IL45548A - 3,3'-methylene-bis-(4-hydroxy-5-azacoumarin) its preparation and pharmaceutical compositions containing it - Google Patents

3,3'-methylene-bis-(4-hydroxy-5-azacoumarin) its preparation and pharmaceutical compositions containing it

Info

Publication number: IL45548A
Authority: IL; Israel
Prior art keywords: acid; hydroxy; azacoumarin; process according; formula
Prior art date: 1973-09-10

Application number

IL45548A

Other languages

English (en)

Other versions

IL45548A0 (en

Original Assignee

Christiaens Sa A

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.)

1973-09-10

Filing date

1974-08-27

Publication date

1977-12-30

1974-08-27 Application filed by Christiaens Sa A filed Critical Christiaens Sa A

1974-11-29 Publication of IL45548A0 publication Critical patent/IL45548A0/xx

1977-12-30 Publication of IL45548A publication Critical patent/IL45548A/en

Links

238000002360 preparation method Methods 0.000 title abstract description 11
UWQCORYIDSZDLB-UHFFFAOYSA-N 4-hydroxy-3-[(4-hydroxy-2-oxopyrano[3,2-b]pyridin-3-yl)methyl]pyrano[3,2-b]pyridin-2-one Chemical compound C1=CC=NC2=C1OC(=O)C(CC=1C(OC3=CC=CN=C3C=1O)=O)=C2O UWQCORYIDSZDLB-UHFFFAOYSA-N 0.000 title abstract description 5
239000008194 pharmaceutical composition Substances 0.000 title description 2
HHSOESOBCICGMY-UHFFFAOYSA-N 4-hydroxypyrano[3,2-b]pyridin-2-one Chemical compound C1=CC=NC2=C1OC(=O)C=C2O HHSOESOBCICGMY-UHFFFAOYSA-N 0.000 claims description 16
150000001875 compounds Chemical class 0.000 claims description 16
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
238000000034 method Methods 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 11
BRARRAHGNDUELT-UHFFFAOYSA-N 3-hydroxypicolinic acid Chemical compound OC(=O)C1=NC=CC=C1O BRARRAHGNDUELT-UHFFFAOYSA-N 0.000 claims description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 6
229920000137 polyphosphoric acid Polymers 0.000 claims description 6
BAEQXHMFUMCVBA-UHFFFAOYSA-N 2-(3-hydroxypyridine-2-carbonyl)propanedioic acid Chemical compound OC=1C(=NC=CC1)C(=O)C(C(=O)O)C(=O)O BAEQXHMFUMCVBA-UHFFFAOYSA-N 0.000 claims description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
230000003569 amebicidal effect Effects 0.000 claims description 5
229910052751 metal Inorganic materials 0.000 claims description 5
239000002184 metal Substances 0.000 claims description 5
238000001953 recrystallisation Methods 0.000 claims description 5
238000007363 ring formation reaction Methods 0.000 claims description 5
MYBURCWUYXAEAE-UHFFFAOYSA-N CCO[Mg]CC.OC(=O)CC(O)=O Chemical compound CCO[Mg]CC.OC(=O)CC(O)=O MYBURCWUYXAEAE-UHFFFAOYSA-N 0.000 claims description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
239000002798 polar solvent Substances 0.000 claims description 4
229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
238000009833 condensation Methods 0.000 claims description 3
230000005494 condensation Effects 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
-1 ethyl 3-hydroxypicolinoyl-cyanoacetate Chemical compound 0.000 claims description 3
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 2
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical class CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 claims description 2
BYCZNPXIDDRNEQ-UHFFFAOYSA-N ethyl 4-hydroxy-2-oxopyrano[3,2-b]pyridine-3-carboxylate Chemical compound OC1=C(C(OC2=CC=CN=C12)=O)C(=O)OCC BYCZNPXIDDRNEQ-UHFFFAOYSA-N 0.000 claims description 2
XQWZELKOTXALGK-UHFFFAOYSA-N 2-hydroxy-2-(pyridine-2-carbonyl)propanedioic acid Chemical compound OC(C(=O)O)(C(=O)O)C(C1=NC=CC=C1)=O XQWZELKOTXALGK-UHFFFAOYSA-N 0.000 claims 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Substances CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
229910052700 potassium Inorganic materials 0.000 claims 1
239000011591 potassium Substances 0.000 claims 1
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
239000000243 solution Substances 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
239000000047 product Substances 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000011282 treatment Methods 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
DYFSAZGSIBFUAI-UHFFFAOYSA-N 1-(3-hydroxypyridin-2-yl)ethanone Chemical compound CC(=O)C1=NC=CC=C1O DYFSAZGSIBFUAI-UHFFFAOYSA-N 0.000 description 5
229960003606 phanquinone Drugs 0.000 description 5
VLPADTBFADIFKG-UHFFFAOYSA-N phanquone Chemical compound C1=CN=C2C(=O)C(=O)C3=NC=CC=C3C2=C1 VLPADTBFADIFKG-UHFFFAOYSA-N 0.000 description 5
238000003756 stirring Methods 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000001963 growth medium Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000000155 melt Substances 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
241000224432 Entamoeba histolytica Species 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000002775 capsule Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
229940007078 entamoeba histolytica Drugs 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
239000006187 pill Substances 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
BIXMBBKKPTYJEK-UHFFFAOYSA-N 1,3-benzoxazin-2-one Chemical compound C1=CC=C2OC(=O)N=CC2=C1 BIXMBBKKPTYJEK-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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 2
206010030113 Oedema Diseases 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
208000025865 Ulcer Diseases 0.000 description 2
230000009102 absorption Effects 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
244000052637 human pathogen Species 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
239000008101 lactose Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
239000002609 medium Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 2
210000003097 mucus Anatomy 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
229920001592 potato starch Polymers 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
230000036269 ulceration Effects 0.000 description 2
244000215068 Acacia senegal Species 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
241000252983 Caecum Species 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
HGINADPHJQTSKN-UHFFFAOYSA-N Monoethyl malonic acid Chemical class CCOC(=O)CC(O)=O HGINADPHJQTSKN-UHFFFAOYSA-N 0.000 description 1
241000786363 Rhampholeon spectrum Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229940124323 amoebicide Drugs 0.000 description 1
239000000059 antiamebic agent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000004203 carnauba wax Substances 0.000 description 1
210000004534 cecum Anatomy 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
OIQPTROHQCGFEF-UHFFFAOYSA-L chembl1371409 Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 OIQPTROHQCGFEF-UHFFFAOYSA-L 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
229940080428 lactose 200 mg Drugs 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000002639 sodium chloride Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
235000012751 sunset yellow FCF Nutrition 0.000 description 1
239000004173 sunset yellow FCF Substances 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

IL45548A 1973-09-10 1974-08-27 3,3'-methylene-bis-(4-hydroxy-5-azacoumarin) its preparation and pharmaceutical compositions containing it IL45548A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB4249673A GB1472257A (en)	1973-09-10	1973-09-10	Derivative of 4-hydroxy-5-azacoumarin

Publications (2)

Publication Number	Publication Date
IL45548A0 IL45548A0 (en)	1974-11-29
IL45548A true IL45548A (en)	1977-12-30

Family

ID=10424693

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL45548A IL45548A (en)	1973-09-10	1974-08-27	3,3'-methylene-bis-(4-hydroxy-5-azacoumarin) its preparation and pharmaceutical compositions containing it

Country Status (12)

Country	Link
US (1)	US3919248A (ja)
JP (1)	JPS5076094A (ja)
BE (1)	BE819570A (ja)
CA (1)	CA1033741A (ja)
CH (1)	CH596213A5 (ja)
DE (1)	DE2442666A1 (ja)
FR (1)	FR2242981B1 (ja)
GB (1)	GB1472257A (ja)
HU (1)	HU169668B (ja)
IL (1)	IL45548A (ja)
NL (1)	NL7412022A (ja)
ZA (1)	ZA745608B (ja)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1999009981A1 (en) *	1997-08-21	1999-03-04	P.N. Gerolymatos S.A.	Use of phanquinone for the treatment of alzheimer's disease
DK1140090T3 (da)	1999-01-07	2005-04-18	Gerolymatos P N Sa	Anvendelse af phanquinon til behandlingen eller hindringen af hukommelsessvigt
PL3303330T3 (pl)	2015-06-03	2019-10-31	Bristol Myers Squibb Co	Agoniści 4 - hydroksy - 3 - ( heteroarylo ) pirydyno - 2 - onowi receptora apj do stosowania w leczeniu zaburzeń sercowo-naczyniowych

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3689493A (en) *	1970-03-17	1972-09-05	Fisons Pharmaceuticals Ltd	5-,6-and 7-azachromones

1973
- 1973-09-10 GB GB4249673A patent/GB1472257A/en not_active Expired
1974
- 1974-08-27 IL IL45548A patent/IL45548A/en unknown
- 1974-08-28 CA CA208,014A patent/CA1033741A/en not_active Expired
- 1974-09-03 ZA ZA00745608A patent/ZA745608B/xx unknown
- 1974-09-05 BE BE148226A patent/BE819570A/xx unknown
- 1974-09-06 DE DE2442666A patent/DE2442666A1/de not_active Withdrawn
- 1974-09-09 CH CH1223574A patent/CH596213A5/xx not_active IP Right Cessation
- 1974-09-09 FR FR7430512A patent/FR2242981B1/fr not_active Expired
- 1974-09-09 HU HUCI1506A patent/HU169668B/hu unknown
- 1974-09-10 JP JP49104792A patent/JPS5076094A/ja active Pending
- 1974-09-10 US US504787A patent/US3919248A/en not_active Expired - Lifetime
- 1974-09-10 NL NL7412022A patent/NL7412022A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
JPS5076094A (ja)	1975-06-21
BE819570A (fr)	1975-03-05
IL45548A0 (en)	1974-11-29
FR2242981A1 (ja)	1975-04-04
NL7412022A (nl)	1975-03-12
DE2442666A1 (de)	1975-03-20
AU7286774A (en)	1976-03-04
ZA745608B (en)	1975-10-29
HU169668B (ja)	1977-02-28
CH596213A5 (ja)	1978-03-15
CA1033741A (en)	1978-06-27
US3919248A (en)	1975-11-11
FR2242981B1 (ja)	1978-11-10
GB1472257A (en)	1977-05-04

Publication	Publication Date	Title
DE2628045A1 (de)	1977-01-20	Thieno(2,3-c)pyridinderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
HU230216B1 (hu)	2015-10-28	Eljárás alkoholok és fenolok vízoldható foszfonooximetil-származékai előállítására
NO137440B (no)	1977-11-21	Analogifremgangsm}te for fremstilling av terapeutisk aktive pleuromutiliner
DE2637110B2 (de)	1979-10-11	Heteroarylbenzoxepin-essigsäuren und deren Ester, Verfahren zu ihrer Herstellung und deren Verwendung
DE2736784A1 (de)	1978-03-02	N-substituierte und nichtsubstituierte hexahydro-6-canthinonderivate, verfahren zum herstellen derselben und diese derivate enthaltende pharmazeutische zusammensetzung
DK154287B (da)	1988-10-31	Analogifremgangsmaade til fremstilling af triglycerider
DK171789B1 (da)	1997-05-26	4-Thiazolidincarboxylsyrederivat, dets fremstilli ng og lægemidler, der indeholder det
DE2010180A1 (de)	1970-10-08	Neue 2,4,6-Trihydroxychalkonderivate
AT391689B (de)	1990-11-12	Verfahren zur herstellung von neuen 4-phenyl-4-oxo-2-butensaeurederivaten und von deren salzen
IL45548A (en)	1977-12-30	3,3'-methylene-bis-(4-hydroxy-5-azacoumarin) its preparation and pharmaceutical compositions containing it
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DE2449205A1 (de)	1975-04-24	Diaromatische o-(aminoalkyl)-oxime, verfahren zu ihrer herstellung und sie enthaltende arzneimittelzubereitungen
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