN (1)	CN1015106B (da)
AR (1)	AR243893A1 (da)
AT (1)	AT392472B (da)
AU (1)	AU594167B2 (da)
BE (1)	BE1001691A4 (da)
CA (1)	CA1283405C (da)
CH (1)	CH672788A5 (da)
DE (1)	DE3721913A1 (da)
DK (1)	DK161080C (da)
ES (2)	ES2004952A6 (da)
FI (1)	FI89052C (da)
FR (1)	FR2601014B1 (da)
GB (1)	GB2192183B (da)
GR (1)	GR871014B (da)
HK (1)	HK47893A (da)
HU (1)	HU200777B (da)
IE (1)	IE59613B1 (da)
IL (1)	IL83059A (da)
IT (1)	IT1211469B (da)
NL (1)	NL193136C (da)
NO (1)	NO170889C (da)
NZ (1)	NZ220764A (da)
PL (1)	PL159180B1 (da)
RU (1)	RU1829932C (da)
SE (1)	SE466257B (da)

Families Citing this family (68)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5089270A (en) *	1990-05-15	1992-02-18	L. Perrigo Company	Capsule-shaped tablet
CZ283428B6 (cs) *	1992-04-30	1998-04-15	Schering Corporation	Stabilní hydratovaný suchý práškový cefalosporin vhodný pro orální aplikaci ve formě suspenze
ATE528327T1 (de) *	1998-10-27	2011-10-15	Westlake Longview Corp	Verfahren zur polymerisierung von olefine.
US6565882B2 (en) *	2000-02-24	2003-05-20	Advancis Pharmaceutical Corp	Antibiotic composition with inhibitor
US6544555B2 (en) *	2000-02-24	2003-04-08	Advancis Pharmaceutical Corp.	Antibiotic product, use and formulation thereof
AT412213B (de) *	2000-05-30	2004-11-25	Sandoz Ag	Verfahren zur trocknung von amoxicillin oder amoxicillin-hältigen, oralen, festen pharmazeutischen zusammensetzungen unter verwendung eines gases mit einer definierten gasfeuchte
US20020068078A1 (en) *	2000-10-13	2002-06-06	Rudnic Edward M.	Antifungal product, use and formulation thereof
US6541014B2 (en) *	2000-10-13	2003-04-01	Advancis Pharmaceutical Corp.	Antiviral product, use and formulation thereof
US20020197314A1 (en) *	2001-02-23	2002-12-26	Rudnic Edward M.	Anti-fungal composition
US7842791B2 (en) *	2002-12-19	2010-11-30	Nancy Jean Britten	Dispersible pharmaceutical compositions
AU2004258949B2 (en) *	2003-07-21	2011-02-10	Shionogi, Inc.	Antibiotic product, use and formulation thereof
JP2006528185A (ja) *	2003-07-21	2006-12-14	アドバンシスファーマスーティカルコーポレイション	抗生物質製剤、その使用法及び作成方法
AU2004258953B2 (en) *	2003-07-21	2011-02-10	Shionogi, Inc.	Antibiotic product, use and formulation thereof
CA2535177A1 (en) *	2003-08-11	2005-02-24	Advancis Pharmaceutical Corporation	Robust pellet
US8062672B2 (en) *	2003-08-12	2011-11-22	Shionogi Inc.	Antibiotic product, use and formulation thereof
AU2004270170B2 (en) *	2003-08-29	2011-01-27	Shionogi, Inc.	Antibiotic product, use and formulation thereof
CA2538064C (en) *	2003-09-15	2013-12-17	Advancis Pharmaceutical Corporation	Antibiotic product, use and formulation thereof
AU2004308419B2 (en) *	2003-12-24	2011-06-02	Victory Pharma, Inc.	Enhanced absorption of modified release dosage forms
CA2572292A1 (en) *	2004-07-02	2006-02-09	Advancis Pharmaceutical Corporation	Tablet for pulsed delivery
US20110104109A1 (en) *	2005-07-13	2011-05-05	Frank Bennett	Tetracyclic indole derivatives and their use for treating or preventing viral infections
JP5688877B2 (ja)	2005-11-11	2015-03-25	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	癌疾患の治療用キナゾリン誘導体
US8357394B2 (en)	2005-12-08	2013-01-22	Shionogi Inc.	Compositions and methods for improved efficacy of penicillin-type antibiotics
US8778924B2 (en) *	2006-12-04	2014-07-15	Shionogi Inc.	Modified release amoxicillin products
US8299052B2 (en) *	2006-05-05	2012-10-30	Shionogi Inc.	Pharmaceutical compositions and methods for improved bacterial eradication
AR062927A1 (es) *	2006-10-11	2008-12-17	Bayer Healthcare Ag	4- [4-( [ [ 4- cloro-3-( trifluorometil) fenil) carbamoil] amino] -3- fluorofenoxi) -n- metilpiridin-2- carboxamida monohidratada
WO2008082488A1 (en) *	2006-12-22	2008-07-10	Schering Corporation	4, 5-ring annulated indole derivatives for treating or preventing of hcv and related viral infections
CN101611025A (zh)	2006-12-22	2009-12-23	先灵公司	5,6-环化的吲哚衍生物及其使用方法
US8557848B2 (en)	2006-12-22	2013-10-15	Merck Sharp & Dohme Corp.	4,5-ring annulated indole derivatives for treating or preventing of HCV and related viral infections
WO2009032116A1 (en) *	2007-08-29	2009-03-12	Schering Corporation	2, 3-substituted indole derivatives for treating viral infections
ATE541845T1 (de) *	2007-08-29	2012-02-15	Schering Corp	2,3-substituierte azaindolderivate zur behandlung von virusinfektionen
EP2408761B1 (en) *	2007-08-29	2014-01-01	Merck Sharp & Dohme Corp.	Substituted indole derivatives and methods of use thereof
US8377928B2 (en) *	2007-11-16	2013-02-19	Merck Sharp & Dohme Corp.	3-aminosulfonyl substituted indole derivatives and methods of use thereof
MX2010005356A (es) *	2007-11-16	2010-05-27	Schering Corp	Derivados de indol 3-heterociclico sustituidos y metodos de uso de los mismos.
MX2010013630A (es) *	2008-06-13	2010-12-21	Schering Corp	Derivados triciclicos de indol y metodos de uso de los mismos.
TW201020245A (en)	2008-08-20	2010-06-01	Schering Corp	Ethynyl-substituted pyridine and pyrimidine derivatives and their use in treating viral infections
US8470834B2 (en)	2008-08-20	2013-06-25	Merck Sharp & Dohme Corp.	AZO-substituted pyridine and pyrimidine derivatives and their use in treating viral infections
EP2326627A1 (en)	2008-08-20	2011-06-01	Schering Corporation	Substituted pyridine and pyrimidine derivatives and their use in treating viral infections
ES2439009T3 (es)	2008-08-20	2014-01-21	Merck Sharp & Dohme Corp.	Derivados de piridina y pirimidina sustituidos con etenilo y su uso en el tratamiento de infecciones virales
JP2012528195A (ja)	2009-05-29	2012-11-12	メルク・シャープ・アンド・ドーム・コーポレーション	Ｃ型肝炎などの疾患を処置するための３つの結合アリール部分で構成された抗菌性化合物
PT2451445T (pt)	2009-07-06	2019-07-10	Boehringer Ingelheim Int	Processo para secagem de bibw2992, dos seus sais e de formulações farmacêuticas sólidas compreendendo este ingrediente ativo
EP2503881B1 (en)	2009-11-25	2015-05-13	Merck Sharp & Dohme Corp.	Fused tricyclic compounds and derivatives thereof useful for the treatment of viral diseases
AU2010341537A1 (en)	2009-12-22	2012-08-09	Merck Sharp & Dohme Corp.	Fused Tricyclic Compounds and methods of use thereof for the treatment of viral diseases
WO2011103441A1 (en)	2010-02-18	2011-08-25	Schering Corporation	Substituted pyridine and pyrimidine derivatives and their use in treating viral infections
EP2545060B1 (en)	2010-03-09	2015-11-25	Merck Sharp & Dohme Corp.	Fused tricyclic silyl compounds and methods of use thereof for the treatment of viral diseases
WO2011139253A2 (en)	2010-05-04	2011-11-10	Mahmut Bilgic	Pharmaceutical compositions comprising ceftibuten
AU2011286276A1 (en)	2010-07-26	2013-01-24	Merck Sharp & Dohme Corp.	Substituted biphenylene compounds and methods of use thereof for the treatment of viral diseases
JP2013540122A (ja)	2010-09-29	2013-10-31	メルク・シャープ・エンド・ドーム・コーポレイション	縮合四環式化合物誘導体およびウィルス疾患治療のためのそれの使用方法
BR112013026345A2 (pt)	2011-04-13	2019-04-24	Merck Sharp & Dohe Corp.	composto, composição farmacêutica, uso de um composto, e, método para tratar um paciente infectado com hcv
EP2697242B1 (en)	2011-04-13	2018-10-03	Merck Sharp & Dohme Corp.	2'-azido substituted nucleoside derivatives and methods of use thereof for the treatment of viral diseases
WO2013033899A1 (en)	2011-09-08	2013-03-14	Merck Sharp & Dohme Corp.	Substituted benzofuran compounds and methods of use thereof for the treatment of viral diseases
WO2013033901A1 (en)	2011-09-08	2013-03-14	Merck Sharp & Dohme Corp.	Heterocyclic-substituted benzofuran derivatives and methods of use thereof for the treatment of viral diseases
WO2013033900A1 (en)	2011-09-08	2013-03-14	Merck Sharp & Dohme Corp.	Tetracyclic heterocycle compounds and methods of use thereof for the treatment of viral diseases
EP2755981A4 (en)	2011-09-14	2015-03-25	Merck Sharp & Dohme	SILICULAR HETEROCYCLIC DERIVATIVES AND METHOD FOR THEIR USE FOR THE TREATMENT OF VIRUS DISEASES
WO2013151518A1 (en) *	2012-04-04	2013-10-10	Mahmut Bilgic	Capsule formulations comprising ceftibuten
EP2815743A1 (en)	2013-06-21	2014-12-24	Sanovel Ilac Sanayi ve Ticaret A.S.	Ceftibuten formulations
EP3063140A4 (en)	2013-10-30	2017-11-08	Merck Sharp & Dohme Corp.	Pseudopolymorphs of an hcv ns5a inhibitor and uses thereof
US9242965B2 (en)	2013-12-31	2016-01-26	Boehringer Ingelheim International Gmbh	Process for the manufacture of (E)-4-N,N-dialkylamino crotonic acid in HX salt form and use thereof for synthesis of EGFR tyrosine kinase inhibitors
CN103948932B (zh) *	2014-04-17	2016-03-16	海南日中天制药有限公司	一种头孢克肟组合物及其制备方法
EP3031450A1 (en)	2014-12-12	2016-06-15	Sanovel Ilac Sanayi ve Ticaret A.S.	Ceftibuten capsule compositions
US11117909B2 (en)	2016-05-13	2021-09-14	Aeromics, Inc.	Crystals
ES2894251T3 (es)	2016-06-30	2022-02-14	Qpex Biopharma Inc	Derivados de ácido borónico y usos terapéuticos de los mismos
CN106397454B (zh) *	2016-08-30	2018-08-24	山东罗欣药业集团股份有限公司	一种抗感染药物头孢布烯晶型化合物及其组合物
CN106432270A (zh) *	2016-09-21	2017-02-22	临沂草之美医药科技有限公司	一种制备治疗外科手术感染的药物头孢布烯晶体化合物的方法
CN106432272A (zh) *	2016-09-21	2017-02-22	临沂草之美医药科技有限公司	一种制备治疗外科手术感染的药物头孢布烯晶体化合物的方法
CN106432271A (zh) *	2016-09-21	2017-02-22	临沂草之美医药科技有限公司	一种治疗外科手术感染的药物头孢布烯晶体化合物
CN106397457A (zh) *	2016-09-21	2017-02-15	临沂草之美医药科技有限公司	一种治疗外科手术感染的药物头孢布烯晶体化合物
BR112022022367A2 (pt)	2020-05-05	2023-01-10	Qpex Biopharma Inc	Derivados e síntese de ácido borônico, formas polimórficas e usos terapêuticos dos mesmos
EP4362950A4 (en) *	2021-07-01	2025-08-13	Qpex Biopharma Inc	CRYSTALLINE FORMS OF CEFTIBUTEN

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3819620A (en) *	1972-06-01	1974-06-25	Squibb & Sons Inc	7-(d-alpha-amino-1,4-cyclohexadien-1-ylacet-amido)desacetoxycephalosporanic acid dihydrate
JPS5726692A (en) *	1980-07-22	1982-02-12	Fujisawa Pharmaceut Co Ltd	Preparation of stable crystal of salt of ceftizoxime
DE3037997A1 (de) *	1980-10-08	1982-05-13	Bayer Ag	(beta) -lactamantibiotika, verfahren zu deren herstellung sowie sie enthaltende mittel
YU44680B (en) *	1982-07-30	1990-12-31	Glaxo Lab Ltd	Process for obtaining very pure amorphous form of cephuroxim axetile
AU575854B2 (en) *	1983-10-04	1988-08-11	Shionogi & Co., Ltd.	7beta-(carboxyalkenamido) cephalosporins
AU580855B2 (en) *	1985-03-29	1989-02-02	Shionogi & Co., Ltd.	Alkeneamidocephalosporin esters

1987
- 1987-06-19 NZ NZ220764A patent/NZ220764A/xx unknown
- 1987-06-26 NL NL8701507A patent/NL193136C/nl not_active IP Right Cessation
- 1987-06-26 GB GB8715064A patent/GB2192183B/en not_active Expired - Lifetime
- 1987-06-29 IE IE173887A patent/IE59613B1/en not_active IP Right Cessation
- 1987-06-29 GR GR871014A patent/GR871014B/el unknown
- 1987-06-30 DK DK336487A patent/DK161080C/da not_active IP Right Cessation
- 1987-06-30 SE SE8702705A patent/SE466257B/sv not_active IP Right Cessation
- 1987-06-30 NO NO872729A patent/NO170889C/no not_active IP Right Cessation
- 1987-07-01 CH CH2482/87A patent/CH672788A5/de not_active IP Right Cessation
- 1987-07-01 FR FR878709316A patent/FR2601014B1/fr not_active Expired - Lifetime
- 1987-07-01 PL PL1987266567A patent/PL159180B1/pl unknown
- 1987-07-01 IT IT8767566A patent/IT1211469B/it active Protection Beyond IP Right Term
- 1987-07-01 FI FI872903A patent/FI89052C/fi not_active IP Right Cessation
- 1987-07-01 AT AT1658/87A patent/AT392472B/de not_active IP Right Cessation
- 1987-07-01 HU HU872992A patent/HU200777B/hu unknown
- 1987-07-01 US US07/068,333 patent/US4812561A/en not_active Expired - Lifetime
- 1987-07-01 IL IL83059A patent/IL83059A/xx not_active IP Right Cessation
- 1987-07-02 CA CA000541183A patent/CA1283405C/en not_active Expired - Lifetime
- 1987-07-02 ES ES8702189A patent/ES2004952A6/es not_active Expired
- 1987-07-02 KR KR1019870007019A patent/KR950005302B1/ko not_active Expired - Lifetime
- 1987-07-02 BE BE8700740A patent/BE1001691A4/fr not_active IP Right Cessation
- 1987-07-02 CN CN87105009A patent/CN1015106B/zh not_active Expired
- 1987-07-02 AR AR87308050A patent/AR243893A1/es active
- 1987-07-02 AU AU75040/87A patent/AU594167B2/en not_active Expired
- 1987-07-02 DE DE19873721913 patent/DE3721913A1/de not_active Withdrawn
- 1987-11-02 ES ES8703123A patent/ES2008759A6/es not_active Expired
- 1987-12-30 RU SU874203950A patent/RU1829932C/ru active
1988
- 1988-11-21 US US07/275,093 patent/US4933443A/en not_active Expired - Lifetime
1993
- 1993-05-20 HK HK478/93A patent/HK47893A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
IT1211469B (it)	1989-11-03
SE8702705L (sv)	1988-01-03
DK161080C (da)	1991-11-11
GR871014B (en)	1987-11-02
FR2601014B1 (fr)	1990-09-14
IE871738L (en)	1988-01-02
CN1015106B (zh)	1991-12-18
HK47893A (en)	1993-05-27
IE59613B1 (en)	1994-03-09
DK161080B (da)	1991-05-27
NO872729L (no)	1988-01-04
GB2192183B (en)	1990-05-16
ES2004952A6 (es)	1989-02-16
ES2008759A6 (es)	1989-08-01
DK336487D0 (da)	1987-06-30
FI89052B (fi)	1993-04-30
DE3721913A1 (de)	1988-01-07
AR243893A1 (es)	1993-09-30
SE466257B (sv)	1992-01-20
CH672788A5 (da)	1989-12-29
SE8702705D0 (sv)	1987-06-30
ATA165887A (de)	1990-09-15
KR950005302B1 (ko)	1995-05-23
BE1001691A4 (fr)	1990-02-13
IT8767566A0 (it)	1987-07-01
FR2601014A1 (fr)	1988-01-08
FI89052C (fi)	1993-08-10
GB2192183A (en)	1988-01-06
PL159180B1 (pl)	1992-11-30
IL83059A (en)	1992-03-29
US4812561A (en)	1989-03-14
GB8715064D0 (en)	1987-08-05
HUT44257A (en)	1988-02-29
CA1283405C (en)	1991-04-23
NO170889C (no)	1992-12-23
NL193136B (nl)	1998-08-03
AU594167B2 (en)	1990-03-01
AT392472B (de)	1991-04-10
CN87105009A (zh)	1988-03-23
NZ220764A (en)	1989-09-27
FI872903A0 (fi)	1987-07-01
NO872729D0 (no)	1987-06-30
PL266567A1 (en)	1988-07-21
AU7504087A (en)	1988-01-07
NO170889B (no)	1992-09-14
IL83059A0 (en)	1987-12-31
DK336487A (da)	1988-01-03
HU200777B (en)	1990-08-28
NL8701507A (nl)	1988-02-01
FI872903L (fi)	1988-01-03
KR880001670A (ko)	1988-04-26
RU1829932C (ru)	1993-07-23
US4933443A (en)	1990-06-12

Legal Events

Date	Code	Title	Description
1994-06-01	BA	A request for search or an international-type search has been filed
1994-07-01	BB	A search report has been drawn up
1994-08-01	BC	A request for examination has been filed
2007-09-03	V4	Discontinued because of reaching the maximum lifetime of a patent	Effective date: 20070626

Publication	Publication Date	Title
NL193136C (nl)	1998-12-04	Kristallijn hydraat van een oraal cefalosporine derivaat, werkwijze voor het bereiden daarvan en farmaceutisch product daaruit.
US5017380A (en)	1991-05-21	Gelatin hard capsule containing crystalline hydrate of oral cephalosporin
DE69222950T2 (de)	1998-05-28	Darmlösliche oral verabreichbare arzneimittel welche säurelabile verbindungen enthalten
SK155194A3 (en)	1997-01-08	Gastro-protected stable omeprazole composition in the form of microgranules and process for their production
LT4780B (lt)	2001-04-25	Živ proteazės inhibitoriaus rūgštusis sulfatas
US4337246A (en)	1982-06-29	Solid preparation comprising cobamamide or mecobalamin
ES2234051T3 (es)	2005-06-16	Composiciones farmaceuticas de cilansetron estabilizadas contra la racemizacion.
CA1235065A (en)	1988-04-12	Stabilized 4-carbamoyl-imidazolium-5-olate preparations
JPH03173822A (ja)	1991-07-29	セファロスポリン系薬物を含有する注射用組成物
JP3995414B2 (ja)	2007-10-24	安定な医薬組成物
SK279891B6 (sk)	1999-05-07	Inklúzny komplex n-etoxykarbonyl-3-morfolínosydnon
JP2544113B2 (ja)	1996-10-16	安定なカプセル製剤
US5077310A (en)	1991-12-31	Granulation product of calcium ascorbate
RS53324B (sr)	2014-10-31	Stabilna formulacija amorfnih soli perindoprila, postupak za njihovu pripremu, naročito industrijsku pripremu, i njihova upotreba u terapiji hipertenzije
CN110214030B (zh)	2023-09-19	具有高稳定性的含有羟丙基β环糊精的软明胶胶囊
US6060498A (en)	2000-05-09	Composition containing antitumor agent
KR920008161B1 (ko)	1992-09-24	오메프라졸 경구용 약제의 제조방법
DE3745094B4 (de)	2004-12-30	Ein kristallines Hydrat der 7ß-[(Z)-2-(2-Aminothiazol-4-yl)-4-carboxybut-2-enoylamino]-3-cephem-4-carbonsäure enthaltende Hartgelatinekapsel-Zusammensetzung
AU754138B2 (en)	2002-11-07	Quinolinone derivative preparations and process for producing the same
AT396652B (de)	1993-11-25	Verfahren zur herstellung von hartgelatinekapsel-zusammensetzungen
FI95349C (fi)	1996-01-25	Menetelmä 7 -/(Z)-2-(2-aminotiatsol-4-yyli)-4-karboksibut-2-enoyyliamino/-3-kefeemi-4-karboksyylihappoa sisältävän gelatiinikapselin valmistamiseksi
KR840001002B1 (ko)	1984-07-19	코밤아미드나 메코발아민을 함유하는 고체제제의 제조방법
KR960004018B1 (ko)	1996-03-25	L-글루타민과 수용성아줄렌 복합 항궤양용 제제의 안정화 방법
HU210527A9 (hu)	1995-04-28	Cefalosporin kristályos hidrátja orális alkalmazáshoz és az ezt tartalmazó készítmény Az átmeneti oltalom az 1-4. és 15-17. igénypontokra vonatkozik.
CA2254411A1 (en)	1999-01-18	Ticlopidine hcl formulations