ZA200400145B - New compounds, which are potent inhibitors of Na<+>/Ca<2+> exchange mechanism and are useful in the treatment of arrhythmias. - Google Patents
New compounds, which are potent inhibitors of Na<+>/Ca<2+> exchange mechanism and are useful in the treatment of arrhythmias. Download PDFInfo
- Publication number
- ZA200400145B ZA200400145B ZA200400145A ZA200400145A ZA200400145B ZA 200400145 B ZA200400145 B ZA 200400145B ZA 200400145 A ZA200400145 A ZA 200400145A ZA 200400145 A ZA200400145 A ZA 200400145A ZA 200400145 B ZA200400145 B ZA 200400145B
- Authority
- ZA
- South Africa
- Prior art keywords
- yloxy
- chroman
- phenylchroman
- nmr
- mhz
- Prior art date
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- 230000007246 mechanism Effects 0.000 title claims description 12
- 206010003119 arrhythmia Diseases 0.000 title claims description 9
- 230000006793 arrhythmia Effects 0.000 title claims description 9
- 239000003112 inhibitor Substances 0.000 title description 5
- 230000003389 potentiating effect Effects 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims description 81
- -1 D Ro is H Chemical group 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 14
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- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
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- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- JYQQWQJCEUMXQZ-UHFFFAOYSA-N methyl cyanate Chemical compound COC#N JYQQWQJCEUMXQZ-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- ZBLUTZFHSCCKFN-UHFFFAOYSA-N n-(2-phenyl-2,3-dihydrochromen-4-ylidene)hydroxylamine Chemical class O1C2=CC=CC=C2C(=NO)CC1C1=CC=CC=C1 ZBLUTZFHSCCKFN-UHFFFAOYSA-N 0.000 description 1
- FNOADEAMIXWVQN-UHFFFAOYSA-N n-[6-[[2-(2,4-difluorophenyl)-3,4-dihydro-2h-chromen-6-yl]oxy]pyridin-3-yl]methanesulfonamide Chemical compound N1=CC(NS(=O)(=O)C)=CC=C1OC1=CC=C(OC(CC2)C=3C(=CC(F)=CC=3)F)C2=C1 FNOADEAMIXWVQN-UHFFFAOYSA-N 0.000 description 1
- VEDJKSPBAURNOE-UHFFFAOYSA-N n-[6-[[2-(4-fluorophenyl)-3,4-dihydro-2h-chromen-6-yl]oxy]pyridin-3-yl]methanesulfonamide Chemical compound N1=CC(NS(=O)(=O)C)=CC=C1OC1=CC=C(OC(CC2)C=3C=CC(F)=CC=3)C2=C1 VEDJKSPBAURNOE-UHFFFAOYSA-N 0.000 description 1
- ITVCIMHPTHXJOS-UHFFFAOYSA-N n-[6-[[2-[4-(trifluoromethyl)phenyl]-3,4-dihydro-2h-chromen-6-yl]oxy]pyridin-3-yl]acetamide Chemical compound N1=CC(NC(=O)C)=CC=C1OC1=CC=C(OC(CC2)C=3C=CC(=CC=3)C(F)(F)F)C2=C1 ITVCIMHPTHXJOS-UHFFFAOYSA-N 0.000 description 1
- WCWNTMPRUOWCAH-UHFFFAOYSA-N n-[6-[[4-hydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2h-chromen-6-yl]oxy]pyridin-3-yl]acetamide Chemical compound C1=CC(OC)=CC=C1C1OC2=CC=C(OC=3N=CC(NC(C)=O)=CC=3)C=C2C(O)C1 WCWNTMPRUOWCAH-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 238000001543 one-way ANOVA Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- HHAVHBDPWSUKHZ-UHFFFAOYSA-N propan-2-ol;propan-2-one Chemical compound CC(C)O.CC(C)=O HHAVHBDPWSUKHZ-UHFFFAOYSA-N 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000010410 reperfusion Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000002537 thrombolytic effect Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/90—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. amino-diphenylethers
-
- 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
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Vascular 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)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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FI20011507A FI20011507A0 (fi) | 2001-07-10 | 2001-07-10 | Uusia yhdisteitä |
Publications (1)
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ZA200400145B true ZA200400145B (en) | 2005-04-08 |
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Family Applications (1)
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ZA200400145A ZA200400145B (en) | 2001-07-10 | 2004-01-08 | New compounds, which are potent inhibitors of Na<+>/Ca<2+> exchange mechanism and are useful in the treatment of arrhythmias. |
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US (1) | US7425568B2 (sr) |
EP (1) | EP1412343B1 (sr) |
JP (1) | JP4113839B2 (sr) |
KR (1) | KR20040025697A (sr) |
CN (1) | CN1281597C (sr) |
AR (1) | AR036236A1 (sr) |
AT (1) | ATE338038T1 (sr) |
AU (1) | AU2002321339B2 (sr) |
BR (1) | BR0211070A (sr) |
CA (1) | CA2452918C (sr) |
DE (1) | DE60214388T2 (sr) |
DK (1) | DK1412343T3 (sr) |
EA (1) | EA006580B1 (sr) |
ES (1) | ES2269746T3 (sr) |
FI (1) | FI20011507A0 (sr) |
HK (1) | HK1068611A1 (sr) |
HR (1) | HRP20040133A2 (sr) |
HU (1) | HUP0400391A3 (sr) |
IL (2) | IL159647A0 (sr) |
MX (1) | MXPA04000267A (sr) |
NO (1) | NO20035821L (sr) |
NZ (1) | NZ530490A (sr) |
PL (1) | PL367958A1 (sr) |
PT (1) | PT1412343E (sr) |
RS (1) | RS50886B (sr) |
UA (1) | UA76168C2 (sr) |
WO (1) | WO2003006452A1 (sr) |
ZA (1) | ZA200400145B (sr) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FI20030030A0 (fi) * | 2003-01-09 | 2003-01-09 | Orion Corp | Uusia yhdisteitä |
ZA200707427B (en) | 2005-03-11 | 2008-11-26 | Florey Howard Inst | Flavonoid compounds and uses thereof |
US8912224B2 (en) | 2011-09-12 | 2014-12-16 | Sanofi | Substituted 2-(chroman-6-yloxy)-thiazoles and their use as pharmaceuticals |
JP5941637B2 (ja) * | 2011-09-12 | 2016-06-29 | サノフイ | 置換2−(クロマン−6−イルオキシ)−チアゾール及び医薬としてのその使用 |
SG11201400518RA (en) * | 2011-09-12 | 2014-04-28 | Sanofi Sa | Substituted 2-(chroman-6-yloxy)-thiazoles and their use as pharmaceuticals |
PT2567958E (pt) | 2011-09-12 | 2015-01-14 | Sanofi Sa | 2-(croman-6-iloxi)-tiazoles substituídos e sua utilização como produtos farmacêuticos |
CN102993195B (zh) * | 2011-09-14 | 2017-05-17 | 赛诺菲 | 取代的2‑(色满‑6‑基氧基)噻唑及其作为药物的用途 |
CN103030646B (zh) * | 2011-09-29 | 2016-08-24 | 上海恒瑞医药有限公司 | 苯并二氧六环类衍生物、其制备方法及其在医药上的应用 |
TWI633095B (zh) * | 2013-03-08 | 2018-08-21 | 賽諾菲公司 | 經取代-6-基氧基-環烷類及其作為醫藥品之用途 |
GB201416186D0 (en) | 2014-09-12 | 2014-10-29 | Redx Pharma Ltd | Compounds |
WO2019175464A1 (en) | 2018-03-14 | 2019-09-19 | Orion Corporation | Compounds useful as inhibitors of sodium-calcium exchanger (ncx) |
JP2023535790A (ja) | 2020-07-28 | 2023-08-21 | ジャズ ファーマシューティカルズ アイルランド リミテッド | 縮合二環式raf阻害薬及びその使用方法 |
Family Cites Families (14)
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US2820817A (en) * | 1954-02-04 | 1958-01-21 | Mcneilab Inc | Oxygenated indan compounds and method of making the same |
US3862232A (en) * | 1963-07-03 | 1975-01-21 | Upjohn Co | 1-(p-hydroxyphenyl)-2-phenyl-6-(2-diethylaminoethoxy)-3,4-dihydronaphthalene and the salts thereof |
BE650081A (sr) * | 1963-07-03 | |||
GB1154119A (en) * | 1968-05-20 | 1969-06-04 | Merck Ag E | 3-Alkyl-Flavanones |
FR2733685B1 (fr) * | 1995-05-05 | 1997-05-30 | Adir | Utilisation des derives du benzopyrane pour l'obtention de compositions pharmaceutiques destinees au traitement des pathologies liees a l'echangeur c1-/hc03-, na+ independant |
JPH0967336A (ja) | 1995-09-04 | 1997-03-11 | Kanebo Ltd | 新規なイソチオウレア誘導体 |
ATE230720T1 (de) | 1997-03-27 | 2003-01-15 | Taisho Pharmaceutical Co Ltd | 2-phenoxyanilinderivate |
JPH1149752A (ja) * | 1997-08-05 | 1999-02-23 | Taisho Pharmaceut Co Ltd | フェノキシピリジン誘導体 |
DE19742508A1 (de) | 1997-09-26 | 1999-04-01 | Hoechst Marion Roussel De Gmbh | Sulfonamid-substituierte Chromane, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltende pharmazeutische Zubereitungen |
ATE231487T1 (de) * | 1997-10-20 | 2003-02-15 | Taisho Pharmaceutical Co Ltd | 2-phenoxyanilin-derivate |
JPH11302235A (ja) | 1998-04-15 | 1999-11-02 | Taisho Pharmaceut Co Ltd | フェノキシアルキルアミン誘導体 |
EP1180029A4 (en) * | 1999-04-23 | 2002-10-02 | Bristol Myers Squibb Co | BICYCLIC ACYL IHIBITORING SODIUM / PROTON EXCHANGER AND RELATED PROCEDURE. |
AU766935B2 (en) | 1999-09-17 | 2003-10-23 | Nissan Chemical Industries Ltd. | Benzopyran derivative |
FI20030030A0 (fi) | 2003-01-09 | 2003-01-09 | Orion Corp | Uusia yhdisteitä |
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2001
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2002
- 2002-07-10 MX MXPA04000267A patent/MXPA04000267A/es active IP Right Grant
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2003
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2004
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2005
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