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

NL8701507A (nl

NL193136B (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 (no)
KR (1)	KR950005302B1 (no)
CN (1)	CN1015106B (no)
AR (1)	AR243893A1 (no)
AT (1)	AT392472B (no)
AU (1)	AU594167B2 (no)
BE (1)	BE1001691A4 (no)
CA (1)	CA1283405C (no)
CH (1)	CH672788A5 (no)
DE (1)	DE3721913A1 (no)
DK (1)	DK161080C (no)
ES (2)	ES2004952A6 (no)
FI (1)	FI89052C (no)
FR (1)	FR2601014B1 (no)
GB (1)	GB2192183B (no)
GR (1)	GR871014B (no)
HK (1)	HK47893A (no)
HU (1)	HU200777B (no)
IE (1)	IE59613B1 (no)
IL (1)	IL83059A (no)
IT (1)	IT1211469B (no)
NL (1)	NL193136C (no)
NO (1)	NO170889C (no)
NZ (1)	NZ220764A (no)
PL (1)	PL159180B1 (no)
RU (1)	RU1829932C (no)
SE (1)	SE466257B (no)

Families Citing this family (67)

* 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
NZ252433A (en) *	1992-04-30	1996-07-26	Schering Corp	Preparation of a dry hydrated cephalosporin powder formulation which is resistant to air oxidation and dehydration by mixing the drug with dry excipients and filling into a sealable storage container
ATE544789T1 (de) *	1998-10-27	2012-02-15	Westlake Longview Corp	Verfahren zur olefinpolymerisation, neue polyethylene und daraus hergestellte folien und artikel
US6544555B2 (en) *	2000-02-24	2003-04-08	Advancis Pharmaceutical Corp.	Antibiotic product, use and formulation thereof
US6565882B2 (en) *	2000-02-24	2003-05-20	Advancis Pharmaceutical Corp	Antibiotic composition with inhibitor
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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 SE SE8702705A patent/SE466257B/sv not_active IP Right Cessation
- 1987-06-30 DK DK336487A patent/DK161080C/da not_active IP Right Cessation
- 1987-06-30 NO NO872729A patent/NO170889C/no 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 CH CH2482/87A patent/CH672788A5/de not_active IP Right Cessation
- 1987-07-01 US US07/068,333 patent/US4812561A/en not_active Expired - Lifetime
- 1987-07-01 FI FI872903A patent/FI89052C/fi not_active IP Right Cessation
- 1987-07-01 FR FR878709316A patent/FR2601014B1/fr not_active Expired - Lifetime
- 1987-07-01 IT IT8767566A patent/IT1211469B/it active Protection Beyond IP Right Term
- 1987-07-01 IL IL83059A patent/IL83059A/xx not_active IP Right Cessation
- 1987-07-01 PL PL1987266567A patent/PL159180B1/pl unknown
- 1987-07-02 AR AR87308050A patent/AR243893A1/es active
- 1987-07-02 CA CA000541183A patent/CA1283405C/en not_active Expired - Lifetime
- 1987-07-02 AU AU75040/87A patent/AU594167B2/en not_active Expired
- 1987-07-02 DE DE19873721913 patent/DE3721913A1/de not_active Withdrawn
- 1987-07-02 CN CN87105009A patent/CN1015106B/zh 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 ES ES8702189A patent/ES2004952A6/es not_active Expired
- 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
NO170889C (no)	1992-12-23
KR880001670A (ko)	1988-04-26
SE8702705D0 (sv)	1987-06-30
PL266567A1 (en)	1988-07-21
NO872729L (no)	1988-01-04
RU1829932C (ru)	1993-07-23
IT1211469B (it)	1989-11-03
GR871014B (en)	1987-11-02
IE871738L (en)	1988-01-02
CH672788A5 (no)	1989-12-29
GB2192183A (en)	1988-01-06
IL83059A0 (en)	1987-12-31
ES2004952A6 (es)	1989-02-16
IT8767566A0 (it)	1987-07-01
NO170889B (no)	1992-09-14
NL8701507A (nl)	1988-02-01
SE8702705L (sv)	1988-01-03
IL83059A (en)	1992-03-29
IE59613B1 (en)	1994-03-09
FI872903A0 (fi)	1987-07-01
KR950005302B1 (ko)	1995-05-23
AU7504087A (en)	1988-01-07
FR2601014A1 (fr)	1988-01-08
HU200777B (en)	1990-08-28
DK161080B (da)	1991-05-27
NL193136B (nl)	1998-08-03
US4933443A (en)	1990-06-12
ES2008759A6 (es)	1989-08-01
AR243893A1 (es)	1993-09-30
US4812561A (en)	1989-03-14
CN87105009A (zh)	1988-03-23
AU594167B2 (en)	1990-03-01
DK336487A (da)	1988-01-03
DK161080C (da)	1991-11-11
GB8715064D0 (en)	1987-08-05
AT392472B (de)	1991-04-10
HK47893A (en)	1993-05-27
NZ220764A (en)	1989-09-27
NO872729D0 (no)	1987-06-30
FI89052C (fi)	1993-08-10
BE1001691A4 (fr)	1990-02-13
ATA165887A (de)	1990-09-15
DK336487D0 (da)	1987-06-30
GB2192183B (en)	1990-05-16
DE3721913A1 (de)	1988-01-07
FI89052B (fi)	1993-04-30
PL159180B1 (pl)	1992-11-30
CN1015106B (zh)	1991-12-18
SE466257B (sv)	1992-01-20
HUT44257A (en)	1988-02-29
FI872903L (fi)	1988-01-03
FR2601014B1 (fr)	1990-09-14
CA1283405C (en)	1991-04-23

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.
JPH0137376B2 (no)	1989-08-07
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

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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