IE51342B1 - Substituted pyrazinyl-1,2,4-oxadiazol-5-ones,a process for preparing same and a pharmaceutical composition containing same - Google Patents

Substituted pyrazinyl-1,2,4-oxadiazol-5-ones,a process for preparing same and a pharmaceutical composition containing same

Info

Publication number: IE51342B1
Authority: IE; Ireland
Prior art keywords: compound; pharmaceutical composition; hydrogen; hypertension; formula
Prior art date: 1980-06-27

Application number

IE1431/81A

Other languages

English (en)

Other versions

IE811431L (en

Original Assignee

Merck & Co Inc

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.)

1980-06-27

Filing date

1981-06-26

Publication date

1986-12-10

1981-06-26 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1981-12-27 Publication of IE811431L publication Critical patent/IE811431L/xx

1986-12-10 Publication of IE51342B1 publication Critical patent/IE51342B1/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 8
238000004519 manufacturing process Methods 0.000 title claims 2
150000001875 compounds Chemical class 0.000 claims abstract description 36
206010020772 Hypertension Diseases 0.000 claims abstract description 7
206010030113 Oedema Diseases 0.000 claims abstract description 7
238000000034 method Methods 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
229960002003 hydrochlorothiazide Drugs 0.000 claims description 4
241001465754 Metazoa Species 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
ALYSDVMPAXWPNM-UHFFFAOYSA-N 3-pyrazin-2-yl-2h-1,2,4-oxadiazol-5-one Chemical class N1OC(=O)N=C1C1=CN=CC=N1 ALYSDVMPAXWPNM-UHFFFAOYSA-N 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
239000004480 active ingredient Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
239000002775 capsule Substances 0.000 description 4
239000002934 diuretic Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
230000001882 diuretic effect Effects 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
KSEHSAXZBNRCCY-UHFFFAOYSA-N 3-chloropyrazine-2,6-diamine Chemical compound NC1=CN=C(Cl)C(N)=N1 KSEHSAXZBNRCCY-UHFFFAOYSA-N 0.000 description 2
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000005469 granulation Methods 0.000 description 2
230000003179 granulation Effects 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000011777 magnesium Substances 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
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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 2
239000000843 powder Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
-1 6-chloro-N-(cyanoaminoiminomethyl)pyrazinecarboxamide Chemical compound 0.000 description 1
206010014418 Electrolyte imbalance Diseases 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
229940078495 calcium phosphate dibasic Drugs 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000013066 combination product Substances 0.000 description 1
229940127555 combination product Drugs 0.000 description 1
239000007891 compressed tablet Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
238000011049 filling Methods 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000011812 mixed powder Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
WWCISNWFARWAER-UHFFFAOYSA-N n-[(2-cyanohydrazinyl)methylidene]pyrazine-2-carboxamide Chemical class N#CNNC=NC(=O)C1=CN=CC=N1 WWCISNWFARWAER-UHFFFAOYSA-N 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 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
238000005303 weighing Methods 0.000 description 1
238000005550 wet granulation Methods 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Heart & Thoracic Surgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Photoreceptors In Electrophotography (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

IE1431/81A 1980-06-27 1981-06-26 Substituted pyrazinyl-1,2,4-oxadiazol-5-ones,a process for preparing same and a pharmaceutical composition containing same IE51342B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/163,614 US4309430A (en)	1980-06-27	1980-06-27	Pyrazinyl-1,2,4-oxadiazole-5-ones, for treatment of edema, and processes for preparing same

Publications (2)

Publication Number	Publication Date
IE811431L IE811431L (en)	1981-12-27
IE51342B1 true IE51342B1 (en)	1986-12-10

Family

ID=22590790

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE1431/81A IE51342B1 (en)	1980-06-27	1981-06-26	Substituted pyrazinyl-1,2,4-oxadiazol-5-ones,a process for preparing same and a pharmaceutical composition containing same

Country Status (10)

Country	Link
US (1)	US4309430A (2)
EP (1)	EP0043123B1 (2)
JP (1)	JPS5756480A (2)
AT (1)	ATE7697T1 (2)
DE (1)	DE3163867D1 (2)
DK (1)	DK283881A (2)
ES (1)	ES503308A0 (2)
GR (1)	GR74609B (2)
IE (1)	IE51342B1 (2)
PT (1)	PT73259B (2)

Families Citing this family (33)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5066662A (en) *	1990-05-21	1991-11-19	Warner-Lambert Company	Substituted oxazolidin-2-ones and 1,2,4-oxadiazolin-5-ones and derivatives thereof acting at muscarinic receptors
KR20170015566A (ko)	2008-11-10	2017-02-08	버텍스 파마슈티칼스 인코포레이티드	Ａｔｒ 키나제의 억제제로서 유용한 화합물
ES2663222T3 (es)	2008-12-19	2018-04-11	Vertex Pharmaceuticals Incorporated	Derivados de pirazina útiles como inhibidores de la quinasa ATR
US8969356B2 (en)	2010-05-12	2015-03-03	Vertex Pharmaceuticals Incorporated	Compounds useful as inhibitors of ATR kinase
JP2013526540A (ja)	2010-05-12	2013-06-24	バーテックスファーマシューティカルズインコーポレイテッド	Ａｔｒキナーゼ阻害剤として有用な化合物
JP5856151B2 (ja)	2010-05-12	2016-02-09	バーテックスファーマシューティカルズインコーポレイテッドＶｅｒｔｅｘＰｈａｒｍａｃｅｕｔｉｃａｌｓＩｎｃｏｒｐｏｒａｔｅｄ	Ａｔｒキナーゼ阻害剤として有用な２−アミノピリジン誘導体
JP2013529200A (ja)	2010-05-12	2013-07-18	バーテックスファーマシューティカルズインコーポレイテッド	Ａｔｒキナーゼ阻害剤として有用な化合物
JP2013526539A (ja)	2010-05-12	2013-06-24	バーテックスファーマシューティカルズインコーポレイテッド	Ａｔｒキナーゼ阻害剤として有用なピラジン
US9630956B2 (en)	2010-05-12	2017-04-25	Vertex Pharmaceuticals Incorporated	Compounds useful as inhibitors of ATR kinase
CA2803802A1 (en)	2010-06-23	2011-12-29	Vertex Pharmaceuticals Incorporated	Pyrrolo- pyrazine derivatives useful as inhibitors of atr kinase
JP2014510151A (ja)	2011-04-05	2014-04-24	バーテックスファーマシューティカルズインコーポレイテッド	Ａｔｒキナーゼ（ｔｒａｋｉｎａｓｅ）阻害剤として有用なアミノピラジン化合物
EP2723745A1 (en)	2011-06-22	2014-04-30	Vertex Pharmaceuticals Inc.	Compounds useful as inhibitors of atr kinase
WO2012178125A1 (en)	2011-06-22	2012-12-27	Vertex Pharmaceuticals Incorporated	Compounds useful as inhibitors of atr kinase
WO2012178124A1 (en)	2011-06-22	2012-12-27	Vertex Pharmaceuticals Incorporated	Compounds useful as inhibitors of atr kinase
WO2013049719A1 (en)	2011-09-30	2013-04-04	Vertex Pharmaceuticals Incorporated	Compounds useful as inhibitors of atr kinase
KR20140084112A (ko)	2011-09-30	2014-07-04	버텍스 파마슈티칼스 인코포레이티드	Ａｔｒ 키나제의 억제제로서 유용한 화합물
SG10201606774UA (en)	2011-09-30	2016-10-28	Vertex Pharma	Processes for making compounds useful as inhibitors of atr kinase
WO2013049859A1 (en)	2011-09-30	2013-04-04	Vertex Pharmaceuticals Incorporated	Treating pancreatic cancer and non-small cell lung cancer with atr inhibitors
US8853217B2 (en)	2011-09-30	2014-10-07	Vertex Pharmaceuticals Incorporated	Compounds useful as inhibitors of ATR kinase
WO2013071088A1 (en)	2011-11-09	2013-05-16	Vertex Pharmaceuticals Incorporated	Compounds useful as inhibitors of atr kinase
US8841337B2 (en)	2011-11-09	2014-09-23	Vertex Pharmaceuticals Incorporated	Compounds useful as inhibitors of ATR kinase
WO2013071094A1 (en)	2011-11-09	2013-05-16	Vertex Pharmaceuticals Incorporated	Compounds useful as inhibitors of atr kinase
US8841450B2 (en)	2011-11-09	2014-09-23	Vertex Pharmaceuticals Incorporated	Compounds useful as inhibitors of ATR kinase
WO2013071085A1 (en)	2011-11-09	2013-05-16	Vertex Pharmaceuticals Incorporated	Pyrazine compounds useful as inhibitors of atr kinase
CA2869309C (en)	2012-04-05	2021-02-09	Vertex Pharmaceuticals Incorporated	Compounds useful as inhibitors of atr kinase and combination therapies thereof
US8999632B2 (en)	2012-10-04	2015-04-07	Vertex Pharmaceuticals Incorporated	Method for measuring ATR inhibition mediated increases in DNA damage
US8912198B2 (en)	2012-10-16	2014-12-16	Vertex Pharmaceuticals Incorporated	Compounds useful as inhibitors of ATR kinase
SI2941432T1 (en)	2012-12-07	2018-07-31	Vertex Pharmaceuticals Incorporated	2-AMINO-6-FLUORO-N- (5-FLUORO-4- (4- (4- (OXETHAN-3-YL) PIPERAZIN-1-CARBONYL) PIPERIDIN-1-YLIPRIDIN-3-YL) 1,5 ALFA) PYRIMIDINE-3-CARBOXAMIDE AS ATR KINAZE INHIBITOR
JP2016512815A (ja)	2013-03-15	2016-05-09	バーテックスファーマシューティカルズインコーポレイテッドＶｅｒｔｅｘＰｈａｒｍａｃｅｕｔｉｃａｌｓＩｎｃｏｒｐｏｒａｔｅｄ	Ａｔｒキナーゼの阻害剤として有用な縮合ピラゾロピリミジン誘導体
DK3077397T3 (da)	2013-12-06	2019-12-16	Vertex Pharma	2-amino-6-fluor-n-[5-fluor-pyridin-3-yl]pyrazolo[1,5-a]pyrimidin-3-carboxamidforbindelse anvendelig som atr-kinase-inhibitor, dens fremstilling, forskellige faste former og radiomarkerede derivater deraf
PL3152212T3 (pl)	2014-06-05	2020-06-15	Vertex Pharmaceuticals Inc.	Radioznakowane pochodne związku 2-amino-6-fluoro-n-[5-fluoro-piridyn-3-ylo]-pirazolo[1,5-a]pirymidino-3-karboksamidu przydatne jako inhibitor kinazy atr, wytwarzanie tego związku i jego różnych postaci stałych
LT3157566T (lt)	2014-06-17	2019-08-12	Vertex Pharmaceuticals Incorporated	Vėžio gydymo būdas, panaudojant chk1 ir atr inhibitorių derinį
HK1258570A1 (zh)	2015-09-30	2019-11-15	Vertex Pharmaceuticals Inc.	使用dna损伤剂及atr抑制剂的组合治疗癌症的方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3515723A (en) *	1967-11-14	1970-06-02	Merck & Co Inc	2 - (5 - amino - 1h - 1,2,4 - triazol - 3 - yl)- 3-aminopyrazines and processes for their preparation
US3770739A (en) *	1972-09-11	1973-11-06	American Cyanamid Co	Cyclorpropyl-1,2,4-oxadiazolylpyrazines

1980
- 1980-06-27 US US06/163,614 patent/US4309430A/en not_active Expired - Lifetime
1981
- 1981-06-22 GR GR65307A patent/GR74609B/el unknown
- 1981-06-23 ES ES503308A patent/ES503308A0/es active Granted
- 1981-06-25 PT PT73259A patent/PT73259B/pt unknown
- 1981-06-26 DK DK283881A patent/DK283881A/da not_active Application Discontinuation
- 1981-06-26 JP JP56098426A patent/JPS5756480A/ja active Pending
- 1981-06-26 EP EP81104974A patent/EP0043123B1/en not_active Expired
- 1981-06-26 IE IE1431/81A patent/IE51342B1/en unknown
- 1981-06-26 AT AT81104974T patent/ATE7697T1/de active
- 1981-06-26 DE DE8181104974T patent/DE3163867D1/de not_active Expired

Also Published As

Publication number	Publication date
ATE7697T1 (de)	1984-06-15
EP0043123A1 (en)	1982-01-06
ES8300758A1 (es)	1982-11-01
ES503308A0 (es)	1982-11-01
US4309430A (en)	1982-01-05
PT73259B (en)	1983-06-28
DE3163867D1 (en)	1984-07-05
GR74609B (2)	1984-06-29
IE811431L (en)	1981-12-27
DK283881A (da)	1981-12-28
EP0043123B1 (en)	1984-05-30
JPS5756480A (en)	1982-04-05
PT73259A (en)	1981-07-01

Publication	Publication Date	Title
US4309430A (en)	1982-01-05	Pyrazinyl-1,2,4-oxadiazole-5-ones, for treatment of edema, and processes for preparing same
US3573306A (en)	1971-03-30	Process for preparation of n-substituted 3,5-diamino-6-halopyrazinamides
US4460607A (en)	1984-07-17	Lipid absorption-inhibiting agents and their use
JPS6156227B2 (2)	1986-12-01
US4309540A (en)	1982-01-05	Substituted pyrazinyl-1,2,4-oxadiazoles
JPS5989671A (ja)	1984-05-23	２，５−ピペラジンジオン誘導体
US4454132A (en)	1984-06-12	Pharmaceutical compositions of novel substituted pyrazinyl-1,2,4-oxadiazoles useful in the treatment of edema and hypertension
EP0017153B1 (en)	1983-01-26	Novel pyrazinecarboxamides, processes for preparing and pharmaceutical compositions containing the same
US4362724A (en)	1982-12-07	Method of treating edema and hypertension and pharmaceutical composition therefor in which the active ingredient comprises a novel substituted pyrazinyl-1,2,4-oxadiazole and a kaliuretic diuretic
US3923994A (en)	1975-12-02	Anti-arthritic compositions comprising a 3-aryl 2-thiohydantoin and methods of producing anti-arthritic acitvity
US3586688A (en)	1971-06-22	Certain aminopyridinecarbonyl guanidines
US4360521A (en)	1982-11-23	7[3,6-Dihydro-1(2H)-pyridyl]-2-oxo-2H-[1,2,4]oxadiazolo[2,3-c]pyrimidine-5-carbamate compounds
US3021325A (en)	1962-02-13	Carbamyl substituted 2, 3, 4, 5-tetrahydrobenzodiazepine compounds
GB1580588A (en)	1980-12-03	-aryl- , -bis( -(disubstituted amino)-alkyl)-acetamides and related compounds
US4328235A (en)	1982-05-04	Suppressing pain with benzothiazol-2(3H)-ones
US4103018A (en)	1978-07-25	2-[4-(Polyhalo-2-hydroxy-2-propyl)anilino]-2-oxazolin-4-ones and thiazolin-4-ones corresponding thereto
US2928768A (en)	1960-03-15	Use of substituted amino-formoguanamines in diuretic therapy
US3856958A (en)	1974-12-24	1-(5-phenyl-4-oxo-2-oxazolin-2-yl)-4-cinnamoylpiperazines in the treatment of depression
NL8202227A (nl)	1983-01-03	4-amino.benzylaminederivaten en werkwijzen voor hun bereiding en hun toepassing als farmaceutica.
DE2613328C3 (de)	1978-05-11	l-Methyl-2-(m-trifluormethyl-phenyl)äthylamid der p-Pentylamino-phenoxyessigsäure, ein Verfahren zu dessen Herstellung sowie Arzneimittel
US3968217A (en)	1976-07-06	5-(3-)SUBSTITUTED-10,11-DIHYDRO-5H-dibenz[b,f]azepines
JPH0146511B2 (2)	1989-10-09
US3818095A (en)	1974-06-18	Compositions of 1,2-dilower alkyl-3(and/or4)-aryl-3-pyrazolines and salts thereof and method of lowering blood sugar levels with same
CA2315835C (en)	2008-03-25	New crystalline form of 1-methyl-5-p-toluoylpyrrole-2-acetamidoacetic acid guaiacyl ester
US3655894A (en)	1972-04-11	Compositions for inhibiting gastric acid secretion