LU83886A1 - Nouveaux derives de la furo-(3,4-c)-pyridine leur preparation et leur emploi therapeutique - Google Patents

Nouveaux derives de la furo-(3,4-c)-pyridine leur preparation et leur emploi therapeutique Download PDF

Info

Publication number: LU83886A1
Authority: LU; Luxembourg
Prior art keywords: radical; carbon atoms; pyridine; furo; alpha
Prior art date: 1981-02-10

Application number

LU83886A

Other languages

English (en)

French (fr)

Inventor

A Esanu

Original Assignee

Scras

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.)

1981-02-10

Filing date

1982-01-21

Publication date

1982-06-30

1982-01-21 Application filed by Scras filed Critical Scras

1982-06-30 Publication of LU83886A1 publication Critical patent/LU83886A1/fr

Links

230000001225 therapeutic effect Effects 0.000 title claims description 5
238000002360 preparation method Methods 0.000 title claims description 3
GJVNMIQVQXYJCP-UHFFFAOYSA-N furo[3,4-c]pyridine Chemical class C1=NC=CC2=[C]OC=C21 GJVNMIQVQXYJCP-UHFFFAOYSA-N 0.000 title description 14
150000001875 compounds Chemical class 0.000 claims description 34
238000000034 method Methods 0.000 claims description 21
-1 alkyl radical Chemical class 0.000 claims description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 8
239000011777 magnesium Substances 0.000 claims description 8
229910052749 magnesium Inorganic materials 0.000 claims description 8
LXNHXLLTXMVWPM-UHFFFAOYSA-N Vitamin B6 Natural products CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 claims description 3
239000000460 chlorine Chemical group 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
229910052801 chlorine Chemical group 0.000 claims description 2
229910052731 fluorine Chemical group 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
229910052740 iodine Chemical group 0.000 claims description 2
239000000203 mixture Substances 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
235000008160 pyridoxine Nutrition 0.000 claims description 2
239000011677 pyridoxine Substances 0.000 claims description 2
150000003254 radicals Chemical class 0.000 claims description 2
150000003333 secondary alcohols Chemical class 0.000 claims description 2
229940011671 vitamin b6 Drugs 0.000 claims description 2
BCAYMTVSZSZWMC-UHFFFAOYSA-N C(C)(C)=CC1=NC=C(C(=C1O)C=O)CO Chemical compound C(C)(C)=CC1=NC=C(C(=C1O)C=O)CO BCAYMTVSZSZWMC-UHFFFAOYSA-N 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 claims 1
125000001246 bromo group Chemical group Br* 0.000 claims 1
239000000047 product Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
241001465754 Metazoa Species 0.000 description 11
239000011674 pyridoxal Substances 0.000 description 9
229960003581 pyridoxal Drugs 0.000 description 9
238000004458 analytical method Methods 0.000 description 8
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
241000700159 Rattus Species 0.000 description 5
238000000921 elemental analysis Methods 0.000 description 5
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
239000002934 diuretic Substances 0.000 description 4
229940030606 diuretics Drugs 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000008280 blood Substances 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
235000012000 cholesterol Nutrition 0.000 description 3
235000013305 food Nutrition 0.000 description 3
150000002632 lipids Chemical class 0.000 description 3
WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 3
210000002700 urine Anatomy 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
RADKZDMFGJYCBB-UHFFFAOYSA-N Pyridoxal Chemical compound CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000036772 blood pressure Effects 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
AGHANLSBXUWXTB-UHFFFAOYSA-N tienilic acid Chemical compound ClC1=C(Cl)C(OCC(=O)O)=CC=C1C(=O)C1=CC=CS1 AGHANLSBXUWXTB-UHFFFAOYSA-N 0.000 description 2
229960000356 tienilic acid Drugs 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
NNMBNYHMJRJUBC-UHFFFAOYSA-N 1-bromo-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(Br)=C1 NNMBNYHMJRJUBC-UHFFFAOYSA-N 0.000 description 1
XLQSXGGDTHANLN-UHFFFAOYSA-N 1-bromo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Br)C=C1 XLQSXGGDTHANLN-UHFFFAOYSA-N 0.000 description 1
NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
FLVIETJQVDUKMQ-UHFFFAOYSA-N 2,4,5-tris(hydroxymethyl)pyridin-3-ol Chemical group OCC1=CN=C(CO)C(O)=C1CO FLVIETJQVDUKMQ-UHFFFAOYSA-N 0.000 description 1
XKIFTEHOCFPRJE-UHFFFAOYSA-N 2-(4-bromophenoxy)-n,n-diethylethanamine Chemical compound CCN(CC)CCOC1=CC=C(Br)C=C1 XKIFTEHOCFPRJE-UHFFFAOYSA-N 0.000 description 1
BFJMHTOBRRZELQ-UHFFFAOYSA-N 3-iodo-2h-pyrazolo[3,4-c]pyridine Chemical compound N1=CC=C2C(I)=NNC2=C1 BFJMHTOBRRZELQ-UHFFFAOYSA-N 0.000 description 1
CXFIWPAUNODACX-KQQUZDAGSA-N 4-[(1e,3e)-4-[4-(dimethylamino)phenyl]buta-1,3-dienyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1\C=C\C=C\C1=CC=C(N(C)C)C=C1 CXFIWPAUNODACX-KQQUZDAGSA-N 0.000 description 1
QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
206010003210 Arteriosclerosis Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
206010009192 Circulatory collapse Diseases 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
102000004895 Lipoproteins Human genes 0.000 description 1
108090001030 Lipoproteins Proteins 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
208000004880 Polyuria Diseases 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
210000000702 aorta abdominal Anatomy 0.000 description 1
208000037849 arterial hypertension Diseases 0.000 description 1
208000011775 arteriosclerosis disease Diseases 0.000 description 1
239000003181 biological factor Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000011109 contamination Methods 0.000 description 1
230000037213 diet Effects 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000035619 diuresis Effects 0.000 description 1
230000001882 diuretic effect Effects 0.000 description 1
238000001962 electrophoresis Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000006911 enzymatic reaction Methods 0.000 description 1
210000003238 esophagus Anatomy 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
201000005577 familial hyperlipidemia Diseases 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
239000011630 iodine Chemical group 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
235000008164 pyridoxal Nutrition 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
206010040560 shock Diseases 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
231100000064 subacute toxicity study Toxicity 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
- 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)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Hematology (AREA)
Diabetes (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyridine Compounds (AREA)
Coloring Foods And Improving Nutritive Qualities (AREA)

LU83886A 1981-02-10 1982-01-21 Nouveaux derives de la furo-(3,4-c)-pyridine leur preparation et leur emploi therapeutique LU83886A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB8104072		1981-02-10
GB8104072		1981-02-10

Publications (1)

Publication Number	Publication Date
LU83886A1 true LU83886A1 (fr)	1982-06-30

Family

ID=10519587

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU83886A LU83886A1 (fr)	1981-02-10	1982-01-21	Nouveaux derives de la furo-(3,4-c)-pyridine leur preparation et leur emploi therapeutique

Country Status (34)

Country	Link
US (1)	US4383998A (xx)
JP (1)	JPS57150688A (xx)
KR (1)	KR870000206B1 (xx)
AR (1)	AR230284A1 (xx)
AU (1)	AU545876B2 (xx)
BE (1)	BE891797A (xx)
CA (1)	CA1175837A (xx)
CH (1)	CH649554A5 (xx)
DE (1)	DE3204596A1 (xx)
DK (1)	DK157551C (xx)
DZ (1)	DZ376A1 (xx)
ES (1)	ES8302714A1 (xx)
FI (1)	FI75347C (xx)
FR (2)	FR2499406A1 (xx)
GB (1)	GB2092586B (xx)
GR (1)	GR75905B (xx)
HK (1)	HK22485A (xx)
HU (1)	HU185088B (xx)
IE (1)	IE52376B1 (xx)
IL (1)	IL64759A (xx)
IN (1)	IN156817B (xx)
IT (1)	IT1157252B (xx)
LU (1)	LU83886A1 (xx)
MA (1)	MA19378A1 (xx)
MX (1)	MX6983E (xx)
NL (1)	NL186697C (xx)
NO (1)	NO156373C (xx)
NZ (1)	NZ199528A (xx)
OA (1)	OA07003A (xx)
PT (1)	PT74408B (xx)
SE (1)	SE456994B (xx)
SG (1)	SG85384G (xx)
YU (1)	YU44000B (xx)
ZA (1)	ZA82158B (xx)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4735950A (en) *	1983-04-05	1988-04-05	Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S)	Furo-(3,4-C)-pyridine derivatives and therapeutic composition containing the same
IN160104B (xx) *	1983-04-05	1987-06-27	Scras
GB8327817D0 (en) *	1983-10-18	1983-11-16	Scras	4-halo-furo-(3 4-c)-pyridine derivatives
GB8330517D0 (en) *	1983-11-16	1983-12-21	Scras	6-vinyl-furo-(3,4-c)pyridine derivatives
GB8330658D0 (en) *	1983-11-17	1983-12-29	Scras	7-carboxymethoxy-furo-(3,4-c)-pyridine derivatives
GB8402740D0 (en) *	1984-02-02	1984-03-07	Scras	Furo-(3 4-c)-pyridine derivatives
GB8414559D0 (en) *	1984-06-07	1984-07-11	Scras	Pyridine derivatives
GB8422379D0 (en) *	1984-09-05	1984-10-10	Scras	Derivatives
GB8427218D0 (en) *	1984-10-27	1984-12-05	Scras	Pyridine derivatives
DE3519693A1 (de) *	1985-06-01	1987-01-02	Basf Ag	Pyridin-derivate, ihre herstellung und verwendung
DE3990349T1 (de) *	1988-04-06	1990-04-26	Scras	Stereospezifisches verfahren zur herstellung von enantiomeren von furo(3,4-c)pyridin, so erhaltene verbindungen und therapeutische zusammensetzungen auf basis dieser verbindungen
GB8808001D0 (en) *	1988-04-06	1988-05-05	Scras	Stereospecific preparative process for furol(3,4-c)pyridine derivatives
GB8907480D0 (en) *	1989-04-03	1989-05-17	Scaras Societe De Conseils De	Separation of insomers of furo(3,4-c)pyridine derivatives
GB8917168D0 (en) *	1989-07-27	1989-09-13	Scras	Asymmetric synthesis of furo(3,4-c)pyridine derivatives
US5130252A (en) *	1990-05-14	1992-07-14	Synthetech, Inc.	Resolution of furopyridine enantiomers and synthetic precursors thereof
GB0221494D0 (en) *	2002-09-16	2002-10-23	Generics Uk Ltd	Novel processes for the preparation of 1.3-dihydro-6-methylfuro (3,4-c) pyndin derivatives
HUP0300990A2 (hu) *	2003-04-15	2005-05-30	SynoSens Kutató és Fejlesztő Kft.	Szinergista gyógyszer-kombináció a diabetesz megelőzésére vagy kezelésére
CA2532807A1 (en) *	2003-07-17	2005-02-03	Cotherix, Inc.	Combination therapies for treatment of hypertension and complications in patients with diabetes or metabolic syndrome
US20060089374A1 (en) *	2003-07-17	2006-04-27	Glenn Cornett	Enantiomeric compositions of cicletanine, alone and in combination with other agents, for the treatment of disease
WO2006034510A2 (en) *	2004-09-22	2006-03-30	Glenn Cornett	Enantiomeric compositions of cicletanine, alone and in combination with other agents, for the treatment of disease
US20060153934A1 (en) *	2005-01-13	2006-07-13	Navitas Pharma	Combination therapies of cicletanine and magnesium
US20060154959A1 (en) *	2005-01-13	2006-07-13	Navitas Pharma	Combination therapies of cicletanine and carvedilol
US20070141174A1 (en) *	2005-01-13	2007-06-21	Navitas Pharma, Inc.	Enantiomeric compositions of cicletanine, in combination with other agents, for the treatment of hypertension
US20080096915A1 (en) *	2005-01-13	2008-04-24	Greenberg Traurig LLP	Compositions for the treatment of metabolic disorders
US20070105817A1 (en) *	2005-11-09	2007-05-10	Jim Page	Use of cicletanine and other furopyridines for treatment of systolic-predominant hypertension, isolated systolic hypertension, elevated pulse pressure, and general hypertension
WO2008085872A1 (en) *	2007-01-03	2008-07-17	Cornett Glenn V	Cicletanine and pkc inhibitors in the treatment of pulmonary and cardiac disorders
AR073259A1 (es) *	2008-07-29	2010-10-28	Merck & Co Inc	Derivados de furosemida utiles como diureticos
US8214941B2 (en)	2008-10-02	2012-07-10	Kohler Co.	Slip-fit clamping system for mounting a fitting on a wall
EP2485734B1 (en) *	2009-10-09	2014-07-02	Merck Sharp & Dohme Corp.	Diuretics
EP2498605B1 (en) *	2009-10-29	2014-08-27	Merck Sharp & Dohme Corp.	Diuretics
US9522138B2 (en) *	2013-12-31	2016-12-20	Don C. Rockey	Systems, methods, techniques, and compounds in research and treatment of portal hypertension and other conditions

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZA786269B (en) *	1977-11-25	1979-10-31	Scras	New pyridine derivative,its preparation and use

1982
- 1982-01-06 IN IN11/DEL/82A patent/IN156817B/en unknown
- 1982-01-08 US US06/338,140 patent/US4383998A/en not_active Expired - Lifetime
- 1982-01-11 ZA ZA82158A patent/ZA82158B/xx unknown
- 1982-01-11 IL IL64759A patent/IL64759A/xx unknown
- 1982-01-12 GR GR66981A patent/GR75905B/el unknown
- 1982-01-15 BE BE0/207069A patent/BE891797A/fr not_active IP Right Cessation
- 1982-01-19 NL NLAANVRAGE8200180,A patent/NL186697C/xx not_active IP Right Cessation
- 1982-01-20 NZ NZ199528A patent/NZ199528A/en unknown
- 1982-01-21 AR AR288193A patent/AR230284A1/es active
- 1982-01-21 LU LU83886A patent/LU83886A1/fr unknown
- 1982-01-28 OA OA57599A patent/OA07003A/xx unknown
- 1982-01-28 CH CH508/82A patent/CH649554A5/fr not_active IP Right Cessation
- 1982-01-28 NO NO820253A patent/NO156373C/no not_active IP Right Cessation
- 1982-02-01 MA MA19583A patent/MA19378A1/fr unknown
- 1982-02-04 FI FI820353A patent/FI75347C/fi not_active IP Right Cessation
- 1982-02-05 YU YU253/82A patent/YU44000B/xx unknown
- 1982-02-07 DZ DZ826443A patent/DZ376A1/fr active
- 1982-02-08 IT IT19502/82A patent/IT1157252B/it active
- 1982-02-08 GB GB8203522A patent/GB2092586B/en not_active Expired
- 1982-02-09 IE IE288/82A patent/IE52376B1/en not_active IP Right Cessation
- 1982-02-09 DK DK054382A patent/DK157551C/da not_active IP Right Cessation
- 1982-02-09 KR KR8200536A patent/KR870000206B1/ko not_active Expired
- 1982-02-09 AU AU80294/82A patent/AU545876B2/en not_active Expired
- 1982-02-09 SE SE8200744A patent/SE456994B/sv not_active IP Right Cessation
- 1982-02-09 MX MX829909U patent/MX6983E/es unknown
- 1982-02-09 CA CA000395857A patent/CA1175837A/en not_active Expired
- 1982-02-09 ES ES509449A patent/ES8302714A1/es not_active Expired
- 1982-02-09 PT PT74408A patent/PT74408B/pt unknown
- 1982-02-10 HU HU82405A patent/HU185088B/hu unknown
- 1982-02-10 DE DE19823204596 patent/DE3204596A1/de active Granted
- 1982-02-10 JP JP57019038A patent/JPS57150688A/ja active Granted
- 1982-02-10 FR FR8202136A patent/FR2499406A1/fr active Granted
- 1982-02-10 FR FR8202137A patent/FR2499574A1/fr active Granted
1984
- 1984-11-29 SG SG853/84A patent/SG85384G/en unknown
1985
- 1985-03-21 HK HK224/85A patent/HK22485A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
FR2499574B1 (xx)	1984-03-30
IL64759A (en)	1985-09-29
DE3204596A1 (de)	1982-09-09
NO156373C (no)	1987-09-09
OA07003A (fr)	1983-08-31
NL186697C (nl)	1991-02-01
NZ199528A (en)	1984-02-03
AR230284A1 (es)	1984-03-01
IT1157252B (it)	1987-02-11
JPH0261477B2 (xx)	1990-12-20
CA1175837A (en)	1984-10-09
MA19378A1 (fr)	1982-10-01
NO820253L (no)	1982-08-11
ES509449A0 (es)	1983-01-16
JPS57150688A (en)	1982-09-17
FR2499406A1 (fr)	1982-08-13
BE891797A (fr)	1982-04-30
YU44000B (en)	1990-02-28
KR870000206B1 (ko)	1987-02-16
FI820353L (fi)	1982-08-11
NL186697B (nl)	1990-09-03
CH649554A5 (fr)	1985-05-31
KR830009106A (ko)	1983-12-17
SE456994B (sv)	1988-11-21
FR2499574A1 (fr)	1982-08-13
AU545876B2 (en)	1985-08-01
IT8219502A0 (it)	1982-02-08
PT74408A (en)	1982-03-01
DZ376A1 (fr)	2004-09-13
DK157551B (da)	1990-01-22
DK54382A (da)	1982-08-11
MX6983E (es)	1987-01-19
IE820288L (en)	1982-08-10
DE3204596C2 (xx)	1991-07-04
AU8029482A (en)	1982-08-19
YU25382A (en)	1984-08-31
US4383998A (en)	1983-05-17
ZA82158B (en)	1982-11-24
DK157551C (da)	1990-06-11
NO156373B (no)	1987-06-01
GB2092586A (en)	1982-08-18
GB2092586B (en)	1984-09-26
FI75347C (fi)	1988-06-09
SG85384G (en)	1985-06-07
SE8200744L (sv)	1982-08-11
IN156817B (xx)	1985-11-09
NL8200180A (nl)	1982-09-01
GR75905B (xx)	1984-08-02
HU185088B (en)	1984-11-28
HK22485A (en)	1985-03-29
IE52376B1 (en)	1987-09-30
PT74408B (en)	1983-07-07
FI75347B (fi)	1988-02-29
FR2499406B1 (xx)	1984-03-30
IL64759A0 (en)	1982-03-31
ES8302714A1 (es)	1983-01-16

Publication	Publication Date	Title
LU83886A1 (fr)	1982-06-30	Nouveaux derives de la furo-(3,4-c)-pyridine leur preparation et leur emploi therapeutique
CH660191A5 (fr)	1987-03-31	Derives de la furo-(3,4-c)-pyridine, leur preparation et compositions therapeutiques contenant ces derives.
SU1087075A3 (ru)	1984-04-15	Способ получени производных фталазин-4-ил-уксусной кислоты или их солей
CA1036597A (fr)	1978-08-15	Pyrimidines utilisables comme medicaments antidiabetiques et hypocholesterolemiants
CH635813A5 (fr)	1983-04-29	1,9-dihydroxyoctahydrophenanthrenes et medicament les contenant.
LU85635A1 (fr)	1985-06-04	Nouveaux derives de la vinyl-6 furo-(3,4-c)-pyridine,leur preparation et compositions pharmaceutiques a base de ces composes
EP0239461A1 (fr)	1987-09-30	Dérivés de N-¬¬(hydroxy-2 phényl) (phényl) méthylène amino-2 éthyl acétamide, leur préparation et leur application en thérapeutique
FR2509734A1 (fr)	1983-01-21	Thiazolo(3,2-a)pyrimidines substituees et procedes pour leur preparation
FR2551063A1 (fr)	1985-03-01	Nouveaux dimethyl-2,5 pyrroles, leur procede de preparation et leur application en therapeutique
LU85583A1 (fr)	1985-04-02	Derives de la chloro-4-furo-(3,4-c)-pyridine,leur procede de preparation et compositions therapeutiques a base de ces derives
EP0179428A2 (en)	1986-04-30	Indoleacetic acid derivative and a pharmaceutical preparation
FR2572405A1 (fr)	1986-05-02	Nouveaux derives de la phenethylaminoalcoyle-6 furo-(3,4-c)-pyridine et leur procede de preparation
KR950008316B1 (ko)	1995-07-27	1-히드록시-5-옥소-5H-피리도[3,2-a]페녹사진-3-카르복실산 에스테르
LU86706A1 (fr)	1987-07-24	Nouveaux derives du benzo(4,5)cyclohepta(1,2-b)thiophene,leur preparation et leur utilisation comme medicaments
LU86053A1 (fr)	1986-02-18	Nouveaux derives de l'aminomethyle-6 furo-(3,4-c)-pyridine,leur preparation et compositions therapeutiques en contenant
WO1989012634A1 (fr)	1989-12-28	[(aryl-4-piperazinyl-1)-2 ethoxy]-3 p-cymene, les derives ortho, meta, para monosubstitues ou disubstitues sur le noyau phenyle dudit produit, le procede de preparation desdits derives, et les medicaments contenant lesdits composes comme principe actif
US4218473A (en)	1980-08-19	Derivatives of 4-cyclohexyl-1-naphthalene-acetic acid and their use as drugs
US4113960A (en)	1978-09-12	3-(4'-Alkoxy-benzoyl)-1,2,2-trimethyl-cyclopentane-carboxylic acids, their optical isomers and drugs containing such compounds
SU1739851A3 (ru)	1992-06-07	Способ получени производных тиено(3 @ ,4 @ :4,5)имидазо(2,1- @ )тиазола
FR2563520A1 (fr)	1985-10-31	Nouveaux derives d'apovincaminol, procede pour leur preparation et compositions pharmaceutiques les contenant
LU86052A1 (fr)	1986-02-18	Nouveau procede de preparation des derives de la furo-(3,4-c)-pyridine substitues en position 6
FR2565487A1 (fr)	1985-12-13	Compositions therapeutiques a base de nouveaux derives de l'aminomethyl-6 furo-(3,4-c)-pyridine
JPS61129179A (ja)	1986-06-17	１−ベンズオキセピン−５−オン誘導体
FR2465734A1 (fr)	1981-03-27	Procede de preparation de composes de furoindole, nouveaux produits ainsi obtenus, particulierement utilises comme agents analgesiques et anti-inflammatoires
CH617688A5 (en)	1980-06-13	Process for the preparation of new acetamidoxime derivatives