IL29189A - Esters of 3-(5'-nitro-2'-furyl)-5-alkylisoxazole-4-carboxylic acids - Google Patents

Esters of 3-(5'-nitro-2'-furyl)-5-alkylisoxazole-4-carboxylic acids

Info

Publication number: IL29189A
Authority: IL; Israel
Prior art keywords: nitro; furyl; methyl; acetone; isoxazol
Prior art date: 1966-12-28

Application number

IL29189A

Other languages

English (en)

Original Assignee

R & L Molecular Research Ltd

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.)

1966-12-28

Filing date

1967-12-21

Publication date

1972-06-28

1967-12-21 Application filed by R & L Molecular Research Ltd filed Critical R & L Molecular Research Ltd

1972-06-28 Publication of IL29189A publication Critical patent/IL29189A/en

Links

150000002148 esters Chemical class 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 15
238000000034 method Methods 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 7
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004043 oxo group Chemical group O=* 0.000 claims description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 61
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 48
239000000243 solution Substances 0.000 description 24
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
239000000203 mixture Substances 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
229910052943 magnesium sulfate Inorganic materials 0.000 description 11
235000019341 magnesium sulphate Nutrition 0.000 description 11
238000001228 spectrum Methods 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
LYPXTDXYEQEIIN-UHFFFAOYSA-N 1,2-oxazole-4-carboxylic acid Chemical compound OC(=O)C=1C=NOC=1 LYPXTDXYEQEIIN-UHFFFAOYSA-N 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 9
239000007787 solid Substances 0.000 description 9
MNANGXNDRCOVLE-UHFFFAOYSA-N 1,2-oxazole-4-carbonyl chloride Chemical compound ClC(=O)C=1C=NOC=1 MNANGXNDRCOVLE-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 7
238000001816 cooling Methods 0.000 description 6
239000013078 crystal Substances 0.000 description 5
239000002198 insoluble material Substances 0.000 description 5
239000012267 brine Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
241000894007 species Species 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
241001502500 Trichomonadida Species 0.000 description 3
208000005448 Trichomonas Infections Diseases 0.000 description 3
206010044620 Trichomoniasis Diseases 0.000 description 3
239000000370 acceptor Substances 0.000 description 3
239000002253 acid Substances 0.000 description 3
-1 alkali metal alkoxide Chemical class 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
238000006748 scratching Methods 0.000 description 3
230000002393 scratching effect Effects 0.000 description 3
PJEXUIKBGBSHBS-UHFFFAOYSA-N 1-(hydroxymethyl)pyrrolidin-2-one Chemical compound OCN1CCCC1=O PJEXUIKBGBSHBS-UHFFFAOYSA-N 0.000 description 2
HBUDEAAWZIMAEJ-UHFFFAOYSA-N 2-(3-azabicyclo[3.2.2]nonan-3-yl)ethanol Chemical compound C12CN(CC(CC1)CC2)CCO HBUDEAAWZIMAEJ-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000002024 ethyl acetate extract Substances 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
PTBKFATYSVLSSD-UHFFFAOYSA-N nifuroxime Chemical compound ON=CC1=CC=C([N+]([O-])=O)O1 PTBKFATYSVLSSD-UHFFFAOYSA-N 0.000 description 2
239000000126 substance Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
XRIBIDPMFSLGFS-UHFFFAOYSA-N 2-(dimethylamino)-2-methylpropan-1-ol Chemical compound CN(C)C(C)(C)CO XRIBIDPMFSLGFS-UHFFFAOYSA-N 0.000 description 1
LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
LICHZOBEUWVYSY-UHFFFAOYSA-N 3-azabicyclo[3.2.2]nonane Chemical compound C1CC2CCC1CNC2 LICHZOBEUWVYSY-UHFFFAOYSA-N 0.000 description 1
SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical compound [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
239000004157 Nitrosyl chloride Substances 0.000 description 1
241000224527 Trichomonas vaginalis Species 0.000 description 1
241001058196 Tritrichomonas foetus Species 0.000 description 1
206010000210 abortion Diseases 0.000 description 1
231100000176 abortion Toxicity 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001414 amino alcohols Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
210000003756 cervix mucus Anatomy 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
150000001983 dialkylethers Chemical class 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000006196 drop Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000036512 infertility Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
SEBNPZMOBUCYCA-UHFFFAOYSA-N morpholin-4-ylmethanol Chemical compound OCN1CCOCC1 SEBNPZMOBUCYCA-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
235000019392 nitrosyl chloride Nutrition 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
239000002244 precipitate 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
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
210000003708 urethra Anatomy 0.000 description 1
206010046901 vaginal discharge Diseases 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cosmetics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL29189A 1966-12-28 1967-12-21 Esters of 3-(5'-nitro-2'-furyl)-5-alkylisoxazole-4-carboxylic acids IL29189A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US60515566A	1966-12-28	1966-12-28

Publications (1)

Publication Number	Publication Date
IL29189A true IL29189A (en)	1972-06-28

Family

ID=24422488

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL29189A IL29189A (en)	1966-12-28	1967-12-21	Esters of 3-(5'-nitro-2'-furyl)-5-alkylisoxazole-4-carboxylic acids

Country Status (14)

Country	Link
US (1)	US3465000A (fr)
AT (1)	AT271474B (fr)
BE (1)	BE708636A (fr)
CH (1)	CH484936A (fr)
DE (1)	DE1695534A1 (fr)
DK (1)	DK123359B (fr)
ES (1)	ES348709A1 (fr)
FR (2)	FR1560394A (fr)
GB (1)	GB1212698A (fr)
GR (1)	GR34949B (fr)
IL (1)	IL29189A (fr)
NL (1)	NL6717736A (fr)
NO (1)	NO126181B (fr)
SE (1)	SE338048B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL85691A0 (en) *	1987-04-10	1988-08-31	Pennwalt Corp	5-(phenyl or phenoxymethyl)-3-(2-furanyl or 2-thienyl)-3-(1h-imidazol-1-ylmethyl)-2-methylisoxazolidines and salts thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US1889678A (en) *	1929-11-01	1932-11-29	Mannich Charles	Aromatic esters of amino alcohols and process of manufacture
US2421129A (en) *	1944-06-22	1947-05-27	Oradent Chemical Co Inc	Beta-isobutyl amino-beta, betadimethyl, ethyl benzoate

1966
- 1966-12-28 US US605155A patent/US3465000A/en not_active Expired - Lifetime
1967
- 1967-12-21 IL IL29189A patent/IL29189A/en unknown
- 1967-12-22 GR GR670134949A patent/GR34949B/el unknown
- 1967-12-22 DK DK647167AA patent/DK123359B/da unknown
- 1967-12-27 ES ES348709A patent/ES348709A1/es not_active Expired
- 1967-12-27 DE DE19671695534 patent/DE1695534A1/de active Pending
- 1967-12-27 SE SE17784/67A patent/SE338048B/xx unknown
- 1967-12-27 NO NO00171162A patent/NO126181B/no unknown
- 1967-12-28 AT AT1175167A patent/AT271474B/de active
- 1967-12-28 FR FR1560394D patent/FR1560394A/fr not_active Expired
- 1967-12-28 BE BE708636D patent/BE708636A/xx unknown
- 1967-12-28 GB GB58763/67A patent/GB1212698A/en not_active Expired
- 1967-12-28 CH CH1826867A patent/CH484936A/de not_active IP Right Cessation
- 1967-12-28 NL NL6717736A patent/NL6717736A/xx unknown
1968
- 1968-03-27 FR FR145698A patent/FR7385M/fr not_active Expired

Also Published As

Publication number	Publication date
CH484936A (de)	1970-01-31
FR1560394A (fr)	1969-03-21
ES348709A1 (es)	1969-07-01
GR34949B (el)	1968-07-24
SE338048B (fr)	1971-08-30
DK123359B (da)	1972-06-12
US3465000A (en)	1969-09-02
GB1212698A (en)	1970-11-18
NO126181B (fr)	1973-01-02
AT271474B (de)	1969-06-10
FR7385M (fr)	1969-10-27
BE708636A (fr)	1968-06-28
DE1695534A1 (de)	1972-03-02
NL6717736A (fr)	1968-07-01

Publication	Publication Date	Title
DE69017479T2 (de)	1995-07-13	Azabicycloheptenderivate und ihre Salze, Verfahren zu ihrer Herstellung, ihre Verwendung als Arzneimittel und diese enthaltende Zubereitungen.
US3029189A (en)	1962-04-10	S-aryl-z-mno-x-qxazolibinones
US3679698A (en)	1972-07-25	2-nitroimidazoles
US4125620A (en)	1978-11-14	2-[(2',6'-Disubstituted-phenyl)-imino]-imidazolidines and salts thereof
JPS62161728A (ja)	1987-07-17	抗菌剤
EP0830863A1 (fr)	1998-03-25	Médicaments améliorateurs de l'irrigation sanguine gastrointestinale
PL96677B1 (pl)	1978-01-31	Sposob wytwarzania nowych zwiazkow tetracyklinowych
US4518712A (en)	1985-05-21	Piperazine derivative and analgesic composition containing the same
EP0053767B1 (fr)	1984-09-12	Dérivés tricycliques de la cytosine pour utilisation en médicaments et procédé pour leur préparation
DE2204574A1 (de)	1973-08-09	Verfahren zur herstellung von 3-aminobenzo-1,2,4-triazin-di-n-oxiden (1,4)
DE2459380A1 (de)	1975-06-19	Verfahren zur herstellung von oxazolderivaten
DE68914471T2 (de)	1994-07-28	Thieno[2,3-d]azepinderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen.
CH646972A5 (en)	1984-12-28	Process for the preparation of new 5-aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids
US3277108A (en)	1966-10-04	Certain aralkyl sydnonimines
EP0134928A1 (fr)	1985-03-27	Dérivés de l'imidazo[1,5-a]pyrimidine et procédé pour leur préparation
DE2362754A1 (de)	1974-07-11	Cyclopropylmethylamine, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel
EP0059108B1 (fr)	1985-08-14	Dérivés d'acide dihydroxibenzoique
US3836656A (en)	1974-09-17	Substituted purines as hypolipidemics
DE3688161T2 (de)	1993-10-14	Gegebenenfalls etherifizierte oder esterifizierte in Stellung 2 substituierte 4-OH-Chinolincarbonsäurederivate, Verfahren und Zwischenprodukte zu ihrer Herstellung, ihre Anwendung als Arzneimittel und diese enthaltende Zubereitungen.
US3465000A (en)	1969-09-02	Basic esters of certain substituted isoxazole-4-carboxylic acids
US4014876A (en)	1977-03-29	Isoxazole derivatives
US4207317A (en)	1980-06-10	1-Aryl-4-carbamoyl-pyrazolin-5-ones
US3324124A (en)	1967-06-06	Thiamine derivatives
US3350407A (en)	1967-10-31	Sulfur containing pyrazole derivatives
DE1695115A1 (de)	1972-03-30	Verfahren zur Herstellung von neuen Furazanderivaten