DD292259A5 - Verfahren zur herstellung von [3-(c[ind16]-c[ind18]alkansulfinyl- und sulfonyl-2-methoxymethyl-propyl]-(2-trimethylammonio-ethyl) phosphate - Google Patents

Verfahren zur herstellung von [3-(c[ind16]-c[ind18]alkansulfinyl- und sulfonyl-2-methoxymethyl-propyl]-(2-trimethylammonio-ethyl) phosphate Download PDF

Info

Publication number: DD292259A5
Authority: DD; German Democratic Republic
Prior art keywords: general formula; phosphate; propyl; trimethylammonio; compound
Prior art date: 1989-03-04

Application number

DD90338238A

Other languages

German (de)

English (en)

Inventor

Elmar Bosies

Dieter Herrmann

Wulf Pahlke

Original Assignee

��@��@��k��

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.)

1989-03-04

Filing date

1990-02-28

Publication date

1991-07-25

1990-02-28 Application filed by ��@��@��k�� filed Critical ��@��@��k��

1991-07-25 Publication of DD292259A5 publication Critical patent/DD292259A5/de

Links

238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 26
238000000034 method Methods 0.000 claims abstract description 16
150000003839 salts Chemical class 0.000 claims abstract description 10
238000002360 preparation method Methods 0.000 claims abstract description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 4
239000007800 oxidant agent Substances 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
238000005576 amination reaction Methods 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
239000011230 binding agent Substances 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical group ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
-1 sulphonyl-2-methoxymethylpropyl (2-trimethylammonioethyl)phosphates Chemical class 0.000 abstract description 21
230000000259 anti-tumor effect Effects 0.000 abstract description 3
239000003814 drug Substances 0.000 abstract description 2
229910019142 PO4 Inorganic materials 0.000 description 17
239000010452 phosphate Substances 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 7
150000003568 thioethers Chemical class 0.000 description 7
235000021317 phosphate Nutrition 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
206010028980 Neoplasm Diseases 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
ODEDPKNSRBCSDO-UHFFFAOYSA-N [2-(hexadecylsulfanylmethyl)-3-methoxypropyl] 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCCSCC(COC)COP([O-])(=O)OCC[N+](C)(C)C ODEDPKNSRBCSDO-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 description 2
YPGCWEMNNLXISK-UHFFFAOYSA-N alpha-phenylpropionic acid Natural products OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000000969 carrier Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
229920006158 high molecular weight polymer Polymers 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
229950006905 ilmofosine Drugs 0.000 description 2
238000001727 in vivo 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
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
150000003457 sulfones Chemical class 0.000 description 2
150000003462 sulfoxides Chemical class 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
LSPHULWDVZXLIL-PHUNFMHTSA-N (1s)-1,2,2-trimethylcyclopentane-1,3-dicarboxylic acid Chemical compound CC1(C)C(C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-PHUNFMHTSA-N 0.000 description 1
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
YPGCWEMNNLXISK-ZETCQYMHSA-N (S)-hydratropic acid Chemical compound OC(=O)[C@@H](C)C1=CC=CC=C1 YPGCWEMNNLXISK-ZETCQYMHSA-N 0.000 description 1
YHHSONZFOIEMCP-UHFFFAOYSA-N 2-(trimethylazaniumyl)ethyl hydrogen phosphate Chemical compound C[N+](C)(C)CCOP(O)([O-])=O YHHSONZFOIEMCP-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
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
QXEQVPDRSQYMPV-UHFFFAOYSA-N CCCCCCCCCCCCCCCCCCS(CC(CC(COP([O-])(O)=O)[N+](C)(C)C)COC)(=O)=O Chemical compound CCCCCCCCCCCCCCCCCCS(CC(CC(COP([O-])(O)=O)[N+](C)(C)C)COC)(=O)=O QXEQVPDRSQYMPV-UHFFFAOYSA-N 0.000 description 1
SZQZSQFHECBPSV-UHFFFAOYSA-N CCCCCCCCCCCCCCCCS(CC(CC(COP([O-])(O)=O)[N+](C)(C)C)COC)(=O)=O Chemical compound CCCCCCCCCCCCCCCCS(CC(CC(COP([O-])(O)=O)[N+](C)(C)C)COC)(=O)=O SZQZSQFHECBPSV-UHFFFAOYSA-N 0.000 description 1
CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 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
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
201000008808 Fibrosarcoma Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
241000206672 Gelidium Species 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
229930195725 Mannitol Natural products 0.000 description 1
PPQNQXQZIWHJRB-UHFFFAOYSA-N Methylcholanthrene Chemical compound C1=CC=C2C3=CC4=CC=C(C)C(CC5)=C4C5=C3C=CC2=C1 PPQNQXQZIWHJRB-UHFFFAOYSA-N 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000007979 citrate buffer Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000008139 complexing agent Substances 0.000 description 1
229960004397 cyclophosphamide Drugs 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
150000002689 maleic acids Chemical class 0.000 description 1
150000002691 malonic acids Chemical class 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
MDLWEBWGXACWGE-UHFFFAOYSA-N octadecane Chemical compound [CH2]CCCCCCCCCCCCCCCCC MDLWEBWGXACWGE-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
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000013641 positive control Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003870 salicylic acids Chemical class 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000002904 solvent Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000003381 stabilizer Substances 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
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000003756 stirring Methods 0.000 description 1
235000011044 succinic acid Nutrition 0.000 description 1
150000003444 succinic acids Chemical class 0.000 description 1
125000003375 sulfoxide group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)

DD90338238A 1989-03-04 1990-02-28 Verfahren zur herstellung von [3-(c[ind16]-c[ind18]alkansulfinyl- und sulfonyl-2-methoxymethyl-propyl]-(2-trimethylammonio-ethyl) phosphate DD292259A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3906952A DE3906952A1 (de)	1989-03-04	1989-03-04	(3-(c(pfeil abwaerts)1(pfeil abwaerts)(pfeil abwaerts)6(pfeil abwaerts)-c(pfeil abwaerts)1(pfeil abwaerts)(pfeil abwaerts)8(pfeil abwaerts))alkansulfinyl- und sulfonyl-2-methoxymethyl-propyl)-(2-trimethylammonio-ethyl) phosphate, verfahren zu deren herstellung diese verbindungen enthaltende arzneimittel

Publications (1)

Publication Number	Publication Date
DD292259A5 true DD292259A5 (de)	1991-07-25

Family

ID=6375519

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90338238A DD292259A5 (de)	1989-03-04	1990-02-28	Verfahren zur herstellung von [3-(c[ind16]-c[ind18]alkansulfinyl- und sulfonyl-2-methoxymethyl-propyl]-(2-trimethylammonio-ethyl) phosphate

Country Status (19)

Country	Link
US (1)	US5543402A (ja)
EP (1)	EP0395849B1 (ja)
JP (1)	JPH0341027A (ja)
KR (1)	KR900014412A (ja)
AT (1)	ATE121409T1 (ja)
AU (1)	AU633304B2 (ja)
CA (1)	CA2011209A1 (ja)
DD (1)	DD292259A5 (ja)
DE (2)	DE3906952A1 (ja)
FI (1)	FI93122C (ja)
HU (1)	HU204057B (ja)
IE (1)	IE900743L (ja)
IL (1)	IL93598A (ja)
MX (1)	MX19722A (ja)
NO (1)	NO901008L (ja)
NZ (1)	NZ232692A (ja)
PT (1)	PT93324B (ja)
RU (1)	RU2035466C1 (ja)
ZA (1)	ZA901601B (ja)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3929217A1 (de) *	1989-09-02	1991-03-07	Boehringer Mannheim Gmbh	Verwendung von phospholipid-derivaten als antivirale arzneimittel und neue phospholipide
GB8928580D0 (en) *	1989-12-19	1990-02-21	Scras	3-(n-methyl-n-alkylamino)-methoxymethyl-propanol phosphocholine derivatives
DE4222910A1 (de) *	1992-07-11	1994-01-13	Asta Medica Ag	Neue Phospholipidderivate
US6172050B1 (en)	1992-07-11	2001-01-09	Asta Medica Aktiengesellschaft	Phospholipid derivatives
WO1994002153A1 (en) *	1992-07-22	1994-02-03	Boehringer Mannheim Gmbh	Use of sulphur containing phospholipids for treating leishmaniasis
CN100553636C (zh)	2000-08-04	2009-10-28	Dmi生物科学公司	二酮基哌嗪和包含它们的组合物的使用方法
KR100469556B1 (ko) *	2001-11-17	2005-02-02	주식회사 건축사사무소다인그룹	도어 잠금장치
CN1615314A (zh) *	2001-11-21	2005-05-11	海德堡医药有限责任公司	用作抗肿瘤药的核苷的磷脂衍生物
WO2004030522A2 (en) *	2002-10-02	2004-04-15	Dmi Biosciences, Inc.	Diagnosis and monitoring of diseases
EP2517718B1 (en)	2003-05-15	2016-03-02	Ampio Pharmaceuticals, Inc.	Treatment of T-cell mediated diseases
JP5856843B2 (ja)	2008-05-27	2016-02-10	アンピオファーマシューティカルズ，インコーポレイテッド	ジケトピペラジンを用いた医薬組成物
EP2613786A4 (en)	2010-09-07	2013-10-23	Dmi Acquisition Corp	TREATMENT OF DISEASES
MY172699A (en)	2011-10-10	2019-12-10	Ampio Pharmaceuticals Inc	Implantable medical devices with increased immune tolerance, and methods for making and implanting
EA028343B1 (ru)	2011-10-10	2017-11-30	Ампио Фармасьютикалз, Инк.	Лечение дегенеративного заболевания сустава
EP2771007B1 (en)	2011-10-28	2018-04-04	Ampio Pharmaceuticals, Inc.	Treatment of rhinitis
BR112015020469A2 (pt)	2013-03-15	2020-01-28	Ampio Pharmaceuticals Inc	Usos de da-dkp, composição e método para fornecimento de células-tronco a umindivíduo
RU2736513C2 (ru)	2014-08-18	2020-11-17	Ампио Фармасьютикалз, Инк.	Лечение патологических состояний суставов
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1989
- 1989-03-04 DE DE3906952A patent/DE3906952A1/de not_active Withdrawn
1990
- 1990-02-26 EP EP90103661A patent/EP0395849B1/de not_active Expired - Lifetime
- 1990-02-26 AT AT90103661T patent/ATE121409T1/de not_active IP Right Cessation
- 1990-02-26 DE DE59008915T patent/DE59008915D1/de not_active Expired - Fee Related
- 1990-02-27 NZ NZ232692A patent/NZ232692A/en unknown
- 1990-02-28 DD DD90338238A patent/DD292259A5/de not_active IP Right Cessation
- 1990-02-28 AU AU50596/90A patent/AU633304B2/en not_active Ceased
- 1990-03-01 IL IL9359890A patent/IL93598A/en not_active IP Right Cessation
- 1990-03-01 MX MX1972290A patent/MX19722A/es unknown
- 1990-03-02 IE IE900743A patent/IE900743L/xx unknown
- 1990-03-02 FI FI901096A patent/FI93122C/fi not_active IP Right Cessation
- 1990-03-02 HU HU901280A patent/HU204057B/hu not_active IP Right Cessation
- 1990-03-02 PT PT93324A patent/PT93324B/pt not_active IP Right Cessation
- 1990-03-02 NO NO90901008A patent/NO901008L/no unknown
- 1990-03-02 RU SU904743486A patent/RU2035466C1/ru active
- 1990-03-02 JP JP2051584A patent/JPH0341027A/ja active Pending
- 1990-03-02 ZA ZA901601A patent/ZA901601B/xx unknown
- 1990-03-05 CA CA002011209A patent/CA2011209A1/en not_active Abandoned
- 1990-03-05 KR KR1019900002942A patent/KR900014412A/ko not_active Withdrawn
1993
- 1993-07-23 US US08/095,478 patent/US5543402A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
NO901008L (no)	1990-09-05
US5543402A (en)	1996-08-06
PT93324B (pt)	1996-02-29
EP0395849B1 (de)	1995-04-19
NZ232692A (en)	1992-06-25
FI93122B (fi)	1994-11-15
ZA901601B (en)	1990-12-28
AU633304B2 (en)	1993-01-28
HUT53111A (en)	1990-09-28
JPH0341027A (ja)	1991-02-21
FI901096A0 (fi)	1990-03-02
DE59008915D1 (de)	1995-05-24
RU2035466C1 (ru)	1995-05-20
MX19722A (es)	1993-11-01
IL93598A0 (en)	1990-12-23
KR900014412A (ko)	1990-10-23
HU901280D0 (en)	1990-05-28
FI93122C (fi)	1995-02-27
EP0395849A1 (de)	1990-11-07
AU5059690A (en)	1990-09-06
PT93324A (pt)	1990-11-07
HU204057B (en)	1991-11-28
IL93598A (en)	1994-06-24
DE3906952A1 (de)	1990-09-06
CA2011209A1 (en)	1990-09-04
NO901008D0 (no)	1990-03-02
IE900743L (en)	1990-09-04
ATE121409T1 (de)	1995-05-15

Legal Events

Date	Code	Title	Description
1995-07-20	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0395849B1 (de)	1995-04-19	/3-(C16-C18)alkansulfinyl- und sulfonyl-2-methoxymethyl-propyl/-(2-trimethylammonio-ethyl)phosphate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
EP0050327B1 (de)	1984-06-20	Neue schwefelhaltige Phospholipide, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
EP0069968B1 (de)	1985-11-21	Phospholipide, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2355540C2 (de)	1982-11-18	16-Phenoxy-&omega;-tetranorprostaglandinderivate
EP0036583B1 (de)	1984-07-18	Glycerin-3-phosphorsäurehalogenalkylester und Verfahren zu ihrer Herstellung und Weiterverarbeitung
DE2221912A1 (de)	1972-11-16	Penicillinester,deren Salze und Verfahren zu ihrer Herstellung
EP0163888A1 (de)	1985-12-11	Amidinohydrazone von Tetralin-, Chromon-, Thiochromon- und Tetrahydrochinolin-Derivaten, Verfahren zu ihrer Herstellung sowie ihre Verwendung in Arzneimitteln
DE2926847C2 (ja)	1988-11-10
EP0112872A1 (de)	1984-07-11	Neue glycerinderivate zur synthese von phospholipiden
DD297561A5 (de)	1992-01-16	Verwendung von phospholipid-derivaten als antivirale arzneimittel und neue phospholipide
DE2626888A1 (de)	1977-04-07	11-desoxy-16-aryloxy-omega-tetranorprostaglandine
DE2745598A1 (de)	1978-04-20	Arylschwefelverbindungen, verfahren zu ihrer herstellung und sie enthaltendes pharmazeutisches mittel
DE4030587C2 (de)	1999-06-17	Verfahren zur Herstellung von D-Myoinosit-1-phosphat
CH508630A (de)	1971-06-15	Verfahren zur Herstellung neuer 5-Nitroimidazole
DE2359955C2 (de)	1982-12-30	2-(6-Carboxyhexyl)-3-alkylthio-Cyclopentanon-Derivate und diese enthaltende pharmazeutische Zubereitung
DE3204735A1 (de)	1983-08-18	Neue phospholipide, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel
CH512500A (de)	1971-09-15	Verfahren zur Herstellung von Phenazin-Derivaten
DE3024304C2 (ja)	1991-10-31
DE2711738C3 (ja)	1979-12-06
DE69513318T2 (de)	2000-04-13	Herstellung von Kristallen aus Diester Phosphat Monokazium-Salz
DE1004194B (de)	1957-03-14	Verfahren zur Herstellung von einheitlichen, hautvertraeglichen tertiaeren N-(ª‰,ª†-Dioxypropyl)-aminen
DE2060551A1 (de)	1972-06-22	Neue aliphatische difunktionelle stickstoffhaltige Sulfonsaeureester,ein Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
DE1151794B (de)	1963-07-25	Verfahren zur Herstellung des Mononatriumsalzes der Phospho-enolbrenztraubensaeure
DE2229225A1 (de)	1972-12-21	Derivate von 10 Oxaprostansaure und Verfahren zu ihrer Herstellung
AT394195B (de)	1992-02-10	Verfahren zur herstellung einer neuen cephalosporinverbindung